This guy tends to ask me very personal questions, but is that ok now that he has a gf?

We've been best friends for 3 years. We always had a bit of a thing for each other (or that's what others said at least), but we've always been platonic friends. I'm pretty conservative when it comes to certain topics, but he has absolutely nooo boundaries. The closer friends we became, the more open he got. He asks questions about the type of bra i wear, he always wants to know what I'm doing, essentially nothing is off boundaries. The other night, we were talking until 4am on the phone, and he randomly started to talk about , and out of nowhere he sends me a pic of an actor I really like without his shirt on, and goes "its 2am, you don't have a bra on check to see if you're perky now". Of course I yelled at him and told him to behave, but he does stuff like that all the time. Yes, we're best friends, and he feels he can ask me anything, but now that he has a gf sometimes I don't know if that is appropriate. If my bf did that, I would freak out, but I dunno what type of personality his gf has cause maybe she is ok with it. Him and his current gf have been friends for 6 years, and began dating 4 months ago.