Shemales Porn Stories
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Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 705  |  
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Smoking TV tart

My makeup was perfect. Well, I say perfect, others would disagree. My red lips glistened with 4 coats of shiny lipgloss. Outlined in black liner, overdrawn to make the lips look large, and inviting. Heavy red blusher outlined my high cheekbones. My eyes were coated in a mix of eyeshadow and vaseline, giving the pink and white segments a shiny wet look, below the two inch long, heavily mascara'd eyelashes. The back combed platinum blonde wig, piled high above large diameter, dangly hoop earrings. He hadn't specifically asked for the OTT drag makeup, but had demanded my black PVC leotard, and ma... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales  |  Views: 845  |  
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I am such a slut......13

I am such a slut......13


Please read my other blogs to catch up. They are true, part confession, part cathartic. I love your comments. ~Dani


Day by day I am becoming more feminine. I can now notice the changes when I look at myself in the mirror. A big step was getting my hair professionally done. Yes, it was a bit embarassing going into the salon, but the ladies treated me so nice, laughing and sharing stories, some telling me that they would like to fix me up with their husbands. But properly cut and colored and styled, it made me look so very feminine. And while I was there I ... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 2160  |  
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My First Time with a Transexual

I was in a large city about 100 miles from my home for a week on business. I had been hitting the bars for a few days with out a lot of luck. On the way back to my hotel afer work one day I picked up a few of the alternative newspapers/sex ads. Checking the ads out later I saw women, men and transexuals all offering there services. I saw one picture of a beautiful blond and was blown away to see that the ad was for a transexual. I called and made arrangments for her to come to my hotel in a few hours. I busied myself shaving a showering for when she would arive, putting on a pair of gym shorts... Continue»
Posted by Bob111401 3 years ago  |  Categories: Anal, Shemales  |  Views: 1980  |  
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My new CD bitch.

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This is the fantasy exploration of an on-line “friend” here at xHamster. She is a very hot Cross-Dressing boy, her fascination with the feminine part of her is new… it was for a time my pleasure exploring with her this new “side” of her… the story is on going – with three chapters written so far… I will post more… and if she decides to continue this explorations, there may be more stories…


~-~-~-~-~-~-~-~-

My new CD bitch.

CH 1

I decided to fly to St Louis, I had some business to do there - it could be handled over the phone, but it has been a while since I was ther... Continue»
Posted by TomStone90045 3 years ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1775  |  
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Confessions of a smoking TV tart. Part 1

"What did you feel like tonight, in the car park?" he asked. It was uncomfortable for me, tied to the back of the chair, upside down. 'It was such a buzz, the adrenalin was incredible. I've never felt more alive.' I answered, the rubber bonds gently squeaking in my discomfort. "Why?" I pondered for a while, before answering. 'I love knowing that when I dress in all my heavy makeup, the plastic and rubber, and the come fuck me boots, it gives guys a big hard on. It's a big compliment that I'm doing things right.' My master reached into his big holdall on the bed, and then sat in the chair backw... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 918  |  
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More Dirty Sex with Tania. Part One Hotel Sex

More Sex with Tania


Part One. Hotel Sex

It took quite some planning, after our last meet in the lay-by, but at long last we had both been able to get away at the same time. We, well actually Tania, had arranged our meet to be at the Premier Inn at Witcombe, just south of Cheltenham and just of the A46. Tania was arriving just after lunch and myself at about 3ish. We agreed it that way so it gave Tania time to dress and get ready, however it did mean that I would have to arrive dressed as Joanna. I have a lot of confidence when dressed, as Joanna but most of my forays have been either a... Continue»
Posted by joannacd1 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  Views: 1521  |  
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playing iwht th juicy pussy!

