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Nifty - Transgender - Teen - Sissy Boys Story

Date: Wed, 5 Feb 2003 16:23:21 -0800 (PST)
From: Bill <>
Subject: A Sissy-Boy's Story

A Sissy-Boy's Story
by Bill

I guess I had always been a sissy-boy, but this is the story of
how I evolved -- at the tender age of 13 -- into a full fledged

From the time I was very young, I've known I was "different".
I was fascinated with women's and girls' clothing and shoes. Like
all little sissy-boys, I loved girlish "dress-ups". But I
didn't have to sneak my mother's adult-size clothing, because I
had a sister who was my same size -- my fraternal twin. And she
didn't even mind when I tried on her things! I'm Christopher, by
the way, and my sister's name is Andrea. I usually went by
"Chris"... but when she and I were alone, and I was being girlish
(which was often), I got a special thrill out of being called

Looking back on my boyhood, I laugh at how much of a
stereotypical little queer I was, right from the start. I was
flamboyant in my speech and gestures, and feminine in the way I
ran and threw a ball. I adored playing with Barbie dolls and
combing their hair. When people asked what I wanted to be when I
grew up, I said "fashion designer"!

Even in the early years of elementary school, none of the boys
wanted to associate with me, and as a result I was always
something of a loner. Fortunately I got along OK with some of the
girls... and with Andrea, who was my only real friend. Andrea and
I looked surprisingly alike... not just because of the close
family resemblance, but from the fact that we had nearly
identical hair styles. This was the mid-1970s, and long hair on
boys was actually stylish. I let my straight, silky, light-brown
hair grow down to my shoulders, parted down the middle... just
like Andrea's. Stylish or not, I still got teased all the time
about looking like a girl.

The ironic thing was than Andrea was kind of a tomboy when we
were young, and wanted everyone to call her "Andy" when she was
around 10 and 11. She didn't really care about the dresses that
Mom and both grandmothers bought for her. The good part of that
was that she never cared when I took them to my room to wear
them. I remember the exquisite burgundy velvet dress she got
when we were 10. She wore it exactly once, but I wore in dozens
of times, modeling in front of my bedroom mirror, wearing Andrea's
patent leather shoes and lacy ankle socks, loving the way the dress
rose up when I twirled.

Andrea and I shared a wing of the house that was well-separated
from my parents' room. We were in and out of each other's
bedrooms constantly. Whenever Andrea got a new dress or night
gown, she'd always let me try it on. She didn't even mind me
wearing her panties, which I always thought were so much nicer
than my boys' underpants. Sometimes we'd play a game where Andy
would wear my clothes too, right down to the cartoon-character
briefs, and she would pretend to be a boy. Whenever we "played
house", Andy was the father and I was the mother!

We weren't at all modest about seeing each other nude, since we
took baths together all through childhood. And we sometimes
engaged in naive pre-adolescent sex-play... practicing kissing...
touching each other's private parts... "playing doctor". I was
fascinated with her girl-slit, and she was equally interested in
how my penis would stand up like a little thumb when she played
with it.

One time when we were playing doctor, we decided to take each
other's temperature... anally, just like Mom had done when we
were young. But instead of using the rectal thermometer, we used
a smooth ballpoint pen with a rounded end. It felt so good,
sliding into me on a coating of vaseline! (She didn't like the
feeling when I did it to her.)

After discovering the fun of anal play, I experimented on my own,
exploring my bottom-hole and pretending it was a girl-slit. This
was when I was 10 and 11, and my ass was the center of my most
intense pleasure sensations... much more so than my little penis.
Besides a finger (or two... or more!) I used a variety of toys,
but my favorite was the smooth plastic handle of a hair brush...
about 4 inches in length, an inch diameter, and oval-shaped with
a rounded end. One time I talked Andrea into sliding it into me
as I lay face-down on the bed with my ass raised up, clutching a
pillow to my chest. I begged her to slide it back and forth
inside me, but she thought it was gross and only fucked me for
less than a minute. After that, I kept the activity to myself.

About the time we turned 12, Andrea entered puberty. This caused
a variety of changes in our relationship. She was much more
private about her body; she became interested in boys (and them
in her) and stopped being a tomboy; and finally, she acquired a
selection of bras that I could try on! At first the bras were
padded when she only had puffy nipples standing out from a flat
chest. But soon she had developed pert little breasts that
actually filled the cups of a bra. (I stuffed these with tissues
when I wore them.)

A little while after, I started to develop as well. The first
sign was that my little ball-sack got fuller and started hanging
down lower. By the beginning of 7th grade, my penis was getting
plumper and longer when it was stiff, though still boyishly small
when it was soft.

In junior high school (just 7th and 8th grades back then) Andrea
was in the "popular" group at school... unlike me, since I was as
shy as ever. In addition to flirting with boys and trading
gossip with the most popular girls, she was also getting invited
to parties... even ones given by 8th graders. When we were
younger, Andrea and I would tell each other everything. But now
she was getting more secretive, especially when I asked her to
tell me all about the parties. She'd tease me with tidbits about
how the parties usually had a "make-out room" -- typically a
nearly-dark basement rec-room where boys and girls paired off to
kiss and feel each other up. Although she never gave me any
details about what she did and with whom, sometimes I was told
about what she saw other kids doing in the dim light. And one
time she couldn't help blurting out a detailed description of how
a certain 8th grade cheerleader got drunk on beer, stripped down
to just her panties, and -- with everyone watching -- got on her
knees and actually sucked the stiff penis of Brian Watson, the
most handsome and popular boy in the 8th grade. (He was one of
the boys at school that I had a secret crush on... staring at him
in the hall and on the playground... daydreaming about being his

