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Nifty - Transgender - Control - My Mommy Made Me A Sissy

Date: Fri, 4 May 2012 22:12:21 -0700 (PDT)
From: Melissa Brooks <>
Subject: My Mommy Made Me a Sissy

by: Missy Satinpanties

       I was about 5 or 6 when my father left, leaving me with just my
mother. A mother that I came to love very, very much. Maybe, I loved her
too much. And Mommy definitely loved me too well!
       A quick family history would be appropriate right now. My parents
got married when Mom was only 18, and Dad was an old man of 20. Pregnancy
either occurred just after, or just prior to the wedding. As a result, I
still had a young, and very pretty mother. As I said, about five years
after the wedding, my father just up and left us. Mother was really broken
up after he left, even though we were pretty well off, thanks to the
passing of her mom and dad, who had left her a sizeable chunk of cash and
about a dozen rental properties, along with a stock and bond portfolio that
produced some nice quarterly returns. Since Mom owned the condo outright
(a wedding gift from her aunt), there weren't too many bills to worry
about. Now, money aside, Mom reacted badly to Dad's leaving, and broke off
contact with a lot of her friends, and shortly thereafter, she sold the
condo, and we moved from the city, to a big house in the country.

Now, I realize she was running away from memories. After Dad was
gone, I spent a lot of time hanging around Mom. Since we now lived out in
the country and there just weren't that many kids around. I remember being
in her room while she was dressing, and admiring all the pretty things she
wore. I would do the kiddy thing and put a slip on like a dress, put my
feet into her heels, and try to walk around the room, and Mom would laugh
and call me her little princess. She would pick me up and hug me, and I
came to love the close bond we had. Later, as I got a bit older, I would
still hang around my mother, but now with a bit more interest. I would
still pull on one of her slips or nighties, and she would still laugh, but
then things got a little different.

       We were in Mom's bedroom one rainy summer's morning, and had just
finished making the beds and vacuuming the upstairs, when she turned to me
and asked me if I still liked wearing her clothes. This was like a bolt
out of the blue. I was a teenager, and even though I was a bit embarrassed
about it, I did love our little game where I put something on, and she
would hug me tight. and to be quite honest, I was beginning to love wearing
her soft silky things. So, I told her how pretty and soft her things were,
and how lucky girls were to be able to wear such nice things. Mom laughed,
took my hand, and led me to the bed. "Now Mikey," she began softly, "would
you do something special for Mommy? Would you do something special that's
also a little silly for Mommy that would make her very happy?" Now, I
hadn't called Mom "Mommy" for many years, but I told her that I would do
whatever it took to make Mommy happy. I think that was the beginning, the
real beginning.

       She told me to take off my clothes for her, and I took off my
shorts, t-shirt, socks and shoes, and stood there in my little white
underpants. Mom smiled, and then reached over and slipped her thumbs into
the waistband of the underpants, and slid them down my legs. I was old
enough to get a stiffy from this, but not quite old enough to know what to
do about it, or even do with it! I started to protest, but she put her
finger to my lips and told me to be quiet and relax, everything would be
okay. Now, my mom was about 5'5" tall, with long dark blonde hair, pale
green eyes, and now that I look back at all the pictures, the body of a 16
year old cheerleader. I was a little shorter at the time, but skinny, with
the same hair and eyes. Of course, my hair was shorter, and being a boy,
never taken care of properly. Mom, or as she asked me to call her, "Mommy"
took me by the hand and led me to her bathroom. She sat me down on the
toilet seat while she ran a bath and added some bath oil. When the tub was
full, she took off the white cotton blouse she was wearing, and with her
breasts covered in just a white lacy bra, she helped me into the hot
fragrant water. After I was in, she began to wash my hair with a shampoo
that smelled like the bath oil. She washed it twice, both times rinsing it
with a flexible hosed shower head. Now, Mom hadn't given me a bath since I
was a toddler, but I had to admit it all felt pretty good, and even though
she was my mother, those breasts were so close and so beautiful!

       After my hair was clean, she told me to stand up, and she wrapped a
big fluffy towel around me, and lifted me out, just like I was a baby.
Standing on the rug, she dried me off, and then went to the bathroom door,
where she took down her pink satin robe, and slid my arms into it, tying it
off around me. I loved the cool, silky smooth material, but... Again, I
was told to relax. She led me back into her room, and sat me down in front
of her mirror and began to work on my hair with a comb, brush, and
blow-dryer. Fifteen minutes later, my hair was dry, and looked a little
girly. She stood me up, and rummaged around in her dresser, and then told
me to turn around and close my eyes, really tight. I was standing with my
back to her, and she reached around and undid the sash of the robe, and
slipped it off of me. She then told me to lift up a foot then the other,
and then she slipped what I knew had to be a pair of soft panties up my
legs, and settled them into place. She then told me to hold my arms out in
front of me, and to keep my eyes closed like a good boy. She slipped
something over my arms and then over my shoulders, and I knew it was a bra,
but kept my eyes closed like a good boy. She fastened it behind me, and
did something with the straps, and then told me to open my eyes and turn
around. I found myself looking into the mirror at what used to be a boy,
but was now more like a skinny girl! I was wearing what Mommy told me were
full-cut satin sissy panties and I could see for myself they were pink
satin trimmed with lots of white lace around the legs and waist, and that
the bra matched the panties. Mommy told me that she saw these on a web
site, and just could not resist getting them for "her little princess."
With that, I know I blushed as pink as the satin!

       I spent the rest of the day wearing my new bra and panties, with
Mommy's pink robe over all. I started out feeling very silly, then kind of
sexy, but after a few hours of helping with the housework, watching some
TV, and messing around on the computer, I completely forgot what I was
wearing! That evening, Mommy came to my room to tuck me in, something she
hadn't done in years. I was standing there in my pink lingerie, and Mommy
asked me if I liked wearing the pretty things. I wanted her to be happy,
and I didn't mind wearing them, so I told her I liked wearing them very
much. This got me a big smile and hug. Mommy told me to take off my new
things, and get ready for bed. I thought she would leave, but she stood
there while I removed the robe, and with some help, removed the bra. When
I saw she was staying, I shrugged, and pulled off the panties. Mommy
handed me my pajamas, and tucked me in, kissing me goodnight.

       Nothing else happened for a few days, and then Sunday morning, we
were back In Mommy's bedroom. I saw "my" bra and panties on the bed, along
with a white box with a pink bow on it. Once again, I was given a bath, and
my hair was washed, and once again I was helped into the smooth, soft
satin, and then Mommy told me to open the box. Inside was a beautiful pink
satin robe, trimmed with white lace and ribbons, that Mommy told me to call
peignoir. I lifted this peignoir out of the box, and saw something else
under it. Mommy had me lay the peignoir on the bed, and she took out a
pair of pink nylon socks and a pair of shiny white shoes. I was told to
sit on the bed, and Mommy pulled the short socks over my feet, and then
fitted the white shoes on my feet. She called the shoes Mary Janes, and
they looked just like what a little girl would wear. I stood back up, and
she slipped the robe on me. I have to admit that I loved the cool,
slithery sensation as I moved. She fastened the one button at my chest,
and told me how pretty I looked. Again, hugs and kisses, but this time,
Mommy caressed my satin clad bottom, making me feel weak in the knees.
Again, I spent the rest of the day in my new finery.
       All that summer, Mom would call me into her room every week or so,
and give me some more girly things. Mostly, they were more panties and
bras in a variety of satin in soft girly colors, but there were some more
socks, several pairs with a cloud of lace at the ankle, and two more pair
of shoes, one in pink and one in shiny black to match my white ones. I was
getting a little uncomfortable, I mean, I wasn't a girl, but Mom never
pushed me, and I did enjoy those hugs and kisses. Okay, they were kisses
that were more appropriate to a girlfriend than a mother sometimes, but
that just added to the fun. I mean, a boy wearing lingerie was a taboo,
right? And having his very pretty mother kiss him on the lips, while he
was wearing lingerie was most certainly taboo, but it wasn't hurting
anyone, and it felt good. Besides, I felt that I was making Mommy very
happy, and that made me happy.
       School started back up, and was a drag. I was small, didn't play
sports, wasn't smart enough to be a nerd, didn't smoke pot, and in short,
fit in with no group. Other than watching the girls, I can't say I liked
school at all. Even though I wasn't a brainiac, I read all the time, and
really knew most of the pabulum that was passed off as public education. I
wished I could go somewhere, anywhere, else. Anyway, back at home, Mom
told me that she would put the girly things in the dresser in the spare
room, and we could play with them on special occasions. We played dress-up
a few cold rainy weekends, and she kept me in my panties and bra almost all
the time over the Thanksgiving break. But over Christmas, well let me tell
you about Christmas!

       Exposure to the boys (and girls!) at school, along with a few peeks
at various men's magazines, including a well-thumbed Penthouse that I
bought from a Junior for ten bucks had helped me grow up, at least a bit,
sexually. I now knew not only why my cock got hard, I knew what to do with
it to feel really good! The only problem I had was in what you might call
"visualization." You see, there was this one picture of a beautiful woman
in a pair of lace trimmed, white silky panties, matching bra, white
stockings and high-heeled pumps. One of the bra straps was down over her
arm allowing a nipple to poke out of the not very substantial garment. She
was kneeling in front of a man who was wearing only boxers and a bulge. In
the next picture, her bra was off, and her hand was the man's thick erect
penis. I would stare at those pictures while I masturbated, but in my
mind, sometimes I was the man, sometimes the woman, and sometimes the woman
was my Mother! Yeah, I was just a teensy bit confused.

       Well, back to Christmas morning. Mom came into my room early and
woke me up. As I opened my eyes, the first thing I saw were my mother's
beautiful breasts through an almost sheer white nightgown trimmed with
white satin and baby blue ribbons and bows. The gown was covered (?) by a
sheer robe that I learned to call a peignoir. Her breasts were firm mounds
with erect nipples that about poked through the material. This was my
mother and I was aroused,, but I thought I was still dreaming! She bent
down and kissed my cheek, and told me that it was Christmas morning, and
that Santa had brought some wonderful presents for "her little princess!"
I was still half-asleep, and mesmerized by those breasts and her soft
fragrant perfume, so it took a moment for that comment to sink in. By the
time it registered, Mommy (she insisted that I only call her Mommy at home)
had pulled me from my bed, and was unbuttoning my pajama top and pulling it
off of me. Telling me to just stand still, she pulled my bottoms off,
smacked my bottom, and told me to get to her room for a bath. We went into
her bathroom, and Mommy stopped only long enough to remove the peignoir,
and to pull on a clear plastic, over-the-shoulder apron, trimmed in white
lace. Once that was done, she did an odd thing, and knelt on the bathroom
rug by my feet.
"Now, Mikey," she asked me rather seriously, "would you be willing
to give Mommy a very special Christmas present, even if it sounds a little
odd? I promise you, that if you do, Mommy will make this your best
Christmas ever." With that, she blew my little mind by leaning in and
kissing the head of my cock! She gave it a little lick, and looked up at
me, "Well, does Mommy get what she wants?" I didn't care what she wanted,
the answer was yes, Yes, YES! With that enthusiastic answer, she licked
the full length of my small, but rock-hard penis, and stood up. I was told
to stand still. Mommy got a plastic bottle of something, and after pulling
on a pair of rubber gloves, she smeared this lotion all over my legs,
chest, arms, underarms, and back. Now I didn't have much hair, and when I
saw what the bottle was, I knew I wouldn't have any left. I stood there
the required time, and then Mommy stood me in the tub and rinsed me off
with warm water and a sponge. Still standing there, she lathered up my
rock hard penis and balls, and told me to stand very still while she plied
her lady's razor to what little pubic hair I had. A few minutes later, I
was told to turn around, bend over, and spread my butt cheeks. She
repeated the process there, leaving me hairless and very horny.
She wrapped a towel around my shoulders, and rinsed out the tub.
She then filled it with hot water and added some very feminine bath oil.
Once it was filled, she helped me step in like a little child, and began to
shampoo my now shoulder-length hair. After she washed my hair twice in
perfumed shampoo that smelled just as feminine as the bath oil, she picked
up a sponge and began to wash me all over. I protested, but she again to
me to relax. She paid particular attention to my cock which was now
embarrassingly rock hard, and my behind. I didn't mind this wonderful
attention at all, even when Mommy pushed her finger into my butt hole a
       Once my bath was done, she helped me out of the tub, knelt at my
feet again, and began to dry me off, as though I couldn't do it myself.
But hey, even if she was my mother, she was one of the most beautiful women
I had ever seen in person, and if she wanted to lavish this attention on
me, who was I to argue? After Mommy dried me all off, she handed me a
bottle of lotion, and told me to rub it in, all over, and it would help
with any irritation. It was again the same delicate fragrance as the bath
oil and shampoo. When I had done that, I was told to come back out into
Mommy's room. Once there, I put on my sissy pink satin panties and bra,
and Mommy told me that I would get to wear a very special outfit for
Christmas. First, I was told to go to the closet door and grab the bar
that was there. I reached up, on my toes, and wrapped my hands around the
bar. As soon as I did, Mommy snapped a pair of handcuffs on me, cuffing me
to the steel bar. Before I could even protest, she reached around and
began to caress my nipples through the satin of the bra, making me moan out
loud. She moved my hair out of the way, and began to kiss my neck while
she gently pinched and twisted my nipples, Finally, one hand dropped to
gently caress my cock through the satin of my panties. She only did it for
a second, but I almost shot my load right then and there/ "There," Mommy
whispered in my ear, "Every time you do something for Mommy, Mommy will do
something nice for you. And each time, it will get nicer and nicer! Of
course, if you are a bad little girl, Mommy may have to punish her
princess." She giggled as she said this, so I paid little attention.
Let's face it, my Mom had me in soft girly lingerie, and was starting to
make out with me, words had very little meaning at that point!
       Mom patted me on the bottom, and told me that she was going to put
a corset on me to give me a little more figure, and if I was good...Oh yeah
I was gonna be good! She produced a white satin corset with white lace
trim, wrapped it around my middle, laced it up, and then told me to take a
deep breath. With those words, she pulled the laced real tight, and tied
them off. At first I couldn't breathe, but within a moment or two, it felt
okay. She told me that it wasn't nearly as tight as it could go, but was
tight enough to make me look good.
       The next few hours were a blur. I opened package after package,
containing dresses, nighties, panties, bras, shoes, and all manner of
sissy-styled girly clothing. About half-way through, Mommy told me I had
been such a good girl, trying on all my new clothing, that she had two
special surprises for me. The first one was a new, top-of-the-line
notebook computer, designed for gaming. The second surprise almost made me
forget about the computer.
       I was wearing the last dress I had been given by "Santa." It was a
baby blue satin creation with a very short skirt, like most of the dresses
I had tried on. I stood there, dressed like no boy should ever be dressed.
I was still wearing the white corset, and now there was a pair of pale blue
satin panties trimmed with yards of white lace, not only around the waist
and leg opening, but in three frilly rows across my bottom. I was also
wearing a frilly training bra that matched my beautiful panties, white
patent leather Mary Jane shoes, white nylon ankle socks with a cloud of
white lace around the top, and the poofiest, sissiest blue satin dress you
can imagine. It had short cap sleeves with a white satin bow on each
shoulder, a Peter Pan collar of white satin, a wide sash of white satin,
tied in a big bow in back, and layer upon layer of ruffled, lacy, white
petticoats to make the skirt stand out. I was also wearing a pair of short
white satin gloves with lace at the cuff, and a white, ruffled satin
choker. The crowning touch was a baby blue ribbon in my hair. I stood in
front of the full length mirror and turned this way and that. When I stood
on my toes, and looked back over my shoulder to see my frilly bottom in the
mirror, Mommy just laughed. "Just like a woman!" she giggled. I didn't
care. I was a boy, I wasn't a girl or woman, but I just loved this dress!
I loved the feel of the satin against my skin, the feel and sound of the
petticoats as they swished when I turned. Was I some kind of sissy? Was I
gay? Hell, I knew what I was. I was a confused and excited young man. I
loved playing this game, even though I had no idea that the game was
rigged, and the house always won.

For the rest of the afternoon, I sat at the kitchen table in my
beautiful new dress, and played a bit with my new computer. I could get
on-line in a flash, and the starter game Mommy had bought with the computer
was great! I did notice that there seemed to be a few websites preloaded
into the browser. I would have to see what that was all about. Hmmm,
Sissy Kiss? Fictionmania? I was just going to check them out when Mommy
told me to put down my new computer for just a few minutes, and come with
her, as she had one more, really big present for me. She took my hand and
led me upstairs to the spare bedroom. Now, this room was usually locked,
but today it opened at the touch of my satin gloved hand. As it swung
open, I beheld a room fit for a little girl! There was a white canopy bed
with pink and white satin comforter, pink curtains at the windows, delicate
white furniture, and a matching dressing table, like Mommy had, complete
with a little stool with a pink satin cushion. There was even a brush ad
comb set, a bottle of perfume, some make-up and lipstick neatly laid out on
       I just stood there with my mouth hanging open, not knowing what to
say. Mommy never let go of my hand, but with the other hand, she reached
under my dress, and caressed my stiff member. "You don't have to talk,
Princess,' she whispered, "I know you like it! Now, come inside for the
rest of your Christmas Present. Still holding my hand, she led me into the
room. I was dressed like a 5 year old girl going to a party, or some kiddy
beauty pageant, and Mommy was still wearing that wonderful white negligee
with the matching sheer robe, and white high-heeled slippers with some kind
of white feathery stuff on the instep. She was beautiful sexy, I was so
turned on I was ready to scream, so, OF COURSE I followed her into her
       She led me to the bed, where a heavy, cream colored envelope
lay. The name "Tammy" was written across it in my mother's beautiful
penmanship. "That's yours, Princess," she said softly, "Go ahead and open
it." I unfolded the flap, and stared at the official documents inside.
Finally, I was able to make sense of the legalese and realized that after
Christmas, I was to be home schooled! That was wonderful news to me, as I
hated school and felt as though I learned nothing there. I looked at Mommy
and asked her who Tammy was. "Why," she giggled, "That's you, my little
princess! Or at least, when you're dressed so adorably! I can't possibly
call such a delicious confection like you Mike, can I? Why, not only do
you look like a little princess, you even smell like one! Now, Mikey never
even liked to shower, but Tammy, well..."
       I stood there for moment, and then broke down and started crying.
things were moving way too fast, and in directions that I couldn't even
begin to fathom. Mommy knelt down and took me in her arms, holding me
close. I wrapped my arms around her and buried my face in her thick hair.
The sweet, delicate fragrance of her perfume, the soft, silky material of
her gown, and the feel of those soft breasts pressing against me soon
calmed me down, and my tears slowed to sniffles. Mommy stood up, and went
to the dressing table where she grabbed some tissues to dry my eyes, and
blow my nose.
       "I thought you would be happy, sweetheart," she said softly. "All
I wanted was my little princess to be the happiest little girl on earth!"
I stammered out that I was not a little girl, no matter how much she
dressed me in these wonderful outfits. "So, you do like the dresses, the
panties, and all the other soft frilly things?" "Yes Mommy, but everything
is going so fast, and I just don't know what you want me to do, or say, or
be!" With that, I started to cry again, and again, Mommy took me in her
arms. But, this time, she picked me and put me on the "princess bed," and
sat down beside me. "My little man," she whispered, with her soft arm
around my waist, "I just want you to be happy, to feel loved, and to wear
whatever you want, whenever you want to. Do you want to put on your boy
clothes and play with your computer? With the new wireless router, you can
sit in your room and play all day and night if you like. Or, you can be my
little princess for just a little longer, and I will make it a very special
time for you."
       I knew Mommy wanted me to wear the girly clothes, and I so wanted
her to be happy, so I told her I would wear the pretty things until she
wanted me to take them off. With that, she began to kiss my forehead, and
moved to my cheeks, and then, without warning, kissed me on the lips. I
froze for a second, and then nature kicked in, and I returned the kiss as
best I could. She parted my lips with her tongue, and I locked my arms
around her neck, and realized I never wanted this kiss to end!
       It ended sooner than I wanted, but then she did a wondrous thing.
She pushed me back so I was lying on the bed, with my feet dangling off the
side. Then, she got out of the bed and knelt down in front of me on the
soft rug, and began to rub my cock through the soft satin panties. My
little man responded quickly, and before I knew it, she was sliding the
soft panties down, and had begun to kiss me on my hairless cock and balls.
"Oh, Tammy," she cooed, "I just love your little clitty!" I heard her say
that, but it didn't register. I was in heaven, and very confused. She
took me in her mouth, and gave me my first blow job, sending me into orbit
when I came! Climbing back on the bed, she kissed me, and shared my cum
with me. I was so shocked I never offered a bit of protest, and then we
lay there cuddling for the longest time, with her whispering in my ear how
good girls get very nice rewards. I had no idea at all what the heck was
going on, but at that point, I wanted to keep going forever!
       I learned that fateful Christmas day that this girly room was mine,
to use whenever I wanted to. We carried up all of my new panties, bras,
dresses, socks, and shoes, and put them away. Mommy asked me to stay in my
beautiful dress for the rest of the day, and I didn't feel like arguing.
We had a very nice Christmas dinner, and then sat down together to watch a
few Christmas movies. Mommy had gotten dressed, but was wearing a white
satin blouse that was sheer enough to show the pink lacy bra underneath,
and a blue wool skirt, stockings and black high heels. She looked very
glamorous to me. Finally, she told me that it was time for beddy-byes, and
one more Christmas surprise.
       Taking my still gloved hand in hers, we went upstairs to my new
bedroom. Once there, she helped me to take off my dress and hung it in my
closet, then unlaced my corset. It had not been too tight, and I had
really forgotten it was there at all. After I was undressed down to my
pretty panties and bra, Mommy told me to sit down on the bed. I did as she
asked, and then Mommy slowly unbuttoned her blouse, and let it slide off
her shoulders. The zipper on her skirt was pulled down, and it joined the
blouse on the floor. My mother, my Mommy, stood there in black heels,
black stockings, pink silk panties, a pink garter belt, and matching bra.
Slowly she came to the bed, and told me that since I had been a very good
girl, Tammy would have a very special bedtime snack. She then told me
kneel on the floor, and face the bed. Again, mesmerized by the sheer
amount of sexual energy in the room, I did what I was told. Mommy slowly
slid those wispy panties down her long, smooth legs, and sat down on the
bed, right in front of me, and put those wonderful legs over my shoulders!
I could smell the musk of her, and when she told me to lean in close and
kiss her shaved sex, I only hesitated for a moment. Soon, my young face
was buried in her sweetness, and with ample direction from Mommy, I was
able to bring her to an orgasm. Shaking, she gently pushed my head back,
and took her legs off of me. She stood up, and helped me to my feet.
Without a word, she began to kiss me, my mouth, my face, and the whole time
she did, she was rubbing my panty-clad ass and my back. I had a rather
uneasy feeling that this was all so very wrong, but pure adolescent
hormonal overdrive took care of those doubts.
       Mommy then took off her bra, and on impulse, I began to kiss and
suck one of her hard nipples. With a few cautions about biting too hard,
she began breathing hard, and began to work her fingers in and out of her
sex, and quickly had another orgasm. With that, we gently broke apart, and
she told me to finish getting undressed, and Mommy would give me a bath and
tuck me in my nice new bed. Mommy gave me my usual girly bath, but this
time in just a garter belt and stockings. I had heard the term MILF
bandied about the school, now I knew what it meant! After my bath, Mommy
dried me off with a pink towel, and then just stopped and looked at me.
"Sweetheart, do you want to sleep in your new room as Tammy tonight, or in
your old room as Mike?" I told her that I was her Tammy tonight, and she
kissed my forehead and took a pink satin robe down from the door hook and
wrapped it around me. She then picked up a pair of what looked like pink
satin ballet shoes with a sole, sat me down on the toilet and slid these
slippers on my feet. I noticed that beside the pink robe was my navy blue
cotton robe, and beside the ballet slippers were my rubber flip-flops that
I wore as slippers. I guess both choices were covered, and it seemed to me
that I could make that choice easily. Well...

