Date: Wed, 19 Oct 2022 11:20:02 -0700
From: Pomo Wolf <pomowolf74@gmail.com>
Subject: Timothy Becomes Trish (Transsexual, Incest, oral, anal, b/MMF, f/f)

Transsexual, Incest, oral, anal, b/MMF, f/f

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, adults, and a teen female.  If this type of
content offends you or you are under the age of 18 do not
read it.

Copyright 2022 Wolf, all rights reserved.

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

                      Timothy Becomes Trish
                              By
                             Wolf

	I was born and raised in the hill country of Oklahoma.
Besides my parents I had an older brother that was just short
of being four-years-older than me.  My brother, David, was the
jock type 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 heard people say that I should have
been born a girl.

	 I became fascinated with my mother's smooth and sexy
underwear.  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
holes and masturbate to a dry orgasm.  When I was finished
using her undies, I returned them to the hamper.  I'm surprised
that I got away with my fetish as long as I did.

	My brother bragged to me after a date with his first
girlfriend that he had fucked her when he was 12-yesrs old.  He
took pride in telling me all about his dates.  He jokingly told me
that I was cute.  When I was about 13-years-old one summer
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 the
wade of her silken undies that I was using to masturbate with.
I must have looked silly in her swimsuit.  Mom was not apetite
woman so her clothes fit me by that age.

	"Is that Mom's bathing-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 thought you were the neighbor 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 had been
wearing girl clothes.  I said for several years that they were too
big at first but lately they started fitting better.  He then
floored me when he asked if I liked boys more than girls.  I had
to remind him that boys my age just met girls at the movies or
ball games and I had kissed a few but only a few.

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

	Dave laughed and ran his hand over my face 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 do, come to
my room tonight after mom and dad were asleep.

	Later that night I snuck into his room and 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 he asked, and he immediately told me: "Once
you learn how-to-put-on makeup you could be as cute as any
girl in our schools."

	  He kissed me.  It was all new but so different but I felt
his hard cock against me.  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 that 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 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 I agreed to try it, he took
me to a barn that was secluded and had me give him a
blowjob.  He had brought along a jar of Vaseline and a pair of
his girlfriend's panties.  He had me put them on while he lubed
his cock.  He hugged me and I felt his finger slide into the back
of her panty.  Then I felt it slide into the crack of my butt.  He
had used some of his cum to slicken his finger.

	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 loose hay 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.  He had me get down on my
hands and knees and he mounted me doggie style.  It hurt like
hell and I begged him to pull it out.  Of course, he didn't pull
out, and he placed his hand over my mouth to muffle my
complaining.  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.

	Dave told me that he didn't think our parents wouldn't
understand my feelings.  I changed back into my clothes and
we returned home.  That was our first of many times he fucked
me.  He even got one of his girlfriend's nightgowns to swear
when he fucked me in his bedroom.

	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 promise 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 kissed me
after he came and continued masturbating me until I squirted
cum onto my belly and his hand.

	He still dated girls.  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 the
park and he laid me in his truck, dress up on my back and his
nice cock slipping in and out of me.  It was like he was hoping
we got caught or someone see his truck and tell his girlfriend
he had been fucking another girl at the local lover's parking
location.  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 hand on my pajama
bottoms and squeezed my cock.  He masturbated me until I
came 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 spit on 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 pajama 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 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 got up early the next morning, got dressed and went
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 had taken 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 and
anal sex!"

	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 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, your 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.  How to
fix my hair, apply makeup, how to dress, walk, sit, cook,
cleaning, and household accountings.  Mom was the most
helpful.  She had a talk with her gynecologist.  After the three
of us had a long talk, I was given a regiment of estrogen shots
and pills.

	It didn't take long before my body made noticeable
changes.  My hair was long enough to have my hair styled with
a fashionable look.  My voice changed to a softer feminine
range.  My hips and butt got noticeably bigger and softer.  My
breasts got bigger, but were not as big as I wanted them to be.
Mom made arrangements for the two of us to fly to see a
famous plastic surgeon in the Beverly Hills community.  After
the consultation arrangements were made for the two of us to
stay in a hotel while I was prepared for breast implants.  There
was some time spent stretching the skin before the 400 cc
implants were inserted.  My nipples and areolas had already
enlarged due to the hormone treatments.  We enjoyed the
beach and shopping while the incisions healed.  During our
stay in southern California Mother taught me all about lesbian
love.  What more could she want?  She has an adorable
daughter to eat her pussy and still able to fuck her with a real
cock.  The last thing was to have my sex changed legally.
When we returned home, I was a very attractive brunette with
a functioning cock.

