Male On Shemale Stories

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Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

ShemalePrey.com

by Wazzfup73 on Apr 24, 2019
Transsexual

(Apologies that this is not in the Guidelines, but the term 'shemale' is used only for the purpose of erotic fiction and should not be as a term or to represent trans women in real life. Apologies to any people it may offend) As the alarm clock goes off on my phone and your mom shouts your name 'Ryan' to come down for breakfast I jump out off bed to look at...

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Becoming Victoria

by Writer345 on Sep 18, 2017
Transsexuals & Crossdressers

Prelude. I was happily married and still am, but things have changed; or should I say that things have been changed - I have been changed. I was or rather am still wed to Anika, a rather dominating Polish lesbian, who married me for reasons of her own that are still a mystery to me. I'm not the man that I was...Oh, this is so confusing I'd better start at...

The Society

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living i...

Blackmailed by a Bitch

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'I got it,' Laura said, running into the kitchen. 'I got the job!' That's great,' Dave said. He hugged his fiancée, full of joy at the news. Laura had been desperate to find a new job. Anything to get away from the place where she worked under her nightmare boss, Gloria. 'When do you start?' Laura's smile disappeared. 'As soon as I get my reference.' 'Fro...

MarryYourFuta

by mimi1988 on Feb 21, 2018
Transsexual

**[Sorry for publishing the story without an ending, but I will try to do a chapter every day :)]- - - - - - ** Im a young boy, im 22 years old, i start living by myself and because of that im feeling lonely :( Im new in this town, and i have no friends here, my job suck (it's a callcenter) i need to meet new people fast because im going crazy. I found this...

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Trucker's Surprise

by Mymantoy999 on Apr 3, 2019
Transgender & Crossdressers

NOTE 1: First I would like to thank Silkstockingslover for granting me permission to use her name and story title as a background for my story. NOTE 2: This is my first attempt at fantasy, meaning other than the fact I am a truck driver and I do like the food at Petro truck Stops, none of this is factual in any way. NOTE 3: As stated above this is my fir...

Small Cock Frustration

by jamtby on Oct 8, 2019
Transgender & Crossdressers

In 2007 I suffered from a severe medical condition which required extensive surgery. The procedure saved my life but the removal of my prostate, bladder, and extensive nerve damage left me without a functioning sex ability. My cock and balls remained outwardly normal but they were not doing what they were supposed to do. The relationship with my wife became...

T-Girl Van Sex

by available269 on Sep 12, 2017
Transsexuals & Crossdressers

Pulling up to the curb near the bookstore one recent night, I happened to notice a nice looking custom van drive by very slowly. Looking intently at the driver as it passed by, I noticed that the driver was a very sexy looking woman, and she gazed at me intently as she passed by. The van pulled up to the curb in front of my car and parked. Shortly afterwar...

Punished in Paris

by maia24 on Sep 16, 2017
Transsexuals & Crossdressers

Maria the very pretty Irish transvestite had arranged to meet the men in Paris. She had agreed to be taken to a house in the suburbs to be punished, abused and sexually defiled by a number of men. She was dressed in a purple mini dress and wore very expensive lingerie. She was totally smooth and as she walked to the avenue to meet one of the men she was full...