Crossdressing Dare Stories

42,978 results
Orientation
Length
Source
Infinite Scroll

Young Men Exploring

by Lynda68 on Dec 24, 2019
First Time

Steve and I have always been friends, and we were usually together throughout the day lately, both unemployed, very bored and skint. Although I could always visit Jon. He would suck me off and give me enough money for a pack of cigarettes, beer etc. He also had a good porn collection which I often borrowed from. Getting the lads around to watch porn videos...

Live to Please...

by KiryusAna on Jan 21, 2020
BDSM

My waking up to a warm sunshine was a special occurrence in Master's room, as the curtains are usually closed, keeping the room dark until I were to open them to awake my Master, however, today was different... because I forgot to close them the night before, due to... well... activities spontaneously sprung on me by Master... I stretched out a little on t...

Family of Rome Ch. 01

by Delilah_Morgan on Dec 24, 2019
Novels and Novellas

Aelia was carried along the streets of Rome, the white curtains of her litter kept out the harsh rays of the sun while still filling the small place with a warm glow. It did nothing to keep out the noise. Every fish monger, wine merchant and other vendor in the eternal city hawked their wares at the top of their lungs. It was bad enough having to be out of h...

Sir Punishes Jessica

by SmokinJ on Dec 24, 2019
BDSM

I heard the loud engine from Devon's truck arrive in our driveway. Oh shit! Devon had told me to make sure the house was clean before he came home. I scrambled off the couch onto my feet, to at least give the allusion that I had been cleaning. The distinct sound of the key entering the door and the door knob turning, sent me into overdrive. Devon glanced ov...

Cristina's Slave Husband

by 2psparta on Jun 8, 2020
BDSM

Cristina was my Dad's new wife. She moved in about six months ago when they got married. I'm 19 but she insisted that I call her Mommy which I found very uncomfortable. I complained bitterly but Cristina uses her beauty to get her own way. She said, "I know you've been sniffing my underwear in the basement while you're on laundry duty. If you learn to reco...

Girlfriend's Fantasy

by Penisleeve2020 on May 12, 2020
Exhibitionist & Voyeur

Sue was a quiet young woman, red headed, huge tits but otherwise tiny. I'd been her first boyfriend and to my knowledge only one other cock had been inside her when she'd taken on a dare and got bareback fucked by a friend from uni. I'd wanted her to 'go and get fucked and come home leaking cum.' She had done so inspired by a randy girlfriend of hers and wh...

Compromising Positions Ch. 08

by Timeris on May 12, 2020
Exhibitionist & Voyeur

Late Saturday morning, Jenne woke. After a moment's disorientation, she saw Angela and the evening came rushing back. What a wild night! Hell, what a wild WEEK. On Monday, she'd been shy, quiet and conservative. By Friday she was flashing a crowded nightclub, loving every minute of it. She'd experienced another woman, found she liked it, and discovered she h...

Kiran and Priya Ch. 02

by indsub89 on Jul 15, 2020
Exhibitionist & Voyeur

The conference which Kiran was supposed to attend, which had caused Priya to offer her help with his dressing sense, which, in turn had led to him kneeling naked in front of her was supposed to be a week later. It got further postponed by another week. In those two weeks, things changed heavily between Kiran and Priya. The first change happened the morning...

Obedience and Worship

by CuckFantasy69 on Jul 15, 2020
Exhibitionist & Voyeur

***DISCLAIMER*** The story is a fantasy I wish I could fulfil with my crush I met online She is aware of my kinks and I dedicate this and the upcoming chapters to her. Please leave comments, I will kindly ask her to read my work and your feedback. Thank you. I am 25 and she is 24. I am a voyeur at heart. I love to watch. I love to witness how the atmosphe...

Panty Trap

by HopefulGentleman on Jul 13, 2020
Exhibitionist & Voyeur

"One of you has to work late tonight, so who's it going to be?" Denise asked. Sherry and Rob looked at each other from their office chairs, and then each twisted their head toward Denise and said, "Not me." "Shit," Rob said. "There's no way I'm working late tonight," Sherry said. "I'll leave you two to work it out amongst yourselves, but one of you is st...