Cum In Heels Stories

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Tricked Into Pegging And Sucking!

by Everyday2 on Sep 25, 2017
Transsexuals & Crossdressers

It all started about two months ago when my wife and her two girl friends turned the tables on me and the two husbands of her friends. We had been getting together as a group for dinner parties with a theme for a long time. Always it was the guys who decided what the theme for the party was, and we had done football, hockey, pirates, Disney, monsters, etc. Y...

So You Want to be a Bimbo - Week 01

by modernromeo24 on Jul 6, 2020
Fetish

Introduction So you've decided to take your first step to become the best version of yourself. No, this isn't a self-help book. It's more of a guide to your own sexual awakening. If you follow these steps, you will feel happier and more confident. And, of course, you will be turning heads when you walk down the street. Being a bimbo is not just changing ho...

The Homosexual Sissy Wife

by jakladd on Sep 14, 2017
Transsexuals & Crossdressers

I love being the one for you, the one waiting at home for you while you are at work. The house is immaculate. My time at home is spent making everything perfect, especially me, your gay sissy wife. Gay does not aptly describe the level of homosexual submission I have towards you. Being femme and sexy for you is my constant quest. I spend hours at our home gy...

Sissy's Decline into a Slut Pt. 06

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Eight: Moving Along with my Sissy Maid Life and lots of Sissy Slutty Sex too. [Beep, beep, beep] My alarm clock goes off and a struggle to wake up. It is 7:00am and I come around to realize I'm in my sissy bedroom in my Master's house. I get up quickly now, in my white satin bra and panty with white satin full slip, this is my sleeping lingerie. I t...

Caught and Put in Lingerie!

by Everyday2 on Sep 12, 2017
Fetish

My name is Steve. I am a 27 year old salesman who travels around the north east US selling garden tools and supplies to department stores. This means I am frequently in hotels for a few nights a week. I tend to prefer the Courtyard Marriott style hotel - simpler, cheaper, and comfortable. I am 5'7", and about 180 lbs. I am in good condition as I work out o...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

The Sound of Heels

by darkchalice on Mar 6, 2018
Erotic Couplings

My studio is in the north end of my loft where there's lots of daylight and plenty of space for a large computer set-up, 3-d printer, flat files and so on. I'm a partner in an architectural firm, but can usually work from home. The past few years in my loft have been blissfully quiet since both the apartments upstairs and downstairs have been seldom used pie...

First Time

by Pantyhoseheels on Dec 2, 2019
Transgender & Crossdressers

This story is true, as I best remember it. I have had a pantyhose fetish since a very early age. I love both women and men in pantyhose. Tan pantyhose have always been my weakness. I have always tried to keep it my secret. Eventually I got my own place, and well, I wore pantyhose as much as I wanted. At some point I started to add skirts, which I loved to...

Panty Boy Diaries: Entry 02

by _pdy_ on May 21, 2018
Transsexuals & Crossdressers

Hi folks, I'd just like to open this diary entry with a quick thanks to all of my readers. It's been an honour and a turn on to know that there are people who enjoyed Entry 1. Now it's time to get down to what you all came for (pun intended, I hope), Entry 2. J had collapsed forward, forcing all of his weight onto me, smothering me into the bed. I could fe...

Some Fun at a Wedding

by midwestfeet on Jul 15, 2020
Fetish

**Please note - this story contains wife sharing/cuckolding. I put it into the fetish category as the foot fetish is the main theme. If you do not care for these subjects, please move on.** My wife and I attended a wedding last weekend. It was unusually nice out in December where we live. My wife is a hair stylist and one of her clients was getting married....