Date: Thu, 20 May 2021 18:14:20 -0700
From: Pomo Wolf <pomowolf74@gmail.com>
Subject: Tony Became Trish (Lesbian/Incest, TG, oral, anal, b/MM)

Incest, TG,  oral, anal, b/MM

Author's Note:

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

Copyright 2021 Wolf, all rights reserved.

You may contact me at pomowolf74@gmail.com if you like.
All flames will be ignored.

                    Tony became Trish
                          By
                         Wolf

	I was born and raised in the hill country of Oklahoma.
Besides my parents there was my older brother, David. that
was just short of being four-years-older than me.  My broth,
David, was the jock in the family and girls fell all over
themselves trying to get his attention.  I on the other hand
was small for my age and had delicate features.  I often head
people say that I would have made a beautiful good-looking
girl.

	 I became fascinated with my mother's silky smooth
and sexy underwear and liked the perfume smell.  There was
also a musky odor in the crotch that smelled of her pussy
and asshole.  When I was about 8-years-old I started taking
her soiled panties out of the hamper in the bathroom.  I
would take them to my room and put them on.  At that age
her undies and bra were a little large on me but I would fill
the bra with socks.  Looking at myself would turn me on and
I would pull my dick either over the top of her panties or one
of the leg hoes and masturbate to a dry orgasm.  When I was
finished using her undies, I returned them to the hamper
before wash day.  I'm surprised that I got away with my
fetish as I did.

	My brother bragged to me after a date with his first
girlfriend that he had fucked her when he was 12-years-old.
He took pride in telling me all about his dates.  He jokingly
told me that I was as cute as his girlfriends.

	One summer when I was about 13-years-old Dave
caught me in the backyard wearing one of Mother's
swimsuits and I was masturbating with a wad of Mother's
underwear wrapped around my dick furiously masturbating.
I was terribly embarrassed and tried to hide my dick and a
wade of her silken undies that I was using to masturbate
with.  I must have looked silly in her swimsuit.  Mom was not
a large woman so her clothes fit me by that age.

	"Is that Mom's suit you're wearing" was the sound of
the most awesome voice I knew.  It was Dave.  He had come
home to change after hanging out at a girlfriend's house.
Apparently, she wasn't in the mood that day and he just
kept looking at me.

	Dave said: "At first I thought you were the neighbor's
girl, until I took a better look.

	I almost started to cry but he was not threatening or
manipulating.  He was very nice and asked how long I wore
girl clothes.  I said for several years but they were too big
until lately they started fitting better.  He then floored me
when he asked if I liked boys more than girls.  I had to
remind him boys my age just met girls at the movies or ball
games and I had kissed a few but only a few.

	Then he asked me up front I I had ever kissed a boy
which I told him, no.  I didn't want to ruin any friendship and
no boy ever seemed interested in that.  I had a best friend
who was well hung for our age and I had a crush on him, but
he was totally into girls, I admitted it to Dave.  He asked if I
ever told him that I would like to be a girl at times?  I said
I'm already weirding out in Mom's bathing-suit with you.
How could I tell my best friend?

	Dave laughed and ran his hand over my hair and
before I knew it, he kissed me on the mouth.  He taught me
about French kissing.  He played with my tiny boobs a little
and told me: "If you want to learn more about what girls did,
to come to my room tonight after mom and dad went to
sleep."

	Later that night I snuck into his room, he pointed me
to his bathroom.  I found a note that said take off your
pajamas and put this on.  It was one of his girlfriend's cute
tops that was white with lace top and sheer and a pair of
white panties.  I did as I was asked, and when I joined him in
his room, he immediately told me: "Once I you learned how-
to-put-on makeup you could be as cute as any girl in our
school."

	  He kissed me.  It was so new but so different but I
felt his hard cock resting against my leg.  We laid on his bed
and he told me how to kiss down his chest and to lick his
penis like a lollipop until I got used to it.  Soon I had it in my
mouth.  I didn't gag like I thought I would.  He was so sweet
and called me sweet names, not fag or queer, it was baby
girl and sweety and how well I made him feel.  He warned
me he was going to explode in my mouth and I might gag
but try not to get sick.  It was okay to swallow or let it all fall
out.  I decided to go for it and tried to swallow all I could.  A
lot did drip out of my mouth but I didn't do too bad for my
first blowjob.

	David placed his hand on the panties and pulled the
front down and masturbated me until I squirted cum all over
myself.  I thought we were finished but I felt a finger slide
into the back of his girlfriend's panties.  He had used some
of the cum to slick up his finger before sliding his finger up
and down the crack of my butt before he stuck the finger
into my asshole.  He told me girls liked to be fingered before
making love.  After several minutes he rolled me over.  He
pushed his now hard cock inside me.  I wanted to scream
into the pillow but instead endured the pain for several
minutes.  Then it started feeling good then even better.  I
couldn't believe I was being fucked wearing his girlfriend's
panties and liking it.  It took him almost twenty minutes but
he finally pumped a hot weird feeling load into me.  I truly
felt like a girl.  We laid together for a while then decided our
parents were not ready yet to understand.  I changed back
and went to bed.  That was our first of many times we
fucked in his room.

