Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

Letter from High Coombe

by justincbenedict on Sep 24, 2019
Exhibitionist & Voyeur

Dear Shoeblossom... I don’t know if my involvement with Satanic Silki is my fault, because of my neurosis? You judge... First, my parents were weird, warped people. The oldest of us kids, Breanne, became an adulterous bitch, and my brother Brian’s effect was, he was a cruel asshole. And he ran off with my first wife. I’m Brogan, the youngest, the “sensiti...

Pantyboy Graduates to Crossdressing

by laceypantyboy on Oct 8, 2018
Transgender & Crossdressers Stories

Pantyboy graduates to public cross-dressing. Hello. Let me just say at the outset that I am not gay. I am a hetero man who really likes panties, stockings and pantyhose. I had been wearing them under my boy clothes for years. Some of my girlfriends were disgusted, some were OK with it while not being turned on by it, and a few of my girlfriends did (and do)...

Hotel Hot Tub

by Towelie on Sep 25, 2018
Erotic Couplings

It was nearly ten o' clock at night and Jasmine decided she'd had enough of driving. She was going to check into the next hotel she saw and get some rest. Luckily the next exit was only a mile away. She took it and the first hotel she saw was a Hilton Garden Inn in a suburban Nebraska town. She pulled into the parking lot, parked, quickly reserved a room on...

Magic Dress - Diana Pt. 02

by SlightlyRude on Apr 23, 2019
Transgender & Crossdressers

MEET THE GIRLS We were told to come early, and I could change into my outfit at Jason and Lucille's house. Lucille greeted us, looking very pretty and very feminine. She could easily pass. We went upstairs with our bags, and I was transformed in my favourite green dress. When we came down there were another couple of women. One had a big bust and quite cu...

A cross dressing get together Ch. 02

by MrSwift on Apr 21, 2020
Transgender & Crossdressers

Part Two The Latex Room New readers might like to know that me and Freddie, a friend of mine, have gone off for a cross-dressing get-together in a house just outside Reading. We've met some lovely people already and it does seem to be quite a sexy affair. I've been having fun in the Silk Room (see Part One) but now I'm about to move on to the Latex Room. Ho...

Adventures with Alex

by Hungry4aman on Apr 21, 2020
Mature

I'm an "old guy." Much of my coming out had to do with sex rather than lifestyle, but now lifestyle has just about caught up. I may be bi or gay or whatever, as if I even care. As the saying goes, where the dick leads, the heart will follow. Or something like that! After many years of hiding in the straight world, including two marriages, I have evolved, and...

No Strings Attached Ch. 04

by Tara Cox on Apr 15, 2020
Romance

Jon knew he should have left long ago. He had been here for hours. His early dinner long since finished. He had eaten two pieces of pie as an excuse to remain. He remembered the taste of the pie that night. He remembered everything about that night. Whether this was as good as that had been, he would never know. His sense of smell and taste deadened by those...

The Fourteen Days of Valentine's

by lilgool on Dec 24, 2019
Romance

On the first day of Valentines, my lover gave to me... She watched from a safe spot as he approached the car. The rose under the wiper blade took him by surprise. He carefully picked it up and read the tag. Yes, it was addressed to him. He leaned to sniff it and there was a slightly familiar fragrance. That was when he realized the rose was silk. Then he to...

Jingle All The Way

by SkyeGal on Dec 2, 2019
Erotic Couplings

Good gods, it had been a long night. He chuckled to himself, knowing that he said that every time, but it seemed a little truer this time. In fact, the whole project had taken a lot more out of him than usual. Was he getting too old? Was there too much on his plate? Had he lost his joie de vivre? He certainly hoped not, because a new project would start...

An Unexpected Gift

by Lexavier on Jul 16, 2015
Science Fiction

It was just another relatively quiet Christmas. The snow is slowly piling higher and higher, causing chaos with the unprepared commuters who slip their way to see family or friends. The cold air seems to penetrate your thick Parker coat no matter how tightly you wrap yourself inside it. "Only another five minutes", you tell yourself as you stride p...

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