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Truth be told, I was blacked out when I lost my virginity, so I have no recollection of any of the sensations that occurred, pain or otherwise. However, the person I was having sex with told me that he had no idea I was a virgin (after I told him), so it seems that I didn't have any trouble.
The only time that I have had trouble with sex was when I started having it regularly (with ktsp--the only person other than blackout-guy that I've had sex with), and sometimes my muscles felt like they were clamping up... a bit like vaginisimus, and most likely due to all the fear/guilt/processing I was going through at the time, having pre-marital sex after a long and intense religious period of my life, and my mom was outraged that I was having sex before marriage (I was 24 years old!).
I used tampons (the first one of those was rough, very painful, but that's because no one was there to show me how to do it), and also rode bikes like crazy, masturbated, etc... so maybe all of that helped with the whole hymen thing. I guess I'll never know, nor do I think it matters very much at all. Then again, I know women who are virgins (30 years old) who will not use tampons at all, because they're afraid it will break their hymen and make them unmarriable. (They live in a different culture.) It's pretty messed up.
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And think not you can direct the course of Love;
for Love, if it finds you worthy, directs your course.
--Khalil Gibran
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