Be aware that sometimes guys don't rise to the occasion the first time because of nerves. It's no big deal, and a pro should be aware of the possibility and treat it with the lack of concern it merits.
On the other hand, if that happened with an inexperienced girl you were deeply involved with emotionally, it could lead her to believe that you didn't _really_ find her attractive. So there are things to be said for going into the first time with someone who knows what she's doing.
Losing virginity to a hooker
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Be aware that sometimes guys don't rise to the occasion the first time because of nerves. It's no big deal, and a pro should be aware of the possibility and treat it with the lack of concern it merits.
On the other hand, if that happened with an inexperienced girl you were deeply involved with emotionally, it could lead her to believe that you didn't _really_ find her attractive. So there are things to be said for going into the first time with someone who knows what she's doing.