Most embarrassing moment

[LeeKee]

Husband and I attended a swinger house party. I was in one of the play rooms in a 3some, 2 guys when someone came in. I looked up and it was my sister, her husband and another couple. Nothing I could do and the guy behind me wasn't stopping. No, we did not play together even though her husband was trying to get us to.

Thats hot!

 

[Bigboobbabe]

Husband and I attended a swinger house party. I was in one of the play rooms in a 3some, 2 guys when someone came in. I looked up and it was my sister, her husband and another couple. Nothing I could do and the guy behind me wasn't stopping. No, we did not play together even though her husband was trying to get us to.

I remember hearing we're reading someone say don't be embarrassed about who you run into because they are there for the same reason.
And on the same note, you don't usually have to worry about them spreading any information about you because there is only one way for them to know what you did in that room.

I haven't had the opportunity to use that philosophy, but I do hold it close.

 

[Bigboobbabe]

I was a virgin on our wedding night, and my wife was quite experienced. I only lasted about 30 seconds the first time we had sex. I got a lot better as the night progressed, but that first time was embarrassing.

That was a lot of anticipation causing that.

When I have a partner do that, I comfort them by thanking them for the compliment. Clearly they were so aroused from what we had been doing that they lost control.

I have also said something about now that your first is over we can focus on round two.

 

[N8V1]

Choking on a huge mess of sperm so badly that I wet myself. The guy left me the next day and stole my favourite frying pan and my most expensive corset for his other girlfriend to wear. The following week I got sent photos of her doing it right. It broke my heart.

Have you learned to take a load properly now just curious

 

[PintlerMan]

Only thing that pops into my mind is, while getting my mouth fucked, blowing snot all over my face, he chuckled, handed me a towel and I cleaned up, the we continued.

 

[cdstefi]

Got caught on what I knew was a dead quiet back lane, because it was a dead end up in the Black Mountains.

Woman I was seeing at the time was riding me in the back seat of my car with her skirt up around her waist, knickers pulled aside, and what I hadn't banked on was the local pony club trotting up the lane.

We didn't have time to get out of the back seat but did at least pull her skirt back down to conceal her ass and my cock which was still inside her

 

[Oshkosh60]

Ten years ago i moved to another state. I have worn some women's undergarments occasionally since I was an early teen. I wanted to possibly find someone sho might also share that experience just so I could talk to someone about it because this has been a secret thing my whole life. So fifty miles from where I live now is a gay bar and i thought perhaps there might be a kindred spirit there. I looked around at the guys there and could tell it was probably a wild goose chase (yet again). But I did start casually talking to four young lesbians who were in their late twenties. I eventually explained my situation, in the closet, married, just wanting to find a like minded guy to chat with. Obviously they were not going to be of any help. Then one asked where I lived and i said forty minutes away, but had once lived in the neighboring state. Really ? One girl was from the same state and it turned out the same town. I was shitting bricks because she mentioned where she went to high school .... I said I had only lived in that town ( four hours away from the bar) for a few months. In reality, I lived there thirty years and she and one of my daughters had to be in the same class at the same small school. I booked out of there fast before she recognized me.

 

[MaturemanAJ]

One time ,many years ago, when i started going to my wife parents home, i was heading to the kitchen to grab a beer for me and my fil. My ( then) gf was cutting some veggies for dinner and after i saw her great ass inside some stretched yoga pants i couldnt resist to get my hands all over her. I gave it a proper grab and pushed myself against her.
It was her mother, not her.
My face was red for hours and i must have apologized 1M times that evening while the 3 of them made fun of me.

Yes, was totaly worth it

Had kinda the same experience but it wasn't touching. Thought my girlfriends younger sister was sitting downstairs watching TV as I could only see her legs and part of the robe she was wearing.
I called out nice legs baby and her Mother yelled back Thanks stud.
My girlfriend busted out laughing.
Totally embarrassed but her mom always liked me after that.

 

[BabyBoomer50s]

Yeah, so not sure if this has been posted, but what has been one of your most embarrassing moments either sexually or any other moment.

Doing this, I hope people will just have fun with it. No judgement, just let lose!

I've had a few but the one that stands out to me the most .....

I was in middle school and in gym class and I am not sure what was going on withy stomach, but we were all sitting on the floor. ( You do know gyms echo and are loud?) Anyway, I passed a toot and acted as if someone else did it. It was pretty loud and I know I turned fifty shades of red but I am thankful that none of my friends approaches me about it .

Anyway then the other was mistakenly approaching someone for somebody else. Mind you, it was from the backside. When they turned around they asked if they could help me and I was just like "no, I'm just looking around" then found my person lol

These episodes don’t seem all that embarrassing compared to some of the answers so far!

