Shemale Dominates Guy Stories

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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...

Just Another Story

by neoview on Oct 15, 2017
Transsexuals & Crossdressers

Once upon a time... "Wait, wait, wait! We're not actually starting the story like this, are we?" Said the short fat kid in his mid-twenties. "I'm neither short nor fat." He said while swallowing his stomach and lifting himself on his toes. "I'm not doing any of that. STOP GIVING THE READERS FALSE INFORMATION!!" The angry non-short, non-fat kid yelled. "H...

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...

Amanda and Me Ch. 01

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception. As I w...

My Shemale Mother

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is... I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I...

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...

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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First Shemale

by mac053 on Apr 27, 2020
Transgender & Crossdressers

Lately I've been thinking about sleeping with a shemale. I'm in my late 60's, look 10 year's younger and, for some reason, I'm really attracted to shemales. There are a two LGBTQ bars in my area and I found one that I thought might work. I had no idea what I would do once I got in the bar, but this was an itch that I had to scratch so I went for it. When I p...

Making Francesca Ch. 01

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: I originally posted this story on another site under the title "Kidnapped and Sissified" a few years ago. I have decided to pull it out, dust it off, do a little editing, slap on a new title that I like better and share it with you fine folks here. Enjoy. Frank was an ordinary guy in his mid-twenties; of average height and build, loved col...

A Shemale Vacation Ch. 01

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was s...