back save

Nifty - Gay - Incest - Sissy Boy Forever

Date: Mon, 01 Dec 2008 17:56:57 -0500
From: Wolf <>
Subject: Sissy-Boy Forever (gay/incest, b/M, b/MM)


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 deceitful 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 2008 Wolf, All rights reserved.

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

Sissy-Boy Forever

       It is hard to be a sissy-boy in a family of
rednecks. Jason was the youngest child in a family of
four boys. His mother was protective of his feminine
side. She allowed him to let his black hair grow to
shoulder length. He had to endue a lot physical abuse
from his older brothers because his effeminate
behavior. School was no better.

       He was not very athletic so the boys never
picked him to play any games. Besides he didn't like
being knocked around. His aversion to outdoor games
made him more of an indoor type as a result he had
pale skin and soft skinned. From the back he was
mistaken for a girl.

       He would much rather play with the girls. His
best friend at school was a girl that protected him
from the bulling by the boys. When he would visit
her home she would style his hair like a girl. Even if
she put it in a ponytail she would give him bangs and
curl the hair in the tail. They would put on makeup.
She taught him the proper way to apply makeup. She
even envied his long eyelashes and blue-green eyes.
They were very close to being the same size too. She
spent hours admiring what a pretty girl he would have
been. From the age of 10 she would allow him to wear
her sexy panties. He would return them to her for

       When he reached the age of 13 his mother also
indulged his fascination for makeup and women's sexy
underwear. She would buy him girl's clothes and allow
him to wear them around the house. When he
reached the age of 15 he would even wear makeup in

       His feminine appearance always drew the
attention of adults. Women commented of what a
pretty boy he was. Men would tell him they would like
to fuck him. The idea appealed to very much. When
he learned from his brothers that there were men
that like to have sex with sweet little boys like him,
he could think of nothing else. He was jacking-off
long before he was able to cum.

       Eventually he had the chance to find out what it
would be like to have sex with a man. He was walking
home just before he turned 13 and a man approached
him. The man was very flattering about his looks.
When the man suggested that he accompany him
home because he would like to see what he would look
like in some dresses he had Jason accepted his offer.

       The man led him to his house and it was not far
from his own home. He felt a little safer knowing he
was so close to home. As soon as they were behind
closed doors the man wanted to touch his body.
Jason enjoyed the way he gently stroked his body.
The man wanted to get him relaxed. So he offered
to share some marijuana with him.

       Jason knew his older brothers smoked joints
but they would never share it with him. He agreed to
try it. The man had a little glass pipe that he filled
with a small amount of weed and lit up. He held in the
smoke as he passed the pipe to Jason.

       Jason had never smoke pot before and exhaled
as soon as he had taken it into his lungs. They were
both coughing. The man told Jason that he had to
hold the smoke in his lungs as long as he could. The
second drag Jason took he tried to hold it in as long
as possible. He was sputtering as the urge to cough
was strong. Eventually he had to let it go. It took a
few minutes before Jason felt anything. The first
thing he noticed was it seemed to get darker. It felt
as if his body was disconnected from his mind.

       The man brought out some girl's dresses that
were very frilly which got Jason excited. He peeled
off his clothes with no thought about the fact that
he was getting naked in front of a stranger. She put
on the tight fitting little lace panties before putting
on the dress. He also put on ankle socks and Mary-
Jane shoes.

       When the man pulled him onto his lap and
started feeling him up it felt like it was someone
else's body that was being touched but it felt good.
His little penis was as hard as it had ever been. The
man had his hand under his dress rubbing his little
boner through the sexy panties. Eventually the man
slipped his hand down the front of the panties and
took hold of his boner with his thumb and a couple of
fingers and jacked-him-off while he was kissing Jason
on the mouth. Jason was in heaven and was returning
the kisses with enthusiasm as the man cupped his
little scrotum. The man's finger traced the seam
down the middle of his sack right to his little asshole.

       Jason could not believe how good it felt having
the man play with his asshole. When the tip of his
finger penetrated his asshole it shocked him and he
puckered his asshole tightly on the finger tip. It
hurt so he relaxed and when he did the man stuffed
his finger up his ass all of the way. When the man
started stroking his finger in and out Jason could not
believe how his little cock reacted. It was bouncing
up and down against his smooth pubis.

