Shemale Fucks Guys Stories

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Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

Chemical Flavor

by Miles63 on Sep 13, 2017
Transsexuals & Crossdressers

Introduction: Sorry that it's taken so long to upload a new story. I've been sitting on this one for nearly a year as I loved the beginning but hated the ending. So after a big deletion and a big re-write I now like the ending. I've been just mentally drained for awhile and no story was coming to me, but now finally something to upload. Any errors please be...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Male or Shemale, Still a Slut

by yeaimbored on Sep 11, 2017
Transsexuals & Crossdressers

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone...

Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

Becoming Victoria

by Writer345 on Sep 18, 2017
Transsexuals & Crossdressers

Prelude. I was happily married and still am, but things have changed; or should I say that things have been changed - I have been changed. I was or rather am still wed to Anika, a rather dominating Polish lesbian, who married me for reasons of her own that are still a mystery to me. I'm not the man that I was...Oh, this is so confusing I'd better start at...

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.....

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Danielle Ch. 06

by sexgundam666 on May 27, 2019
Sci-Fi & Fantasy

"Come on! It's my turn!" Casey whined. She leaned against the bathroom stall, watching and stroking herself to the scene before her. "Sorry, ahh, it's so good," Holly answered from her prized perch, though she didn't move from it. A train of complaints and insults danced between them, all while the albino bounced, swayed and clapped her body against a might...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...