Before I was married, I used to spend a lot of time at my friend's house with him and his wife. We would stay up late enough that the wife would invite me to just stay the night since I lived an hour away. This was almost every weekend for a year.
It started out innocent enough...she would stay in her regular clothes until we all went to bed for the night. Then after a month or so, she would start wearing pajamas around me, with a bra on.
We were watching a TV sitcom and there was a scene where a bunch of female friends were hanging out in their pajamas with bras on. My friend's wife made a comment about how in real life, women don't wear bras under their pj's. Then I said, "I have seen you in pj's almost every weekend and you always have a bra on." She said, "I am only wearing one because I don't want to offend you." I told her she would never offend me and she can wear whatever she wants, even when I am there.
The next morning, she was walking around the kitchen before breakfast in the same pajamas without her bra. It was extremely obvious. You could see the texture of areola and everything. I said, "you seem way more comfortable without that bra on" and she said she couldn't believe it took her so long to ditch the bra around me.
The next few weekends, she was braless in her pj's right after dinner onward through the night, but her tops kept her covered from showing skin, but you could still make out everything.
Then it started to be the hottest part of winter, and her pajama tops turned into tank tops, and then really, really loose tank tops, while braless.
Then it happened. One evening, she bent over to pick up the cat and I saw both her nipples at once. And again, and again. Then for the rest of the summer I saw her nipples every time I stayed over. Super dark nipples for her light skin, really tiny areolas, but the nipples stuck out a lot, and her tiny breasts really filled out a ton while bending over. I saw them 20, 30, 40 times each night, every weekend, all summer long.
I assumed she was quite aware of it but just didn't care, and I was so flattered. A few years later I brought it up when I was staying over there again while my now-wife was out of town. She was wearing a bra. I asked her why she wasn't braless in her pajamas. She said she had a friend (female) stay over recently and she made a comment how her nipples were visible, so she doesn't go braless around friends anymore.
I told her, stupidly, "Oh, I saw your nips every weekend that one summer and I was sure you knew it but didn't care." The look on her face was pure fear. I tried to convince her that it was no big deal, but to her it was.
To this day, I still can't believe she didn't know that she was flashing her nipples all night long, every weekend for an entire summer. But, maybe she really is that clueless/careless. (Her husband doesn't notice her anyway, so it doesn't shock me that he wouldn't say anything to her about it.)
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