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Nifty - Gay - Adult Youth - David The Sissy Boy

Date: Fri, 18 Nov 2011 16:17:42 -0500 (EST)
Subject: David the Sissy-Boy (gay/adult youth, fetish, oral, anal. b/MMM...)


This story is a work of fiction and contains descriptions of explicit sexual
acts of boy's discovering their sexuality. It contains graphic scenes of
sex between an underage boy and adult males... If this type of content
offends you or you are under the age of 18 do not read it.

Author's Note:

This story is the property of the author. It can be downloaded for
personal reading pleasure or sending to a friend, but if you wish to re-
post them at your own site, please contact the author for permission.

If it is illegal to read such material where you live or if you find the topic
distasteful the please leave now. If you enjoy the story or if it evokes
memories of your own, please let me know. I am happy to write stories
from outlines.

Copyright 2011 Wolf, All rights reserved.

You may contact me at if you like. All
flames will be ignored.

David the Sissy-boy

       When I was a ten-years-old boy, named David, I lived with my
stepmother, named Elizabeth, in Trenton, New Jersey. Liz was a cool
woman she allowed me to have beers and smoke some of her pot while
she was out on dates. I was a small slender freckle faced blonde headed
boy, with long hair. I can honestly say that I made better looking girl
than a boy. I had to pull back my hair and put it in a ponytail while at
school, and endured all of the abuse, bullies could heap on me, because I
so girlie looking. Around home I preferred to let my hair down. I also
loved to put on girls short-shorts, and pretend I was a cheerleader. I
pictured myself teasing older men like girls do.

       One evening Liz confided to me that she was having finical
problems. She suggested that one way to get extra income was to rent
out the two rooms in the basement. They were fully furnished, because
we liked to use them during the summer, because they were cooler than
the other rooms in the house. She ran an ad in the local paper and posted
an ad on the billboard at the local supermarket. She interviewed a few
applicants, before selecting a couple of older men that she felt
comfortable with their ability to pay on time, and not being any bother.
Their names were Patrick and Samuel. They must have been in their

       I couldn't help notice the way they looked at me. They started
teasing me after they moved in. They always waited until Liz went to
work or called to say that she was sleeping out, (meaning she was getting
laid), before long they started showing me magazines of young sissy-
boys dressed up like girls in provocative poses. I couldn't help getting a
boner looking at the pictures. The two of them started buying me all
manner of girl's clothes, so that I could dress up like a girl. I even put on
makeup. I had watched Liz carefully to learn how to apply makeup
properly. I got a charge out of teasing these old men. They taught me
how to kiss like a girl with tongue. That excited me as much as it did

       It never failed to make their pants tent up. They were soon
teaching me to take out their cocks to play with, and eventually suck
their cocks. I loved to lick and suck on their balls, and the feeling of
their fat, silky smooth cocks in my mouth. It shocked me the first time
Pat came in my mouth. I spit out his cum, but Pat and Sam assured me
that good little sissy-boys swallowed cum. After that, I swallowed all of
the cum every time. It didn't take long before I developed a taste for
cum, and begged them to cum in my mouth.

       When summer came Pat and Sam convinced Liz and I to join
them for a vacation in Florida. While Liz hung out on the beach and the
pool, Pat and Sam took me to parties where I got to show off what a
good looking girl I made, and indulged in a lot of cock sucking.

       One evening while Liz was out partying, they took me to a party
where I smoked some pot, which made me feel very sexy. I was in such
a good mood that I didn't object when a man suggested that I allow him
to fuck me. I had no idea that anyone actually did anything like that.
But the idea that my asshole could be used like Liz's pussy gave me a
boner. The man played with my asshole, while I was still in a pair of
sexy thong panties. I had a painful boner by the time he took my panties
off. He greased up my asshole with some sort of liquid, then he had me
grease up his cock for him. To me it seemed very large, but I know now
that it was just an average adult male cock. My playing with his cock
had made him very hard and clear pre-cum was leaking out of the head
of his circumcised cock. He allowed me to control my first fuck, by
squatting over his hips, and lowering my butt down until his cock
penetrated my asshole. It hurt like hell, but I kept moving up and down
until I was actually sitting on his pubic bone. Then I bounced up and
down. When he was ready to cum, he grabbed me by my hips, and
pulled me down hard against his body until he was finished squirting his
cum into my ass.

