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Some of this solves itself over time. I have to agree with the guy about the "Did you cum?" question. It is so hard to broach this subject with women during the act itself unless you are really comfortable with each other. It would be a whole bunch easier if both people would just talk during sex.
As to the confidence issue, it took me years to get the whole relaxed approach down. It partially comes from having a strong marriage and feeling comfortable. The other day, I was in an airport lounge for a couple of hours prior to a flight. There was a young woman reading a book next to me. I asked her what she was reading, and we ended up talking around 3 hours (while waiting and during the flight). She was a stewardess that was returning from vacation, so she gets hit on all the time. I told her I was married right from the beginning so that there would be no pressure and no thoughts on her part that I was in any way doing it. I was flirting of course and so was she (she touched my shoulder several times during the conversation). I walked off that flight feeling very good about myself and just a bit smitten. Of course nothing would happen, but it is moments like this when you connect with other people that really make life nice.
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