Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Randy's Grand Reveal

by dkbeasley on May 7, 2019
Transgender & Crossdressers

I've known Randy since high school. We rode the same bus, lived less than a mile apart, were assigned to the same study halls and shared the same lunch period. This is not to say we were 'buds' back in the day but we were in shared company hundreds upon hundreds of times over a span of four years so we knew each other for sure. What I didn't know, had no clu...

Chrissy's Trip

by Ide32 on Sep 16, 2017
Transsexuals & Crossdressers

Part 1: Trouble in Paradise It has been seven months since Chrissy and Miriam had their memorable first date, and things are going well. Every night Miriam is in town she falls asleep with her giant futahood buried in Chrissy's cum filled ass, and most every night she is away Chrissy heads to Futanari Palace to sate his hunger for cock and hot futa juice....

Ready For Love

by komrad1156 on May 7, 2018
Transsexuals & Crossdressers

"David? Are you doing all right?" "Not really," he said rather quietly. His older sister sat down beside him and said, "It's been nearly four years, David. And you have Sophie to think of. Isn't it time you tried meeting someone?" "In principle, yes. I agree completely. But in reality, I...don't know. I just can't bring myself to get out there and even lo...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

With Her Blessing

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"Hello again, Kyleigh!" he said as he looked at himself in the mirror after carefully pulling on his very expensive human-hair wig. Ky Finley was now Kyleigh Finlay and she felt this wonderful rush of endorphins flood over her as she looked at the beautiful creature she'd become over the last ninety minutes. Ky had sandy blond hair so Kyleigh could easily b...

The Good Neighbour Ch. 01

by MicheleNylons on Aug 21, 2019
Transgender & Crossdressers

Chapter One -- Mary Reynolds Now... Steven Balfour stared down at Abigail Thompson through his aunt's bedroom window. Abigail was on her knees weeding her garden. She used a plastic kneeling pad so that her knees didn't get dirt and grass stains on them. This caused her shapely bottom to rear up, which in turn caused her skirt to ruck up around her thighs....

Fun with a Cherry Popper

by Floydman1 on Jul 2, 2018
Transsexuals & Crossdressers

Quitting time couldn't come fast enough. As soon as I had seen the notification of delivery, I couldn't concentrate on anything but what was inside the box, waiting for me at home. Finally! I was legal as I drove home, but barely. I had just managed to duck a conversation that was guaranteed to take at least an extra fifteen minutes. While I didn't brazenly...

Mistress Sylvia Pt. 01

by corduroysissy on Dec 18, 2018
Transgender & Crossdressers

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...

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...

Lady In The House Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

After the warden left my cell my mind was racing. Why were they bringing my sister here to visit? How was I going to remove my makeup and nailpolish? What was I going to do about my semen-stained clothing? I heard the keys rattle in the lock of my cell door and Steve strolled in. "Well Michele it look's like you are starting to behave. The warden seemed ha...