Shemales Porn Stories
Page 82

Submissive Sissy Jenny's First Cock

Submissive sissy Jennifer's first cock

There is a shy knock on your door. You open it, wondering who it can be. A stranger hands you the end of a dog chain, you can see that it leads to a red strap round his neck.
"I'm Jennifer, Sir" he whispers, softly & huskily. It becomes clear now - you remember the conversation on the web a few days ago. Not saying a word, you pull the stranger into your room with the lead, shutting & locking the door behind him. You slip the end of the dog chain over a coat hook behind the door. "STRIP" you command.

Jennifer slips off her coat - it was a co... Continue»
Posted by sissy_jenny 6 months ago  |  Categories: BDSM, First Time, Shemales  |  
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Cum drenched afternoon

I was anticipating Marla's return from her work related trip out of town for a week. She was due to arrive around four in the afternoon. I wanted to make sure I was ready, so I spent the day preparing myself. I took a long hot bubble bath and made sure I was completely shaved. I sprayed on body spray and applied my make up and fixed my hair. Next I picked out my outfit, tonight would be my catholic school girl uniform. It starts with my white satin crochless panties with rows of little pink ruffles on the back. Marla always likes it when we have our love sessions in panties, and the cro... Continue»
Posted by slipn2panties 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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White BBW getting some young Black dick

During my senior year in high school our football team
Enjoyed one of the best seasons in school history.
The coaches had it set up to the point where
Most players did not have to take tough courses
So no star player grades would be affected. My trigonometry teacher
Mrs. Blake hated football with a passion. She told the coaches
That I had to adhere to all the guidelines that non-athlete students
Had to follow by. I will admit that math was my worst subject. I was busting
My butt studying and I still could not pass those grueling examines.

Around the mid-season I was on the brink of... Continue»
Posted by kinghut 2 years ago  |  Categories: Hardcore, Shemales  |  
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Gender bent – a Mistake

Gender bent – a Mistake

I was dressed like a bimbo, my lips plumped up from sucking on shot glasses, Pink latex, Trashy fake tattoos of my back saying fill me and a black ace of spade on my ass cheek and Sissy clit on my pelvic area near my dick, My tits was pierced for this party and I had a Cumslut collar on my neck. 8 Inch thigh high pink latex and anime pink wig to make me look like a candy slut. It was either this or complete shaming of me to the point where my life was ruined. All I needed to do was be dressed like this and serve drinks and I just served my last one after Kandi took i... Continue»
Posted by youngprboi 6 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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womanly experience 4 - first fully naked punishmen

In high school I wore schoolgirl and similar skirts every single day. On my legs I always had either tights, knee- or thigh-high socks, or nothing (when it was hot). I almost never were thongs to school because I couldn't risk for someone to find out that I'm on hormone therapy.

My father was buying me all the clothes so I had to be careful with them because he needed the slightest excuse to punish me. The boys were going crazy for me but I never allowed them to touch me. On the last year of high school I did allow some breast touching but that was all. One day one of the buys couldn't bear... Continue»
Posted by p1llow 5 years ago  |  Categories: BDSM, Masturbation, Shemales  |  
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Ass Training Fun!

Some year ago I was doing a lot of cross-dressing, I had all the gear. I slowly collected everything - buying it all over the internet. I had some lovely dresses, glorious underwear, stockings, wigs, shoes and a big pile of make-up. I was feeling like such a girl and the yearning for cock was getting very strong. I was so hungry for it, wanting to suck a nice big meaty cock, but most of all wanting to fuck one - yeah well up for it. The idea of being shafted by a nice big joyous cock was so strong for me.

With this in mind, I bought a dildo with the intention of training my ass. My thoughts... Continue»
Posted by shetrannylover 4 years ago  |  Categories: Gay Male, Shemales  |  
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SHEMALE SEX IS THE BEST

I had been in sex with gays for 1 year, but had always been intrigued by those hot looking chicks who packed more than a pussy between their legs. I had no idea where to find one in Kanpur

I was definitely bi-sexual, still seeing whores, and still going to gloryholes for my cocksucking needs. I was a dream come true for me, I found a beautiful girl to have some really hot sex with.

For a total slut like her, it was like dying and going to heaven. On my way into the street one afternoon, I saw a beautiful girl standing at road side. I found myself alone at the road surrounded by a bevy of... Continue»
Posted by fukkerguy 2 years ago  |  Categories: Shemales  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 3 years ago  |  Categories: Mature, Shemales  |  
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Natalie strikes again!

I was out running some errands on this sunny Southern California Saturday afternoon when Natalie called me. It was great to hear from her since I hadn’t seen her in a few weeks. She asked if I was busy this weekend and even though I had plans, I told her that I was free. I’d basically drop anything I was doing if it meant spending time with her.

If you haven’t read an of my other stories, Natalie was my carpool buddy, then my lover, and now we’re just in kind of a friends with benefits situation. I still say she’s my perfect lover but there’s no way it was going to become a fu... Continue»
Posted by ocmike 2 years ago  |  Categories: Gay Male, Shemales, Taboo  |  
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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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Last weekend

I had arranged a meeting with a new gentleman lover.

I was excited about being naughty.

Knowing I was going to fulfill my craving with a big new cock to play with made me bulge in my panties as I drove to his place.

I arrived at my new friends place a little early.

He answered the door in a dark Tshirt and jeans that hugged him in all the right places.

There was a little chit chat, but we both knew what we wanted. He wanted to fuck me and I wanted to feel a hard cock fill me with cum.so why delay the fun!

After kissing me, his hands found my tits and pinched my nipples. ... Continue»
Posted by lornasababe69 6 months ago  |  Categories: Anal, Mature, 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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Shemale fun

Recently I've been chatting with a very feminine and beautiful shemale named Lisa.

We've been trading photos and dirty talk over chat lines and emails. I've always fanatsized about a cick with a dick and unexpectedly the opportunity came that we could potentially meet. Being married I had to concoct and excuse as to why I had to go to (city name withheld) and my wife didn't see any reason not to bnelieve me. My wife knows that I love porn, but I've never expressed to her that cock also turns me on - especially shemale cock. Somethings are better left secret.

I arrived at the hotel th... Continue»
Posted by seizetheday 4 years ago  |  Categories: First Time, Shemales  |  
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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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Gloryhole Gurl Part 1

Making of a Gloryhole Gurl! Part 1
By Kristy

Just Like in any marriage after fifteen years ours was getting pretty routine. Every three months I could have sex, in the missionary position, with her wearing flannel Pj’s. Even in the summer she would wear long pants type pajamas and when I would buy her something sexy she would just say it’s not my type and never even try it on! It was only six months after our marriage that she told me she doesn’t like to have oral sex!
Well like any red-bl**ded male I started hitting to gentleman’s clubs around town. The sight of t... Continue»
Posted by kristygurl 5 years ago  |  Categories: Shemales  |  
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Fresh Pussy and a Shemale cock!

We all meet people who turn us on, and make our cocks hard or pussies wet, and i was lucky enough to meet a hot straight girl at a party awhile ago. we really hit it off, and i asked her if she wanted sex, and she said yes, but only a hard cock... I had to tell her that i was a shemale with a 7 inch thick cock and would love to fuck her and eat her sweet pussy. She did not seem shocked, but said show me, so we went upstairs to the host's bedroom, and i pulled out my cock and bam, she did not waste any time, getting on her knees and began to suck my cock. I quickly got naked as did she, she had... Continue»
Posted by cumsquirter 5 years ago  |  Categories: Shemales  |  
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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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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 5 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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