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go slow and build up to it... you will probably both be nervous, and that's okay, but she will need lots of 'warming up' first. the wetter and more relaxed she is, the less it is likely to hurt... so keep that in mind.
as for you, if you're nervous, you could either cum really quickly or not at all. i was the latter during my first time, so it was kinda nice for her... but don't count on that.
like maleficent said, just do what feels natural and good. i wouldn't recommend getting too crazy or kinky the first time, there's plenty of time for that later. just try 1-3 different positions and see what feels the best to both of you.
and yes, make sure you use a condom that fits... and read the directions on how to properly put one on. if you trap an air bubble in the tip, its more likely to break.
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"Tie yourself to your limitless potential, rather than your limiting past."
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