Gay Embarrassing Stories

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I Hate My Master Ch. 17

by maxpotter on Jan 16, 2019
Gay Male

It was another embarrassing ride. I was feeling Timmy up and begging to be fucked. I unzipped my pants and humped the air. "I need you to fuck me so bad Daddy." I could see the driver grimacing, but he didn't say anything. Timmy ate it all up, all my submissive horniness for him. I had been ordered to be the best date, so that meant I was going all over him....

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...

Alex and I Ch. 02

by dagan732 on Aug 30, 2017
Gay Male

The next day I left for work early and had to walk since Maryellen took the car the night before. I worked with Alex the entire day and had no more embarrassing moments, though I did get some good staring time in. Most of the morning passed with only a little conversation but when lunch rolled around, we sat together and started talking. I found out that h...

Old Man Discovers... Ch. 43

by tnwriter on Sep 14, 2017
Gay Male

last sentence chapter 42-"I hope you didn't do it for me" "OH, hell no. Well maybe a little. The gut was beginning to become embarrassing and the chicken neck was a disgrace. I was surprised at my recovery time. It's such a new me that I'd love to parade naked in front of the ex," Fred say's. "Well, you can parade naked in front of me anytime," I say. Fr...

First Time Surprise

by davidshepherd on Sep 16, 2017
Gay Male

This is a true story. My wife had a friend at work who was gay. He kept asking her to bring me to his place to have dinner with him and his partner. It was getting so it was embarrassing if we kept making excuses so I reluctantly agreed that we should make a date. I wasn’t homophobic in any way, it’s just that I didn’t really want to be spending all night i...

The Golf Trip

by TonyB on Sep 4, 2017
Gay Male

It had been 6 or 7 months since my buddy Mark had caught me fucking his wife Melissa. That had been both an exciting and embarrassing event for both of us. He wasn’t so much angry as hurt but we had several long conversations afterwards during which I explained to him how it happened and that I loved both of them very much. I think he understood the chain of...

I Never Knew

by calicosmogal9918 on Aug 18, 2017
Gay Male

"You coming or not?" My friend Justin was always so pushy! I was on my way to the Graduation Party in hopes of getting lucky. It was embarrassing being eighteen and a virgin still. I wanted to get laid so bad but no girl wanted me and I was getting desperate for some pussy. I would take anything, just putting that out there. "Yeah, come on." I said and I f...

Sailing Away

by robertreams on Aug 18, 2017
Gay Male

It all began at my eighteenth birthday party. My parents just would not believe that I was through with all that juvenile 'birthday' stuff, so I had to endure one more embarrassing round of phoney smiles and worthless gifts from all my parents' family and friends. I am, I have learned since, a fairly attractive guy. Short, about 5'7" and slim but not too ski...

An Unusual Encounter

by mangagirl on Aug 18, 2017
Gay Male

Hey baby, just thought I'd tell you something, something bit strange that happened to me last night. Don't really want to tell anyone else about it, cos it's a bit embarrassing. I was on my way back from work, and as I got out of the station, 2 men came up to me. They asked me where I was going, so I told them that I was going home. They kept on walking alon...

Grandpa's Surprise Visit

by timmywells on Apr 3, 2019
Gay Male

This story takes place in a sleepy town in upstate New York. ***** Chapter One: Busted. It was the most embarrassing moment of my life; and that's saying something when I think back at the many humiliations I suffered through as a teenager. When having your own mother catch her boyfriend in the midst of taking you anally comes in second, the winner must b...