Sissy Baby Stories Stories

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Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

Dark Maggie #03

by kneeler1138 on Sep 12, 2017
BDSM

Before she finally took me for good and all, my Mistress would send me panties. They were to 'inspire' me to write for her, among other things. She liked to remind me that I was still her servant, in spite of the fact that she was (at that time) a married woman, and I was in a relationship as well. Both her marriage and my relationship were so vanilla that...

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017
Fetish

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

House of Kinks

by royal22erick on Dec 24, 2019
Fetish

The house of kinks is almost as old as the oldest profession in the history of mankind, its creation was founded upon three unrefutable principles. 1- There will always be a market for the pleasure of the flesh and the house of kink always need to be in touch with the populace needs. 2- No House of Kinks manager should seek power at the detriment of the hous...

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Boredom and Therapy

by oldhippie1949 on Aug 31, 2017
Group Sex

The following is a true story. Naturally, all the names have been changed but all the events described took place just as I have written. If a bi-sexual threesome is not to your tastes then move on. If you are too young to be reading this, then move on. ***** I was so bored. Even my dog couldn't shake me out of it and. believe me, he tried. I didn't care t...

Cuckold Chronicles: Paul

by deltonaman2man on Sep 13, 2017
BDSM

Friday night is my night out with the guys. I go to a friends house and we have a small neighborly poker game. My wife likes the time alone, so she stays home and does whatever it is that she does. I don't get out much since my heart attack ( at the tender age of 48). I'm in my mid 50's now and we have been together for over 20 years. We are still very much...

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

Suddenly Sarah, A Different Tale

by grizzley123 on Sep 14, 2020
Fetish

Suddenly Sarah, A Different Tale ************************** This is an alternative Chapter 2 to the Suddenly Sarah story I wrote recently. It takes day number two with Sarah in a whole different direction. It likely helps to read the first story. The themes of this story are not for everyone, but for those that like submission I hope you enjoy. As always,...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...