The hormones of my impending puberty were starting to kick in,
and I was getting my introductory sex education from the stories
of adolescent make-out activities reported by Andrea. My
fantasies started taking on an overtly sexual context for the
first time, and then took a massive leap forward when I found a
pornographic paperback novel on the side of the road. It was
battered from being run over and missing its cover and some
pages, but it contained incredibly explicit scenarios of college
students fucking and sucking in a fraternity house and having
lesbian sex in a sorority. The descriptions... and the raw
vocabulary of pornographic sexuality... burned into my brain and
energized my body as I read them over and over. But I wasn't
identifying with the college boys in the story, with their
muscular bodies and big cocks. Instead, I was fantasizing that I
was a sexy, slutty co-ed, whose nipples got "hard as cherry pits"
(according to the porn book), and whose hot pussy dripped with
"honey" when a boy put his hand in her panties and his finger
slid into her slit. And the way the girl characters always
worshiped a boy's big stiff cock made me want to do the same
thing, getting on my knees to suck a handsome stud... or on my
back to be fucked.

The idea of doing sexual things with a handsome boy captivated my
imagination, and my eyes constantly fixed on the most desirable
boys at school -- usually the most mature athletic types. I
wished it had been ME at that party, sucking Brian Watson's cock!
I experimented sucking my fingers or thumb when I was alone in
my room, before moving on to various appropriately-shaped
objects. I also tried - without success - to suck my own cock,
which was now almost 4 inches when stiff. My cock-substitute of
choice was an uncooked hot dog (for non-American readers, that's
a sausage of about 13 cm). It seemed perfect, and I could eat
the evidence at the end of my imaginary play!

In my room at night, with the lights out, I played out fantasy
scenarios in which I was a pretty girl, alone with a handsome,
horny boy. Sometimes my brain generated an image of Brian Watson
or some other boy from school. Other times I imagined teen
celebrities like Shaun Cassidy or Leif Garrett or Andy Gibb.
The fantasy was particularly intense if I was dressed in Andrea's
clothing. I imagined my "boyfriend" hugging and kissing me and
telling me how pretty I was. Inevitably, he'd be sliding his
fingers up inside my bra to play with my budding tits... though
of course it was really just my own fingers eagerly making my
tiny boy-nipples stiff. And then I imagined him telling me to
strip off my clothes and get on my knees to give him a blow-job.
Kneeling on the floor beside my bed -- imagining him standing
above me, his pants pulled down -- I held the smuggled hot dog
against the mattress at an upward angle and let it glide between
my lips. Flicking with my tongue, I sucked all along the 5-inch
length, eventually being able to take it past the entrance of my
throat, just like the porn novel talked about.

As I sucked, my plump pre-adolescent penis would get rock-hard,
and I'd hold it in my hand and squeeze it gently. (I was so
naive... I still didn't know how to masturbate.) After a while
I'd switch to anal play, imagining the boy coaxing me onto the
bed and stimulating my "pussy" with his fingers to make me hot.
A hot dog didn't work for fucking, of course, so I kept using my
old faithful hair brush handle... lying on my back with my legs
pulled back, or face-down with my ass inclined upward... reaching
around to stroke it into my bottom-hole until I was exhausted and

In the late Spring, just about the time the 7th grade year ended,
Andrea and I were hanging out in my bedroom with nothing to do. I
said "remember how we used to play that I would be a girl and
you'd be a boy? Wanna do that again?"

After some coaxing, she finally agreed, and we got dressed. She
wore my khakis and a button-down shirt and tie. I put on her
smoothest satiny panties, one of her mini-skirts, a bra, and a
frilly white blouse. She had some lipstick (the only make-up she
was allowed to wear), and I carefully applied it to my lips... a
skill at which I was becoming accomplished. She tied her hair in
a ponytail and stuffed it under her collar. This was perfect!
I acted like a flirty girl, and she was a macho boy... my
boyfriend "Andy"!

"Show me what happens when they turn off the lights at a party,
Andy," I begged. We lay down on the bed, and it was like my
fantasies were coming to life as she french-kissed me and slid
her hand along my ass and up my inner thigh. Soon, Andy was on
top of me, humping between my wide-spread legs as I urged her on,
talking to her as if I were a girl and she a boy. With my
mini-skirt bunched up to my waist, and my legs wrapped around her
slender hips, Andy's crotch was rubbing deliciously against the
4-inch boner that was bulging inside my satin panties. I think
she was getting off on it too!

Then I took a chance and said "Andy; remember when you slid the
brush handle into my pussy? Would you do it again? Please? Would
you fuck me with it, good and hard, and I'll be a slutty nympho?"

"CHRIS!!! That's gross! And where did you get that language?"

Shit! I had taken the game too far, just when it was getting
really good, and now it was over. She stormed out of my room in
a huff, while I lay on my bed with my girl-clothes disheveled and
my lipstick smeared... and still incredibly horny! Oh well; if
she wouldn't do it....

I got the brush and the jar of vaseline, pulled down the panties,
and lay back on the bed. "Oh, Andy! Fuck me, lover! Oh, yes!
Shove it in me," I moaned softly as the makeshift dildo reamed my
ass. "Oh, yes... fuck my pussy!" I said, repeating the dialogue
from the porn book.

Just then the door swung open, and there was Andrea, changed back
into her regular clothes with my boy-clothes in her hands.
I stopped thrusting the handle into my rectum, but didn't try to
cover myself.

