I've had the boundary conversation pretty early in a couple relationships. Generally because they're either joking about boundaries and/or ask about my sexual history (mine includes sexual assault, which colors my opinion of situations like this). Otherwise, I've had most guys err on the side of caution, and I am the one asking if he wants to do X to me that he might have been nervous about asking me about.
Others push boundaries and get a "NOT COOL" response. My last relationship ended because he pushed a boundary AFTER we had gone through the boundary conversation a couple times.
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"Without passion man is a mere latent force and possibility, like the flint which awaits the shock of the iron before it can give forth its spark."
— Henri-Frédéric Amiel
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