Shemales Porn Stories
Page 82

xdressing school fucked by black teacher

This is a kinky sexual fantasy about my university teacher .Well it all started the first day my new teacher walked in the door .Six foot, very good looking black man .He was 15 years older than me very smooth with the girls.I just turned 21 and am three years into my transformation from male to female i have DD cup boobs. After 2 months of fantasizing and flirting with him i decided to make my move i needed that black cock inside me .I decided to wear the sluttiest school uniform i had it was short tight barely covered my boobs and i wore a killa pair of platform heels .Boy did i look like a ... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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3 Sissies at Lake House have Fun

It has been almost a year and a half since Steve, Mike and Joe have been meeting at Joe's secluded lake house every month. Of course, it's really a secret meeting of three sissy cross dressers who love to dress femmie and let go and have slutty girlly hot sex. ... Continue»
Posted by Sissybra 1 year ago  |  Categories: Hardcore, Shemales  |  
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Cheri

My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 12 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right,
to me I guess. It's been a long road but I'm so much happier now.

The first time anyone ever found out I had a dick after that was about 10 years ago. I went to a new doctor for some ant... Continue»
Posted by LadyShi 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Becoming Emily - Part VI

I was awoken the next morning by an annoyingly high pitched beeping sound. My first instinct was to reach over and slap the alarm clock but when I did the beeping tone didn’t cease. After a quick peek out of my window I saw that a moving truck was backing up to the Davis house next door. It had been empty for the last 6 months and I had mixed feelings about the idea of having a new neighbor. In a huff I collapsed back into bed but not 5 minutes passed when my phone rang.

“Hello?” my one was a mixture of sl**piness and annoyance.

“Emily? Hey It’s Lilly. Did I wake you?” hearing her voice ... Continue»
Posted by taboo_daddy 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Jesse's Dream Job

Jesse sat nervously in the waiting room of the opulent office. He was there for a job interview as a personal assistant. Now at six foot tall with 220 lbs of football hardened muscle he did not fit the description of a personal assistant, but the advertisement on line had been pretty specific about the qualifications for the position and they were looking for a guy with his build. It was even listed first in the qualifications and typing was considered a ‘bonus’ ability. Go figure.

When he had arrived the receptionist called his potential employer on the phone and told him that Ms. Angel w... Continue»
Posted by SCARFACE12 4 years ago  |  Categories: Shemales  |  
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My first and only..

I contacted her on a chat line, we arranged to meet she was working as a nurse in london and was from the Philipines. I met her at her flat rang the bell she opened the door wearing a red dressing gown, I could see the cuves of her body and her beautiful cleavage was showing. She had long black hair brown eyes and was stunning, she invited me in and asked me if i thought she was pretty, I said i think you are beautiful she drooped her dressing gown to the floor and was just wearing stockings. Her lovely tgirl cock hard as anything was staring at me, my dreams had come true. She whent to the ki... Continue»
Posted by yesyesyesplease 3 years ago  |  Categories: Shemales  |  
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Old Black Carl (part 4)

Old Black Carl (Part 4)

There was no getting around it, now. Carl had total control over me with those photos, and I knew it. So many things could go wrong. Carl told me to clean the house before the football game started. He sat in his recliner and watched as I performed chores. It was hard to concentrate because, not only was I scared about the pictures, but Carl’s enormous cum load kept dribbling down my leg. It felt like there must have been a quart in there. After I had finished, Carl told me to shower, and to work on my makeup. He said it was going to be VERY important that I did it w... Continue»
Posted by cocksucker4bbc 2 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Michael's Prom Night (A Chrissie Conway Story

Micheal’s Prom Night (A Chrissie Conway Story)


Kelly and I are home for a few days and were staying at Kellys' mom’s house as usual. All week long all her b*****r Michael can ramble
on and on about is the senior prom coming up this Friday night. He and
Two of his buddies decided to pool their money and talked Kelly into renting them a Cadillac for prom.
When any two of them are together all then talk about is how they are
finally going to laid on Friday. They been waiting the entire school year for prom weekend because the popular myth is that even girls who don’t “... Continue»
Posted by chrissieCD 3 years ago  |  Categories: First Time, Shemales  |  
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Never Wanted To Be Your Girlfriend Ch. 04

8:20am Monday Morning

---------------------------------

"...You can't be serious, Mike. There is no way anyone is gonna believe me," I whispered intensely.

I was sitting in the school office dressed in the patently ridiculous outfit Michael had picked out for me that morning, waiting to see the principal over my "disruptive" behavior. I just glared open-mouthed at Mike as he patted me on the head and smiled.

"It's gonna work great, Andi. Just trust me," he said, and then walked out of the office.

I watched him walk down the hall back to class, and it was then that I saw my mothe... Continue»
Posted by sparkyking 1 year ago  |  Categories: Shemales, Taboo  |  
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Mysterious Feminisation

After a few months of my ‘relationship’ with Stefan I realised that I had irreversibly crossed over the border between being a straight guy who liked to experiment with cross-dressing into being… well, something else. I am not sure exactly when this realisation hit me. Was it when I was pulling on a pair of tight girly jeans that I would pair with high stilettos and found I was not thinking how I might look in the mirror and how the clothes felt to me, but how sexy my ass would look to him? Or was it when in my day job I could still feel his cum still swimming around in my stomach from the nig... Continue»
Posted by tricked-sissy 5 months ago  |  Categories: Shemales  |  
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my first tranny pt. 2

it hurt so bad but felt so damn good. I told her just to stay still so I can get use to it. get use to having a cock in my ass. that was a totally new feeling. it was something I always wanted to try. now I was.

she slowly started to move back & forth. not really pulling out, just enough to make me feel better about it. she was stroking my cock, which was rock hard. I could feel her balls on my ass. deep down i was freaking out. this is really happening. I knew that coming here I was going to fuck some ass. not get my ass fucked.

eventually, I got use to her cock in my ass & she was pu... Continue»
Posted by radec_24 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Emma's sissy fantasy

sissyqueerpooh, 36
United States
1 minute ago
slave4fetishgoddess
I hope you like this....

