Crossdressing Dare Stories

42,978 results
Orientation
Length
Source
Infinite Scroll

A slave's Motorcycle Diaries Ch. 01

by Doggy4Mistress on Sep 13, 2017
BDSM

It's a beautiful Sunday morning and slave is excited. Because on Sundays, his Mistress goes for a ride on her motorcycle. And this Sunday, Mistress has promised to take him along. Slave has hardly slept at all that night, because he was sleepless with anticipation. He is waiting for his Mistress to come out and summon him. After what seemed like an etern...

Friday Night Punishment

by cute_critter on Sep 25, 2017
BDSM

On Friday nights, we eat dinner late, just the two of us. He works out of town all week, and comes home late Friday, sometimes on Thursdays, but almost always Fridays. I always cook dinner at home for him, and eat with him when he gets in. It’s a nice tradition, and we have so little time together, it allows us some private time. It’s not especially fancy, b...

I Love Men

by JJ on Sep 13, 2017
Erotic Couplings

I love men. I really do. I have loved many different men. But I love them all. Their smells and looks, the way they walk, the way they belch and holler, the way they will never admit how much they need us, and the way they never admit how little they do. They fascinate me these base and sensory creatures. A full belly, some sexual release and a few comfort...

A Country Ball

by Ladyquinn on Jun 9, 2020
Sci-Fi & Fantasy

It's the county ball, a grand and exciting affair. We have both attended for our own reasons. Maybe out of obligation, maybe out of interest, but it doesn't matter. We're both there in the crowded hall, and our eyes meet from across the room. I don't look away, instead holding your gaze longer than is proper. It becomes a contest to see who will look away fi...

My Mom's Feet Put Me in Therapy

by iloveannamarrie on Sep 24, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Amid the very uncomfortable silence, my eyes wandered, carefully, as to not meet Sharon's curious gaze. I was beginning to almost feel accustomed to these awkward quiet moments, week to week these sex therapy appointments seemed to repeat themselves, the shaky dialogue between Sha...

Strangers in the Night

by secretly_submissive25 on Oct 8, 2019
Novels and Novellas

Click And with that click of the mouse the ad was posted. Sent into the dark abyss that was the internet. The unspoken place where men and women went to in search of something. And that something was different for everyone. But everyone came to the same place to begin. And that's where she found herself. She saw the words in bright color on the scre...

Shared Bride Ch. 05: A Cuckold

by DandJ69 on Apr 13, 2020
Fetish

I woke early with a banging head. Jen and Brad were both fast asleep and still snuggling as they had been when we went to sleep. I went to the bathroom and procrastinated for a while, pondering on the previous nights events, before having my usual morning shit and shower. As I stepped out of the shower I heard a noise from the bedroom. I could clearly he...

Black Magic

by Magentasun on Mar 30, 2020
Fetish

She didn't think her life would end up this way. And yet here she was, waiting for her master to put on her collar and take her wherever. But this isn't to say that Eva didn't like it. The slight shiver that ran through her body as the man in front of her buckled the leather collar at her neck said it all. Eva didn't think her life would end up this way....

Oliver's Game

by CaitiGrr on Apr 1, 2020
Erotic Couplings

Caroline heaved a deep sigh, her small, perky bosom gently bouncing as she did. He was late. Again. She checked her phone for any missed messages or calls. There were none, and none would come. Oliver loved to keep her waiting. There was something about how obediently Caroline would wait that lit a fire in him. He thoroughly enjoyed testing her patience. She...

Diane Has A Threesome

by BiMax on Mar 2, 2020
Group Sex

I woke up late the next day and was a bit startled to find myself alone. For an instance, I thought it was a dream. All of it -- the affair with Jean-Claude, the sex with Luc, the sex with both of them. Perhaps I had woken up in my own bedroom after a crazy dream. But I hadn't. I looked out the window at the pristine backyard that wasn't mine. I was in Jean-...