Shemale Fucking Guy Stories

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A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

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...

Pam's Shemale Experience Ch. 05

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

"Take it, slut, right down your throat!" "That's right, take it, fuck yes, choke on it!" "Fuck yes, babe, that feels so fucking good!" Pam swooned, kneeling subserviently as her temporary owner took her pleasure. "Fuck, Pam, your throat feels so good!" The lustful shemale was as usual in total control. One hand had a fistful of Pam's hair, while the oth...

Fantasy Oral Sex with TS Lisa Lawer

by fox-for-fun on Sep 12, 2017
Transsexuals & Crossdressers

This is a pure work of fiction and has nothing truth in it. Only truth stated here is that I am very fond of shemales and addicted to Shemale photos and movies. One particular Shemale whom I love very much is Lisa Lawer, she is from Brazil. I have been a big collector of her photos and movies. I am in deep love with her and have always fantasized about havin...

My First Shemale encounter.

by luv2getnaked on Apr 20, 2020
Transgender & Crossdressers

Only recently I had developed a strong desire to be with a hot looking shemale. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I was...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

Shemale Devil in Disguise Pt. 01

by Chomedey on Jan 20, 2020
Transgender & Crossdressers

This story talks about how a charming shemale I thought was completely harmless practically stole the love of my life and my honor. It's May 2018. I just finished my third year of University. One more year of school and I graduate with a degree allowing me to enter the job market. This summer after passing my exams, I was planning on staying at my parents...

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...

A Shemale Vacation Ch. 02

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we...

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...