       Mommy, still mostly naked, took me to my new room and she would be
there in just a sec. She made a detour into her room, and came back
wearing a black satin robe that was so shiny it looked like it was wet, and
seemed to flow around her body like a kind of liquid. She went to the
dresser and opened a drawer, and stood there for a moment, putting her hand
in, then stopping, closed that drawer and opened another, moved on to a
third, and finally, with a look of triumph on her face, she pulled out a
pink something. Turning to me, she asked me if I would do one itty bitty
thing more for Mommy to make Mommy's Christmas so very special. I told her
I would do anything she wanted me to. She told me to take off my robe, and
handed me a pair of ultra frilly satin panties that seemed to be lined in
plastic. She told me to throw them on the bed, and hold my arms up. When
I did, she slid a pink nightgown down over me that came in ripples to the
floor. It had long sleeves that ended in ruffles, and was very soft and
pretty. Turning me around, she proceeded to fasten the buttons at the
back, right up to the collar. Telling me to pick up the hem of my nightie,
I was to sit on the bed, and lay back. I heard another drawer opening, and
then Mommy told me to pick my cute little bottom up off the bed. When I
did, she slid the nightgown up over my waist. Giving my pee-pee another
long lingering kiss, she told me to hold still for a moment. She picked up
something, and put it on the bed, under me. Telling me to put my bottom
down, she proceeded to pin a thick baby diaper on me! I started to
protest, but Mommy got very stern and told me that I made a promise to do
one little thing, and now I was getting pissy about it. If I didn't want
my little bottom spanked, I had better just be quiet. WOW!

       I held my tongue as my diaper was pinned on, and didn't say a word
when those plastic lined sissy panties were pulled up my legs and snugged
into place around my diapers. Mommy stood me up, and took me in her arms.
"No sweetheart, I'm not mad at you! I know you are very confused, but
that's okay. I sort of want to play dress-up with you, and you have been a
very good sport. Any time tomorrow after you wake up, you can just walk
down the hall, put on your cotton underpants and jeans and be Mike
whenever, and for as long as, you like." With that she picked up a
pacifier, put it in my mouth, and tied the white ribbons behind my head to
hold it in. A lace-frilled satin baby bonnet in the same pink as my
nightgown was placed on my head, and tied off under my chin. Mommy stopped
and stared at me with a look of satisfaction and what I thought was love.
She told me to hold out my hands, placed pink satin mittens on my hands
that had no fingers or thumbs, and had some kind of thick lining. These
were tied tight around my wrists, and a little flap on the cuff buttoned
into the sleeves of the nightgown. My hands were now useless. Mommy
stepped around me and turned down my comforter, and I saw for the first
time that the sheets were pale pink satin. I got into bed, loving the
slithery feel as the satin of my nightgown rubbed the satin sheets, and
Mommy pulled the sheet and comforter up over me, and handed me a baby
bottle full of apple juice. "Drink it down, my little princess, and then
it's off to dreamland for you!" I went along, and sucked at the oversized
nipple until the bottle was empty. I found out that I had to hold the
bottle with both mittened hands, as I could not even wrap one around the
silly thing. Mommy just stood there, beaming, until I finished the bottle.
She took it from me, and then did something very odd.

       She lifted up the foot of the comforter, and played with something.
She then grabbed my foot, and placed something soft, tightly around my left
ankle, the one closest to the wall. I heard a little snick, and she pulled
the comforter back down. "There now," she cooed, "My little baby Tammy is
snug in her little diaper and nightie, and I put a little locking restraint
on my baby to keep her all safe in her widdle beddy. We wouldn't want some
bad man to kidnap my widdle baby now, would we?" I started to protest, and
started to try to get out of bed, but my foot would only move a few inches.
I started to fuss and fume, but found myself getting groggy, my words
slurring. "There was a sedative in your juice, sweetie. I knew you would
get all worked up, and not get any sleep, and today was so tiring, I just
wanted you to get some good sleepy time." My head dropped back on the
satin covered pillow, and Mommy reached down, kissed my forehead and cheek,
and told me to have sweet girly dreams about fairies, and princesses, and a
handsome prince! I wanted to protest, but fell fast asleep.

       I woke up with that strange feeling of not knowing where I was.
Slowly, as though a fog, it all came back to me. I had sex, at least
orally, with my mom last night! I also remembered that I was in a girl's
room, dressed like a baby girl, complete with diaper. I brought my useless
hands up to pull the covers off of me, or at least I tried. My hands,
still encased in the mittens, were secured to my sides, and I could only
move them a few inches. I was stuck in bed, gagged with a pacifier, and I
had to pee really badly! I held it as long as I could, and finally nature
won out over dignity and I peed into my diaper. I have to admit that It
felt kinda good. I mean, I was in a soft satin nightie, tucked into satin
sheets on a cold winter morning, and all I had to do was lie here in the
soft warmth, and since I was wearing diapers, I didn't even have to get up
to do that! I drifted back to sleep with that thought, and a very wet
I had been napping again for another hour or so when the door opened
quietly, and Mommy slipped in. "Oh goody!" she cried, "My precious baby is
awake!" Very gently, she untied the pacifier, and helped me into a sitting
position. She then produced the baby bottle, and told me not to worry, it
was just plain juice, and she was so sorry for going a bit overboard last
night. Mommy was wearing a royal blue nightgown with long sleeves that
ended in lace. Her soft arm was behind my head, and her breasts were
against the side of my head, and she was holding a bottle for me to drink
from. I know I should have been angry and revolted, but it felt so good, I
just went with the program. After my morning bottle, Mommy laid me back
down, and pulled the covers off of me. She undid the fasteners that held
my arms down, and took off the ankle restraint, and helped me out of bed.
Reaching up under my nightie she felt my diapers, and looked as though she
couldn't be happier to find them sopping wet!

       She undid my hands from the mittens, unbuttoned my nightgown, and
then placed a plastic sheet on the bed. Instructing me to down on the
sheet and to lift my cute little bottom, she slid off my satin covered
plastic panties, and removed my diaper, cleaning me up with some baby
wipes. Again, here I was, a young man, and I had just had my satin
nightgown removed so my Mommy change my diaper! I lay there for a few
moments, thinking it all through, and didn't hear Mommy the first time.
"What did you say?" I asked. "Do you want to be Tammy or Mike today,
sweetheart? Whatever you want, no pressure." I lay there again for a
minute, and told her that I thought I wanted to be a boy again. Mommy left
the room for a moment, and I thought I had made her mad or something. Just
when I was about to call her back and change my mind, she showed back up
with my boy robe and slippers, told me to take a shower and come down for

Twenty minutes later, dressed in jeans, sweatshirt and trainers, I was
sitting down to a nice breakfast with my Mom. The rest of the day was
rather ordinary. I spent a lot of time sitting around with my new
computer, playing video games, and checking out the web. Everything was
normal, except there was no hint of anything other than a mother and her
son. Mom was wearing jeans and a bulky sweater, I got no kisses or
caresses, and that night when I went to bed in my boy's room, in my boy's
PJs, all I got was a kiss on the forehead and a soft good night.

I lay there a long time, thinking about everything that had gone on
for the last year, and especially the last few days. Instead of Mommy
giving me a bath, I took a regular shower. My jeans and cotton underwear
were the same as they had always been, but felt coarse and rough against my
shaved legs and crotch. Plus, as bizarre and irregular as it might be, I
wanted my mother back in my bed, and the rather pointed sexual dreams I had
that night bore this out. I woke up very early the next morning, my full
bladder forcing me awake before I was ready. Remembering the soft satin,
and the thick diaper, I was a bit grumpy as I padded down the cold hallway,
and used the toilet. Instead of going back to bed, I stood in the cold
hallway a while, thinking. As a bit of an experiment, I went past my
normal room, and into Tammy's bedroom. I took off my robe, slippers, and
PJs, and went rooting in the nightie drawer. I found a baby pink satin
camisole and tap pant set, and figured that these were pretty girly, put
them on. I also found the mittens and bonnet from the other night, and
even though I couldn't tie the mittens, the elastic kept them on my hands.
Dressed as much as I could, I climbed into the satin sheets to wait for
morning. I found the feel of the cool, slithery-soft satin against my
satin covered skin gave me a hard-on like a hunk of steel, but I resisted
playing with myself, and forced myself to relax and get a little more
sleep. Just before I drifted off, I saw a teddy bear in a pink satin
ballerina outfit on the headboard. I reached up, cuddled it close, and
went back to sleep.
About nine that morning, I was awakened by the bedroom door opening,
and Mommy's giggle. As I came more fully awake, I saw that she was wearing
what I would soon learn was called a teddy. It was a shimmering white
garment, with fluttery ruffles of the same material around the high leg
openings, and two panels of beautiful lace on the front. Over it, she was
wearing a sheer bed jacket of white lace. She looked beautiful! Without a
word, she slipped into the room, pulled back the covers, slipped off the
bed jacket, and slid in beside me. Under those soft sheets, she wrapped her
arms around me, and began kissing me, calling me "her sweet Tammy." I kept
trying to push my crotch into hers, as there was nothing but two wispy
pieces of satin separating me from that treasure, but Mommy kept her lower
body away from me. Sigh. Nothing more in a sexual way happened that day,
but as I decided to experiment and spend the day as Tammy, I got a whole
lot more cuddling, kissing, and personal attention that I ever did as Mike.
That night, I slept like baby, literally. Mommy had helped me take
off my pretty dress and then gave me a bath, washing and drying my hair.
Once again in my pink satin robe and ballet slippers, I was led back to
Tammy's room. Mommy started to walk to the dresser, but stopped, and
looked at me. I knew what she wanted, and had already made up my mind. I
walked to the nightstand where my pacifier sat on a lacy doily. I picked
it up, stuck in my mouth, and let my robe slip to the floor. I crawled up
onto the bed, lay on my back, and held my little bottom up to be diapered.
A very short time later, I was back in thick cloth diapers, pale yellow
plastic panties, and a yellow trimmed, white satin garment that Mommy
called a special made "onsie."

This garment had long sleeves that were sewn to sides of the body, and
legs that were a very tight, one piece affair, all the way to the ankles.
I could not move a muscle! Mommy left me lying on the turned-down bed, and
telling me that she would be back, left the room. she swept back in
wearing that beautiful royal blue negligee, and looking very sexy. She
helped me up into a sitting position, and asked me if I thought I could go
sleepies all by my widdle self, or did I need a little help. I told her
that I was tired, and would not need a sedative, so she held my bottle of
apple juice to my lips until I sucked it dry. Then, she slipped the strap
off her shoulder, exposing one of her beautiful breasts. I began to suck
and kiss it, and Mommy began to rub my pee-pee through the thick layers of
satin, plastic and cotton. After a few minutes of this, I was laid down,
and Mommy tied my pacifier in my mouth and yellow satin bonnet on my head.
Finally, she reached up under her negligee, and pulled off her panties.
They were the same blue as the negligee, and gossamer thin. Giggling, she
put her nose in the crotch and inhaled, Then, she arranged them over my
face so I was looking out through beautiful lace, and inhaling the heavenly
aroma of my mother's sex. I slept very well that night, with lots of
sexual fantasies flowing through my dreams!

I was released the next morning, and my soggy, pee-filled diaper was
removed. As I was being cleansed with the baby wipes, Mommy asked me which
name I was going by today. I told her I her Tammy today, and would either
be her big girl, or her baby girl, whatever Mommy wanted. I thought she
would split wide open, she was smiling so widely! I spent that day in a
cute little white and pink satin romper, a white satin bonnet trimmed in
pink lace, diapers and plastic panties. I was fed baby food, some warm
milk from a baby bottle, and some ice cream. Mommy seemed very happy to
have me just sitting in the room while she ironed, or cleaned, or watched
TV. That evening, around five or so, Mommy told me that I had been such a
good little girl, that it was time for a big reward. I was told to
upstairs and Mommy took of my wet diaper, and she cleaned me up. "I'm
going to make a very special meal for us, so little Tammy, dress up pretty
for dinner, and as soon as dinner is in the oven, Mommy will get dressed,

I thought hard about what dress to wear for Mommy. First, though, I
took a long hot bath, and washed my hair. While I was in the bath, I used
the razor and had removed all traces of hair from my legs, underarms, and
crotch. About a five minute task. I used the brush and hairdryer to make
it as nice as I could. Then it was into my bedroom, where I put the corset
around my waist, backwards, and laced it as tight as it would go. I think
I got it tighter than Mommy did. I thought that this would be easy, and I
could just spin the garment around, but it took almost twenty minutes of
struggling, puffing and panting to get the corset in the right position.
Now, I had to make the decision. As soon as I opened the closet door, I
knew. The choice of the white satin sissy dress with the pink ribbon trim
and wide pink sash was a no-brainer because that was the one Mommy gushed
over so much Christmas morning. That dress meant the frilly pink satin
sissy panties and the matching training bra along with the white nylon
sissy ankle socks with the cloud of pink lace at the top. I put on the
panties and bra, and realized that I liked the feel of the soft material,
the caress of the corset, and the look of pure femininity that I saw in the
mirror. I would love to see a few of the girls in my old school wearing
this outfit, and then take it off of them, slowly!
I then sat down at my little make-up table, and embarked on my first
attempt at nail polish. I don't think I did a bad job for a first timer,
but I have learned how to do it properly since then. While my pink polish
was drying, I decided to try a little lipstick. I put it on like I had
seen Mommy do, and how they did it in the movies. The first three times it
came out looking like clown paint. I finally found the right way to do it,
and now my lips matched my nails. I carefully pulled on the dress with its
built-in mass of crinolines, and then spent five minutes trying to get the
zipper up behind me. The sash was much easier, as it had a little snap on
each side to hook it to the dress. I undid the snaps, ties a big bow in
front, turned it to the back, and popped the two little silver snaps.
Done! Fluffing out my dress, I carefully bent over and pulled on the sissy
socks and then went looking for the right shoes. Okay, thanks to my tight
corset, I should have done that near the beginning, but I was just starting
to figure this girly dressing thing out! I decided that even though I was
dressed as a little girl, I had been a baby last night and wanted to grow
up a bit. I figured I would put on a pair of my new high heels. I had a
white patent leather pair with what looked like skinny, mile high heels,
but were really only 4 inches tall. These had a round toe and little
straps across the insteps, so they looked like high heeled Mary Jane shoes.
Perfect! I finally got them on and the little straps buckled, (which was
very hard with the tight corset) and stood up. I almost fell over, and had
to spend almost fifteen minutes just to get to the point where I could walk
around without looking like a cow on ice. Not graceful, just not falling

I hadn't really noticed the time, but just then I heard Mommy calling
up that she was already dressed, and dinner was on the table! I could
smell the food now. It had to be my favorite meal, steak! As I rushed to
leave the room, I stopped to grab what I hoped would be a finishing touch.
I had no jewelry, not even a girl's watch, but I had found a pair of poofy,
lacy wristlets in white satin with white lace, and a matching choker, so I
put them on, and hanging on the banister, slowly made my way down the
When I was almost at the bottom of the stairs, Mommy came out of the
dining room to yell up and tell me dinner was on the table. I don't know
which one of us gasped louder. Mommy was wearing a long, shimmering
silvery-white gown that hugged her body like a second skin. There was a
long slit up one side that allowed me to see her legs encased in shiny
white stockings, and a pair of silver high heels. She was wearing a simple
silver necklace that had a single blue sapphire that dangled just inside
the swell of her breasts. The gown had no straps over the shoulders, and
looked like it was staying in place by sheer magic. When she walked, she
seemed to float across the room, Her hair was done up in a French braid,
and her nails and lips were painted in a dusty rose color that seemed to
glow. As I barely navigated my way to the bottom of the stairs, we both
tried at the same time to tell each other how beautiful the other was, and
ended up in each other's arms, laughing.
       Dinner was broiled petite Fillet Mignon, asparagus, a small green
salad, and a bottle of vin rose wine. I hadn't ever had more than a sip of
wine before, but there was a full glass at my place. The Dining room
lights were off, and the room was lit by candles, making it seem a very
romantic setting, indeed. I don't remember much of what we talked about
while we ate. I was transfixed by this beautiful, sexy, sophisticated
woman at the table, and very, very conscious of my own frilly clothing, and
the raging hard on that was trying to tear through my satin sissy panties.
After dinner, I was a little tipsy, and Mommy picked up a lacy white apron
and tied it on me. It went over my shoulders and tied in the back, and
Mommy called it a pinafore, or a "pinny." At her request, I carried the
dishes out the kitchen, and put them in the dishwasher, the joined her in
the living room. She was sitting on the sofa, and patted the spot beside
her for me sit.

Mommy poured us each another glass of wine, finishing the bottle, and
we sat back and relaxed. She told me that my formal schooling was going to
start soon, but we would begin on the informal education tonight. She laid
out her plans for the rest of the year. Every morning would be intensive
school work, and every afternoon would be classes in home economics. I was
to learn how to cook, clean, do laundry, iron, balance a checkbook, do a
budget, shop for food, mend clothing, etc. In short, all the things a
woman has to do, or a man for that matter, if he is out on his own. All I
had to do, between now and the first day of school was decide if I was
going to enroll in the Mommy Home School as Mikey or Tammy. Mommy told me
to relax, and not to worry. As long as I made my decision in the next
three weeks.
After we finished our wine, informal classes got started. Mommy had
me stand and walk for her, giving me pointers on shortening my stride,
placing one foot in front of the other, etc., and soon, while not nearly as
graceful as she was, I was walking just fine in my new heels. I also
received instructions on how to sit, stand, and enter and exit a car in a
dress and heels. Every time I did it right, I got a very non-motherly hug
and kiss. I wondered if I would ever need to know these things, as I
wanted to go back to being Mike full time, and only play at being Tammy
every now and then. Still, I did enjoy the, shall we say, fringe benefits
of wearing dresses, and the lingerie felt good...I dropped this line of
thinking and concentrated on walking, sitting, and standing for Mommy. She
asked me if getting dressed tonight had been a problem, and got a good
laugh when I told her how hard it was to put on a corset by myself, and
told me that she would help me with that anytime I wanted.
After about 2 hours of being in heels, my feet and legs were on fire,
and I told Mommy that I needed to sit down and take off my shoes. She told
me that a good girl would wear her heels all day, but since I was so very
new to heels, we would go upstairs and make me feel better. I was told to
take the empty bottle and the two glasses out to the kitchen, wash and dry
the glasses and throw away the bottle. I was to start the dishwasher, make
sure the kitchen door was locked, and come upstairs. She told me that the
rest of my reward for being a very good girl was in her room, and it would
only take a few minutes to be ready. I went to the kitchen, and Mommy
glided toward the stairs in that beautiful gown,
It took me about fifteen minutes to finish up in the kitchen, and on
tired, aching feet, I made my way to Mommy's room. As much as me feet and
legs hurt, though, I noticed that walking in high heels was feeling pretty
natural. I looked in the hall mirror, and took stock of what I saw. My
legs looked pretty darn good in the heels, in fact, maybe with stockings;
they would look as good as that hot blonde in the adult magazine I had
hidden in the basement. Not as good as Mommy's, but still pretty damn
good. The whole little girly look, combined with the heels gave me a kind
of innocent look, like the girl next door, and that was sort of sexy. I
mean, with satin caressing my little cock, and the thought of Mommy's
delicious bottom in that dress, maybe anything would look sexy to me!
       Anyway I knocked on Mommy's door, and was told to come in with my
eyes closed. As soon as I stepped across the threshold, Mommy took me by
the shoulders, and gently moved me into the room. She closed the door, and
then put something soft over my eyes. "This is a satin sleep mask, and
it's just so you won't try to peek like a naughty little girl. With that,
I was sat on a soft cushioned chair, and Mommy told me to put my hands in
my lap and relax. She took off my heels and ankle socks, and began to rub
my left foot. Her thumb went round and round on the bottom, while her
fingers mad little circles on the top and my toes. I thought I would die,
right then and there, and die the happiest person on the planet! She
worked all the pain out of my left foot, and then went to work on my right.
After a long time, her hands began to massage my ankles, then my calves,
and finally my thighs, stopping well short of any sexual contact. She
helped me stand up, and told me that she was going to take my beautiful
dress off, and help me get changed into something more appropriate for the
evening's activities. Okay, I thought, here comes another nightie, maybe a
diaper. My dress went over my head, and I could hear it being hung up. My
corset was unlaced and removed, along with my training bra. My slippery
satin panties were pulled down my legs, and Mommy told me to pick up one
foot and then the other so she could take them off. I was now naked in
Mommy's room, except for my lacy choker, matching wristlets, and the sleep
mask, and wondered what was going to happen now. All sorts of sexual
thoughts were running through my head, and I could feel my rock hard cock
bounce in front of me.
       Mommy must have seen my little man, because just then she wrapped
one delicate hand around the shaft, and cupped my balls with the other. I
almost fell over from the palpable heat of her hands, and the electric
current that ran though my shaking, naked body. Mommy asked me if
remembered her putting on my first corset. I mean, how could I forget?
I've only worn one twice, and the first was just a few short days ago! I
told her I did, and she asked me if I minded wearing another one for our
little game. I was a bit confused, as she had just taken my corset off,
and now wanted to put it back on me. What the heck, though. I told her I
didn't mind being corseted again. She led me to the closet door again,
with one hand on my back, and the other holding my hard cock. I would have
followed that hand to Hell! She told me to reach up to the bar like first
time, and just like the first time, the cuffs were clicked onto my wrists.
As my mother stood behind me, I could feel the heat from her breast burn
into my back through whatever flimsy garment she wore, one of her hands was
still gently and slowly stroking my little man, while the other was
kneading and tweaking my little nipples. I started moaning, and trying to
hump her hand, and she just laughed and took her hands away. I began to
plead with her, and she told me to open my mouth, really wide. I did as I
was told, and something thick and rubbery was shoved into my mouth. As I
was trying to force it back out, Mommy was tightly buckling the straps
behind my head. She told me to run my tongue around the gag, and to feel
its shape. "It's a rubber penis gag, sweetheart. It will keep things fun
for a while." Fun for whom? I was starting to get scared, and tried to
tell her, but all that came out was something like "aaarugh, r-r-rar!"
Mommy then began to kiss the back of my neck, which started to calm me
down, and then began to kiss her way down my back, pausing to kiss both
cheeks of my fully exposed bottom. She then took a corset, and wrapped it
around me. Telling me to take a deep breath, she laced it tightly around
me. It was much tighter tonight that it had been either of the other two
times, and I tried to tell her it was too tight. She finally asked me to
nod if the corset was a bit too tight. I bobbed my head for all I was
worth. "Okay, my little princess, take a very deep breath and hold it, and
Mommy will fix." Gullible little me took the deep breath, and the corset
was pulled even tighter!
Mommy started to nibble on my ear, kiss my neck, and with both hands,
began to play with my nipples. I had found out from the adult magazine
that women had sensitive nipples, but I never knew until right then just
how sensitive mine were. I thought I was going to pass out from the
sensations caused by her lips and tongue on my neck, and her manicured
fingers on my nipples. She stopped, and I moaned into my gag, not wanting
any of this to stop! She told me that she was going to uncuff my hands,
and I was to place them behind my back. She undid one wrist, and quickly,
my hands were cuffed behind my back. Blindfolded, cuffed and gagged. I was
gently led to the bed, and told to sit down. She took one foot in her
hand, and then began rolling a stocking up my leg. The feel of that smooth
material against my shaved legs was amazing! She rolled the other stocking
up, and told me to stand up. She busied herself hooking the garters of the
corset to the stockings, and then told me to sit back down. She slipped
another pair panties up my legs, a pair of high heels onto my feet, and
fastened a strap around each ankle. My choker was removed, and another
choker was placed around my neck. This was felt heavier, and was a little
tighter. Mommy stood me back up, and helped me walk across the room as
these heels were skyscrapers, and they already hurt like hell! When she
took off my "blindfold" I was amazed at what I saw. I was looking into the
mirror, and saw that Mommy and I were both dressed alike, except my corset
was pink with black lace, and a pink, lacy choker, and Mommy was wearing
the same corset but in black with pink lace, and a black lace choker. My
stockings and heels were pink (with 6 or 7 inch heels!), and Mommy's were
black, and she wasn't wearing panties!
The very tight corset pushed some flesh up, giving me the illusion of
tiny breasts, but the effect on Mommy's small but beautiful breasts was, to
say the least, breathtaking! I wanted to suckle on those delicate, sweet
mounds thrust forward so brazenly. I wanted to kiss and suck on those
hard, delicious nipples, to do so for hours and hours, but I couldn't. I
was perched on heels so high that I could barely stand in them, let alone
walk, my hands were still cuffed behind me, and I was still tightly gagged.
Mommy came to me, and after kissing me on the forehead, began to suck on my
exposed nipples, and to lick and kiss my breasts. Her hands roamed over my
satin encased bottom, caressing my cock, and making me harder than I have
even been in my short little life. I kept trying to hump her hand, but she
just kept soft pressure, not enough to get me off, but more than enough to
keep me raging! The whole time this was going on, my body was screaming to
be released, and to be able to grab this sexy woman, to kiss her, to lick
her, and yes, to fuck her, while my mind was screaming just as loudly that
this was my mother!
Mommy had been whispering in my ear, and I hadn't noticed. She looked
me in the eyes, and asked me if she should stop. Without any conscious
thought, I wildly shook my head no, and tried without success to beg her
through my gag to keep going. She asked me if I wanted to cum, and again a
violent head motion, this time nodding hard enough to break my neck! Would
I be willing to be a very good girl, and let Mommy play before her "widdle
Tammy went cummies?" Again the violent nod. "Now sweetheart, what Mommy
wants to do may scare you, and will hurt some, but it will be so-o-o good
for Mommy, and the more you submit to Mommy, the happier she will be, and
the better your reward will be in the end. Now, on the other hand, if you
snap your widdle fingers together, three times, right now, Mommy will take
all that nasty stuff off of you, and tuck Mike into beddy-byes. Snap once
for Mommy to go on, and three times for Mommy to quit." I stood there,
raging hard-on in my panties (MY panties?) and then, slowly, snapped my
fingers, once.