HAVING TO SPEND THE NIGHT WITH MY SHEMALE FRIEND, WELL TURNED INTO MORE THAN I HAD EVER EXPECTED! AS WE FINISHED MAKING LOVE, SUCKING OUR COCKS AND ASS FUCKING AND CUMMING OUR JISS ABSOLUTELY EVERYWHERE, I DECIDED I WANTED A COLD COCKE, AS DID MY LOVER, SO I PUT MY ROBE ON, WENT OUR OF HER ROOM , AND MY WAT DOWNSATIRS, I HEARD MOANING AND A SLIPPERY SOUND COMIN FROM HER 19 YEAR OLD s****r'S BEDROOM, WHI IS A STRAIGHT GIRL, YET ABSOLUTELY STUNNING, LONG BLOND HAIR, ABOUT 34B TITS AND A GREAT ASS, TO WHICH I WOULD FING OUT MORE IN A MOMENT. I PEEKED INTO HER ROOM, SHE WAS SPREAD LEGS ON HER BED,... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 1406  |  
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My journey into Hedonsitc crossdressing, Part 2

My mind was spinning. I'd spend the last 10 minutes or so sucking my first cock. Now, I'm being told to prepare myself for taking my first cock inside me. Do I want to get fucked? The reality of what was happening was almost too much to handle. Vince had guided me back into the bedroom, spun me around and helped me out of my dress. I slipped off my briefs (finally!) and my cock had been oozing precum.

I was highly intimidated now...standing completely nude, in front of Vince, who was also nude. Vince seemed to sense this and began telling me that he looked at me as very f... Continue»
Posted by elainetgrl 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 743  |  
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Confessions of a Smoking TV Tart. Part 2.

Gosh! Where to start? 'I've got so many fantasies, but they ALL involve me being used as a cock-sucking, cigarette smoking spunk slut!' As my thoughts trawled through so many kinky scenarios, my cock pulsed ever harder above my face. My tightly bound dick getting ever more solid in it's binding. Master pushed the dildo slightly deeper into my wanton hole, and I could feel it was ribbed, and growing thicker. "Tell me about your first outdoor meeting." he asked gently, easing the dildo in a slow fucking motion. The discomfort of my position was beginning to be overwhelmed by gentle pleasure. 'My... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 267  |  
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am such a slut…..16

I am such a slut…16

The warm water of the lilac scented bubble bath felt so good as I slipped down into it. My hair, now much longer, clipped up on my head to keep it out of the water. As I slid my body down into the water I felt it embrace me and warm me and how nice it felt as it surrounded my body. Finally a chance to relax and reflect. What a day I had. I let my hands slowly drift over my body. So soft. So smooth. My now protruding nipples aroused by the warmth of the water. Some small teeth marks on one from the back room at the adult theater. I giggled to myself as I ran my finger ove... Continue»
Posted by snuggle11 3 years ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 2994  |  
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becoming the girl i really am part 2!

I smiled up at my best friend, dressed up in sexy lingerie and smiled, "Can i dress up too?" i asked in a hopeful tone of voice. "Oh, wow, really? Yea sure!" brian answered with excitement in his voice. "Go into the guest room, my s****r keeps all her clothes in the dresser and the closet, and pick out soemthing you like!" he said, "Pick something really sexy" he whispered as i slipped out the door and into the guest room.

Going through the dresser i found a drawer full of panties, i felt a rush of excitement as i examined the soft, silken panties....thongs, bikinis, g-strings and boy s... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: First Time, Shemales  |  Views: 487  |  
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Road trip


I enjoy dressing as a female. I do it as much as I can. I wear nylons or tights, support panties or girdles, and bra’s regular or long line under my clothes. I have a pair of knee high boots with 4” heels that I wear when I can. I am also into bondage.

Every now and then I get a chance to do both. This is the story of one of those times. I had to make a trip from Memphis to Nashville. It was to be an overnight stay. It also was going to be a daring fetish bondage trip.

