Stiletto Boots Stories

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Infinite Scroll

Hausfrau

by Vera_Garden on Sep 16, 2017
Transsexuals & Crossdressers

The night they came back from Octoberfest, she burnt all his clothes. Gerrig and Margarethe agreed a week before that they'd both wear traditional dresses to the famous German beer festival in Munich. "Gerrig, I only have one dirndl. Why don't you wear your lederhosen you wore last year? The way your thighs and butt look in the tight leather, it gives me id...

A Lesson On History For The Future

by michelino on Sep 17, 2017
BDSM

I am over 45 and to get a certain perspective, I am taking adult University courses to improve my general culture. One day, at the end of a lesson, my regular history teacher, Mrs. Clementina Maze, asked me to stay in the classroom to tell me that a specialized and renowned teacher coming from the Netherland, Mrs. Donna Karina, was in town and looking for...

Falcon and Domino Ch. 09

by Willow_Creek on Sep 14, 2017
BDSM

As Falcon looked down from an office rooftop that Friday evening, he heard gunshots coming from a nearby factory. When he arrived there, he found a security guard being held captive by two masked gunmen. Falcon crept up on the gunmen and knocked them out with a blow to the neck. The security guard ran into his office and phoned the police. Falcon was unaware...

Super Heroes Ed. 02

by grgy56 on Mar 2, 2020
Transgender & Crossdressers

Super Heroes - Edition 2 There I was. Standing in the front of the full length mirror dressed as Zantanna Zatare - Justice League of America superhero. From the top hat with my long, flowing raven hair cascading down over my more than abundant breast forms barely contained under a tight fitting, frilly blouse and jacket, to the panties that formed my penis...

The Teasing Air Hostess Ch. 03

by footslave85 on Sep 26, 2017
Fetish

Chapter three I arrived home and immediately dropped everything, practically ran to by bedroom and was naked in seconds lying on my bed. I had the stocking draped over my face and reached down to massage my already hard cock. I had been stoking for about 5 seconds when my phone beeped. I instantly remembered that I was supposed to wait for instructions and...

The Dutch Master Ch. 06

by suboots on Mar 6, 2018
BDSM

I was quickly discovering that the management of pain was something that can only be done inside the head. The serrated jaws of the clover leaf nipple clamps latched on tenaciously to the little nodules of flesh, creating an intense, if very localised agony, out of all proportion to their size. I tried various coping strategies but ultimately what it came do...

The Project Pt. 04

by Chloecrownofthorns on Jan 20, 2020
Transgender & Crossdressers

"What did Delilah put in that last drink?" Chris thought. "Perhaps I had too many, but what crazy dreams I had! They seemed so vivid and real!" Chris's dick swelled as he recalled the previous night and a wave of pain hit him. He reached down to touch his dick but found nothing to grab. Panicked he ripped the covers off and looked down. "Oh no, no, no!" H...

My Paula Continued

by paula and bob on Sep 17, 2017
Loving Wives

The first time I found out about the wilder side of PAULA was when we were having sex on her living room couch. PAULA seemed hotter then usual tonight. She had just returned from a weekend trip with her girlfriend. They had gone upstate to visit her girlfriends boyfriend Bill. We started out kissing and PAULA started to take the lead rubbing my cock throug...

The "Dresssmaker"

by Classygloves on Sep 18, 2017
Transsexuals & Crossdressers

I was all excited. The emerald green satin evening gown that I had purchased on Bay was just delivered. I had been planning for months to dress up and attend the gala ball at Fantasia Fair, an event held every year at Provincetown, Massachusetts for transgendered persons and cross dressers. I nervously opened the package and hurriedly undressed to try on thi...

Kitten - An Introduction

by Badboylax1 on Aug 30, 2017
Mature

I like to call her Kitten or BabyGirl in public. She is a real girl, with feelings and emotions and needs I try to meet, and hopefully get close to satisfying. We complement each other so well. I'm an older, assertive, gently dominant man. Kitten is much younger, beautiful, slim, sexy and submissive. My Kitten likes to please me by doing what I tell her, and...