Mommy clapped and giggled like a little girl, and then told me that
she had some questions for me, that I could answer by nodding my head yes,
or shaking no. "Are you ready for your questions?" Nod. "Do you love your
Mommy?" Nod, nod, nod. "Do you like dressing up as Tammy and wearing soft
silky things, and sleeping in your soft sissy bed?" Slow nod. "Do you want
to be Mommy's widdle sissy Tammy forever and ever, and to play with Mommy,
and to wear all the sissy, soft, silky, and lacy things Mommy wants you to
wear?" (mommy cheated with this one, as she had gone back to massaging my
stiffy, and I would have agreed to chop off a hand to keep that going on!)
I nodded again, and the questions were over. At least her questions were
done, mine were just beginning!

Mommy told me to relax because this will hurt, and I probably wouldn't
like it at first, but she loved me, and would do nothing to cause me any
real harm. If this was supposed to calm and reassure me, it had exactly
the opposite effect. Mommy busied herself at my back, and put another cuff
on each wrist. When she was done, she removed the steel handcuffs from my
wrists. She told me to hold my hands up to my mouth to allow the blood to
flow, and when I did, she took first one, and the then other, and hooked
the leather cuffs she had placed on to the, what I now saw was a lace
trimmed, leather choker around my neck. She then led me, teetering on
those god-awful, ultra-high heels to the foot of the bed. Now, Mommy is a
very feminine lady, and likes very feminine things. One of her feminine
goodies was her bed, which was a beautiful 4 poster of polished cherry,
with a light maple oval inset on the footboard, itself set with inlayed
pieces of wood to make a floral arrangement. It was to this footboard that
I was led.
Mommy started to place me against the footboard, facing the bed, and
then, almost as an afterthought, turned me around, and unbuckled the gag
from my mouth. I started to ask her what was going on, and she shushed me,
grabbed my shoulders, and began to kiss me deeply. After a few breathless
minutes, she stepped back, and began to talk in a quiet, but serious voice.

"Honey, I know you're very confused, and very horny right now, and I
wanted to explain things before this all got too far out of control. You
see, I hated your father, and still hate him for what he did to me, to us.
You see, my darling little princess, when we started dating, your father
was a very loving and gentle man. He practically waited on me hand and
foot. I was a virgin, and didn't want to have sex until my wedding night.
I had so many dreams about wearing a beautiful silk wedding gown, and my
new husband would take us to an elegant hotel. Once there, he would
lovingly remove my gown, and attired in just my white silk undergarments,
he would make beautiful love to me. What happened was a little more
pedestrian. We had pizza one night with a bottle of wine, I got tipsy, and
we ended up in bed. That was the first time we had sex, and I got
pregnant. Well, he did the "honorable thing" and married me. After we got
married, I realized that all the love, devotion, and attention he had
lavished on me was designed merely to get into my panties. Very shortly
after the wedding, he almost ignored me. After a few months of my
pregnancy, he started running to hookers, or to any female who wasn't
pregnant like me to get his kicks. Even on our honeymoon, when I wanted
him so badly, he didn't want to touch me. I wanted to have sex with your
father, but he had changed after the pregnancy and wedding, and for the
worse. I started hating all men after that, and soon, not only wouldn't
allow your father to touch me, I wouldn't even let him sleep in the same
bed with me."

"Honey, I'm so terribly sorry to say, I even hated you at first
for being a boy. (she started to cry a bit, and had to take a moment to
wipe her eyes, and get her emotions under control) When you started to
dress up, and play little girl, I thought that I wanted a girl, not a boy.
Now, I don't want a girl at all, I just want you. But, and this is a
serious but, I don't want to raise a man who thinks he can do whatever he
wants, with anyone he chooses. If you agree to go along with the program,
you will live with me as my Tammy, my little Tammy. I will be in charge,
and you will do what I tell you. You will learn submission to Mommy, and
to any woman, or man, you live with. (that caused me to jump!) You will
start your home schooling as Tammy, and be trained to be an obedient little
girl. I even wanted, at first, to take you to the doctor, and make you a
girl all the way ( I gasped at this and began to argue, but she kissed me
again, and told me to relax.) That isn't going to happen, because that
would make you very unhappy, and that in turn would make me unhappy. So
tonight, you are going to take the first steps to submission, and Mommy
will train to you be, not a girl, but a sissy. That's right, a sissy who
obeys a woman, a sissy who is soft and gentle, thinks of his mistress's or
master's needs first, and her own needs later. You will learn how to make
love to a woman the way another woman might, and put your need to cum, your
very need for sex as a man, a distant second. I have been planning this
for a very long time, and while you really don't have a choice in the
matter now, come summer, if you want to go back to being a boy full time,
we'll talk about it then. For right now, and for the near future, you will
dress like a girly sissy, act like a girly sissy, and Mommy will teach you
to make love like a girly sissy, to women and to men, is that all very
clear?" I gulped hard, trying to make sense of what she had just told me.
I looked at this beautiful woman standing in front of me, and thought very
hard. I wanted her to be happy, I wanted to be loved, and petted, and yes,
I wanted to cum very badly! My cock was leading me into a lacy, sissy
world, only dimly perceived
"Mommy," I whispered, "I don't know what is going on, not really,
but I like being Tammy, especially if it will make you happy. I think the
happiest I have been is when I have been your special princess, and if you
will teach me, I will be the best princess any Mommy could ask for." With
that, she was kissing me again, and crying hard. She told me that I would
always be her special princess, and that she would make sure that I was
well rewarded for learning my lessons like a good little sissy. With that,
she kissed me again, and told me to be a brave little sissy, and redid my
pink lipstick. Then, she gently put the thick penis gag into her pussy,
and then placed that heavenly tasting, but nasty thing back in my mouth.
She turned me around so I was facing the bed again, and, bent down behind
me. She took my left ankle, and hooked a cuff to it, and then my right
one. These cuffs were attached to ropes that went to the legs of the bed,
and when she pulled them tight, I was forced to spread my legs, very wide.
As she was standing back up, she took a moment to plant a kiss on each butt
cheek, She then took another length of cord with a hook on the end, and
attached it to my collar. I had figured out that this was no ordinary
collar, it was a thick pink, leather collar with lace attached, and had
sturdy D rings embedded in it for just this use.

She then took out a digital camera, and took several pictures of
me. She showed me the camera screen, and I could see myself, spread
legged, dressed in my tight corset, my hands at my neck, my pink lips
stretched around the rubber cock gag, and the ultra high heels on my feet.
She showed me a close-up picture of my face, with those shiny pink lips
wrapped around the black cock-shaped gag, and finally showed me a picture
of my bottom. I could see the full cut, pink satin panties, trimmed in
black lace like my corset, and I could see a hole on the backside, trimmed
in more black lace. The hole was right over my, over my, OH GOD, it was
right over my little asshole! My bottom was covered in satin, except for
the one spot that should be covered, which meant...
Now, Mommy tightened the rope hooked to my collar, forcing my head
down. She took a satin coverlet, and placed it between my knees and the
wooden footboard, and then pulled my head all the way down to the
bedspread,placing one of the thick cloth diapers between my face and the
satin bedspread, I suppose to sop up my drool. I was trapped against the
bed, my poor bottom up in the air, and I was very, very scared. I felt
Mommy's finger touch my virgin hole, and tried to suck in a deep breath.
Her finger was coated in some kind of lube, and she pushed it up into me.
It wasn't too bad, so I relaxed a bit. She pushed the finger in and out of
me, and with my satin covered hard-on pushing against the coverlet, and her
finger stroking in and out of me, I almost came on the spot! Now, she
pulled her finger out, and told me it was time to be a brave little sissy
I felt something hard against my bottom, and she began to push what
she told me was a butt plug into me. I screamed and yelled around the gag,
drooling on the diaper, and tried to twist away, but with no luck. The
pain grew into fiery agony, as she pushed the plug farther and farther into
my poor stretched hole. Finally, with a grunt from Mommy, and a scream
from me, it went the whole way in. Mommy then proceeded to use her hand to
spank my bottom as hard as she could. I was screaming, tears and nose
running, and wishing I was anywhere other than here! But, through it all,
my cock not only didn't go soft, if anything it got harder! When she was
finished spanking me, she told me that I must stay like this for a while,
and she put on a sheer peignoir, and left the room. My mind was in a
whirl, and my backside was in terrible, burning pain. What the hell was
going on?
I just stood there, as though I could do anything else, with my
legs spread, my wrists firmly locked to my collar, and my head pulled down
to the bed. My mind was going twenty directions at once! I did notice,
though, that the burning sensation in my bottom had gone away, to be
replaced by the feeling that I had to go to the bathroom, badly. I tried
to push as hard as I could to expel that terrible plug, but could not. My
backside still stung from the spanking, but through a pair of double layer
satin panties, and with Mommy's bare hand, I really hadn't been spanked all
that hard. It was just the sudden unexpectedness of the whole thing that
made it seem so bad, I guess.

I started thinking about me being a girl for the next few months,
at least, and was surprised that the thought didn't upset me as much as I
thought it would. I mean, I would be here at home, no one would see me,
and it did mean getting away from that stupid public school, their lame
lessons, and those horrible students who always picked on me. I began to
relax a bit, and found that the more I did, the better things became. My
feet and calves were burning, and my legs trembled terribly, but since I
couldn't do anything about that, I tried to forget it. Instead, I
concentrated on Mommy's passionate kiss, and the promise of more "rewards."
About that time, Mommy came back in, and telling me to relax, she
stood behind me. I was afraid of another spanking, but instead, Mommy
began to caress my bottom, and my thighs, running her hands up and down my
silky stockings, cooing about how pretty her little princess was, and how
brave she was being. Mommy told me the lube she used was called Anal Eze,
and it had some sort of anesthetic in it to make things hurt less. She
hoped it was working. I tried to reassure her that it was, but could only
mumble around the thick gag in my mouth. Mommy told me that she was going
to pull the plug out of my bottom, and it would hurt me again, so just
relax and it would all be over in a moment. I nodded and mumbled, and felt
her hands fumble at my bottom. With a steady hard tug, she pulled that
monster from my backside, causing me to scream again into the gag, even
though it didn't seem to hurt as much as it did going in.

Mommy then took the plug into the bathroom, and came back out and
wiped my still gaping butt hole with a couple of baby wipes, She then began
to unhook my head, and then my legs, leaving me still gagged, and standing
on shaking legs and 6 inch-plus heels. She led me to the bed, and helped
me to sit down. I thought she was going to take the heels off, but she
pulled something from under the bed, and hooked it to the cuffs still on my
ankles. "This is a spreader bar, baby, she said, and it will keep your
legs apart for a while longer." I wondered what horrible new game we were
playing. She then took a short piece of chain, with a hook on each end,
and clipped my wrist cuffs together, and then unhooked them from the
collar. I was pushed back on the bed, and Mommy swung my legs around so I
was laying full length on the bed. She took my cuffed wrists, and pulled
them to headboard and secured them, leaving me spread eagled on the bed.
Only now did she pull the gag from my mouth. I worked my jaw around, to
ease the ache, and ran my tongue over my painted lips.
Without a word, Mommy swung herself up on the bed, and sat
squarely above my face. She lowered her sopping wet pussy onto my mouth,
and without any instructions, I began to lick and kiss her sweet mound,
trying to remember all the hints she had given me the last time. Slowly she
ground her musky sex into my mouth, and finally gave a loud gasp, began to
tremble and buck. She raised herself up for a moment, allowing me get some
breath back in me, and then, she pushed that wonderful pussy back down on
my face. I was gagged again, but this time I loved it! She was like a
woman possessed, and was moaning and bucking on my mouth, my tongue trying
to find that one spot Mommy told me about. I must have found it and done
well, because my mouth was once again filled with her orgasm, and as
uncomfortable as I was, as much as my jaw and tongue ached, I wanted more!
But, breathing heavily, she rolled off of me, and lay beside me, panting,
her beautiful breasts heaving.
"Now, my little princess, you've had your lesson for tonight, and
Mommy has had her little treat, now it's time for Tammy's reward!" With
that, she removed my panties, which had a row of snaps down each side, and
pulled them away from my body. She leaned over and began to lick my stiff
member, blowing on it, and doing everything but what I wanted, which was to
take it in her painted lips, and make me cum. I was moaning and trashing
around, trying to buck my hips up to make her take me, and every time I
did, she would giggle and lick my hairless balls, and kiss her way up the
shaft, causing me horrible, wonderful distress. Finally, she leaned away,
and stood up. The sheer peignoir slid to the floor, and my mother, my own
sweet Mommy, climbed up on me, and sank her sweet, sticky sex over my cock!

I began to wildly hump up, but was told to lie still like a good
girl. She started to lick my nipples, gently biting them, and then began
to ride my young cock. Faster and faster she went, and we were both
moaning to beat the band. I could feel my balls tighten, and I let loose a
load of boy cum into my mother. At the same time, she let loose a loud
moan, and pushed down as hard as she could. We lay there, sweating and
panting for a few seconds, and then she moved up on me, and told me to be a
good girl and clean Mommy out. I licked and kissed, swirling my tongue
into her sweet pussy, tasting our combined cum, until Mommy had a third
orgasm, and rolled off of me, and lay beside me. I wanted to cuddle her,
but since I was restrained, the most I could do was lean my head over and
kiss her hair. This was better than any magazine or fantasy! I had just
been fucked by my mother! I just, well kind of, fucked my very own mother!
My mother had bound me in lingerie, ravaged my bottom, had forced me to eat
her, twice, and now she had fucked me! I was conflicted, but I loved it!!

I was finally released from my bondage, and those heels taken off
my feet. Mommy helped me off with the corset, and told me to go in to the
bathroom and run a nice hot bath for Mommy. She handed me my pink satin
robe and ballet slippers, and told me that after Mommy had a bath, I could
take one. I asked if I should just take a shower, but was told that little
girls took baths, only yucky boys took showers. I ran her tub, and added
some bath oil, and that at her request, went to the kitchen and brought her
something to drink. About a half hour later, we had both bathed, and were
seated in the kitchen. I was wearing a pink satin baby doll nightie and my
white high heeled mules on my tired aching feet, and Mommy was wearing a
very sexy white silk teddy, sheer bed jacket, and silver mules. Mommy had
poured us each a glass of sherry, and told me that we needed to have a
little Mommy / Daughter talk.

After an hour of talking, listening, some yelling, and bit of
crying (from both of us) we had things sort of sorted out, at least for
now, and Mommy told me it was time to go beddy-byes. She then asked a
curious question: Where did I want to sleep, and how/wearing what? What do
you mean Mommy? "Well," she said, "You have a choice to make. But, while
each choice has an upside, there is also a "payment" to be made for each
choice. You can sleep as Mikey in your old bed, and in your old PJs.
That's your first choice. If you do, it will mean being tied down, and a
good, hard spanking with the hairbrush on your bare backside as "payment."
You can sleep as baby Tammy, and wear your diaper, but you will be put in
bondage for the night, and will have to stay in your diapers and plastic
panties all day tomorrow, even when we go out, and we are going out. You
will wear a very short skirt and blouse, diapers, and the noisiest plastic
panties I can find. Your final choice is to sleep as Tammy, with Mommy in
her bed, but you must wear your butt plug, all night." I thought for all
of three seconds and took option 3 in a flash! A few minutes later we were
in Mommy's bathroom. I just thought that this was the place she was going
to put that horrible thing into me. I was wrong, as usual. Mommy told me
to take off my beautiful nightie, and lean over the tub, with my hands on
the side. I did, and while I waited, Mommy filled what looked like a hot
water bottle with warm water, and something out of a bottle. When the bag
was full, she attached a hose to it and came over to me. "This is an
enema, my little angel, and it will clean you out so you don't have to go
to the potty tonight, and that nasty plug won't have to come out and be put
back in. She put some lube on her finger, and gently eased it into my
backside, and then just as gently, inserted the nozzle of the enema.
Telling me that I would feel very full, and might start to cramp up, she
opened the valve, and began filling my backside. I have to tell you that I
loved the feeling of the foreign object in my bum, and the feeling of the
warm liquid flowing into me. She emptied the bag, and now I felt very,
very full, and wanted to sit on the toilet very badly. Mommy told me that
I had to hold it for a few minutes, and set a small egg timer. "As soon as
the sand runs out, sit on the toilet and push hard to get all the yucky out
of you," she told me. It was a very long 3 minutes, but the end finally
came, and I sat down, and emptied myself in a long smelly rush. I was told
to lean back over the tub, and Mommy cleaned me up with a warm washcloth,
and then it was back into the bedroom.

Mommy asked me if I needed to be tied up and gagged for her to get
the plug back in, and I told her that maybe I needed some help. Smiling,
she told me to open my mouth, and put my gag back in. My hands were cuffed
behind my back, and my ankles were locked into the spreader bar. Mommy
then pulled up a chair, and pushed my down so I was across her lap. She
lubed my little hole, and with a warning that it was coming, began to force
that rubber monster up inside of me again. I hurt a lot, but it didn't
seem as bad as last time. When it was in place, Mommy stood me back up and
began to laugh. My little cock was sticking straight out, and I had left a
trail of pre-cum on Mommy's bare leg.

"Hmm," Mommy said, "You seem to like all this attention to your
bottom, don't you, my little sissy? Is it the bondage that you love?
Maybe it's being across Mommy's lap, or a combination that does it. Well,
little Tammy, I can't have you leaking your boy juice in my pretty bed,
so...? She looked around the room, and suddenly a light came on. She left
the room, and was back in a moment with a diaper, diaper pins, and a pair
of plastic lined satin panties. Still in bondage, she lay me down, and
tightly pinned the diaper in place, after putting what she called a doubler
pad in the middle. With that, I could not close my legs without a lot of
effort. The plastic lined satin panties were slid into place as soon as my
leg spreader was removed. I was then stood up, my hands released, and my
gag taken out. Mommy slid my baby doll nightie over my head, chuckled a
bit, and went back out. She was back in a moment with a pink satin bonnet,
satin booties, and my fingerless satin mittens. She tied the mittens onto
my hands, booties on my feet, and the bonnet on my head. "I hope you don't
mind, but you look so darn cute like this!" I assured her that this was
fine, but the only thing that bothered me was the fact that my cock was
tucked away under what seemed like miles of fabric, and he wanted some more
attention. As it was, we slid between the pale blue satin sheets, did a
little cuddling and kissing, and as we were both worn out, sleep came
quickly for both of us. The last thing I remember was thinking that the
plug didn't hurt at all, and kinda felt good, somehow.

When I woke up the next morning, I was cuddled against Mommy, and
her arm was wrapped around me. I felt very warm, safe and snuggly. I
felt, I realized, like a little baby whose total happiness is derived from
its mother. I sighed, and snuggled a bit closer. Soon, though, I had to
pee, and pee badly. My diapered front was pushed against Mommy's leg, and
I was sure that she would wake up, and maybe even get upset that I was
peeing my diaper n her bed. I slowly started to disengage myself from her
warm, sweet-smelling body, when all of a sudden Mommy rolled over and
smiled at me. She rolled on top of me, and asked if her widdle baby-kins
needed to go potty. I assured her I really, really did! "Well, you're
dressed like a widdle baby, and you're wearing a widdle baby's diaper, and
cutesy-wootsey plastic panties, so why doesn't my widdle baby go pee-pee.
I was embarrassed, no actually humiliated, and yes, turned on by it all. I
finally gave in to the inevitable with a big sigh, and began to fill the
diaper with warm pee. When I was done, Mommy did a strange thing, and
stuck her hand down the front of my diaper, and then brought it out and
licked the pee off her fingers! I wasn't grossed out, but wow!

We got out of bed, and Mommy let me out of my mittens, and told me
to go to my room. As I sat on the plastic sheet on the bed, Mommy asked me
if liked being treated like a baby girl. I told her about how special,
safe, and warm I felt, and Mommy just laughed. "Well," she giggled, "I
guess we had better get the stuff out of the garage and set it up. I left
it there because I thought it was a little too much for you to handle at
first." I was left wondering for a while, while she removed my soggy
diaper, and then pulled the plug out of my bottom. It only hurt just a
little bit, and when I told Mommy, she said that maybe I was ready for a
big girl's toy next. Again, I was left wondering.

