Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Me & Courtney Ch. 01

by sexy23luvchic on Sep 13, 2017
Exhibitionist & Voyeur

I was eighteen at the time. I had a low paying job as a salesperson at a large fitness and sporting goods store. Although I usually worked in the baseball equipment section, my co-worker Lisa was out that day and I had been asked to cover her sector too. Lisa worked the women's sportswear section: a job usually consisting of explaining to middle aged women t...

Our Sub Fantasy Fulfilled Ch. 04

by DiggerDave on Sep 17, 2017
Fetish

This is a continuation of the story 'Our Sub Fantasy Fulfilled'. If you have not done so already you may find it useful to read the previous chapters. The other day Patty came home from work and told me that Amy would again be coming over on Friday evening. She told me that this visit would be slightly different from Amy's previous visits to us, as she had...

A Cum Filled Condom Ch. 02

by curiously_curious on Jul 31, 2019
First Time

With a pop, his cum covered cock slips out of my mouth. I instantly take heavy breaths having strained for air while his cock was buried down my throat, unable to get any words out of my mouth, my sole focus was letting the cool air in. He spent the last 10 minutes holding my blindfolded, noise cancelling headphone wearing head in place, with an overpowering...

A Millbrow Idyll Pt. 06

by giandomenico on Oct 7, 2019
Transgender & Crossdressers

As Zack pushed open the door of his sister's lingerie shop, Helene turned towards him from the window, where she had been discreetly observing the action outside the post office. 'You didn't get much change out of Cassie,' she said. 'Give me time. She'll come around before long. Anyway I bet you've not got any further in trying to lure her away from this m...

Hubris of Youth Pt. 02

by ilikeithot6308 on Sep 25, 2017
Mature

Several readers asked for more, so here it is. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ "Oh, my god, Nick! Where did you learn that?!" Savannah gasped. A smile of wonder covered her face. I rolled off her, pulling my rubber-clad cock out of her with a 'pop'. "It's a secret," I replied, settling back. "Can I trust you?" "I never reveal a source," she g...

Experience, or 3 Fucks an Hour?

by sammican1 on Sep 17, 2017
Mature

This is a big subject and a long story. Maybe too long for Lit. I contemplated breaking it into two or three parts but haven't. Tell me if you think I am wrong. The faint hearted may not take it on, fuck 'em. Those that do, if they are genuinely interested in both the conflict and adventure of a young woman and an older man and what went on between them, wi...

Driving Jackie Ch. 02

by wallcleaver on Sep 14, 2017
Erotic Couplings

The weather outside was cold, the gloom of the day and wind blowing further enhancing the effect of the temperature. Although not too unusual for an early December day in western North Carolina, I am a warm weather person, and I am amazed that the first drop in temperature from a nice, lazy fall to the winter is often so dramatic. Fortunately for me, I was i...

Quality or Quantity of Fucks

by sammican1 on Sep 14, 2017
Mature

Prologue This is a long story. There's lots to say about the subject so I don't apologise for the length. Also I don't apologise for the slow build up at times and the lack of 'wham, bang, thank you etc.' My style is not everyone's cup of tea so, If you don't like it, don't read it. This is quite a heartfelt story, the astute amongst you will work out why...

A Punk Rock Girl & Distressed Priest

by Jerkface_ on Sep 12, 2017
Erotic Couplings

It was a balmy night, with gusty winds peppered by weak rain. Jesse marched clumsily down the dark and empty street, her heavy black boots clomping along beneath her, feeling the strong abandon of just enough booze in her blood as she sucked aimlessly on her cigarette. The sound of the loud music from the bar was still playing in her head; she hummed along...

Ordeal and Acceptance

by Painplay on Sep 17, 2017
BDSM

Robert was late getting to the club. He hated being late anytime, but particularly this time, because he'd agreed to be part of the show. He hoped he hadn't missed his chance. The week before, the club's owner and dungeon master had announced that a pair of well-known, experienced Dommes would be visiting from out of town to give demonstrations. They neede...