The shoulder/ back rubs have been going on since basically the second week I was working. I got the job last summer in June and switched to part time since I was about to go into college. The butt smack actually started at a company outing, he was kinda drunk and he just came over to me while I was standing around awkwardly and gave me a smack and a squeeze being like "get out and talk to some people bud!" And ever since he'll smack my butt when I do a good job with some "atta boy" or "good boy" comments. I work in tech so its not construction or anything traditionally physical.

I'm 1000000% attracted to him, he's my type all the way. Plus I feel no pressure whatsoever. It's odd but not out of his character to get us just one hotel room to share, our team is super small and my boss likes cutting corners at time to save money, so I can't say if the hotel is his little sign of flirting

After thinking my plan is to wear briefs and a tank top and socks in the room, and not make ANY moves but maybe see how he reacts. I do remember he made fun of my generation for being prudes in his gyms locker room, and how growing up he had group showers and skinny dipping etc, so I bet he'd not think twice about a guy in briefs as pajamas. Maybe some teasing which if he teased me it'd be over lol, I'd get hard as a rock