I can totally relate to the OPs story. My wife was wild long before we met, then stopped being wild just before she met me because....I don't know why, actually...probably because she regretted her wild days. Anyway, we were going to her friend's PhD party, and she put on a summer dress she had always wanted to wear. Well, with a bra, it looked trashy because it showed so much of her bra. Without a bra, though, it looked classy, still rather conservative, but really daring for her because while nothing showed when she was standing, if she bend forward even a little bit, you could see most of her breast and often her complete nipple. So, she put her bra back on and so much bra showed that it looked trashy again.
She was frustrated, so I told her to go braless. I remember her "Are you SURE?!" as though she really, really wanted to go braless, but didn't have the guts to bring it up herself. I said, "Ya, you can't tell you are braless unless you really bend over, so just be careful."
We get to the party, which were friends of hers she had known since junior high, none of who had seen any of her skin below her collar bone. We get there, and she bends over to take her shoes off and immediately flashes three or four people her bare breast down her dress. Evening goes on, she bends over a lot more for various reasons (pet the dogs, pick up snacks from the low coffee table, etc), and literally everyone there had a chance to see her bare breasts more than once.
About two hours into the party, she bent over and saw a guy looking down her top, she puts her hand over her chest, turns beat red, pulls me to another part of the house and said, "I think I just flashed him. I have been sooooo careful all night!" Then I said, "Sweetie, you have been flashing everyone since the moment we got here and you took your shoes off." She acted clueless, and I knew her well enough to know she was actually clueless about it. She said she wanted to leave now, but I talked her into staying.
For the next half hour or so, she would then try holding the front of her dress when she would bend over, but finally she whispered to me, "Can I stop holding my dress do you think?" I told her of course that was okay; everyone has been looking all night anyway (at least I had hoped they were all looking).
On the way home, she said she wanted to tell me something, and she said that when she caught the guy looking, it totally sucked at first but then she said she really liked it and later in the evening bent over in front of him again on purpose when I wasn't nearby and watching him look down her top and she said she loved it so much.
That opened her up a bit, and when we had tons of friends stay at our place here and that summer, she felt comfortable wearing thin pj tops braless, bent over a lot without caring, and loved every second of it.
Now she is back to her conservative way, which is okay, I guess, but I hope she loosens up again!
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