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K R I S T E N' S C O L L E C T I O N
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A Sissy-Boy's Story
by Bill (bil47_new@yahoo.com)
***
An effeminate, cross-dressing 13-year-old boy finds all
his sexual fantasies fulfilled when he is seduced by a
handsome and masculine 15-year-old neighbor. (mm-teens,
youths, tg, cd, inc)
***
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 sissy-slut.
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 "Christine".
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 friend.)
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. 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 satisfied.
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 balls.
"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 too."
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 times.
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!!!"
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 again.
"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 glass.
"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 almost 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 in.
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 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 disappointed.
"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 excitement.
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 curls.
"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 thighs.
"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 virgin 13-year-old 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... deeper.
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 butt 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 voice.
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 bil47_new@yahoo.com
All my stories are available on Nifty Archive
(www.nifty.org)
Go to Nifty's "prolific net author" page and look under
"Bill". This story has been posted on Nifty, but isn't
on my list in the author index, because "trans" stories
are segregated (for some reason).
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.
~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 62