My wife's first time topless was without me. She was actually on a cruise with her (then) BFF, and they docked in St Martin. And her BFF dared her to walk the beach with her - topless. When the BFF popped her top off and let her puppies swing, my wife felt obligated to rise to the challenge. And popped off her top as well. But it was closer to "streaking" than actually hanging out with tits out.
My wife would later tell me it was "weird; but also exciting", as other cruisers had seen them and congratulated them on going topless (lol!). I wish I'd been there - not for my wife - but because her BFF had fantastic tits.
The second time my wife went topless was with me. Also in St Martin. She really liked the island and decided to return with me. Ironically, that time was an accident. We were swimming at Happy Bay, the current was very strong; and when she surfaced from the swim, her bathing suit top was over her tits. She tried to detangled it; but it was so rolled up and tangled that she had no choice but to remove it. I told her "Eh...why are you even worrying about it at this point? Your tits have been out and everyone's seen them. And look over there; these other women are topless too." And she just shrugged her shoulders, pulled her tangled top over her head and tossed it to the side. She did stay topless; but it was more like an "Oh well...fuck it then..." It made me happy though.
The third time my wife went topless was her first time at a nudist resort. It was a very different experience for her. She started out wearing a cover-up; and within minutes of settling down at a picnic table, she looked around her and turned to me, whispering: "Should I go topless?" I was like: "Why even ask? It's all good; do what you feel!" And she immediately lowered her cover-up and let her tits out. This time, she was clearly enjoying it. She walked around topless, chatting with people, looking proud of the fact that her tits were out. I think the difference in attitude was due to the fact that everyone around was nude and friendly; so she felt more at ease about letting the puppies out.
Shortly after the enjoyment of hanging out and socializing with her tits out would prove a "gateway" to going "full naked" and socializing in the pool area; but that's another topic.