Any of you who may recall the Times Square area on the late 70s early 80s...it was a cluster fuck of wild sex scenes.
One studio a brothel that advertised "Take pics of naked ladies" (for art sake) A couple of naked women were standing on a small stage while a naked lady showed men how to work the camera. The woman standing there on stage talking had a long stream of cum hanging out of her. The woman talking to me kept signaling her but to no avail! At a BDSM dungeon, I recall being tied naked to a bench and having two women walk in on the Domme and I and proceed to argue with her about who had the forceps, and where they were. Another time a Domme decided we were in the wrong room and had me carry my clothes to a new room , naked though a hallway past 3 women who were standing talking, I assume employees?
I doubt anyone seeing Times sq area today can even imagine how wild it was.

 

Not that anything really happened but one of my most awkward experiences was at my sister's neighbor's pool when I got out of the water and to my surprise I had gotten a boner which was poking out one leg of my shorts a bit lol

I hadn't realized I was hard or anything so I didn't think to cover up before getting out - not only was it awkward it was showing but also because of what they might think about why it was hard at all Lol

 

When I was in highschool playing football,got showered...and love laying on cool sheets on my bed after a workout,close my eyes and feel the naked breeze on my cock and body,that day my aunt was over for the weekend,saw I relax I was .as I lay there next thing she is sucking my cock full animal,then rides me till my balls empty in her...she put her finger to her lips shhhh..clean my cock they left...OMG all weekend surprise and shhhh...she wanted to be seeded and breed...and was...

 

Great topic and there is so much I could share but I'm just going to hop to the most extreme thing that came to my mind despite the subject matter definitely not being for everyone... consider yourself warned.

Most awkward thing that came to mind immediately when I saw this topic... watching on as a female friend of my wife and I was tied to our dog and suddenly discovered she was allergic to dog cum. That turned into an awkward night.

 

the most embarrassing thing was when I was in the bathroom masturbating and my sister came in... we are not ashamed because we have always been naked together since we were little because we grew up in a nudist family... when she came into the bathroom she made me told not to worry and to continue that she wasn't interested... now I happen to masturbate even while we talk and we are no longer ashamed..

 

One weekend last year I knocked on the door to meet my client. The guy that opened the door was someone that had been a bit of a jerk when we were in high school together. We did get past that and had a good time

 

When I was a teenager...I brought my girl home thinking no one was there...play some music.. dance...we started to grind and hump...just I I was ready to pull her pants down...who walks in my dad...he had one finger up...and saying ...no...no... OMG I was sooo horny then...I rush her to my car got a bj

 

I was talking to an old friend and I did not know his wife was nearby when I started talking about "Remember When..."

 

a recent weekend I spent with my brother in a nudist/swingers campground.it was Labor Day weekend we spent the three days naked and enjoying lake and playing volleyball and fucking around in the open park. During the evening many people sat around the parks fire pit. As you can imagine many people were there naked and some of them were having sex. I began to giving my brother head. And I was naked and I got on all fours and was deep throating him (if your gonna do a job do it well) People ask if we were related, he told them that he was my brother (we do look alike) I also told them the truth. As I continued to sucking him. All of a sudden I felt some warm drops on my back and ass! I looked up and a group of guys were beating off around me. Now I was into something I didn’t expect but I loved this and continued to play with my brothers cock and beatoff a few more cocks. Even women were beating their men over me.. I finished my brother and swallowed in front of the whole group. I was covered in cum it was dripping down my legs and my asscheeks my asshole even my hair was soaked. We had a standing ovation as He and I walked down to the lake to wash all these guys off. I really enjoyed being the center of attention and so many guys enjoyed them self’s!

 

Before my first FWB became my FWB, we got caught with me pulling her shirt off and her pulling my cock out. We finished a few months later. I had to go across the street the next day to apologize.

 

A few that come to mind:
Fucking a racist Jewish lady... best course of action was gagging her with my cock to shut her tf up.

Double teaming a pizza delivery chick with my buddy

Fucking strangers always feels kinda weird

Orgy at a music festival

Getting jumped by some white trash dude and his buddy after banging his ex

Testing out some erection inducing gummies for the lady who runs a porn shop near me, and then having people watch me fuck her.

 

In college I was the editor of our college newspaper and a BMOC so it was not unusual for me to get 'hit' on by coeds. Always made me feel a bit awkward, though, especially when I hardly knew the gal. One of my editors had a town home close to campus and asked me to meet him there at noon one day. When I showed up, he wasn't there, but his girlfriend was--a very hot, slender but curvy blonde who chaired the university's inter-sorority council and had a rep for being promiscuous. She tells me that she and my friend had just broken off their relationship. So she was looking for a new partner and tells me point blank: "You can have whatever you want, whenever you want it, no strings attached." OMG! I was sorely tempted to just sling her over my shoulder and carry her off to the bedroom then and there. But I had just started dating the gal I eventually married years later, a foxy brunette sophomore and I didn't want to jeopardize that relationship. Moreover, though I had met my buddy's gal on a few occasions, I did not know her well. So I passed on the opportunity. Told her I was very attracted to her but just didn't feel any emotional connection between us and was seeing somebody else at the time. She seemed surprised by my reaction, but was a good sport about it. May well have been the first guy that ever turned down sex with her, who knows?

 

Wasn’t aware that a mom came homes d walked in on me and her daughter fucking. She was in top of me riding away then mom grabbed my cock and pulled it out of her daughter. Saying she’s not ready to be a grandma and everything. Giving us a lecture while we’re there naked. Then when she finished the daughter says “mom you never took your eyes off his dick” mom said “well it’s big as fuck I’m trying figure how all that fit in you!” She came back a few minutes later and threw condoms at us.

 

going out on a pontoon boat my uncle built from a kit. in the middle of the lake the motor came off and we started sinking. lucky someone was close as the boat went down like the titanic

 

Was crossdressed in my mother in law's panty, bra and swimsuit when they were out of town. I stopped to check on the house. Her things were smaller and quite snug. I was rubbing one off when I heard someone unlocking the door. I only had time to throw on my jacket that was close by. I stood behind the kitchen island in the dining room when in walked my sister in law and her husband. They were driving by and wondered why the lights were on. I stood frozen hoping to not get caught. They thankfully stayed in the kitchen and didn't notice. I'm sure they noticed my nervousness. After a quick chat and explanation of my doing there they left. I soon followed

 

I guess that would be when I was jacking off to porn in the garage while my Parents were gone ( it was where my porn stash was , this was the 70’s )
And a neighbor guy catches me . This was a few years before I could drive

 

did you tell her mom or keep the secret?

 

I was out with my friends once, and some random girl started talking to me. We chatted well into the night about "normal" things. Then I tell her that I'm leaving with my friends in 10 minutes, and she kisses me and starts touching me all over!

That was wonderfully unexpected... and the start of a friendship that I will hold dear to this day.

 

Remember one night in Highschool I got home about 3am walked into house and startled my dad as he was headed to the bathroom. He flipped on the light looks at me all he says is you working nights as a clown. Goes in takes a piss the whole time I'm just bewildered by his remark. He walks out looks at me shakes his head goes to bed. I go in to bathroom to shower I look in the mirror my face is covered with menstrual blood from gal I had gone down on before dropping her off and comming home. Was a lil awkward talking to him next morning. Lol we joke about it now.