	Dave was in college by that time.  By that time, he was
fucking college coeds, and he had very little interest in high
school girls.  When he was in town, he did enjoy fucking me.
Dad got off fucking his new daughter several times a week.
Mother and I also enjoyed our private times together.  We
enjoyed everything lesbians can do including her fucking me
with a dildo, and I also was thrilled to fuck my mother in her
asshole, cunt and mouth.  When I returned home, I entered
high school none of my previous classmates recognize that the
boy they knew as Timothy was the girl they met as Trisha.  I
became close friends with a group of girls that were very
liberal.

	The most popular girl in high school was a girl named
Linda Ferraro.  She was a classic beauty with long flowing
chestnut hair and big brown eyes.  She had the body that
would turn heads.  She taught dance at the City Recreation
Center, and all of the high school band auxiliary units were her
students.  They included the majorettes, flags, and drill team.
She was the head Drum Major, Homecoming Queen, Queen of
the Junior Senior Prom, and voted the most popular girl in her
class.  Both of us happened to be in the sixth period gym class.
She sought me out and befriended me.

	She tried to recruit me into joining one of the auxiliary
units of the band.  She assured me that she would teach me to
be a majorette.  I tried to deflect her efforts.  Just the same she
sought me out to have lunch with me, and include me in her
group of friends.  She went out of her way to come home with
me and meet my parents, and bring me to her home to meet
her parents.  While we were together Linda was very talkative.

	She had noticed that I was very shy when it came to
changing clothes during gym class, and never showering after
class.  She asked me if I had some sort of religious reason I
wouldn't undress in front of the other girls.

	I assured her that I had a personal reason for not
allowing anyone seeing me naked, but would not discuss the
reason.

	Linda was not shy about discussing her sexual exploits.
She bragging that she had fucked almost all of the best
football, basketball, track stars, and baseball players.  She even
admitted to having sex with some of her girlfriends., and some
of the male and female teachers.  She told me that she would
like to have sex with me.

	I told Linda that there was a very good reason why that
was not possible.  I finally told her that if the reason I didn't
have sex with anyone and my secret got out I would be in
trouble.  I would probably have to move away.  That aroused
Linda's curiosity.  She kept pressing me to tell her what was so
devastating that I couldn't tell anyone.  After several days of
her pressing me to tell her my secret I finally broke down and
told her that if I told her my secret, she couldn't tell anyone!
After she agreed to never tell anyone, I told her that I was a
transgender female.

	Linda looked puzzled: "What does that mean?"

	I told her: "I was born a male and I have undergone
hormone therapy and plastic surgery to enhance the size of my
breasts.  My family and I had my birth certificate legally
changed to reflect that my sex is female and my name was
changed from Timothy to Trisha."

	Linda was still puzzled: "So, why would anyone know
your secret if they saw you naked?"

	I said: "I still have male genitals.

	Linda asked: "Why didn't you have your penis made into
a vagina?  I hear they are able to make very realistic pussies."

	I blushed and said: "I enjoy receiving anal sex and being
able to fuck males and females!"

	Linda was very excited: "Who are you fucking?"

	I asked: "Do you remember my older brother David?"

	Linda thought before she said: "He graduated a couple
of years ago and was a fullback.  I hear he is attending The
University of Colorado."

	I said: "That's my brother!  He started fucking me when I
was 13-years-old.  My parents found out and both of them also
fuck me.  That same year Mom and I spent the summer in
Beverly Hills, California getting plastic surgery.

	Linda wanted to see me naked, so I removed all of my
clothes in her bedroom.  She had to feel my tits and marveled
at how natural they felt.  When I dropped my panties, she
couldn't take her eyes off of my cock.  She said: "I have never
seen anything like this before!  You are possibly one of the
best-looking girls I have ever seen, and yet you have a cock
that is above the average size.  Does it still work...I mean can
you get a hardon and cum?"

	I couldn't help smiling: "I haven't gotten any
complaints."

	Linda moved to her door and locked it.  "This is going to
be a new experience for me.  I have had sex with plenty of
males and had sex with almost as many females, but I have
never had sex with someone that would be like having sex with
both at the same time."

	She quickly removed all of her clothes and got on the
bed with me.  We kissed each other with our tongue and felt
each other's tits.  We took turns sucking on each other's tits.
While I fingered her cunt and she masturbated my cock.  We
stopped short of making each other have an orgasm.  She lay
on her back and I mounted her in a classic 69 with me on top.
While I ate her pussy, she sucked my cock.  We interrupted the
oral sex because she wanted me to cum in her cunt.  We
became almost inseparable.  We started dating guys together.
That way guys were fucking her while I was fucking them.

	We became life long friends.  We even went to
Oklahoma University together as roommates.


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