Oh, so many!
My ex-wife and I were staying with her best friend. We were going to sleep on the pull-out sofa, and her friend was helping us put sheets on the mattress. I was sitting on the floor because I bumped my knee, and her friend bent over and I got a perfect up-blouse in her pjs, no bra. I probably stayed up spanking it 5 times that night and got no sleep.
The very first time I saw my wife's sister braless...we were staying at a hotel, separate rooms. Her sister wasn't answering the phone, so we walked down to her hotel room. Her sister answered in pjs. No bra. She had her arms over her boobs, but eventually she removed her arms to move her hair out of her face. I will never forget it. Her very thin and clingy pjs. Her tiny but saggy-ish boobs jiggled with the slightest motion, nipples point out almost sideways and a bit upwards, very long nips. Even though she had gray pjs on, she was basically topless in terms of details. She saw me staring but didn't seem to care too much. I saw into her swimsuit quite a bit, too, but never enough to see anything, but so very close. I spent a lot of extra time in the bathroom on that trip.
First time seeing into my wife's sister's bra. (This was after the hotel trip above.) Her sister came over to our house and set her purse down. I got a perfect view into her bra that was at least two cup sizes too big. Perfect dark very very long nipples. I immediately went into the bathroom to explode everything.
I was once in a hotel shower, walked out and my wife's mom was waiting for us in our room. I noticed her staring at me naked. I went back into the bathroom and shut the door and exploded.
During college, I went to a nearby town to see a good friend who was there with his family on vacation. He, his sister, and I went swimming and then back to their hotel room to change. My friend and I changed in the room and his sister went into the bathroom but kept opening the door to peek at us. My friend hid from her but I let her look. I then saw her take her bikini top off but only saw sideboob through the cracked bathroom door when my friend asked me why I was looking at her. (She had JUST turned 18 like literally a day before.) I took my time changing so that she could see me again. Once she came out of the bathroom, she said next time we don't have to change separately and my friend groaned. I went into the bathroom and took some time for myself. (My friend later did, too, but he wouldn't admit it, even though I could hear him! His sister wasn't there at that point, though.)
I will post more as I remember them!
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