It's been a longtime "thing" of mine. Used to go surfing nearly every day with my female best friends in our teens. She'd just up and pull her top away, exposing some monoboob to check her tan and occasionally moon me as she surfed away when she caught a wave before me. After surfing, she would strip down to nothing and get dressed for the rest of the day before we left the beach. Her and I eventually fooled around some with another female friend, but it never led to anything major. It was just good casual fun.
In my first marriage to my highschool sweetheart (lasted 7 years) I had the curiosity, but wouldn't dream of it happening. She was too much of a prude and I was more... possessive? My current wife (31) and I started out slow. She's way more relaxed about her being nude in front of others than I am - I honestly had to ease myself into the idea of her naked in front of other people. But the ultimate deciding factor here was, she wasn't my high school sweetheart. I didn't "plant the flag." There are nudes of her out there among ex-boyfriends. Who gives a shit?
At first, she'd just slide her top down while we were in the water. Then we would just go nude together in a more remote area of the beach and get dressed when we started to see silhouettes approaching. We talked about just stripping in the more crowded part instead of walking two miles just to have some privacy.
The real tip over the edge was a day when we drove all the way to the beach without bathing suits because we planned to just walk to our remote area... but it was closed. There were two other couples around. One was a mature couple and they didn't care about anything other than relaxing and catching rays. The other couple (5-10 years older than us) was busy trying to play it cool while making a feeble attempt to inconspicuously get each other's rocks off. We just kind of looked at each other and made sure we were both cool with it and stripped down. Honestly, best beach trip I've ever had. Neither of us have bought a bathing suit since.
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