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My first time was also with a virgin, we were both 16 and had been seeing each other for about 3 months or so. We both decided that we wanted to and waited for the most convenient time (ie her parents to go out!). It did hurt for both of us the first couple of times.
Oddly enough I've been seeing a girl recently who is a virgin and despite her advances on me, a virgin she remains. However she insist she wants to change this and to be absolutely honest I'm scared as I don't want to hurt her.
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