Gay Heels Stories

2,228 results
Orientation
Length
Source
Infinite Scroll

The Warden

by TheGoodSick on Sep 14, 2017
Gay Male

Bryan walked away for a moment and left me standing in the shower. I dried off like he told me to and sat down on a three-legged stool. Only a few minutes had gone by when he came back through the door. My massaging had me relaxed and content, but the sudden loud jerking of the door startled me. Bryan carried a box over and put it down on the desk with a thu...

My Lost Date

by Freakalicious on Aug 18, 2017
Gay Male

Thanks to LadyPineRose74 for the fantastic editing! * I was supposed to go out with my man-friend, after work, the other day. I was hopeful that he was going to take me out to this amazing Mexican place that he talked a lot about. I rushed home, jumped in the shower, and was ready in twenty minutes. I wore this super short, black skirt, a tight white shirt...

Jason's Costume

by nylondad on Sep 17, 2017
Gay Male

The following story is true. It occurred fifteen years ago. By virtue of the fact that yesterday was Independence Day jogged my memory. I had married a woman with three sisters. All but one of the sisters had kids. The oldest sister Carolyn (my sister in law) had a son by her first husband named Jason. He was a pleasant kid who grew up in with Carolyn and h...

Pantyhose Seduction

by nylondad on Sep 17, 2017
Gay Male

I was single and aged 26. I had been engaged for two years to a beautiful woman but the relationship had gone stale for each of us. We had lived together in a garden apartment for two years and she chose to move out and was staying with her parents until she could find a new place. I was sad as I missed her but felt relieved with the knowledge that the word...

My Hot Uni Roommate Ch. 05

by CreamStuffedTwink on Jun 17, 2019
Gay Male

Previously: "Want to watch a movie or something?" he asked. "Sure." I went and sat down on the couch while Michael stood with the remote and cycled through Netflix until he found something he wanted to watch. I expected him to just sit next to me, but after he sat down he pulled me over to him until he was lying down with me as his little spoon. My skin t...

Where Do I Start? Pt. 03

by MarcusVindictus97 on Nov 20, 2018
Gay Male

Saturday I slept most of the day recovering from my night with Bandit. My throat was raw from all the deep throating I had done. I got out of bed and grabbed a beer to cool my throat. It felt really good as the cold beer slid down my throat. I checked my stash and saw the ½ a kilo, the deering, and the spoon as well as my weed and rolling papers. I smiled....

Vampire LaCour's 2nd Coming Ch. 05

by sr71plt on Apr 3, 2019
Gay Male

Ham LeMoynes couldn't sleep, and he thought he heard a noise from downstairs. Probably only one of the many ghosts haunting this old, rotting mansion, he thought. But, still, he was fully awake now. He rose off the cot he'd set up in his room until after everything was packed out and padded down the stairs into the music room. He was barefoot, only wearing h...

A Fantasy of Mine Ch. 02

by ima_milkwood on Nov 12, 2019
Gay Male

I say yes, and widen my stance to bend over in these heels. The weight of the tits pull me down and the counterbalance of the ass levels me out, I have never felt so sexy. So desirable. Basically on my toes, with my ass pushed out snorting up the first line of whore fuel. I tilt my head back and take a huge snort to make sure I got every grain as far back in...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

His Slave Boy 'Good Wife'

by keptsissy on Sep 19, 2017
Gay Male

I called before I got home. He answered on the first ring. He knows better than to not answer immediately. Before he could say anything I cut him off in mid-sentence. "Naked, at the door in just a pair of sexy heels, nothing else, I want you. I'm hard in my pants thinking of your submissive little ass. Your makeup and hair better be perfect, little boy, fuc...