What's the most embarrassing, sex related, thing that's happened to you?!

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In my late 20s i'd recently broken up with my GF, me and her best friend had always clicked and there was undeniable chemistry, one thing led to another and we started fucking. SHe was 20 and lived with her mom in this tiny house, i stop by one day and we end up hooking up in the living room, i've got her bent over the couch fucking her brains out, she reaches orgasm and in turn i blow my load, she blurts out something like "oh god i love your amazing cock" as i pull out and become a bit more aware i notice someone standing in the kitchen and its her mom completely stunned looking then blurts out "oh jesus christ!" then turns and leaves the house.

Couple hours later she texts me and says she just had the most awkward conversation ever with her mom and to top it all off the mom thought i had a nice cock from what she saw, more awkward for her than it was for me but funny none the less

 

When I was twenty four my girlfriend wanted me to let three of her friends watch me suck a cock. That was not easy, I was still very shy about my body and bisexuality.
As usual I gave in to her request and found myself really turned on by the situation after I was going through with it.

 

I have been walked in on while having sex numerous times, never really embarrassed. One time even the mother-in-law of married woman I was with. which that was the only time I stopped.
I might have been embarrassed more the time my dick was hanging out of my shorts by accident, and a couple of women seen it. They were women I knew, but they thought I did it on purpose.

 

Years ago I was experimenting in my sexuality and went to an adult video arcade, once my eyes adjusted to being in the dark I noticed there was a glory hole. I didn’t think much of it and started to stroke my cock while I watched the video. I could hear someone enter to adjacent booth and could see a guy looking through the hole. Being a bit of an exhibitionist it kind of turned me on knowing I was providing a show. Soon he motioned for me to put my cock through the hole, and I did. I felt a nice warm wet mouth start to suck on it and it felt really good. Suddenly I heard the door open to his booth, and voices saying things like “oh my god, what are you doing?” “Oh shit! He has a cock in his mouth.” “Shut the door!, did you see that?”
Evidently the guy came with his friends and he forgot to lock his door when he came in. His friends thought they might catch him jacking off or something, instead they all got a full view of him with my cock in his mouth. He completely freaked out, was cussing up a storm telling them to close the door and from the sounds of it they were very shocked at what they had just seen.
I obviously pulled my cock back through the hole. Being it was the first time I had ever done anything like that, I was freaking out too. decades later it’s easy to laugh at it now.

 

I nearly had a heart attack when my wife and I swapped with another couple. I had to have two stents installed.

 

A frequent concern I have is what if a serious medical issue arose as I was with a sex partner. Especially one I have paid to have sex with. As we age issues like heart trouble, stroke, or physical injuries can happen easier. I just hope they don't happen while I'm in the middle of a encounter and have to explain why I was where I was at the time. That would be more than embarrassing to say the least.

 

Being that I seem to have a humiliation fetish I have been in quite a few embarrassing situations.
1) naked in front of several clothed people
2) masturbating in front of others
3) giving a blow job with an audience
4) walked in on while being fucked
Despite the deep humiliation that I feel I am also very turned on.

 

My worst one was on a saturday morning and we were ripping into it in missionary position, luckily with a sheet over us. I looked beside the bed and standing there were the three boys, very young, wanting breakfast. I don't know how long they were there. I froze mid stroke and tried to pretend everything was normal. They could have been there for goodness knows how long.

 

We used to camp in a pop up camper. Being in such a tight space we had to improvise which we did well. So I thought. Once we would get the kiddies down for the night we'd hang out by the campfire for 30 minutes or so before heading to our bunk. The temptation was usually to great and we went at it before falling asleep ourselves. Many years later our oldest mentioned the camping trips. He told my wife how they would stay awake to be rocked to sleep each night. We had no idea the little shits were doing this at the time.

 

My besexul wife and friends were in home and playing both women was charged . My wife call me to fuck both of them due to strong antibiotics and other mec I took I can't get hard both women were furious on me .

 

Yesterday I was caught flashing and stroking my stiff cock infront of my partner by my stepdaughter she was home from work early.

 

My OMG Moment was the following….

I had a MySpace Page that had tons of pictures and video clip of myself and my erotic kinks. I am talking 100s of picks, videos, and posts regarding blowup dolls, latex, costumes/roleplay, strapon play (pegging) and many other things. My main page photo was myself in scrubs on a leash and collar, with 4 blowup dolls, 2 wearing strapons while dressed up as nurses. My ex loved the page and I had just allowed her to be into a couple pictures that I posted. All of our pics we were wearing masked, but if you were to our house you could easily identify the rooms.

I am at work and she had her mom over one Friday afternoon. He mom asked to use her laptop to check her email and my ex though nothing of it until her mom was stone quiet. He mom had pulled up MySpace and my ex was still logged in and into my account and her mom spent over 15 minutes looking over all my pics and videos. Now this lady was a Baptist and very religious so. Can only imagine what went though her head. I mean there were pics in there of me having sex with blowup dolls, being pegged by blowup dolls while in chastity and also giving oral to dolls wearing strapons. My ex walked out and found her sifting the site and was dumbfounded and just froze before she was able to ask what she was doing.

I got home and she told me right away what happened and I was mortified…

 

A major O M G moment!!!!!!

 

my gt teased me for more than 30', just pinching and caressing my nipples, than she placed her mouth on my cock..
I exploded in her mouth after few seconds!

 

In a way it was good because you got to cum lol

 

yes it was, but was really uncontrollable! she was expecting fast, but not so fast

 

Lol yup
Better than going soft and or not orgasming

 

When I was twenty four my girlfriend talked me into letting her best friend watch me giving one of our friends a blow job.

Three days later I walked into one of my favorite bars and guess who just got a job there

 

Was fixing a friends computer and as a precaution I backed up all his photo albums and copied to my laptop.

He was a professional photographer and was petrified he’d lose his collection.

A few weeks later my teenage daughter was looking at my computer and found the backsup….. The stuff the guy had was unreal.

Not only did he have run if the mill filth, he’d also been doing nude shoots with women….some of whom I knew