Sissy Samantha Sex Stories

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Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

My Wife Turns Me Out At Book Club

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been 3 days since the event, and my mind is still reeling. I can't believe my wife took me as far as she did in one night. Sharon had told me a few weeks ago that the neighborhood book club she attends was having a special couples night. Apparently the wives had discovered that their husbands enjoyed the idea of group sex and partner swapping, and eve...

The Vixen

by TheEroticProspero on Oct 11, 2017
Transsexuals & Crossdressers

Simon first saw her as he walked through one of the rougher streets in town. He couldn't help but stare at her long red hair, sharp facial features, milky white skin and the tight velvet jacket she wore over an even tighter leather dress. He looked her up and down, admiring her modest but perky bust, her thin but shapely body and her simply perfect legs. Si...

Darling Nikki Pt. 02

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1 - The Morning After The next day, Nick awoke thinking it was just a really messed up dream. When he got out of bed and found that Samantha had unlocked and removed the dress, panties and shoes, but everything else was still on, he was pulled right back to reality. He looked in the mirror on his wall and saw that he was standing there in a very tig...

Stroke Slut: Goddess' Cuckold

by StrokeSlut on Oct 19, 2020
BDSM

"Well don't just stand there drooling on the doormat, come on in." The black hood had come off Stroke-Slut's head, the sudden burst of sunlight that hit his eyes was nothing compared to the radiant beauty that stood before him. Despite hours of jacking off to her on the internet, not the mention their previous sessions, he never seized to be amazed at the si...

Samantha's Panty Boy Ch.02

by PinkPantysBoy on Sep 13, 2017
Fetish

Special thanks to Angel Love for editing. Samantha opened the front door and slammed it hard so Jack would know she was home. He had drifted off to sleep with his pink panty still on and her panty crotch on his face. He heard the door shut and immediately got up. He heard her coming up the stairs and did not have time to change back into his own underwear s...

Counceling

by seeingifthismakessearchwork on Mar 2, 2020
Transgender & Crossdressers

****** Forward: This story is an expanded version of a story I read and with the author's permission I revised and added to it. ***** Dr. Lidia Vega let her eyes briefly dart to the clock on the wall. Her newest patient hadn't said anything for nearly ten minutes, but that's okay it was his process and she was only here to lead him through his grieving. S...

Reversals Ch. 12

by RachelClark on Sep 18, 2017
Fetish

Samantha Comes to Dinner Eric's eyes went wide with dread as he stared towards the front door and froze. The very idea that somebody other than Julia would see him wearing nail polish was completely paralyzing. "Well, what are you waiting for? Open the door for our guest," Julia said firmly. He started walking to the door, the panic making his hands tremb...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Mistress Sharon Pt. 01

by corduroysissy on Sep 5, 2018
Transsexuals & Crossdressers

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses...