Shemale Fucking Guy Stories

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Ex-Cellmate Looks Him Up

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

Everything was going to be perfect. Nathan hummed an upbeat tune to himself as he set the table. His girlfriend would arrive for their dinner in any time now. Nathan checked the food simmering on the stove for the second time in as many minutes. He heard a knock at the door. "Be there in a minute," Nathan called out from the kitchen. He quickly ran a comb...

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...

Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

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Blackmailed by a Bitch

by HarlanPilate on Sep 25, 2017
Transsexuals & Crossdressers

'I got it,' Laura said, running into the kitchen. 'I got the job!' That's great,' Dave said. He hugged his fiancée, full of joy at the news. Laura had been desperate to find a new job. Anything to get away from the place where she worked under her nightmare boss, Gloria. 'When do you start?' Laura's smile disappeared. 'As soon as I get my reference.' 'Fro...

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...

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...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

The Sex Star Ch. 01

by pinata on Sep 12, 2017
Sci-Fi & Fantasy

Priscilla awoke to the pleasant sound of a woman moaning in lust. She had been a lesbian all of her adult life, and the sound of a woman about to cum immediately made her juice up. She opened her eyes and looked around the room. There were several other women in there with her, and all of them were very attractive and completely nude. Most were still asleep...

Shemale Beauty: 1st Female Conquest

by silkstockingslover on Sep 13, 2017
Transsexuals & Crossdressers

Summary: 18-year-old discovers her powerful sexual persona. Note 1: This is the first of potentially many shemale stories starring the beautiful seductress Kara... Note 2: Thanks to... Tex Beethoven, Robert, and David for editing this story. Shemale Beauty: 1st Female Conquest Everyone has hobbies. For most people, hobbies can be activities like trav...

All the Way

by NearMiss on Sep 18, 2017
Transsexuals & Crossdressers

A different spin on the typical 'I got caught dressing up' story. I've always been fond of large women, not obese necessarily but you know, big. Like Amazonian big. Tall, big curvy hips and a chest to match with broad shoulders, but not in a masculine way mind you, but kind of proportionate for a girl. Let me tell you they aren't really that easy to come...