Shemale Fuck Male Stories

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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...

Small Cock Frustration Pt. 03

by jamtby on Oct 8, 2019
Transgender & Crossdressers

Standing admiring my new look and getting to feel more comfortable with myself, the door to the garage opened. Carla called out, "Honey, I am home. Where are you?" Grabbing a towel, I wrapped it around my waist. "I'm in the master bedroom ready to take a shower." Carla entered the room and gave me a peck on the cheek. "How have you been this weekend?" she...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

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...

Tits Have Benefits

by hottchic on Sep 25, 2017
Transsexuals & Crossdressers

I thought that I would try to write an erotic story with a transgender theme as I have been a cross dresser for a long time. This is my first attempt at an erotic story with a transgender theme although it is not the first erotic literature I have written. I hope you like it, and let me know if you want to see more of the same. So here goes... * So there I...

Making Francesca Ch. 07

by Spango on Sep 16, 2017
Transsexuals & Crossdressers

After the glorious sex with Mistress Celia, Frank spent the rest of that day doing housework with Justin. His mind was all awhirl. To all outside appearances, Mistress Celia seemed to be the beautiful woman he had lusted after when she was a waitress at his favorite bar, but now he knew that underneath her clothes she hid a wonderful piece of man-meat. His n...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...