Shemale Girlfriend Stories

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Orientation
Length
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Infinite Scroll

Chen

by spitzharder on Sep 14, 2017
BDSM

Chen, a beautiful, olive skinned, Israeli, Shemale was the owner manager of an underground club called 'Weals and Squeals', which encapsulated the nature of its customer's interests. The lesbian clientele were of all ranks and walks of society, the fees were high but then so were the scale of desires. A lesbian mistress used to bring a nubile naked young...

The Slave Traders Pt. 03

by jamtby on Jan 23, 2019
Transgender & Crossdressers

Exhausted both physically and mentally I got into bed. It was then that I noticed my breasts were tingling. A strange sensation. I felt totally humiliated especially having the woman I love forced to watch me being masturbated by a man. She must have lost all respect for me. I also wondered what hell Carla was going through. The constant threat of having her...

Shemale Devil in Disguise Pt. 03

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

This story is the continuation of Shemale devil in disguise, part 02 Mid-July 2018: About two months have passed since I went back to my parents for work and almost a month since me and Joel decided to do some investigation about Rebecca. Okay, I'll admit, we didn't find too much. We both added her on Facebook but she never accepted the friend request. We d...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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Making Francesca Ch. 01

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: I originally posted this story on another site under the title "Kidnapped and Sissified" a few years ago. I have decided to pull it out, dust it off, do a little editing, slap on a new title that I like better and share it with you fine folks here. Enjoy. Frank was an ordinary guy in his mid-twenties; of average height and build, loved col...

Shemale Adventure Ch. 1

by girlboybootsie on Aug 18, 2017
Fetish

You: early 20's, tall boyish good looks with a lean and muscular body. Dressed in tight leather pants, from behind your tight buns are revealed by the shiny black leather, as are your cock and balls from the front. You are wearing black leather boots and a denim shirt that refuses to hide your strong broad shoulders. Me: early 30's, tall, blue eyed, consid...

Create a Shemale

by wsauthor on Sep 29, 2018
Science Fiction

*Author’s note: This story is Public, if you have an idea, start writing!* Robots, science and chemistry have all advanced further than the public is aware of. Due to patents and trade secrets, nobody knew it was even possible to create a sex bot. They can have gravity defying shapes and sizes. They can even alter their owner with chemical cocktails. Cockbot...

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Jabba's Shemale Slave Pt. 02

by mkh78 on Oct 8, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return of the Jedi. I have used Huttese words in some parts. These are not of my own. *** 1:30 am. Tarno and the Twi'lek shemale prostitute he found and subsequently bought from the brothel's owner, were now quickly speeding across the Tatooine desert. He considered spending the night at a...

Pam's Shemale Experience Ch. 05

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

"Take it, slut, right down your throat!" "That's right, take it, fuck yes, choke on it!" "Fuck yes, babe, that feels so fucking good!" Pam swooned, kneeling subserviently as her temporary owner took her pleasure. "Fuck, Pam, your throat feels so good!" The lustful shemale was as usual in total control. One hand had a fistful of Pam's hair, while the oth...