don't be shy.... no judgment here
mine would be the first time I bought a vibrator
when my dad found that I bought playboy on pay per view when I a teenager
Mine's kind of hard to explain, but I'll do my best. Two ropes suspended about 8 feet one above another crossing a creek. The task it so commando crawl from the top one half way across, then switch to the bottom one and commando crawl the rest of the way. I got halfway and was too short to actually make the switch safely so I'm told not to. I continue across the top, then my hand slips and I get crotch-ed on the bottom rope. Roughly 20 people saw me get crotch-ed and proceeded to laugh.
Other than that, doing a flip off a high dive but over turning into a belly flop (so a 450 splash from 20 feet up). My gut looked like a lobster, roughly 60 people saw and proceeded to laugh.
And I've only begun fucking with you people.
At the end of the day, it's all math.
Getting caught blowing a guy in the movie theater, a family walked in on us
Getting caught having sex in a parking lot in broad daylight
This happened when I was married. I had called home to see what my wife wanted to do for dinner. She didn't feel like cooking and neither did I. We placed an order with our favorite mexican restaurant in town so I went to pick up the order. We had to order for 4 of us including our children. I had quite a bit of stuff to carry into the house and proceeded to grab everything. As I was walking to the stairs my shorts I was wearing fell down around my ankles. Luckily for me I was wearing underwear. I couldn't pull them up because my hands were full. I glanced out towards the street (at the time we lived on one of the busiest streets in town) and some woman in the passenger seat of a car pointed and started to laugh. I climbed the two steps the best I could with my hands full and my shorts around my ankles and made my way to the door. I was able to ring the door bell and my daughter answered the door. She looked at me and said, "Hey Dad your shorts are around your ankles.", I told her to just open up the damn door and she was laughing hysterically as well as my wife when she walked into the living room. I said, "A little help would be nice" then proceeded to laugh about the whole thing.
when my husband and I had sex, she was on top and our 14 year old daughter came to spending money and permission to go to the disco. I told her to take money out of my wallet and not return sooner than in 23 hours
About 15 years ago, I was 56 and my wife 61, and we were in a 69 position with her on top and facing the door. We'd been at it for 20 minutes or so and really into it when I glanced around her and there stood our 25 year old son and his 22 year old girlfriend. They didn't see me noticing them and I just kept thrusting into her mouth. I didn't know what else to do. My wife never noticed and they just stepped back and softly closed the door.
I never told my wife and they broke up a few months later. She wound up homeless with a baby (not our sons) and we informally adopted her. She and my wife were very good friends before she and our son broke up. Now she is one of our best kids, loves us dearly and has 2 kids. Our son married and has 2 kids also and we've never mentioned it.
I wonder every now and then if they ever remember it and what they think. I don't think I'll ever ask but I'm writing my life (my kids asked me to) and that's one of the things I will put in it. I'll also let them have all the stories I write (I think that right now anyway) because we've always been close with them and most of them will be true and about my wife and I.
My worst moment at the time was probably when my mother caught me sucking her boy friend off. I was only a teen then. That resulted in me being sent to boarding school. Its a long story but it ended well for me.
In highschool during gym class my shorts fell off. And I had no panties on either.
we were making out at the back of the school building for hours and we got locked in campus. the guard was gone, so I scaled the 10 ft gate in about five seconds, but my gf that time (who was heavier than me) was scared of heights so when she got on top she never wanted to go down. so I played catcher and got squashed under her. the guard came back because of the racket we made and asked what the hell we were doing. needless to say I was sporting a sprain in six different places the following morning.
my youngest finding my vibo and running through with it, wobbling in her hand. pure shock horror, thankfully I didn't have any guest in the house
Before I had a car, I was getting on the public bus and fell going up the steps, then slid down and out onto the pavement. This guy helped me but he was laughing so hard, I thought he was going to fall too.
LOL I was having sex with a GF when her younger sister who lived with her came strolling through on her way to the bathroom. The silly part was the GF expected me to roll off. I just reached back and drew the blanket over us and told the GF she'd have seen a LOT more if I HAD rolled off!
Getting mocked many a time ... couldn't point out a few :P
My most embarrassing Sexual moment was probably when I was a teen and I got caught giving my BF a blow job by his grandmother and grandfather. From his grandmother's reaction you would have thought we were committing murder.
But this is nothing in comparison to my MOST embarrassing moment ever.
When I was a teen I was in church with my family. During the mass, this woman of about 250lbs put the kneeler down on my toe and kneeled on it. I instinctively yelled out "OH FUCK!". After realizing what I just did, I made it worse by saying "OH SHIT, SORRY!!" The church went silent and everyone was staring at me. My mom was beet red. The priest's eyes were like daggers shooting right through me. It was as I could feel the flames of hell nipping at my ass! LOL.
Well needless to say there was hell to pay for that "incident".
Another one i had forgotten.
My bf at the time were going at it in the kitchen when his mother walked in on us - we didnt realise she was at home.
He had just started to cum and he couldnt stop and gave her the perfect sound and vision of a guy cumming in his girlfreind.
She watched till the end - said nothing - and walked out.
The two of us were shell shocked and didnt know what to do or say.
The following day he told me she had talked to him that night and told him if he wants to do "that" to use his bedroom. Then asked if I was protected.
The next time I saw her a few days later I appologised, and she and I sat down and had a talk about sex, me, and contraception. She was wonderful to me. We were very good friends after that - even after my bf and I broke up a month or so later.
Getting off the bus in Pgh. PA heading to work! I noticed that a few guys were wolf whistling and making rude comments! Then I looked down and saw the used condom dangling from my high heel that I had been dragging for three blocks! Yuck!!!!!