I’m going to attempt to translate this to thinking-with-penis-speak:
The advice Dan Savage always gives to men who say things like, “I asked my wife about a threesome and she said no / said we could do it but I couldn’t have sex with the third / etc.” is that the only possible way that their wives will ever come around on the issue is if they first believe that their husbands will respect their boundaries. Do not bring it up over and over, do not apply pressure, stick to whatever rules are set. You might get the result you want and you might not, but there is no other way.
By analogy, there are many men who would like to see some topless women around when they walk down the street in the summer. That is okay, it is okay to appreciate how other people look. But no one is going to do it if you are making them feel uncomfortable for doing so.
So STOP making stupid jokes about it (there is just no chance your joke is clever enough to be worth making). STOP talking about how great it would be. STOP gawking on the rare occasion it does happen. STOP suggesting that women who do it must have trait X or trait Y (whether those are positive or negative traits). And STOP being a sexist prick in general. When women actually believe that men aren’t creeps there is a chance that more of them will feel comfortable doing this.
This route also has the advantage that if you pull it off, you actually won’t be a creep.
