Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Daniel and Jamie's Romantic Night Ch. 02

by lockedinsteel on Apr 17, 2019
Group Sex

Daniel woke up and realized that someone warm was pressed into his back, their arm draped over his side, their face nuzzled into his neck. As he opened his eyes he saw the clock and realized that it was later than usual, almost 10am. The events of the previous night came flooding back as his mind shook off the tendrils of sleep. He remembered submitting to...

The Lost World Ch. 04

by TheTask on Sep 26, 2017
NonHuman

Note: I've been on hiatus for a few reasons. The first was that I recently acquired a job which doesn't pay terribly well, but a job is a job. The second is that I am writing a non-erotic story which I will not be posting anywhere, I haven't really decided what I'll do with it. The third is that with me being a young man, I have certain needs, otherwise know...

Becoming Jacqueline Pt. 01

by Jacqueline_Love on Sep 12, 2018
Transsexuals & Crossdressers

Summers were always so boring. All the other kids I went to school with loved playing baseball, riding bikes, chasing girls, or going to the beach during summer break, but not me. I usually spent my time in my room playing online games or watching movies or helping with chores around the house. I did not like most sports -- I never did. It was so much effor...

Swipe Right Ch. 02

by amb_anonymous on Jul 23, 2018
Transsexuals & Crossdressers

If you haven't read part 1, I'd recommend it since that is the start of the transformation, but this story could pretty much stand on its own. This story contains interracial, dom/sub, t-girls, crossdressing/sissification and bondage. This story is fantasy. I like to stretch the limits of what's possible, so don't expect pure realism. For clarity: In m...

Successful Businesswoman Ep. 02

by mattpantyhose on Jul 9, 2018
Group Sex

I would like to thank Georgia Alice for helping me with naming and dressing the characters. Somewhere by the end of this episode, during the final scene, I have made a stylistic mistake, it was done on purpose for the readers entertainment. I am curious what you think about it; please, let me know in the comments or via email. Any kind of feedback, especia...

Blowback

by dreadknots on Jun 18, 2018
Transsexuals & Crossdressers

Another story! This one is a sorta reversal of a typical mind control scenario, where the slighted nerd ensnares the stuck up bitch. What happens when it backfires and turns a horny guy into a sissy sextoy? Lewd shit, obviously. *** Chloe flicked through the tabs on her laptop's browser, skipping between links and trying to polish up her history paper. Thi...

A Sissy is Forged

by KassiSmart7 on Oct 15, 2017
Transsexuals & Crossdressers

This is my first go at writing. I've had a lot of fun writing this, I'm publishing this to see if other people enjoy it as I have. If it's a success, I'll continue the story. Hopefully, more chapters to come :) ***** When I told my girlfriend, whom at that point I'd been with about two years, that I was interested in exploring my sexuality, she was more th...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

Nathalie's Makeover

by Cagivagurl on Dec 2, 2019
Transgender & Crossdressers

Where to start? My name is Nathan and I am a married man, wed to my beautiful wife Vivian for three years. I work as a software engineer for a local manufacturing plant. Vivian works as an office administrator at a local paint distributor and in a word she hates it. Vivian has always been obsessed with fashion and everything there is to do with it. All sh...

Tai's Story Ch. 05

by Cagivagurl on Nov 4, 2019
Transgender & Crossdressers

So back at work and it was hot and sticky 300 KM from anywhere. The daily temperature on site was close to 45 degrees Celsius and I had never seen rain in all the time I had been there. It was hot dry and arid. Work was becoming more and more of a chore. When I started here initially it was amazing. It was good to get away but now it was becoming a drag. The...