What’s your most embarrassing moment naked?

Two incidents, and not really naked for either, but still.

The first time I was about 13 and had just discovered my penis and that when I rubbed it it got hard and felt almost agonisingly good (e. g. my first experience of real sexual pleasure). Anyway, I was supposed to be in my room doing homework but like most boys that age who know what the tools are for, I had my pants down and was vigorously beating off. I was fully erect (which wasn't too impressive) and I was still very young, but had to move back from the table I was supposed to be studying at in my room so the head wouldn't bump into the table's underside. My door was open and behind me, and my mom came in to ask me something...!

So there I was with my tiny dick in my hand, fully erect, not even covered by the table and she could see -everything-. The -big- problem was that seconds before she came in I had started to orgasm, that hellish kind of unbearable electric ecstasy when the feeling is still completely new. Fortunately I wasn't ejaculating yet, plus a side effect (for me) when climaxing is I kind of go deaf for a few seconds - so I only became aware of her when she was standing right next to me.

I kind of leaped off the chair and dragged my pants up (still in the midst of intense orgasm) and she just turned around and left without a word. She also never said anything about it but I still turn red to this day with embarrassment. She saw -everything-.

The other time I was in the sitting room and for some reason had started masturbating, and my younger brother came in. I once again got caught at just the wrong moment, this was when I was about sixteen so I had started shooting sperm by them, and he caught me just as I climaxed. I simply could not stop, he just looked at me and my spurting penis with a kind of "dude WTF?!" expression on his face. He ribbed me mercilessly about it afterward. (But then I caught him not much later with my step-dad's porn mags jerking off his not-inconsiderable penis, so it was evens after that.)

 

My brother came over to the house one day. He always knocks once then comes on in. He walked in and saw my neighbor fucking me in the ass. No way to talk myself out of that one.

 

My mom walking in on me at the very instance my masturbatory orgasm kicked off... age 13.

And later my brother also walking in on me around 16, literally just as I'd spurted my first burst of semen while climaxing and the second spurt was jetting out.

 

Not naked but near
At a public water park with my gf and her younger sister who had a fixation on penises
I was wearing a speedo I still had from my days in competitive swimming, I was in my early 20’s
Meaning, easily excitable.

gf’s sister stared at my package a LOT!
As long as she could and she was not aware of not being discreet at the time

I don’t know if it was me just being horny in general but I know her staring did cause me several erections in public. I think it was a bit “not-as-bad” that we were in the water slides stairs instead of in the open. I tried holding m arms and hands in front to hide as good as I could without actually placing my hands on and being obvious or indecent
She managed to position herself to see the shape and size as much as possible
I was so self conscious

years later I would not have cared anymore and would have let her see all she could and even take it out for her, full erect or let her see a small grower rise and grow to a full throbbing erection. In the right circumstances

 

Same sister did the same at the beach. I was quick to get in the water to hide my obvious condition especially that this was family outings with my gf and her parents

 

I went on a hike with my bf on a remote trail nude once, ended up getting caught by a group of (4? or 5) guys that were coming the other way. Some of them were shirtless so I got some eye-candy too haha, one of them even hugged me and we laughed it off, so not that embarrassing actually. I'd say the worst one was when I was at home next to my window and my neighbor (who is a very old woman...) passed by and froze when she saw me Had to crouch under the window till she left

 

Not naked but most embarrassing was in HS
Always had erections, loose underwear.
I had to go to the front of the classroom and IT popped out of my underwear, a real tent, very much like a lone pole holding the tent.
The teacher called my name and was a deep red, I looked down and was mortified. I quickly reached in my pants to reposition it.
The whole class laughed, I was red and didn’t look at anyone the rest of the day.

 

I was wearing tight shorts during gym class and although there was anyone or anything justifying getting hard, it kept happening. I was made fun of but I just couldn’t disappear

 

Change of direction here, not embarrassed. Actually pleased with the moment.
Younger times when I paid someone for sex.
We had met before so I knew whatever happened, it was going to be very satisfying.

There were times we talked a while before doing something, sometimes we just went at it right away.

I arrived and after a friendly hug the conversation led to believe we were going to play early so I got naked. Then she mentioned she forgot something going on in her oven and if I didn’t mind waiting. I went in the kitchen with her. She was still dressed and we spoke for several minutes while she kept checking things.
I was excited to meet her ahead of time and that didn’t go away so a few times I would get an erection. Being a grower it was hanging and smallish, it grew and went up. It bobbed from the hard pressure; being aroused being naked in front of her and knowing how good things were going to be. And I found her attractive and desirable. Then after a couple of minutes or more it went down and shrunk, then it got hard.

Each time I got an erection I liked how it felt, each time she giggled and pointed at it, I told her it was because I liked her and I always enjoyed what we did together.

When she was done with the kitchen she asked “Ready?” That was all it took to get hard again as she stood there to watch it grow and rise again.
She stripped and got on her knees to suck on it a little while as I watched her brunette head move back and forth, she was awesome giving oral. Then she got a condom ready. Knowing I love being touched she held my penis to put the condom in place, then she held the head in her mouth to unroll the rest of the condom.