"You are SUCH a little pervert, Chris," she said. But she
giggled when she said it, and there was a grin on her face. I
could tell she wasn't angry with me. She dropped the clothes on
the floor, closed the door behind her and came over to sit on my
bed. "Go on," she said; "keep doing it." And when I resumed the
fuck-strokes, she reached out and began fondling my penis, making
it instantly hard. "It's bigger than it used to be, Christine,"
she murmured admiringly, as she wrapped her fingers around my
stiff boy-cock and began stroking it up and down. Her other hand
began caressing the soft pouch that held my nearly-adolescent

"Does that feel good, Christine?"

"Oh yes, Andy!" I gasped. "It's REALLY good!" I closed my eyes
and groaned as I rammed my ass more vigorously. I had never
masturbated my cock up-and-down like that, and her stroking hand
was blasting my nervous system into a whole new realm of
sensation. I wondered afterward whether she'd done this to other
boys, in some dimly-lit room at a party. But at the time I was
totally consumed by lust. Being masturbated for the first
time... by my own sister... as the brush handle churned inside my
ass... each thrust making my anal nerves hungry for more. Soon,
the incredible feelings rose to such a peak of stimulation that
my whole body trembled and vibrated, as my first-ever orgasm shot
through me. There was no cum, but the euphoria was all-encompassing.
I stopped fucking myself and told Andrea to stop stroking my cock,
which glowed crimson from her intense jacking.

"Oh, Andy... that was great!"

She grinned, but then said "Chris... you know I love you.... But I
don't think I should do that again.... OK?"

"I understand. I won't ask you. And Andrea... and I love you

I made good on my pledge and kept my sexual fantasies -- and
activities -- to myself. It was strange that I had learned how
to masturbate from my own sister, but I took to it with gusto.
I practiced it often, usually in tandem with anal play, until I
could string together several dry orgasms with just a brief pause
between each. Being on summer holiday, I was spending long
periods of time in the refuge of my bedroom... fantasizing,
dressing up, and masturbating. Andrea, on the other hand, had an
active social life, hanging out with her circle of girl friends.

One of Andrea's best friends was a pretty girl who had moved into
our neighborhood at the beginning of the school year. Her name was
Debbie, and her family had a lot of money. She was allowed to use
makeup whenever she wished, wore the latest clothing styles, and
got a generous allowance that resulted in her having all the
newest records as soon as they came out. One day in late June,
she came by our house and invited Andrea over to listen to her
newest Fleetwood Mac purchase (this was 1977).

"You can come over too, Chris... if you want," she said. I
readily agreed. I'd never been to her house before. Maybe I'd get
to see her 15-year-old brother, Bobby, who was home on summer
vacation from a boarding school up north. I'd only seen him a few
times, from a distance, and he looked incredibly handsome.

When we got over to Debbie's house, nobody was home. We went back
to her bedroom -- which was done in an over-the-top-feminine
decor that I thought at the time was totally wonderful. As we sat
around listening to the music play on her stereo, Debbie said
something that almost made my heart stop.

"Let's try on some of my clothes? We can do make-up too. OK?
You too... Christine." She spoke my secret girl-name with a
teasing voice. "I've heard all about how you like to dress up."
She grinned at me slyly as I felt my face redden with
embarrassment. Then I looked over at Andrea with an accusing
look on my face.

She looked a little guilty, but said "Sorry, Chris, but Debbie
was telling me secrets about her brother, so I HAD to give her
something in return. Right?" For some reason, that seemed like a
reasonable explanation for disclosing my secret fondness for
dressing in girls' clothing. "Don't worry; Debbie promised that
she won't tell anyone. And... like... you DO want to try on
her clothes; right?"

I nodded my head in agreement... embarrassed, but increasingly
excited. Debbie went over to her closet and took out her skimpy
cheerleader outfit and held it out to me. Bright red, trimmed with
white; a picture of a megaphone on the front with the word
"Springfield" (the name of our junior high). All hesitation in
my mind evaporated as I took the outfit from her and held it up
in front of me, looking at myself in the mirror. I smiled shyly
as the girls giggled happily and searched for things to wear from
Debbie's brimming closet. Debbie then handed me a pair of red
panties that matched the dress, and a bra... a padded bra!

I went to the private bathroom that adjoined her bedroom to
undress, hearing the girls still giggling in the other room as
they changed. I was thrilled as I stood nude in front of the big
mirror and slipped on the panties and bra. My penis stiffened
with erotic excitement, and I rubbed it with one hand while the
other hand wandered over the padded B-cup bra. Then I put on the
short pleated skirt and form-fitting top and twirled around a few

As I walked back into the bedroom, Debbie was wearing a very
short and slinky black mini-dress that barely covered her
matching panties and clung to her slender body. It took me a few
seconds to figure it out, but then it hit me.... the reason
Debbie had given me a padded bra was because she was flat-chested
herself! But now she wasn't wearing a bra, and her small budding
nipples just barely pushed out the silky material. She looked
like a fashion model! Andrea was wearing a disco outfit of very
tight, very low-slung, satin bell-bottom pants and a matching
blouse that left a wide swath of skin showing at her flat belly.
They both looked great!

"Let's do our make-up and hair," said Debbie. "Can I do your
eyes, Christine?" My cheeks warmed again at the sound of someone
other than Andrea saying my secret girlish name, but Debbie was
very friendly as she sat me down at her vanity and began applying
garish blue eyeshadow, as well as mascara and eye liner.
I did the rest - lipstick, blush for my cheeks, and fixed my hair
with a curling iron and hair spray.

Each of us tried to achieve a look of sexy sophistication, and I
was overjoyed at how I looked. I could almost pass for a 15 or
16-year-old girl! When I had walked into Debbie's house, I looked
like an androgynous boy with delicate features, but now I was a
stunningly pretty girl cheerleader!

