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I'd recommend against it. I'm in a similar situation as he is (minus the incredibly attractive one-sided older friend), and I think it would be something he may regret. It's not really something I'd want to "get out of the way," and as sick as he may be about it I suspect he's the same way.
A big part of it is that losing it isn't something I would later want to regret. I don't care if it makes me feel like more of a man afterward, or does any number of other things. Like every action in my life, I would want losing my virginity to be something I do no later regret.
So I vote against it.
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If ignorance is bliss, you must be having an orgasm.
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