Gay Humiliating Stories

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Prison Initiation

by TheGoodSick on Sep 14, 2017
Gay Male

There is something particularly humiliating about being arrested covered in cum, piss, and surrounded by big black men, especially when you were once a very well-off businessman with a simple insertion fetish. My whole private life had been exposed in a day, and it affected my professional life a great deal. My face was plastered all over the news for weeks....

Joe The Weatherman's Second Time

by sack on Aug 18, 2017
Gay Male

After Joe and Scott had their humiliating first sexual experience under the command of Sharon, it was very difficult to work together the next day. They pretty much avoided each other the whole morning, finally getting to talk a little at lunchtime. As it worked out, both men basically enjoyed the experience, but wished Sharon hadn't been there so they could...

Nerd Strikes Back

by sizequeer on Sep 25, 2017
Gay Male

The comments kept coming, like flies to a very tasty and humiliating pot of honey. The best were from the prettiest girls. I mean, not that I gave a single shit about girls, I was gay as fuck, but their comments were delicious anyway. "Lmaooo what a dork" "Maybe you should drop the books and hit the gym sometime Mike lol" "Do u even lift, brah?" I scroll...

Bookstore Fun/Online Mistress

by fun4all6969 on Sep 14, 2017
Gay Male

This story is about what I did to please my online Mistress Nikki who wanted me to do kinky and humiliating things to please her. Her goal was to turn me into her gay panty boy slut. ******** Friday ******** I left work early Friday afternoon to do as she demanded. After training me to suck cock by sucking a dildo, she demanded I take it to the next leve...

Straight to the Bottom Pt. 02

by Megahomingberry on Jan 28, 2020
Gay Male

Part 2 : Winter is Cumming On a cold winter day...about four days after my humiliating (and very gay) 'lose' to Brian...I was in the shower thinking about our bet and what happened between us. I still haven't cum to terms with the fact that I swallowed Brian's...I can't even say. Shame poured onto me like the water of the boiling hot shower. I can't believ...

Guys' Retreat Pt. 06

by Cyanlot on Sep 14, 2020
Gay Male

Part 6: Brianna, Used and Abused The humiliating show I'd been forced to put on for Kent and Vince with the two dildos had had an effect. I suspected that it had aroused Kent but I was vividly aware of its effect on Vince. His cock was hard even before I'd gotten it in my mouth. When I'd freed it from his pants, it sprang up, eager to fill my mouth. Now, as...

Office Hours Ch. 02

by IndianaRealLife on Sep 1, 2017
Gay Male

Walking home from professor Summers' office was one of the most embarrassing, humbling, humiliating and EROTIC experiences of my life. It was about a 25 minute walk through the south end of campus to my dorm and I was wearing only a short pair of blue mesh shorts which I had sweated through and used to wipe up multiple loads of cum. Professor Summers had kep...

The Contest

by Bunvotey11 on Sep 14, 2017
Gay Male

It was now on between us. One of us was going to be a winner, and the other would suffer a messy and humiliating defeat. Me and my jackoff buddy Brad were matched pretty evenly, especially where it comes to being kinky. We started off earlier as friends throughout school, but we didn't know back then that we were both could be interested in each other. It'...

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

Finding Out the Truth Ch. 02

by muntusaurus on Jul 6, 2020
Gay Male

Continuation of the first story. This story makes more sense if you read the first story. My relationship with Mandy was over after that humiliating encounter. I deleted Mandy's number and tried to delete the memory of the humiliating episode from my mind. However try as I might I couldn't get the image of Jason's huge white cock off my mind. About three...