Most Embarrassing Same-Sex Sexual Encounter

[Flanast]

Coming out of a bar with a few of my buddies when we are in early 20s. They are goofing with me grabbing me crotch. Guy in the parking lot asked me if I’m a fag letting them do that to me. I say no and I’m meantime my friends take of leaving me alone with him. Next thing I know he grabs me by the ear and forces me to say I’m a fag and love to suck cock. He brings me into the alley way and makes me suck his cock until he blasts his load on my face. Little did I know that my friends watched the whole thing and never let me forget about it.

 

[cdstefi]

I wouldn't say embarrassing per se, but one that wasn't repeated.

I arranged to meet somebody I'd been chatting with at short notice, another crossdresser. Turned up at his house and he was having tea out front with his wife (dressed in mufti of course) so there was a fair bit of small talk had to be made. I didn't remotely fancy him in male guise but at some point his wife went indoors to do some housework and we went round the back of his house, and I dropped my trousers and let him feel my cock through the panties I was wearing and he guided my hand to his obviously very erect penis in his joggers. We didn't have time to do any more than that and given my lack of attraction I doubt we would have, but the thrill of being desired and played with sexually was still a turnon.

 

[johnnyampleed]

In one of my earlier visits to an ABS in my 20s, I watched booth videos until I masturbated and really shot my load. When I opened the door, I saw a guy I went to school with and then I saw another guy from the neighborhood. At first I felt embarrassed, but then I realized that they were there for the same reason as me.

 

[Mason9653]

Soon after my first time sucking cock I went to a friends place to give him a blow job. I was nervous, just beginning to relax and take my clothes off when a woman I knew walked into the room.

His cock was out, I only had my underwear on, clearly tenting. She wanted to watch.

She encouraged me to strip the rest of the way. I was visibility shaking but I got on my knees and let her watch the whole way through till he pulled out and came on my face.

Seeing her around town for the next couple years always brought me back to that event.

 

[Swuchmann]

When I don’t have a regular top I will go to a hookup site to find an available guy who needs a bottom.

A few months ago I engaged a local guy, a dom top. I am a smaller fem bottom and he was a bigger top near my age. We were a good match.

We exchanged emails and pics and agreed that I would host him for some playtime. When he came to the house and opened the door I was surprised and shocked that we knew each other from 30 years ago. I knew he recognized me and I asked him in. There I was in a thong and bra staring at a man that had dated my wife 30 years prior. Slightly embarrassed I asked him in.

It was initially awkward. He had lots of questions about my wife and he let me know that he thought she was a “great fuck”. I asked if he was still interested in playing and he said yes.

We went to the bedroom where he stripped and walked up to me with his bigger cock that was getting hard and said “I am going to fuck you like I fucked your wife”. He then told me to suck him. He was aggressive and kept his hard cock deep in my throat.

We eventually worked to a missionary position where he penetrated me as he French kissed me. He then whispered in my ear…”I use to tear your wife’s pussy up and I plan to do the same to you@. He went to fucking me and wrecked my boipussy for about 30 minutes before cumming. All the while he asked me what my wife would think that she married a sissy fag…it just turned me in.

When he was finished. He dressed and headed to the door. He turned and looked at me a said “you are good fuck and tell your wife hello”. He chuckled and left.

We met a two more times before we decided it was best to let things lie. He was a good top.

My advice is, don’t be surprised if a hook up is someone you know.

 

[OlderBtm4U]

Wow. Thanks for sharing.

 

[SPARTAN047]

I have had a few moments where I tried not to be gassy in front of my sex partner.

 

[rc1989]

This predates cell phones. Older neighbor I sucked off a lot. He was sitting in his recliner and I was on my knees between his legs. I had been sucking his dick for about 5 to 10 minutes and his phone rang. I stop sucking and he answered the phone. He said don't stop and started talking on the phone. I'm licking and sucking and listening to him talk. I hear him say no I'm not busy but the bitch sucking my dick is. And I remember feeling embarrassed. He said no really and no for real. And puts the phone down by his cock while I'm slurping and moaning. Then takes it back and says she sucks my dick daily. They talk some more and he's rock hard. I hear him moan and say I got to go. He's a very verbal guy, saying suck that dick I going to cum in your mouth cocksucker. Stuff like that . He cums in my mouth and I'm licking his shaft and I can here his phone making the busy signal sound. He hadn't hung the phone up all the way.

 

[PrincessPillowHump]

The first time a girl ever ate my pussy. We were at a club. Id been drinking. A LOT! She made me cum so hard and when her teeth grazed my clit I literally pee'd on her face.

 

[LeinadVirgo]

The first time a girl ever ate my pussy. We were at a club. Id been drinking. A LOT! She made me cum so hard and when her teeth grazed my clit I literally pee'd on her face.

So very sexy. I'm jealous. Mine was at a bar trying to hook up with one of a pair of sisters, and another guy was trying to get one too. They dared us to kiss, so we did. I ended up sleeping with one later on... And the other one later later on.

 

[PrincessPillowHump]

Now that

So very sexy. I'm jealous. Mine was at a bar trying to hook up with one of a pair of sisters, and another guy was trying to get one too. They dared us to kiss, so we did. I ended up sleeping with one later on... And the other one later later on.

Now that is hot!