Sex Stories - Shemale - PAGE 7

Reversal

His business trip was over and he was about to be in bed with his wife for the first time in a week. Her trip to the diet clinic had also kept her out of touch as well. They both wanted this but, as he was about to find out, for different reasons. She was waiting for him in the bedroom, already under the covers. He could not see what she was hiding but he knew she only did that when she had a surprise for him. He did, however, see what she had put out for him to wear. "I know how you like to wear the nightie and panties sometimes, so I put some out for you. They're your favourite, aren't they? I really want you to wear them for me tonight." She normally did not insist like this but he did not want to waste the opportunity or spoil the moment. What ... Read More»

My First Time as a Girl

I was hoping to hook up with a straight guy. I have 2 b*****rs and a s****r I’m the youngest and a Freshman in high school. Always been fem preferred to play with my s****r and her dolls. My dad is an ex-marine. Tough guy. My b*****rs are following in dad’s footsteps, military orientated. I‘m a big disappointment. My dad accepts me for what I am now. My mom always stands up for me when my dad criticizes me for acting like a girl. My b*****rs look on me more as a s****r than a b*****r. Weird as it sounds I am more fem in a way than my s****r. I like to dress up in my s****r’s clothes and wear make up. I have long blonde hair and green eyes. 5’6”, 126 lbs, skinny. I’m the smallest in height and weigh less than any of my siblings. I have always dressed up ... Read More»

First time with CD when I wanted tranny

(True story)I got in touch with an asian tranny online (as most people do lol). I've always had an attraction towards trannys, especially really sexy black ones which appear in porn but i've never fulfilled my fascination. I'm straight and have slept with the sexiest women going but have a curious side. Anyways back to the tranny, I was a bit in doubt whether it was a real tranny I was emailing so I gave her a call, the voice on the other side was a definite female tranny. I found her voice sexy and had an asian accent to it. We agreed to meet up in a few days and as everyday went by I became more excited. The day to meet up I made my way to her place which was a bus and train journey away. I got to her door, she buzzed me in, dick in my boxers rock hard, i'm ... Read More»

A Lady Indeed

"Blue-eyed boys are always getting me into trouble," she said in a sultry voice. I smiled, as I looked into those warm brown Latina eyes, so soft yet full of mischief. "I'll be back in a sec guys," said Tracy as she got up from the table and headed towards the ladies room. "Jack," said Mike, the cook I was relieving, "you need to be careful with Tracy, her name used to be Tommy." "I know Mike," I replied, "we met last night." Yes, that was when I met Tracy. I had worked the evening shift at the truck stop and as I walked home through the park, I overheard an argument coming from a wooded area. I decided to investigate and soon saw a big guy standing over a woman that was trying to get up off the ground. "I'm gonna mess you up bad you faggy bitch," he roared ... Read More»

Epiphany

My girlfriend Tonya was out of town for the weekend. She was meeting some college friends and going shopping and carousing in the city. A typical girls' weekend. I kissed her good bye at about 4:30 pm on Friday. We had become pretty close in the year that we had been dating. She was a cute blonde with the lithe athletic build I loved so much. We also got along so well. We were like drinking pals that enjoyed sex together. I knew that I was lucky to have her. Yet as close as we had become I couldn't bring myself to tell her my biggest secret. Whenever my girlfriend was out of town for any length of time I engaged in my favorite pastime. I was addicted to dressing as a woman. I would even be so bold as to take drives around town dressed up. I know I have one ... Read More»

Crossdressers first time with a guy

Hi, im new to this. this happened about 3 years ago now. I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser. I thought enough was enough and started making my way onto the street looking for - well I don't know what really. but I just walked until I saw a dark looking guy having a piss in a courtyard not far from where I was. I mad my way over to him shyly and was trying too look over his ... Read More»

A surprise for John

It was a busy day at work when I got a text message from John asking what I was doing that night. I replied that I had no plans. He told me he was leaving work early, if I wanted to stop by for a lil bit I was more than welcome. I told him I would. I did want to talk to him about a small trip I was planning. I got to John's by 5:15 and took a quick shower to freshen up. Quickly put on thigh highs, short skirt and blouse, a touch of make-up and a wig. When I entered John was on the couch watching TV. I cuddled up next to him, gave him a nice long kiss and said hello. We chatted a lil bit when he mentioned the new lingerie catalog on the coffee table. He told me since I've lost a good amount of weight that I might need to get some new lingerie. I was happy he ... Read More»

A Night i will Remember 4 Ever

About six months ago I went to a transvestite bar and dance club in the centre of the city where I live. I was dressed in my sexiest all-leather shift minidress, sheer stockings and 4-inch stilettos, and my favourite blonde wig. I was fully made up with long false eyelashes and blue shadow, painted nails, and dark purple lipstick, and my most valuable gold necklace and large chunky earrings. Though I say it myself, I looked beautiful. I have a very good figure – I need to, in my line of work – and long shapely legs. I knew as I walked across the dance floor that I was drawing admiring glances from all the men and from the other ‘girls’; but there was only one that I had eyes for. I had seen her on the way in, and she was absolutely gorgeous. She had on a ... Read More»

