Man Spends Night With A Shemale Story Stories

372,004 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Call in the Professional

by xploring96 on Oct 15, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, prostitution, Domination/submission, and derogatory terms used to humiliate. If this offends you please do not read any further. ***** How did Greg get here? It's election day in Washington DC and he is standing in the Ronald Reagan Airport with a big problem. To understand his problem it is important t...

Saving The World Porn Review #1

by vic_elor on Sep 16, 2017
Reviews & Essays

Since I seem to have sufficient free time and a steady access to pornographic material, I have taken it upon myself to save the world from bad porn! How am I going to do that you ask? By watching lots of porn, jerking it a few times to clear my head, and then give it either my thumbs up or thumbs down. My system of review will be fairly simple. I will pro...

Hooking up with a shemale

by Gliorna on Apr 29, 2025

You are Blake Tallbrook, a semi wealthy man living alone for the moment after a break up a year ago. You have been working hard for the last year just focusing on your job. Your Sexual life has been normal one night stands with random girls from bars late at night. But you have become interested in something else. A girl with something special. You have look...

Open in Reader

A Night with a Sexy Shemale

by MajesticLVR87 on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down s...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

Open in Reader

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...