[crazyloco]

...and I wish I had leaned into it earlier.

When my wife and I went on a honeymoon to the Caribbean, we wound up at a hotel with lots of women from Europe. It was the late 90s, and toplessness was still fairly common. I am embarrassed to say that, despite being on my honeymoon, I was loving it a little too much.

After a few days, my wife had had enough. As we were walking down the beach (and my eyes were no doubt elsewhere), she finally said, "Well, apparently, a woman has to be topless to get your attention these days!" and whipped off her top. Mind you, she was extremely conservative, having been raised in the Bible Belt. She would shop at "old lady stores" for her clothes and swimsuits. But now there she was (mid 20s, very petite former cheerleader with perky little A cup tits) walking down a beach topless.

It was so out of character, I was completely caught off guard. And, before I could respond, I could see this single guy walking toward us. I didn't want to cause a scene, so I said nothing, and just held her hand as the guy walked past, clearly looking at my wife's tits.

As soon as he passed, I told her to put her top back on because I, too, had been raised in the Bible Belt. After some back and forth, she begrudgingly did so....but not before I realized I had a massive erection (that was equally obvious to her and the rest of the beach). Clearly, I had enjoyed what had just happened, but I was too (brainwashed?) to enjoy it.

That was a shame. In retrospect, I really wish I had told her how good she looked, how hot it made me, etc. And I wish I would have encouraged it more on that trip and thereafter. Instead, she reverted to her conservative self, and it took over a decade of persuasion to get her to loosen up again.

Thankfully she has, thanks in no small part to a boob job which has increased her confidence. She now regularly wears thongs to the beach and is willing to show her D cups at the right pools and beaches. Sometimes, she even drops the bottoms. The difference is I now provide the encouragement I should have decades ago.

She was particularly bold at Moorea this summer, but perhaps I will leave that story for another post.