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Nifty - Transgender - Highschool - Balled At My Sissyboy Debut

Date: Fri, 16 Sep 2011 10:52:02 -0700 (PDT)
From: Jack Herold <>
Subject: Balled At My Sissboy Debut

Balled At My Sissyboy Debut

by Hartford

I turned eighteen in March during my senior year in high school, on the day
I became a dick girl, or a sissyboy, whatever the difference is. My
transformation began a little after seven on my birthday evening. I was at
the computer when Mother pushed open the door to my room. She had a large
box that she plunked on my bed.

"What's this?"

"More presents. These are special ones for your secret desire."

My heart jumped to my throat. I had only one secret desire, and in fact had
been indulging it when Mother's footsteps sounded in the hall. The computer
screen now displayed something quite unlike the pictures from "Sissyboy
3-D" I had been viewing seconds before. Mother nodded at the computer and
smiled as though she knew.

"What do you mean?," I said, keeping my voice as calm as I could.

"I mean your desire to suck penises and have them fuck you, dear. You can't
fool your mother. And there's no reason you should. I want you to be
happy, and if being a queer is what you want, well then it's what I want. I
mean there's nothing wrong with it. They even let queers be in the
government now. They even let them get married to each other, for goodness

I stopped myself from asking why she thought I was a "queer". What
difference did it make? Probably she had tracked my Internet footsteps
somehow. Maybe she had found out about my crossdressing in my sister's
clothes at the mall, which I had done twice. I was embarrassed, as you
would expect, but Mother's apparent sweet acceptance of her son's
"queerness" didn't really surprise me. You have to know Mother to

I felt that I needed to clarify one thing. "Mother, I'm not interested in
queers. I'm not interested in guys who are gay."

"I know that, dear. You like real boys, or I suppose it's real men, not
boys. I know. And why shouldn't you? You are pretty as can be. It's my
fault you weren't a girl to begin with."

"It's not your fault."

"Well, we are what we are. You have all the makings of a lovely
girl. Except one."

"Except three."

"Oh, don't worry about those. Open your presents."

The box was open at the top. I turned it over and spilled the contents on
the bed. There were sexy panties and bras, two teddies, two skirts, cute
tops, makeup and creams, two wigs - blonde and auburn, a pair of realistic
tits, two realistic dildos, in all a dick girl's treasure chest. Twenty
minutes later, I was ready to meet the world in my new self or at least the
visitor waiting for me in the living room.

"You look just dreamy, dear. Bob Bard will be thrilled when he sees you."

I blinked at her. "Mr. Bard?"

"He's downstairs. He knows all about our little secret. He's very excited
to meet Debbie. Is that name all right? You need another name. Bob loves
the name, Debbie. He suggested it."

I was having trouble processing this. "You told Mr. Bard!?"

"I did. You may not have noticed but when Bob is around he can hardly keep
his eyes off you. Imagine how it will be when you're a girl! Bob says you
have the perfect face and body for a sissyboy, which is the same thing as a
dickgirl, I gather."

"It's not exactly the same," I mumbled. My heart was racing.

"Is it close enough?"

"I guess so."

"That's good because I think Bob thinks it is."

"He's downstairs?"

"Yes. Waiting for you."

The other question, shouting in my brain, I was afraid to ask and Mother
didn't elaborate.The Bards were our next door neighbors. They had two boys
younger than me, big kids like their father; linemen on the high school
football team, and a little girl. Mrs. Bard was a teacher at the high
school. I actually had fantasized about Mr. Bard, and I had read his stares
differently from Mother, as looks of disparagement. I preferred her

"Is Mr. Bard gay?," I finally said.

"No. He's like you, dear, except the opposite. He likes sissyboys or dick
girls, whatever you want to call them. I don't think that's necessarily
gay, is it?"

Mother took my hand and led me from the room. I made her stop at the
bathroom for a last look in the mirror because I worried about my
lipstick. It was fine. I was fine. I looked like a teenage sex model, of
the female variety that is, if you overlooked my chest. Mother said she
thought Mr. Bard would prefer my own smooth chest and perky nipples to
fake boobs, not that my chest was there to see behind the pink cotton
top. The top was buttoned and dipped just below the bottoms of my
panties. My legs were bare and I was barefoot. Mother had selected the
blonde wig and it framed my made-up face quite nicely, yellow curls falling
to my shoulders. I had an idea of my own then, remembering a description of
a sissyboy from a story, and as I looked in the mirror I opened the buttons
and pulled the top over my shoulders and down far enough to partially
immobilize my arms but Now Mr. Bard would see my perky nipples. I was faint
with excitement.

Every light was on in the living room. Mr. Bard was on the sofa, wearing a
bathrobe. He looked at me. I waited for him to smile or say something. He
just looked and blinked a few times.

"Hi, Mr. Bard," I said.

Mr. Bard still didn't smile but he said, "Hello, Debbie. You are the
perfect sweet piece of ass I thought you would be."

"Thank you," I mumbled, and glanced around to see Mother's reaction to
Mr. Bard's greeting. She looked pleased as punch.

There was another long silence while Mr. Bard continued his staring until I
stupidly said in my nervousness, You're wearing a bathrobe."

Mr. Bard's face relaxed and he laughed. "I am indeed, cutie pie. Turn
around. Pose for me. Lift up that thing you're wearing so I can see your

I blushed and smiled at him, feeling naughty. "Gee, I thought my nipples
could be treats, Mr. Bard."

"Oh, God," he moaned.