I like both men and women, I love a woman's beauty and grace and love to worship them, but I need cock the bigger the better, I be been fucked in the ass before but have never had anyone cum inside of me, which I would just love!

My biggest fantasy that I have is for me to be a live in sissy slave for a dominant married couple. They would pick my up at a bar, d**g me and take me home, when I wake up I find that I am tied up in a dungeon naked and all of my body hair has been removed. I don't kn... Continue»
Posted by slave4fetishgoddess 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Episode 16 - Becki in Chains

Crowded pub in Newcastle
A couple sat at table in the pub, when 2 gorgeous chicks walk in, stand hips touching at bar. Man cannot keep his eyes off their long legs and tight denim-clad bums, wife notices his gaze. "Stop drooling, they're much too young for you... wait a minute isn't that blonde Becki from your favourite porn site?
"How did you ...?"
"Easy, just click on your Most Visited page on Chrome; you really should be more careful on the Junior Porn Club site " she said raising her voice slightly.
Becki and Molly's ears pricked up, giggled and brought their drinks over.
"Can ... Continue»
Posted by dasx 5 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Sweet transvestite

Sweet transvestites from transexual transilvania.......sweet transvestites..... I don't know about you but I love Rocky horror picture show and in particular I really love that song, why you ask? well for starters it has to do with the fact that I myself am a transvestite a crossdresser if you will and yes I am still one even though I have not dressed in a couple of years, see the thing about being a TV/CD is that you will always be a TV/CD. No matter how straight you try to act, how many times you purge that feeling will never go away and it will creep up on you again and again, and this is b... Continue»
Posted by alex_boycd 2 years ago  |  Categories: Gay Male, Masturbation, Shemales  |  
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mommy's wanna be girl

"Hi honey, how was your day?" My mom called out her usual question as I came in through the side door, and tried to quit sniffling. In vain -- I still had the hiccups from my recent crying jag, and my nose was running. I'm sure my face was red too.

"F-fine," I hiccuped. Obviously, it hadn't been fine.

"Oh, hon, did those boys tease you again? They're so rude."

"Why do they keep calling me a girl, mom? It's so mean! Just 'cause I don't play sports..."

In truth, it was more than that -- I just didn't want to admit it to myself.

My name's Jake. I'm 18, but you wouldn't think it -- ... Continue»
Posted by nicoleinberlin 3 years ago  |  Categories: Fetish, Mature, Shemales  |  
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Trapped and Trained Sissy Ch. 04

Trapped and Trained Ch. 04
I don't exactly remember at what point it started, but I remember being so ashamed and humiliated by it even happening. The redness in my face seared, but you still couldn't even tell due to all of the makeup that was caked on me. And there it was again... so involuntary, so humiliating...

There I was sitting on this chair from hell with a cock thrusting in and out of my painted lips, another devil of a machine tearing my ass... pussy... in two underneath me. And I was moaning.

It wasn't one of those painful moans either... it was a moan I'd often heard coming... Continue»
Posted by hpm12 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Lilith RIDes Again

THe following event happend the night i took my profile pictures.......

I had almost given up all hope of finding a man online in time before my girlfriend and k** came home the next day. Finally at 4am a reply, his name was Todd. HE was on his way, one hour later he arrived. I got really dolled up for him this time; makeup, my favorite pink mini skirt and thigh highs on my smooth legs. When i let him in and disrobed he smiled and said "YOu are beautiful arent you?" I blushed a little as we sat down next to each other. HE put his hand on my thigh and i looked at him " DO yo... Continue»
Posted by witdacandy09 5 years ago  |  Categories: Shemales  |  
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A Savannah night

Crossdressed fully and very seductively in only fishnet thigh highs; hooker heels, g-string, garter belt, and bra, (all black), I had intentionally let the man walking around the motel parking lot see me. He'd stopped in his tracks, mouth open, and stared, as I stepped out onto my motel room balcony. I pretended to not notice him while giving him a really good look at my ass as I turned and went back into my room. A few minutes later he was back out in the parking lot again, pretending to be busy in the trunk of his car while glancing up toward my room. I knew I had me an interested voyeu... Continue»
Posted by dana213 5 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Delilah and the Deep Blue Sea. (part four)



The skipper of my boat was a man of few words it seemed for he maintained a taciturn silence as we sailed away from the island. I didn’t mind the lack of communication. I huddled miserably in the stern of the fishing boat, lost in my own thoughts and hardly in a mood to talk. My tear blurred eyes were fixed upon the dwindling view of the island as we left it far astern. Soon it was nothing but a pinprick on the horizon and shortly afterwards I lost it in the afternoon haze. It felt as if something had been torn from my soul.
I blinked away my tears and glanced ahead. A sliver of land had ... Continue»
Posted by Mikebasil 4 years ago  |  Categories: Shemales  |  
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Idle Hands

Idle Hands

They say that idle hands are the devil's playground. I know now that that
is true. My wife and I have been married for ten years. We are both
successful in our careers and decided not to have c***dren. We fell into
what can only be called a "funk". We both would arrive home at six
o'clock, eat dinner and spend the night staring at the television until
eleven, fall asl**p and get up the next morning and repeat. My wife had
remained thin and sexy, with an incredible ass and a pair of firm breasts
that would rival ... Continue»
Posted by brandiboots 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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