Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

Aficionado Gets in Trouble Ch. 02

by His_fag_wife on Jun 12, 2019
Transgender & Crossdressers

Mark cleared the clothes from the table, he wanted a truly clear picture of Pete being used in the stockade, knowing he'd get some great footage for his website selling the stockade frames, it would help sell some more without giving away Pete's identity from the side view. But he'd also get some head on footage for posting on the internet should Pete fail t...

Casey Blossoms

by jackie_em on Feb 7, 2018
Transsexuals & Crossdressers

As I grew up, I knew I wasn't a guy – not a normal guy anyhow. The normal boys liked doing rough things, fighting, playing war, playing sports, watching sports, hunting, fishing, all those male things. I didn't like any of that. On the other hand, I never wanted to be thought of as a sissy. I went through some of that, so I hung out with the boys and did jus...

Casey's Submissive Journey Pt. 04

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part Two After putting on the movie Angie walked to the side of the bed and carefully removed her hat, gloves and shoes. As she did she called Debbie over and told him to lie down and get comfy. He took a sip of his drink, put it on the nightstand, then laid down on his side and watched the video. Soon after he felt Angie's w...

Jennifer Monroe & the Ladies Ch. 01

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Jennifer Monroe & the Ladies -- Chapter one Jennifer held Debbie's hand as she led him down the stairs and into the finished basement. It was a large single room with a sofa, a few comfy chairs and a queen-sized bed at the far end. Seated on the sofa and chairs were five ladies, all of them dressed in corduroy outfits. Jennifer ignored them as she whisk...

Our Little Secret

by Drakon66 on Feb 5, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. - Authors Note: This story is a work of fiction. It contains incestuous acts between siblings. One of the siblings is transgender. If either of these subjects is distasteful to the readers out there, please accept this as fair warning to read no further. With that said, to those brave e...

Being My Roommate's Sissy Pt. 03

by SubTessa on Feb 6, 2018
Transsexuals & Crossdressers

SubTessa (Author): Sorry for the wait guys, University sort of made me forget about this entire thing. If you're new to this series and start here, I think it'll be ok. The last two are just the lead up to this day. I hope you enjoy it! You should also read these with a healthy level of self-esteem! ~~~~~~~~~~~~~~~~~~ I wake up, quickly forgetting what I...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Quiet Sunday Morning

by JimBob44 on Jan 14, 2018
Transsexuals & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: This story is edited by myself, using Microsoft spell check. You have been forewarned. *.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.* Duncan White sighed and wearily got out of the car. It was a 2003 Toyota Camry; ran reasonably well and was fully paid...

Caught in the Act

by Alice_Angel on Dec 25, 2017
Transsexuals & Crossdressers

Hey everyone! This is my first time sharing a story, so comments/criticism are welcome! Please let me know what you think. I know most readers want to get straight to the juicy stuff, so I try to avoid a lot of backstory. Suffice it to say, this story is based on a real person and set in a real place, though the events never actually happened. The main cha...

Neighbourhood Terror to Sissy Pt. 04

by Fibaro on Mar 25, 2019
Transgender & Crossdressers

The next morning Mark was woken up by a loud mechanical voice. "Wakey wakey sissy, time to start your day, and what better way to start it than with another wank." Mark groaned loudly but he did as the voice said anyway. With a sigh he grabbed the boxers of his night stand and Pulled them over his head once more. Since this had started he had spent countle...