I think I've overcome a sticking point recently: getting the conversation to go in a sexual direction. On the last few dates I've gone on, I've managed to steer the conversation that way in a very comfortable manner and it's lead to MUCH easier escalation.

I think part of what was holding me back before was my own mentality of being judged for being some kind of sexual deviant. That, and not knowing what I wanted sexually out of another partner. It took me a bit to realize that not only is it okay to be a person that desires a lot of good sex, but that I don't want to be with a partner that also doesn't love sex as much as I do.

So how does that transfer into dating?

I try to make a point of making the girl realize that I'm a non-judgemental individual. Part of this includes making myself vulnerable. If I'm asked something like "are you a player?" I'll almost definitely own up to it. One of my most recent makeouts was right after telling a girl that I'm in "total manwhore mode in life". Because I was honest with myself in my intent, and honest with her, she was okay to be honest with me. We then had a long conversation about how ridiculous it is for someone to judge someone for liking to hook up with other people, and she opened up to me about her being a really horny person in general, which made it really easy to transition into a kiss.

As awkward as you feel about a sexual conversation is how awkward it will be. This also means that if you're totally easygoing talking about sex, and it's not a big deal to talk about it, she'll feel that way as well. So if any innuendo pops up, jump on that shit. If you see something provocative while you're talking to her, bring it up and discuss! But don't feel weird that you're discussing, because this is NORMAL FOR YOU. I think this falls into the RSD concept of "Law Of State Transference".

On another date I was on earlier this week with someone else, we found ourselves in a book store, where I got her to come look at the sexuality section. We then pulled out random books and talked/joked about the different positions that were in the diagrams. She initially was a bit weird about it, but because I held a casual frame, she became very relaxed about it and then a long sexual discussion began where she opened up about a lot of things like wanting threeesomes, sex on M, etc. Any time she'd say something that lined up with my sexual desires, I'd give her a high five or something similar to give it a casual demeanour. Like "Yes! I LOVE girls that like aggressive sex! Awesome! (high five)"

So the main points here:

  • Be non-judgemental (doesn't mean you can't tease)

  • Make yourself vulnerable

  • BE CASUAL ABOUT IT

  • don't shy away from a chance to bring it up

  • Don't let yourself become awkward, there's no reason to

  • create opportunity for sexual remarks, which lead to longer conversations

Please ask me any other questions about this and I'll do my best to try and give some pointers. Equally, feel free to critique this if you feel I'm wrong on some of these points.