Shemales Porn Stories
Page 77

Job Interview

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Keliana Kotey, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company’s receptionist, Paula, put her head around the office door to tell me that Miss Kotey was waiting and asked if she should show her in. I agreed and sat back to watch the view of Paula’s nice arse as she walked away from me. A twenty two year old gorgeous blonde, Paula was the kind of person who brighten... Continue»
Posted by keliana 4 years ago  |  Categories: Shemales  |  
  |  22

A busy Friday night. [CD/Gloryhole/neighbor]

I had been looking forward to this weekend for a month. My wife was going to visit some friends in NYC, and I was staying home, by myself. Yup, just me and all of my favorite things, like stockings and panties, and sexy little outfits. The torture was finally over, and the Friday she was to leave, arrived. I was still at work when she called me to tell me she was on her way up rt. 95. I wished her safe travels, and told her I would talk to her tomorrow.

I immediately left work, and headed for my car. I was so excited that I practically ran out of the office. I was going to indulg... Continue»
Posted by pbg732 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  23

How I Became Vanessa Chapter 3

Hello dear readers,

I strongly encourage you to read the previous two chapters of this story to fully grasp the sudden changes which affected my life.


At home, Elena was waiting for me but she wasn't alone, her boyfriend was there too. He was a tall black guy named Jeff. I told them all the things that happened at July's, blushing as Jeff was watching me with desire.

Elena hadn't changed her sexy outfit and her beautiful face leaned towards Jeff's crotch uncovering his 10 inch cock which was even thicker than John's. She started to suck it hungrily, encouraging me to join her whi... Continue»
Posted by slutyvanessa 3 years ago  |  Categories: Shemales  |  
  |  19

His teacher, The transsexual

A really nice story from another web page! Enjoy

Greg was late for class. He ran through the hallways. They were very particular about being punctual here. His health teacher especially. She was very focused on such things. Greg had been late twice this week. He couldn't help that his car kept breaking down. Ms. Sin was a real hardass and didn't accept excuses.

Greg had only started his last year of high school here after his eighteenth birthday a few months ago. He was worried about the impressions he was making. He got to the door of his health class and checked his watch apprehensive... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  
  |  6

Why I miss my ex

Why I Miss My Ex
I feel obligated to say that I am not a passable crossdresser, not even close. Even without my beard, I’m very masculine, large framed, and I have a very deep voice. All of these things aside, I love to dress up in sexy lingerie, panties, dresses, bras etc. While I’m dressed, I love to be verbally humiliated, although, I don’t think being called names like “sissy” or “fag” or “cuckold” is actually humiliating. For me, it’s a huge turn on, and I love to think about sucking cock while I’m being humiliated.
It’s quite a long story about how I got my ex-wife to play with ... Continue»
Posted by pbg732 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  11

A Halloween Hoodie story

*crossdress story*
This is the story of my first time going out dressed; it was halloween last year (2009). I figured i'd have less to worry about walking around dressed in a gothic tartan corset, spider-web mini-skirt, fencenet tights and about 10 armbands and bangles. It wasn't exactly brilliant but it was the excitement that spurred me on.

Of course i was scared of seeing someone i knew, like a neighbour or a friend, but it was about 22:00ish, so i figured it was dark enough and late enough to avoid those kinds of people.

It was a lovely feeling as i stepped outside, the wind rushing... Continue»
Posted by KitsuneTV 5 years ago  |  Categories: Shemales  |  
  |  16

Used Like A BBC Whore

About a year ago while living in a hotel and living there as a Transexual I was used by a young black man as his whore for the night.

He moved in about two weeks ago with a couple friends. They where maybe 5 rooms away from me on 1st floor. As the week wore on I would be coimg and going and would notice them watching me. When I would walk by they never said anything but one of the guys always smiled at me.

While one night I got a phone call and he said his name was Rick and he lived down the hall from me. He told me what he looked like and then I realized it was the young black guy that... Continue»
Posted by sissy_gurl 3 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
  |  14

roadside ass-istance...part 1

as i was driving home, thinking about malcolm, i saw a car on the side of the road, ahead of me. as i got closer, i saw a very cute black woman standing by the side of the road, looking very irritated. i slowed down & pulled off the road behind her car, then got out & asked her if i could help. she asked if i could give her a ride, because she couldn't get a tow truck 2 come out 4 at least an hour. i told her 2 hop in & she gave me her home address, saying that she would just call the towing company when she got there. as we cruised along & chatted, she told me that her name was angela & that... Continue»
Posted by tight_virginal_ass 4 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
  |  6

banged in panties

The day was 10/4/2012 and normally I only wear panties inside never on the outside, but I was feeling kinda kinky. So after doing my running around I decided to stop at a local adult porn store with the booths and private rooms. At the same time I was texting with a friend from here thats crazy about me in my panties. I told him that I was wearing my panties being that I thought we were gonna hook up, but due to scheduling we weren't able to, so he asked me to take a pic with my phone and send it to him, now I wasn't home so I didn't think that i would be able to pull it off, suddenly this nic... Continue»
Posted by frkinatl 3 years ago  |  Categories: Shemales  |  
  |  11

