So let me set the stage. I’m at a local bar, with a table full of 2 friends and 3 women we’ve been chatting up. At one point after a particularly aggressive statement, one of the women, clearly interested, plants her calf-high heels on the chair, right at my crotch level. “You, little man, need a lesson.” So, I lift her leg, and while keeping eye contact, I slowly run my hands up the leather to the zipper and unzip it. Maintaining eye contact, I unzip the boot and pull it off her leg. As SOON as the boot is off, I drop her foot, grin, throw the boot over my shoulder say, “This is mine now,” and walk to the bar to get another drink. The look on her face was PRICELESS! What started as intrigue and tingles flipped completely to jaw-dropping surprise and outrage.

I get back, and of course, she DEMANDS her boot back. After all, it’s a 2.5 inch heel and she’ll look goofy hobbling around like that. I look at her, grin and say, “Well, what are you going to do to earn it back?” She looks at me and says, “What do you want me to do…?”

Aaaaaaand that's where I freeze up. I hadn’t expected to get even this far, let alone had an answer prepared for this possibility. I stuttered for a bit and mumbled something about her buying me a drink. Complete loss of frame and breaking the mood. Guess who went home alone that night? (hint: it wasn’t my friends).

Anybody got any tips on where/how to proceed once you get to that point? What are good demands to keep the escalation going?