Leather Skirt Stories

149,480 results
Orientation
Length
Source
Infinite Scroll

The Limousine

by misspandp on Sep 13, 2017
Group Sex

Richard hadn't told me much at all! He told me that I would be picked up at eight and I was just follow instructions. So here I was, standing on the corner again, dressed and made up in a fashion that was most obviously having an effect on the men going by. I was wearing my lacy black top with no bra underneath. It made me feel very exposed as the warm night...

Cindy Shopping

by cindyandal on Sep 14, 2017
Exhibitionist & Voyeur

“Oh, this is kinda cute!” Cindy said, holding up a dress. The dress was vinyl. It had vinyl straps holding up a top that was cut low across the front. It was short. And the front was connected to the back by 3 one-inch vinyl strips on each side. The strips separated the two halves by about six inches, leaving a wide expanse of skin to be seen. It was slightl...

Hot Summer Night at Jacques

by Mickytv200 on Sep 16, 2017
Transsexuals & Crossdressers

I sat on a red leather bar stool. To the world I looked like an attractive heterosexual male, wearing thin cotton summer slacks and a black tee shirt. I have sandy brown hair with bright blue eyes. My body is slender from running and swimming. I am about 5'11" and weigh about 160lbs. On the night at Jacques, I was about 30 though I look younger. My hair is l...

Leather Shemale & Leather Wife

by LeatherKev on Sep 19, 2017
Fetish

I have always loved seeing others wear leather. I, too, love to wear leather and have a growing collection. I can't remember when it started but it seems I have always had this fetish for leather. During my first job out of college, I met a lovely young woman named Mikky. She was beautiful. Long dark hair, blue eyes, and long legs. All I could think of was s...

Caught by the Past Ch. 01

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1 - Dress to impress Your latest girlfriend, Karen is very kinky and she introduces you to all manner of strange people. You on the other hand are rather naive and innocent. You found one handsome guy, James strangely attractive. He has long muscular legs, a washboard stomach, dark skin, blond hair and an impeccable speaking voice. Having met many o...

The Keyholder Ch. 02

by AndreaJordan on Sep 18, 2017
BDSM

Ben returned home and stood alone and naked in his minimalist lounge. The belt was a beautiful object, shiny, sleek and contoured around his narrow waist. The smooth metal ran down behind him, partially covering his butt, with only a small hole through which he could shit. It eased between his legs and widened as it came up over his cock and balls. They were...

Jesse's Forfeit

by sexy_jessie on Sep 12, 2017
Transsexuals & Crossdressers

This story is the second chapter two my earlier story "A High School Bet" which can be found in "First Time". Although this story works ok as a stand alone story it may help to have read my other story first. *** Jesse Sinclair felt slightly awkward and worried. He'd made a bet and lost and now he had to face the forfeit dreamt up by his kinky twin sister...

The Station Shelter

by ColinCox2011 on Sep 13, 2017
Erotic Couplings

I glanced to my side at her as we walked up the deserted street. The wind gusted catching her blonde hair and her face was momentarily revealed in full. God, she looked hot. And without even trying particularly hard to be either. I found it a unique talent of hers, the way she could turn me on simply by wearing normal everyday outfits. To be fair, these wer...

Panty Boy Ch. 04

by vieuxbleu202 on Sep 12, 2017
Transsexuals & Crossdressers

We pulled into the driveway and got out of the car. I carried all of our new things into the house. By this time my feet were killing me so I took off the heels and sat down for a minute. My feet were throbbing; it felt so good to get those shoes off. I have a new respect for women who wear these things all the time. Megan grabbed a few bags and walked up to...

Tidbits

by Trubbycat on Aug 18, 2017
Fetish

It's been over a year since I have contributed a story, due mostly to a career change and returning to college after nearly 25 years. I have been scribbling little outlines and scenarios the whole time, though. These two pieces were originally little mash notes I sent to my wife, scenarios of things we have discussed, would like to try or just dream about. W...