Shemale Fucks Guy Stories

150,308 results
Orientation
Length
Source
Infinite Scroll

The Sexiest Shemales Ch. 02

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

Holly and I didn't want to waste our day so got up and got ourselves in the shower. We stripped off our g-strings that we were still wearing from our sex fest and turned on the hot water. We always shower together. Sometimes we will fuck each other in there or suck each other off but we just had sex so we just soaped up each other's bodies and cleaned the cu...

Shemale Shock Continues

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I met Cheryl at a party thrown by my sister. I asked Cheryl to come to my place afterwards and she agreed. That was where I discovered Cheryl was a shemale. I did something I had never done before. I sucked on Cheryl's cock and I took her load down my throat. After that I ended up fucking Cheryl's tight ass and giving her my own load of cum. We had now been...

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...

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...

The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

T-Girl Van Sex

by available269 on Sep 12, 2017
Transsexuals & Crossdressers

Pulling up to the curb near the bookstore one recent night, I happened to notice a nice looking custom van drive by very slowly. Looking intently at the driver as it passed by, I noticed that the driver was a very sexy looking woman, and she gazed at me intently as she passed by. The van pulled up to the curb in front of my car and parked. Shortly afterwar...

Punished in Paris

by maia24 on Sep 16, 2017
Transsexuals & Crossdressers

Maria the very pretty Irish transvestite had arranged to meet the men in Paris. She had agreed to be taken to a house in the suburbs to be punished, abused and sexually defiled by a number of men. She was dressed in a purple mini dress and wore very expensive lingerie. She was totally smooth and as she walked to the avenue to meet one of the men she was full...

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...

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

Open in Reader

Isekai Futanari Monster Girls

by G Man on Apr 10, 2019
Transsexual

t was 7:30 pm at the university. You and others were working on a particular project know the Metal suit although you can easily and quickly build it by yourself and make it ten times better than this piece of junk. But it was a team effort, and they pour their heart and soul into it. You can't just ruin the team effort. You were only assistance and pretende...

Open in Reader