Mtf Crossdressing Sissy Pussy Boi Slut Prostitutes Stories

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Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

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...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Work Day, Fun Day

by manatdawnrise on Mar 28, 2018
Transsexuals & Crossdressers

Showering for work, I look down at my chastity bound cock, still struggling to come to terms with the events of the weekend. A sense of relief washes over me. The relief found when a lifelong secret had been broken. I was no longer wracked with guilt of my crossdressing dark side. No, I was now liberated in mind yet bound in a physical sense. My wife had a p...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Daddy's Little Sissy Diaper Slut

by Satanicsissybitch on Jul 14, 2020
Transgender & Crossdressers

I absolutely love wearing my adorable pink pull-ups for Daddy and I really love being his cute little sissy diaper slut! Daddy had always loved playing the dominant role with women but it was me who has him addicted to sissies and I've always been a little diaper slut. Well, a pull-up slut anyway. I always felt the adult diapers were not only boring and blan...

From Kyle to Kyla

by justsomefantasies on Sep 14, 2017
Transsexuals & Crossdressers

It was Sunday afternoon, and I was staying at my girlfriend's apartment. She had asked me to stay there to spend the week-end to take care of her fishes while she was away. We've only been dating for about 3 months at the time and she had no idea of my crossdressing ways. Of course I went through her clothes. I had on a black thong and a matching bra. I was...

A Little Twist Over the Road

by mdw_dark_angel on Sep 17, 2017
BDSM

Master is an OTR driver for a national corporation. That could make things very difficult for O/our relationship as W/we would not be able to see Him very often, for very long at a time, except that - sissy, affectionately known as pet, and angel, referring to this girl - are His relief drivers. W/we travel with Him everywhere so it makes life a bit more exc...

Another Submissive Slut Ch. 07

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

Getting ready to go anywhere was beginning to take more and more time. Cleaning myself properly just encase I encountered Ms Shawna or Mr Lennie during my excursions entailed various time consuming activities that a well presented sissy just couldn't ignore. I viewed my naked body in a full length mirror searching for flaws. I now kept myself smooth, hairles...