	David sought me out after dates with his girlfriend and
she didn't feel like putting out.  Sometimes he would get
horny and get me alone in a secluded location like a barn or
a wooded area and have me give him a blowjob.  It was only
a matter of a couple of months before he propositioned me
to allow him to fuck me.  When I agreed to try it, he took me
to a barn that was secluded and brought along a jar of
Vaseline and lubed his cock and my asshole.  He had me get
down on my hands and knees and he mounted me doggie
style.  It hurt like hell and I bugged him to pull it out.  Of
course, he didn't pull out, and he placed his hand over my
mouth to muffle my crying.  I was sweating profusely by the
time Dave announced that he was cumming.  When Dave
pulled out of my ass, I simply flopped onto my belly and lay
in my own sweat.  I thought my asshole was bleeding when I
felt liquid dripping from my asshole.  I reached back and
wiped my asshole and looked at my fingers and saw that it
was Dave's cum dripping from my asshole.

	I was sore for a couple of days and vowed to never
allow anyone to do that to me again.  Dave was very
concerned about hurting me and assuring me that he would
never do that again.  Of course, that promises lasted until his
girlfriend crossed her legs when he wanted to mount her.  I
relented and allowed him to mount me.  At least this time it
was missionary and he jerked me off while he was fucking
me.  It didn't hurt as much but I did moan in pain with every
thrust.  Dave did kiss me after he came and continued
masturbating me until I squirted cum onto my belly and his
hand.

	David still dated.  I tried to keep meeting girls at the
movie or pizza place but at least once, sometimes twice a
week we would end up in bed or by the pool.  I remember
being jealous because I didn't get to go to his Junior prom
several months later.  But she didn't put out and he came
home.  Mom and dad were away skiing again and he asked
how quick I could put on one of mom's nicer dressers.  By
then I had learned to tastefully do makeup.  I thought we
would end up in his room as normal but instead we drove all
around.  He even took me to a local drive for a limeade.
Then we went to a secluded location and parked and he laid
me in his truck, dressed up on my back and his nice cock
slipped in and out of me.  It was like he was hoping we got
caught or someone saw his truck and told his girlfriend he
had another girlfriend.  Whatever, his motive I did my best
to be the best alternative prom date he could have wanted
and let him fuck me three times that night.  We got home at
sunrise.  I think a neighbor was a little confused but never
said anything.

	I don't know when my parents got wise to me being a
sissy but it did become apparent.  Mom and Dad had
separate bedrooms because Mom couldn't sleep while
listening to Dad's snoring.  One evening when Mom was
visiting a friend, and David was out with a new girlfriend,
come bedtime Dad came to my bedroom and invited me to
come to his room.

	When I lay on the bed Dad put his and on the crotch
of my pajamas and pulled my cock out and masturbated me
until I squirted cum all over myself.  I wondered what would
come next, before he pulled my bottoms down and rolled
me over onto my belly.  He stuffed a firm pillow under my
waist to elevate my butt.  It came as a shock when my father
buried his face in the crack of my butt and licked my asshole.
Then he spread my legs and knelt between my legs and
assumed the doggie position and he drove his cock deep
into my ass.  At least David had gotten me used to a cock in
my ass.  Daddy hammered my butt fast and hard.  At least I
was prepared for the feeling of cum dripping from my
asshole.  When he was finished, he wiped his cock off on my
butt.  He kissed me and sent me back to my room.  I exited
his room with my bottoms in hand.

	I had a lot to think about that night, I was still awake,
pulling on my cock, when I heard Mom come coming in.  I
heard her open her bedroom door.  I had a fitful night's
sleep.  My throbbing asshole was the only thing from
convincing myself that it had all been a dream.

	I was the first one up the next morning and dressed
and down stairs.  Mom was preparing breakfast and enlisted
my help.  While we were cooking the meal, she asked me:
"Did you enjoy yourself last night!"

	I was dumb founded when I realized that my mother
knew what took place last night.

	Then she added: "I have known about you wearing my
underwear for some time, and that David had been fucking
you.  I assume that you get off wearing women's clothes?"

	It took me a while to process what she was saying.
"You knew and didn't say anything?"

	"Honey, I want you to be happy with whatever turns
you on.  You don't need to feel guilty about liking to wear
women's clothes.  I would love you even if you want to
change your sex."

	"Really"

	"Do you want me to buy you an age-appropriate
wardrobe for a girl your age and size?"

	"Really"

	"Of course, I will, you brother and father will enjoy it
as well."

	Mom already knew all of my measurements.  She
started buying me everything I needed including "Baby Doll"
nightgowns.   I soon had a closet full of clothes for all
occasions.  I could dress like an innocent school girl or go
completely slutty.

	David had to be satisfied with fucking me before Dad
got home from work, because I slept in Daddy's bed most
nights.  Mom taught me everything a woman needed to
know.  Cooking, cleaning, and household accountings.  She
taught me how to walk and sit.  She insisted that I not act
like a campy drag queen.  My hair was long enough for her
hairstylist to teach me how to style my hair like the girl's
fashion for girls my age.

	The family no longer called me Tony!  I was Trish from
then on.  I made and spent a fortune performing in rag clubs
with the help of false ID from the age of 15.


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 pomowolf74@gmail.com