Trampling Heels Stories

81,118 results
Orientation
Length
Source
Infinite Scroll

Cheri's Ordeal

by FyodorKaramazov99 on Sep 16, 2017
Transsexuals & Crossdressers

Cheri knew that she had made an error in not following Ken's instructions. She felt that she would be able to do as she pleased while at home alone. That, of course, included the right to masturbate at any time. After all, she had been beating off several times a day since her early teens. To be ordered not to was unimaginable to her. She was about to pay fo...

For The Sensual

by sydian on Sep 16, 2017
Transsexuals & Crossdressers

Sydian~For the Sensual For the sensual, description is everything. The collar. The collar is custom-made; one of two; her request. This particular one matches the corset. The corset—the "bustier." The collar. Literally, no choker here. She is disciplined. Her collars merely evoke ownership. She belongs. She is well kept; and kept well. Tonite: more adventur...

Hello Officer

by Moxon4 on Sep 16, 2017
Transsexuals & Crossdressers

Tricia arose from sleeping in on her day off, she worked a regular office job, and had wrangled a day off. She was in her 20s, and she had let her blonde hair grow out some, although it didn't matter as much since for her job she usually kept her hair in a pony tail, or up in a bun. She normally awoke in the morning next to her boyfriend, Holden, but he was...

Interrupted

by grgy56 on Sep 16, 2017
Transsexuals & Crossdressers

Interrupted! I did it! The first part of my alone fun time was completed. I addressed the envelop to myself: Gere O'Keefe 869 Terry Rd. Suite 81 Streetsville, On. I placed a single key inside the envelop, sealed it shut and dropped it in the mail. It Wednesday and would take a couple of days, hopefully Friday before I would receive it back. You'll find...

Maid to Surrender

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When Mr Hastings first phoned me, I had no reason to think he was anything other than an ordinary client. I mean, so what if he asked me to turn up dressed as a chambermaid? That was one of the options mentioned on my business card. Transvestite maids have always been popular... My maid's outfit was the flimsiest kind; really just a cheap black mini-dress w...

Pleasure in the Park

by PickleBoi on Sep 13, 2017
Transsexuals & Crossdressers

I'd ridden that ride a thousand times.... But I just kept getting back into that huge queue line. I was at the local theme park riding the newest addition to the ragtag assembly of attractions, the Master Exploder. It was the craziest coaster I'd ever dared step my foot into. Everyone else loved it just as much as I did; it could take 30 to 45 minutes just...

The Perfect Scene

by sublocked on Sep 15, 2017
BDSM

In my roamings on the WWW I came across a few self bondage sites and I found it amazing what people would risk in order to achieve fantasies of helplessness. Some do die in such scenes. One does have to be careful. Here is a story of one man who took all the care required in order to survive, but was it enough? Jason had dabbled in self bondage for many yea...

Exposed

by MSSD on Aug 19, 2017
Exhibitionist & Voyeur

"Have you ever done any print modeling before?" Kim Fairchild says, shutting the door of her office behind her. Kim Fairchild doesn't look like an executive for an adult magazine, but then again Joel Wilcox doesn't know what an executive for an adult magazine should look like. Joel is twenty-three, with dark good looks and a polite, self-effacing manner tha...

Shopping For Men

by chloedeboncourt on Aug 19, 2017
Exhibitionist & Voyeur

Supermarkets. Nothing more profane, nothing more unspectacular. Overly ambitious people compare prices, get exalted by this week's bargain. Yet, every man who has not lost his manhood will treat the supermarkets as what they are: a pathetic regression from the heroic time of hunting your food. In the early times, only a man who could bring food home would be...

Escort Confessions: Vegas Nights

by Deckard6969 on Aug 31, 2017
Celebrities & Fan Fiction

Racquel Darrian in Escort Confessions: Las Vegas Nights Racquel had received an incredible financial offer, in writing, to entertain an old Las Vegas billionaire for the night, under one condition: she must perform every sexual whim he asks of her without question or hesitation. Any deviation from such an agreement would nullify the $10,000 offer. Once it...