Shemale Fuck Guy Stories

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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...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

Pinch Hitter Ch. 01

by npanxx on Sep 14, 2017
Anal

This is a work of erotic fiction. All characters in the story are over the age of 18. ~~~~ My fascination with shemales had cost me my first marriage. I guess if I were to be honest with myself I would have to admit that the marriage was doomed to fail anyway. Barbara was as close to being asexual as a person could get, and in addition she was bitchy a...

Crystal, Meth and Me

by MrStaggerLee on Sep 11, 2017
Transsexuals & Crossdressers

Author's note to the reader: The objective writing this story was to capture a really seedy and sordid encounter involving a few men and a transsexual prostitute. The story is sexual in theme and could be considered erotic by some, but it's also pretty dark and bleak. You have been warned... I wasn't sure I remembered the last time I had seen Crystal stra...

Transwood High Pt. 04

by BoobVillian on Sep 12, 2017
Transsexuals & Crossdressers

Christmas is Cumming... Authors note: All the characters in this series are over 18, this is the fourth part of the serious so be nice :-) Sorry for keeping you horny for so long, hopefully this satisfies. The story focuses on our main heroine, and some new/ old faces appear. Enjoy and leave comments! ******************************* 10/12/2016... 'Open u...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

First Time with a Shemale

by BigAndy922 on Sep 13, 2017
Transsexuals & Crossdressers

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favours. I liked my share of porn, and as I had...

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...

Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Trip to London Pt. 02

by plez2tease on Sep 17, 2017
Loving Wives

I wake up early Tuesday morning and feel a little excited. Today is the day my husband and his friend have been planning for over a month to make happen. The only part I know about the plan is that I am supposed to dress in what my husband has provided me for the day and that a car would be here at the hotel around 11am to take me to some place. I was told t...