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From one perfectionist to another, don't plan....FEEL. The first time will never be perfect, that's just life. It will never feel as good as the 30th time or whatever. If you are sure you are ready to have sex, relax, and stop thinking.
I will add one thing that may be deemed negative. Be absolutely sure that this is what you want. I have seen several friends of mine decide that they are ready to have sex with their boyfriends (saying how much they love each other) only to break up with the guy 2 months later and end up bitterly regreting their decisions.
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I didn't lose my virginity, I know exactly who has it!
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