Our conversation turned quickly to boys... looking over issues of
Tiger Beat, Fave, and 16... searching for the hottest pictures of
teen heart-throbs. Debbie and Andrea treated me exactly as if I
was just one of their girl friends, giggling about how sexy
certain celebrities were. And then the conversation turned to
boys at school. Amazingly, I felt comfortable telling Andrea and
Debbie which boys I'd fantasized about during the just-completed
school year. When I mentioned Brian Fisher, an athletic 8th
grader, Debbie giggled mischievously.

"Did Andrea ever tell you about the time she and Brian were
making out on the sofa at Suzy Wilson's party..."

"Debbie!" said Andrea, seeing where this was going.

"... and he had her blouse unbuttoned and her bra undone... and
he had his jeans open and his zipper down..."


Debbie cut short her account, but I was left with a strange
mixture of revulsion and arousal at the image of Andrea having
her hands on the hard cock of an 8th grader (a boy that I had a
crush on!), while he felt up her bare breasts. But the arousal
feelings won out, and I decided to ask her about it next time we
were alone.

We kept talking about boys, and I mentioned that I thought
Debbie's brother Bobby was handsome. Now it was Andrea's turn to
giggle... and get some revenge.

"Well, you can hear all about it from Debbie. She was just
telling me yesterday about how..."

"About how I gave him a hand-job," said Debbie with a laugh, not
at all embarrassed to take up the story. "He acts like more of a
pervert each time he comes home from that stupid boarding school
on holiday. He's always asking if he can feel me up. And he
leaves his door part-open so I can see him jacking off on his
bed. And he started pestering me to give him a blow-job! As if!
He kept at it so much that I told him I'd give him a hand-job
just to shut him up.... Well, and also because I wanted to check
out that big cock of his up close," she said with a giggle. Then
she added "anyway, it's not like it was the first time I felt a
boy's boner."

"Wow!" was all I could say.

"Ya know, Christine," she said; "I might even give you a hand-job
if you do a little strip-tease for us. It's so freaky that you're
like a girl with a dick. Take down your panties and let me give
you a feel."

I didn't like the way this was going. Yeah; I knew I was a bit
"freaky", but it hurt to have someone else point it out. And then
came the kicker from Debbie.

"Maybe I'll even fuck you in the ass with a hair-brush. I just
KNOW you like that!"

I felt like I'd been punched in the gut. I was almost nauseous
that Debbie knew my most embarrassing secret. I should have
unloaded on Andrea for her betrayal, but instead I just ran to
the bathroom, crying, and changed back into a boy as quickly as I
could, wiping off the make-up as tears flowed down my cheeks.

"Chris! I'm sorry!" came a voice through the door. It was Andrea;
not Debbie.

I left without a word, humiliated, running home and locking
myself in my room, and crying into my pillow. But when I'd
settled down, my thoughts returned to Debbie's room. Incredibly,
I started thinking about how sexy it would have been to have
Debbie fucking me in the ass while she stroked my cock. What had
been mortifying in reality was incredibly arousing as a fantasy!
Before long, I had the hair-brush out and lubed it up....

A few days later, I was riding my bike down to the shopping
center to buy some candy, and as I rode past Debbie's house,
there was her brother Bobby in the front. He was tossing a
basketball into a net that was mounted beside the driveway,
wearing only a pair of short tight athletic shorts (they were
nothing at all like the baggy basketball shorts boys wear
today!). A sheen of sweat emphasized muscles on his chest and abs
that had to have been acquired by hard work in a gym. I slowed my
bike almost to a stop, watching him shoot jump shots and do fancy
dribbling. Then he looked over at me and called out.

"You're Chris, right? Andrea's brother? Come on over and shoot
some baskets with me."

I didn't know what to say. Me? Hang out with him? But I rode my
bike into the driveway and got off. He bounced me the ball, and I
made a weak shot at the goal that missed by a lot. He jumped for
the rebound and swished a shot through the net... shooting while
still in mid-jump. Then he got the ball and tossed it to me

"I'm kind of a spaz, Bobby. Can I just watch you shoot?"

"Sure, kid. That's fine," he said, and proceeded to put on a show
that demonstrated his natural athleticism. Much as I was
impressed with his basketball skill, I was far more interested in
his body. He was mature-looking for a 15-year-old. Maybe 5'10";
lean and broad-shouldered, with tufts of hair beneath his armpits.

"Want to come inside and have a coke? We can get to know each
other. OK?" he said after a few minutes.

"Sure!" I replied, flattered by his attention, then added "uh...
is Debbie here?" I didn't want to deal with her right now.

"Nah; she and my mom went into the city to buy clothes. As if
Little Miss Fashion Model needed more clothes, huh?" he said with
a grin. "They won't be back for a few hours."

As we entered the kitchen, he told me to sit at the table. I
still couldn't keep my eyes off Bobby body's as he moved around
the kitchen, getting Cokes and filling glasses with ice. His
pants were so short and so tight that they outlined the bulge in
front. I remembered how Debbie had commented on the size of his
cock, and I was hypnotized... fantasizing what he'd look like
nude. When I finally pulled my eyes away from his crotch, Bobby
was grinning at me.

"You like what you see, huh?" he asked in a sly tone as his hand
slowly rubbed the front of his shorts.

"I... I... I...." No words were forming in my brain. I was
totally flustered as Bobby walked over to me an handed me a

"Don't worry. I don't mind." Even after giving me the Coke, he
continued to stand right next to were I sat, looking down at me.
I was looking at his hairless, muscled chest, afraid to meet his
eyes. He was so close I could smell the musky sweat that
glistened on his smooth torso, and it inflamed my arousal.
To my utter amazement, Bobby slowly peeled down his shorts to
mid-thigh, revealing a jock-strap that bulged with its stiffening
contents. "Take out my cock. Feel it. I know you want to.
You've had your eyes on my crotch, so might as well get your
hands on it. Go on; check it out."

