Sissy Party Stories

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Orientation
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Infinite Scroll

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...

Sammi Meets Teddy

by Sissy_Sammi_ on Dec 8, 2017
Transsexuals & Crossdressers

Ever since Sammi was born Sam had been working his ass off, both in pants and panties. His grades in school improved rapidly as his outlook on life improved, and before he knew it he had sent away college applications and received acceptance letters. He knew where he was going to college, and before he knew it he was graduating. The rest of the year coasted...

My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...

Mistress Aimz

by hyperpress on Aug 17, 2017
Fetish

Mistress ordered me into my chastity device. I complied. "you may not cum this week," she told me. I didn't. I was good. I used depilatory cream and removed all my leg, clit and pussy hair for mistress. It was Friday. She told me to take off my chastity and jack off into a glass. She said I could cum as much as I want Friday and Saturday, but to cum in th...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...

Aunty's Toys Ch. 02

by novelcriss on Mar 25, 2019
Fetish

**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!** ***** Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she'd told him to call her had sent him a text. "Simmy dear, don't forget your app...