Gay Shemale Mistress Stories

370 results
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Delivery Man Gets A Tip

by jayce421 on Aug 18, 2017
Gay Male

Working for a local liquor distributorship you don't get to choose your routes or accounts, and being the lowest man on the Totem Pole you get even fewer options. So when I was told that my new delivery route was in the gay section of the city, I had to go. After a few weeks of getting the hang of where each place was and what times they wanted me to show u...

Thomas's Long Hard Night Ch. 01

by wanderinjoekidd on Aug 18, 2017
Gay Male

He should have never gone to the bookstore in the first place, he should have just went on home to his wife, and listened to her bitch and whine about ... whatever. But, he went, and was he ever sorry now. He had cum in his hair, on his face, in his ass, and he wasn't sure where his underwear or his socks were. And the taste in his mouth was awful! The man...

My First Gloryhole Visit

by Gregjm on Sep 14, 2017
Gay Male

I visited a gloryhole for the first time last week. I was not very experienced as I have only sucked off a few shemale escorts before, and they usually don't cum because of hormonal treatments. But I was quite curious after reading about them on the web. I chose 11:30 on a holiday Friday in a sex shop. When I got there, there were a number of cars in the lot...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

Cum on Panties

by jakladd on Aug 30, 2017
Gay Male

Cum on Panties - Our phone sex is always so hot, you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings & high heels, telling me how perfectl...

Husband Anon Chance

by Open4Husband on Mar 9, 2020
Gay Male

There I was with a cock in my mouth for the first time ever. I was in a stall at Denver International while my wife was likely at our gate waiting for me so we could board the plane. None of that mattered much to me at that moment. I was given this chance. I was given a chance to live out a fantasy. I was given a chance to earn the approval of the owner of t...

Curious and Horny - 22m

by toddmac781 on Dec 25, 2018
Gay Male

One night a few years ago, bored and horny as usual, I found myself stroking my cock to some porn and decided to peruse Craigslist. The usual posts were there. Old guys trying to find some younger cock, a few weirdos, and the usual straight guys testing the waters. One post stood out to me. 'Curious and horny-22m.' I clicked on it and very frankly he expla...

On a Run Ch. 01

by yeaimbored on Sep 16, 2017
Gay Male

I bent over to tie my shoe when suddenly I felt a hand on my ass and a voice say, "well what do we have here Johnny?" I instantly tried to stand up, but another hand on my back pushed me back down. "You'll stay there for now, I like the view," the man said as he rubbed my ass through my spandex running shorts. I was terrified, I knew there were at least two...

The Long Trip

by TheBlackStallion on Mar 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is my first story, please give me some feedback. Parts of this story of true, some of it isn't. I'll leave you to decide * I've been a young sailor for almost two years now. We've been at sea for almost 75 days. Tomorrow we will be pulling into Thailand. It's been a long ri...

My First Cock in Years

by Bostonsnowball on Aug 18, 2017
Gay Male

As I was driving home after a weekend away, I started thinking about going to the Paris Theater. I was feeling very aroused since I hadn't jacked off in several days, I needed to feel a pair of lips on my cock. I had been there before and always had some guy slobbering on my cock within 15 minutes of walking through the door. I parked as close as I could, t...