I dated an extremely conservative girl for a month. She was 27 and not only a virgin, but no one had ever seen her breasts before, either.
One evening, we were cuddling and she said "rip my shift off, I want to be daring once in my life, so rip it off." So, I took it off. Then I took her bra off...she didn't have areolas!! She only had nipples and they were--no joking--almost 2 inches long and weren't stiff. It was unusual, but I didn't react or anything. The no areolas was hard to get used to, though.
So, for the month we dated, she was basically topless all the time. She loved it. That was as far as we got, though.
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