Male On Shemale Stories

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Orientation
Length
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Infinite Scroll

SheMale Sirens Ch. 02

by WhiskeyIsGood on Sep 18, 2017
Transsexuals & Crossdressers

Chapter 1 has received good reviews, so here is part 2. Part 3 is still being written, but it is going to have more back round info on the Siren's, and a few more characters as well. Should be up soon after this one. Whiskey ***** The day I first decided I had to leave my home in New York was the day I turned eighteen years old. I was tired of everything,...

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...

The Sex Star Ch. 08

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

When Kayla woke up, it wasn't in the department store fitting room she had fallen asleep in. She was in a white room filled with bright flourescent light, almost like a hospital or something. She tried to get up, and realized she had been immobilized... leather restraints bound her wrists and ankles, and another, larger strap encircled her torso just beneat...

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...

Purgy's Birthday Blowout Ch. 01

by rikkusguardian on Sep 13, 2017
NonHuman

Purgy is the (c) of :iconmatthewbrandon: Vipra reference is the (c) of :iconVipra: Story is (c) :iconrikkusguardian: This story contains one of my new found love of condom filling/popping! X3 I always wanted to read/see more condom inflation, but there isn't much here, at least not at the levels i like it....so i decided to add it to this story and leave...

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...

Addicted to Pream's Cream Pt. 02

by Vodka_Jim on Sep 26, 2017
Transsexuals & Crossdressers

Author's Note: I'm sorry it took me so long to complete Chapter 2 of this story. I plan to be more regularly submitting stories. I have a couple more in the works and then will probably come back to the Pream story line. I hope you all enjoy. I welcome your comments. *********************** My heart is beating so hard in my chest that I can almost hear it...