Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Julia, Ben and Lisa Ch. 19

by chloejacobs83 on Mar 31, 2020
Transgender & Crossdressers

Ch. 19: Saturday - Monday A few quick notes: 1. this is the nineteenth and last chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned Because Saturday, Sunday and Monday are short...

CD Internship Ch. 06 - Meetings & More

by cdtycoon on Apr 22, 2020
Transgender & Crossdressers

CORPORATE MEETINGS & MORE SERIOUS SATURDAY After the fire incident, the work was going smoothly until Saturday; when all of a sudden the workplace was more active than any time from when I join. It was time for a half-yearly general meeting consisting of the Board of Directors with all the investors. Not only that; I got to know, as due to the recent fir...

Candy's Fashion House Ch. 06

by Cagivagurl on May 21, 2019
Transgender & Crossdressers

Thanks to Charlie for the editing, advice and support. ***** After a couple of days Lauren still hadn't returned. I called Karla to see if Lauren was staying with her but she hadn't seen her. For the next few weeks the status quo remained. I was living at home by myself. For all intents and purposes Lauren was gone and I was now single. She refused to answ...

Home Helping Hands

by Kashman007 on Jun 28, 2020
Erotic Couplings

“Hey Andy, what about this one!” John threw the paper to Andy who was slumped on the sofa watching daytime TV. “What am I looking at?” “The wanted ads – somebody wants a home help” Andy sighed. “Oh great – basically a cleaner. That’s not gonna go far to getting a deposit for my own place, is it?” “No – look at the ad. It says the job is 7 days a week, so the...

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Maid to Order Ch. 01

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele Ascending My wife had left me a year ago. I'm surprised she waited as long as she did really. We were married when we were both eighteen when I was in the army. She had been my only girlfriend and I was scared she wouldn't wait for me because I was being deployed overseas. It was a whirlwind romance. I'd heard rumours that she'd been a bit loose be...

The Role Players Pt. 06

by hollygurl29 on Aug 1, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

Mistress Sharon Pt. 01

by corduroysissy on Sep 5, 2018
Transsexuals & Crossdressers

Dana had just finished moving his corduroy girly clothes from the washing machine to the dryer when the phone rang. Being a closet fag and having a corduroy fetish, he not only dressed often but jerked off with his wardrobe on a daily basis, sometimes two or three times a day. As you can imagine that created a lot of sperm stains, and his skirts and dresses...

Tai's Story Ch. 09

by Cagivagurl on Nov 18, 2019
Transgender & Crossdressers

Ginger staying in my bed became the norm for us over the next few weeks. She just seemed to slip straight into my life and it was so easy we didn't fight or argue. She got on so well with Talia it was like they were sisters. I did feel sorry for Alex who was now feeling a little left out. She seemed very sad and disconsolate. I think the penny was starting...

Matt Becomes Mattie Ch. 05

by clarepanties on Sep 14, 2017
Transsexuals & Crossdressers

The rest of the weekend was fabulous. I will not go into all the details here, unless you ask me to, except that we had a wonderfully relaxing time. The food and hotel were good and the room warm and comfortable with a lovely bathroom. We took some walks, a short visit to antique shops, but most of the time was spent reading, watching naughty DVDs, and for m...

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...