Sex Stories - Shemales

A Job In The Theatre

Chapter 20 -- Gary becomes Gayla "Be a dear and get that bag from the car," Paula winked. "Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment, was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so obscene with that erection dominating his leather pants. You could see it a mile away. Gary could never go outside looking like that. Billy could care less. Billy looked Gary in the eye, had that crooked little smile of his. Gary couldn't believe what he had just agreed to...willingly. He had just met this guy, didn't even know him. And yet he had basically promised to do all kinds of things he shouldn't do, horribly embarrassing things, ... Read More»

First black T-girl

I've been wondering what to write about lately. I've received a request to write about me and my sister, but that is a road I might have trouble going down. Today I was thinking about my bi-sexual stripper girlfriend from the past, who loved bringing home other strippers (mostly lesbians) for some hot threesomes. However, today I shall write about my first Transgender experience. I had responded to an ad placed by a self described hot black female that was in the local singles section of a free weekly paper. My thoughts were really "WTF", as I expected no response but became surprised when I received a call back from this girl. We got to talking and getting along really well and over the course of a few days had decided to meet. She described herself as ... Read More»

The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shear red Blouse, and Heels. I decided not to wear nylons so my legs could feel the night air as I drove up the Freeway. When I drive I like making sure my skirt is pulled up to ... Read More»

John D

John was coming to stay in Manchester overnight and had advertised for a submissive girl to meet him at his hotel for the evening. His profile really interested me as it ticked a lot of my boxes. He was assertive, his picture looked good – although I couldn't see his face – and he had a number of positive messages in his guest book that lead me to believe he was reliable and not a timewaster. John was also around 20 years older than me and I am a sucker – literally - for the more mature gentleman. Online we'd discussed our likes and dislikes and decided on a little bit of role play. I was to be a rather slutty girl applying for the job of John's PA. We were meeting for my "interview and assessment". John had even emailed me a formal letter outlining the nature ... Read More»

MY FIRST TIME WITH A SHEMALE

I`ve always had this fantasy about being with a shemale,i guess something about a chick wit a dick and tits always turned me on,i`ve always been curious about wat it`s like to be fucked by one.Well last weekend was a weekend i`m gonna remember for the rest of my life bc that was the weekend i decided to finally fulfill my fantasy and make it into a reality,i only shared this secrect with one friend of mine who is a lesbian and told me she wanted to help my fantasy come true.Jennifer goes to local lesbians clubs and said she met a gorgeous black shemale named Pamella who was looking for fwb only,she said Pamella had told her that she a top and love to fuck men hard in the ass but also liked to get fucked in the ass herself,Jennifer then told Pamella about me and ... Read More»

Issy used by black men

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 has been smiling at me. He said he would like to come down to my room and talk to me but he didn't want anyone to see him come there. I was scared and didn't really know him ... Read More»

My Roommate, Brian

I stood in the middle of my room, frozen in shock and total disarray. On the other side of the doorway stood my roommate Brian, staring at me in disbelief. It wasn't a very confusing situation, and not many excuses I could come up with. I had my boxers around my ankles, and my lotion covered hand wrapped around my dick. Well, not much of my dick was showing. It wasn't exactly a decently sized one, topping out at just under 4 inches. On my computer was a porno starring a very obvious transvestite getting penetrated by a man. I was beet red, naturally, and was almost ready to cry when he suddenly burst out laughing. Not just a few giggles either; he was doubled over laughing till tears came to his eyes. Finally he sobered up enough to collect himself again, and ... Read More»

Sales Training

Gary Michaels had been very successful in heating system sales during his first five years with his company, however the past two years had been very disappointing. So disappointing, in fact, that he had been called on the carpet and told to begin producing or else find another job. Gary really liked his job and felt he had really been working quite hard, but that his "luck" had just not been there. He did all the required prospecting to find out who was thinking about buying a new heating system, but he just couldn't seem to close any sales. "Maybe I'm in the wrong business", he thought, but he knew that he had been successful and wasn't ready to throw in the towel yet. Gary was sometimes too concerned about the sale, and not concerned enough about servicing the ... Read More»

My First Ladyboy

I was working in Bangkok a couple of years ago. As was the normal practice all the guys would finish work on a Friday afternoon and head to the local bar for a couple of beers. This particular Friday we were in the usual place chatting and having a nice relaxing time. When she walked in. Taller than most Thai girls. But stunningly beautiful. Long jet black silky hair. Halfway down her back, big eyes. Small mouth. Full lips. Wow what a beauty. I was watching her walking in. When she looked over at me. And smiled. I thought. ”Kelly. Don’t let this one escape”. So i followed her to the bar. And asked her if i could buy her a drink. Her name was “lea”. Over a couple of drinks she told me she was from a small town north of Bangkok. We stayed in the bar, and ... Read More»

My Story...

