Cum In Heels Stories

360,326 results
Orientation
Length
Source
Infinite Scroll

Anya Goes to Vorhees Ch. 29

by sinagainChris12 on Sep 25, 2017
NonHuman

The table was set for nine people. Five adults, three children at the table, and one child in a high chair. Anya had put out her good china and had spent a little extra on quality steaks that she cooked on the grill that was part of the professional quality stove top in her new kitchen. Her daughter had put the wine and water glasses on the table, and had he...

One Night

by mrbill4u on Sep 1, 2017
Group Sex

Back a few years ago when I was a younger man in the service. I was stationed in the Midwest very near a college town. Now at this time we were involved in something called the Vietnam War and if you were in the active service and near a college town you would not think to get lucky in any way shape or form. I am here to tell you that for this airman it just...

Denny as The Handyman Ch. 1

by denny9 on Sep 25, 2017
Mature

Author's Note: This is a continuation of the Denny chronicles. Thanks to those readers who have continued to support me through your votes and e-mails. Keep 'em coming. I look forward to reading your comments and suggestions. * * * * * I watched the rounded buns of the stunning redhead straining against the tight confines of the beige skirt and immediatel...

Chase Goes to College Ch. 03 Pt. 03

by jean_p_berri on Dec 19, 2018
Anal

Author's Note: The following is a work of fiction. It may or may not contain characters based on persons living or dead and may or not may contain actions completed by these same persons who may or may not have lived. The world where this story takes place is an alternate reality where sexually transmitted diseases and unwanted pregnancies do not exist (no...

Captain Lee's Dirty Secret Ch. 04

by Jack Green on Sep 1, 2017
Group Sex

Ch.04 Jack Green The first I had heard of Captain Lee's parties was from Sergeant Jones when she had told me how Captain Lee had recommended that she come see me in regards to her sexual starvation. Every month or so there would be a get together at Captain Lee's house, usually a barbecue, and I had always thought nothing of it. I just assumed it was a par...

The Day I Realized I Was A Slut

by sweetie4you on Sep 13, 2017
Erotic Couplings

I’m 23 years old, and am straight out of school with my Bachelor degree in Music Education. I received my first teaching job as a band director for Littleton High School, that’s in a small town in the mid-west. The first couple of months took some getting used to. Just trying to get into the groove of teaching and all of the administrations of a full band pr...

County Girl Ch. 01

by LaurenWestley on Aug 31, 2017
Fetish

So, here I was, waiting in the back corner of the garage, the door to the empty bay open. The night light illuminating the front reaches of the garage. The garage lights were off. Instead, in the shadow of the corner, I waited for him to come. Nearly a year ago I had met Master Cock on-line. This was a unique chat room, one where submissive wannabe transves...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Tranny Tales Ch. 06: Cumming in Sophia

by erectus123 on Sep 15, 2017
Transsexuals & Crossdressers

Sophia of the Bourbon Wagon – a sex change? I remember years back when coffee flavored liquor made its debut. Was it Kahlua? Maybe not. Anyway, they set up a stand inside a tent in Times Square and if you stopped and stuck your head inside, they shot an atomized spray, right through a hole in the bottom of a small paper cup; zap! –Right into your mouth. And...

Unexpected Nightcap

by shakenmartini55 on Sep 12, 2017
Mature

Author's note: A big thank you to Angel Love for volunteering to be my editor. She reviewed my work and in the process made it much better than it was originally. I believe that her insight and experience not only improved this piece, but will make the rest of my work even better. Thanks again. * It had been a perfect day for a pool party. Things got under...