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If your talking about relationships then there is no real way to tell...99% of women in a relationship will do w.e crazy shiit you want as long as they are happy, trust you, and see you as an alpha or as the leader....it might take some time with some of them but a glass of wine and some for play goes a long way!
My gf was a bit of a prude when we first started dating but now shes a freak, nothing is off limits with her! it took time but now she loves it!
That is the part I am missing. I think part of the problem is i need to re-frame and get in the mindset there is nothing wrong with the things I desire and also be able to lead and convey, so that is it not awkward. Great link btw! I still have questions about the first sexual encounter and if that is a good time to "establish the norm" so to speak.
There is a girl I have been friends with a really long time but haven't seen her much in years. Last time we hung out we got really drunk and I noticed IOIs but she has a bf and I wasn't too interested in finding out if she would cheat on him. Add to that we had a conversation way before all that where I basically told her I am a freak in bed and she can't handle me. She didn't really say anything either way, but I'm guessing she is like most of the girls I've experienced. Not really down for being a porn star, etc. We're gonna hang out again soon. Last time we hung out I slept on the couch and she made a comment that she didn't know why she didn't just let me sleep with her in her bed. I'm guessing she is ready to see what it's like to be with me, but I don't want to hold back. I want to be myself. I guess every cry for help ends up with a story like this

I can feel it already that I will come across as needy and not as if I have done the things I want to experience. This girl should trust me. I've known her for many years and always been there for her. Is the first sexual encounter the time to push the envelope? Tell her all the naughty things I want to do to her. Like ask her if she likes cum? I don't really know the best way to go about this.