You Are A Sissy Stories

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Infinite Scroll

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

It's Another Family Tradition

by Canadagander on Sep 13, 2017
Loving Wives

Copyright © 2004. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - -- - - - - Writer’s Note: This piece is a sequel to the previous story of Sam and the Powell women entitled “It’s A Family Tradition.” If you haven’t already read that one, I recommend that...

Sissy Maid to Be... Ch. 01

by missjennymaid on Sep 5, 2018
Transsexuals & Crossdressers

Prolog I have always had the desire to dress like a girl. It started at a young age when my mother used to have me try on dresses to "see if they would fit my cousin." As I got older I still had the desire and it got strong enough that I started going out in public in college. I was lucky enough to meet and marry a woman who was accepting of my "hobby". Liz...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Sissy Panty Handjob

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work. Still hard I jumped out of bed immediately a...

Sissy Sisters

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

This was the letter I wrote to an older Sissy in an attempt to convince Her to accept me as Her littler sister and use me. * Stop, You make me blush. I too luv wearing feminine luxurious things. I believe now I need to wear sensuous feminine things under the direction of some one else. Could that possibly be You. Please. You would treat me like a little...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...