A short time later, we were both bathed and dressed. Mom was
wearing pair of slacks and a pink sweater, but I was in a short, pink and
blue tartan skirt of some soft synthetic material, White nylon knee socks,
and a white satin blouse, though which my lacy white satin training bra
could be very clearly seen. Of course, the skirt was short enough that if
I bent over from the waist, my white satin sissy panties were on display.
I was allowed to wear a pair of flat soled, black patent Mary Janes, as my
feet and legs were still tender from the last evening. We spent the
morning dusting, vacuuming, making the bed, and tidying up. After lunch,
we made several trips to the garage, bringing up some very heavy boxes to
my new room. Mommy told me to wait in her room, as this was going to be a
surprise. She led me back into her room and told me to put the handcuffs
on my own wrists, which I did. She then took my hands, and attached a
short leather strap with a hook to the cuff chain, and then onto a hook in
the wall, over my head. When she was done, she began to kiss my face and
my gently rub my little cock through my panties. Giggling at the reaction,
she asked me if I wanted what was in hamper number one, or in hamper number
two. I had no idea what she was asking, but guessed, "Uh, number two,
please?" She told me that first, just for fun, she wanted to gag me again,
and put the thick rubber penis gag into my mouth, and buckled it. She
popped into the bathroom and returned with a pair of her soiled panties,
which she placed over my head, with the fragrant gusset at my nose. Mommy
giggled again and said, "I guess it's a good thing you chose number two, my
little damsel in distress, number one would have been your very own pissy
diaper over your head!" She went off to my room, laughing, leaving me
wondering, not for the first, or last time, what the heck was going on.

I heard lots of banging and noise from my girly room, and within a
very short period of time, Mommy was back, pulling her panties off my head,
and took off the cuffs. Since I had been wearing shoes with only a
half-inch heel, and my arms were just above my head, I had suffered no
discomfort. My gag was removed, and I was kissed again, and then Mommy
stood back and looked me over. She just smiled, and took my hand, leading
me into my room. Right under the window there was now a large, and I do
mean large, white baby's crib! There was something against the other wall,
but I just could not take my eyes off of the crib. Mommy led me over, and
told me crawl up into my baby bed. I did, and she showed me how the side
slid up, and then folded a barred cover over the top, locking me into the
infantile prison. It was big enough for me to stretch out in, and the
vinyl pad seemed fairly comfy, but still! Mommy unlocked the top, and
dropped the side, and helped me out, and took me over to show me the other
new piece of furniture. This was nothing less than an oversized baby's
changing table, with shelves under it filled with diapers, pins, baby
powder, and my plastic panties. My mother had gone to extreme lengths over
the last few weeks, and I wondered what else she had in store for little
ol' me!

Without taking any time to play, We went downstairs, and Mommy
handed me the cutest rabbit fur jacket, matching hat, and a muff, and out
the door we went. Our first stop was a beauty parlor in a nice lady's
house. Mommy had her style my long hair into a layered girl's style, and
even I thought it looked pretty. This was a little over the top, I
thought, I mean, no guy has this kind of hair style, but I wasn't too
worried. I mean, hair does grow back, right? If I wanted to be Mike again
tomorrow, I could just get a crew cut, and be done with it. What did
bother me was the nice lady fussing over my "beautiful frilly panties and
my sweet sissy bra!" Okay, the lady might gush over a little girl's
clothing, but I wasn't a little girl! After my hair was done, Mommy made
me curtsey to the lady, and then they both held my skirt up and admired my
panties! I know that my cock, while not huge, was plainly visible through
the material! After we left the beauty parlor, it was off to the mall,
just a short drive of 25 minutes away. I was self-conscious of how I
looked, but I had looked in the full length mirror at the salon, and knew I
looked just like a 12 year old girl. Even though I was dressed more like a
girl from the 50s or early 60s and might get stares, still I looked nothing
like a boy dressed up like a girl. I wasn't sure if the thought comforted
me, or scared the hell out of me!

Once in the mall, we went straight to a store called Claire's where
Mommy had my ears pierced, and two cute little solid gold teddy bears
inserted. We also bought a few other pairs for when my ears healed. Then,
it was on to the nail salon, where my nails were trimmed, buffed, and
repainted in pink. Mommy told me that young girls don't need fake nails,
and I would get them when I got to be a little older, and started dating
boys. I blushed hard at that, and wondered just how far this was supposed
to go!

Victoria's secret was next for a few sets of lingerie. A set, I
found out, was a pair of panties, matching bra, garter belt and often a
camisole. I also learned that my bra size was a 34 A, at least for now
Mommy said. These were very glamorous garments, suitable for a beautiful
lady, and Mommy made sure to twist the knife in me by telling me in front
of the clerk, "Now I know a little sissy shouldn't wear such sexy things,
but if you go out on a date with some nice boy, you might need them, so
we'll get them now." Then it was on to a nice store where Mommy bought me
what she called a cocktail dress in black, and a long gown in pale green,
both on sale. A pair of grown-up style black pumps, and a pair of strappy
white heels completed our shopping. In the car, Mommy told me that the
dresses and shoes were to help teach me how to dress like a lady, how to
get in and out of a car, and so I could learn to dance in a long gown. I
was really worried now! Just how far did she expect me to go, and how far
did I want to go?

"School" finally started, and I while I was told, ordered really,
to wear the prissiest, sissiest little girly dresses, with lacy satin
underthings, Mommy, or Teacher, always wore a white satin blouse, black
skirt (sometimes leather) black stockings and heels. (I know exactly what
she wore, as I hand washed all of her satin and intimate garments every
night!) I spent Mondays learning math all morning, Tuesdays were English,
grammar, and literature, Wednesdays were history and geography, Thursdays
were Science and health, and Fridays were phys Ed. Fridays were the worst.
Phys Ed was a two hour private ballet lesson, with me usually in pink
leotards and a tutu, followed by aching legs and sore feet, and a shower in
the dressing room at the studio. This was then followed by a two hour
ballroom dancing lesson, with me wearing either the black cocktail gown, or
the green evening gown, high heels, and stockings. Of course, I was not
taught to lead! Every afternoon, Mommy had the devious idea that I should
not only learn to keep house for myself, but for others, and was therefore
required to wear a black satin French Maid's outfit, complete with the
frilly panties, corset, hose and heels. I would have little lacy cuffs on
my wrists, a lacy choker around my throat, and a little lacy maid cap
perched on my head. Mommy was addressed as "Ma'am," and every command was
to be answered by "Yes, Ma'am," and a curtsey. Okay, I have to admit that
I was learning to love wearing lingerie and dresses.
Was I gay? I really didn't think about it, but I loved it when my
dance instructor complimented me as a "talented young lady," or when I got
stared at in the mall, or a guy whistled. At home, I learned not only to
cook, clean, hand wash lingerie, iron and do laundry, but how to do Mommy's
nails, give a manicure and a pedicure, and how to be a perfect maid to a
woman. Most nights I was locked into my crib wearing my diaper and a
pretty nightie, although some nights, when I had been a very good girl, I
slept in my big girl bed. Both of these options also involved Mommy
turning on a cassette player, and playing a tape of nature sounds to help
me sleep. I found out much later about the hypnosis elements embedded in
the tapes. Suggestions such as, "It's okay to pee in diapers," and "I love
wearing panties," were droning in my ears all night. Doing really well on
a test, or some other great goal attainment, might even result in me
sleeping in Mommy's bed, although I didn't get much sleep! Rewards and
punishments were dished out daily.

Wrong answers on a test, or failure at the dance studio to master a
step or exercise, or any misstep in my maid's duties were met with bondage
and pain. Mommy used punishment heels to discipline me with. The first
pair were the ones I had to wear the night I learned what a butt plug was,
and had at least 6 inch stiletto heels that perched me up on my toes, and
that really hurt! She then bought me a new pair which were higher, and the
way they were made I ended up on my toes like some demented ballerina! I
would have to stand in the corner, gagged, with a plug in my bottom, and my
hands cuffed behind my back, in one pair or the other of these horrid
shoes. Of course, with latter pair, I would usually be put into a full
tutu skirt and a little matching lace cap-like thing in my hair. I was
spanked, and one night, made to stand on the front porch in the cold like
this, in just my corset, panties, and bondage things, where I prayed that
no one would come up, and trigger the motion detector light!

Rewards, though, were as nice at the punishments were bad. I would
be allowed to spend hours kissing and licking Mommy, and making her cum. I
would still be wearing lingerie, but Mommy would sometimes even let me make
love to her, almost like a man!

It was a rainy Saturday in early April, while we were sitting
together on the sofa, that Mommy told me that I had a date coming up soon.
"A date?" was all I managed to croak out. "Yes, my little princess, a real
live date with a boy! In fact, you'll be going to the Senior Prom at a
nearby high school!" I began to sputter and choke out questions, and Mommy
just put her arm around me, and half turned to face me. "Sweetheart, are
you still conflicted about who and what you are?" she asked gently. I
nodded, as I was still a bit dazed from the announcement. "Well, this date
should help you see things a little more clearly. You will get dressed up
as a beautiful young lady, go to a dance with a young man, and afterwards,
you should have a much better idea of who you want to be! If you like
being a girl, well, then, you can stay as Tammy for the rest of your life.
You can even opt for surgery to make you a real little girl, but only if
you want it. Of course, if you find, at the end of the evening, that Tammy
should be banished from Mike's life, or even if she should be relegated to
a part-time status, well then, so be it! You see, I told you that you
could make the decision at the end of the school year, and so you shall!"

The prom date was with a distant cousin of mine, whom I vaguely
remembered meeting many years ago. I was shown a recent picture, and he
was quite a good looking boy. Mommy informed me that his family had moved
to another state with his father's job, and had just moved back about a
month ago, and so he had no girlfriend to take to the Senior Prom. That
was where I was to come in! We discussed it almost every day, and slowly
but surely, Mommy wore down my resistance. It was to be a school almost 50
miles away, and I knew no one there, and more importantly, no one there
knew Mike, let alone Tammy! Finally, towards the end of the month, I gave
in, and asked Mommy when we would start shopping for my Prom gown!

Shopping for a prom gown must be like a lady buying a wedding
dress! We went into the city, and hit at least a dozen stores, trying on
dozens of dresses, ranging from inexpensive, to well over a thousand
dollars! We finally settled on a style, if not the dress itself. It
should be sort of a Southern Belle style, or maybe something from the
fifties, but no sexy red or black. No sophisticated,
slit-up-the-side-of-the-skirt, figure hugging, slinky black dress for this
sissy! I wanted to cover as much of me as possible, as I didn't want my
date to think I was there for sex, and Mommy still wanted a touch of the
sissy in the dress. After many hours, we ended up at a very nice boutique
where Mommy seemed to know the owner, and there we finally found what we
both agreed was the perfect dress. It was peach colored satin, with a
spaghetti strap neckline and a tight bodice, sweeping into a flared, full
length skirt. The dress fit tightly across my chest and stomach. The bust
of the dress had lace overlay with some little seed pearls. It was a
beautiful gown, that looked like something a movie star of the late fifties
would wear, but it would need a few alterations, especially as I didn't
have the bust of a 1950s movie star! To go with my new dress, the
manageress and Mommy picked out some new lingerie for me to wear.

I was helped off with the dress, so the lady could take some
measurements. Both the nice lady and Mommy noticed my little cockette
standing at attention in my panties. "You should either put him in a
chastity device of a heavy gaff if he is going to react to lingerie in this
manner," the manageress said matter-of-factly. Mommy looked at her, and
then at me, and told her that she had bought something called a CB 3000,
but hadn't used it yet. "This seems like the time, doesn't it? The lady
answered. Mommy sighed, and said, "Yes, I suppose I will have to the
moment we get home." I didn't know what it was, but I was sure I wouldn't
like it. I had another unpleasant shock, when the lady measured my chest
and told Mommy that the hormones were working well, and that I now had
perfect B cup breasts. HORMONES??? Was that why my breasts seemed to be
more sensitive lately? I thought maybe the ballet had developed different
muscles or something. I mean, I had noticed that while I lost a lot of
weight, my chest hadn't shrunk like my waist. I knew my breasts were
getting bigger, but really had tried to ignore them, as it scared the heck
out of me! Was that the hormones? Oh shit! The saleslady left and came
back with my new lingerie we were buying for my dress. There was a
matching garter belt and panties, and a camisole, all in delicate ivory
silk with lace trim. I tried them on, blushing as I pulled off my sissy
panties, and put these wonderful, sophisticated panties on. Both women
looked at me for a bit, and then the Manageress told Mommy she had just the
bra. After telling me to take of my pretty cami, she left for a moment,
and came back with a push-up, demi-bra that matched the rest of the
lingerie. She wrapped the bra around my chest, and adjusted the straps.
My little nipples were just barely covered by the thin bra. My cami was
slipped back on, and they told me to hold my arms up as the dress was put
back on, and zipped up. I looked in the mirror and saw a girl, with
breasts, looking back at me! I was horrified, and yet thrilled. I
couldn't stop looking at the feminine sissy that was looking back at me! I
was in a confused heaven as she marked and pinned my gown.

Reluctantly, I removed my new finery, and got dressed in my skirt,
blouse, and underwear that I had worn to the store, and we went to a shoe
store to buy me a pair of white, high heeled pumps. They had five inch
heels, and an ankle strap. Mommy bought one more thing, and that was a
pair of real white silk stockings, that had a seam up the back, and lacy
tops. I couldn't wait to wear them! After that it was home, to whatever a
CB3000 was.

Once home, I was surprised to see a couple of men in the house,
sitting in the kitchen drinking coffee. When we entered, they stood up, and
the older man told Mommy that the work was done, and asked her if she
wanted to inspect it. She told me to wait in the kitchen with the younger
man, and the two went upstairs. The other man just looked me over, in sort
of a hungry manner, and asked me if the room was for me, or what. I had no
idea what he was talking about, and he just laughed. He got up to put his
mug in the sink, and as he passed me, he grabbed my ass and told me that if
I ever needed a man in my life, he was ready to oblige. I jumped out of my
skin, but my ass burned where he grabbed me, and my cock was twitching hard
in my panties. I didn't know why I reacted like that, but I felt as though
I was torn in two for a moment, one half loving the attention, and the
other disgusted by it.

I didn't have time to dwell on the situation for more than a
moment, as Mommy came down, paid the men, and thanked them. The younger
man blew me a kiss as he was leaving, and gave both of us a very frank
look-over that left very little of what he was thinking to the imagination!
With them gone, Mommy told me to go to my room, and get undressed, all the
way undressed. As I got to the top of the stairs, I could smell latex
paint, and when I got to my room, the crib and changing table were gone. I
wondered about that for a moment, and then got undressed, hanging my skirt
and blouse up, and putting the rest of my things in the hamper. Mommy came
in and told me to hold out my hands. She then put my fingerless pink satin
mittens on my hands, and then told me to open my mouth. The thick rubber
cock gag was placed in my mouth, and it was buckled behind my head. My
pink satin baby bonnet was tied on, and a pair of matching baby booties
were placed on me feet. Otherwise naked, I was led down the hall to my old
room. When the door was opened, all I could do was just stare and drool
around my gag. My old bedroom had been turned into the sissiest nursery
ever! The walls were pastel pink, white lacy curtains at the window, my
huge white crib and changing table had been moved in, and were now adorned
with decals of cute pink bunnies and teddy bears, and now there was a white
rocking chair! There was even an oversized baby's high chair in the

Mommy didn't leave me much time to explore, as I was told to climb
up into my widdle cwib, and lay on my back. Once in position, Mommy hooked
cuffs to my ankles and wrists, and then secured me to the corners of the
crib. I hoped that whatever was coming was less horrible than my
imagination. I hoped in vain. Mommy went downstairs, and returned with a
basin. She set it on the changing table, and pulled out a plastic bag that
had something in it, and was dripping. She carried it over and pressed it
on my cock and balls. OH MY GOD did it hurt! The bag was full of ice, and
I thought I would die from having my balls frozen! After a minute, she
removed the bag, and picked up a small box. Taking something out, she
showed me a small pink plastic collar. She bent down, and did something to
my numb balls. She then showed me a small, pink plastic tube. Again, she
began to fumble around my crotch, and I could feel myself being pushed and
pulled, but could not really feel anything because I was still numb. When
she was done, she reached back into the box, and brought out a little
silver lock, bent down, and I heard the snick as it closed. Now, Mommy
cupped my balls, and began to blow her warm sweet breath on my crotch.
Feeling returned, but what an odd feeling. I was getting hard, but it
hurt! Mommy giggled, and brought over a mirror. With horror, I could see
my cock trapped in a translucent pink plastic tube, with an opening to pee
through, and a lock holding it to a collar behind my balls! I wanted this
thing off, and off NOW!

Mommy began to stroke me, paying attention to my sensitive nipples,
and my exposed balls. I wanted out, Out, OUT, but my trapped cock responded
like a race horse to the bugle. I was trying to get hard, even though
there seemed to be no chance of that while this horror was attached to me.
Mommy had started talking, and I finally calmed down enough to
listen. " a few short weeks, and you have to learn to think about your
date, not about yourself. You see, princess, this is a chastity device. It
will, among other things, force you to sit while you pee, and completely
restrain you from getting hard, and using your boy cock like a man. While
you are still a male, you are not a man anymore. I mean, would a man allow
his bedroom to be turned into his nursery? Would a man wear frilly satin
lingerie, dresses, and nighties? Would a man sleep in a crib dressed like
a baby, or in a bed for a little girl? No real man would have gone
shopping for his own prom gown, now, would he? Finally, would a man allow
himself to have a plug rammed up his bottom, a cock gag into his mouth, and
then get tied up in a baby crib? Of course not! You see, you are a really
a little sissy, and the last few months prove you're a sissy Now Mommy is
going to make sure you are the best, prettiest, and happiest sissy in the
world. That's what this chastity device is really for. You see. if you
can't use your boy's cock, you will start to think more like a girly sissy.
The hormones I have been giving you for the past year have started the
process, and this will finish it. Have you noticed that you don't get hard
as much as you used to, and when you do, you don't get quite as hard? I
know you have you noticed your little bosom developing, and the fact that
you have started to develop the most adorable little bubble butt. Honey,
the boys won't be able to keep their hands off of you, and a lot of girls
will have the same problem!"

After Mommy explained all of this to me, she released me from the
crib, but only long enough to diaper me, and put me in my plastic panties
with the overlay of satin , and a little nightie, and lock me back in my
crib. She left the gag in my mouth, as she said, to help me learn that a
sissy's mouth should always want a cock in it. I was left there in agony
for the rest of the afternoon. Finally, about four, I heard Mommy coming
back down the hall. My diaper was soaked, my throat was parched, and my
jaw ached from the gag. Mommy unlocked the top of the crib, and lowered
the side. telling me that any back talk of any kind would find me spanked,
hard, a large plug in my bottom, the gag replaced, and my diapers would be
left unchanged. I resolved to be a quiet little sissy, at least for now.

I was let free of everything but the chastity device. Mommy told
me that if I wanted it off, I had to be an extra-special good girl until
the prom. If I was good, then it would come off for my date. If I was
naughty in any way, not only would it stay on for 3 additional months, but
I would be dressed in my sissiest baby dress, diapers, and satin covered
plastic panties on prom night, and STILL go to the dance! Needless to say,
whatever Mommy wanted of me, I was going to give her!

Still dressed in sissy dresses, and answering only to Tammy, or
Princess, I had to finish the school year, with both the formal and
informal lessons. I had to study for state mandated end-of-year tests,
still take Mommy's quizzes and tests, and there was still my "after school"
education to go. I had become a pretty good little maid around the house,
moving easily on my high heels and looking rather cute in one of my two
fantasy French Maid outfits. I now had one in traditional black satin with
white lace, and another in pink with white lace. Of course, both had their
matching panties, choker, wristlets, cap, and pinafore apron. I would wear
the pink on the day I laundered the underwear for the black dress, and
likewise, the black the next day. Hand washing Mommy's and my frillies
took about 45 minutes each day(if you include me sniffing her panties), and
along with dusting, cleaning the bathrooms, changing sheets, regular
laundry, vacuuming, etc, there really wasn't a lot of "me" time.
Thankfully, Mommy cooked or picked up carry-out for dinner, because if I
had to add cooking to my schedule, I would have had to skip either school
or sleep!

My days were rather a blur, looking back on them. I wore my little
cock cage all of the time, as Mommy told me that with my cockette free, I
would still think like a boy, and with it out of the way, I could focus on
more girly thoughts. My nights were most always the same: I would go into
the bathroom, and fill myself with an enema, and after expelling the
contents of my bowels into the toilet, I would take a bath. Mommy would
then take me into my nursery and help me up onto the changing table. She
would diaper me, and pull on either a pair of plastic panties and a satin
cover, or an all-in-one pair of satin sissy panties with a plastic liner.
She dressed me in a cute little nightie, place booties and mittens on me,
and then lock me into my crib after tying my pacifier in place in my mouth.
Each night, a plug was placed in my bottom, and I found that I had become
so "loose" that the small plug would pop out of its own accord. Now, I was
forced open with a bigger plug, and there was the addition of a lockable
harness of sorts, made of nylon straps, that held it tightly inside of me.
Of course, if I had been a really good little princess that day, I might
have the immense pleasure of using my mouth and tongue to bring Mommy to a
few orgasms. None for me, though! If I had been a bad girl, messed up on
a quiz, goofed somehow in my cleaning chores, neglected to properly fold
the laundry, or a hundred other faults, I would find myself in the same
crib, but instead of a cute nightie, it was a romper made of hot, crinkly
plastic, and instead of my pacifier, it was a penis gag, thick enough to
fill my mouth, long enough to almost make me gag, with a large, thick
leather pad that pushed hard against my lips. I would also have my little
bottom plugged with a huge vibrating plug, be bound, hand and foot, and
have a very uncomfortable night!

Fast forward to the week before the big prom. Mommy told me that I
had one more little lesson to learn before my "date." We were in the
dining room, having just finished our Chinese take-out, and she told me
that I should go to my room, take off my dress, but leave the rest of my
frillies and my heels on, and then come down to the living room and wait
for her. I went to my room, hung up my pretty pink maid's dress, went
downstairs, and sat down to wait. I didn't have to wait more than a few
minutes when Mommy came into the room. Mommy was wearing a pair of jeans
and a man's shirt. She told me to sit beside her on the sofa. She put her
arm around me and held me close as we talked.

"Honey, my little Princess," she began. "I know this has been
rather strange for you, and even though you never complain, I want to know
how you're really doing, inside, I mean." I didn't know what she meant,
and told her so. "You see, Tammy, you know you really aren't a girl, and I
have sort of forced you out of being a man. You are in a sort of limbo,
not a man, not a woman, but a mincing little sissy. Now, I love you like
that, and I'm sure many other women might, but I want to know about you.
What do you want?" I thought for a long time. I hadn't had any boy
clothes on in many months or more, and my old room was long gone. I was
completely used to dressing like a pretty little girl, and had to admit I
loved the feel of swishy satin on my thighs, and the silky feel of
stockings as my legs rubbed together, and when allowed to wear grown-up
girl clothes, loved the tug of the garter straps across my thighs. I
thought and thought, and then told Mommy that I was very happy being her
sissy, and if we got rid of all the boy things, that would be okay. "We'll
hold off on that for just a bit, sweetie, I want you to remember that your
boy things are all boxed up, nice and neat, and ready for you if you should
want them." We continued to talk for another few hours, the whole time
rubbing my shoulders, caressing my cheek, and finally, she told me it was
time for my final lessons before my date.

I was told to get on the floor, on my knees. I had no idea of what
was going to happen, and with some trepidation, followed orders. Mommy
stood up, and stepped in front of me. "I'm playing a man for right now,
and you are going to be my date. I want you to unbuckle my belt, Tammy,
slowly." I did so, and stopped. "Now, little sissy, undo my jeans and
pull down the zipper." Again, I did as I was told. "Pull my pants down."
I did, and saw two things right away. The first was that my mother was
wearing a pair of men's boxers, in fact, an old pair of my boxers! The
second, and scarier thing, was that she had a huge bulge in my boxers! She
reached down, and slid the boxers off her ass, allowing a large strap-on
cock to spring out!
"Suck my cock, sissy! Mommy commanded, giggling a bit. I just
froze, and Mommy began to caress my head, telling me that if the situation
presented itself, I had to know how to satisfy a man. Slowly, with lots of
coaching, I learned how to kiss and lick the shaft and balls, and finally
to take the realistic rubber cock into my mouth, I was taught how to suck,
and to play with it at the same time, and finally how to take it all into
my mouth without gagging. After a tiring hour, Mommy told me she was
satisfied with my progress, and that only one thing was left for my date
next week, and a trip to the beauty parlor would take care of that.

