Shemales Porn Stories
Page 122

A girl from the bar

This guy picks up a chick in the bar and takes her to a private room, the only thing on his mind is to fuck her, but there’s a surprise that the chick has prepared for him!

When I stepped down to the hotel’s bar I didn’t even notice that girl at once. I sat my ass down on the sofa in the corner and ordered some whisky. A waitress girl said I needn’t to pay for my drink as it was checked by a girl sitting near by facing me. I looked at her: it was young fresh meat like blonde babe who looked very horny a bit sluttish. She was beautiful. Rosaline, her name, was wearing black leather skirt and... Continue»
Posted by princessamyov 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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TV Times

One evening I was online when someone wanted to start a chat with me. It was a bi guy who enjoyed cross dressing and having viewed his online profile I said “Hi” and we got to talking.


He was married guy named Mike and he had a very understanding wife who allowed him to meet men and allow him to explore his feminine side by dressing up. His wife did not participate with him and none of his explorations happened at home.


During our chat he explained he’d just bought a pair of long, nearly thigh high, boots and he longed to be fucked whilst wearing them. He was off th... Continue»
Posted by hotbiguy 5 years ago  |  Categories: Anal, First Time, Shemales  |  
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Something in my drink, the captive part 2

So there I lay face down in the floor, hands bound a ball gag in my mouth and cum dripping from my mouth and ass, those tranny bitches really did a number on me, and left me like this in the floor in a dark room, exhausted and still confused from the mickey in my drink I feel asl**p.

I did manage to get some good sl**p, and I awoke to Tara giving me a sponge bath, my hands still bound, and a collar around my neck chained to the rails behind me, I was still a captive with no options. Tara was being much more gentle to me this morning, even feeding me breakfast, brushing my teeth, and puttin... Continue»
Posted by smonkeys32 5 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My beginning

I have been a closet cross dresser since my early teens seeking my mother's panty hose and underwear I thought I had kept it well hidden when I turned twenty I got a place of my own I found it very hard to get my women's clothing since I didn't have the courage to go out in public which brings me to my story . a friend of moms named Sherri was bag ng problems with her old man and they had spot up she came to me and asked if she could move in and help with the rent I was all for it Sherri wes a tall red head very pretty and we'll built a couple of weeks went by she was gone one evening a pair o... Continue»
Posted by mike63bear 5 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Her first shemale

It was no secret to me that my girl was bi; we had talked about it and I encouraged her to express and explore her bi side. When I managed to get us a date with a hot girl, I decided to keep it a secret.
I took my girl to a nice dinner, and while being seated our date for the night showed up and introduced herself- her name was Ann. We had a nice dinner, and on our way back I asked the girls to sit on the back seat. Ann was not shy, and neither was my girl, so before I knew it Ann had her hand up my girl’s skirt and they were kissing hard. By the time we got home, my girl was already wet and... Continue»
Posted by angelslover 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Getting caught on purpose ( true )

I had gotting tired of my mother showing up at my house everyday with out notice.She always came in and whated to move stuff around and say something about a dish in sink or what I had cooked for dinner last nite.I love her but since her boyfriend past away she was driven me crazy.
So I woke this morning early and asked her if she wanted to go shopping with me.She said yes I bought some heels bras painties and we went got our nails done.She asked do you own any male clothes I told here no.Well I dropped her off at her house and left and 20 minutes later she showed up I tried to tell her cal... Continue»
Posted by cdpaula 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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Fucked in a sling at an ABS

So there's a cruise place here in Canberra where mainly men go, it has a cinema and blowjob are downstairs and private rooms and some fetish rooms up top. Knowing of this place i decided to venture out all sexed up as Rachel.

At home I shaved and used hair removal cream to make my skinny body more feminine, then rubbed body lotion into my skin making me softer and sexier. My she cock is already half hard at this stage and I have a sissy trainer video on to remind me that I am a sissy slut who loves cock.

Clothes I wore a crotchless fishnet body stocking and a PVC teddy and gstring. I put... Continue»
Posted by rachel_cd 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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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 3 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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my gardner plowed me

My wife and daughter had left to spend a week with my mother-in-law in Brazil. So it was time to breakout my secret wardrobe. Having two women in the house made it easy to keep a sexy supply of clothes. Add a wig and some makeup, I'll soon be lookin pretty hot.

I started by shaving my body and taking a long hot bath in some lovely smelling bath oils. Just the thought of dressing up was making me wet. I dried off and went to get dressed. Being in a wheelchair made it take a long time to get dressed. I wasn't even going out but I wanted to dress up and maybe video chat with some hung studs, ... Continue»
Posted by cdaisy1 4 years ago  |  Categories: Shemales  |  
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My wife introduces me to submission and cuckoldry.

