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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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WARNING!
This text file contains sexually explicit
material. If you do not wish to read this
type of literature, or you are under age,
PLEASE DELETE THIS FILE NOW!!!!
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This work is copyrighted to the author © 2005. Please
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How I Became a Ladyboy
by Girlie Ellender (oaktownsissy@yahoo.com)
Quick Proofread by AB-2005
***
An adolescent boy discovers a penchant for cross-
dressing. One afternoon, while masturbating in his
mom's high heels and lipstick, he is caught by her
boyfriend. That's when the boy and the boyfriend
proceed to have sex. During the course of which the boy
is beaten and raped. (MMm, ped, cd, v, rp)
***
I've been getting hard-ons and playing with my dick
almost since I can remember. I recall one fantasy in
particular that I indulged in when I was 7. It involved
a cute little girl in my catechism class. Her name was
Lucinda. She was a bouncy little blonde, and my fantasy
involved stripping her nude and whipping her with
thorns. I had such erections over that.
I was pretty much of a sissy growing up. I never knew
my father. My mom told me that he had died soon after I
was born, but I was later to discover that my mother
had never married, and that the space on my birth
certificate for "Father" was typed: "UNK."
Mom was basically a slut. She worked a succession of
factory jobs, and had a succession of boyfriends. I
used to watch her on Friday nights in her tight dresses
and high heels, applying her lipstick before going out
for the night. Sometimes she would bring men home, and
later I could hear them making love in her bed.
When I was around 12, Butch moved in. We lived in a
triple-decker apartment house on the east coast. Our
apartment was on the first floor. Butch and Mom would
sit around drinking and watching porno movies. Then
they would fuck, usually in Mom's bedroom, but
sometimes right there in the living room. I began
masturbating then, thinking about them having sex.
Butch was in his late 30s. He had spent time in prison,
and though he wasn't very tall, around 5", 8", he was
heavily muscled and had lots of tattoos. Sometimes he
would grab me and pretend to wrestle with me. I
remember feeling really turned on by the feel of his
arms around me. He kept a stack of fuck magazines in
the basement.
Sometimes I'd sneak down and watch him masturbate while
looking at the pictures in the magazines. He would
strip naked and jerk off for hours sometimes, before
finally blowing his load all over his hairy belly. I
could see the semen on his fingers. He had a big cock;
I'd say about 8 inches.
After a few months, I began going to the basement to
jerk off to Butch's magazines. The girls were gorgeous
and so were the men. Looking back on it, I realize I
was identifying with the women in the photographs.
Once, I was in my Mom's room, and on impulse I took her
lipstick and applied it to my mouth. It was a cherry
red and when I looked at myself in the full-length
mirror I was shocked.
I looked like a woman! Not a girl, but a sexy woman! I
got an instant hard-on. My hair was shoulder length
then, and blonde. I immediately stripped nude and
grabbed a pair of Mom's high heels. Oh fuck! I was as
sexy as any of those bitches in Butch's magazines.
After that I never jerked off unless I was in heels and
lipstick.
One rainy afternoon, when Mom & Butch were at work, I
went down to the basement to jerk off. I stripped nude
and stepped into the pair of 4-inch heels I had
appropriated from Mom's closet, & applied a thick coat
of sexy red lipstick. Then I lay back on the ratty old
sofa to jerk off. Occasionally I would get up and strut
around in front of the big mirror. I was doing this
when suddenly I heard a long drawn out wolf whistle,
like the way construction workers whistle at girls in
miniskirts. I froze, my heart beating wildly. Then
Butch stepped out from behind the doorway. I tried to
grab my robe from the couch to cover myself, but Butch
was quicker. He snatched it out of my hands and threw
it behind him. "Please, Butch," I begged. "Don't tell
Mom, please!"
Butch was rubbing his crotch and looking at me
strangely. He shook his head. "Like mother like son,"
he said. "Or should I say daughter?"
"Butch, could I have my robe please?" I asked him.
"Why would you want to cover up that beautiful body,
girl?" Butch said. "I mean it, you are fine as fuck."
Before I could answer butch stripped off the tight t-
shirt he was wearing, and stepped out of his jeans. He
pulled down his jockey shorts and kicked them aside.
His dick was rock hard. He crooked his finger toward
me. "C'mere," he said.
