Cum In Heels Stories

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9 Stone Cum Queen in the Suburbs

by 9StoneCumQueen on Sep 18, 2017
Fetish

(This is my third story for Literotica) * Here I am. I am the 9 Stone Cum Queen. My cunt is tighter than your wife's. I am five foot six. That's the perfect weight for my height, a doctor told me. I'm a good height for the average man. When I'm wearing heels and I bend over a table I find my cunt is at just the right height for the average man to slid...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

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...

A Few Beers Lead To My Humiliation

by lrwriter on Sep 16, 2017
Loving Wives

I really had no idea I would find humiliation so exciting, nor did I ever think I would submit so easily. But I was wrong on both counts. I should start by saying she had been my wife for only a couple of years. I was in my mid 20's, and while I enjoyed sex as much as any 20 something, she was five years my senior and had a lot more experience. I learned m...

Juliette Gets a New Dress

by Dreamstime on Sep 16, 2017
Transsexuals & Crossdressers

It builds up like a huge wave of excitement, lust and fear. My want for a dirty, no holds barred session with my wife. She knows it's building up in me, the grumpy comments, the early morning hard-on's that prod her in the back. Nice, romantic love making has its time and place, but the sexual animal in me is beginning to stir. "I want to be your sex...

The Fetish Shoe Shop Ch. 2

by fantasyboy on Sep 19, 2017
Fetish

I arrived early for my first day in The Fetish Shoe Shop. I was slightly nervous but also excited. Mrs. Wyles was already there sitting at her desk doing some paperwork. She looked very attractive with her hair freshly done and her face very well made up. She got up to greet me and I saw she had the red sandals on that I showed her yesterday in my mock inter...

A Sissy's Day of Fun

by sayaSky on Mar 10, 2020
Transgender & Crossdressers

Part 1 It was summer break, so I was visiting home after my first year of college. My parents were going to be gone for the next few days visiting old friends. Being by myself, I went online to a hookup app and searched for a match. In my ad, along with a picture of my ass in a thong, I said I'm a young male looking to get fucked by a top. It only took fift...

Dog Door and the Lawn Man!

by Sexybeast8899 on Dec 17, 2018
First Time

About two months ago I got a call from a coworker asking me to go check up on his wife. James started with our company about six months ago. We have become good friends. His office is down the hall from mine. He also lives in the same neighborhood as I do. It's a gated subdivision with maybe 30 homes. James is married and has three kids. His wife, Erica is a...

The Boxing Day Present

by garterbelt on Sep 13, 2017
Fetish

Christmas was, as usual, a peaceful and relaxing time with the special people in my life. I spent the day with family and friends. Boxing Day is for me to relax and unwind. I slept late, had a long bath because I was invited out to an old friend's for dinner that evening. When I arrived, he had his apartment all decorated, the table set with candles and it...

A Mistress, a Sissy, and a Slave Ch. 01

by thejm4n on Sep 15, 2017
Fetish

Clad in a skintight, black latex dress, and tall, 4 inch platform black heels, Jessica was a stunning figure as she looked down at her two slaves, on their knees. "Up" she said to Hailey. "Yes Mistress Jessica." Hailey stood, naked, save for the black collar around her neck. "Now" Jessica said, looking at the other slave, "it's time for a little fun with...