 

[Carolinaguy45]

My boss walked in my office as a coworker was giving me a handjob…so embarrassing and not sure exactly how much he saw but it was obvious

 

[liqueur]

My boss walked in my office as a coworker was giving me a handjob…so embarrassing and not sure exactly how much he saw but it was obvious

Was the coworker male or female? Or other?

 

[Carolinaguy45]

Sexy female I worked closely with on major projects … her skirt was also definitely askew as well

 

[CEOescape]

I was a virgin on our wedding night, and my wife was quite experienced. I only lasted about 30 seconds the first time we had sex. I got a lot better as the night progressed, but that first time was embarrassing.

I too was a virgin with my wife had a active sex life, she was wonderful telling me some of her activities be for getting to our resort , she sucked me off ,,then we showered and went to bed ... she was a great teacher lol

 

[lowcollar]

Having 3 friends walk into my college dorm room while I was jerking off.

 

[gtnlynn]

I too was a virgin with my wife had a active sex life, she was wonderful telling me some of her activities be for getting to our resort , she sucked me off ,,then we showered and went to bed ... she was a great teacher lol

On our wedding night, my wife still claimed to be a virgin, but it quickly became obvious that she was experienced. It was a few years before she finally told me about her premarital sexual activities.

 

[1DarkNightOwl]

I remember hearing we're reading someone say don't be embarrassed about who you run into because they are there for the same reason.
And on the same note, you don't usually have to worry about them spreading any information about you because there is only one way for them to know what you did in that room.

I haven't had the opportunity to use that philosophy, but I do hold it close.

A very true statement. Keep that philosophy to hand.

 

[1DarkNightOwl]

I agreed to meet a woman at her house before I met my wife. I knew she had children and it was going well untill her 21yr daughter entered the living room, seen me and her mum smooching and said 'Mum, your going to be banging tonight?'. That killed it.

Makeout (I beleive the Americans call it) and intimate touch is all that happened. She put me up in the spare room. I was 25yrs.

 

[liqueur]

'Mum, your going to be banging tonight?'. That killed it for me.

That would have just made it that much more exciting for me.

 

[Bigboobbabe]

Another one of mine..

I agreed to meet a woman at her house before I met my wife. I knew she had children and it was going well untill her 21yr daughter entered the living room, seen me and her mum smooching and said 'Mum, your going to be banging tonight?'. That killed it.

Makeout (I beleive the Americans call it) and intimate touch is all that happened. She put me up in the spare room. I was 25yrs.

At least you were older than her daughter.

2 of my intimate friends are younger than my daughter. After tonight, I hope to make that 3. My daughter lives over an hour away so I don't worry about her walking in.

 

[1DarkNightOwl]

2 of my intimate friends are younger than my daughter.

Given my daughter's age that would be legal but not appropriate. Hot as hell and a fantasy of mine but wouldn't happen even if I had the chance.

 

[Bigboobbabe]

Given my daughter's age that would be leigal but not appropriate. Hot as hell and a fantasy of mine but wouldn't happen even if I had the chance.

My daughter is 35. I just turned 60.

 

[1DarkNightOwl]

My daughter is 35. I just turned 60.

At 60 I could possibly have a different viewpoint.

After tonight, I hope to make that 3

Hope this went well and you made it 3.

 

[fullservice65]

Choking on a huge mess of sperm so badly that I wet myself. The guy left me the next day and stole my favourite frying pan and my most expensive corset for his other girlfriend to wear. The following week I got sent photos of her doing it right. It broke my heart.

I know a few people who know a few people who can help that guy see the error of his ways.

 

[JordynRose]

There have been so many very difficult to pick just 1.

 

[Up4fun&69]

Mine was embarrassing, but funny (to me).

I had a FWB after my divorce. We tried dating but all the pieces weren't there. Still, the sex was great, so we continued playing from time-to-time. She was a competing body builder. When in training, her body was amazing. When not in training, she was a personal trainer and home gym consultant. But during those times, her body wasn't as defined and shapely, and her mind strayed into some dark times. It was one of those times she called, said she was really down, and wanted to come over for some sex and cuddling. To brighten her mood, I turned the lights off and lit some candles. We had a beer, talked a little, then started making out. It became hot and heavy, quickly. I was naked and she was down to just her bra holding up some nice C cup breasts. As she was guiding my cock into her, I was unclasping her bra, pulling it away from her chest, and tossing it across the room. We were really in sync and just having hard, animal sex, with her riding me when I noticed the room had gotten darker and there was smoke wafting about. Yup, I had thrown her bra into one of the candles. It was half on fire and half melting, just like the plastic top of the table beneath it. I managed to take a beer and douse the flames. So went the amorous mood for me, especially since I was so embarrassed. But still, I was giggling at the situation. But man was she angry that I had ruined one of her favorite bras. Her rant went on for a good 10 minutes. I got weekly reminders about the bra's make, style and cup size until I replaced it.