There’s a few different occasions with different people that stick out in my memory.
Involving someone seeing me-
When I was a senior in high school there was a night the ac wasn’t working and I got super hot, kicked off my clothes and the blanket. The bedroom door was shut, but I had slept through my alarm because I had such a hard time sleeping that night. I was basically comatose. My mom came in to wake me up and saw I was nude, with a raging morning wood. She called from the doorway apparently but it wasn’t waking me so she ended up having to come in and actually shake me awake. At the time it was super embarrassing, she made a joke of it later to my dad and he made some joke about my dick being small (as guys will sometimes do with other guys) and my mom just replied with a “oh no, it’s not small at all. It’s huge”. That comment is really what made it stay in my mind. Since then there’s been a few occasional “oops” moments but legitimately fleeting and quick.
Another time was when I used to get up very early to go to the gym before my wife or kids woke up, I’d be home by 5:30 am and strip in the laundry room downstairs before walking upstairs and getting in the shower, which was in the main hallway between bedrooms. My mother in law was staying with us for a bit at the time and she had gotten up to use the toilet at the same time I was getting home. My mil sleeps nude and usually wears a robe in the morning, but she figured everyone was still asleep because it was so early and I hadn’t been to the gym since she had come to stay that time. She opened the bathroom door fully nude and I was about to walk into the bathroom fully nude. We both froze and stared at each other for a minute, smiled, and had a chuckle. She walked back to her room and I got in the shower.
Another time me and my wife had a party and during the party she was flirting with a couple we were friends with. They were going to come back after the party to have a threeway with her while I watched but had to drop another friend they came with off home first. My wife and I were getting started with each other and the doorbell rang, she told me to go get it- assuming it was the couple. It was one of her best friends who forgot her phone in our kitchen. She pushed her way through the door to grab her phone not realizing I was naked. When she turned to leave she saw me trying to hide myself and my boner behind the door, went red and said “oh my god I’m so sorry! Have fun you guys!” And ran out the door.
The last with me was my ex girlfriend who was an exhibitionist. My friend was coming by my college dorm room and my ex was blowing me while topless. He walked in, pretended to be super chill and had a conversation with me while my girlfriend sucked me off. When I came she made a bit of a show of it, spitting the cum out on my dick before licking it back up and giving it some kisses. Then she turned and started putting her shirt on while talking to my friend. It was insanely hot.
With others I had accidentally walked in on that same friend having sex in my apartment common room with his girlfriend at the time. I was getting a water and had to walk through the room; they just carried on.
Another time my cousin was asking about my photography and I said I had just done some new photoshoots. I forgot there were a few topless ones of my wife in there too- needless to say I realized it when his expression changed.
One of my female friends was showing me photos of her vacation and said I could flip through them, she forgot she had a few videos and photos of her naked and fingering herself in there at the hotel too.
Another female friend accidentally sent me a video of her masturbating and squirting that was supposed to go to her fiance who had the same name as me.
The last was when the husband of my wife’s maid of honor made a google album of his wife flashing in public and a video of them fucking. He accidentally shared it to me and my wife, along with several others. Though I don’t know how accidental it was. When his wife had been over to stay on her own her tits are usually falling out of her top.
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