I've been with women I had a hard time coming with (though I could always eventually make it happen) and girls where it was easy. With my first girlfriend I would hold off until she was done, which would take awhile, and then she would just stop. That was a pretty terrible relationship.
Anyway, I've come to a few realizations. First, unless I were to let myself orgasm right away, I'm probably not going to orgasm in a condom. Fortunately I'm usually in a relationship where I don't have to wear one, but it's been annoying with flings, especially when the woman is used to easily making guys orgasm. Another problem is sort of going past the point of orgasm. It would have happened 5 minutes ago, but she was building up to orgasm herself and I didn't want to stop, so I control it and though I'm still hard, the build up went back down. After awhile things start to feel a little numb if the stimulation isn't changing. That can mean needing a position where she can use her hands, fingernails, etc. Or it can mean actually just stopping for 20 seconds inside her. Starting back up is stimulating and feels fresh. Counter-intuitively, if I've been going awhile it's light, gentle touches or scratches that are effective, and not squeezing hard or going fast. Finally, trying to hurry up and orgasm because she's done is about the worst possible approach. In all of these, if I hadn't been concerned with making sure she was satisfied I wouldn't have had a problem. It's a problem of avoiding orgasm when my body actually first wants to, and then having a hard time getting back to that.
I was never to the point that the questioner describes, so this wasn't necessary for me, but see what happens if you make it all about him. Tell him for once to not worry about what you want. Ask what he wants and tell him to just lay back and receive pleasure. Obviously this isn't ideal, but it could be a start if it gets him to the place where he can let go.
I've never actually run across a woman who was too loose. Extreme tightness isn't all it's cracked up to be, and honestly, just makes it slower to get started. Once you're going it's about the movement, not about how tight it is.
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