I walked toward him, my head reeling. When I got closer
he grabbed my arm and pulled me close up against him. I
gasped as my soft nude flesh came up against all that
hair and muscles. He held me close, crushing me up
against his bare chest, his big hands squeezing the
flesh of my ass. He bent his head and his mouth found
mine, his tongue snaking into my throat. Oh god, my
dick was hard again. My hand reached down and felt of
his erection. "Oooh, yesss, baby," he moaned.
"You gonna to suck it? That's right, baby, get down and
suck my cock," he said, pushing me by the shoulders to
my knees. His hard cock brushed up against my cheek. I
took it in my hand and the head was close to my mouth.
Cum was forming on the head and I flicked my tongue and
lapped up the beads of pre-cum from his cock. 'MMM! Cum
tastes good,' I thought. I engulfed the entire head of
his penis into my mouth and began sucking his cock.
He was groaning in pleasure as I ran my mouth up and
down the entire length of his glistening cock and
sucked his balls up into my mouth. Butch's hands were
entwined in my blonde hair and he was using his fist to
control the movements of my bobbing skull. He sat down
on the sofa and lifted his legs, exposing his hairy
anus. I wasn't sure what he wanted. "Eat my ass," he
said. I put my face close and drew back. "What's the
matter?" he said.
"It stinks," I told him. He still had his fingers
entwined in my hair, and he pushed my face up into the
cleft of his ass.
"You love it," he said. And he was right.
It did stink a little, but the intermingled odor of
sweat & the faint scent of shit had an aphrodisiacal
effect on me, and I began eating out his bare anus with
abandon. I must have eaten his ass for 10 minutes – I
mean – my fuckin' jaws were getting numb, when Butch
told me to suck his balls and cock some more. I was
knobbing his cock really hard when he pulled my head
back, his saliva glistening penis withdrawing from my
hungry yap as he did so. "Why, Butch?" I whimpered. I
had assumed that Butch wanted to cum in my mouth and I
was working really hard for that reward.
"Because, baby," he said. "I'm gonna fuck you." And he
pulled me up from my knees so that I was lying up on
his big chest. Again his mouth found mine and our
tongues were snaking around one another.
As we kissed I was squeezing and choking on his erect
cock. One of his big hands was on my ass. He removed it
briefly and put one of his fingers in my mouth. "Get it
wet," he whispered hoarsely, and I sucked his finger,
coating it with saliva. He reached down and I felt the
finger at my anus. Butch began kissing me again, and
his finger worked into my ass.
Fuck! I felt like such a fuckin' whore! I mean, I was
wiggling my ass on his thick, calloused finger, just
like any horny puta! Butch kept whispering, "You want
some cock, baby?" And I kept whimpering, "Yes, Butch, I
really need some cock, daddy!"
Finally Butch said, "Ok, sissy. There's a tub of grease
in the dresser over there. Go and fetch it to me."
I stood up and started to step out of my heels. "Uh
huh," Butch said. "You keep the fuckin' high heels on.
I want to watch you walk in them. And put some more
lipstick on."
I applied a fresh coat of lipstick and walked as sexily
as I could across the room to the dresser where Butch
said the grease tub was. I opened the drawer and saw
it. It was a big jar of Vaseline. The jar was dirty and
had no cover. It was half empty. And there were pubic
hairs all over the Vaseline. I was thinking, oh god!
This guy is gonna stick that big thing in my ass! I
just know it's gonna hurt! But I wanted him to fuck me
so badly that the thought of the pain I was going to
have was outweighed by the desire to have this man
inside of me
I walked back to where Butch was sitting straddle
legged on the sofa. I could hear the rain coming down
outside. Butch had his dick in his hand and was jerking
off. As I got near him he reached out and ran his hand
up and down my bare legs. I shivered with anticipation.
"Damn, sissy!" he said. "You got some silky ass legs!"
He laughed. "Fuck! Do you know what they do with people
like you in prison?"
I didn't answer; I was enjoying the feel of his rough,
strong hands on my silky legs.
"Get down and suck my dick some more," he told me.
I didn't hesitate to obey him. The feel of his erection
in my mouth was heavenly! As I blew him he took a
couple of fingers full of the grease and reached back
to finger fuck my ass. Now it felt wonderful! The
Vaseline made his finger slide in and out, right up to
his big knuckles. I was wiggling my hips as he finger
fucked me.
Finally he said, "Ok, sissy, grease my cock up."