Then she went on her back and I didn’t need lube or foreplay, she was real wet already.
Later she admitted she got wet and tingly watching my erections grow a few times.

I was horny and turned on as hell, sensitive and close to ejaculation but I was able to control myself and last the entire time with her, between her legs. She orgasmed a few times and only then I let myself finish.

Far from being embarrassed that time, happy to give that woman a very visual compliment

 

My husband and I have been caught having sex before so there's that! And once I remember in high school at one of my best friends' house I jumped into my friend's pool and my bathing suit top was totally shifted and showing one of my boobs when I resurfaced and I didn't realize it.. my friend's parents both saw my boobs lol but I guess they were pretty close to family haha

 

When boy cousin caught me in the BUFF!

 

Friend's mum ran art class in the high school hall once a week. It wasn't linked to the school she just hired the facility for a fee. Me and my friend would usually stay after school the night it was on and help set things up; she'd usually have a table of snacks and one of those big coffee urn things that she took from school kitchen as one of the dinner ladies at the school came to the class and had the key to the kitchen.

One evening me and my friend (her son) were setting everything up and she came rushing in in a panic to say the model had just cancelled last minute. I suggested I do it. Now I had no idea when I said it what I was volunteering for, but she presumably assumed I did. But I didn't. I just thought I'd be posing for normal drawing.

About half hour later the first of the ladies arrived and she gave me a robe and told me to go and "get changed" i didn't know what she meant. I stripped down to undies, put robe on and came out seeking her to find out where the costume she wanted me to get changed into was. She laughed and told me to get up on the stage where the teachers stood during assemblies. She laughed and I went up.

"When you're ready", she said reassuringly. I didn't know what she meant then she motioned silently to take robe off. Which I did and felt an idiot. Then she motioned to pull down boxers. THEN it dawned on me. I had no choice I was there and agreed. There were about a dozen women, including the dinner lady at the school who must have known my age, just looking at my naked body. I must have turned every shade of red imaginable.

 

I was home with my girlfriend and we got horny so we proceeded to get jiggy with it. She finished in cowgirl position but yelling that she had a cramp. We happened to be on the living room couch. And her with her cramp I decided to pick her up and carry her to my room when all of the sudden my cousin walked in. She's about 12 years older than I. Just a little bit embarrassing for both of us.

 

Me and ex wife were staying with friends. That night we got high with weed and some coke.
Her girlfriend had a fight with her boyfriend and he left. We went to bed and fucked twice . About 1 am I could not sleep due to the coke. I got up to get a drink and was bake .I went down stairs not realizing her girlfriend would be awake . As I pour a drink I felt someone come up behind me. It was her girlfriend. She kissed me and dropped to the floor and started to suck my cock. As I had cum twice already my cock would only get half hard. I told her to stop but she stood up and said she wanted to get fucked. I fingered her for a few minutes and went back to bed. I never told my wife and a few months I explained to her girlfriend what happened

 

I lost my virginity with my best friend (2 girls) at a sleepover. We would arrange sleepovers at each other's houses going forward and so gave us the chance to play more and explore. One night I was at her house and we were getting each other off. Someone knocked on her bedroom door. It was her dad. He opened the door but didn't look into the room. He said,"I have no problem with you two shagging, but keep the noise down, I've got work in the morning." I could have died, lol.

 

I was at home. Wife (first wife) wasn't supposed to be home for hours. I didn't hear her walk in the door. She walked into the office and I was naked and jacking off to gay porn. She laughed at me. I was halfway done. Then she asked if I was bi. I told her I hadn't tried it but found the actual blowjob parts and penetration hot.

 

Yeah, I had a moment that was rather disturbing for my ex-wife to have witnessed. I was around 28-30 years old when I became curious about sucking another mans cock. I was watching blow job porn and jerking off almost daily as she was deep into her second pregnancy and not really eager or wanting to have sex. My curiosity drove me to purchase a 10" rubber cock to practice sucking on. Sucking on this thing turned me on as I found myself with a growing erection every time I'd suck on it. One afternoon after a nice shower I dug that cock out from it's hiding place and got on all fours and began sucking on it as I played with my balls. I quickly got hard and started stroking myself and rolled onto my back as though in a 69 sucking moment with that cock when she walked into the room. Well, talk about a mood breaker...she blurts out "WTF are you doing, you're sucking on a cock?" She immediately left the room in obvious disgust. Already being caught I proceeded to finish what I stated anyway. The next several weeks brought on some very uncomfortable conversations.

 

That's sad when people can't be more understanding, but I guess in retrospect you should have had that conversation before tying the knot.

 

.

 

As a youngster (15 or so), I once masturbated in a forest/bushes below a rock wall. After a while I noticed, that I had been watched silently by some other yougsters 10m above me. Only then I realized that the rock wall had hooks in it and was used for climbing / bouldering. And even worse, I had the impression that there was one other boy among them who knows me. I stopped and went away.
In the following weeks, I successfully supressed that embarrassing memory and told myself, that it surely wasn't the other person I thought I recognized. Then I forgot about it.
Unfortunately, months later, I learned, that the person that I thought I recognized indeed is a climber/boulderer.
Now I was certain that it was him who watched me. And in the mean time we both even joined the same school class.
Ouch