I packed for the trip. More bondage and cross-dress than anything else. I took ropes, cuffs, my favorite vibrating dil... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1006  |  
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The Bondage Whore, Chapter 3

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 3 - Other Belated Discoveries

That evening, back at the "fleabag", as Rachel referred to home, Rachel peeled off her miniskirt and approached her prized posession -- her full-length mirror. She studied the collar first and was shocked to see that there was an engraving on it, in big letters: BONDAGE WHORE RACHEL ST.CLAIR, PROPERTY OF STOCKHOUSE ENTERPRISES. It wrapped around almost the whole collar. "I walked home with that visible to the world" Rachel thought to herself, shocked.

Then she studied the horrible nast... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 798  |  
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DEEP INSIDE OF JAMIE HARTS

'DEEP INSIDE OF JAMIE HARTS 'MORE THAN A WOMAN' CHAPTER 1 IM jamie' i have been bi-sexual from age 15 and wanted to be a girl for just as long. This is about my three years in prison from ag... Continue»
Posted by jamie-harts 3 years ago  |  Categories: Interracial Sex, Shemales  |  Views: 667  |  
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Kelly goes to college part 3.

I stood in the club, the music pounding and the lights pulsating around me, with the taste of kennys kiss still on my lips. I was shocked! This cute boy Kenny had just kissed me and told me I was beautiful, i felt sooooo warm and fuzzy inside when he told me that....it was awesome!

i stood bubbling with excitement and happiness for a moment, in my mind i couldn't quite believe that this cute college dorm mate of mine had just kissed me and told me I was beautiful! "YOu're soo sweet" i said, wrapping my arms around his neck and kissing him again, "You just made this girl feel soooo good" i ... Continue»
Posted by dirtygurl4u 3 years ago  |  Categories: Shemales  |  Views: 679  |  
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Neighbourhood watcher (part 1)

Walking through my kitchen to my bathroom, the 6 inch heels of my white patent thigh boots clicked and clacked on the tiled floor, my black plastic mac rustling provocatively. Out of my drawn net curtains, I noticed my neighbours kitchen light was on, illuminating the dark damp winter night. As I pulled my swelling cock out from my skintight red rubber miniskirt, carefully, with my 3 inch red talons, to pee, I sneaked a peek through my small, open bathroom window, across our yards, to see his muscular shape. I'd wondered if it was he who posted the note through my door, simply saying, "I love... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 715  |  
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Neighbourhood watcher (part 2)

My heavy makeup was complete, with very long false eyelashes, and my heavily glossed red lips glistening, ready for the big screen. My shoulder length, fingerless rubber gloves were tight, but somehow comforting, my deep red nails contrasting sharply with the shiny jet smothering my arms. My black PVC leotard was tucked under my semi-transparent, smooth, wet looking, red rubber miniskirt. The hair tonight was blonde, big, and back combed. I left the bathroom light on, dimly illuminating the small kitchen, hoping my shinywear would be spotted, glistening, as I tottered back, slowly, and seduct... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 284  |  
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He shared me with his friends

I was in an adult book store in Bradenton Florida. I had my sissy cloths on under my male street cloths. Once I was in a private booth I took of my male cloths and was left in my bra, panties, and thigh high stockings. Some lipstick and I was on my knees at the glory hole waiting to suck some dick. The first one through the hole was nice. Clean. I suck him for a while when he bent down and asked to come into my booth. I said sure and he went around to the door and I let him in. I dropped to my knees again and took his dick out and took up where I left off. As I sucked him I played with the nex... Continue»
Posted by firstknightd 3 years ago  |  Categories: Shemales  |  Views: 1350  |  
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Neighbourhood watcher (part 4)

My cock felt fit to burst as I wanked. My red rubber miniskirt squeaked in delight, in time to the masturbation. My large PVC tits peered from inside my black mac, and my white thigh boots gave me added height and confidence. My neighbour stared down at me, lusting haughtily at this lascivious lovely, stroking his cock, behind his window, in the dark. I teased him by dipping my long cigarette holder into my dripping cock slit, then sipping the juice as I inhaled a reassuringly large lungfull of sexy smoke, and exhaled it gently back over my perpendicular iron-hard glans. My ciggie was soon fi... Continue»
Posted by HonorAnneDObey2 3 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 163  |  
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