Shemale Fucking Guy Stories

242,521 results
Orientation
Length
Source
Infinite Scroll

The Sexiest Shemales Ch. 02

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

Holly and I didn't want to waste our day so got up and got ourselves in the shower. We stripped off our g-strings that we were still wearing from our sex fest and turned on the hot water. We always shower together. Sometimes we will fuck each other in there or suck each other off but we just had sex so we just soaped up each other's bodies and cleaned the cu...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

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...

Mistress' Shemale Cock Gift

by MasterHornedGod on Jul 4, 2018
Transsexuals & Crossdressers

Mistress strides into the playroom in her usual seductive way, her curvy hips swinging side to side, very large full breasts jiggling ever so slightly even though squeezed together to form a captivating cleavage by her black latex skin-tight leotard. A see-through chartreuse skirt accentuates her luscious hip curves, revealing the french-cut leotard plunging...

Amanda and Me Ch. 01

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception. As I w...

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...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

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...

Adventures of Shemale Sandra Ch. 01

by Elyquent on Sep 14, 2017
Transsexuals & Crossdressers

His name was Phillip. Or at least it had been. Honestly, he wasn't sure who he was; all he knew was that what he had done two years ago was what he thought was right. This was the lifestyle he wanted. It should be said that Phillip has always had strong female influences throughout his life. He and his three sisters were raised in a single parent home by th...

My Shemale Mother

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is... I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I...