Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

First Time with a Male Ch. 02

by DarkAvenger49 on Sep 16, 2017
Transsexuals & Crossdressers

After her hair was rinsed, Travis squeezed the water from her hair. Then he wrapped a towel around her head and sat her back up. Before Travis unwrapped the towel from around her head, Mavis reached over and began to massage his crotch. "We have company, darling," Travis said, as Mavis continued to massage his dick through his pants. "Don't let me stop y...

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...

Hentai Heaven

by hornyboi666 on Sep 28, 2020
Fantasy

=============================================================================== Important notes: 1- It seems that I am not a good writer. as of now, I wrote 17 chapters about (John - North Korean 21 yrs old boy). I made an effort to make it a story with a sex scene in each chapter and build up a story. If you are in rush or not sure if you will like it or no...

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Rebecca's Secret Ch. 02

by Wannabe Chick on Sep 12, 2017
Transsexuals & Crossdressers

Synopsis: This story is partly based on fact, partly a fantasy. It is the story of a young man on vacation with his girlfriend and the night they have sex for the first time. The girlfriend has, up to this point, been reluctant to try sex. The big night finally comes for the two of them and the young man realizes, at last, what has made her so hesitant to sh...

Girlfriend's Futanari Secret

by freakyricky on Mar 26, 2018
Transsexual

I'm copying this story from here: https://www.writing.com/main/interact/item_id/1884280-Girlfriends-Futanari-Secret because I prefer the interface of this site. Please feel free to copy entries from the story map, found here: https://www.writing.com/main/interact/item_id/1884280-Girlfriends-Futanari-Secret/action/outline. In the original story, underage sex...

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Becoming Victoria

by Writer345 on Sep 18, 2017
Transsexuals & Crossdressers

Prelude. I was happily married and still am, but things have changed; or should I say that things have been changed - I have been changed. I was or rather am still wed to Anika, a rather dominating Polish lesbian, who married me for reasons of her own that are still a mystery to me. I'm not the man that I was...Oh, this is so confusing I'd better start at...

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...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...