“I know he used my hat to jerk off into and returned it to me.”

Male advice?

Hi there,Hoping to get a guy’s perspective on this, as I have definitely never been in this situation. First off, maybe I should mention that I am very sexually liberal and not easily offended. If you are, I probably am not actually seeking your specific advice, thanks.I go regularly out of my way to a specific bar to hear awesome music. They have an amazing residency every Friday and I never miss that. I’ve been going for years. They also occasionally have music during the week and I’ll catch a show here and there. It’s not the only place I go; I try and see live music a few times a week.Anyway one night I went in with a friend on a random night when there was no music. The bar was pretty deserted and we ended up having a really fun time, mainly just us and the hot bartender. I knew him by sight, as I’d been going there regularly even before he started working there a few years ago, but never really talked to him. He was actually really hot and cold with me – sometimes super friendly, others seemed to not acknowledge me. I didn’t really care. We had a blast that night, though, the three of us and I fell for him a little bit. That Friday, he was at the show even though he wasn’t working, and stood thisclose all night, hugging me, asking if I had had a good time the other night, etc. After that whenever I’d see him, we’d joke and give each other shit in a good-natured, flirty way. He’s definitely never ignored me again. One night a few weeks later, in a crowd of people, he asked me if I was into bondage, leaving little question as to who would be the one tied up (I took the fifth). Okay, and since then, I’ve just been smitten. Now it’s been a few months though and nothing much has really happened. He’s working when I see him and I’m pretty shy and get sort of tongue-tied around him, so I don’t think I’m going to be the one to move things forward. Besides, I’m supposed to be the submissive one! And while he says sexual things to me a lot, he never makes a move, asks for my number etc. (I friended him on Facebook a few weeks after that first time I went in as he says “on a nonmusic night”).

Anyway, I stopped in the other night, after getting out of work later than I usually do. I had expected there to be music, and it was the first thing I asked him when he came over, which I think annoyed him. I ended up staying because I had been worked til 10pm without eating so I decided to get food and then just ended up there til 2. I left my hat there that night. The next day, I get a fb message from him saying he had found it and would hold onto it for me until I was in again, and signed it love always. Went in this past Friday, and he gets it for me right away. I take it, and thank him and he asks – what were you afraid of, that I’d jerk off and use your hat as a cum rag? I looked at him, with my mouth hanging open and finally managed to reply, you probably did. To which he said, yeah, I probably did, and walked away. Before I leave, he tells me that there’s music again tomorrow night (this past Saturday) – that he knows I don’t like to come in when there’s no music, but that there’s music tomorrow. So I went in the next night, met a few friends, and hung out til 2. He made a point of mentioning having used my hat as a cum rag again, this time, referring to it as “I told you I (did so)” – which for me nullifies the joke possibility and now I know he used my hat to jerk off into and returned it to me. Now, the thing is, is that I think it’s really really hot. I slept that night with my hat over my face. I’m so turned on by him in general this is near paralyzingly for me. I sent him a 3am message saying I hoped he was kidding – but just because I felt impelled to mention it in some way. Now, I don’t know what to do. While I do find it hot, I still don’t know why he would do that – is he definitely into me? Or he trying to freak me out? Is this just something guys do? I know my reaction of finding it sexy probably isn’t the normal woman’s reaction, so does he want me to instead be turned off? Should I let him know I found it sexy, or play it coy? Should I tell him I was wearing the hat to diddle myself long before he ever got his hands on it? Any advice as to what I should say or do next? I am so out of my element – all I want to have to do is find a magic sexy quote to put up as my status on fb that will make him finally ask me out haha. Obviously that’s passive and silly. I do know that I don’t want to feel like the aggressor though, just going into his work all the time. Or at least anymore than I have been. What else can I do? I’m moving to this neighborhood in March and am worried if I handle this wrong, it will end up ruining my favorite place to see music. And just because his way of flirting is so rooted in sex, does that mean he’s only interested in sex? Or was this his way of marking me so to speak? I don’t ever really see him flirting with other women outside of the friendliness you have to have as a bartender, and the way he looks at me makes me feel like the only woman in the room, sighhhhhhhh. I could see myself having freaky sex with him until we are old and gray.

Thanks for reading this long, convoluted, possibly boring tale. Please help me spice it up. Any advice is greatly appreciated!!