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Once - in college. I was 19; she was 16.
She had an impenetrable hymen - We tried 3 or 4 times to pop it, but with no luck. Perhaps I wasn't pushing hard enough, but I didn't want to hurt her. Right about that time I went home for the summer, and the plan was for her to see a doctor about it.
Long story short, we never really got back together that fall.
Interesting follow up, though - 12 years later, I ran into her in a bar. She ran up to me and gave me a great big hug, and whispered into my ear, "Don't we have some unfinished business to attend to!!??"
Unfortunately, she was (unhappily) married. Don't think I wasn't tempted, but . . . I didn't.
Anyway, close but no cigar - not once but twice!
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If you want to avoid 95% of internet spelling errors:
"If your ridiculous pants are too loose, you're definitely going to lose them. Tell your two loser friends over there that they're going to lose theirs, too."
It won't hurt your fashion sense, either.
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