The grease tub was sitting next to him on the sofa. I
took a gob of the grease in my fingers and coated his
penis with it. Butch gave me an old towel and I wiped
my hand off. "Get up on the couch," Butch said,
instructing me to kneel on the sofa, facing the
backrest.
Butch climbed up behind me and began kissing on my neck
and bare back. I could feel his big strong arms around
me as he was kissin' on me. I could feel his dick
pushing up between my thighs and oh! I wanted it in my
ass so badly. I could feel Butch's sandpapery face up
against mine from behind. He was whispering in my ears
as he nibbled on the lobes, "I'm gonna fuck you, you
little ho!"
His words thrilled me. I reached back through my legs
and grabbed hold of his erection. "Oh FUCK! It was SO
fuckin' HARD!" I guided the head of his penis to the
mouth of my hungry anus, and he began to push, to
thrust.
Suddenly it found the hole and tore in. "OH – FUCK!!" I
screamed in pain as the head of his dick, as big as a
plum ripped into my ass hole. I began to instinctively
scramble to get off the sofa but a big muscled arm got
me in a headlock, while his other arm grabbed my left
arm in a wristlock that was so painful I forgot about
the pain in my ass. When I stopped struggling he let go
of my arm, but kept me in the headlock.
"Don't FUCK with me, bitch," he growled in my ear. He
got back on me and again I felt the probing erection
searching for my hole. I tried to press my legs
together, but Butch shoved his knee in between my
thighs and forced them apart. Then I felt a searing
pain as he tried to push the head in. I squirmed
violently and screamed.
That's when he hit me, hard, with his fist on the side
of my head. So hard I saw stars. A knot quickly rose,
shutting my right eye almost completely. Then he hit me
again, just as hard in the mouth, causing my upper lip
to swell grotesquely. Then he mounted me like an
animal, like a steer mounts a cow, and forced the head
of his cock into my ass. I was screaming, but no one
could hear because Butch had his big hand clamped over
my mouth.
He was grunting like a savage animal as he worked his
throbbing cock inch by inch into my ass. Finally, when
he was in me balls deep, he relaxed the headlock and
put his arms up under my arms and grabbed me by the
tits, pulling me close to him, my back up against his
big chest. He was growling and slobbering on my ears,
neck, and bare back. Slowly he began to fuck me, all
the way out, all the way in. At first it hurt like
hell, but as he increased the tempo of his strokes, it
began to feel good.
As Butch ass fucked me his hands were all over me – my
tits, my belly, my bare legs – everywhere. My dick was
hard again and I was wiggling my ass to meet his down
stroke. What a WHORE! I was totally writhing naked in
my boyfriend's big muscley arms as he raped me on the
dirty sofa.
Butch was fucking me and ramming his dick into me so
hard you could hear the slap of bare flesh on bare
flesh. His dick felt like it was actually swelling
inside of me, getting bigger, thicker. I began to use
my ass muscles to bear down on his erection. On every
down stroke, when his cock was buried up to the balls,
I would squeeze down and grip his cock with my ass
muscles, and when he withdrew I would maintain my grip,
so that I was literally milking him with my anus.
Finally, his entire body tensed and I could feel his
penis jumping and twitching uncontrollably inside of
me. He had his arms around me under my arms and he
yelled loudly and ejaculated deep into my belly. As he
came his arms tightened around me and I thought my ribs
would crack. I began milking his cock from inside and
Butch was shouting out in hot pleasure as I milked
every last drop out of him into me.
Slowly Butch relaxed his grip and lay exhausted on my
back. Then he eased his big greasy cock out of my anus.
It felt exactly like I was taking a big, constipated
shit. I turned around and Butch took me in his arms and
kissed me. "Oh, baby," he said, kissing my battered
face. "Why'd you make me get so pissed off? I'm sorry
baby, I promise I'll make it up to you, honey. I
swear!"
"Oh, Butch, I love you so much!" I said, crying. "I'm
sorry, too, honey," I told him. I lay in his arms on
the sofa for the rest of the afternoon, and just before
Mom came home, I gave him a blowjob.
We made up a story for Mom to explain away the beating.
Butch told her that I had gotten in a fight with a
bully at the mall. "You should have seen the other
guy," Butch told her, mussing my hair.
END
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The author does not condone child abuse, this story is
meant as an erotic fantasy not real life. Anyone acting
out such scenarios in "real life" can look forward to
many unproductive years getting it up the butt by a
fellow convict in their local prison.
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Kristen's collection - Directory 35