Shemales Porn Stories
Page 13

A Trannie takes her first big black cock

Sitting on the lounge at my local sex club I was watching the guys go by. You get to notice certain guys going past trying not to look like they are checking you out on the sly (and vice versa) thinking how they can approach me.

Normally it’s just the usual crowd of guys but several weeks ago a big heavy set African guy in his mid 30’s kept going past me and looking at me out of the corner of his eye. After about his third walk past I gave him little smile. When I could see him coming down the hall the next time I got up and slowly walked around the corner into the next hallway so he could... Continue»
Posted by toniparr 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 3197  |  
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Helping a friend

Anna has been working in my office for a year now. I have never heard her talk about a boy or girl firend. Anna is 5'7'', long legs, light brown hair almost to her waist, very pretty. I have always talked to her, had lunch, but she had never opened up until she needed some help.....

Anna had bought a house that needed work. A couple of months after she bought it, she was complaining that her sink leaked. I told her i had done odd jobs through out my life and i would be more than happy to check it before she called a plumbler. She told me to come over friday after work.

Friday came,... Continue»
Posted by edukateme 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3192  |  
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Four in four hours - am I a whore? (Part 2)

So, I'd had my passing quick bj and the guy I blew has already sent me a message thanking me for what I did for him and asking me when I'm available again, perfect !!

From the quickie it took me a while to get to the hotel, called when I was in the car park, heels on and walked across the car park with more delicious feelings between my legs, I adore walking in heels and stockings, they're always so sexy. There was a couple going into another room and the guy did a double take and smiled, murmered a 'bonsoir' before he went into the room, I think I scrub up pretty well.

It was a budget ... Continue»
Posted by antoniaf 5 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 3188  |  
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How I became a sissy

So it all started from answering a random craigslist posting that didn't even have a picture. I was off work and horny so I was cruising the ads and I came across a Cross dressing married dom and his wife looking for a sub. I was no stranger to the lifestyle and it intrigued me so I began to write an email. We exchanged back and forth for several weeks and then began talking on the phone. The day had come and they invited me over. I was nervous. I am a married guy. My wife knows all about my past experiences but had no knowledge of this relationship. I got my things together and put them in a ... Continue»
Posted by tg2027 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 3186  |  
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A little fantasy...

This is a work of fiction. It's a small window into a huge world of fantasy for me. Enjoy!

It was a wonderful day. Kristy had just moved into a new town and settled into a new job as an accountant for a local practice specializing in debt recovery and settlement. Kristy had spent the last 2 years in school and had finished to start life a new and on her own. She grew up under the yoke of her mother and older s****r. Kristy wasn't like other girls as Kristy was really born a male. At an early age Kristy displayed signs of being very feminine and showing interest in very feminine things. She ... Continue»
Posted by russianrabies 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  Views: 3186  |  
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Dad trains me to be his wife


After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from wo... Continue»
Posted by nicoleinberlin 10 months ago  |  Categories: Gay Male, Shemales  |  Views: 3164  |  
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Jeremy's Punishment

"Roberta, we need to talk." I said as my wife got into bed.

"About what?" She had her people magazine so I knew she didn't want to talk, she wanted to read.

"This is difficult, but I have to say it." I cleared my throat and looked for the right words. "I want your permission to cheat."

She stared at me for a moment. "Are you out of your fucking mind?" She asked.

"C'mon, be reasonable. I mean, how long has it been since we had sex?"

"That's all you ever think about --sex."

"Because I never get any!" I said. "Do you even remember the last time?"

"What about Halloween?... Continue»
Posted by sparkyking 25 days ago  |  Categories: Shemales, Taboo  |  Views: 3164  |  
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Caught!

Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone out boating him and I ended up skinny dipping, so I've got to see his cock several times and have secretly wished I could get him to screw Kristy. He's been divorced for about 5 years and doesn't go out much, and several times he's told me he hasn't been with a... Continue»
Posted by kristygurl 3 years ago  |  Categories: Shemales  |  Views: 3157  |  
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Allison the pool slut part 1

Allison had now had her fair share of whore experience. The teen boyslut had fallen in love with big cocks, anal creampies, facials, swallowing, and the rest of the nasty fun she had while becoming a sissy whore for her black neighbor and his dark dicked friends. Little did she know she was going to get the fucking of her life soon…


One day Allison arrived home to find a package on her door. It was addressed to Mark(her boy name) and did not have a return address just a note. The note read “Allison, I took the liberty of buying you some nasty whore clothes for when I return home in a coup... Continue»
Posted by AllisonCumms 10 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 3156  |  
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Got Caught

2 weeks ago i found myself alone as the wife had taken the k**s away for the weekend i felt the need to play. I went to work and finished early and raced home feeling very naughty indeed. I got in and ran a bath and had a nice long soak indeed and thought about what i would do and where i might get some fun at such short notice?