I was mesmerized. My hand trembled slightly as it pulled aside the
cotton pouch. Bobby's cock sprang out... half-hard, and
incredibly masculine, with a thick patch of dark hair at its
base. As my fingers wrapped around it, I felt its heat... felt it
throbbing in my hand. It instantly stiffened all the way,
standing up 7 inches, medium-thick, glowing dark red and pulsing
with engorgement. I don't know what got over me, but I had a
burning desire to suck his it.

From where I sat, I barely had to lean forward to kiss Bobby's
beautiful cock-head. My wet lips spread around the circumcised
glans... and then I just kept taking more of the shaft into my
mouth... almost as if I couldn't stop myself. When I had taken a
little over half of Bobby's cock, my throat gagged and I had to
back off a bit. But I moved my lips back down, hungry to take
this incredibly beautiful adolescent boner all the way to its
base (just like the girls did in my porn novel). It was like a
religious experience, and I was worshiping this perfect cock.

"Whoa! Ease up," said Bobby as he pulled my head away from his
crotch, stuffed his erection inside the jock, and hiked up his
pants. "Man! You're even more eager than I thought you'd be."
Then he looked at me with a devilish gleam in his eye and said
"Debbie told me how much of a sissy-boy you are... Christine."

My heart stopped, and I could feel my face becoming instantly
flushed. He knows! He even knew my secret girl-name.

"I... That is... I don't..." I mumbled, lamely. I sat there
feeling sacred and stupid, wishing I could dig a hole and climb

But Bobby just reached out his hand and ran his fingers tenderly
through my long hair. I felt light-headed at his touch.

"You have nice hair," he said, in a voice that was both soothing
and sexy. "I can tell you'd be a beautiful girl." I was
speechless. And then he said "I have a few kinks myself. It's
pretty well unavoidable at a place like the Athens Preparatory
School for Boys." He said the name of his boarding school in a
slightly sarcastic tone of voice. He stroked my hair again, this
time leaving his fingers entwined in the strands and tilting my
head up to meet his eyes. "There's a kid at my school who's a lot
like you. Same grade as you, and almost as pretty. His name is
Vernon, but he likes to be called Veronica when he's doing his
girl thing. He likes to have fun with horny upperclassmen like
me, and he always has a lot of takers since there aren't any
girls around. There's a little game we play... he pretends to be
my girlfriend, and I treat him just like he was a chick. Works
out really well for both of us." He paused, his eyes burning into
my soul, and then continued in that honey-toned baritone voice.
"Think you might be interested in playing that kind of game? I
know exactly what a sissy-boy like you wants."

I nodded my head timidly, not saying a word, but knowing with all
my heart that I desparately longed to "play that game".

"You done much sex stuff with other guys?" he asked. I shook my
head from side to side, still not uttering a word. "You done ANY
sex stuff with a guy?" Again I answered with a head shake.
"A virgin, huh?" he said in a surprised tone.

"But I want to play the game," I murmured, feeling my face
blushing with embarrassed excitement. "I'd really like to be
your girlfriend." The words were difficult for me to get out,
but I'm so glad I said them.

"You're on, girl! I'll take it slow and teach you how to take
care of a man's needs. This'll be great!"

Then he pulled me up from the chair to stand facing him. While
looking into my eyes with sultry gaze, he reached out and
unfasten my pants. "Pull them down, Christine," he murmured.
"Let me see what you've got."

I pulled down my shorts and briefs in one motion, lifting the
bottom of my tee shirt up to proudly show off my rigid 4-inch
penis. I looked up at him with a hopeful smile. He reached down
and his fingers fondled my ball-sack briefly and then stroked my
erection. "I like a hairless cock on a sissy-boy," he said.
"Veronica has some pubes, but she shaves it. Do you shoot cum
yet?" I shook my head from side to side, hoping he wouldn't be

"Perfect!" he said, as his fingers stroked up and down on my little
cock-shaft and he played with my dangling balls with his other
hand. "Let's go up to Debbie's room and find something
appropriate for you to wear. Mom and Deb will be out shopping
for at least 3 more hours. We can play around for a good long
time in my bedroom. Follow me."

I fastened my pants and followed him down the hall and into
Debbie's room. He entered her walk-in closet and started
rummaging around. I stayed outside, again admiring Debbie's
frilly decor and the vanity table laden with various kinds of
make-up. Bobby finally emerged holding a black baby-doll nightgown
that looked like it wouldn't even cover my butt. And the
material was so silky that it was practically see-through. Then
he went to her dresser and pulled out a pair of black silk
panties -- the skimpiest bikini panties I had ever seen!

"What do you think, Christine?" he asked. I just smiled and
reached for the sexy garments. "You put them on while I take a
shower. Put on some make-up too if you like... and if you're good
at it. Make yourself beautiful for me... OK?"

And then he did something that blew me away. He drew me to him
and planted a gentle kiss on my lips. As I pressed back, he
opened his mouth and let his tongue flick out. For a few long
moments, our tongues were entwined in a wet, sexy, hungry,
wrestling match.

He broke the kiss and said "come to my room when you're ready.
It's right across the hall." And then he left, as I stood there
panting for breath, with my cock standing up rigid in my pants.

As I changed into the nightie, my excitement level rose and my
heart thudded in my chest. It was smoother than any material I'd
ever felt and so sheer that I could see my nipples as I looked in
the mirror. The panties barely contained my little boner, and
only a small portion of my ass was covered in back. I wished
I had breasts to complete the image of total femininity, but
wearing a padded bra under a sheer nightie would be all wrong.

