Gay Sissy Stories

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The Transvestite Divorce Transcript

by desireethtttv on Aug 1, 2018
Transsexuals & Crossdressers

We begin with the plaintiff, the woman of the marriage of 33 years, from hereto within known as Mrs. S. Verses the transvestite husband we shall call Desiree. Mrs. S Attorney (referred in future testimony as AFM: Please state your reason for the divorce proceedings, if you please Mrs. S. Mrs. S: I wish to divorce my gay transvestite husband due to the lack...

The French Trip Pt. 01

by DrLuverotica on Sep 16, 2017
Transsexuals & Crossdressers

We'd only arrived in the South of France late the night before, but already Jo my sexy, blonde 40 year old wife was gagging for it. We were driving along a fairly quiet road populated by overhanging trees with the Pyrenees providing a dramatic backdrop. Jo was dressed in a short blue skirt, white button down top which was undone giving me a very distracting...

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Caught In the Act

by secretanon on Sep 12, 2017
Fetish

Please read the previous 2 stories before you read this if you want to know a bit about the characters! They follow similar adventures if you enjoyed this and the story flows better. Thank you! ***** Once I had developed a friendship with a fellow panty boy, things started to get fun. I don't have anyone else I can talk to about wearing panties. It felt ex...

My Week with Laurie

by robbie3 on Sep 14, 2017
Fetish

Laurie was a co-worker who had recently been appointed the training officer in our government agency. As such, she had acquired a nice private office, in which I found myself spending more and more time. We had always been friendly, but lately were exchanging comments of a more personal nature. I'd call it meaningless flirting. Laurie was a year or two young...

I"M Not, Really, I'm Not

by gbr2004 on Sep 14, 2020
Fetish

I'm finally getting settled in my new place. I have just moved to LA from Kansas a couple weeks ago and had been set up in an apartment by the sales office at the advertising agent who had hired me right out of college. I was so excited to be in a real city and it was so much different from the rural area I had grown up in. College had been fun and I had don...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Spanking Night Ch. 07

by Angelscuck on Sep 14, 2017
BDSM

The shower felt good against my freshly shaven skin. I was covered with cum, urine and pussy juice. I knew if I took too long, I would be punished by my wife and mistress so I cut it short. After towel drying, I put on a clean pair of my wife's panties and hurried down stairs. "Well, here's our little sissy bitch now. It took you long enough!" Mistress Sh...

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...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...