Shemale Fuck Guys Stories

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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...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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An Expensive Addiction Ch. 02

by NeverGuessWhatsNext on Sep 16, 2017
Transsexuals & Crossdressers

A week went by following my first encounter with English, my tranny escort, before I found myself craving another. Every day when I jacked off I thought of her sexy slender body and that big thick, long, uncut cock. The feeling of her hands running through my hair and then pushing on the back of my head to force her cock into my mouth...then the incredible s...

My First Shemale Sex

by available269 on Sep 26, 2017
Transsexuals & Crossdressers

I had developed a strong desire to be with a hot looking shemale for a long time. 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 wa...

Tgirl Fuck Club

by Dostoyevshe on Sep 16, 2017
Transsexuals & Crossdressers

Head spinning, I stumbled into an alleyway and landed behind a nearby dumpster. I'd had a few drinks, and some ecstasy. I'd told my friends that I'd had enough for the night, called a cab, but once I was out of eyeshot, zipped back towards an infamous gay club id been dreaming about ever since I'd heard rumours about exactly what goes on inside. Like a fly...

Erotic Adventures of Brandon & Cheryl Ch. 03

by timewarp69 on Aug 31, 2017
Group Sex

At this same time, Cheryl and Tommy had finished their 'session' and Cheryl was hanging out on the second floor balcony out back, bullshitting with some old girlfriends and having some drinks. "So, how's Mark?" Asked one of her friends. "Oh, I dumped him a long time ago." Replied Cheryl. "The asshole thought he owned me." Another friend of Cheryl's said...

Sex Toys and Websites

by Equinella on Sep 14, 2017
Fetish

I didn't tell my girlfriend that I was moving out; just packed my stuff and disappeared while she was at work. There was no need to say anything. After weeks of sleeping on the couch she wasn't going to miss me. My new apartment was furnished so the move mostly involved traipsing boxes up the stairs and finding the right shelf, cupboard or drawer for their...

Pounded Into Submission Ch. 02

by Jamesjones52 on Sep 12, 2017
Transsexuals & Crossdressers

*This is the prologue that leads up to Joe being "Pounded into Submission". Also, I read the comments about this being a repost. It is; I am the lonejackman. I got rid of my yahoo email account and couldn't get my password reset for here. * Two days ago Joseph was checking out porn like he usually did at his favorite site xhamster. A couple of BBW vids here...

The Sexiest Shemales Ch. 01

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

When I wake up in the morning, I wake up next to the sexiest shemale in the world...right after me, of course. I woke up this morning next to Holly, my beautiful shemale girlfriend. She was still sleeping in our big bed. The sun was shining in on our bed with our white sheets and white comforter. She was naked of course, except for a bright pink g-string....

Since that day....

by Ssrd33 on May 5, 2019
Transsexual

The weekend I finished and my whole body felt heavy, my ass felt more open and empty at the same time, I slept all the rest of the day. The next morning I woke up and had Melany's penis full of milk, I took it out and I felt that my mouth was very sticky, I went to the bathroom to take a shower because I could only smell the semen all over my body. When I ge...

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