Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

Bill & Claudia Ch. 02

by KirkEdwards on Sep 16, 2017
Novels and Novellas

Bill and Charmaine chatted on the way back to their motel; as though they'd been lifelong swingers. The pleasure of being with another man wasn't new for her but it was an experience he'd never forget. Both of them were cautious with their conversation though she fumed inwardly since he'd been with another woman. Funny how she could excuse or overlook her...

A Shemale Vacation Ch. 03

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we'd been in a sticky situation before on this trip, sticky particularly for me rather than the others, when we'd found we had no money in the Amsterdam brothel, bu...

Friends with Benefits

by KittyandBear on Sep 13, 2017
Transsexuals & Crossdressers

It was late Saturday evening when Dave and Eric, shuffled home to Dave's place. They were returning from a party at the campus pub and were slightly inebriated. Eric had never fit in with the popular, party-going crowd in high school, but now hoped it was different in university. Dave had a nice apartment off campus, and Eric enjoyed the freedom of hanging...

Marilyn at the Movies

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

So, after about a bit of a hiatus, the shemale that you love is back. Well, at least I love her. After all she is an alter ego for me. Now if I could parlay that into some cash, I’d be good to go. Anyway, it’s good to be back in the saddle, especially the way college has been getting to me. This story, and the next few I plan on writing, will be stroke stori...

Lilith's Emporium Pt. 13: The Dark World

by maestro84 on Sep 12, 2018
Erotic Horror

Hello, this story and the next few chapters will feature the Rak-Sasha's character again, please go and check out her stories when you can as she also provided input for these. Thanks! ***** It was dark as the dust storm blew across the ruins of New York. The buildings falling apart after years of neglect. Patrick thought back to almost a century ago when...

Five Shades of Desire

by arachnophile52 on Sep 17, 2017
Erotic Couplings

1: Inscrutable In Kyoto, the cherry blossom season is in the early spring. In the first half of April, Maruyama Park is the favorite spot for cherry blossom parties. The centerpiece of the park is a tall shidarezakura (weeping cherry tree) which is lighted at night. During the autumn, the park is famed for the brilliant reds, yellows, and oranges of its fa...

The 21st Birthday Party

by WhiskeyIsGood on Sep 19, 2017
Transsexuals & Crossdressers

To say it was a wild night would be an understatement. My 21st birthday was literally, the greatest birthday of my life. Of course, the best part of the night had been meant only as a prank that my friends wanted to play on me just for the fun. No one, not my friends and definitely not me, had expected it to go in the direction it had, but to this day I'm gl...

First Cum, First Serve Pt. 02

by dreadknots on Jan 23, 2019
Sci-Fi & Fantasy

A sequel! This one has transformation of not just a gal but also a boy! If you don't like femboys and shemales might as well turn around at this point cause there's gonna be dicks, let me tell ya. Oh, and the standard cadre of weird fucking perversions: lactation, mind control, transformation. You know: totally normal things to get a boner over. Enjoy! **...

The Handyman is a Real Handy Woman

by SugarandSalt on Sep 19, 2017
Transsexuals & Crossdressers

"How does it look?" My girlfriend spun around, asking how I felt about her new dress. I hadn't gotten this far in our relationship by always telling the truth. "It looks great babe." I could see the reflection of Bridget's frowning face in the mirror. "You don't think it makes my ass look big?" I wish it had. What man truthfully prefers a small ass? I...

The Blackmailers Fall Ch. 04

by NiceNastyMann on Aug 30, 2017
Fetish

Note – this follows immediately after the end of chapter three, The Blackmailers Fall. I was just going to let the story end at part three – but then I realized that this story could end in a variety of ways. The last chapters are some of those endings. This one is what I like to think of as the 'happy ending'. Enjoy! Donna seeks out Robert and his massi...