Shemales Porn Stories
Page 66

Bondaged and fucked at a hospital: Pt 2

I ate my lunch watching tv, when I was done Lisa cleaned up after me and she gave me some time to rest as she left the room, sort of like "nap time" at a daycare. I was about to drift off when I felt a sudden strong urge to pee but as I moved my legs around in the bed to get up I was instantly reminded of the thick crinkly diaper I had on under my hospital gown. I thought about what the nurse said, about having to use diapers for a whole week and I didn't want to disobey her orders seeing as she really knows how to discipline a "naughty diaper boy" which is what she referred to me as. I also d... Continue»
Posted by adblman 2 months ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 1495  |  
100%

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 4 years ago  |  Categories: BDSM, Masturbation, Shemales  |  Views: 1489  |  
84%
  |  1

"DP by two BBC Transsexuals"

I met Layla through a local phoenix dating ad,we first called each other a few times trying to get to know each other,Layla was a beautiful black transsexual,her picture on her ad caught my attention,her beauty and the thought that she was a tranny really had me wanting her so bad,I told her about my fantasy of being fucked by a tranny,I had this fantasy for years,she then said she would love to make my fantasy become a reality,she asked me if I ever been fucked before I said no but I have fingered my ass before,then she said bet you`re tight can you handle 10 1/2" of she-meat,I said idk but ... Continue»
Posted by beaverchaser 1 year ago  |  Categories: Anal, First Time, Shemales  |  Views: 1491  |  
100%
  |  4

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 3 years ago  |  Categories: Gay Male, Shemales  |  Views: 1488  |  
97%
  |  12

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 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1486  |  
98%
  |  5

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 1 year ago  |  Categories: Shemales  |  Views: 1486  |  
100%
  |  3

Drink Me (Sissy Story) by sdvine

With my chin resting on the table, I stared at the little bottle. It was a rather unremarkable looking thing. It could almost be called a vial, but I think of vials as something smaller and thinner, like in a lab. This was more like one of those small energy drink containers, only bigger and made of glass. The liquid inside, however, was much more remarkable. Silvery, with tinges of blue, it appeared to shimmer. Almost as if it were alive and breathing, the shimmer was like a pulse. I found it very easy to stare at it, it was quite hypnotic. Like it was calling to me, enticing me to drink. I h... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 1487  |  
100%
  |  3

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 1 year ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 1482  |  
100%
  |  1

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 3 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1477  |  
97%
  |  6

Crossdressing and a Stranger's Cock

Friday was my first time I was fucked by someone other than my owner. I have blown a friend of my owner when fully dressed, but Friday we had to travel during the afternoon, so I didn't fully dress but changed into stockings, bra & forms, thong and had a sheer long-sleeve turtleneck and tight skirt when I got to the apartment.

Nick is a friend of my master. He is shorter, maybe early 50s, with a nice very hairy cock about 7" and a bit thick. He smelt like cigarettes and had worked earlier so his cock and ass smelled sweaty. Though I don't smoke it was a turn on because it was a bit disg... Continue»
Posted by cd_joyce 25 days ago  |  Categories: First Time, Shemales  |  Views: 1477  |  
100%
  |  2

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 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1477  |  
100%
  |  2

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 1 year ago  |  Categories: Hardcore, Shemales  |  Views: 1475  |  
86%
  |  2

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 4 years ago  |  Categories: Shemales  |  Views: 1472  |  
98%
  |  6

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 3 years ago  |  Categories: First Time, Shemales  |  Views: 1477  |  
99%
  |  7

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 2 years ago  |  Categories: Shemales  |  Views: 1469  |  
67%
  |  2

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 9 months ago  |  Categories: Hardcore, Shemales  |  Views: 1467  |  
62%
  |  1

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 4 years ago  |  Categories: Shemales  |  Views: 1460  |  
89%

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 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1460  |  
100%
  |  5

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 2 years ago  |  Categories: Hardcore, Shemales, Taboo  |  Views: 1459  |  
100%
  |  6

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 1 year ago  |  Categories: Gay Male, Masturbation, Shemales  |  Views: 1458  |  
100%
  |  3