Shemales Porn Stories
Page 3

How it all began

My mother had 4 c***dren, 3 girls and a boy. I was the youngest. My s****rs were 5, 4 and 2 years older than me. Being the youngest I had to do as my older s****rs told me, including being dressed up as a dolly to play with when I was 4. When the oldest started wearing make up at 11, I was used for practice by all three of them, so I learned how to apply it myself.

When the oldest graduated from high school and went into the Army I was the same size as my youngest s****r and took to trying on her clothes. The feel of her bra’s & panties was awesome compared to my cotton tee shirts & briefs... Continue»
Posted by Andii18 1 year ago  |  Categories: First Time, Group Sex, Shemales  |  
  |  22

The Making of a Sissy (Part 2: The Metamorphosis)

As the morning rays of sunlight pierced through my bedroom window I was awakened from the most intense dream, reenacting what had happened the night before. My throbbing hard little cock was gently humping against the sheets of my bed while I couldn't stop thinking about the amazing big black cock I had in my mouth just hours ago. I could still taste him on my tongue, and I could smell him on my lips. What had happened to me? Why was I so turned on by all of this? I thought to myself, "Maybe it was just a one time thing, like a one night stand." My mom had been dating a lot lately, so I ... Continue»
Posted by briantid8 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
  |  13

I slept with a porn star

This is a true story. I left out her name but if you need to know message me.

I was on Tinder late Wednesday night. I'd gotten home from a first date with a very attractive woman with absolutely no spark I knew there wouldn't be a second date and that was fine. Laying on the couch, flipping through the profiles, I swiped right on a very attractive younger woman. I didn't look at her profile and moved on. A couple minutes later I got a notification that she swiped right on me. So, I figured I'd check out her full profile this time and saw she was transgendered. That was fine - I'm pansexual.... Continue»
Posted by artbasel 10 months ago  |  Categories: Celebrities, Shemales  |  
  |  6

My Mom The BBC Shemale and My Wife, The Virgin

After the wedding, we didn’t move out from my mother’s house as my salary is not enough to cover our expenses and since my wife is also not working.
Mom allowed us to stay with her since she will be living alone if we move out.
I had no issues with this as I save my expenses and on an off without my wife’s knowledge I can suck mommy’s dick and be fucked by her. Mom is also looking forward to this encounters I suppose.
Her age is pushing 60 but she still looks attractive most probably to her testosterone production that delays her menopausal syndromes. She still maintains her cock size which... Continue»
Posted by yarracuda 1 month ago  |  Categories: Mature, Shemales, Taboo  |  
  |  5

Schoolgirl Sissy Crossdresser and Her Black Daddy

WARNING: This fictional story contains graphic sexual/profane terms and scenes. This is a work of fiction, a fantasy, and is meant to be enjoyed by horny fucking perverts like myself.

I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning...

It was summer time. As always I spent my summers hanging out and occasionally mowing neighbors lawns for some extra cash. Although I wasn't exactly th... Continue»
Posted by AllisonCumms 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
  |  29


The Surprise Vacation


"Did you take your vitamin, dear?" Ellen called from the
I rubbed sl**p from my eyes and picked up the pill bottle,
rolling a big tablet into my palm. "My horse pill? I'm doing it
"Have you noticed any difference yet?"
"Nah. Vitamins are pretty much all alike." She'd gone on a
minor health kick a month before, insisting that I needed to lose
a little weight and take better care of myself. I hadn't
actually made it to the gym to work out like she was th... Continue»
Posted by klammer 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
  |  5

Date Night (femdom classic)

DATE NIGHT (femdom classic)
A wife turns her husband into a sissy slut who is f***ed to service other men and women.

Tonight was"Date Night" and as usually was the case, I'd spent
the day in a high state of anticipation. My wife, Chris, and I had
created the "Date Nights" several years ago to merge our divergent
sexual desires into a mutually satisfying relationship.

My sexual tastes ran to the more exotic side of the spectrum bondage,
f***ed oral sex, prolonged sessions, feminization and role
reversal were exciting fantasies for me. Chris playing the
dominant role was a... Continue»
Posted by ssspspb 2 years ago  |  Categories: Fetish, Shemales  |  
  |  10

High School Girls

High School Girls
A Rings of the Oni Story

by Jaana

"Three teenage boys find their simple lives completely overturned, and
their friendship put to the test, when an unexpected find grants them
both nightmare and gift beyond price."

*** WARNING: The following story contains graphic depictions of sex,
female transformation and female arousal. You have been warned! ***

"Accept the things to which fate binds you, and love the people with
whom fate brings you together, but do so with all your heart."
- Marcus Aurelius, 'Meditations'

"For I have been a traveler in a... Continue»
Posted by lana100 1 year ago  |  Categories: Masturbation, Shemales  |  
  |  6

Going swimming with sibling

I am 18, I have a younger sibling who is 2 years younger than me called Emily. Even though she is younger than me and we both come from the same parents, she has a better body than me. She is curvy, taller than me, wider hips, small waist, amazing big round ass and huge tits. I'm a D but she is an E, almost F. She turns me on a lot, I know it's wrong but I get horny thinking of her naked.

We both love our swimming. Even though this is an awkward sport for me as I am tiny and it is hard for me to hide a big 8 inch cock. I usually tuck it between my legs pushing up against my ass, on top I wi... Continue»
Posted by shemalecharlotte 3 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
  |  25

Black Man's White Pussyboy (sissy fucktoy for

Black Man's White Pussyboy

Story from the perspective of a white pussyboy who gets fucked and dominated by a couple of nigger bucks. He also meets another pussyboy but ends up getting fucked by everyone. Good dialog.

