First Time Sissy Stories

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From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Thrift Store Sissy

by sissywendi on Sep 16, 2017
Transsexuals & Crossdressers

A story by wendi marie st.clair She was looking at girl's blouses the first time He saw her. Of course, most of the world wouldn't have seen her as a "she" at the moment, but wearing her flare-leg, hip-hugging jeans that were obviously from the junior miss department and the androgynous purple t-shirt that showed that she shaved her body, she looked like a...

Pizza Delivery

by Spango on Sep 24, 2019
Transgender & Crossdressers

I could not believe that I was actually going to do it. I had been fantasizing about it for months. I was not really sure where I got the idea, but I had been watching a lot of sissy hypnosis videos online over the past few months, hoping to help release my inner girly girl, and perhaps the idea came from a scene in one of those videos. Anyway, it does not m...

Mistress Morgan's Sissy Husband

by corduroysissy on Dec 10, 2017
Transsexuals & Crossdressers

Morgan Ashley was a very pretty lady, not movie star glamorous mind you, but far prettier than anything her wimpy husband Robin would normally attract. Having just stepped out of the shower she was wearing a red mid-wale corduroy bathrobe and her long red hair was wrapped in a towel. She was seated in the living room armchair with a cigarette perched between...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...