As I listened to the shower running in the room directly across
the hall, I quickly but carefully put on some make-up from the
considerable array on Debbie's vanity. I even put some blush on
my nipples to make them look sexier. Then I curled my hair a
bit, as I had done the last time. Hearing the shower turn off, I
quickly finished up, dabbed my neck with a little perfume, and
made my way across the hall, nervous but brimming with

Bobby had a typical boy's room, with a variety of posters on the
walls: cars, sports and rock music stars... and that one of Farrah
Fawcett where she's wearing a red bathing suit and has the
fantastic hair. He walked out of his private bathroom wearing a
blue terrycloth robe that came down to mid-thigh. He was drying
his hair with a towel, and it arranged itself in natural loose

"Christine... you look beautiful," he said, sounding totally
sincere as he took hold of my trembling hands in his and kissed
me gently. He made me feel so warm inside... like I was melting
into a puddle. I knew that I would do anything he asked.

"Still a little nervous, huh?" he said. I nodded. "Do you like to
dance? Go over and pick out a record and put it on the stereo."

I glanced through his albums and choose the soundtrack of
"Saturday Night Fever". I'd heard some of the cuts on the radio,
but not the record. As I dropped the needle on the disc, the
sound of the Bee Gees singing "Stayin' Alive" filled the room
with throbbing disco music. I had practiced dance moves in my
room for years, copying what I saw on TV and in the movies, and I
knew I was good. I began to dance, loose and feminine.

"Nice!" murmured Bobby as his eyes scanned my scantily-clad body,
gyrating in the middle of his bedroom. He started dancing too,
in a more rigid style, like most teenage white boys did. But
then he put his arm around my waist and took my hand, and we
began doing a simple version of "the hustle" -- the dance that
was the rage in the discos. (I'd seen it on TV and practiced it
with Andrea.)

I was starting to feel totally at-ease with Bobby. He was
supremely self-confident... so charming... so handsome. And when
the music changed to a slow song titled "How Deep Is Your Love",
he took me in his arms and pressed his body against mine. His
arms were around my waist, and mine around his neck, as we began
slow-dancing. His hands slipped down to my ass, which were only
half-covered by the nightie. Then his hands slipped inside the
tiny panties, and caressed the slender globes of my butt
cheeks... squeezing, stroking, pulling them apart... bringing his
fingers to my puckered hole and stimulating the exquisitely
sensitive nerves at its entrance. A moan escaped my lips, and I
closed my eyes to savor the sensations.

Bobby gently kissed my neck, and I heard him inhale deeply. I
think he appreciated the perfume I had applied there. His hands
were now inside the nightie we slow-danced, roaming up and
down the smooth skin of my back and shoulders. Then he whispered
in my ear.

"Open up my robe, Christine, so you can feel how hard you're
making me."

I reached down and undid the sash at the waist of his bathrobe
and pulled the robe apart, returning my arms to his neck as I
snuggled against his warm bare skin. He shrugged the robe off his
shoulders and let it fall to the floor. Now he was completely
naked. His big cock was fully stiff, pressing against my belly
as we danced. We kissed. Deeply, hungrily... tasting each
other's tongues.

Without breaking the kiss, Bobby reached around and picked me up,
lifting me with ease... with one strong arm around my upper back,
the other holding up my bare legs.

"Let's make love, Christine. You're such a beautiful girl!"

Oh, God! His words made me dizzy with sexual desire. He was so
right when he had said that he knew just what a sissy-boy wanted.
I longed to be treated just like a desirable teenage girl, and he
was doing it so perfectly.

"Yes!" I breathed. "Yes Bobby; take me."

He laid me down on my back on his double bed, on a soft and
fluffy comforter. I stretched out, trying to look sexy... like
a picture of Marilyn Monroe I'd seen. Sitting down beside me,
Bobby leaned down and kissed my mouth as his hand played with my
smooth chest, pinching my nipples and making them stiff. He
pushed the nightie up around my shoulders and began sucking at
my tiny rouged nipples, as his hand slid down to caress my inner

"Your breasts are beautiful, Christine," he murmured, as his
tongue flicked at my titties. He was just playing to my sissy
fantasies, but I absolutely loved to hear it!

Bobby's mouth continued lower, kissing my flat belly as he
maneuvered himself between my spread legs. He nuzzled my crotch,
and I could feel his hot breath through the silk panties. Then
his fingers took hold of the waistband of the panties and pulled
them down, exposing my desperately stiff little boner.

I held up my legs, and his hands quickly pulled the panties all
the way off. I lay there with the nightie bunched up, totally
aroused, and panting for Bobby to make love to me. Would he fuck
me right away? I knew I was ready for it. Probably more ready
to be fucked than any other 13-year-old virgin boy had ever been.
But Bobby was going to show me a good time before he took me for
his pleasure.

"Oh, Bobby!" I gasped, as his lips slid onto my plump little
erection. "Oh, YES!"

His hot mouth plunged down the length of my hard cock, and his
tongue slathered all along the 4-inch shaft. On the upward
stroke, he applied slow, delicious pressure to the shaft before
sliding down again. Up and down his mouth went, like a wonderful
machine, pressing against the hairless skin at the base of my
erection, then rising to flick the glans and the piss-slit with
his tongue. I grabbed the bed-covers, my whole body alive with
electric chills like I'd never before experienced. When he made
my cock-head graze back and forth along the bumpy roof of his
mouth, it was so intense I practically jumped out of my skin.

All too soon, he pulled his mouth off. But when he started
sucking my balls, it was almost as good. I lifted my legs back
and apart to give Bobby more space to work, and when I did, his
mouth shifted once again... farther down, planting itself firmly
on my puckered pink hole.

