I have a few. The weirdest one was when I was in the gym and this guy was working out with his girlfriend. They were both public school teachers and I'd talked to both of them a few times. One time, the guy was spotting his girlfriend and he signaled for me to come over. I didn't know why until I got there and every time she raised the weights, her shirt fell away from her breasts and I could see right down to her nipples. I know I had this look like "????" on my face, but he gave me an encouraging look in response.
Another time, I was in a store and I was checking out. The girl behind the counter was wearing a low-cut V-neck top. No matter how she moved, I could see her bra. When she started scanning my items, her arms moving back and forth made her boobs bounce and jiggle until finally, a nipple was visible. I know I had a look of shock and surprise on my face, but when I realized she'd caught me looking, she just smiled at me, making me think it was on purpose.
Another one was the earliest I can remember having this happen to me. I was in the sixth grade and was visiting a friend of mine. He had an older sister who was in high-school or maybe older. I'm not sure how old she was. She stood there in the living room in a pair of shorts and a T-shirt. She complained about having something in her eye and lifted the bottom of her shirt to her eye. When she did, she lifted it enough that all of one breast was visible. I know my jaw must have dropped. When she wondered what I was looking at, she dropped her shirt and said, "Oh!" and just giggled.
When I was in high-school, I used to go drink with this older friend of mine at his sister's house. We were playing cards one night and I kept staring at her breasts so much that my friend even pointed it out to her. She laughed and didn't mind at all. She even went so far as to exaggerate every time she had to bend over and at some point, went in her bedroom and took her bra off. She was so amused by it that by the end of the night, she was rubbing her tits together and laughing at the reaction she got from me. After that, she was always happy when I visited.
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