The Prom day, Friday, morning had finally come! I had to get up
earlier than usual, as I had an early appointment at the beauty parlor.
Once there, my hair was shampooed and rinsed, and then Mommy and
Ms. Bryant, the lady who owned the salon, had a very spirited discussion
about my hair for the evening. Mommy showed her a picture of the gown, and
they finally agreed on something called a French Braid. My hair was
trimmed a bit, and then some soft highlights were added, and I was forced
to sit with aluminum foil strips in my hair for a long time. The whole
time, I could see my sissy panties in the mirror, as Mommy had made me wear
a pink satin blouse and a very short denim skirt today. It was rather
embarrassing, but at least no one could see my cockette or my chastity
cage! Ms. Bryant finally took the foil out, and working quickly, she
arranged my hair in an elegant braid, and I loved the results! Mommy
thanked her, and without thinking, I thanked her, while giving a deep
curtsey. Both Mommy and Ms Bryant chuckled at that! After that, it was
off the the mall and the nail salon, where I received my first set of
acrylic nails, painted, of course, in light pink. I also got my first
pedicure, and I have to admit that I loved the attention, not to mention
the results. On the way home, I couldn't stop looking at my nails, and
pulling down the visor mirror to see my hair, and wondering about the whole
guy/girl thing. I loved wearing lingerie, and I loved looking pretty,
but...I had to really think about who or what I was. Was I a guy who liked
to dress up? Was I a girl in a boy's body? All I really knew was that I
was a sissy, as Mommy said, caught in some kind of sexual limbo. Hell, I
was only 16, and had never even had a chance to be Mike and date a girl.
Was I missing something? Still, I thought, I had probably had more sex,
and with a prettier woman, than 90% of the young men in the world. Kinkier
sex, too, I thought with a chuckle.

       Once home, we sat down to a light lunch, and after we had eaten,
and I had cleaned up the kitchen, Mommy asked me to make some tea and join
her in the living room. Within a few minutes, the lovely Royal Dalton tea
pot was filled with piping Earl Grey tea, there was a small plate of fresh
lemon slices on the tray, another plate with a few cookies, and two Royal
Dalton tea cups. I brought them into the living room, and even though I
wasn't in my maid's dress, I held the tray with one hand, grabbed the hem
of my skirt with the other, and curtseyed while telling madam that the tea
was ready. Mommy chuckled, and said, "Well, Fifi, have a seat, pour us each
a cup of tea, and we'll talk a bit."

       Giggling myself, I poured us each a cup and sat down. Mommy turned
to me and asked if I was ready for tonight. "Well. I have my dress, shoes,
lingerie,..." I began, but was cut off. "No," she said, "Are you ready,
you know, up there (she pointed to my head)?" I thought for a moment and
answered her truthfully. "I really don't know if I'm ready or not, Mommy.
On one hand I love the dress, and all the frillies I get to wear with it,
but I'm scared about being out in public with a boy. What if the other
girls find out I'm not really female? What if Scott finds out I'm a boy?
What if..." Mommy put her finger to my lips to shush me. "Sweetheart,
first of all, one of the reasons for a long, formal gown, rather than the
short ones that are in fashion, is to keep Scott from having free access to
your little secret. Even if you dance very closely, he should never be
able to tell, as your little cage holds everything down. Now, if you like,
we can use another little device tonight. I have what's called a gaff
here." She held out a rather small thong, of simple black. "This is made
of mostly Spandex, and should push your little cockette back out of harm's
way. Would you like to try it?" I stood up, and slid my panties off, and
then worked that thong up my legs, and finally settled it in place. With
my cage, it was very uncomfortable, and would probably be painful before
too much longer, and I told Mommy this. "Hmmm," she said thinking. Let's
see what it looks like, and feels like, with your little cage off. She
produced the key, told me to pull the gaff down, and removed that hateful
little plastic penis prison. I slid the gaff back up, and found that if I
tucked my cockette between my legs a bit, it was not only fairly
comfortable, but totally concealed my true sex. Mommy stood up, and began
to kiss me, passionately, and caressed my budding breasts through my thin
blouse and bra. She did everything to arouse me, with the exception of
touching my cockette, and though I was totally aroused, the gaff allowed no
betrayal of my erection. "Oh my baby, that works so well! I think I can
do one more thing to help you get through the dance, and we try that very
soon. I pulled my panties back on, still very horny and hard, but with
nothing showing, "down there."

       We finished our tea, and while I cleaned the kitchen, Mommy went
upstairs. Twenty minutes later, we left the house with two suitcases, and
drove to an elegant hotel near Scott's house. Once there, I was told to
take a bath, and to make sure there were no stray hairs anywhere, which was
a very easy task, since I had very little body hair to begin with, and used
hair remover every few days on my underarms, and, "other places." I shaved
very close, which again, wasn't hard, as I only had to shave once a week,
and only got a five day shadow, not a five O'clock! Once dry, Mommy told me
to come into her bedroom of the suite. She was wearing nothing except for
her delicate white silk panties, stockings, and garter belt. I was told to
lie down over her lap. "Are you going to spank me for something?" I asked,
almost backing away. "No, my little princess, I'm going to do something
for you to help you." With some trepidation, I lay across her lap,
reveling in the feel of the nylon stockings against my body. She then
applied some lube to my hole, and reached around behind her to pick
something up. "Please, Mommy," I began to beg, almost crying, "Don't put a
plug in me, I'll be good, I promise!" "Hush my little darling, I will do
nothing of the sort to my princess! What I'm going to do is "milk" you,
and get rid of all that pent up boy cum inside you, so you can be pretty,
and dance all night without worrying about your little cockette getting in
your way!" With that, she clamped her stockinged legs around my hard
little man, and pushed something cold, but not very large into my backside.
She moved it around a bit, and finally hit a spot inside of me that drove
me crazy! I began to hump her legs, and while she moved this probe around
with one hand, she began to caress my breasts with the other. I was riding
a huge wave of sexual pleasure, and suddenly, I began to dribble cum from
my little cockette, and every time that probe hit the magic spot, I let
loose another dribble of cum, but never hit the orgasm that I felt building
and building inside of me. It was like a huge surge of electricity, like
just before I would shoot my cum out. I can only liken the feeling to a
symphony that kept building up to the climax, and instead of ending in a
crash of strings and brass, just kept building! Finally, I was empty of
cum, but still had had no orgasm! Mommy moved the probe around a bit more,
and then pulled it out, and told me to stand up. As I stood there on
rubbery legs, she turned me around, and used a couple of baby wipes to
clean the lube from my backside, and then to clean my very soft little
man. "There, my little girly, no more of that nasty boy cum in you, and you
can enjoy your date. With that, she handed me my gaff, and with shaking
hands, I pulled it up my legs, and hid my cockette from sight. Mommy told
me to put on the robe on the bed, and go to my room while she cleaned up my
mess. I walked slowly to my room, with the thong from the gaff in the
crack of my bottom, wondering where a nice, respectable mother would learn
to do such things to her son!

       In just a couple of minutes, she was in my room, dressed in a
lovely ivory dress with a pink rose pattern, and strappy white heels. She
sat me down in a chair, and proceeded to do my make-up for me. Fifteen
minutes later, I thought I looked beautiful! She helped me to put on my
new demi-bra, and when I reached for my panties, she giggled. "No, no,
princess, the garter belt and stockings first!" I looked at her with the
question in my eyes, and she giggled again. "How on earth could you ever
get your panties down to go potty if the straps were over your panties?
And what if you wanted to take them off for, let's say, some other reason?"
I blushed, and she giggled again. "Well, maybe not tonight, but there will
be other times you might want to, my beautiful little sissy girl!" With
that, she helped me roll those soft silk stockings up my legs, and then she
fastened the garter tabs to the stockings, and adjusted them. Now I was
handed the black silk panties, and I pulled them up, and then went to the
full length mirror. I could see nothing, nothing at all that even vaguely
hinted that there was a boy under the hair, make-up, and lingerie. I
looked as feminine as if I had been born with a pussy, instead of a
cockette. I turned this way and that, and finally stood on my tip toes,
and looked over my shoulder at my bottom encased in the elegant black silk,
and Mommy just laughed. "Just like a girl!"

       It was now about half past five, and Scott was supposed to pick me
up just before six, so we could go out to dinner, and then on the prom,
which started at eight. Mommy used some very pretty perfume, and put some
on my wrists, the backs of my knees, my throat, and with another feminine
giggle, sprayed just a touch on my navel! She then took my dress from the
bag, and helped me into it, sliding the zipper up the back, and hooking the
little catch at the top. Kneeling in front of me, and telling me to put my
hands on her shoulders, she helped me into my high heels, buckling the tiny
ankle straps. Standing back, she took a good look at me, and then asked me
what earrings I wanted to wear. I panicked, as I had not thought about
jewelry at all! With another giggle, she went to a little box, and pulled
out a pair of gold earrings with a little dangle, and each dangle rested a
diamond! These were the earrings I wore on my wedding day, and I would be
proud if you wore them tonight. I was flabbergasted as she fastened them
in my ears, and then stood back yet again. "Hmmm, she said, a necklace,
or..." Back to the box again, and she the took me back to the mirror. She
stood behind me, and wrapped a thin white satin choker, with black lace
trim around my neck. In the center was another tiny gold dangle with a
matching diamond! "There, my elegant little princess, what do you think
about that! It was so beautiful, I almost started to cry! "I love it
Mommy It looks so pretty" She busied herself tugging my dress this way and
that, fixing stray hairs that weren't there, and straightening stocking
seams that were already straight. Finally, it was about ten minutes until
six, and she told me to wait in my room until Scott and his parents
arrived, and then I could make my "entrance."

She left, and I took the time to twirl and pose in front of the
mirror, loving the glossy blue satin gown, and the way it made me look so
pretty, so sophisticated, and yes, so sexy! The gown shimmered in the
light, and the feel of it as it swished over my silk covered legs magic! I
lost myself in the sensuousness of it all, forgetting for the moment, that
I had to go out with a boy, dance with a boy, and...well.
All too soon, I heard a knock at the door to our suite, and then
Mommy talking with people, and finally she called to me. "Oh Tammy,
Sweetheart, are you almost ready?" "Just a moment, Mother," I called back,
remembering at the last second to call her mother around other people. I
screwed up my courage, picked up my feet, and went into the living room of
the suite. Scott's parents were seated on the sofa, and Mommy was in a
chair, but all I could see was Scott. He was tall, tanned, and in a word,
sexy! He had blonde hair that was cut short, was clean shaven, and was
wearing what was obviously not a rental tuxedo! Nervously I stepped into
the room, taking tiny steps, trying to "glide" like Mommy did on her heels.
It must have worked, because his eyes never left me! Scott's Mom and Mommy
both stood, and introductions were made, but I never hear a word, all I
could look at was Scott!
       I found out he was as nervous as I was when he handed me a
beautiful wrist corsage of baby's breath and pink rose buds. His hands
were shaking so much, he could barely put it on me! That broke the
tension, and after the usual thousand snapshots, we were out the door, and
heading for the lobby of the hotel. He stopped at the desk, and asked that
his car be brought around. While we were waiting, he told me how beautiful
I looked, and I blushed and told him he was very handsome himself! He was
wearing some nice cologne, and I just wanted to eat him up, right there,
right then! I asked him about his tux, as it was obviously not rental. He
laughed and said, "This is my father's tuxedo, and his tailor altered it to
fit me nicely." and then laughed and told me "It's about the same vintage
as that absolutely beautiful dress you're wearing, Tammy!" I blushed,
deeply, but thought it was going to be a nice evening, I could tell!

       The valet pulled up with the car, a new Buick. Nothing grand, no
limo, no Ferrari; just a very handsome young man with a very nice car. He
held the door for me, and I was very glad of all the practice Mommy had
made me go through, as it wasn't easy to get graefully into a car with this
much dress! He took the keys from the valet, tipped him, and off we went.
We went to a very classy seafood restaurant, thankfully, not that horrible
chain that serves frozen shlock and calls it seafood! Over grilled sole,
and tender vegetables, we talked about school, and home. I told him I was
home schooled, and that this might be my only prom, since there were no
other classmates in my school to invite to a prom! He laughed, and told me
that if it was dates I was looking for, he might be able to provide more
than just this one! I blushed, and wondered what he would think if some
evening he found out about my little secret.

       Dinner over, we went outside to the car, but it wasn't there!
Instead, there was a beautiful vintage car, and a big one. Scott's father
was standing beside the open door, wearing a complete chauffer's uniform!
Scott looked at the expression on my face and chuckled. This is a 1922
Bentley, and it's Dad's pride and joy. He spent the better part of ten
years restoring it! He and Mom took my car to the dance, and we are going
to be driven to the prom in high style! Mr. Roberston held the door for
me, and I slid into the wide back seat. Scott went around and got in the
other side. After Mr. Roberston got in and started the huge car, Scott
grinned and announced, "To the Prom, James, and be quick about it!" "Yes
sir!" his father answered with a laugh. As the huge car purred away from
the curb, Scott's hand found mine, and we rode in silence to the prom,
holding hands. I think I was in love.

       We pulled up the entrance of the local Holiday Inn, and
Mr. Roberston jumped out, and held my door for me, taking my hand and
helping me out of the car. Scott slid over and exited right behind me.
Putting my arm in his, we swept into the motel like a couple of movie stars
on the red carpet. The Holiday Inn banquet room was decorated for the
dance with a variety of paper decorations, silk flowers on all the small
tables, and while it was the typical cheesy decoration for a high school
prom, I thought it was magical. We sat down at one of the tables that had
a beautiful sign labeled "Mr. Scott Robertson and Tammy." I still have
that little table placard as one of my mementos. Scott got us both a glass
of punch, and we listened to the band play a song. They played mostly the
pop of the day, and were pretty good. We danced to almost every song,
sitting out a few of the faster ones. Toward the end of evening, whenever
there was slow dance, I abandoned the fastidious form I had been taught,
and danced very close to Scott, my head on his shoulders, not caring about
steps, just wanting to snuggle closer to this handsome young man. For the
final two songs of the evening, the band dug way back in the ol' treasure
chest, and pulled out a couple of slow song from the 70s. First up was Jim
Croce's, "Time in a Bottle," which had us dancing very close. So close, I
could feel his hard-on pushing into my stomach, and could almost feel the
heat coming off of it! The finale was one the band claimed they played at
the end of each prom, and was The Moody Blues' "Nights in White Satin." It
was the perfect song to end with. Long and slow, I melted into Scotts
arms, and never wanted the night to end. But, end it did. As the song was
ending, I found Scott's lips on mine, and it seemed the most natural thing
to kiss him back. We probably spent the last two minutes locked into an
embrace, our tongues eagerly exploring each other's mouths, and Scott's
hands just a little lower on my back than was decent. I certainly didn't
mind that at all! After the usual announcements to drive carefully, we
walked to Scott's car, arm in arm. As we got to the car, Scott kind of
blushed, and asked me if I was ready to go home. I snuggled up to him and
told him I never wanted the night to end, and was most certainly not ready
to go home! He again blushed, and stammered out that he had reserved a
room here, and if I wanted to...

       Now, it was my turn to blush! I wanted to rip his clothes off and
kiss him all over, but the secret hidden under my gaff was such a huge
secret that I didn't want to ruin the evening by having him find out! I
mean, he thought I was a girl, and he would be really pissed off when he
learned the truth! I mean, I had deceived this wonderful young man, and
now I was embarrassed by what I had done. I hung my head, and began to cry
softly. He took my chin in his hand, and raised my face so he could look
into my eyes. He looked deep into me and softly said, "What's the matter
my darling little princess?" I wasn't sure if I had heard him right, and
stopped crying to look at him. "What did you call me?" I asked in a quiet
voice. "I called you Princess, Princess. Aren't you your mommy's little
princess?" OH MY GOD! HE KNEW! He knew who I was, and more importantly
what I was! He went on, in the same, soft voice, "I mean, I would never
want to invite Mike up to a hotel room, but I think I want to invite Tammy,
if she'll consent to join me. We don't need to do anything but hug and
kiss, if that's all you want to do, but I want to be with you a little
longer tonight, and I hope you want to be with me." Like butter in the
sun, I melted. I whispered in his ear, "My dear Scott, I would love to
come to your room, I want to be with you, to do whatever you like, for as
long as you like.

       It felt like all the world was staring at us as we made our way to
his room. Once inside, we fell into each other's arms and kissed as though
this was our last day on earth. Panting for breath, we finally broke
apart, and Scott told me that there was something for me on the bed. "What
is this, some kind of a present?" I asked, looking at the small overnight
case on the bed, and giggling. "No, I don't really know what's in it," he
answered. Is looked at him funny, and then picked up the envelope on top.
It was addressed, in beautiful calligraphy, to "Tammy, to be opened in
private." I excused myself, and took the envelope and case into the large
bathroom. I opened the envelope, and found a note from Mommy. "My dear
Tammy, if you are reading this, then you are in Scott's hotel room. Don't
worry, it's perfectly natural. As you may have found out, Scott knows who
you are, and knows you are a mincing little sissy. Inside the overnight
bag that I left, you will find something that you really don't want to
find, and that is your chastity device. The lock is unlocked, but I still
have the key. Why have I sent that horrible thing to you? Very simply, if
you go any farther than kissing Scott, you must remember two very important
things. One is, you are a sissy. A sissy is submissive to her partner,
male or female. What you want, how you feel, and your needs are a distant
second to what your partner needs and wants. Therefore, by voluntarily
locking away your cockette, you voluntarily submit to your partner.
Remember, for a sissy, submission to your partner is the path to happiness!
Now, you obviously don't have to use the cage, and no one will be mad at
you if you don't. But remember who you are, and more importantly, what you
are. The second thing I want you to remember is that this is your first
date with Scott, and indeed, your first date, period! Don't "give
everything away." Save something for him to look forward to on another
date, if you choose to grant him that privilege.
       I have also taken the liberty of placing some clean underwear, two
pair of shoes, a skirt and blouse, your make-up, and a sexy little teddy in
the package, if you find you want or need them. Have fun, and remember to
make Scott happy to thank him for a wonderful evening. Love, Mommy

       I stood there for a full five minutes, and only when Scott called
in to see if I was okay did I snap out of it. Mommy was right, I decided,
and pulled my dress up, slipped those soft silk panties off, and removed my
gaff. I opened the case, took out the CB 3000 that I really didn't want to
ever see again, and with a little trouble, and lots of pushing and pulling,
got my cockette locked up in the hateful thing. I hesitated before the
final act of putting the lock through, and with a deep breath, then with a
quick push, I heard the snick of the lock, and it was done. I pulled the
silk panties back up, touched up lipstick, used a quick bit of perfume, and
rejoined Scott.

       We took up where we had left off, our lips locked hungrily onto
each other's. Scotts warm hands were running up and down my back,
caressing my arms, and then moving again to my back, each time, moving just
a bit lower, until his hands were cupping my ass cheeks through the satin
of the dress, and the almost non-existent silk of the panties. "Oh, my!"
he exclaimed softly, "You're wearing real stockings and a garter belt,
aren't you?" "You silly," I answered back, ". I am wearing real silk
stockings, just for you (giggle!)! I mean, what girl feels pretty wearing
stupid panty hose? For that matter, what girl looks sexy in panty hose,
when her boyfriend finally stops messing around and removes her dress?" At
this I kind of cocked my head, and fluttered my eyelashes at him, and he
needed no other urging!

       As though he were handling antique bone china, he undid the hook at
the top of my dress, and slowly slid the zipper down my back. As the
zipper descended, goose bumps ran up and down my spine. When the zipper
finally hit bottom, I let my arms fall to my sides, gave a shrug, and the
dress fell into a satin heap at my feet. I stepped out of the dress, and
once more found Scott's arms. His hands were everywhere at once! As he
ran his hands of my stocking, he made to go farther, but I put my hand on
his and asked him to wait a bit. Kissing his lips, I slid his suspenders
off his shoulders, began to undo the studs of his shirt, and remove the
cufflinks. In an attempt to hurry me, he tried to help. I scolded him
laughingly, "No, lover, this is my job, and I want to take it slowly, and
enjoy every minute of it!" His shirt was tossed onto the bed, followed by
undershirt, and began to kiss and lick his chest, paying particular
attention to his little nipples. I guess no girl had ever done that, and
he drew in a sharp hissing breath, and let it out, "Oh-h-h-h Tam-m-m-y-y!"
While still licking his nipples, my fingers found his trousers, and undid
the button, and gently, slowly, slid the zipper down. Kissing my way down
his tight stomach, I knelt at his feet, and slid his tuxedo trousers down.
I was now face to face with a pair of black silk boxers, and the bulge they
contained was most certainly not Mommy's rubber dildo!

       With Scott's hands gently holding my head, I nuzzled his cock
through the silk, inhaling the aroma of his musk and his sweat. Moving as
slowly as I could, I pulled his boxers down, with him moaning to go faster.
When just the tip of his rampant cock was held by the waistband of his
boxers, I began to kiss and lick everywhere but where he wanted me to.
Finally, I lowered his boxers, and took my first real cock between my lips.
It was long and thick, even bigger that the strap-on dildo that Mommy made
me practice on, but it felt so much better. His cock was warm, and felt
like velvet covered steel in my mouth. I licked and kissed the head,
licking my way down the shaft, and then taking his balls in my mouth and
gently sucking them. Scott was rocking back and forth, and moaning loud
enough to be heard in the lobby! I eased to my feet, and led a very dazed
young man to the bed, and told him to sit down. I knelt back at his feet,
and once again, began to lick, kiss, and finally suck on that magnificent
cock! Mommy's strap-on was 8 inches long, and an inch-and-a-half in
diameter, and I knew that Scott was a little bigger. His shaft filled my
mouth, and when I had taken the head of his cock deep into my throat, my
nose in his pubic hairs, I almost gagged, as it was deeper than any dildo
or gag I had been exposed to! I used my hands to manipulate his balls, and
to stroke his shaft, so I could give my throat a moment to relax, and then
went back to sucking his cock. His moans began to be rhythmic, and become
faster and faster, and I matched his moans in tempo, bobbing my head up and
down, sucking hard on his monster, until his legs started to shake, and I
could feel a tremor go through his body. His cock got even harder, and
suddenly, he was shooting a thick wad of cum into my mouth! I pulled my
head back until only the head of his cock was between my lips, and
swallowed as fast as I could, then lowered my head back onto his softening
member, gently sucking him dry, swirling my tongue around his cock, and
only when he gently pushed my head away, did I reluctantly allow that
wonderful piece of man-meat to leave my mouth. Looking Scott in the eyes,
I gently kissed the head of his now soft cock, and quietly said, "Thank
you, sir, for allowing me the pleasure of sucking your cock." I had sucked
my first cock, and was certain that it wouldn't be my last!