The handsome teenager spread my ass-cheeks apart with his hands
and licked all around the rosebud. I squealed like a little girl
on a roller coaster as his tongue pushed into the circle of
muscle... into this most erogenous part of my body.

"Yes! Oh yes, Bobby! Lick my pussy! Oh, YES!" It was just like
I had read in the porn novel! I flexed the hole open and felt
his tongue burrow into me. And when his tongue came away, it was
quickly replaced by a finger... carefully entering me to the
knuckle... then all the way to the hilt... then moving slowly in
and out. He began finger-fucking my secret place, and I pushed
my bottom up, wanting more, wanting it harder... faster...

As his finger plunged and twisted inside my hole, his lips
returned to my cock, his head bobbing up and down, saliva running
down the pink shaft that swelled and twitched in his hot mouth.
I could feel it happening... the ecstatic pleasure... the
incredible buildup of pressure. The dam was about to burst. I
could barely stand it, growing more and more intense as Bobby
continued to suck.

I was babbling incoherent pleasure noises in my high-pitched
sissy-voice as the electric sensation of orgasm rushed through my
body. Bobby continued to move his mouth on my cock and my
immature penis stayed fully erect. The pleasure continued on an
unbelievably intense plateau, and I'm sure he could have brought
me to a string of multiple dry climaxes if he'd kept going. I
wanted to orgasm again and again with my cock in his talented
mouth and his finger in my asshole. But at last he rose up,
kneeling between my legs and smiling down on me as I panted for
breath, a helpless slave to my lust and to his masterful will.

"I can't wait to make love to you, Christine," he said in his
rich, sexy voice. "But first you need to get my cock ready
with your mouth."

As he moved up and straddled my chest, I grasped his manly cock
in my hand and guided it to my lips. Bobby put another pillow
beneath my head and held onto the rail at the top of the head
board. As I began to suck him, I knew instinctively what to do.
I also knew that I was doing it well.

"Yeah, baby! That's it! Give your man's cock a good suck. Get
it ready to fuck your beautiful pussy." His tone was soothing,
but the words dripped with wanton lust.

I gave myself over completely to serving Bobby's cock, devoting
all my concentration to this sacred act about which I had
fantasized for so long. He was motionless as I worshiped his
cock-head with my lips and tongue and slowly began taking
his erection deeper into my mouth. I put my hands on his ass
cheeks and pulled him toward me, making his cock sink deeper.
When it reached the entrance of my throat I paused for a moment,
took a deep breath, then craned my neck and pushed my mouth
farther onto the shaft.

Bobby's cock was considerably bigger than those hot dogs I had
practiced with, but I was determined to do it. Bit by bit, I took
it deeper... past the entrance, then squeezing into my tight
throat. Bobby groaned with pleasure, and his hips began
moving... slowly at first... drawing back a little, then forward.
When he was in to the hilt, as deep as he could go, I felt an
incredible rush... I did it! I swallowed his cock all the way
into my throat! Not only did I not mind it... I ADORED it! He
began slowly face-fucking me in long strokes, and I was loving
it. Bobby was looking down excitedly at his cock disappearing
between my lips, and I was looking up at his handsome face. I
couldn't speak, of course, but my mind was saying 'I love you,
Bobby. I love you!'

"You're incredible Christine! God, that was good!" said the
muscular teenager when his cock finally popped out of my mouth,
glistening with saliva, dark red and pulsing with arousal. "Are
you ready for me to fuck you?"

"Yes," I whispered. "Oh, Bobby... YES!"

"Turn over, baby" he instructed; "face-down, and put a pillow
under your hips." He reached over to the bedside table and got a
small plastic bottle of liquid, squeezed some onto his palm, and
stroked it onto his cock. Then his slippery fingers eased
between my ass cheeks again, and I raised up my butt to him. Two
lubed digits entered my hole and I flexed open to accept them as
they twisted into my rectum. I had sometimes put all four of my
own slender fingers in there before, so I could easily
accommodate his two.

"Damn, girl! I don't even need to get you ready for it!" he said
as his two fingers slid back and forth inside me.

"Do it now, Bobby! Fuck me, honey," I purred in the most sensuous
voice I could generate. How many times had I fantasized about
this moment? How may times had I shoved that brush-handle into
my ass, imagining it was an older boy's hot cock? And now it was
going to happen for real!

As I craned my neck to look back at him, Bobby knelt behind me,
took his stiff cock in his hand, bent it forward, and rubbed it
back and forth across my anal pucker. I reached back and pulled
my ass cheeks apart. My pussy flexed open, rhythmically, like
a little mouth hungry for food. When he pushed forward slowly, I
felt a pang of discomfort as the head of his cock pushed through
the passage. I suppressed a gasp, and he just kept on pushing
into me. He began moving his cock in and out, slowly and just an
inch or so at a time at first... gradually building up to long
thrusts to the hilt. I felt wonderful sensations of delicious
fullness and warm erotic pleasure.

"Oh, yes! Oh, Bobby! Give it to me!" I whimpered. He was in total
possession of my body, and it was utterly fantastic... my sexiest
dreams becoming reality.

"You're my little slut, aren't you baby? Your ass is mine,
Christine, and I'm gonna give you a fuck to remember."

Then he slapped my right ass cheek... once, twice, three times.

"Oh yes! Spank me Bobby!" I moaned. Even though the slaps stung,
they served only to increase my lust and my joy at submitting to
this handsome teenager. He gave me three more hard slaps to my
left butt cheek. Yes, he was right; I was his willing little
slut... his sissy-boy whore. At this point, I wanted nothing
more than to have his big hot cock plowing back and forth inside
my ass... stimulating my most sensitive pleasure nerves.

