Here's where I'm stuck; I can approach just about any women and strike up a conversation with her, the problem is escalating the situation sexually. It's that I feel uncomfortable being sexual with a girl, either kino or talking about the subject. I know where this comes from, it stems from growing up and being told by my parents that sex is something you never talk about. This combined with my own thinking that talking about sex with a girl will make her think you're a pervert (which is rarely the case.)

Is this something I should be talking to a therapist about? Should I try going out with the mindset of, "lets see how sexual I can be with a girl before she slaps me/calls the police"? What are some tips or mindsets you use to escalate a conversation sexually using kino or verbally?