Shemale Fuck Guys Stories

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Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

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...

My New Neighbours

by csm1967 on Dec 12, 2018
Transgender & Crossdressers

The house next door had, for the past 15 years, been a rental property, mainly for members of the defence force. Neighbours stayed not more than 2 years and some seemed almost gone overnight. Tenants ranged from singles, to couples, to families with children. The place had been empty for a couple of months since the previous quiet couple, and their noisy dog...

Man Is Humiliated By Escort

by fun4all6969 on Sep 12, 2017
Transsexuals & Crossdressers

I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot to do with my wife's lack of a sex drive. I recently replied to an o...

The Devil's Harem Outfit

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: Hey guys, when I was finishing my last story I found a file with this story half finished and I thought, what the hell lets finish it. Now this is a very very dark story with strong erotic horror themes that some may not find pleasing. There is some strong incest thrown in too. If you are not into that this may not be the story for you. Other...

Lust and Love with Leona

by cbachtland on Sep 17, 2017
Celebrities & Fan Fiction

This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not stop thinking of Leona and that I stayed at home fretting and loo...

Mistress Melody's Wanton Evening

by RobinTVDaniels on Aug 18, 2017
Fetish

Mistress Melody had become my mistress recently and I was very deeply in love with her. Melody is not that tall but is a very sexy black woman with long braided hair. Her dominant personality was over six foot tall though. I was a transvestite submissive sissy and I was her total slave. We both knew my little 4 inch dick would never satisfy her so she had...

A Night Out

by Parkerjay77 on Sep 16, 2017
Transsexuals & Crossdressers

I have been a long time fan of Literotica but have never considered writing anything myself. This is my first story of any kind anywhere. I did not have anyone proof read it so sorry for any errors there may be. I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink....

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...

My Speciality

by jazz4bj on May 11, 2020
Exhibitionist & Voyeur

I turned 19 and was pretty sure I was hot enough as a female to get hired by the porn industry and continue working till I am considered a milf. Why specifically? I would love to suck the biggest dicks and swallow the entire thick cum loads. My favorite thing in the world and here is how it went.. Pretty, teen sexy and a nice tanned and toned body with perk...