Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

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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Friendly Seduction

by doomsparkle on Dec 11, 2019
Erotic Couplings

There are many beautiful women in your life. Some are taken and some are single, but all of them are there to be seduced! You (Will) - A mid-twenties office worker. You're a typical geek, but with enough social intelligence to not constantly creep out everyone you meet. Your house is the typical place your friends meet up to hang out. You began lifting weigh...

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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...

A fiery Tgirl adventures on tinder

by Yelawolf on Mar 20, 2021
Transsexual

You pose in red leather pants and a spicy matching crop top. Your pink nipples on full display as the timed camera winds down. The bright flashing light caught you in full sexy tgirl mode. You look over the snap shot happily. The picture shows off your slender pale stomach. The leather pants highlighting your long legs. The top, you knew, would play with guy...

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Girlfriend Trouble

by lovelymess212 on May 29, 2019
Fantasy

You've been dating Sam for a long time, even thinking of popping the question sometime soon. She's perfect in every way, and its near your second anniversary. You have your own apartment together, living with each other to count on. Maybe life is far from perfect, but you have each other. Of course, sometimes life throws you a curve ball. You wake up one mor...

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Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...

Marla Makes My Wife Ch. 01

by JTKetcham on Sep 14, 2017
Transsexuals & Crossdressers

I'm kneeling on the edge of the bed, my stocking-clad wife moaning in ecstasy as my shaft moves in and out of her cum-filled pussy. I watch her breasts jiggle in time with our sex. But what's really driving me mad is the feel of a hard shaft of flesh moving in and out of my ass, complimenting my movement in and out of my wife. I can also feel full breasts pr...

Shemale Devil in Disguise Pt. 02

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

Mid-June 2018: About a month has passed since I went back to my parents for work and about 2 weeks went by since I went to that party where I first met Rebecca. Since then, not much has happened because I wanted to distance myself from the group. Although I try to see them as least as I possibly can, I still want to get the gossip from my girlfriend in order...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

Mark's Surprise Ch. 1

by Kip Carson on Sep 13, 2017
Fetish

Mark had just broken up with his steady girl, Diana 2 weeks before. He was finding it really hard to get over her. They had been dating for almost 2 years, and he was devastated when he caught her in "The Act" with 2 guys from the football team. He saw her car at the hotel, and pulled in to see what she was doing. He stood outside the motel room door, and co...