       Scot had swung his legs up and laid on the bed, spent. I got off
the floor, removed my heels, and lay down beside him. We kissed, and his
hands roamed over my bra-covered breasts. "How did you get such real
feeling breast forms," he asked. I almost snorted! I sat up on the bed,
unclasped my bra, and lowered one, not-so-artificial nipple to his lips.
His eyes were huge as he began to suck on my nipple, gently biting it, and
almost jumping when I said, "Ouch!" "Oh my God, you are amazing, Tammy!"
He breathed. "What do you have between your beautiful legs? Are you a boy
or girl there?" Before I could stop him, his hand had slid under the
waistband of my panties, and he froze. "What do you have down there,
Tammy?" Reluctantly, I got out of bed, and pulled my silk panties down for
him to see. "Scott, it's called a chastity device, and I'm wearing it to
remind me that tonight is all about your needs, and your desires. My
pleasure will come from giving you pleasure. "So, is the key to this
contraption here?" I hung my head with embarrassment, "No, sweetheart, my
Mommy has the key." I went on, with my head down, my eyes on the floor, to
explain about the note, and how I really was a submissive sissy, not a man,
not a woman, but a sissy. Scott listened to me in silence, and then got
out of bed and took me in his arms. "You mean, you locked that thing onto
yourself tonight in the bathroom?" I nodded. You're cock was free all
night up til then? "Cockette, I don't have a man's cock, I have a sissy's
cockette." I corrected him quietly, tears of shame running down my face.
""I'll get dressed now, and call my mother for a ride home. I'm sorry I'm
not what you wanted, I'm sorry I'm not what you needed. I'm sorry I ruined
your one and only Senior Prom." With that, I broke his hold on my arms,
and rushed into the bathroom, where I sat on the toilet and cried my eyes
out, while trying to find my cell phone in my purse.

       I might be a good sissy, but I guess I make a lousy girl. Sure, I
got the rush-into-the-bathroom-cry-your-eyes-out-call-mommy thing down
pretty well, but nobody told me that I should always lock the door behind
me for these scenes! Since it wasn't locked, I saw it slowly swing open,
with Scott, naked, except for his black socks, standing in the doorway.
"Tammy," he said in almost a whisper, "Tammy, why are you crying? Please
come in and talk to me, please!" I looked up at him through my tears, "But
I ruined your prom! You wanted a girl, and you got, this!" I waved my hand
disgustedly at myself. Scott replied sofly, "Tammy, Tammy, I went to the
prom with a transvestite named Tammy, who used to be Mike. I went with a
young boy who has been feminized by his mother. I went to the prom with
the most beautiful person in the world! You were prettier than any of the
real girls, or any of the boys! You are a wonderful dancer, I really enjoy
talking to you, and just a few minutes ago, you gave me a blow job that has
to go down in history as one of the top ten ever given! How in the heck do
you think you ruined my, our, Prom? Please tell me!" With that, he took
my arms, and stood me up. I allowed myself to be led back to the bed, and
sat down on the side. Scott sat down beside me, and put his arm around my

       "Your mother warned me that you might get a little emotional. She
told me that this was your first date, and you might end up a little
confused as to who or what you were. I can't answer that, Tammy, I
sometimes can't even figure out who I am! What I do know is that you are
soft, warm, and beautiful! I want to lay here with you, kiss you, hold
you, and make you feel special, because you are so very special." With
that, he kissed me on the cheek, and when he went to do it again, I turned
my head, and we kissed each other tenderly for a moment. I excused myself,
grabbed my bra, and went back to the bathroom. I washed my face, and took
my hair down from the braid. I spent a few minutes brushing it out until
it shone in the poor lighting. I quickly repaired my make-up that my
crying jag had ruined. then, I opened the overnight case, removed the
delicate, baby blue silk teddy. It was so pretty! I held it up, and
realized it was one of Mommy's! I slipped off my panties, pulled the teddy
on, and slipped my high heels back on. satisfied that the teddy did an
adequate job of hiding my cockette cage. I applied some pink lip gloss,
and feeling rather guilty for the way I had acted, I stepped back out into
the room.

       Scott had been watching TV, but as soon as I opened the door, he
turned it off and stood up. He had put his boxers back on, and from the
look on his face, I don't think he expected me to come out in lingerie! He
tentatively walked towards me, and stopped. I did the same, and then, at
almost the same instant, we almost jumped into each other's arms! After a
few minutes of gentle kissing and caressing, He quickly told me to move the
silk of my teddy out of the way, and then he examined my chastity device
closely. "So," he asked, as he fondled my shaved little ball, "If we got
that thing off of you, would your little, cockette, I think you called it
work? Would you get hard like a boy?" I told him about the hormones I had
been taking, and how the limited how hard I could get, and then, with my
face burning with shame, I told him that I had been milked earlier, anyway.
"Milked?" he asked with a puzzled look. I told him all the humiliating
details of my ordeal, and I noticed that the more I talked about it, the
harder his cock got in his boxers

       I reached over and touched it through the material, and said,
"Well, someone seems to be ready for round two!" I asked him if Mommy had
given him any specifics about my feminization, and he said no, but he would
love to hear. I began by telling him about the corset, and about being
gagged and handcuffed to the bar. From the way his cock seemed to grow
even larger, and twitch in his boxers, that seemed to really get his motor
running! I then told him about my first butt plug, leaving out no details!
There was no doubt about it, his cock was as hard as a telephone pole, and
looked damn near as big! He grabbed me roughly, and began to kiss me with
unrestrained passion. I returned his ardor, and wrapped one hand around
his cock, his amazing cock, that had just cum thirty minutes ago, and
seemed to be more than ready to go again! With my other hand, I reached
behind him, and ran my hand under his boxers, and ran my manicured nail up
and down the crack of his ass. This made him wild! He grabbed my head and
pushed it down on his cock, and I barely had time to pull his boxers down
before it was jammed down my throat! There was no tender passion this
time, no, he fucked my throat like a wild man!

       We then slept until about nine. Well, I got up at nine, Scott was
still snoring! I took a shower, and then looked to see what Mommy had
packed me to wear. There was a short white denim skirt with a pink lace
hem, and a pink belt, a white satin blouse, nylon sissy socks (of course!)
with pink lacy tops, and two pairs of shoes. One was was a very cute pair
of pink tennis shoes, and the other was a pair of white, 3 inch high heels,
with rounded toes and a strap across the instep. I remember her buying
these, and they were called baby doll pumps. I pulled on the sissy socks,
and then reached in for the underwear. You guessed it, sissy panties in
white satin with stiff pink lace, and a pink satin bra to go with them. I
slipped it all on, and did my hair and make-up, choosing the pumps at the
last minute. I figured that I could change shoes quickly if we went
anywhere I would need them. About that time, I heard Scott, so I slipped
back into the bedroom, where he was laying on top of the sheets,
stretching. I minced over to the bed, and bent to give him a kiss, and he
sort of rolled away from me. The whole time he was showering and getting
dressed, he was rather cold and abrupt, and I soon realized that his ardor,
and his lust had cooled. He asked me mechanically if I would like to go to
breakfast, and I lied and told him I wasn't hungry, so without any more
fuss, he drove me back to the motel in silence, where I ran to our room,
flopped on the bed, and cried my eyes out like a little girl.

       Mommy came in, and took me in her arms, and held me like a baby.
She told me that it wasn't my fault, and that many men thought with their
cocks, and not their brains, and in the cold light of morning, what seemed
great the night before, suddenly took on a new aspect. You see, sweetie,
Scott is bi-sexual, and thought that the idea of a beautiful shemale like
you, a gorgeous little sissy was the answer to his own conflicted needs.
With his cock, I'm sure, drained by my little princess (I blushed heavily!)
he was once again thinking with his thick head, and decided that he didn't
want to be seen with a sissy, even though you are much prettier than any
girl he ever dated. It's not your fault, my little darling!" With those,
and many other words, she comforted me, and finally stilled my crying.
Mommy helped me fix my make-up, brushed my hair for me, and told me she was
leaving my chastity device in place for a while longer. For some reason, I
didn't protest at the restraint. It seemed to feel natural to me. It also
depressed me that it felt that so natural. For the first time in a long
time, I really wished I had a pair of old jeans and a sweatshirt, instead
of this frilly, sissy shit. With that, we packed up, checked out, and
spent the day window shopping, and having lunch.

       On Monday, it was a different story, though. I was still very
depressed from Scott's treatment of me, and really wanted to forget this
whole damn Tammy shit, burn all of my feminine clothing, knock off the
hormones, and go back to being a boy. Okay, I wasn't a real big success as
a boy, but at least I knew what the hell was going on around me! This shit
was too damn confusing! But, like the submissive Mommy had trained me to
be, I got up, and started to dress in my yellow, ultra sissy dress for my
last week of "Mommy School" As I was dressing, Mommy stopped me, and asked
me to put on a nice dress for going out. Without much enthusiasm, I
selected a pretty, pale blue sun dress, and put on a pair of pale blue
satin panties with just a touch of lace and cute little white bow on the
waist, and a matching bra. I slid on a half slip and then pulled on a pair
of white nylon ankle socks with no lace, but a white bow at the back of
each ankle. My white baby doll pumps seemed to be appropriate, so I put
them on too. When I looked in the mirror, I was surprised, somehow, to see
a pretty girl looking back at me. Somehow, after Scott's very uncavalier
treatment, I had spent the rest of the weekend feeling like an ugly freak
in a dress. I had ignored the mirrors, and spent all day, both Saturday
and Sunday, either sleeping, playing violent games on my computer, or
watching television. I'm sure Mommy also noted that even though I was
wearing panties and a bra, I had also dug out my old robe and a pair of
shorts from the boxes my boy things were in, and was wearing them over my
frillies. I had wanted to wear jeans, but found they were a lot too short,
so I said the hell with `em. Now it was Monday, and even jeans that didn't
fit sounded like a wonderful alternative! I may have looked pretty, but I
didn't want to look pretty!

I didn't even ask Mom where we were going. I just got in the car,
buckled my belt, and leaned back. She asked me if I wanted to stop
somewhere for breakfast, and for the first time since I had started this
female stuff, I snapped at my mother, "Hell no I don't want to stop! The
less people that see me in this shit, the better! Let's just do whatever
it is you want to do, and then take me home!" Mom gave me no reply, but
stopped at McDonald's drive through, and got us each a breakfast sandwich,
some coffee for her, and an OJ for me. I ate in silence.

About 15 minutes later, we pulled up at a non-descript office
building. Mommy held the door for me, and we rode the elevator up the 3rd
floor. Thankfully, it was empty, as I really wasn't up to seeing anyone,
or having them see me. Once off the elevator, we walked down the hall into
some kind of a doctor's office. I wondered if Mom were sick or something.
The waiting room was empty, and when Mom gave her name to the receptionist
we were told that the doctor had come in her day off for this, and to go
right on in. Wow, a doctor's visit without a wait! Either this was some
kind of an emergency, or this was one lousy doc with no patients!

       I walked into the doctor's office, wondering what was wrong with
Mom, and why she wanted me to be in the office with her. Maybe she didn't
trust me to be at home, or alone with the way I felt. Either way, I really
didn't care, just sunk down in the chair and waited until we could go home.
After a very short wait, the doctor came in. It was a she, and she was
very pretty! Black high heeled sandals gave way to coffee colored hose,
which led up to a beige skirt and jacket. Very business-like, with just
the hint of a satin blouse or camisole peeking though to remind you that
there was a woman behind the suit. Her blonde hair was pulled back, but
not into a severe bun, and her make-up was subtle, and again,
business-like. The only thing about her that came across as a lively
human, were her bright green eyes, that looked like they missed nothing,
and were amused with everything.

       Dr. Starnes looked at me, and finally told me that she was a
psychiatrist, and when Mommy called her to tell her how depressed I was,
she set aside a couple of hours on her day off to talk to me, to see if she
could help. At this, Mommy stood up, and kissed me on the cheek, and told
me to tell Dr. Starnes the truth, and she would be able to help me make up
my mind, and decide who I really was. After kissing me again, this time on
the lips, she did a surprising thing: She walked over to the Doctor, and
kissed her on the lips! The Doctor patted Mommy on the ass, kissed her
cheek, and told her to go have some coffee across the street, she would
call when I was ready to go.

       "Well, now," Dr. Starnes began, "I know why you're here, do you
really understand why your mother brought you here?" "I-I t-th-think so,"
I sputtered out. Dr Starnes told me to relax, and she asked me if I was
okay with her relaxing a bit. I sort of nodded, and she removed her
jacket, and hung it on a hook by the door. I could now see a creamy white
satin blouse, which in turned covered what looked like a camisole, and no
bra. I must have been staring, because she chuckled and asked, "Do you
like my teddy, Sweetie? I love to feel pretty and girly under my suit, and
a satin blouse and teddy do just that for me!. Do you like that too? With
those simple words, I began to bawl, crying like I would never be happy
again. "Ah, I thought as much! You don't know whether you are Mike,
Tammy, or some other person that we haven't named yet, do you? Well,
(handing me several tissues) that's what we are here to explore, to find
out what path you wish to travel!" I sort of looked at her, and slowed my
tears, just a bit. "Now, first things first. I want you to use my first
name today, so don't call me doctor, call me Ella, okay? "That's a very
pretty name," I managed to snuffle out. "Thank you! Now, here's the
problem we have today. What do I call you? You're wearing such a cute
dress, and your hair is so pretty, I want to call you Tammy. But, I
suspect you aren't really very happy with Tammy right now, so which name do
I use? I thought for a long minute over that. "Well, I've kinda gotten
used to Mommy calling me Tammy, or her princess, so I suppose Tammy would
be okay today." "Tammy it is then! But, if it bothers you at any time,
let me know, okay? So, what we are going to do is break everything down,
see where you have been, what you have been doing, what you have been
thinking, and try to figure out which way to go from here. You are sort of
like a ship that was heading one place, drifted a bit with the current, got
back on course, and then got shoved half-way around the world by a
hurricane. Does that sound like you?" I nodded emphatically. "Let me
fill you in a bit. Most of my clients come to me for advice and medical
treatment prior to surgery to change them from male to female, or female to
male." I must have jumped out of the chair at that, because she quietly
asked me, several times to relax, and sit down. "Now Tammy, I know you
don't want surgery, your mother knows that, and anyway, I can't do it here
in the office! I'm not even a surgeon, so relax! I was just explaining my
specialty. Something else you need to know, and may have guessed at, is
that your mother and I have been lovers. After your father ran off, your
mother started to see a psychologist, and at that time, he and I shared an
office suite. I met your mother coming out of his office one night in
tears, and offered to buy her a cup of coffee or something, as there was no
way she was in any kind of emotional shape to drive home. One thing led to
another, and as I'm a lesbian, it eventually led to my bedroom. I'm sorry
if that shocks you, Tammy." Shock me heck! I my cockette hadn't been
restrained, she could have seen that my cockette was trying to get hard as
a rock under my dress!

       "So, I want to be truthful and upfront with you, and I would like
you to do the same for me, okay?" "Okay, Doctor St...I mean okay, Ella." I
replied shyly. "Now, I know that your mother has pushed you hard, harder
than maybe she should have. I also know she has told you why she hates
men, and your father in particular. What you may not really understand is
that she sees your father in you!" I started to protest, and she let me
run on for a bit, and then stopped me. "I know you aren't your father, but
a person's perception often colors their judgment. Do you understand what
I mean?" Well, we moved to the sofa in the next room after that, and
sitting beside this beautiful woman, I began to trust her, and told her the
whole story, from start to finish. Sure, she knew it all already from
talking to Mommy, but she wanted to hear it from me, and hear the take I
had on it all. She asked very few questions until I had it all out of me.
I felt as though I had run a marathon! She went to a little refrigerator;
got us both a Coke, and then the interview began.

       She began by asking me to go to the mirror and describe what I saw.
I did, describing my dress and my hair, laughing when I described my ruined
make-up. "No Tammy, what I want to know is who you see in the mirror." I
froze. She didn't say anything else. I stood there, struggling for an
answer, and finally blurted out, "I see a boy who looks like a girl, is
dressed like a girl, but isn't a boy or a girl!" "Perfect!" she cried.
"That is exactly who you are! Now for a harder question. Do you want to
have surgery to be completely a girl?" I flinched at the question, but
studied my reflection for a while, and answered, "No, I don't think so."
"Well, do you want to be 100% boy again?" Again, I stared at the mirror.
I fingered the light cotton dress I was wearing, and without thinking,
lifted the hem to stare at my satin slip, then lifted that to stare at my
panties. I forgot she was in the room at all, as I ran my hands over my
stockings, my panty covered, plastic encased little cockette, and then my
small breasts. I brushed the hair out of my eye, and finally turned around
to the doctor. "Ella," I began, and then started to cry again. In a rush,
the words tumbled out of my mouth without conscious thought. "I like
wearing panties and pretty things! I like the way my legs look in high
heels! I love to wear satin and lace, but I'm a boy, and it's not right
for a boy to like to wear pretty things!" She walked over to me, and
hugged me, leading me back to the sofa, and handing me a tissue. "Why
isn't it right, Honey? Who says it's wrong? I find you a very attractive
young thing, and you wear your clothes so well! Clinically, you are what
we would call a transvestite, or a transgendered person, a man who likes to
look and act like a lady, but doesn't want to be a lady. The other term I
might use isn't as scientific. You're a sissy, and a beautiful sissy at
that." I jumped at her words, and quietly went back to the mirror. I
began to use a tissue to wipe my smeared make-up, and looked deep into the
glass to try to see the old Mike. He just wasn't there, and at that
moment, I finally realized that I was sure, well, pretty sure, I didn't
want to see him there. We talked for another hour or so, and she finally
asked me the loaded question. "Tammy, are you gay?" Again, I flinched!
"Well, when I was with Scott I, uh, I, well, I" I froze up, and then in a
rush, "Isuckedhiscock!" "Now Tammy, did you like it?" With the tears
leaking again, I told her that I had loved it! "So, if a boy had sucked a
man's cock, would he be gay?" "Absolutely!" I almost yelled. What if I
sucked a man's cock. Would that be a homosexual act?" "No, that's what a
woman does, right?" That's right, Sweetie, but you aren't a woman, are
you?" I shook my head. "But, you're not really a man either, are you?"
Again, I shook my head. "So, little Tammy, if you aren't a woman, then sex
with a woman is normal, and if you aren't a man, then sex with a man is
normal. You are a little of both, so for you, nothing is really wrong, you
see. You may have not made this journey on your own, but here you are, not
one thing, and not the other, but a beautiful blend of both!" I nodded,
slowly seeing her point through the fog in my mind.

       Now, she asked me to take off my dress. I was shocked, and with
her admission to being a lesbian, wondered what was coming next. "It's
nothing sexual, Sweetheart, I just want you to see the real Tammy/Mike. I
slowly took off the dress, and at her prompting, removed my bra and
panties, then my heels and stockings. I stood there, naked, wearing just
the cage in front of the mirror, and really for the first time, took stock
of what I saw. I had long, pretty hair, small but firm breasts, a flat
little tummy, nice bubble butt, smooth legs, and a penis sticking out. She
walked over to me and stood behind me. "There, now there is nothing
between you and who you are. No pretty lacy things to distract you, no
sexual stimulation, just you and the mirror. She pointed to a little
table, where there was a key on a heart shaped ring. It was the key to my
chastity device!

       "Now, we are going to play a little dress up, well, you are going
to dress up, if you choose. But first, I want to you to use the key there,
and release your male biology. We need to do that to make this work" I
nodded slowly, and while she walked over to pick up a large cardboard box,
I removed the CB 3000. She handed me a sports bra, and asked me to put it
on. I did, and it was very tight, and seemed to push my breasts down,
flat. Next came a standard white cotton T-shirt, followed by a plaid short
sleeved shirt. She handed me a pair of boys briefs, and I pulled them on.
Next, she handed me a pair of jeans, some white socks and tennis shoes.
Putting them on felt sort of strange, but sort of like, well, coming home
again after a long trip. Finally, she handed me a plain red baseball cap,
and helped me tuck my hair up a bit. Now I was told to look in the mirror,
and tell her who I saw. With no breasts, no lingerie, and no make-up, I
was looking at Mike again, and I told her so. "How do you feel about the
nice young man you see in the mirror, Mike?" The question hung in the air
for about five minutes, as I stood there, turning sideways, then straight,
and staring into the mirror the whole time. After a while I looked at the
doctor, and said, "It's the old me, Ella. It looks like I did before Mommy
started dressing me up!" "But Mike, the question remains, how do you feel
about the boy in the mirror?" Again I paused, and was surprised to note
that the reflection looked like the old me, but I didn't feel like it was
me. I was somehow detached, as though looking at a picture of someone
else. I quit staring, and then told her that he looked like a nice,
normal, average boy, nothing special about him. "So, do you like him?"
"What do you mean, Ella," I replied slowly, "Do you want to know if I would
date him or something?" "Would you date him?" "I don't know. He looks
kinda skinny and small, not really a man," was my unconscious reply. Now,
she asked me to take Mike's stuff off, and put them in the box. Once again
naked, she went to another box and told me that she had another little
outfit for me. She handed me a a pair of disposable diapers, and asked me
put them on. I was a bit ashamed, but did it for her. Next, she held out
two pairs of plastic panties. One was pink with little stars, and the
other was plain white, and she told me to pick one. I took the pink pair
from her, and slid them up over the diaper. The next two items were
T-shirts, again, one in white and the other in pink. Instinctively, I took
the pink t-shirt and pulled it on. Back to the mirror, and again, Ella
asked me who was looking at me, and how did I feel. I stared again, but
not as long this time. "I see baby Tammy, and she looks kinda cute."
"So," Ella asked, "How do you feel when you are baby Tammy?" I feel kinda
helpless, and small, but I love how Mommy takes care of me, and changes me,
and makes me feel so good!" I stood there a while longer, and another
question came my way. "If you had to go to the potty right now, would you
use your diapers, or would you ask to use the bathroom?" "I wouldn't want
to have a wet diaper in your office, Ella, that wouldn't be nice, would
it?" "Do you have to go, Honey?" I nodded. "Well, then either use the
bathroom, or your diapers, it's okay, whatever you choose!" I didn't think
it over long. I had been trained to pee in my diapers, and did just that,
but I was so-o-o embarrassed! Without a word, Ella led me back to the
leather sofa, and asked me to lie down on it. She slid my plastic panties
off, and then removed the wet diaper, which went into a plastic bag along
with the plastic panties. She produced some baby wipes, and cleaned me up,
again asking me a question. "Does this feel good to you?" "Yes, it feels
lovely!" I replied without thinking. She stood me up, and wiped the sofa
with another baby wipe just to be sure, and asked me to take off the pink
T-shirt. Naked, I once again found myself in front of the mirror.
"Do you like what you see?" I stared for a long time, and finally
turned around and told her what I knew was the truth, "Ella, I like being
Tammy, and I like being pretty, and some day, I hope to be as pretty as you
and Mommy!" She thanked me, and hugged me, and I could feel her breasts on
mine, the soft fabric of her blouse, and knew I had made the right
decision. Ella asked me to get dressed in my girly clothes, and then we
sat on the sofa and we talked about the experience. She reminded me that I
though Mike was a nice boy, but wouldn't want to date him. She asked me
why I thought a boy I wouldn't want to date, was a boy I wanted to be.
That threw me for a loop, and took another Coke, and a half hour to

       We talked for a long time about the way Scott treated me, and she
explained that the problem wasn't mine, but his. He knew who and what I
was, but was too young to really understand what was going on. He was
probably a bit disgusted by being gay, and was really conflicted by his own
thoughts. Scott looked like a real man, but he thought he was much less
than a man, and the fact that I was male, but pulled off the female role so
well really got him thinking about his own masculinity, his own sexuality,
and his own future. "You see, little Tammy, you gave him the perfect
evening, an evening of love, romance, and even sex, and the whole time he
was play acting at being a dominant, heterosexual man. When you took off
your clothes, and he saw the reality, he just couldn't play act any more,
and it depressed him. I wish his parents would take him to a good
counselor to help him understand himself."

