Gay Heels Stories

2,228 results
Orientation
Length
Source
Infinite Scroll

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

Bi-Trick Ch. 02: Gay Sex Show

by KenJames on Aug 29, 2017
Gay Male

* * * * * * * * * * Note: This is a BISEXUAL story. It has female-female sex, as well as male-male sex. * * * * * * * * * * "Welcome to the 'Mile High Club.'" Brady held the door for Beverly, Kevin, and me. We stepped into the ultimate man cave. The big room took up half of the three-story mansion's basement. A giant flat screen, flanked by four smaller...

Bottomed Out Ch. 02

by capresque on Sep 14, 2017
Gay Male

When I awoke, it was dark, but I couldn't tell what time it was. For a moment I couldn't remember what had happened and why my whole body was sore and sticky with fluids. I felt my arms and legs being released from the ropes holding me spread eagle on the bed. I was shoved off the bed onto the hard floor. With one slap on my ass I was reminded of all that ha...

My Memories of David Ch. 04

by msmithyxx on Dec 30, 2017
Gay Male

##### Author's Note ######## It's been about two years since I last posted a story. I found a half done draft of this chapter and remembered how much I loved writing these, so I'm back and finding more interesting ways for Mark and David to get into naughty trouble. I hope you enjoy it. ######################### Several months had passed since the bachelo...

Rick Needed a Beer, Gets Much More Pt. 11

by Iwanttwo on Aug 12, 2019
Gay Male

This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters. —————————————————— Tuesday at the office was awkward, to say the least. I avo...

Inventory Night

by bullockhall on Aug 18, 2017
Gay Male

My name is Mike Martin. I'm 21 years old, 5' 8" tall and weigh 127 pounds. I have blue eyes and blonde hair I like to wear long. And I'm gay. I've known I was gay since I was 10 years old. I live in a small town in Missouri with my mother, a single mom. I never met my dad. Mom knows I'm gay, but nobody else does. I've always been too shy to tell any school f...

The Club

by Emma7588 on Mar 3, 2020
Gay Male

Kevin smiled as he looked at his reflection in the staffroom mirror. The black leather cut looked great against his pale skin. The shadows it cast across his stomach added definition to the abs that were slowly developing. Those long hours he spent working out at the gym were starting to pay off ... among other things. He stood back and checked out the rest...

Caught, Blackmailed and Loving It! 002

by CSK on Sep 14, 2017
Gay Male

It's amazing how one day of laying out naked can change one's life. If you haven't read my first account of how my life changed, please read chapter one and then come back. If you have read it, you will know that it left off with me and Heather making out in a pool while her father (Mark) fucked me in my ass and his friend Jack fucked her in her ass. After t...

Hotel Night

by guy_manuel on Aug 18, 2017
Gay Male

It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was...

Chauffeur The Ch. 03

by skinnysailor on Sep 14, 2020
Gay Male

"See it there? The dock? Look up the path and you can just see the red roof." With that the pilot banked the DHC Beaver float plane, circling the lake, checking for boats and the wind direction. He throttled the big Prat and Whitney radial engine back, lowered the nose and the flaps, and down we went. We'd been up since before dawn, loading Mr Nash's Linco...