It took me a while to come clean to my wife about my time before we met. In that time i had been a submissive to a Professional Mistress in the Midlands and it was from her that i developed an interest in both servitude and crossdressing. Mistress/Madam had always insisted that i should be dressed as a woman whenever i was in her presence. After Mistress/Madam and i had gone our separate ways after many years of being together i had to admit to feeling a little alone and deserted and with no direction in my life. i had several relationships and none of them had any idea about what i had been ... Continue»
Posted by oldognewtrix 5 months ago  |  Categories: BDSM, Mature, Shemales  |  
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A Night to Remember

About six years ago just before Christmas I went to a transvestite bar in the centre Manchester after I had finished my act at a private party on the outskirts of the city. I was dressed in my sexiest outfit mini dress, suspenders, sheer stockings and 4-inch Fuck me hard stilettos, and my favourite long brown wig. I was fully made up with long false eyelashes and blue shadow, red painted finger nails, and dark red lipstick, pearl necklace and large chunky earrings. I looked quite stunning . I have a very good figure and long shapely legs. I need to, in my line of work, as a part-time tranny... Continue»
Posted by TgirlViki 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
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The Shoe Store

The Shoe Store
By
L

Adam hated working Wednesdays. He works the entire day from opening to closing every Wednesday. His manager always takes Wednesday off. This was mostly a boring day for Adam. A few women came in the store before lunch which was a disappointment for Adam. Adam is a bit of a pervert. He likes to take a peak up a woman’s dress or skirt while he is putting on shoes for them. The morning customers all were wearing slacks.

A woman came into the store a little after lunch time. She was wearing a halter top with a short skirt, stockings and heels. Adam went over to her ... Continue»
Posted by Len1958 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 5 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Singapore tranny sex

My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this special nite i had never met her. Anyway, this nite as we got back to the flat Meena was in too, taller and bigger tits than Lin. Well we got on very well, the drink flowed, talk turned sexy, and Lin said that she had told Meena how gr8 i was in bed! We all laughed, then i grabbed Meena, kissed her face,... Continue»
Posted by horneybial 4 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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How i became a sissy fuckslave pt2

Sometime later, i'm not really how much later since i seem to have dozed off, Sir came back in and woke me up by swatting my ass hard"Wake up slut".

Sir unlocked my cuffs, and my ankle restraints and said"Down the hall, second door on the right is the bathroom, go there, remove the corset, catsuit, boots and hood, remove the plug and clean it and yourself up.When your done I want you to put the corset on, and hood as well as the boots and then go to the room across from the bathroom.Don't worry about cinching up the corset, I'll do that when you get in the room.If you have to pee, your to... Continue»
Posted by analsubbieinmissouri 5 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The new "Girl" On the Boat

I have mentioned in previous stories that my career was spent as a Captain of a high end 100' charter yacht working the waters of Alaska. It was a job that provided me many opportunities to 'play' with men, women and couples, most of them older, and all of them very well-off financially.

Passengers and crew had to sign agreements that I could inspect their rooms and belongings for any reason whatsoever, though I assured them it was very unusual for me to do so. For the crew, my main reason for conducting such inspections would be to check for i*****l d**gs.

But another reason for chec... Continue»
Posted by 1kaaboom2 10 months ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Living with Mother ….. continued

Living with Mother was always interesting, especially because she loved to see me dressed as a girl/woman. For almost 4 years, weekends would always be special time, whether Mother, my s****r and I were at home together or whether I was there with either of them. The dressing was just what I did, evenings were always rather easy but the weekends much more intense.

A typical weekend would start Friday evening when I returned home from school, straight into the bath, made myself as clean as possible and then into the clothes I had laid out before I went to school that morning. Nothing too ... Continue»
Posted by antoniaf 4 years ago  |  Categories: Fetish, Masturbation, Shemales  |  
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Me dressed as a Gurl

this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late about 8:30pm the company was fine mainly playing pool and looking around some good conversation us gurls we in back the guys were in front at the bar checking us out i was dressed to kill had on black 4" spiked heels with mesh stocking to my teights with a garter belt and black thong blac... Continue»
Posted by jackguns 5 years ago  |  Categories: Anal, Shemales  |  
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A video shoot - Part 2 of 2

Now there are even more guys on set. About half seem to be jacking off. I ask John what he has up his sleeve and what he needs me for.

It a Bukkake film. Damn, I get to see Tina covered in cum. My cock twitches at the thought. John tells me he needs a fluffer. I don't quite understand. After all Tina is just damn hot. Who would need a fluffer to cum on her? John says Tina is too girly. WTF? He says well some of the guys are gay and are having a hard time getting up. No pun intended. I now get what is happening. I protest weakly. But I am almost in pain from being horny as hell.... Continue»
Posted by nobodywashere 5 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The visit

It started out simply enough, I was visiting my s****r and
her husband for the week. They both work so I had the run of
her house and I took advantage of the opportunity to sl**p
in on my vacation. I woke late and assumed everyone had gone
for work. I took a nice long relaxing shower, s*s’s bathroom
was warm and cozy so I took my time.

When I went to put my towel in the hamper I noticed a very slinky
teddy and panty set on top. I had never thought of my s****r
wearing anything like that so I picked it up and looked it
over . It was pink silk and trimmed in lace. It felt so soft,
I ... Continue»
Posted by pandys 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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