Cum In Heels Stories

360,326 results
Orientation
Length
Source
Infinite Scroll

Shopping Trip

by PhRedSonya on May 21, 2019
Erotic Couplings

Author's note: This story is dedicated to my sweet friend Michael. *** I sit at my makeup table making myself ready, and I have to continually be mindful of my hand wanting to drift down to my crotch and begin rubbing myself. We have been emailing quite steadily and finally we are going to meet in person, so you can take me high heel shopping. The fact t...

The Boot Fetishist

by bootsandheels1 on Aug 18, 2017
Fetish

It was Friday and I had the day off as holiday, I had already planned to go to my favourite fetish club that night with my friends and I thought buying some new fetish gear was a must because I wanted to treat my self. My name is James and I work in a large insurance firm, my best friend and club buddy is a girl called Carla who I had known for a while now....

Transformation to Julie Ch. 01

by muffinstud on Sep 13, 2017
Transsexuals & Crossdressers

It started innocently enough. My new girlfriend, Kallie, was doing a beauty course and needed someone to practice make-up on. "Keep still while I pluck your eyebrows," Kallie said. "Ouch, that hurts," I moaned. Pretty soon my eyebrows were perfectly shaped. "I'm not sure about this Kallie," I berated. "You'll look great," Kallie replied. "That's what I...

The Footjob

by Apollo3000 on Sep 11, 2017
Fetish

For some time I'd wanted my beautiful girlfriend Carolyn to give me a really unforgettable footjob. As a committed foot-fetishist, it was one of my biggest fantasies. And Carolyn knew it. So when I received an SMS message one dull afternoon in the office saying, "Tonight's the night you get my beautiful feet on your hard cock :) C xxx", I almost came there a...

Edged in Public

by yorktvjane on Jul 15, 2020
Transgender & Crossdressers

So, my on/off BF is mad on my legs and feet, he likes to see me wear nice heels in public and loves me to tease him in public. Just lately things have taken a twist and he has a new thing he likes. It started about a year ago, we were walking by a quiet river side path just of the main Street (North Street) in York center, it was about 8pm at night and it h...

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...

My Own Heaven Ch. 17

by DaniSub215 on Sep 13, 2017
BDSM

This story is fiction based loosely on people, places and events mostly from my life. I strongly suggest that you read the previous chapters before you read this one. I have received very little feedback and I wonder if there is anyone out there reading, and if there is no one reading my work, why should I bother? So, if you liked, disliked or have ideas f...

Susan Russo's heels create a cuck

by profperverse on Dec 3, 2019
Fetish

The minute I spotted them under her desk my fetish kicked in. They were sexy red high heels and their allure to a fetishist like me could not be denied. I had walked into her office just after hours to drop off a file she needed. Susan Russo kept the heels in the office to wear but stored them under the desk when she left for the day. They were only worn in...

Kitty's AssKissing LegBoy Pt. 04

by KittyZateez on Sep 12, 2018
Fetish

My legs were sticking straight up in the air as I laid back on the bed. My LegBoy was standing in front of me, naked except for the pair of sexy, satiny pink sissy panties he had on, which covered up his achingly erect cock. His wrists had been cuffed behind his back to restrain him and prevent him from pleasuring himself, and the pantyhose leash was still a...

Teachers Are People, Too

by Wicplx on Sep 13, 2017
Fetish

I've been in education for a number of years. Before I was married I had some fun swinging experiences as a single male. I've always had a thing for women in heels and hose. They've always fascinated me. About ten years our school hired a new teacher, named Tiffany. She walked in during registration day wearing a white pant suit that fit snugly in all the r...