Gay High Heels Stories

10,724 results
Orientation
Length
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Infinite Scroll

Being Robin

by DoktorXenolite on Oct 6, 2020
Gay Male

My Name is Bob. Today I am very comfortably bisexual. I have had relationships with both men and women. Yes, I am a bit of a metrosexual, but most people don't tag me as gay, just well put together. I am handsome, but not chiseled. Thin, but not too thin. At five foot six, I'm on the shorter side. Women like me both as a friend and as a sex partner. So do a...

Halloween Kink

by toddstop on Aug 18, 2017
Gay Male

"Hurry up, babe, we have to get going," Jared called through the door. I had to grit my teeth and tear my eyes away from the mirror to answer with, "Just a minute." The matching costumes had seemed like such a good idea when I came up with the concept. Now, staring at my reflection, I wasn't so sure. Too late now, I told myself. It was our first Halloween p...

Given Away

by sissy11 on Oct 5, 2020
Gay Male

Growing up it was always just me and Daddy. My mother left us when I was an infant and my Father never forgave her. He never forgave women at all, and avoided them as much as possible. Daddy was a religious man, and held many traditional attitudes and the roles of the sexes. He believed that men were superior to women, and that the inherent God-given right...

Pauletta Defends His Title

by Boxlicker101 on Aug 30, 2017
Gay Male

This is my entry in the Literotica Halloween Contest. I'm late getting it in, so I will quickly need a lot of votes, hopefully high votes, to win any prize. * The city of San Francisco is almost certainly home to the most beautiful drag queens in the world, and every Halloween there is a competition to determine who is the fairest of them all. Paul Porter...

Getting . . . Educated Ch. 08

by sr71plt on Sep 14, 2017
Gay Male

While I was on my way to play tennis with Ben the first time the day after I had been taken several times during wrestling practice, I learned just how much of a hold Coach Seeman had over me. I was strolling along, racket case under my arm, when a big black limousine, with smoked windows rolled up beside me, the driver's window rolled down, and a big black...

Peter the Queer Pt. 01

by ThisGun4Hire on Feb 6, 2018
Gay Male

PART I: BAD BOYS GET PUNISHED "Close the door behind you," he said. He looked like he could have been a fireman in his younger days. That's because he was large with a big body frame. Perhaps he had been in-shape at one point but now he was a decidedly heavyset man. Because firemen, when they reach a certain age and become fire chiefs and sit behind desks i...

Fair Is Fair Ch. 05

by bgdddy_2000 on Sep 18, 2017
Gay Male

This is a story of married men having gay sex and it's pure fiction. If you are offended by this kind of story, read something else. Any inference to actual people is purely coincidence. Since this is not reality, safe sex isn't practiced. In real life, always use condoms and practice safe sex. ***** Here I was on my knees, with hard cocks pressed against...

A Boy, a Daddy and two Tuxedos

by ThomasStevenson on May 21, 2019
Gay Male

"That suit makes u a horny little lad, doesn't it?" It was another text from Mr Matthews. Thomas was out at a bar with his co-workers, and he'd just sent Mr Matthews a picture of what he was wearing: a fine navy pinstripe three piece suit with a bright pink and blue striped tie and a lavish pocket square spilling out of his breast pocket. So Thomas texted...

Amish Fun

by Michele G on Aug 18, 2017
Gay Male

I'm Michele, a 19 year old cross dresser. I enjoy going for long drives out in the country side. Sometimes I would pass farms where there were young Amish men would be working. On hot days the men would take off their shirts as the toiled in the fields. I almost wrecked on a number of occasions staring at them and wondering what it would be like to have one...

My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...