Shemale Dating Stories

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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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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...

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...

Girlfriend's Shemale Surprise

by Artvan1 on Sep 24, 2020
Transsexual

As Carter finished unpacking after dinner, he couldn't help but smile. His last summer before having responsibilities would be spent in the beautiful home belonging to his girlfriend's parents. Carter and Chloe had only been dating for a few months but were both entirely consumed in the early parts of their relationship. From hand holding to mini-golf the yo...

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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...

Tribal Ecstasy Ch. 01

by icemania on Sep 16, 2017
Transsexuals & Crossdressers

Denise pressed her hands as hard as she could over her ears as she tried to block out the low thunder of drums and the faint shrieking moans that had become her only companions. Her head still throbbed a little from the injury she had suffered in the car crash, but it hardly figured on her list of concerns right now. She had woken up here in this dark musty...

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...

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...

MarryYourFuta

by mimi1988 on Feb 21, 2018
Transsexual

**[Sorry for publishing the story without an ending, but I will try to do a chapter every day :)]- - - - - - ** Im a young boy, im 22 years old, i start living by myself and because of that im feeling lonely :( Im new in this town, and i have no friends here, my job suck (it's a callcenter) i need to meet new people fast because im going crazy. I found this...

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Leap of Life

by Iamherslut on Apr 22, 2025

**_(AUTHOR'S NOTE: This is my first story. I'm writing it as a form of exercise , so I apologize in advance for the amateur style. Please, if you like, or don't like, anything, leave me a comment. I will try to change things, but cannot promise. I'd love to hear what you all think.)- - - - - - _** Richard was balls deep in the bimbo's pussy. They were on a c...

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