The Making of A Sissy-Part One

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father. Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind. Jane’s girls took special delight in dressing their sissy b*****r and loved to take him out to the mall and such places, dressed in pink frilly skirts, where he learned to be humiliated. He was shown to the packs of small... Continue»
Posted by midsummerman 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
  |  5

First Public Experience

From my previous stories you’ll know I love to dress up in lingerie. After a small number of sexual encounters with men I decided it was time to take things to the next level. I told a lesbian friend of my cross-dressing and asked her to take me to a gay nightclub dressed as lady. I didn’t want to go on my own. She seemed surprised but agreed. All week I wondered what to wear. By Friday I settled on a skin tight white dress with matching high-heel shoes. I spent the previous evening waxing and plunking my eye brows. I wanted to be as feminine as possible. Friday evening i began to get ready. I... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
  |  10

Delilah and the Deep Blue Sea. (Part Two)

When I awoke the next morning I was alone. I rose up from my bed amidst the ruins of the villa and peered around cautiously. There was no sign of her. Carefully I tip-toed out from the ruins and conducted a quick scan of the surroundings. The little olive grove was quite deserted other than the small creatures with which I shared the island. These seemed busy at this early hour. There was a little dark grey bird singing from the scrub at the edge of the olive grove. It had a musical voice I found quite soothing. I was to become familiar with that little bird and the mate he found to build ... Continue»
Posted by Mikebasil 3 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  
  |  15

The wonderful feeling of a sissy penetration by yo

Nothing like that initial penetration is soo wonderful however there is so much more for me. just knowing that i intend to give myself to him submitting to his Big Hard Man Cock is a turn on. He wants me ready for him so he can show me his love and make me his girl.

The act of preparation, the douching and initial lubing, knowing I'm going be taking a real man cock inside me builds on the sexual emotion and makes me feel so submissive and feminine.

laying there in my nighty and panties and assuming the position he desires, normally face down, pussy up, legs together, wiggling my botto... Continue»
Posted by sissygirl 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  17

Becoming Aphrodite Ch 01

My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettable and even the famous porn star I mentioned could not compete with her.

We got married very young and we were very happy for many years but Jennifer was slowly changing, discovering parts of her which could not be ignored any more. In fact, she did not have enough sexual experience before getting marr... Continue»
Posted by slutyvanessa 3 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
  |  6

Being a shemale's toy can be fun

Joliet called and asked if I would be interested in having some fun...I thought about the last time and how pissed off she got. I hesitated long enough for Joliet to whimper in the phone 'I promise to make up for my last theatrics, no bondage and I will reward you very handsomely if you attend to my needs this week end.'

Sensing desperation, I gave my demands 'reward me up front in large bills in an envelop that I will address and drop into the post office before we do any thing, you will give me your car keys before we enter any building, and I have the last word as to what I will and ... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
  |  2

The Developing of Emma Part Four

Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. Elaine was right, Emma was beginning to enjoy the plug and as she tried to rub her confined cock, she imagined the plug to be Kurt’s cock; how she wanted to cum! The blue pill she had been given would keep her little cock hard in the cage and make her yearn to orgasm. This would make her extra obedient a... Continue»
Posted by midsummerman 3 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  3

Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
  |  21

My highschool girlfriend 2

It had been a week and me and my girlfriend had not done anything else, but ofcourse we talked about it. Her mostly, saying "I was so sure you were so strait, im so happy your okay with my cock" all I would say was "I was so sure I was strait too, but being with you, just changed that I guess but I love it, you make me hornier than a girl with a vagina ever could." She also brought up another point, that the anal can go both ways, and ask if she could be on top next time. I was kinda scared it would hurt, but thought it may be fun, and told her that and she said she would make it painless, by ... Continue»
Posted by suckmedry69 4 years ago  |  Categories: Anal, First Time, Shemales  |  
  |  7

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 2 years ago  |  Categories: Mature, Shemales  |  
  |  5

Dirty Tranny gang bang

Deep breath Charlotte, step into the night air and strut your stuff girl.

This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glitter in the light reflected from the street lamps.

It is not quite 8 pm as I walk the short distance from my hotel to the pre-arranged meeting place just outside the pub near Tower Bridge.

Two men walk past; mid thirties and well dressed, they have both been looking at me for some time,... Continue»
Posted by charlottekerscot 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  
  |  8