Shemale Dating Sex Stories Stories

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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...

First Time with a Shemale

by BigAndy922 on Sep 13, 2017
Transsexuals & Crossdressers

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favours. I liked my share of porn, and as I had...

Hooking up with a shemale

by Gliorna on Apr 29, 2025

You are Blake Tallbrook, a semi wealthy man living alone for the moment after a break up a year ago. You have been working hard for the last year just focusing on your job. Your Sexual life has been normal one night stands with random girls from bars late at night. But you have become interested in something else. A girl with something special. You have look...

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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...

SheMale Sirens

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

Of the many mythological creatures invented in the mind of man over time. Some are believable, while others are known to be simple stories created to scare people with weak constitutions or to frighten children at bedtime. Werewolves, vampires, demons... all such creatures are what I am referring to. But the one myth that I had never heard of as a child was...

A Night with a Sexy Shemale

by MajesticLVR87 on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story which goes deeper into my explorations of my sexuality in my younger years many people may not have the guts to share so much about their past I don't have that problem because I have met the love of my life and plan on sharing the rest of my life with her my adventures with other partners or random partners is over I have settled down s...

Mikes First Transgendered Pt. 03

by SamanthaMeyers on Nov 16, 2020
Transgender & Crossdressers

Please read 1 and 2 before this one. Mid October has set in and once again I am leaving work later than usual. I am in the parking lot speaking with co-workers when my phone rings. I recognize the number as being from the restaurant Sara works at. I answered and hear her voice on the line. Sara Says, "Hi Mike. How are you?" "I'm good Sara. How are you?" I...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

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,...

Mikes First Transgendered

by SamanthaMeyers on Nov 16, 2020
Transgender & Crossdressers

This is an absolute true story. Mike loves transgendered I had just turned 30 and was about 1 year out of my divorce. I was dating a Filipina lady named Mika who was not the best person for a relationship, for many reasons. During our relationship Mika used to take me to this Filipino dinner restaurant which had food and late night live musical shows. Duri...