Crossdressing Sissy Stories

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Inaugural Crossdress Sexfight Ch. 03.5

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

After losses to Tommi, Jaimie and Dani, it didn't take a genius to realize that I had become the defacto jobber of the Crossdressing Sexfight League (CXSFL). There wasn't a cock among them that hadn't been in my mouth or ass at some point and if we had kept standings, I would have been in dead last place. Unless I wanted to accept my jobber role within the l...

How Gerry Caught Me Crossdressing!

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When we're young, we can be extremely naïve! This applies to almost everyone, and it's my only excuse as to how Gerry caught me crossdressing so easily. I had paid for a room in the hostel where he worked as a caretaker, and expected privacy. It simply never occurred to me that he, or anyone else for that matter, would feel at liberty to intrude upon me on t...

Sarah was Trained to be a Girl

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I love to search on-line for sites related to crossdressing, that's how I found Literotica. I've also found sites for 'Men in Panties', videos of crossdressing, girls clothes for men, etc. One time, I was really lucky, I found a site offering a weekend of 'girly training'. We would be taught how to walk, sit and act like a girl. We would be dressed the whole...

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

A Fantasy Night Exposed Ch. 01

by tfrah on Sep 12, 2017
Fetish

This is the first part in a story based on my fantasies which my wife has long been encouraging me to finish writing and publish. In my defence this is also my first ever submission and the first time I've tried to properly finish a fantasy story so I'm also very curious to see its comes out purely self indulgent or if it actually works as an erotic story. I...

Chrissy Gets Caught

by femininechrissy on Sep 18, 2017
Transsexuals & Crossdressers

I don't even know where to start. I've been cross dressing ever since I was a young girl, I mean boy. I have always been jealous of women. They get to wear the prettiest clothes. They get to wear makeup and make themselves look beautiful, as if they weren't born beautiful already. I have loved wearing panties and bras and dresses and makeup for as long as I...

My New Family Ch. 03

by eagle166 on Sep 15, 2017
Transsexuals & Crossdressers

Lying in bed talking to my wife, Heather. Rubbing her large swollen belly, Heather is pregnant with twins. Things haven't gone as well as we would have liked. Yes we are still very much in love, so there is no problem there. But Heather is 8 months and 1 week into the pregnancy and with twins, she has been very uncomfortable to say the least. Rubbing her b...

Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

Sarah Gets to Write Her Own Story

by SarahCD on Jan 6, 2020
Transgender & Crossdressers

If you are an adult, looking for some kinky fun, live in the San Francisco peninsula and would like to star in a re-enactment of one of my experiences, contact me. My experiences here show what I like to do. We can write our own scenario and then act it out. I'd love to help you make your fantasy a reality. Now for my latest adventure, I found a Classified...

A Sissy Surprise

by nancyallen on Sep 16, 2017
Transsexuals & Crossdressers

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into the bedroom and stopped dead in my tracks. My boyfriend was on...