       When the man removed his own pants Jason
knelt before him and took his cock in both hands and
started sucking on the knob until he got a mouthful
of cum. He was shocked by the warmth of it but he
didn't mind the taste. He had had to change clothes
before going home but he had every intention of
returning as soon as he could.

       He would drop by to visit the man two or three
times a week. When he would drop by the man would
often greet him wearing silk jogging shorts. He never
had underwear on under them so that his cock and
scrotum would be exposed when he sat down with
Jason sitting on his lap. That way the sissy-boy could
play with his cock while the kissed and the man felt
him up. He was having the greatest time of his life.

       It was not so bad at home by that time. His two
oldest brothers were in the Army by that time and
the other brother was away at college. There were
just his parents at home. His father had very little
to do with him because he didn't approve of him
wearing makeup. There was no loved lost between

       One day when Jason got home his mother had
left a note that she was visiting a friend of hers and
would not be home until later that evening.

       Jason started making dinner for him and his
father. When his father got home he read the note
and didn't say much about it. He took a shower while
Jason finished making dinner. When his father came
back to the kitchen he was dressed casually. Dinner
was quiet. His father went to the living-room to read
his news paper while he watched TV. Jason finished
the dishes and joined his father.

       He was watching the TV until his father
finished reading the paper. He did not see the way
his father looked at him. He told Jason to come to
him. As Jason stood up and approached his father his
dad was unzipping his trousers and pulling his cock out
of his pants. He was holding it by the shaft as he
told Jason to suck his cock.

       Jason knelt between his legs and started
sucking on his father's cock. When his father's cock
was fully engorged with blood his father stood up and
pushed Jason backwards and onto his back. His
father unfastened his pants and pulled them off of
his legs. His father had a snarl on his face when he
saw the delicate lace panties on his son. He said, "If
you want to be a sissy-boy you might as well be one."
With that he pulled them down to his ankles and
lifted his legs up knelt on the floor with his knees
touching Jason's smooth butt. While he held Jason's
ankles with one hand he guided his cock against the
virgin rosebud. Jason had never had anything larger
that that man's finger in his ass before. Now his own
father was forcing his cock into his asshole and the
pain caused tears to well up in his eyes and he
pleaded with his father to take it out.

       There was no stopping his father at that point.
He stuffing all of his cock in Jason's ass and fucked
him hard. By the time his father squirted cum in his
ass Jason was beyond crying any longer. His asshole
felt like it was on fire. When his father pulled his
cock out of his ass felt like his guts were going to fall
out of his asshole. He felt liquid seeping out of his
asshole and pooling under his butt. He thought it was
his own blood. It was not until he sat up and moved
back that he saw that the liquid was not blood. It
had to be his father's cum. He slowly stood up and
waddled to the bathroom to shit and take a bath.

       He avoided being around his father for awhile.
Nothing was said between them about what had
happened. When he visited his adult friend he told
him what his father had done. The man wanted to
inspect his asshole. He told him that now that he was
not a virgin it would get easer to be fucked. They
talked about it and Jason agreed to try it again.

       The man retrieved a jar of Vaseline from the
bathroom and greased up Jason's asshole and his
cock. When he had Jason lay on his bed in the
missionary position and placed Jason's heels on his
shoulders as he guided his cock into the little
rosebud. The man took it slowly and watched Jason's
sphincter spread open to accommodate the knob. He
would stop and pull back a little when he saw the pain
on Jason's face. He took his time and slowly worked
his cock in until his pubic hair was pressed tightly
against Jason's little scrotum. When he started
fucking Jason he took hold of Jason's cock and
jacked him off while he fucked him.

       When the man was finished Jason wanted to see
his asshole so the man held a small makeup mirror
between his legs so that Jason could see his own
asshole. It was the shape of the man's cock and the
skin around the opening was swollen and an angry red
color. His asshole hurt but was a little numb. It hurt
even more when I tried to pucker his asshole up. The
two of them bathed together before Jason had to go

       Jason waited a few days before visiting the man
to try that again. When they retreated to the
bedroom Jason found that it was not as
uncomfortable this time to take is cock up his ass.
The next time they did it Jason actually climaxed and
squirted cum all over his own belly. He became a
regular little cock hound after that.