       While Ella was calling Mommy, I looked at the clock, and was
shocked to see that I had been here over 3 hours! It didn't seem like it
had been that long. While we were waiting on Mommy, I went into Ella's
private bathroom, brushed my hair, and re-applied my make-up that had been
ruined in several crying jags. I hesitated for a moment, and then locked
myself back in that terrible device. At least this time, the key was in my
purse! I was almost done when I heard Mommy and Ella talking. When I
stepped out, they were holding each other, and kissing passionately. I was
embarrassed, thinking I was interrupting, but as soon as she saw me, she
broke her embrace, and ran to me, wrapping her arms around me, kissing me,
and telling me that everything would be okay now. Ella came over, and put
her arm around me, and told me that anytime I had any more doubts, she
would be here for me, and would help me make my future decisions. That was
a comforting thought, though the thinking of the future sorta scared me a
       Fast forward a few weeks:
"Yes, honey, I know a man who would like to take you out some
evening" Mommy and I were sitting in a little outdoor café, having lunch,
and enjoying both the light summer breeze as it blew our skirts up a bit,
and the stares from men as our skirt moved about our stockinged legs. It
was now mid July, and in the month since my visit to Dr. Ella, things had
been going really well. Our routine was almost that of a normal mother and
daughter. I say almost, as Mommy still put me in diapers and put me to bed
in my crib, and our relationship was a bit more physical than most, but
normal within our bounds. I had agreed to wear my chastity device all the
time, and Mommy would allow me to take it off once a week, so I could "go
cummies." That was mostly me taking care of myself, but I did end up in
her bed one evening, and had a very good time!

       We sat there and talked about me dating again, and Mommy told me
that it was like riding a bicycle, and since I had fallen off, well, gotten
knocked off really, maybe I should get back on and try it again. I finally
agreed to give it one more go, with the stipulation that I was under no
obligation to do anything sexual, if I didn't want to. "Of course, my
little princess! You have to remember that that the woman, or the sissy in
this case, has all the power! You may refuse a man's advances, or fulfill
his wildest fantasies! It's all up to you!" I laughed at that, but filed
that bit of information away. With some apprehension, I also told Mommy to
go ahead and set up my date

The Thursday before my second date arrived. We were up early, and
since I had spent the night in Mommy' bed, we got up together. Nothing had
happened during the night, though, as I was still in chastity, and had
slept in diapers as Mommy's baby. I have to say, it was a beautiful way to
sleep. diapered and snug in my satin nightie, snuggled up to Mommy in her
silk nightgown, and covered by soft satin sheets! Mommy gave me a bath
after removing my diaper, and washed my long hair. We a light breakfast,
and were off to a distant mall, to a very expensive and exclusive ladies
shop. There, Mommy bought me a beautiful deep blue silk dress, that came to
just above my knees. A half slip in navy blue silk, with a gorgeous hem of
lace was added to the purchase, as was a pair of navy blue, real silk
panties with lacy panels, a matching garter belt, black seamed stockings,
and a matching camisole. This dress and the lingerie were sexy,
sophisticated, and I loved them! When Mommy paid the bill, I found out
that I was going to be wearing over a thousand dollars of silk for my date!
WOW! The thought that I couldn't wait to wear these beautiful, sexy
things, and wanted to look pretty in them both exited and scared me. Mommy
then talked to the saleslady for a long time, and finally they both came
back over to me, standing in the dressing room in my new lingerie, and the
saleslady took out a measuring tape. I was embarrassed, and my cock tried
to get hard in my cage, and I felt very nervous. I tried to cover m crotch
with my hands, but there was really nothing to hide!. Both women looked
down, and giggled at my predicament
The time had passed quickly, with only minor infractions on my part.
My ballet lessons had continued through the summer, and were embarrassing,
as the lock on my device could be seen through my skin tight leotards,
although the ruffled tutu skirt mostly hid it. I was getting very good at
ballroom dancing, and the last two lessons were taken on the highest heels
I owned (Excepting the punishment heels), and I managed to get several
compliments from Mr. Lee, my instructor, on how well I followed his lead,
and seemed to glide across the floor like a real lady. For some reason,
that remark both shamed me, and made me proud. I didn't think Mr. Lee knew
I was really a male under my lingerie, and the way he managed to brush my
bottom, and my breasts, and hold his hand just a bit lower than needed
seemed to prove me right, unless he liked sissies too?
As l tried on my new dress, questions whirled though my head like
debris in a tornado. Would I like him? Would he like me? Why did I care
whether I liked him or he liked me? Would I get this chastity horror off?
Would he expect me to do anything more than kiss him, and would I do it?
Should I run away? Does he know what I have under my panties? If not,
would it disgust him or turn him on, and why did I care! As we sat in
little corner of the food court, eating lunch, mommy handed me a note from
Dr. Starnes. "Dear Tammy," it read, "The man you are going out with is a
very good friend of mine, and a gentleman. You have blossomed into a
beautiful young sissy, and should have a very good time with him. Remember
that you have control of what happens! Please have a very good time! I'll
make time to talk to you on the following Monday, if you need to. Love,
Ella." That note "sealed the deal," as it were, and all fears were
forgotten, and now it was just the excitement of a date with a man, and not
a young boy who had more idea of what to do with a lady (or sissy!) than
the man in the moon!

I was finally let out of my crib on Saturday morning, and put up on
the changing table for Mommy to change my diaper. After she took the old
one off, I was told that I would not need a new diaper today, as I was to
be getting ready for my dinner date with Eric. She reached into her pocket
and took out the little heart-shaped key ring that held a single small key.
She waved it in front of me and slipped it back into her pocket. I hated
being teased, and my cock had started, for the millionth time, to try and
swell up again, only to be foiled one more by the CB 3000. I put on a pair
of panties, robe and slippers, and went downstairs for breakfast. We talk
a while about this and that, and then Mommy told me to go upstairs and get
a quick shower and put on something decent to go shopping in. Of course,
decent for Mommy meant that I would wear a skirt, blouse, and heels. No
slacks for this sissy, and besides, the only slacks I had were very tight,
and I was sure the outline of the lock would show through. A short time
later, I came downstairs, wearing a plaid skirt, tan stockings with a white
garter belt, and a white cotton blouse. I again looked like typical teen
girl from 1955.
Our first stop was to the beauty salon, where I had my hair trimmed
and styled. She did a layered thing with bangs, and kind of a flip at the
end of my shoulder length hair. From there, it was on to the mall. I was
no longer worried about going out as everyone seemed to accept me as a
young girl. Most guessed my age at around 13 or so, and no one seemed to
think I was anything but a prissy little girl. I wasn't sure if I liked
that, but on the other hand, if anyone found out that I was a boy, dressed
like a girl, with my cock in a pink chastity device...If they found out I
slept in a crib many nights, wearing diapers and plastic panties...If they
found out I allowed my mother to do these things to me without
protest...You see, it could be a lot worse! Anyway, once in the mall, we
made a beeline for the nail salon, where Mommy told me I had an
appointment. Once there, I was treated to the works. I was given a
pedicure, and my toenails were painted in a dusty rose color, My nails were
examined carefully, to see if I needed to use false nails. I had been told
to let them grow, and had tried to be very careful with my nails, as Mommy
told me a broken nail might mean my date would be in diapers. Gulp! They
finally decided to file, buff, trim, and paint my natural nails the same
dusty rose as my toe nails. Two hours later, and two careful coats on all
ten toes and all ten fingers, and it was time to go to lunch. We stopped
at a little stand in the mall, and each got a chicken Caesar wrap and a
bottle of water, and then it was back to the house. We sat around,
watching a bit of a TV movie until around three thirty, when it was
announced that I had to start getting ready, now.

First thing was a long, hot bath with scented bath oil. Since I had
washed my hair in the shower that morning, I was careful to not get my head
wet. I went over my "trouble areas" with a lady's razor, which didn't take
too long. Applications of depilatory every few days at first, and then
once a week seemed to make that problem go away. Once out of the shower, I
dried myself off, and used a body cream with the same fragrance as my bath
oil and perfume, slipped into my robe and ballet slippers, and headed for
my "big girl room."

Mommy was waiting for me, and she helped me to roll the silky
stockings up my legs, making sure the seams were straight in back. The
stockings had a large swath of lace at the top, and a band of rubbed
inside, so that they would stay up all by themselves, and they looked
fabulous, but Mommy told me I needed a garter belt to feel sexy and
beautiful like a woman. I picked up the blue silk panties, but Mommy told
me the garter belt went on first, and the panties over the garter straps.
I must have looked at her funny, because she giggled, and asked me how I
would go potty the other way, and what if I wanted to get my panties off
for "any other reason." The lovely silk belt was wrapped around my middle,
adjusted, and then the garter tabs were hooked to my stockings. I could
feel the pull of the straps, and that alone told me how girly I was. I
looked down, and saw, though, not a girl, but a sissy in a chastity device.
How disappointing, yet it turned me on ever so much!

I pulled the silk panties up my smooth legs, and marveled at how they
hugged my butt. I looked in the mirror, and saw now that I looked like a
girl, the chastity device showing as only a little mound, and the lock not
showing at all. Mommy helped me into my bra, with a delicate kiss on each
nipple that almost sent me into orbit! The bra was so delicate that it did
more to show off my new hard-nippled little sissy breasts, than to conceal
them. My breasts had stopped growing, and were now just a little over a B
cup, and I loved them! The camisole slid on over the bra, and I thought
that with two layers concealment would be achieved, but the camisole was so
sheer and lacy, it seemed to make sure that the eye was drawn to my small
breasts. I stood in front of the mirror, swinging back and forth to look
at myself. My bottom looked so cute thanks to long hours of ballet,
hormones, and a pair of very expensive silk panties. My legs in their
sheath of sheer black shiny nylon looked like they belonged to a model, and
I have to admit, made me proud they were mine. Finally, Mommy told me to
quit admiring myself and to finish getting dressed. She spritzed some
perfume on the backs of my knees, my wrists, my throat, and a tiny dab
behind each ear. As a final touch, she gave a tiny spray just above my
garter belt, and just below my belly button. I wondered who would be able
to smell it there, but... I stepped into the slip, and pulled it up around
my waist, and then Mommy slid that wonderful dress down around my
shoulders. It seemed to float on my body. Tight across the bust and
belly, and flowing loose around my thighs. I felt like a princess for real
right then and there! I was sat on my little dressing chair, and Mommy
applied my eyeliner, rouge, and lipstick just a shade pinker than my
nails. (no adult red allowed for a sissy). My shoes were slipped on my
stockinged feet, and the straps buckled around my ankles. Mommy finished
zipping me up, put a short pearl necklace around my throat that came
half-way to the top of the dress, and handed me a matching bracelet. Gold
and pearl earrings were inserted my lobes, and I was done!

Downstairs, Mommy got out the camera and took picture after picture of
me in my grown up dress, ready for my date. I froze when she said that. I
had forgotten all about Eric. This had been me, me, me, all day. I had
been pampered, I was wearing layer after layer of silky clothing, and I
felt so girly and pretty. I had forgotten that this evening would end with
me going out with a man, a man who expected me to be a girl, his girl, for
the evening. My joy was gone, and my legs started shaking. Being careful
not to smudge my make-up, Mommy took me in her arms, and told me how much
she loved me.. She told me that all I was required to do was to be a lady,
talk to Eric during dinner, dance with him, and give him a good night kiss.
That was all. "You dance beautifully, my sweet princess, and you look like
an angel. No one will know you are really a mincing sissy boy, unless you
want them to know. You are allowed to be a lady tonight, and to accept or
refuse any "offers," and that will help you make your final decision as to
whether you want to be Mike or Tammy for the rest of your life. Relax,
enjoy the food, enjoy dancing, and enjoy Eric. I have had lunch with him
four or five times, and he is a sweet boy, and I have to say, he's a hunk!
I wouldn't mind checking out what's in his pants myself! Maybe you'll get
lucky!" I sort of hoped not, but the idea excited me more than I wanted to
let on!

6:30 came quickly, and when the doorbell rang, I almost jumped out of
the wooden chair that I was sitting on! Mommy told me to run upstairs, so
I could make an "entrance." I was amazed that I ran lightly up the stairs
in 5 inch heels with no more difficulty than I would have had in trainers,
but even in heels, I was quieter and more graceful. Huh! Mom talked to
Eric for a few minutes, and I could hear them laugh at something. He had a
nice voice, not too deep, but pleasant, and he had a nice laugh, no
snorting or giggling. I began to relax just a bit, telling myself that I
could get through this, nothing to it. Just then I heard my name being
called. "Are you ready, sweetheart?" my mother called up the stairs.
"Just a sec!" I yelled back. I stood in front of the mirror, and checked
for anything out of place. I shook my head to clear the doubts, and began
that very, very long walk down the stairs.

I was concentrating on how I walked, and not on the two people in the
hall. As I got down the stairs, I took my first look at Eric. He was
about 6'2" to my 5'4" without heels, and looked like he kept himself in
shape. He had dark blonde hair that was cut in conservative style that
really flattered his face. He wasn't rugged in the sense of a lumberjack
or anything, but he was far from the metrosexual man graced the magazine
covers and who starred in teen vampire movies. As I got the bottom of the
stairs, he seemed to take something from Mommy, and slip it in his pocket.
His dark grey eyes were fixed on me, and as I walked to where the two of
the stood, as gracefully as my nerves would allow, Mom took my hand, and
placed it in his. I felt an electric current, as though his hand was a
charged battery. The shock went into my stomach, and farther. I could
feel my little cock, what Mom has started calling my "clitty" trying to
swell in its plastic cage. (I wasn't really tiny, but I have since found
out that five and-a-half inches hard isn't exactly considered a large manly

After I recovered, I took a long look at him. He was wearing a pair
of very nice gray wool slacks with polished black wing tip shoes, a
starched white shirt with an expensive silk tie in a paisley pattern, and a
black blazer. The entire effect was of polished urbanity, and exuded
masculinity like radio waves. After some pointless chit-chat, Mommy handed
me my small black satin purse, and a black Cashmere shawl which Eric draped
over my shoulders, igniting me yet again. He took my arm, and we went to
his car. He held the door for me, and off we went. I have no memory of
the restaurant, or what I ate. I dimly remember a bottle of wine, but
vividly remember his eyes. We talked about who knows what, he paid the
bill, and it was off to a club. I wondered what sort of club we would be
going to, when he pulled his car into the parking lot of the most exclusive
country club in the state! He gave the keys to the valet, and again, took
my arm and led me through the sumptuous door as though he owned the place.
This was too well planned, to be some casual date, and I realized that I
didn't care. This man was beautiful, I felt like a beautiful girl, and
chemistry class was definitely in session! I left my wrap with a girl in
the cloakroom, just like some old movie, and we moved on the ballroom.
There was a real live orchestra playing, and they were really good! Eric
got us a small table, and ordered a bottle of champagne. I was so giddy
and nervous, I drank the glass of wine straight away, and felt it go right
to my head. Eric refilled my glass from the iced bottle by the table . I
knew I had to take it easy, as I was not only underage, but totally unused
to drinking.
After a few minutes, the band finished the number they were playing,
and began to play an old classic. Eric took my arm and led me to the dance
floor. We floated along to Stardust, at first at proper arm's length, and
by the end of the number, I was dancing against his body, my head on his
shoulders. We stayed out for a dance or two, and then it was back to the
table for a little more champagne. Eric held my hand and told me how
beautiful I was, and how well I danced. I know I blushed thirty shades of
red, and told him he was the most beautiful hunk of man I had ever seen! I
think he blushed more than I did! We went back to the floor for the next
number, and I could feel his thickening cock against my stomach, his hard
muscles through the wool of his slacks, and I knew that this was why a
woman wore her panties over her garters. If he would have asked me to, I
would have taken my dress off, right there on the dance floor, and done
anything he wanted!
The final song came much too soon, and we went back to the table to
collect my little black satin purse. Eric took my arm, and then took me in
his arms and kissed me. I melted, and kissed him back with as much passion
as I could muster. He broke off the kiss, and whispered in my ear, "My
darling princess (I jumped at his use of that particular endearment), we
can either get in the car and take you home, whereupon I will turn into a
very sad pumpkin, or we can go upstairs to my suite." "His suite!?" I
stammered, and demurred like crazy. I wanted to go upstairs worse than I
had ever wanted anything, but all my thoughts were centered on what
happened with Scott (damn him!) and on that damn piece of plastic over what
no girl should ever have between her legs. "I, I, I'm not sure I should,"
I began, "I mean, well, I'm not what, I mean, I'm..." here I broke down and
went silent, just staring at the floor in abject misery. Gently, Eric took
my chin in his hand, and raised my head. I wanted to cry so badly, but the
soft smile on his face stopped me. His hand went into his pocket, and he
drew out a small, heart-shaped key ring, with a single shiny key dangling
from it. "I know, Princess, and your mother has given me the keys to your
castle." I looked and heard, but it took me a moment to comprehend. He
knew! He knew not only who I was, but what I was, and Mommy was helping!
I tried to talk, but finally simply melted into him, and hugged that strong
body to me.

Arm in arm, we climbed that wide staircase of polished wood. I knew
we were being stared at, and I made sure that my little bottom twitched
nicely for the men. At the top of the stairs, I bent to adjust the strap
of my shoe which needed no adjustment, just to give the boys at the foot of
the stairs a glimpse of my stocking tops, and the dress tight over my
bottom, and maybe, just maybe, a little flash of panty.. Finished with my
quick tease, I took that arm again, the heat coming off of it almost
burning me, and we went down the long hall to a door marked with a large
brass number 6. Eric pulled out a key, and after swinging the door open,
he grabbed me, picked me up in his arms, and carried me into his rooms.

