Please help me to escalate

[Winston]

I have a problem, I don't know how to escalate.
I'd appreciate if you could give me some ideas of new behaviors or some new way to think about this kind of situations, because I keep banging my head against the same wall again and again.

I am going to relate a situation which I think is really telling of my problem:
I was at a kind of business conference (I wasn't working, I was just interested in the subject). The conference took place in the conference center of a 5-stars hotel. The conference spread over several days, therefore I took a room in this hotel.

The situation happened during the cocktail at the end of the second day. I was talking with a cool guy, very "game aware" (I discovered aftewards he was a former wing of someone very famous in the game community). This guy went to open a girl, meanwhile I was checking my phone and when I raise my head a cute girl was standing in front of me and started to talk to me, basically opening me. We chatted a bit and after a few minutes she proposed that we go sit somewhere, basically isolating me.

So we went sitting somewhere a bit away from the people and we kept talking.
Until that point I think I did a good job with the conversation: playful ways to answer her questions, challenging her about her answers, straightforward eyes contact. I think there was a flirty vibe (but obviously with plausible deniability that this was only a normal social conversation business-related).

So the situation was flirty with an absolutely perfect logistic: I had a luxurious hotel room upstairs, it would have taken us literally 3 minutes to go from the conference center to my room.

What should I have done from there?
What I did: lame conversation losing the initial flirty vibe that became more and more rational. 5 minutes later my new friend came rescue me by bringing the 3 of us into another group.
Basically I think I was scared of escalating/I had no idea how to do it, so I fall back to rational thinking/conversation as a default and safe alternative. And this happens to me a lot: good start, with a lot of initial interest from the girl, and with good inputs to the interaction from me, but I am losing it all because I don't know how to escalate properly (I think it's part ignorance, part fear).

 

[Don Giovanni]

Make a point for yourself to touch her early, incidental and platonic type - her forearm when making a point, bumping into her while walking, then raise it to sexual touch later. Its natural to kiss someone for example when you’re holding their chin and brushing their hair away.

Establish a sexual frame and non judgemental frame. This will help you escalate, it will make sense. Its easy to do this with sex talk gambits.

Smooth escalation is a skill in its own. But in the end you just have to make the move. If the girl likes you, it doesn’t need to be perfect. It can be downright awkward and still successful sometimes.

 

[Winston]

Make a point for yourself to touch her early, incidental and platonic type - her forearm when making a point, bumping into her while walking, then raise it to sexual touch later. Its natural to kiss someone for example when you’re holding their chin and brushing their hair away.

Establish a sexual frame and non judgemental frame. This will help you escalate, it will make sense. Its easy to do this with sex talk gambits.

Smooth escalation is a skill in its own. But in the end you just have to make the move. If the girl likes you, it doesn’t need to be perfect. It can be downright awkward and still successful sometimes.

This was useful feedback.

I end up banging a new woman, after having implemented a more agressive way of escalating, especially touch and sex talk.

I have meet this new woman through social circle and I noticed the conversation was flirty, but as always, there was ambiguity/plausible deniability.

Then before our friends group splitted, she showed me pictures on her phone and I watched the picture by putting myself behing her, a good part of my body pressing against her body. And after that, she automatically proposed me to hang out another day.
It was like she needed that unambigously body contact to be sure I was interested in her, which allows her to move the seduction forward.

And at our second encounter I escalated very agressively right from the start (I had found an excuse to meet at her place), but it was too fast for her. So we hang out outside for several hours, during this time I kept making body contacts, and at some point we talk about sex a lot, which made it really easy to go back again at her place and slept with her.

I am happy because it sounds like I have understood some important part of the seduction process while gathering a reference experience showing my brain how powerful are touch and sex talk.