Transsexual Fucks Guy Stories

150,484 results
Orientation
Length
Source
Infinite Scroll

Vanilla Fudge

by bb1212 on Sep 13, 2017
Transsexuals & Crossdressers

This story could have gone into either the non-consent / reluctance or into the transsexual / cross dresser category. It contains explicit description of a non-consensual encounter between a transsexual and a straight man. If this is not your thing please pick a different story. I am happy to receive feedback, positive or negative, about the characters or st...

Walt Pt. 02: A New Beginning

by AngelaK on Sep 14, 2017
Romance

2005 24-25 yrs. Old Ch. 1 - The first Date I enjoyed being fucked hard, and occasionally, roughly. I even enjoyed mild 'discipline'. I could handle someone using a riding crop or belt on my ass for short periods. I was pretty freewheeling when it came to sex. I wanted it frequently. I experimented my new found gender freedom with as varied a group of sex p...

The Sex Experience of Lady Rhua Ch. 01

by hentaiboy69 on Sep 13, 2017
Transsexuals & Crossdressers

The story "New Year Eve with Puppy" has born as a standalone to celebrate new year, but now it will be followed by others. All together, they form the sex experience of Lady Rhua. ***** The sex experience of Lady Rhua - Intro The web is a place where is possible to find anything and anyone, and if it's used in the right way, it offer us protection, a...

Transsexual Journey 01

by walterio on Sep 19, 2017
Transsexuals & Crossdressers

PRELUDE Jay woke up to the gentle movement of the cruise ship through the Atlantic. His bladder needed relief so he eased out of bed and quietly used the bathroom in the stateroom. Once he had taken his morning piss, he washed his hands and cock before crawling back in bed. As he approached the bed he admired the Spanish beauty lying there with her back to...

Becoming Dannii Full Time?

by seams_straight2me on Sep 5, 2018
Transsexuals & Crossdressers

Mia and Linda had kept their word. Two large framed pictures of my Dannii photo shoot were delivered, and had I not been there when the pictures were taken, I would not have believed that was me in those pictures. Linda had done a fantastic job with those pictures. One was a solo portrait of me, my tits squeezed together, lips looking inviting in a moist red...

Transsexual Temptation

by danielblue on Apr 3, 2019
Transgender & Crossdressers

Roger had been working with Ben for about six months and had decided that he really was a cool guy. They shared the same sense of humour and had several interests in common so it was natural that they began to spend a lot of time together. But the more Roger got to know Ben, the more worried he was about something. He was a little uncertain about his feelin...

Sucking Futanari Cock at the Interdimensional Gloryhole

by Johnman13 on Jan 7, 2020
Transsexual

As is typical for me, this story is a work in progress. Not much has been fleshed out just yet. Updates will most likely be spontaneous and irregular, so watch this space. I've created an online suggestion box [at https://poll.ly/#/LBeYMr9X] for characters you'd like to see. Don't be shy. It can be as mundane or as wild and wacky as you want. My only rules a...

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The Parking Lot Ch. 01

by LatexSolarBeef on Jul 13, 2020
Transgender & Crossdressers

My buddy Robbie, an old family friend, is much younger than I am by nearly 20 years. But we've always been close and enjoy hanging out. He was working as a landscaper one summer while in college. He invited me to hang out at a bar in Lavallette where he and his pals shot pool and drank beer on weeknights. It sounded relaxing, so I went. Only one other guy w...

Black Like Me In Ottawa

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

What's up people? My name is Stefan Brandon Eustache and I'm a young Black man of Haitian descent living in the City of Ottawa, Ontario. I hold an MBA from the Sprott School of Business at Carleton University and work for the Canadian Revenue Agency. I have a lovely home in the suburb of Orleans, which I share with my on-again, off-again girlfriend Stacey Ed...

The Agreement Ch. 02

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Neither Sarah nor I spoke of "The Agreement" the next day. However, the following evening Sarah poured us both a glass of red wine and after a few sips said, "So.... Are we going to discuss this anytime soon?" I could tell by the playful enthusiasm in her voice she was definitely interested in talking and quite possibly following through. "Sure," I said in...