I'm in the process of starting a new D/s relationship with a male sub that approached me. In the past I was more dominant, but as I've found a more subby side of myself with men who I respect enough to be dominated by (very rare), I've lost touch with some of that Domme side. That said, the switch in me definitely still finds a thrill in the idea of dominating a man.

This new sub in his profile says that he is just starting to explore his subby side, he'd like to be "broken down used and humiliated". He goes onto say he'd like to be used financially for bills and whatnot, but also for cleaning the house/chores/handyman type stuff. The trick for me is that I don't want him in my apartment (I have roommates and rarely bring anyone into my apartment anyways), so the cleaning/chores/handyman stuff is a bit harder to achieve. Some exterior things come to mind like driving me to the airport, driving me other places, maybe buying me groceries, take my car to the mechanic...

When I asked what boundaries he had and what made him tingle he just said "don't have much boundaries except ones that most humans have" which tells me he doesn't really know at all.

So my question is two parts

1 - how do I best guide him through understanding what he likes and doesn't like/suss out his kinks? I'll be sitting down face to face with him soon to have a in person discussion about it all, any questions and guidance for the conversation would be helpful. I plan to probe around what brought the initial curiosity out, what type of media/portrayals he's seen that he feels drawn to, what sort of style he's looking for - psychological or physical. And of course see if I can get a sense of his boundaries. What else am I missing?

2 - What sort of "used and humiliated" activities can I do outside of the home from a Domme to a m sub? What maniacal things have you done/had done/or seen done? I love hearing people's ideas, so many great minds.