Even before he set me down, he began to kiss me, and I did nothing to
stop him. I responded to his kiss by molding my body against his, feeling
his muscles, feeling his hard cock, kissing those wonderful lips, and
feeling as female as I had ever felt. I wanted his cock in my mouth, and
realized that for a man, that would be gay, but for a sissy, it was
perfectly normal. Eric broke away, although I tried to hold him close a
little longer, and he reached back into his pocket. He handed me the key,
and told me I was free to go into the bathroom, and unlock my treasure for
him. I grabbed the key, and almost skipped into the bathroom. I pulled up
my skirt and slip, and pulled my panties down. With shaking hands, I
slipped the little key into the lock and removed it.. I worked the hard
plastic tube down off my hardening clitty, and then with some difficulty,
removed the ring from behind my balls. I then took a warm washcloth, and
gently wiped the sweat from my hairless balls and clitty, pulled my panties
up, and lowered my dress. As an afterthought, I reached up under the
dress, and slid my soft silk slip off, and draped it over my arm. I
considered undressing, but wanted to stay as feminine and beautiful as I
could, for as long as I could.
As I walked back into the room, I tossed my slip over a chair, and
resumed my place in Eric's arms. He had taken off his jacket and tie, and
as we kissed, we allowed our hands to roam freely over each other's body.
His hand slipped under my dress, and gently caressed my stocking covered
legs, and then moved up to my panty clad ass. He ran a finger up and down
my crack, making me weak in the knees, and then finally slipped his hand
under the leg elastic. As his bare hand rested on my bare bottom, I knew I
wanted this man, anyway he wanted, I would do whatever he wanted, as much
as he wanted, whenever he wanted. I wanted to be his slave! I wanted to
wear my satin maid's outfit and be his maid, his slave, his possession! I
would even put myself back into that horrible CB3000 for him, and surrender
the keys to him. I was his, body and soul!
He slowly pulled the zipper down on my dress, and I shrugged it off my
shoulders. It slid to the floor and pooled around my ankles in a silken
puddle, and I stepped out of it. Now it was my turn, I undid the buttons
on his shirt, noticing that while the buttons were backwards from a girl's
blouse, my time as a boy seemed to come in handy, as I had no problems. I
pulled the open shirt away from his chest, and ran my hands over his
muscled chest. He reached over and started to undo the cuff buttons, which
I took as an invitation to undo his belt buckle. I thought about the times
Mommy had me do this with her rubber cock under her jeans, and realized how
valuable her training was! I began to unbutton his slacks, my hands
shaking with anticipation. Looking up into those gray eyes, I smiled, and
slid his zipper down, and allowed his slacks to join my dress on the
polished wooden floor. He was wearing a pair of black cotton briefs and I
could clearly see the outline of his cock through the material.
I began to nuzzle his crotch through the underwear, kissing his cock
through the cotton, inhaling the musky aroma, and was rewarded by it
seeming to get harder and longer! Finally, I could take it no more, and
pulled his briefs down, and got my first look at his beautiful cock. It
was almost 10 inches long, and thick! How do I know? I measured it later!
(giggle!) He had shaved his balls, and had just a short tuft of hair above
his crotch. I kissed the huge head, and began to lick and kiss the helmet
of his circumcised monster, and to fondle and lick his balls, just like
Mommy had taught her sissy to do. He let me go on for a minute or two, and
then took my arms and stood me up. He took off his shoes, socks and the
rest of his clothes, and I grabbed his pants and shirt, and hung them over
a chair, along with my dress. I now stood in front of a naked man, wearing
black heels, black seamed stockings, navy blue silk panties, bra, camisole,
and garter belt, with my own, not so big, erection in my panties. I was a
total girl, until you got to my panties, and even though it wasn't near as
big as Eric's, it was there, the 800 pound gorilla in the room. I saw Eric
look at me there, and blushed, trying to cover my sex with my hands. Eric
came to me, and took my hands, kissed each one of them, and knelt at my
feet, and kissed my cock through the silk of my panties. I almost fainted
from this light kiss, and he stood up, took me in his strong arms, and
began to kiss me. He led me to the bed, but as soon as we got the thick
rug there, I slipped through his arms, and resumed my submissive position
on my knees in front of him. I gently took his balls in my hand, and took
his cock into my mouth. Just like Mommy's rubber cock, and my thick cock
gag, he filled my sissy mouth.
But unlike the ersatz rubber dildos, his cock was warm, hot almost.
While he was hard, it was like a satin sheath over an iron rod. I couldn't
get enough of the feel of his cock in my mouth, the light musky scent of
his crotch in my nose, and the taste of his cock. I began to suck him deep
into my mouth, my own cock fighting to rip free of its silken prison. I
took him deeper and deeper, until his balls were against my chin , and my
nose was buried in his short trimmed pubic hair. Thanks to my training, I
had no trouble taking him deep into my throat. He began to breathe
heavily, and went from caressing my hair, to grabbing my head. I slipped a
finger into the side of my mouth, and reached around and slowly inserted it
into his glorious asshole, while sucking his cock as deep into my mouth as
it would go. He began to fuck my mouth, ramming that wonderful cock down
my throat, and then pulling back out until it seemed that my sucking was
the only thing that held it in my lips, and then slamming it deep again.
It only took a few minutes until I felt his balls tighten, and he gripped
my head like a vise. His cock, thick, long and hard, seemed to swell up
even bigger, and then with a loud moan, he shot a load of salty warm cum
into my mouth. I swallowed what seemed like a quart of his sperm, sucking
all the time to get the last drops of his manhood into my sissy
mouth. Finally, with a shudder, he pulled his softening member from my
mouth, pulled me to my feet, and began to softly kiss me, tasting his own
cum from my mouth.
He just held me tenderly, kissing my lips, my forehead, my eyelids, my
cheeks. Finally, he broke away, and went to a hook over the door and
pulled on a paisley silk robe, and then, taking my hand, led me over to a
small sofa. Beside the sofa was a silver bucket filled with ice and
another bottle of champagne. In my lust, I hadn't seen the sofa, or the
bucket, and now wondered who put it there. As he filled my crystal flute,
I looked around. The bedroom of his suite was huge, about 20 x 20 foot,
and as elegant as any room I had ever dreamed about. The walls were
painted a brick red, with several very nice prints, framed and lit by brass
lamps over them. The bed itself was a king size bed of black walnut, and
the nightstand and dresser matched. These must have been antiques, and
very expensive ones! The deep Persian carpet by the bed was the only
covering of the honey-toned oak floor, and the woodwork around the door,
closet, and the windows was dark and beautiful. This was a man's room. No
sissies here, well, except me.
I took my eyes away from the room, and put them back on Eric. He was
holding a flute of champagne out to me, and on impulse, I kissed his hand
before taking it. Without even thinking about what I was saying, I blurted
out, "But I should be serving you, Master!" Eric chuckled, and told me
that if I really wanted to, there would be time. But for now, he wanted to
get to know his sissy princess, make love to his sissy princess, and then
fuck his sissy princess. Every time he called me "his sissy princess," my
clitty jerked in my panties, and I felt all fluttery in my belly. I
wanted, no needed to be his sissy, to be his servant, his very slave. He
looked into my eyes, and I knew he could see what I was thinking. He took
my glass from me, and set it down on the leather covered coffee table, and
led me to the bed.
He pulled the bedspread back to reveal black satin sheets, and had me
sit on the edge of the bed. He then got to his knees in front of me, and
began to kiss my silky panties, making my clitty jump and dance. Slowly,
he began to pull my panties down, and I lifted my hips to help him. He
then pulled them off my feet, and stood up. I was almost screaming from
the frustration! I wanted him to take me in his mouth, and he was standing
up? He stood me up, and then slipped the straps of my camisole down over
my arms, and let it slither to the floor. He unhooked my lacy silk bra,
and it followed my camisole. He took me in his arms, and began to nuzzle
and kiss my tender swollen nipples, gently biting and kissing them,
caressing my ass with his free hand, but like a sadist, not letting his
hand stray anywhere near my poor, swollen, neglected clitty . The clitty
that had been locked away for over a week with no attention, and no
opportunity for relief.
He took one hand, and opened his nightstand drawer, and pulled out a
pair of handcuffs. He handed them to me, and told me I must submit to him,
by cuffing my own wrists behind my back Without a word, I snapped the cuff
onto my right wrist, and putting my arms behind me, I, with some
difficulty, managed to get the other cuff secured to my left. With that,
he pushed me back onto the bed, and withdrew something from under the bed.
He began to put a cuff on my left ankle, and then my right. He gently
spread my legs, and attached a spreader bar between my ankles, forcing my
legs to go wide. Here I was, wearing only heels, stockings and a garter
belt, bound on black satin sheets, with a hard-on poking up between my
garter straps. When I was helpless, laying back across his bed, cuffed
hands under me, my spread feet heels, flat on the floor, he again knelt
between my legs, and finally took me into his mouth, he started to suck,
but just as he would get a rhythm going, a rhythm that would allow me to
cum quickly, he would stop, and kiss my balls, kiss around my clitty, until
I wanted to scream! I kept trying to hump his mouth, and begged and begged
to be allowed to cum, but his only reply was to go once again to the
nightstand, and bring out my very own cock gag! Mommy must have given him
all the information along with some toys to play with! He buckled the gag
into my willing mouth, and went back to slow, and frustrating ministrations
to my clitty. It felt like wonderful, horrible, fantastic hours passed,
when he suddenly began to suck my cock, my sissy clitty, into his mouth.
Harder and faster he sucked, and with a blinding, aching, back arching
orgasm, I filled his mouth with my sissy cream!
He released me from my bondage, removed my gag, and kissed me. I
realized then that he had never swallowed, and we shared a cummy, sweet
kiss. I was given a beautiful black satin robe to put on, and we went into
the next room, taking the rest of the champagne with us. He picked up a
phone that had no buttons or dial, and was obviously not an outside line,
and ordered a second bottle of champagne, some cheese, pate, fruit, and
crackers to be sent up. He told me that the rooms were like hotel rooms,
except that each member who had one passed it on to his sons, and they were
furnished by the occupant to their taste. Rent, room service, maid
service, etc. were paid for on a quarterly basis, along with dues and
greens fees and the like. I wandered around this beautiful room. There
was a large French door that led out onto a balcony, itself overlooking a
small lake and a portion of the golf course. There was a small galley
kitchen, table, 4 chairs, two leather easy chairs, a leather sofa, large
flat panel TV in a cabinet, and one wall was all shelves full of books and
expensive bric-a-brac. While the bedroom was done in red, here the
woodwork extended up to about 6 foot, and the rest of the wall was painted
ivory. The floor was the same medium oak, while the rest of the room was
done in either dark oak or cherry. These were the most extravagant and
luxurious rooms I had ever seen, and these were nothing but a home away
from home for this man!
The girl who delivered the food was very, very cute, and dressed in a
shiny, form-hugging black satin mini dress and heels. Eric thanked her,
handed her a bill that must have been large, at least I thought so from her
reaction, and as she was leaving, gently grabbed a handful of her beautiful
ass. He asked her if she could stay and play, and she just giggled and
wiggled her way out in a most delicious manner. I, of course, felt hurt.
Did he want a real girl more than me? Of course he did, I raged, no man
would want a sissy when there was a genetic girl, a beautiful girl, who
didn't get upset when her pantied ass is grabbed, kind of girl around.
Eric must have read my mind, because he came up behind me, wrapped his
arms around me, and began to kiss and nibble on my neck. his hands ran
down the front of the robe, caressing my nipples, and on down until they
came to my clitty, which was already getting hard again. I put my hand
behind me, and felt his cock stiffen in my hands, ready for another round
of fun. Eric turned on some music, and we danced a bit, grinding our
bodies into each other. We each had another glass of the bubbly wine,
finishing that bottle. Eric led me back to the bed, and asked me if I was
ready to lose my virginity.
I kissed him and told him that even if I wasn't, it was his to take
whenever and however he wanted it! He smiled gently, and told me to take
off my robe. He kissed my nipples, working his way down to my belly, but
stopped just before my clitty. He undid my garter belt, and asked me to
sit on the bed. He again knelt in front of me, and began to remove my
shoes. I protested, telling him that I wanted to keep some lingerie and my
shoes on to make me feel girly. He told me not to worry, as he had that
covered. He took off my shoes and hose, and then when I was naked, he told
me to open the closet, and put on what was in there. I expected a
nightgown, or something, but when I opened the closet, I was hit again with
the fact that my seduction had been planned to perfection!
Hanging in front of me was the shortest, sissiest, frilliest white
dress ever a sissy could wear! It was trimmed in baby blue ribbons and
bows, and for all the world, looked like a wedding dress fit for a sissy!
I pulled it out, and realized that this was a hand-made, very expensive
dress! It had built-in petticoats, and was completely beautiful! I took
it out, and lay it on the bed. I next found a box wrapped in pink paper,
with "Tammy" on it in calligraphy, so I took it to the bed and opened it.
Inside was a pair of white, double layer, satin panties, trimmed with
lashings of white lace, and two delicate baby blue ribbon bows. I held
them up, loving the look and feel of them, and as I was turning them in my
hands, I saw that there was a lace trimmed hole in the backside of the
panties, right about where my bottom was! I knew what that was for, and
immediately dubbed these my "submission panties, and slid the soft frilly
creations up my legs.
Another look in the box, under a layer of pink tissue, the matching
training bra was nestled. Under yet another layer of tissue, I found a
pair of white nylon ankle socks with baby blue lace trim. Beside them were
a pair of white fingerless satin mittens with lace around the cuffs, and
blue ribbon to tie them tightly onto a sissy's hands. At the bottom was a
small lace trimmed satin apron, in baby blue glass silk, with a baby blue
ribbon to tie behind my back. I looked in the closet one more time, and
found a pair of white, baby doll pumps with locking ankle straps on the
floor. In a skinny minute. the socks were on my feet, the shoes locked on
over them, and I was hooking that beautiful training bra over my small
sissy tits. I stepped into that heavenly dress, pulled up the zipper, and
adjusted the petticoats. I saw at once that this sissy. lacy, satin dream
of a dress wasn't even long enough to cover my panties, even if I tugged it
down! I pulled the tiny apron on, and using the mirror, made a nice bow in
the back. I then took out the mittens, but before I put them on, I thought
for a very, very long moment. My man wanted me to be his sissy. I wanted
to be, not only his sissy, but his subservient sissy slave. I knew what I
had to do.
I opened the nightstand drawer where I had seen Eric place it. I
stared at the pink plastic horror, and knew that it was right. Tonight,
only Eric mattered, and what I wanted made no difference. I pulled down my
panties, fluffed out my skirt, and sat on the edge of the bed to get the
damn thing on me. I struggled and twisted, and finally got the ring behind
my balls, and the plastic tube on over my clitty. With a final sigh, I
clicked the lock into place, and dropped the key back in the drawer. and
went to my purse on the nightstand. I put a fresh coat of lipstick on,
this time very sissy pink. He never said I was to be restrained, but how
else do you take a sissy? With that done, only a few things remained to be
done. I took the penis gag out of the drawer, and buckled it carefully
into my own mouth so I didn't smudge my lipstick. I walked around the
room, lighting several candles that were there, and turning down the
overhead dimmer until it was barely on. I then took the handcuffs, placed
them on my wrists, with my hands in front of me, pulled on the thick satin
mittens, and stood in the center of the room. I now waited on my lover,
and my master.
I stood there on shaking legs for about ten minutes, hoping my Master
would approve of me, when the door to the bedroom finally opened. Eric
stood in the light streaming from the other room, holding a champagne
glass. I couldn't see his face, but he quickly closed the door, gulped
down the rest of the wine, and set the flute down on the table. He came to
me, gagged, restrained, and waiting, and just stared. He walked around me,
lifting my short skirt and crinolines to see my pantied ass. He gently
touched me, my face, my tiny sissy titties, and then, he got an odd look on
his face. He reached down, and with one hand, pulled up the skirt of my
sissy dress, and with the other, he pulled the front of my panties out.
Looking at my restrained sissy clitty, he began to laugh. Not an evil
laugh, but sort of a private joke laugh. He took me in his arms, and began
to kiss my face and neck, his hands roaming over my back, pausing to caress
my breasts and face, and then holding me tight again. I wanted to hold him
and kiss him, but due to my own initiative, I was helpless. He stood back
from me, and stared for a second, and then, taking my arms, he pulled them
up, and told me to hold it right there while he tied the mittens tightly
around my wrists. He went to the bed, and reached into that nightstand
drawer for something I hadn't seen.
He stood behind me, and wrapped a wide, lace trimmed, white leather
choker around my neck, just tight enough for me to know it was there, but
not tight enough to hurt. He then took the handcuff chain, and attached a
very short cord to the chain, and then to a D ring on the front of the
collar. Once I was secured to the collar, he asked me if he should call
room service again, as the young lady was rather cute, and would probably
be lots of fun for him in bed. "Of course," he said, "you would be tied up
so you could watch all the fun." I started to shake my head, but merely
bowed it as much as I could, staring at the floor. It was whatever Eric
wanted, no matter what. "I suppose, "he seemed to muse," that if my virgin
sissy princess went to all this trouble for me, maybe I should forget about
room service, and just "service" the sissy I have in my room."
Laughing at me gently, he led me to the bed, and told me to get on the
bed on my knees. I did so, and he pulled the spreader bar back out from
under the bed, and I think he opened it even wider, if possible, buckled it
to my ankles, and spread my legs so wide they almost hurt. He began to run
his hand over my panty covered ass, stopping every so often to slap me on
one cheek or the other. He took another strap, and connected the center of
the spreader bar to my collar, and pulled me down, hard, onto my forearms.
I was now totally helpless. With my spread legs, I couldn't even roll out
of the way if I wanted to. I was perched on the bed like a sissy tripod!
He picked up a butt plug, and walked around the bed to stand in front of
me. He told me to look at him, and he allowed is silk robe to slide to the
floor. With some difficulty, I lifted my head to look at him. His
beautiful body was naked in front of me, and his cock, while still only
partly erect hung heavy between his legs. He held the plug in his hand.
"This, my little sissy," he said, now pushing the pink plug in my face,
"This is the little starter plug that your Mommy pushed up your cute little
bottom, the one you cried and screamed about so very much. You thought it
was far too big for your widdle sissy bottom, and even though you were
gagged, the whole neighborhood could hear your widdle sissy screams for
Mommy to stop." I was red with shame and humiliation. Eric seemed to know
all about my sissy training! I wanted to die, but for some reason, my
cock, my clitty, was making new efforts to break free of the plastic sheath
that held it in a death grip. He now held the plug next to his own cock.
My eyes went wide at the comparison! "That's right, sissy, Your sissy
mouth was used to the wide gag, and your Mommy made you practice your cock
sucking skills on a dildo, but no one ever prepared your sissy ass for a
real, thick, man's cock, did they?" I began to feel waves of panic wash
over me. He would surely split me in half with that huge manly cock!
I was shaking in anticipation of both pain, and the need to be
submissive, the need to serve this man. I had gagged and restrained
myself, no one else had. I was the one who put on the lingerie. I went
out on the date, and I was the only one who could have stopped this. Mommy
had even given me several opportunities to quit, and I never used them.
Since my "Prom date," I had never complained about the sissy clothes, the
sissy bedroom, the nursery, the diapers, the dildo training, none of it.
Now, I was helpless, dressed as a total cock sucking sissy, completely
restrained, gagged, and chastised, waiting to be fucked up my ass by a man.
He watched me squirm, and saw the humiliation on my face. He seemed to
know how much I was struggling, and that caused his cock to swell, to rise,
to become the rampant beast that would soon deflower my virgin sissy
backside. He looked at me for a moment, and softly asked, "Are you ready
for this, Tammy? Are you very sure you want this? All you have to do is
shake your head no, right now, and I will untie you, and we will have some
other kind of fun tonight." I stained my head to look at this beautiful
man I knew the answer to his question, and I think he did too. So, with
pleading in my eyes, I nodded my head yes, as much as I could, and tried to
yell, "Yes! I want you in me!" around the gag.
Eric now stood walked around the bed, stood behind me, and began to
stroke my bottom. He ran a finger up and down my backside, making me
shudder. He reached around and grabbed my balls, but not hard, which
caused me to whimper into the gag. He stepped away, and I felt something
hard push into my bottom, It was cold, so I knew it wasn't Eric's monster.
he pushed it in and out a few times, and told me he was just applying a
little lube to my sissy hole. I tensed up, and he slapped my ass, HARD!
"Relax, you effeminate little bitch! You're going to get the cute little
sissy ass of yours fucked, but the more you tense up, the more it will
With those words, I felt his hard, hot cock at the entrance to my ass.
Holding my hips, he began to push, forcing the head of his cock into, and
then past my sphincter. I screamed, yelled and squirmed, and begged
through my gag for him to stop, but he pushed his cock into me, slow and
steady. I could almost feel the blood pulsing though his cock, and even
though it hurt so badly I wanted to die, I wanted more and more of his
thick member up me! I wanted him to fill me with his cock and I never
wanted him out of me! Finally, I felt his body push against my ass, and I
knew he was all the way in. Slowly, he pulled almost all the way out, and
then without warning, he slammed it back in again, his balls slapping into
my panties. Faster and harder he fucked me, and I began to hump him back.
I couldn't bear the thought of that wonderful cock ever leaving my ass, and
wanted him to keep fucking me all night! He almost did! Thanks to a
masterful blowjob by a talented sissy, he lasted almost five minutes
pounding my little bottom. When he finally grunted, and slammed once more
against my body, filling my bowels with this cum, I almost cried because I
was so sad to feel him begin to shrink. He stayed there, his softening
cock in my ass, resting his sweaty body against my sissy satin clad one,
and telling me that I was the sweetest sissy he had ever seen. He finally
pulled out, and then he slipped a tampon up my distended hole to keep the
leakage off the bed.
I was exhausted and cramped, but all he did was slap my poor bottom
again, and head for the bathroom. I heard the shower running, and then
shut off, I could hear him humming to himself, and then he came out of the
bathroom, still drying his hair. He walked around the bed, picked up his
robe and put it on. The whole time he didn't look at me with any more
interest than he would have the lamp. Finally, after he had poured himself
the last of the champagne, he wandered back in, and began to release me
from my sissy prison. He helped me up off the bed, and began to caress and
kiss me, holding my satin encased body against his, telling me how happy I
had made him. He sat me down on the bed, and with the gentle hands,
removed the CB 3000 from my aching clitty. He kissed the head of my now
hard pee-pee, and told me that we would have a little nightcap, and then a
special friend was coming to help get me ready for beddy-byes. I had no
idea who that might be, but I suspected that cute little blonde who had
brought room service. I also was slightly worried that it might be Mommy.
I really didn't want to share this man with anyone, but just before I
protested, I remembered my little promise to myself that I was here to be
submissive in every way to this wonderful man. I looked at the floor, and
murmured, "Whatever you wish, Master." He smiled and kissed me again,
A short time later, Eric called down for room service yet again. I
looked at the clock, and with a start, saw that it was well after one in
the morning! With soft jazz quietly playing on the stereo, and a full
night of dancing, dining and sex behind me, I was worn out. I had been let
out of my bondage, but Eric wanted me to keep my little white satin sissy
dress and such on, including my heels and mittens, as he thought I looked
so cute. Right now, I felt like a little girl who wanted very much to
sleep. The fourth (or was it fifth?) bottle of Moet champagne he ordered
didn't appeal to me too much. If he was going to take me home, I hoped he
would do it soon, if not, I wanted to get undressed and go to bed. I
should have known that the evening's entertainment had one more act before
the final curtain.

A soft knock at the door, and in walked the blonde from earlier that
evening. I now took a good look at her. She had long, shapely legs, deep
cleavage, and looked ravishing in that tight, very short, and very shiny
black satin mini dress and heels. I now noticed that she was also wearing
a black lacy satin choker, and matching wristlets, and with just a few
small changes in her wardrobe, she could have been a bunny at the Playboy
She came in, and set the bottle in a fresh silver bucket beside Eric's
chair, and opened the bubbly beverage. She poured him a flute, and to my
surprise, poured one for herself, and sat in his lap! She looked like a
sleek, beautiful, and very contented Siamese cat, and if she had purred, I
wouldn't have been surprised. She looked me over, and then in a soft
southern accent, told Eric that she thought I was beautiful, and that the
sissy dress he bought for me was the most exquisite little thing! I
blushed and hung my head. She uncoiled from Eric's lap, and the grace of
that movement again reminded me of a pure bred feline. She asked me to
stand up, and she looked me over. Standing behind me, she pulled up my
skirt, and giggled over the lace covered access hole, and then lowered my
dress. She shocked me by wrapping her arms around me, and gently fondling
my sissy tits, making me moan with excitement. With one hand still on my
tiny breasts, she moved the other hand down to my satin covered clitty, and
began to rub me though the panties. I responded by getting hard yet again.
This caused her to giggle and she asked Eric what we should do about "our
little girly here, with the hard thing in her pretty panties!"
Without waiting for an answer, she began to rub my clitty through the
panties again. I didn't know what was expected of me, so I just stood
there and enjoyed the attention. "You know, Heather," Eric said,
addressing the beautiful blonde, little Tammy here has been such a
wonderful sissy date for me, that I think we should help her enjoy herself
before bed." Heather began giggling, and I was led back into the bedroom.
I was laid down on the bed, again with my feet on the floor. Heather knelt
between my legs, and began to kiss my clitty through my panties, and Eric
crawled onto the bed beside me, and began to kiss me, and to fondle my
little breasts through the layers of satin and lace. I was in total Sissy
Heaven! Heather pulled my panties down, and took my little pee-pee into
her mouth, and gave me a most professional blow job. Between her talented
mouth and hands, and Eric's tender ministrations, I tensed up and released
my second load of sissy cream that night into Heather's sweet mouth.
They both stood me up and undressed me, and Eric told me to go in and
take a shower, and then they would get me ready for beddy-byes. I looked
at him, and he told me that my "Mommy" already knew I would spend the night
here if everything went well, and if I wanted to. I ran over to him, and
wrapped my arms around him. Kissing his lips, I whispered in his ear that
wanted to stay here all night, and for the rest of my sissy life.
I took a long hot shower, wrapped a towel around me, and went back out
into the bedroom, Heather was in Eric's arms, and wearing nothing but black
heels, hose, and garter belt. The choker and wristlets were still in
place, and the look of all that black against her milky white skin was
incredible! I felt a huge stab of jealousy, but as soon as Heather turned
and saw me, she grabbed me and began to kiss me. Eric came up behind me
and pulled down my towel, and wrapped his arms around both of us. This man
must be part stallion, because he was hard as a rock, again! We broke
apart, and Eric asked Heather if she wanted to get me ready for
bed. Breaking into big grin and a giggle, she told me she would love to!
I was `escorted" to the bed, and saw "the final costume change of the
final act." There on the bed was a diaper, plastic panties, a pink satin
diaper cover, and an over-the-top, lace encrusted, satin baby doll
nightie. Of course, the bonnet, fingerless satin mittens, and booties were
there too. She laid my down, and made a big show out of kissing my little
pee-pee, and then powdering me before fitting the diaper with its thick
doubler pad tightly around me, and putting in the oversize diaper pins.
She pulled the crinkly, noisy plastic panties up and over the diaper,
making sure it was all tucked in for no leaks. My booties were tied onto
my ankles, my mittens on my hands, and the soft, lace covered satin gown
pulled over my head. My matching satin bonnet with the beautiful lace trim
was tied under my chin, and voila! From glamorous, romantic young lady, to
bound sissy, to adult sissy baby all in one night. I was led to the bed
and told to lie down. I wanted to sigh in complete contentment, but Eric
interrupted my thoughts. Curiously, he was carrying a sauce pan in his
hand, and there were two baby bottles in it. He told me that there was
warm water in the pan to keep my bottle at the right temperature for a
widdle baby to dwink fwom. All I had to do was choose the pink or the
blue. I had no idea what the difference would be, and chose pink as it
matched my outfit. I was handed the bottle, and Eric said a strange thing.
I had to drink the entire bottle, with no comment or complaint, or he would
turn me out, dressed just as I was, and I would have to find my own way
home. That sort of scared me, and shaking, I took the warm bottle with
both useless hands, put the nipple in my mouth, turned the bottle up, and
began to suckle. I almost spit it out and threw the bottle away. It was
full of PISS! "That's right, widdle sissy," Heather giggled, "You chose
the pink bottle, so you get to drink my pee! If you had chosen the blue,
you would have had a bottle of Eric's pee! Aren't you such a lucky little
sissy that you get such an intimate beddy-bye bottle!" I have to admit,
that while the thought disgusted me at first, it began to turn me on, and I
quickly drained the bottle of pee, and let the empty bottle drop from my
hands, I could taste the salty, acrid pee in my mouth, and after an evening
of being fucked up the ass, sucking a man's cock, and dressing like both a
woman and a sissy, it seemed to be a proper ending.
With that, Heather kicked off her heels, and Eric turned off the
lights, and shed his robe and slippers. They climbed into the bed beside
me, and Heather lay down, and Eric began to kiss her breasts, moving down
across her belly, and then kissed her glistening sex. She arched her back,
and Eric went to town with his tongue, bringing to orgasm at least twice.
I took the opportunity, and used my mouth and bound, satin encased hands on
her beauriful breasts. Finally, he moved up, pushing me aside and slipped
his huge cock into her soaking wet pussy, and rode her to yet another
orgasm, as he climaxed for the third and final time that night.
With the candles guttering, we all snuggled together in the king size
bed. I fell asleep between them, my satin clad left hand on Heather's
breasts, and my right hand, behind me on Eric's finally spent cock. I
never wanted to be Mike again. I would be Tammy, or more precisely, Tammy
the Submissive Sissy for the rest of my life.

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Nifty - Transgender - Control - My Mommy Made Me A Sissy