Sort of.
Many years ago, I had a friend/co-worker who knew I was a nudist. At the time I was just beginning to explore it and I would tell her about being naked with other people. She seemed to be genuinely intrigued by my stories.
She invited me to come swim in her pool; and one day I took her up on her offer. She was wearing a one-piece bathing suit with thin straps. She did propose that I skinny-dip since I was into nudism; but without my wife or her husband there, it seemed inappropriate. So I put on a pair of shorts.
We were swimming around, just chatting, when she lowered her bathing suit straps. She said she just wanted to make sure she didn't have "shoulder tan lines." It seemed like a reasonable idea. Then she started bouncing around a bit, in and out of the water. And suddenly her boobs popped out. "Ooops!" She feigned embarrassment, readjusted her top; only for her boobs to pop out again moments later. Feigned embarrassment again.
It must have happened 3-4 times before I realized something was "going on" there. So I just told her to feel free to just go topless if she felt like it. So she hesitantly lowered her bathing suit top, swam around topless for a few minutes, then told me it felt a little "weird"; so she pulled her top back up. Moments later her boobs popped out again. "Oops!"
I'm still not sure what that was all about. I knew she liked the idea of nudity in front of other people from the way she reacted when I told her about my nudist experiences. So I think her "accidental" boobs slips were definitely planned. I think she was opening the door for me to propose we both got naked in her pool. But when she finally went topless and I didn't say: "How about we just swim naked?", she felt self-conscious and chickened out. But she still wanted to leave that door open.
Unfortunately I moved shortly after so we never got another shot.
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