Transsexuals+&+crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

The Work Shower

by AnotherRandomWriter on May 2, 2018
Transsexuals & Crossdressers

Howard Bryce went to the locker room five minutes before the whistle blew. He was in a hurry, hoping to beat his colleagues so he could change into his street clothes unobserved, and protect his secret. He power walked through the factory, taking an unauthorized shortcut between two processing machines (an act that would get him suspended for three days w...

Get Over the Grief

by contactsteph77 on Aug 7, 2018
Transsexuals & Crossdressers

Trevor had finally fallen asleep. It was the first time he had managed to fall asleep before the sun had rose for well over a week. He really needed this sleep. But there was a stirring in the bed beside him, not enough to jolt him awake, but his wits were slowly returning to him. Someone was in bed beside him, odd given that Trevor had gone to bed alone....

Thrills in the Night

by melanieatplay on Jul 24, 2018
Transsexuals & Crossdressers

I pressed the 'ground' floor button on the elevator and checked my look one last time in the mirror. White button-down shirt, brown leather pants, and brown oxfords... It was a classic, yet contemporary look that the ladies seemed to love. The rain started to fall again. Sunshine all week long. Then, light drizzle all weekend. Isn't that always the way? It...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

The Live-in Maid Ch. 02

by Quietoldie on Jan 31, 2018
Transsexuals & Crossdressers

I think that everyone has deja vu every once in a while. Well when Barbara Kane walked through the front door of the shoe shop I had this strange feeling that I'd met her somewhere before. She has a commanding presence. Quite apart from her beauty there is something else about her. She's tall, but it's not just that, there's an air of confidence about her to...

A Handy Surprise Ch. 01

by SissyTrixy on Mar 14, 2018
Transsexuals & Crossdressers

As I laid on my bed I was listening intently for the sounds coming from the front the house, my heart was pounding. I heard a car drive to the front of the house, and moments later mom shouting something unintelligible and the wheels of her luggage being drawn across the tiled floor, her high heels clacking hurriedly across the hall. I had checked her flight...

Oh, Mr King! Pt. 05

by exaucer on Mar 6, 2018
Transsexuals & Crossdressers

At some stage during the night I became aware that Mr King was trying to push his fat cock back into me again. I was too weak to resist, not that I wanted too, and too far gone to fully participate, so I merely adjusted my position to facilitate his penetration. Since my pussy was still slick and sticky from his earlier deflowering, Mr King's cock eased into...

Biker Bitch Ch. 10

by MicheleNylons on Jan 7, 2018
Transsexuals & Crossdressers

Chapter Ten: Sisters of Satan Natalie Styles decided to cool things down with the Cartel for a while. The listening devices Cassie had planted in Carlo's house were providing valuable evidence and intelligence for the FBI and a strategic decision was made to allow the Medici's to keep importing drugs, girls, and weapons into the USA. Intel was passed onto l...