Gay High Heels Stories

10,724 results
Orientation
Length
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Infinite Scroll

A Night at the Club

by keptsissy on Sep 16, 2017
Gay Male

"Did you make a mess in your panties? Let me see." I stand in front of him. He's seated at a table in the back of the bar. He smiles, a dirty ogle more accurately, toward the man seated to his right. He looks back at me, sees my nervous reaction. He shakes his head with a somewhat disgusted look on his face. He reaches out and takes the front of my short sh...

Becoming a Gal Friday Pt. 01

by Showoff888 on Sep 14, 2017
Gay Male

At eighteen I fell in love head over heels to the hottest babe I ever met. She was ten years older than me and well, the sex was amazing. She took advantage of the fact that I was always horny, had stamina and could just as easily get hard again to go as many rounds as she wanted. But I guess I was just a passing phase with her, I was merely her boy toy....

Call Me an April Fool

by robertreams on Aug 17, 2017
Gay Male

Call Me an April Fool [A satirical attempt to fit into as many Literotica categories as possible.] by Robert Reams Many thanks to Pilot and one other for editing Goddamn! Shit! I am so pissed off. Who the fuck ever invented April Fool's Day anyway? Fucking asshole. Even so, how could she have done this to me? It all started last Friday, March 27th. I s...

Black Forest Panthers Ch. 02

by chibicakes on Sep 25, 2017
Gay Male

***Thank you everyone for all your kind words and feedback. I really do appreciate it. I am submitting this self edited story because I did not want you to wait longer then you had to for part 2 but I am in the market for an editor/proofreader so if you know someone that knows someone that knows something send me a message ;)*** Enjoy xoxo C. ***** -- K...

How I Became a Sissy Pt. 02

by Yngwhiteboi on Jan 16, 2019
Gay Male

I wake startled and suddenly remember where I am. I feel the weight of Abduls arm on my waist. I gently pick up his arm and lay it next to me. He rolls on to his back, now snoring. My asshole is sore and I have an incredible urge to empty. I slip out the bed, look at the clock, it's only 0530. I creep to the bathroom and close the door. I turn the light on,...

Little Sex Toy Ch. 07

by keptsissy on Sep 26, 2017
Gay Male

The cum all over my face mixes with the tear smeared eye makeup. It's running down my cheeks. It's in my hair, on my neck, I'm covered with cum. The first man that came in my face came huge. He choked me too, deep throat fucked me and made me cry. I've been crying and tearing up ever since. That was three hours ago. He had very large spurts that soaked me,...

Lunchtime Visitor

by MitchCapslock on Aug 18, 2017
Gay Male

All comments and critiques welcome. * The lock cylinder didn't provide its usual resistance when I twisted my front door key. My condo door swung open and I saw a man's dress shirt and slacks folded neatly atop a pair of polished shoes on the stairs. It sounded like the TV was on in the den. As I came around the corner, I saw Jim, the man who had been fuc...

David and Annie Ch. 01

by electricblue66 on Aug 18, 2017
Gay Male

Hey David, that thing we talked about, are you still up for it? Send me your address. Time? Will you be alone? Yeah? Cool. Looking forward to it. Ah, there's the street, what number again? I check the scribble note on the dash. I pull up down the street a little, and walk back to his place. Might as well be discreet. Oh look, a condo with what looks like a...

Tethered and Feathered Saga Ch. 01

by doctrtic on Oct 15, 2017
Gay Male

I was thirty-one years old and was addicted to pantyhose and nylons. Various girlfriends over the years have indulged my fetish, with pantyhose sex, nylon foot jobs, and some would let me smell and kiss their pantyhose covered feet. Something happened during this time that was mind blowing. I was over at my friend Nick's house. Nick is am openly bisexual ma...

Nowhere Railcar Diner

by KeithD on Oct 26, 2020
Gay Male

Sue's 1962 red Impala convertible had a pillow in the backseat, which Eddie Perry found quite convenient to place under her lower back so she could comfortably recline in the back corner of the seat behind the driver's position. She was maneuvered so that she could spread and bend her legs to enable him, naked, to take most of his weight on his knees, betwee...