I was feeling better, less anxious, incredibly excited and somehow
empowered that this hunk of a man who I had thought didn't like me in fact
was turned on by me. I turned around as directed and saw Mother. I was
taken aback, having forgotten her presence in my excitement. What had she
thought of my nipples remark? Nothing critical, apparently. She beamed, and
she had acquired our video camera. Seeing me notice it, she said,

"We have pictures of the first time you walked and your first day at
school. We should have some of your first time as a sissyboy."

This sparked a question I had been reluctant to ask."What does first time
as a sissyboy mean exactly?" I froze as Mother raised her face to the
ceiling, which she often does when she's about to say something big.

"Well, for one thing it wouldn't be right if poor Mr. Bard didn't have his
aching manhood relieved by the dear thing who is making it ache so."

And if I hoped a blowjob was going to suffice, Mr. Bard coughed and added,
"Nor would it be right, Maggie, if a sissyboy didn't get fucked on his

Mother tittered. "Oh, very true, Arnold. Very true."

With that, Mother suggested that I begin posing, which I did. Considering
the dazed state of my brain it was a wonder I could even stand up. However,
posing like a sex model was something I had practiced a hundred times or
more in the privacy of my fantasy life. I was able to do it by rote,
practically. The poses were well received. Mr. Bard's favorite, at least
the only one he asked twice for me to repeat, was getting on my hands on
knees and wiggling my bottom at him with the shift up out of the way while
I looked over my shoulder at him and licked my lips. It was my favorite,
too. And the third time I did it, I said, "Mmmm, Mr. Bard, I hope you won't
fuck me too, too much." I was pretty hot by then. I had also accepted
Mother's partnership, so to speak, in this sissboy venture. I even looked
for her approval of the sufficiency of my naughtiness,though Mr. Bard's
approval mattered more. When he yanked open his robe, I saw I had it. Big

The robe parted right after I made that third little tease.

"I'll decide what's too much or not enough, you sweet bitch," Mr. Bard
said, showing me what I was going to be fucked with. It was mesmerizing,
plus breath taking, plus dicky hardening and I was hard already.

Mr. Bard grinned. "Fearsome, isn't it?"

I was speechless. Mother said, "Debbie's a brave boy."

I might not have been able to talk but my mouth wasn't helpless. I moved on
my knees. Mr. Bard opened his legs for me. Now I looked down on the cock
looking up, straight up it was, like a missile on a launching pad. Fearsome
was a good word for it. The cock bristled with purpose. The pink head
smoothly invited me. Beneath waited the vein bulging shaft, more than my
mouth could possibly take, more I realized that any of me could take. But a
sissyboy must always do his best. I dipped my head and thus began my first
sissyboy assignment, also my first experience of any kind with a cock not
my own. I'll rephrase that: a dick that wasn't my own; silly to call my not
quite five-incher a cock.

After a few kisses and licks, I opened wide and began to suck. Mmmmm, it
was soooo good. What I had been missing! And would be missing still if it
weren't for having such a thoughtful mother. I was a natural
cocksucker. Mr. Bard told me so afterward. In no time, my head was bobbing
like a pro. I felt Mr. Bard's hands hold back my curls so he could
watch. Who could blame him? For me, along with the thrill and the knowing
came a dread. My fate was sealed. I had been made with the looks and by
inclination to be a cock slut and now I was. Thank you, Mother. At least, I
would be a slut for straights, I figured. This struck me as better, as well
as more exciting, than being an outright "queer".

These thoughts were in the back of my mind as my head went up and down. I
was gradually taking in more and more of my slipperly, thick prize. On the
down strokes it filled my mouth and pushed into my throat, gagging me, and
I let it gag me, I wanted it to gag me, I liked it gagging me. I came up
for air so I could go down on it again, sucking at the head, sucking the
shaft, sucking the pulsing hardness, sucking and sucking, then making it
gag me. It startled me when Mr. Bard let go of my curls and grasped my head
to pull me off. I gazed up him, bleary eyed, wondering what was
wrong. Nothing was wrong. He was gasping and struggling to hold back his
orgasm which he did hold back, in order to fuck me.

He reached for me and turned me over. Mother had thoughtfully put two
pillows on the floor. Mr Bard lay me on top of them so that my bottom was
raised. I held my breath. I felt Mr. Bard's strong hands on my hips. Then I
felt what I was waiting for. The cock divided the crease in my bottom and
bumped up against my boycunt where it paused. I stopped seeing as well
breathing, squeezing my eyes shut; squeezing my hands together. Mr. Bard's
cock was rigid and so was I, from head to toe. The pausing ended. The cock
jammed inside me, not far but far enough to make me yell from searing
pain. It was a delicious pain. I didn't mind if it would kill me. I imagine
only a sissyboy can understand that. The cock went deeper and the pain went
deeper, and in a little while the pain began to fade and the pleasure grew
and I became lost then and for good.

Mr. Bard fucked me gently at first, until I got used to it, and after that
he fucked me hard. Not long, though. He was too worked up to make it last
which was kind of too bad but a sissyboy can't complain. I got to like
being a sissyboy from being with Mr. Bard, as compared to a dickgirl, I
mean. Before Mr. Bard left he asked if he could "see" me again. He asked
Mother. She said, "Sure. When would you like him?" Mr. Bard said he would
like me the next day but he would have to pace himself, being married and
all, plus not being a young guy anymore.

"Well,just call me when you want him again, Arnold," Mother told him. They
were talking about Mr. Bard fucking me again and I wasn't even part of the
discussion. It gave me a hardon.

(Editors note: This story is a variation on the theme used in 'The
Adventures of Julie", part one, which I posted about a year ago.)

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Nifty - Transgender - Highschool - Balled At My Sissyboy Debut