Visiting shemale goddesses

Sexy hung shemales have long been a favourite of mine and over the years i have had several sexy encounters of all kinds. As ive got older it has become more appealing to have these beauties top me if possible. Most ive met have been quite abrupt and arrogant and have suited the top position well. Not every experience has been nice. However my last one was a really nice suprise. I was in Amsterdam working for a week and had a 3hr slot early afternoon to amuse myself so took a short walk around the red light area. I am a nicely dressed and reasonably decent looking transvestite so find the shemales in the area tend to normally ignore me going past or make lewd remarks. There was one quiet girl however getting ready in a window and she smiled and waved to me. I ... Read More»

My sissy secret

I am a male, but I have a secret. In private I dress as a beautiful sissy and no one knows. I have a large selection of lingerie and outfits, that make me hard when I wear them. Recently things have got even more exciting, since I've discovered how horny performing things on web cam. I don't care if its cocks or pussy I perform too, but if I had to choose it would be a big fat long juicy cock, deep inside my tight ass. I love the feel of a big man inside me , f***efully entering me in my little panties. I also like a cock in my mouth, in fact bukkake I'd my favourite. Only dreaming of this, I wasn't to know it would cum true x It was late one sunny afternoon and I was alone in my b*****rs cottage. I had been there for a while and apart from a few people, ... Read More»

One Night in Bangkok

Thailand is the jewel of Asia and without a doubt a must stop for anyone traveling in the Far East. The people are not only courteous they are friendly, always with a smile and eager to help lost tourists. The food alone is to die for, not to mention all the nightlife in Bangkok. Another highlight is the reasonably priced surgery that has people from both Europe and America streaming to this lovely country. Bangkok was famous for another thing and that was why I was here. The sex trade was world renown, anything you desired could be found here. Whereas most of the sexual tourists came here with something in mind they desired, I wanted to try everything. I say everything but I did have some limits such as child porn and of course, whatever I experienced I ... Read More»

Late Night in the Office

It was early spring in London, England. The sky was clear and sunny but there was a cool breeze coming off of the river Thames that caressed Mica's bare long, slender legs as she stepped out of her sports sedan. "Oh bugger, why in the world did I wear such a short dress today!" she said, cursing the unseasonable cold day while at the same time trying to hold the hem of her skirt from rising up her legs further then it already had. Mica Doren started working for Thames Incorporated as a professional administration specialist right after she graduated from a local university, but back then she was known for a different name, a more masculine name, but that was a long time ago. Throughout her early life, Mica didn't feel right about her physical ... Read More»

It was Supposed to be a Quickie

I was in a strange place, around nobody I knew, and feeling the distance. I sat at the outside bar on the beach at a popular club in Key West. My name is Jenny and I was here for a week at least, escaping. It was a beautiful night and even though I was suffering lonely thoughts and feeling like an outsider I could appreciate where I was at and the beauty surrounding me. The sun was setting and the red glow in the west was slowly fading away, the clouds capturing the last of the color. I was half sauced and was not sure what I was doing here. I'd left Miami after Jason, my (now) exboyfriend had proven what a dick he could be and just run here .... it seemed a good port in the storm. It proved to be that ..... with no Jason around anyway, but there were none ... Read More»

Devil with a blue dress

I had the whole day alone and so I decided to get dressed to the nines. After a fragrant bubble bath with body oils I began by painting my nails a pretty pinkish red and putting on my sexy little silver anket. Next my favorite black satin garter belt and a brand new pair of very sheer off-black stockings. They felt so smooth and sexy on my legs getting me quite aroused. I was getting hot already and my black nylon panties had a noticeably large bulge in the front. I was attaching my matching black nylon bra and caught a glimpse of the hot girl in the mirror. It was I. With my long hair and half-dressed I’m sure nobody would mistake me for a man even though I am one. Well, not a real man, just a sissy t girl. I was really enjoying the experience. Next I decided ... Read More»

How I Used To Cum On Shemale Webcam

I like being a shemale and doing webcam shows. A lot of guys out there would never admit it, but they really like my sort - best of both worlds, so to say: tits, asses and cocks in one convenient package. And shemale webcam was also a lot of fun - I could play with myself as much as I liked and dudes stroked their cocks and spilled their sperm, worshiping me. So, one night I was on shemale cam as usual - slow night, not many people online - but this new guy started to ask me out on a date. I dismissed the idea at first, but he was persistent; kept telling me how perfect I look, how the sight of my big, strong boobs made him hard... and a girl can resist such compliments only for a while, so I said yes. Seeing him in my house was somewhat disappointing: he ... Read More»