I got out my gear and put on a black basque with fake 40c inserts, lacy see thru black panties, black lacy top stockings, black strappy heels, skirt, top. I put on my wig and did the make up as best i could being a novice and looked into the mirror and got extremly... Continue»
Posted by abicd 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3146  |  
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hotel steam room

Once I got to high school my thoughts of wearing panties and sucking cock subsided as I became a normal teen with a girlfriend,It wasn't till I was 22 that I would realise my true passion.I traveled to Toronto with my b*****r and his girlfriend so she could right an exam.We were on a budget so we all shared a room downtown.The first evening I was tired so they went for dinner while I stayed in.While getting a beer from the fridge I noticed her suitcase open and a bra laying on top.I immediately got hard as I looked at it and had memories of my younger days wearing Lingerie.I locked the door so... Continue»
Posted by sluttysherri 8 months ago  |  Categories: Gay Male, Shemales  |  Views: 3140  |  
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my first gay fuck

I've slways crossdressed, from when I was 12 years old. I started by wearing my Mum's knickers and bra, tights, knee high boots and a dress or skirt and top. it felt fantastic wlaking around on high heels, in the back garden, knowing that all the neighbours had to do was look over the fence and see me all dressed up! My cock got so hard and I'd wank myself dry!
I carried on all through my teenage years, using girlfriends underwear. At the swimming pool, where I used to work, I'd have a shower wearing the girls high cut swimming cossies! The feel of the wet lucra around my ass and cock was rea... Continue»
Posted by Nikki_xd 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3127  |  
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mom made me her sissy

"Mom! I called out as I got home from baseball practice, "I'm home!"

"Hello Danny, we have to talk," she responded, while exiting my room.

When I saw what was in her hands, I became nervous. Some of the guys I pal around with talked me into shoplifting a few things from a department store.

"Please explain where these items came from."

I should have told her I was sorry, and that it was just the one time,

But instead I said, "Tommy made me do it. He said it was a dare. I didn't want him to think I was a sissy."

The next thing I knew, I was in big, big trouble with Mom. I got ... Continue»
Posted by momandboys 9 months ago  |  Categories: Fetish, Mature, Shemales  |  Views: 3120  |  
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How i became a sissy/my first blowjob

I'm a 17 year old sissy now but i started crossdressing 4 years ago when i was 13 :).This is the story. One day my parents went to our lake house for the weekend with my s****r but i was feeling sick so they left me with my grandparents. They were taking care of me for a day or two and i got better so they left and i was home alone.I had 5 more days until my parents were back.One day i was feeling very bored so i opened my s****rs closet and looked at her stuff. I noticed thongs,i never knew she wore them (she was 17 back then). I wondered how they would feel so i put them on. I never felt sex... Continue»
Posted by sissygirl1988 8 months ago  |  Categories: Fetish, Shemales  |  Views: 3121  |  
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I final found him and his friends

For the last 7 years or so I have been from one guy or girl to another looking for someone that I could serve sexually and not interfere with the rest of my life.

Last month I finally found him. I was at the local porn shop on Friday night cruising the theater and the peeps as usual. I was in the Theater by myself in the back row when a guy walked in he looked to be about 35-40 average build dressed in blue jeans and black shirt. He sat down across the aisle from me on the back row out of site from everyone coming in and out of the 2 doors. I sat there for awhile then decided to move ba... Continue»
Posted by tim_likes 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 3113  |  
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3 weeks in Thailand

6 weeks ago I went to Thailand – Koh Samui for a 3-week holiday just to get out of the system.

I was on my own, in my 50s, divorced and mainly hetro but enjoyed a passing gay experience with “Jon” from a now closed down massage parlor in Manchester UK (told that story a few months ago). So went to Thailand - thank god for Viagra – to fuck a few hookers, get d***k and have a nice break. The bars at Chewang Beach were crowded and “factory like” , full of tit and sweat and I didn't like them. The girls were “well worn” and “routine” if you get my meaning – “me make you fucky fucky long time” ... Continue»
Posted by jimtheman699 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 3113  |  
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Stacy

I had known Stacy for about three years, but I had never known about her little secret. That day when it was revealed changed everything for me, and for Stacy too. We were the greatest of friends, spending almost all our time together. We had come as close to each other as lovers but as two women, neither one of us ever made a move.

My tale begins during the heart of beach season. It was a beautiful sunny day. I had suggested to Stacy that we take a trip to the beach and enjoy some sun and sea. But Stacy told me she didn’t own a bathing suit. The perfect excuse for shopping. I could have k... Continue»
Posted by LadyShi 2 years ago  |  Categories: Shemales, Taboo  |  Views: 3103  |  
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My first BBC fuck!

I went clubbing last week with my girlfriends that I work with and they recommended a hip hop club in a seedy part of town. I was alittle scared but we went anyway and well, and we were really having some fun there!!! I decided to dress like a real lil slut this night, a black minidress, lacey thigh highs and garters and black fuck-me pumps.

My girlfriends hooked up with some cute black guys and took off leaving me there kinda by myself. I was being hit on constantly by these hot black guys but I wanted a white guy, or at leas... Continue»
Posted by sataori_fukame 11 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 3104  |  
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He has made me the town slut

We live in a very very small town, and now I am the town slut. This is the story of how my obsession with one mans cock turned me into the town slut.
I had been sneaking over to see Phillip every chance I could after he had fucked me and let me suck him. I couldn't get enough of his cock. I tried to see him at least once a week. I would usually blow him, but sometimes he would have the time to fuck me good and hard. I get off work hours before my wife and Phillips wife works later so this gives me time after work to dress up and head over to their house for some sissy fun.
One part... Continue»
Posted by firstknightd 1 year ago  |  Categories: Group Sex, Shemales  |  Views: 3100  |  
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I finally take the plunge

I finally take the plunge - a crossdressing story

I'd been crossdressing for a few months at this point but I'd never gone outside while dressed in women's clothing. I'd been to the shops once, wearing one of my outfits under my normal male clothes; that's the closest I've ever been but even that gave me an intense thrill. Even under a fairly loose coat, I'm sure people could make out the outline of my breast forms. Since that little trip to the shops had got me so aroused, I was determined to do it properly next time so I decided that the following Friday I would go clubbing ... Continue»
Posted by CDer 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3100  |  
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