Crossdressing Dare Stories

42,978 results
Orientation
Length
Source
Infinite Scroll

Public Portland

by desert_fox on Sep 13, 2017
Exhibitionist & Voyeur

I'm sure lots of people have met in chatrooms, but I never put much stock in it. Sure, I'd been in a few, had a little cybersex, but it wasn't something I did on a regular basis, or something I used to find women. There always seemed something so...detached about it. But lately, it had been long enough since my last girlfriend that I had been on-line just a...

Seduction Ch. 10

by neolithic_one on Sep 16, 2017
Mature

Sunday morning I woke with a start looking at the clock beside the bed I saw that it was 11.30am and daddy was not there beside me. I washed and dressed and went downstairs to find everyone had just finishing breakfast. Julie made me some scrambled eggs and toast and gave me a glass of fruit juice. Later we sat talking and Jim told Julie and me that he and...

Pushed Too Far

by Hecate on Sep 14, 2017
BDSM

Disclaimer: This story is a work of fiction – alas, there is a very true undertone to it. It is one of my nightmares from the early times, when I gathered my first experiences as a Domme. If you feel easily offended or disturbed by graphic violence do not read further. Besides that there is hardly any reference to sex in this story – so this piece of writing...

Desire

by manish_30 on Sep 13, 2017
Exhibitionist & Voyeur

Actually this would have not been easy unless I came across this wonderful site, where I read other people experience and thought of giving away my own. To introduce my self I am 30yrs married to a beautiful women now of 28yrs. We are happily married couple for last 6yrs now and were having a very regular life till last 4 yrs before. The incident, which happ...

The Hayride

by wordmaster on Sep 13, 2017
Erotic Couplings

Mony tumbled onto the wagon willy-nilly and ended up between Tom's legs. He sat with his back against the sideboard, his legs on either side of her. She tried to give him a little room, but the crush of people pushed her back. Still, she hugged her knees rather than lean against him. In the dark, she could see very little. The straw smelled clean and fresh....

Stoned In Texas Ch. 04

by kokshur on Sep 13, 2017
Celebrities & Fan Fiction

I love the city of San Francisco. I live and work here. I had a day off and on a whim I went down to Fisherman's Wharf, wandered down to Pier 39, and back up to Ghirardelli Square. Watching the people more than looking at the goods in the shops. Tourists and locals playing tourist with their friends and relatives. I was in a souvenir shop, looking at snow...

Night Shift Nookie

by biguy0321 on Sep 1, 2017
Group Sex

Another long weekend working the night shift. I often think this shift makes a person lonely and disconnected. I wanted that feeling to go away the other night, but how? I knew what would feel really great right then - meeting up with the little nympho blonde in ICU and the hospital's hairy-stud maintenance man. Well, they were both in-house that night and t...

Golden Mile

by SistaShakespeare on Sep 12, 2017
Romance

Another sun-drenched day, but now the late afternoon sun's turning fiery red as it sinks in the sky. Sticky, humid, my skin feels hot, grimy under my fingertips. Looking down at my bare arms in the last orange light of the setting sun, I'm amazed by how brown I've turned since the beginning of the week. The blended aroma of hot-dogs, candyfloss and the acrid...

All's Blonde in Love & Mother

by DiscipleN on Sep 1, 2017
Humor & Satire

Copyright (c) 2002, by DiscipleN. All rights reserved. This work may not be used for any commercial purposes without prior, documented consent from the owner. * * * * * Have you heard the one about the dumb blonde? Have you ever met a dumb blonde? Now, what about the fakes? I mean peroxide hair girls and pretend airheads. Is the dumb blonde stereotype so...

Little Sister Ch. 02

by Da_Vida on Sep 16, 2017
Transsexuals & Crossdressers

Gene faithfully attended to Denise's intimate laundry for the next several weeks. Though he was a bit concerned that Helen or his father might catch him in the act of washing out Denise's undies he couldn't control the excitement that arose in him whenever he went into the bathroom and found the little net bag waiting on him. Outside of the apprehension he f...