Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

The Boutique

by Myrmidon69 on Apr 18, 2018
Transsexuals & Crossdressers

Sharon Ralston straightened the sweaters on their hangers, making sure they hung evenly and in alignment with each other. She was moving slowly along the racks, tidying a little here, picking off a loose thread there, while keeping an eye out for customers. The boutique was fairly quiet at the moment, with only a few customers browsing through the items on d...

The Thorned Rose Ch. 02

by XtinaSmith2017 on Sep 13, 2017
NonHuman

Authors note - Chapter subject picked by a raffle winner <3 I wasn't sure whether to tag this as Trans or non-human, I went with non-human just to try and warn people who wouldn't like the content below not to read it! So if you don't like elf boys taking it from shemale nagas, skip this one! Mwah, Xtina Xx ***********************************************...

Oops, I Did It With Britney Pt. 04

by britneyfan on Sep 14, 2017
Celebrities & Fan Fiction

6. I'm A Slave 4 U We were both still a little sticky from the sweat and cum of our hot, passionate sex together, so Britney led me through to the massive en-suite bathroom that led through from her bedroom. The bathroom was decorated with the same height of expense and taste as the rest of Britney's suite and the huge shower was easily big enough to fit th...

The Law of Attraction Ch. 06

by hottchic on Sep 17, 2017
Transsexuals & Crossdressers

This story is a transsexual fantasy. Before reading this chapter I highly recommend that you read chapters 1 to 5. The first four chapters of this tale were told from the prospective of James/Jamie who started out as a shy cross dresser. This is the second chapter to be told by Ashley a hard core lesbian who becomes attracted and eventually falls in love...

Bill & Claudia

by KirkEdwards on Sep 14, 2017
Erotic Couplings

(excerpt from book) * The meaning of art * Bill had a hard time seeing the paintings on the walls since they were in the shadows. He could tell they were of an erotic nature showing naked subjects in different poses. Lois noted he was taking everything in and asked if he'd like to stroll around in order to get a better view of the art saying she'd like to...

Tight Spot

by XtinaSmith2017 on Dec 26, 2017
Transsexuals & Crossdressers

Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavour but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way towards the shop as a group, "Aw come on Cody!" one of them jested, "You aren't a...

Southern Nights

by jjjshmidt on Sep 16, 2017
Transsexuals & Crossdressers

Robert couldn't believe he had done this. He was sitting in his room at a well-known tropical resort famous for its promiscuity and lack of moral behaviors. Just 12 hours ago, he had packed his bags, hopped into a cab and boarded a plane heading south. His friend who worked at a travel agency had planned the trip for him and told him to get away for a while....

New Moves for Hubby Ch. 02

by ndeavour on Feb 12, 2019
Group Sex

[Author's note: Thanks go to Mumbo700 for helping to shape this story. Her work can be found here on Literotica as well.] *** You may have read the first story in this series - my wife's account of the things that came to a head (pun intended) in our bedroom, with her friend Jayne and a couple of strap-ons. I'm not denying any of it, nor am I going to try...

Made to Obey Ch. 06

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Twinsies Pt. 02

by Skylar_Macy on Feb 4, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Hello, everyone. I hope you all enjoyed how everything began. Here is a small story on my first real encounter and a discovery I never expected. *** It happened a few months after I had my special night with my twin sister June, and her two friends; Sarah and Amber. The night my...