Shemale Mistress Stories

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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...

Small Cock Frustration

by jamtby on Oct 8, 2019
Transgender & Crossdressers

In 2007 I suffered from a severe medical condition which required extensive surgery. The procedure saved my life but the removal of my prostate, bladder, and extensive nerve damage left me without a functioning sex ability. My cock and balls remained outwardly normal but they were not doing what they were supposed to do. The relationship with my wife became...

Melissa's Ordinary Day Ch. 04

by Floydman1 on Sep 15, 2017
Transsexuals & Crossdressers

It had been a few weeks since Jessica had revealed to Melissa that they were transgendered female sex slaves. She didn't think of it that way, because she had been programmed to think of herself as a "shemale sex slave." It made her shiver with pleasure every time that she thought of it, and her nipples got incredibly hard. Nothing would do that to her cock,...

My Transformation into a Shemale Ch. 02

by jamtby on May 29, 2018
Transsexuals & Crossdressers

"We have a party tomorrow night and you are the guest of honor. My friends and guests will find you to be very attractive. You will need to make a few changes but I am the one driving them. Kyle will be my assistant and your trainer. "First, what do you know about shemale?" That question stopped me. I muttered nothing as I started to move my hands to cover...

Call in the Professional

by xploring96 on Oct 15, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, prostitution, Domination/submission, and derogatory terms used to humiliate. If this offends you please do not read any further. ***** How did Greg get here? It's election day in Washington DC and he is standing in the Ronald Reagan Airport with a big problem. To understand his problem it is important t...

Mia, Shemale Slave Ch. 02

by spitzharder on Sep 13, 2017
Transsexuals & Crossdressers

My pre naming party was held in the nightclub where Mistress Solange and many of her Shemale friends, performed. They sat at a private table but I had to stand as I was wearing a creation of Mistress Tia's. A spun sugar, almost gauze like confection held up only by the gold rings piercing my nipples and navel. The lime green bikini was almost transparent and...

Small Cock Frustration Pt. 03

by jamtby on Oct 8, 2019
Transgender & Crossdressers

Standing admiring my new look and getting to feel more comfortable with myself, the door to the garage opened. Carla called out, "Honey, I am home. Where are you?" Grabbing a towel, I wrapped it around my waist. "I'm in the master bedroom ready to take a shower." Carla entered the room and gave me a peck on the cheek. "How have you been this weekend?" she...

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...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Finishing School for Shemales

by Imogen_TS_2020 on Sep 25, 2017
Transsexuals & Crossdressers

Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outrigh...