With each long stroke of his cock, I raised up my butt to receive
his thrust. And each time his hips drove into my ass, my rigid,
throbbing erection slid across the pillow under me. The friction
of my sensitive cock-head against the soft cotton pillowcase
merged with the anal pleasure I was feeling, creating an ever
building peak of sexual ecstacy. Faster and faster he slammed his
slippery cock deep into my body. His guttural vocalizations
signaled his approaching orgasm, and his sweat dripped onto my
back. My own orgasm was very near too, taking me to a place that
was even more wonderful than when he had sucked me.

"Uh... Uh... Harder, darling... Yes; faster... Oh, yes; fuck me!"
I pleaded in my high pitched sissy voice. My body was trembling
all over as the wave of orgasm reached its highest peak and then
crashed down with a thundering impact. My anal muscles spasmed
in time with the vibrations in my little boner, and Bobby grunted
as he gave me a half-dozen rapid, urgent thrusts that preceded
the blast of hot cum into my pussy. I could feel his cock
throbbing inside me, shooting its nectar into my love-hole.

Bobby collapsed onto my back, his cock still deep inside me,
still trembling with the aftermath of his powerful orgasm. I
squeezed my ass muscles around it, giving him a cock-massage,
milking out every bit of his cum. He wrapped his strong arms
around my torso and kissed the back of my neck.

"Damn, Christine! Between you, and Veronica back at school, I
gotta admit that sissy-boys make better lovers than chicks," he
murmured in my ear. "That was awesome, baby!"

Then his softening cock slid out of me with a "pop". He turned
me over on my back and took me in his arms. For a long,
leisurely time, I drifted on a cloud of happiness as he hugged me
to his strong body, caressed my skin with his fingers, and kissed
me gently and slow. As the merger of our lips and tongues became
ever more aggressive and urgent, I felt my erotic energies
recharging. When he began fondling my dick, it stiffened
instantly. And his cock was also rising to erection as it humped
against my thigh.

"Do you want to fuck me again Bobby?" I offered, in a hopeful

Bobby looked over at the bedside clock. "We still have plenty of
time to play. How about something different.... You go back
to Debbie's room and get dressed up like a total slut. Use more
make-up too... you're good at that. I'll wash up a bit, and you
can give me a nice blow-job. How's that sound?"

"Yes, Bobby. I'll do anything that you want," I replied, with
total honesty.

I hopped up from the bed and pranced across the hall, wearing
only the ultra-short nightgown. My stiff erection swayed back and
forth as I ran in mincing steps. Going through Debbie's things,
I was once again struck by how much clothing she owned... and how
jealous I was! Bobby wanted me to be a "total slut", so I
picked out a black leather mini-skirt, knee-high boots, a padded
bra, and a fuzzy pink short-sleeve angora sweater. The sweater
left a swath of my tummy uncovered, exposing my belly-button. I
decided not to wear any panties. Looking at myself in the
mirror, I saw a stereotypical young teenage girl prostitute.
I was certain it would please Bobby!

At Debbie's make-up table, I put on excessive amounts of blush,
eye liner, mascara, and eye shadow. I picked a garish shade of
lipstick that emphasized the full ripeness of my lips. Perfect!

"Yeah, baby! You know exactly how to please me, alright!" It
was Bobby, standing in the doorway of the bedroom, wearing tight
flared slacks and a black satin shirt, unbuttoned to mid-torso.
He looked like he was ready for a night at the disco, and
I jumped up to serve him. I struck a pose with one hand behind
my head and the other on my hip. I tried to look as sexy and
naughty as I could. Then I raised up the hem of the mini-skirt
and exposed my stiff penis and balls.

"That's it, bitch; show me what you've got!" I vamped some more
for him, as he undid the top button of his pants. "Come over
here and get down on your knees; give me a suck," he ordered.

I knelt before him and lowered his zipper. He wasn't wearing
underpants, and his half-hard cock sprang out, right in front of
my face. His hand came down and lifted my chin up, making me look
into his handsome, smouldering eyes.

"Blow me, you pretty little sissy-whore. Suck it good!"

My lips captured the head, and I lavished attention on it with my
tongue, making his erection pump fully hard. As Bobby's fingers
slid through my long hair, my mouth descended the rigid pole of
masculine flesh, deeper and deeper.

Yes! I had found the purpose of my life. This was were I wanted
to be... servicing a handsome stud with my mouth, or submitting
to a vigorous fucking. As his cock-head lodged deep in my
throat, my hand went to my straining boyish erection and began to
stroke. Oh, yes! This was heaven!


That entire summer, I had many other opportunities to explore the
world of sex with Bobby. Sometimes I could dress up when we had
his house or mine to ourselves. Other times we went deep into
the woods that adjoined our neighborhood, and we had boy-on-boy
sex in every way he suggested.

At Bobby's urging, I asked my parents if I could apply
to his boarding school. I had always had excellent grades, and
my parents were well-off financially. Mom wasn't sure if I
should go, but she knew how unhappy I'd been at public school.
And I overheard Dad telling her "maybe an all-boys school will
make him more of a man." They finally said OK, and my
application to the school in Athens, New York) was accepted.

But rather than "making a man of me", I blossomed as a sissy. I
was in a friendly competition with Vernon/Veronica for the title
of reigning Queen of Athens Prep. Veronica and I eventually
became roommates and shared each other's stash of girl clothes
(as well as sharing each others beds). And we always had our
pick of horny upperclassmen who had no compunction about using a
sissy-boy for sex since no real girls were around.

If you like, maybe I'll tell you about some of my adventures as a
nympho sissy-slut at an all-boys boarding school.

The End

Write to me at

All my stories are available on Nifty Archive (
Go to Nifty's "prolific net author" page and look under "Bill"

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Nifty - Transgender - Teen - Sissy Boys Story