The best braless situation is horseback riding without a bra. Working backwards, my wife just did it the other day. She did it to be flirty and get me turned on. I was going out to ride fences and she told me at breakfast to saddle up her horse and she would go with me. She was wearing a pearl snap western shirt and a vest over it so I did not notice at first. It warmed up a bit and she put the vest in her saddle bags and started riding past me and then I noticed. She let several snaps loose to give me even more of a show. It was hard to focus on fences. Her boobs are 34DD/36D and a bit saggy after breastfeeding 4 kids. They were magnificently bouncing around. We went to pound town that night and I finished with a titty-fuck.
She has not ridden topless since before kids when she had gravity defying 34B/32A boobs. Those were some amazing times.
Moving back in time was my best friend's older sister who was my first fuck. She would tease riding braless or at times topless when we were alone. She was fantastic. Even now at 45 she looks 30. I would love to see her naked again for old times sake. I have not seen her undressed in around 18 years. I remember one time the summer she took my V card, she took off her shirt while we were out riding and was wearing a white ribbed wife beater type tank top with no bra. She dumped water from her canteen on the front of her shirt making it largely transparent as she rode next to me. This was IIRC about two weeks before we fucked for the first time. The flirting was getting heavy and I probably could have made a move on her by then but I was a virgin with no confidence but she was driving me bat shit crazy. At that point in my life I still had not really gotten a good look at a nude woman. Just some family peeks and adolescents cousins and such.
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