Trans On Sissy Stories

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Orientation
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Infinite Scroll

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

Mamma J Ch. 01

by Transbabe55 on May 4, 2020
Transgender & Crossdressers

"Mom, what am I going to do about Jason?" My daughter sat facing me seated at my kitchen island with a troubled yet familiar look upon her face. It was the same look I'd seen when she was doing poorly in a class or when one of her friends slighted her. The circumstances were quite different this time, however. She was thirty years old and had just found...

Teen Boy Becomes a Girl for his BFF Pt. 03

by SissyKelly on Dec 5, 2017
Transsexuals & Crossdressers

I was fucking stressed. After fucking me in the ass and filling me with cum at his house, then cumming all over my face at the tree, me and Ryan hadn't had another chance to hook up in weeks. Sure, we still texted and exchanged photos and jerked off to each other like crazy, but since my parents divorce that was harder to do as my mum gave me little privac...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

AliExpress and Sissy Downfall Pt. 02

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was a...

A Week End with Mistress Pt. 04

by gasissynora on Oct 8, 2019
Transgender & Crossdressers

This is a continuation from part 3 of this series. To understand what is happening you should read the previous parts of the story. I hope you enjoy this and would welcome your comments. * Mistress Nikki grabs our hands and leads us to a room behind the stage. There are some lockers in the room, a bed, some bondage equipment and other kinky paraphernalia....

Sissy Dust Pt. 03

by Sissyhalo on Sep 11, 2018
Transsexuals & Crossdressers

*Before... I lose track of everything after he seeds my insides and kept going. No not everything. Three highs after the mixture entry affected me. Three times Steven came inside of me. I dimly remember the clock. And my body in some sort of perfect fuck shock after he was done and shaking with him vibrating too our hearts pounding after that and him s...

From a Husband to a Dutiful Sissy Ch. 14

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Going to a Rock Concert and Something Very Special. Mikel and I had a wonderful Christmas and New Years. Helen and Alan both like him a lot, find he is a solid citizen and man. Helen sees how Mikel lights my life up, fills my heart with love and joy. She hopes for a better future together but warns me to be careful so as not to get too far...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Mistress Jade

by AudibleRaines on Mar 30, 2020
Transgender & Crossdressers

Part I -- Dread and Desire Aaron stood at the door in the silent, faintly lit corridor of the condominium building where he'd been directed. Having knocked and waited several minutes, he contemplated turning to escape the uncertainty, to escape his racing pulse, but his legs would not respond to his inner message to retreat. It had been several weeks since...