Cum In Shoes Stories

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Infinite Scroll

Introducing Tony to Crossdressing

by Lynda68 on Mar 2, 2020
Transgender & Crossdressers

For as long as I can remember, I have always loved to try on women's clothes. It started with my sisters knickers and bra's. Or my mother's tights. Or even all together. My mother's skirts dresses and blouses were too big. Sis's things never felt right. I carried this kink, all alone. Even when I got married. Eventually I did come out to my wife, after a...

Property of the RC Ch. 05

by Boffa32 on Jun 15, 2020
Interracial Love

Property of the RC - Chapter 5 Bitch Emily Gets a Makeover Dr Emily Koumides had not been seen since she left college to visit a students apartment the night before. Now as Marcus the Repatriation Company investment manager opens the tailgate of his SUV no one recognises the collared slut who crawls out as the college lecturer. Stripped of her clothes and...

The Hole Cost of Heels

by DerekTheene on Sep 16, 2017
Anal

Heels Candace was dolled up in her skintight cocktail waitress uniform, a sexy sight. Sassy breasts, long legs, and totally taught bottom as she strolled on her way to work through the shoe department at the new Nordstrom's on Manhattan's 3rd Avenue. Admiring exorbitantly expensive high heeled Italian and other exotic leather boots and shoes, she peered at...

Christie's Homeless Friend Pt. 06

by TeroWright on Dec 24, 2019
Fetish

He smiles softly, "That said, with my former physique, death won't come easy. You two might wear yourselves out before I'm unable to handle you anymore." "I've worn you out before. I can do it again hun," she replies smiling back, resting on both her arms that are leaning on his shoulder. "Then do it. Why wait?" "Because you don't have your former physiqu...

Vanessa's New Life Ch. 11

by VanessaEvans on Sep 19, 2017
BDSM

This is part 11 of my Journal. I started writing it when I made a bold decision to change my life. I left my dull existence in North Wales and went to work as a Housekeeper for a man in the East Midlands of England. It is a decision that I will never regret. I have never been so happy and never had so much pleasure. Vanessa Week commencing July 5 Monday...

The Toy Maker

by oneguy4fun on Sep 26, 2017
BDSM

Synopsis: Carol has a talent for making toys. Hers are no ordinary toys. In this story she adds a young husband and wife to her toy collection. Chapter 1 Planting The Seed Julia closed her eyes, inhaled deeply and immersed herself into the soothing comfort from her husband's warm hands. Tom's hands slowly massaged a creamy scented lotion into the bottom o...

Caught at Work

by bigdaddysmooth on Sep 14, 2017
Erotic Couplings

Ryan couldn't take it anymore. His boss was just too sexy and having to see her everyday was too much. She had a Sarah Jessica Parker-esque appeal and look to her. She was no taller than 5'1, thin, with beautiful toned legs, and a pair of perky tits. Even dressed in a simple red top, low cut jeans, and a cute pair of open toed heels, he got hard. It didn't...

The Office Ch. 03

by KittenYume on Sep 17, 2017
BDSM

Kailey skittered out of Miss Mallory's office as soon as she was given permission. Her pussy was tingling and she could feel her juices running down her thighs. With no panties to catch it, it dribbled down her legs all the way to her ankles. She could feel eyes on her as she hurried through the office. Someone actually whistled at her and it made her want...

Stockings and Heels in Public

by stockingsheelsohmy on Sep 13, 2017
Transsexuals & Crossdressers

This is a true story. Feel free to comment if you've had similar experiences or fantasies. * It was bound to happen. I had dressed for months in secret. Going even further, shaving my legs, chest, genitals and bottom. Hiding my newly acquired heels & stocking from my significant other. I had felt it for months. The drag of the same routine. Dressing, ridin...

May & Deke Ch. 01

by BlueByrd on Sep 17, 2017
Exhibitionist & Voyeur

Chapter 1 - Window Seats My name is May, and I am meeting my lover Deke today at a lakeside motel in Maine. I haven't seen him for three months and I am so horny I am going out of my mind. I masturbate all the time we are apart--imagining he is here in my bedroom. Lying naked on my bed with two pillows under my hips so that I can see my own pussy, I spread...