Shemale Piss Stories

24,697 results
Orientation
Length
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Infinite Scroll

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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A Night Out

by Boomerjr34 on Sep 12, 2017
Transsexuals & Crossdressers

NOTE 1: I'd like to thank those who edited this story and helped make it better. Gaymaninawomansbody, Kate09 and ThePastBehindMe. NOTE 2: This story has had some man on man sex, shemale on male sex, group sex and a woman too. ***** I have been working with the same sales group for years when they hired a new guy from out of state. He moved to town when hi...

Brazillian Punsihment

by Ravenarioch on Feb 7, 2018
Transsexuals & Crossdressers

Frank Shepard a private detective who is trying to find his luck in Rio de Janeiro awakes in his bed during the day of Carnival, the sun's rays hitting his eyelids he turns himself over in bed and looks at the sky on this lovely day. His sky blue eyes thinking about what a horrible day to be a private investigator, his case was to find the little brother of...

Mia, Shemale Slave Ch. 02

by spitzharder on Sep 13, 2017
Transsexuals & Crossdressers

My pre naming party was held in the nightclub where Mistress Solange and many of her Shemale friends, performed. They sat at a private table but I had to stand as I was wearing a creation of Mistress Tia's. A spun sugar, almost gauze like confection held up only by the gold rings piercing my nipples and navel. The lime green bikini was almost transparent and...

My New GF has a Dick

by DixeenormousToo on Dec 17, 2018
Transgender & Crossdressers

I didn't go looking for a tranny, shemale, dickgirl, or whatever derogatory term a homophobic world has labeled women that happen to be packing a penis. In fact, while I had messed around a little with the man worm, back in college and with a drunken buddy a few times, I considered myself 100% a hetero male, in love with the female form and a total horn dog...

Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

Hung Trans Lesbians Fuck Two Ladyboys

by mrstanley on Jul 15, 2020
Transgender & Crossdressers

I haven't written a Trans story this year. In this story I try to describe more intimate intense scenarios with a wider variety of details. If you enjoy the story please vote and comment. Feel free to read my Fetish and Mature stories as well. Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, A...

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...