       It was not long after that his mother was
spending an evening out with her girlfriend again.
This time his father came to his room in only his
boxer shorts. Jason didn't resist as his father
prepared to fuck his ass. His father was just as
rough as before only this time while his father was
fucking his ass Jason shot cum all over his chest and
chin. His father watched Jason squirting cum all over
himself before he filled Jason's ass with cum. He had
Jason suck his cock clean before he went back to his
own bedroom.

       Again nothing was said about what had taken
place. When the weekend arrived his father told his
mother that he was taking Jason with him to watch
football with his buddy. Jason was not thrilled about
having to watch football all day with his father's
buddy. He wanted to object but his gave him a look
that told him to keep his mouth shut.

       His father's buddy was the kind of man that
frightened Jason. He was about six-feet tall and
could have been the model for Pop-Pye the sailor
man's adversary Bluto. He was a large dark hairy man
that always looked like he needed a shave. He tended
to be chewing on the butt of a cigar all of the time.
Jason was frightened by him. So he was not happy
about being forced to go with his father.

       When the two men settled down to watch the
game his father told him to bring them a couple of
beers. When he returned with two cans of beer his
father said, "Take off you pants Son and show Bill
your panties!"

       Jason knew better than to object. He simply
unfastened his pants and pulled them down to his
knees. Bill reached over and felt the crotch of the
black lace panties. He had a nasty grin on his face
with a stinking cigar butt sticking out of his teeth.

       Jason was still a small youth of no more than
120 pounds. The man's hands were large and rough.
Hell! Each of his fingers was larger than Jason's
little cock. He didn't move as the man pulled his
panties down to have a look at his little pecker and
balls. He rolled the soft flesh in his callused fingers
and pulled on his little cock. He turned Jason around
and made him bend over and support himself by
holding onto the edge of the coffee table. He spread
Jason's butt and ran a finger up and down the crack.
Jason did flinch with the big index finger invaded his

       Bill made him knee across the table. When
Jason looked at his father he was taking off his
clothes. He had to turn his body to see what Bill was
doing. He was taking his clothes off too.

       Jason was starting to sweat when he saw what
Bill looked like. To begin with his chest had to be at
least 50-inches around and his waist was close to 60-
inches around. When Bill turned his back to him to
take off his pants Jason saw that not only was his
back hairy there were hairs on his butt. When Bill
turned to face him he saw that the front of his body
was just as hairy. The sides of his belly didn't have
much hair because of the friction of his arms. The
hair on his chest was thick and turning gray. When
Jason checked out his crotch he saw that Bill's cock
was nestled in a think mat of pubic hair. The balls
were covered in hair but the cock was frightening to
him because he had never seen a cock like that
before. It was larger than anything he had ever seen
and the skin was dark too. This was the first un-cut
cock he had ever seen. The foreskin reminded him of
the eggs in the movie "Aliens". The skin covered the
knob and some of the skin dangled past the knob. Bill
skinned back the foreskin to show Jason that he had
a knob like any other man. The head was wet and it
smelled so strong Jason could smell his cock from
where he was laying.

       Bill placed his big meat hooks on Jason's butt
and spread the cheeks and spit on his asshole. Jason
cringed because he knew what was coming. His
father came around the table and grabbed a handful
of hair as he stuffed his cock in Jason's mouth.
While he was accepting his father's cock Bill was
stuffing that fat baseball handle sized cock into his
boy-pussy. He would have screamed but his mouth
was full. There was nothing to do but endure the
fucking. To his astonishment he squirted cum all over
the coffee table before either of the man came in

       The men had a couple of more beers and talked
about what a sweet sissy-pussy Jason was. They
fucked him again before the second game for the day
was over. Jason was finally allowed to bath and get
dressed before his father took him home.

       Jason did everything he could to walk normally
but he must have looked like he was waddling a little.
His mother never mentioned it though. It was not
until he was getting undressed for bed that he
checked his pocket and found a slip of paper with
Bill's phone number on it. He had no intention of ever
seeing him again. He tossed the paper into his
trashcan and went to bed.

       In the morning he woke up with a raging hard-on
and fished out the slip of paper and put it in his
backpack. He called Bill and asked him if he could
drop by after school. Bill assured him that he was
welcome and he would have a stiffy waiting for him.

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 to

back save

Nifty - Gay - Incest - Sissy Boy Forever