Gay Heels Stories

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Joy of Jonathan Pt. 03

by Showoff888 on Aug 18, 2017
Gay Male

My name's David a thirty something white guy who's had a bad string of uncooperative white woman and so I'm returned to my college days of jacking off with guys. I am completely naked with my cut cock bare smooth and bare, lying all soft and flaccid between my legs. I'm still all mellow from having had my guest jack me off. Jonathan's sitting next to me, thi...

How You Seduced Me Ch. 04

by married_but_curious on Sep 14, 2017
Gay Male

I groggily wake in the dark to find someone spooning against me. At first I think it's my wife, but the skin feels so much hairier than any woman I've ever fucked, and underneath I feel lean hard muscles rather than her soft curves padded with feminine plumpness, and then you cuddle closer and your cock, semi-hard from the jolt of testosterone all men get in...

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,...

Becoming a Gal Friday Pt. 02

by Showoff888 on Sep 14, 2017
Gay Male

Here I am a normal twenty year who had everything, living with this thirty year old babe who loves to be fuck, working at her law office, living with her. An ideal gig and then wham! She dumps me for some rich guy her own age. So things were getting desperate for me and I had to find a new job and place to live. That's how I came to be getting drunk, sitti...

Becoming a Gal Friday Pt. 05-06

by Showoff888 on Sep 14, 2017
Gay Male

Oh my god! I'm naked except for a pair of slutty fire truck red platform high heels, you know the kind you call 'fuck me shoes'. I'm on a bed with David this great looking black guy and Saul, his white gay curly brown hair partner, with the dashing goatee, kind of a Jewish swashbuckler thing going with that goatee. Saul and David are built tall and solidly m...

Summer Job Pt. 02

by Showoff888 on Sep 25, 2017
Gay Male

I'm a white almost nineteen year old virgin. I'm 5 feet 5 inches, I got a six inch slender cut cock when its fully erect. When its flaccid it's a small thing about an inch or so. An average sized ball sack when it hangs down, when it's cool and I'm not aroused it shrinks about to about the size of a half dollar, maybe even a quarter sometimes. I'm just a you...

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...

Daniel's Initiation

by dhope75 on Aug 18, 2017
Gay Male

Daniel walked slowly across the room to the chest of drawers as Roger had instructed him to. He opened it and looked inside. There were several bondage-style items present, including a couple of lengths of strong-looking rope, what looked like a blindfold and of course a leather strap, curled up around itself. When he saw it his heart sank - even though Rog...

Buster and Me

by seattledon on Aug 18, 2017
Gay Male

My neighbor knew I really needed some income and he knew I was good with dogs, so he recommended me when a new guy at work mentioned he needed someone to walk his dog every afternoon and sit with it on weekends. I opened the door the next afternoon to find a beautiful boxer named Buster sitting there at the heels of an equally striking man with a salt and...