Gay High Heels Stories

10,724 results
Orientation
Length
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Infinite Scroll

Workout Partner with Benefits

by dre_jones on Sep 19, 2017
Gay Male

This story is a work of fiction. All characters are fictional. This story is for adults and not to be read by minors, all characters depicted are over 21 years of age. If you like this story please vote, leave a comment or drop me an email! XXOO - Dre * 4 Days a week, every week, that's the schedule. I started with the usual warm up on that torture device...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

A Sinner's Love: Redux

by SusukiRedd99 on Sep 14, 2017
Gay Male

Hihihi! Finally up~ Enjoy lovies. Leave feedback please~ *~*~* Chapter One December I'm cute. Everyone calls me cute or adorable . With my wide and innocent looking eyes, my height at 5'3(though I'm twenty one), my almost-white blonde, past shoulder length hair, my creamy and slightly pale skin tone, the fact that I look so small and delicate (fuck,...

Was I Raped? Ch. 03

by eviltwin52 on Sep 14, 2017
Gay Male

How can one describe the sweet feel of total surrender? There is an eroticism that comes with giving up all pretenses of free will and completely submitting ones self to someone more dominant. I know that feeling. Daddy claimed me as his and after the initial fight for survival I have allowed myself the sublime peace that comes with knowing that another, st...

Bringing Out the Sissy in Fred

by 0ra1Master on Aug 18, 2017
Gay Male

"Yessss.., ooh yesss, aahhh! yesss! That's it! Thaat's iit! God it feels good, so good! Ohh Sammy! Fuuck mmee! Yessss, yessss, fuuck, fuuck, yesss!" Mary Pats nails were digging into my shoulders; her ankles were hooked on my ass cheeks. I wasn't sure who was riding who but it was what it always was, a great fuck. "Give it to me Sammy! Harder...., h.a.r.d.e...

Turning the Teacher

by Dave933 on Aug 18, 2017
Gay Male

The youngest of three boys, I guess you would have expected me to get used to the sight of the male nude. But my parents were real prudes, and went on about nudity being dirty. They never really differentiated between male and female nudity, so I never did either. I realised that I was bi as soon as I was old enough to learn about sex at all. There weren't...

Slave To The Black Man Ch. 1

by tiedNbound on Sep 15, 2017
Gay Male

Oh God, I could feel his thick cock beginning to press against me. He had greased me with K-Y lotion all over my asshole and his cock, and now I was on my hands and knees about to receive him. His cock head slid against my ass cheeks, seeking that warm, special spot. He moved it upwards until it caught the my crack, and a slight gasp left my parted lips as...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...

Becoming a Gal Friday Pt. 04

by Showoff888 on Sep 14, 2017
Gay Male

Here I am wearing stiletto heels, thong panties and a matching bra. I just got hired in this work/live job for two Gay bosses. I must be drunk, cause I can't believe what I just did. I actually sucked his huge black cock! What the fuck is happening to me? I'm stunned. After sucking him, he pulled out and gave me a facial! His goo was all over my face like on...

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...