Sissy Shemale Stories

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Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

Filipina Cuckolds Her Sissy Husband

by nancyvasquez on Sep 14, 2017
Transsexuals & Crossdressers

If there's anything more sexy and exciting for a closeted sissy than dreaming about being a woman on your knees getting ready to serve a big black muscleman, it's actually having the balls to go out there and make it a reality. It happened to me! I was married, to a hot sexy girly-girl Filipina. When we got married I was still trying to be in denial about my...

A Sissy Surprise "The House Warming"

by Simply_Sissy on Feb 6, 2018
Transsexuals & Crossdressers

My girlfriend Vicki had been really pushing me to go to her friend Mary's house warming party on Saturday night. Mary had been quite the bitch lately not like the two of us ever really hit it off. To make things even worse she is aware of my panty wearing secret. Vicki had shared this bit of information with her when she first discovered my little fetish abo...

My Journey to Heaven

by Corina84 on Sep 14, 2017
Transsexuals & Crossdressers

How did I end up here? I couldn't believe what just happened! I was in a daze from what I just did. I was neither sickened or disgusted by it, I was just surprised that I had come so far. Here I was, on my knees with cum drizzling down my face. Something that I have fantasized about for years, but was never able to gather enough bravery to step out and try...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Dan's dreams come True Ch. 02

by JenniferTaylorTV on Jan 20, 2020
Transgender & Crossdressers

Caroline giggled with delight at the look on Jennifer's face. "She never had any idea, Suzanne. She thought you were a real girl!" Jennifer felt like crying. She was so excited, so turned on by the beautiful Suzanne, she couldn't believe what she was seeing. But there in her delicate silky panties was a hardening cock. Bigger than Jennifer's own not tiny ef...

Jennifer's New Adventure Ch. 01

by JenniferTaylorTV on Jan 28, 2020
Transgender & Crossdressers

Author's note: This can be read as a stand alone tale but it perhaps better enjoyed after reading Dan's Dreams Come True. Thanks too for the wonderful feedback. It makes working on these stories so rewarding. Jenniferxxx ------------------------------- Dan was woken from his deep sleep by a loud knocking on the door. He stumbled out of bed, grabbing his dr...

Crossdressing Playdate at the Lake

by montrealjane on Sep 16, 2017
Transsexuals & Crossdressers

At the end of the summer, I was lucky enough to have some playtime at the lake. I had been emailing and IM'ing back and forward with a girl that I had found on Craigslist. Craigslist is something of a lottery full of timewasters and scary people using many bogus identities, so it takes some time to filter out who really serious to get together and have fun,...

The Making of an Angel Pt. 02

by AngelLawrence on Jul 29, 2019
Transgender & Crossdressers

This is the 2nd stage of my biography of how I went from vanilla male to shemale slut. All persons are over the age of 18. *** I gulped. The close proximity of the woman and all the pretty lingerie in front of me was making me feel light headed. "What size are you?" She asked. "28" waist 38" chest" I replied. "No silly! What girl size are you?" she...

How I Became Sissy Willow Ch. 03

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

I slept on the floor next to the bed that night, still in the lingerie and sundress I'd worn the day before. Fern and Jason, of course, slept together in the bed. As I drifted off to sleep I kept thinking about the events of the evening. I had been put in women's clothes by my wife, Fern after she found a magazine I forgot to hide. The magazine showed a tra...