Shemale Fucks Male Stories

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Orientation
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Infinite Scroll

Shemale Takes Her Man

by standingstones on Sep 12, 2017
Transsexuals & Crossdressers

I had just moved into a new town and a new job. A buddy from work said I should go and check out this club. Tom said it got a little kinky sometimes but that I would enjoy it. I tried to ask him what he meant by 'kinky' but he just smiled and said for me to go some weekend. I didn't really know anyone so I figured it couldn't hurt. That Friday I got dressed...

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....

Conditioning of a Scat Slave Pt. 13

by subtlesurrender on Sep 19, 2017
Fetish

The Ultimate Punishment Alone again in a bathroom; chained to a toilet bowl. At least this time Claudia had ample shit at her disposal. Almost the entirety of her load lay on the floor, as did the overflow from Shitface's diarrhea; which was in itself substantial. This time she wanted to savor the moment and avoid being left with nothing to do again. Let's...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Dr. Landry and Nurse Lisa

by newfield1981 on Apr 17, 2018
Transsexuals & Crossdressers

This story is a spin-off from the "Neighbors sissy son" series. Though it stands alone, it will eventually cross over with NSS. SPOILER This series falls in the transsexual crossdresser category for the first story. There will be very little in the way of men participating in gay sex. This series will sometimes revisit this subject. After that it will be ba...

Healthy Behavior

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

Yes, it's a new series, fans of mine. I know you like Marilyn, but she's on hiatus. Deal. Anyway, I do have something interesting for you. It's an unusual tale, but then again, my writing tastes have proven to be a bit unusual. I'm about as mainstream as N'Sync is underground. So without further ado, let's get started. Oh, and yadda yadda yadda over 18 to re...

Dark Life

by Samuelx on Sep 14, 2017
Transsexuals & Crossdressers

Kiara looked at herself in the mirror. She liked what she saw. A tall girl with long black hair and pale blue eyes. Her skin was light bronze. She stood five feet eleven inches tall in her bare feet. She had just stepped out of the shower and finished drying herself up. Kiara was a pretty girl and she could hold her own against most of the other females out...

Pool Party

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cun...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....