Hy my name is Noemi and this is my story... I was nearly five years, my parents sleep and my sister stayed overnight at a girlfriend. I allways looked at her tights, skirts, dresses and shoes admiring (she is six years older)and i was jealous that she could wear such beautiful clothes. I liked to be a boy but i dont like my clothes they were so boring and feel uncomfortable. This morning i absolutely want to know how it feels to wear tights. I remember that my sis had a few colours (red, blue, black, skincoloured) i tried on the red one. This moment change my life completely, it felt soo tailored, slicky, flexible and comfortable that i wont take them off. From this day on i used every unwatched time to wear them, later i wear her slips to and she never find ... Read More»

My aunt Fergie trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7" and 200 lbs she was your stereotypical aunt with some fat and wide hips and big breast. She picked me up at the bus station in her car. She said," My household is different and special I have girls who you will find are very unique. I too am unique and I will show you what I mean when we go home." We rode for a half-hour and we arrived to her big old which I would find was an old Victorian with a widow's roost on top of the roof. She escorted me to the bedroom that would be mine and told me," Put your clothes and things away." I went started hanging up my pants and put my underwear and socks in the top drawer and put the rest of my stuff away. Aunt Fergie poked her head into ... Read More»

Ensnared by a Corset

I had walked past that store every day for the past two years. I had never once failed to look in at the window displays. At first it had been furtive, a look from the side of my eyes keeping my head facing forward. Never pausing and giving no outward sign that I was looking at the lingerie display. I had stumbled on the shop during my first week at the new job. I had left work one lunch time to find somewhere to get a bite to eat. I didn't' know Southampton that well, so I had meandered my way through the city centres streets. I had always had an interest the fairer sexes lingerie and had often bemoaned to myself how unfair life was. Men had what? Boxer shorts, y-fronts! While women? Well they had the choice of panties, boy shorts, thongs, silk, cotton... Do ... Read More»

Ladyboy orgy in Thailand

During one of my many nights in the sleaze capital of the world Pattaya, Thailand I was at a certain ladyboy bar all dressed up in my sexiest outfit that the "girls" had ask me to wear in as I had shown them some pics of me dressed. Not that I could ever hope to compete with any of them! Chatting away with one of the girls a German guy came over to us and said that he having a "party" up stairs and if we would like to join him and his friend. I assumed he just meant the girl from the bar and told them to have fun and she went off with the German guy. Just as they went threw the door leading up stairs the guy turned around and said "aren't you coming too?" I turned to the manager "Bob" just to make sure it was alright and he just gave a grin and a wink. Went ... Read More»

Jobsite Surprise

Owning your own Landscaping business definitely has its advantages. Make your own hours, do the jobs you want, meet interesting people….The last one is the best. The other afternoon I went to deliver an estimate for a large gardening job I had been working on. When I arrived at the house I rang the bell and waited. There were two cars in the driveway but no answer at the door, so I walked around the back to the pool. As I came around the corner to the large hedgerow separating the back yard from the pool I heard two female voices talking and giggling. Passing the hedge, I froze dead in my tracks. My eyes flew open wide and my jaw dropped at what I saw. Beside the pool, the lady of the house was making out with one of the most beautiful women I had ever ... Read More»

Erica Goes to College

Erica goes to a boy's college... I was in transformation there was no doubt about it. I had all but given up on appearing as a boy; it wasn't who I was as a person. As a boy I thought I was doomed but as a girl, I felt happy and found peace of mind. I did my best to conceal my changing appearance but it was impossible to hide my face where change was most evident. Some of the boys hated me for being different. Apparently they felt justified in kicking me when there was no one to observe their hatred. I guess what we don't know or can't understand is threatening to some of us. Fortunately, I was able to establish camaraderie with some. Most of them were the virile and stronger boys with healthy libidos; many of which were on the football team. If a ... Read More»