Shemale Friend Stories

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Infinite Scroll

College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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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...

Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Shemale Devil in Disguise Pt. 01

by Chomedey on Jan 20, 2020
Transgender & Crossdressers

This story talks about how a charming shemale I thought was completely harmless practically stole the love of my life and my honor. It's May 2018. I just finished my third year of University. One more year of school and I graduate with a degree allowing me to enter the job market. This summer after passing my exams, I was planning on staying at my parents...

My Wife, the TOP ONLY Malay Shemale

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

Hi all, my name is yarra (not my real name perverts!!) and I am a proudly married matured male, now 57 years old. My wife, 52 is a (or was a) biological female technically, been married to me for the past 24 years. Let me tell you my fantastic and totally out of this world story. Flashback to 24 years ago, that is the 1989, when i just reached my 30'ish a...

A Secret Fetish Ch. 01

by margekershaw on Sep 13, 2017
Transsexuals & Crossdressers

When teaching a section of my favorite class, "Modern Erotic Literature", I noticed a guy in the back of the room acting strangely. He was in obvious discomfort, and I wondered why. It was during the lecture where I discuss fetish stories. Students find it a revelation. The first thing I usually do is define "shemale" tales: " 'Shemale' is a hardcore adu...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Classroom suprise

by william125 on Mar 10, 2015
Transsexual

A recently qualified teacher, today is your first day at Tower sixth form college. You stand at 6' 2" and keep your self in good shape. On your way in this morning you saw a group of girls giggling and looking at you. Obviously talking about the new teacher. The bell rings and a little nervous you welcome in your 18 and 19 year old students. Note to r...

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