I let Jay into the apartment. He was looking for a one bedroom,
furnished place and had called about my ad in the newspaper. I hoped to
rent this place quickly, then I would be full and could devote my time to
some maintenance and repairs rather than showing places. I looked at the
rental application he had filled out just a minute earlier. From the date
... Continue»
Posted by ssspspb 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
  |  34


It started back in my sophomore year of high school. My father
was overseas with his construction firm on a six month build when my aunt
Marie had her accident. My mom wanted to fly up to see her in the hospital,
but it was the middle of the school year, and she didn't want me missing
any classes. That was when a neighbor of ours, and a close friend of my
parents', offered to let me stay with her and her daughter while my mom was
out of town. She promised to feed me, make sure I didn't stay out in the
rain, and make sure I was on the bus every morning. My mom was usually
incredibly pro... Continue»
Posted by klammer 4 months ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  6

My Boss Tricked Me

I work for a cell phone company. Part of my job is to travel to cell phone towers and fix any problems they might have. I enjoy it but am on call most weekends. Now I consider myself a man in public but at home I love dressing up as a slutty tramp. I love the feel of lingerie on my body. I had a few experiences with a man but it was mostly mutual masturbation. My crossdressing is a secret to everyone except the few I have met online.

Most Friday nights me and the coworkers go out drinking. Just a bunch of guys out having a good time. One particular Friday I got really d***k and my superviso... Continue»
Posted by sissysadie 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
  |  10

In Hose and Heels for Daddy

It was shortly after my 14th birthday when I made the decision to seduce my Daddy. I mean, all of my girlfriends were having naked fun with their daddies. I didn't wanna be left out ;-) After all, me and my BFF, Ashley, had been getting naked and having fun with her daddy for 2 whole years now...and with her b*****rs...and with her uncles...and with her cousins...and with her neighbors...and with her...awwww, get the picture ;-)

It was the morning after my first experience with my Daddy. I was camping out in my back yard and had told some guys to come over for backyard blowjobs.... Continue»
Posted by cdsexslut 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
  |  11

Tricked by a shemale

I was out with a couple of guys from work, Brian and Dave, and we were having some drinks at a local bar. I'd never been out with them before, but they invited me and I didn't want to be rude.

While we were having our drinks I had made some negative comments about gay men at one point, you know how it is, right? Just trying to make some conversation, but they hadn't said anything back, negative or positive, but they did exchange a look that I didn't think about until later... much later.

Brian ordered us another round and I excused myself to take a leak. All I remember after that was ... Continue»
Posted by kevinj631 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  13

A Visit to the Doctor

I hadn't been to the doctor in years. But after a minor health scare with a friend, I decided I should go and get myself checked out. I made myself an appointment with a doctor nearby for the following week and waited nervously to go.

I had been born a male, but for years I have been presenting myself as female. I was really passable too, the only problem was my, well, you know. Not many people knew of horrid past, and I wasn't going around screaming it from the mountaintops either.

On the day of my doctor's appointment, I put on pink lace panties that covered most of my ass, a matchin... Continue»
Posted by Bangbangtrain 2 years ago  |  Categories: Lesbian Sex, Shemales  |  
  |  14

Sissy out of control in the toilet

I'd describe as a fit rough looking submissive guy. Recently love to dress in panties and stockings and get interfered with....

One of the first and hottest experiences was in a quiet public toilet. It was about 3.30 on a summer afternoon and I'd had no luck down a nearby cruising area - which was unusual as it was normally reliable. The lack of action was most probably down to feeling slightly inhibited by what I was wearing under my shorts.

As I entered the cottage (as we call public toilets in the uk) and judging by the scurrying that occurred I'd interrupted a scene.

I went in ... Continue»
Posted by skins4skin 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  
  |  26


It was supposed to be the best day of my life...and maybe it was, but
definitely not in the way I planned.

My 21st first day as a man, as a true lord of the
first day as a Master. I was so nervous I threw up my lunch. Not very
manly, I know, but just the thought of having my very own sissy to play
with had me teetering between the giddy excitement of a k** right about to
open the biggest present under the tree, and the stark terror of officially
being a man in my step-father's could I measure up to him? I
felt destined to disappoint him...and I did... Continue»
Posted by klammer 5 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  1

Horse Cock Girl 6

A few days after going to the club with Lucy and Scarlet, Amy was on her lunch break at work, thinking deeply. A lot of things that had happened or been said that night had stuck in her head and it had been bugging her since. Everything she was thinking about was to do with her relationship with Lucy and Scarlet.

She'd been thinking about something since even before the club: marriage. She loved Lucy and believed that Lucy lover her too. She was, however, wondering if, were she to ask Lucy to marry her, Scarlet might get jealous. Amy didn't want that, because both she and Lucy loved Scarl... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
  |  4

The shame of being caught

I have dressed as a girl since I was young boy, I have early memories of my mother having caught me dressed taking me to see a c***d psychologist, I distinctly remember him telling me mother I would grow out of it! Well I never did. However I did have a normal up bringing, got married and carried on dressing throughout my life with increasing secrecy. After a successful career in IT, I was in it at the right time I retired early. Our c***dren have grown up and left home and with my wife and I only in the house life has been quiet. After retirement the opportunities to dress have multiplied co... Continue»
Posted by LaceTops4U 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
  |  5

Baby Sitters Secret

The story that I am about to tell you took place on a day that started out very ordinary, but would end up as the least ordinary day of my life. Until that particular Winter day, I thought I knew who I was. I was Peter Fuller -- respected educator, devoted husband, loving father. I had never cheated on my wife, I had never lied to a friend, and I had certainly never slept with a girl that young before. All of that changed within a matter of hours. But you know what? I wouldn't change what happened for the world.

Years ago, I moved to the small town of Emberton, Rhode Island to take a job ... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
  |  22