If you’ve managed to get the dude in your bed on multiple occasions, good on ya; you’re reaching pro status. But with that comes “feelings” a lot of times, and that scares some people. Don’t catch emotions. Coyly let him know you’re interested, but don’t be desperate about it. Not the sex, not the “something more.” It may evolve into that one day, and you’ll know if the sentiment is reciprocated (if you’re self-aware, at least), but for now, go with the flow, let things happen, be easy-breezy, my friend. You’ll both have more fun that way.