       When I dismounted, it hurt whenever I tried to pucker my
asshole. He held a mirror under my butt, so that I could see my inflamed
asshole. My asshole was gapping open, and the opening was swollen and
very red. Cum was dripping out of the hole. He was telling me that it
would relax soon, and I would be sore for awhile. He assured me that
the more I got fucked the better it would feel.

       I don't know how many times I got fucked during that vacation,
but he was right, I soon begged men to fuck me. I was very proud that I
had my cherry taken, and was broken in so fast. All of the men down
there in Florida had been older men, that were retired and had moved
down there from the New England States. There was many a time that I
sucked a cock while another man was fucking my ass. There were even
times when I was jacking off older men while that was going on. I did
love tasting cum of these older men. Some of them had watery looking
cum, others had thick white cum. One of them that was constantly
chewing tobacco, and swallowing the juice, had cum that was an occur
color. Most of them had a salty tasting cum, but the tobacco chewer.
Cum tasted like tobacco. Some managed to save a squirt or two, to give
me a facial with.

       They liked to videotape the action for future parties, and always
wanted my made-up face covered with cum, and my mouth full of cum.
I enjoyed smoking pot, because it always made me feel hornier and
submissive too. I was always eager to suck cock and get fucked while
high, by older men. Having the old me call me their sexy little
cocksucker made me feel sexy too. The nastier their exclamations were
the hornier I got, and the more I loved it. They called me Puff the magic
cocksucker. My lips were always puffy and swollen, and my nipples
were swollen too, because they like to pinch them while fucking me.
They even stopped calling me David and called me Debbie, while I was
dressed up like a slutty girl. I loved teasing large groups of men, and
then swallowing all of the man cum.

       Liz knew what Pat and Sam were doing with me, and was cool
with it. She knew I was a sissy-boy. She even bought me girl's clothes
to make me feel comfortable at home. My lips were often swollen from
sucking cocks. From time to time I would come home with my bangs
caked to my forehead by dried cum.

       When we returned home after the summer Pat and Sam took me
to parties and public restrooms where they introduced me to glory-holes.
They set me up with dates, that would take me for drives into the
country, while I sucked their cocks while they drove. One time we took
a ride in a custom van. While the driver was driving around, I was in the
back sucking cocks and getting fucked hard and fast.

       One time a man that was dating Liz came by while she was at
work. He knew damned well that she would not be home, and I knew it.
He suggested that it would be nice if I gave him a blowjob. Getting the
chance to suck a cock of a man old enough to be my father turned me on.
While he sat in the recliner I sucked his cock until he came in my mouth.
I continued to play with his cock until he got another boner. He was
pleasantly surprised when I offered to let him fuck my ass. While he got
up, I pulled down my panties, and knelt in front of the chair with my
face buried in the cushion of the chair. The man straddled my hips, and
inserted his cock into my asshole. He fucked me for a long time. Sweat
was dripping from his face all over my back. I always wondered if Liz
ever found out that this guy was dropping by to fuck me, before she
broke up with him.

       Some guys dream about becoming a football hero, but I longed
for the day I could get breast implants and take female hormones. I
never wanted to have a beard or any other male features. I never wanted
to have a complete sex reassignment, because I did enjoy being able to
cum in men's mouth too. High school was hell for me, I got beaten up
regularly. It was interesting that some of the guys that picked on me in
front of their buddies also came to me for blowjobs too.

If you enjoyed the story and have a story you want me to write about
your introduction to the world of male sexuality, please send your outline
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Nifty - Gay - Adult Youth - David The Sissy Boy