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The how and the when really aren't things that I find important in my life. As for Part II of your question: I much rather prefer sex with the experience I now have, since I find the sharing of pleasure - and the intimacy between two people who aren't always fumbling for something that feels good - to be terribly more erotic and arousing!
Good questions, though!
I would like to add one thing: a query, if I may....
Is there a particular reason why you are now questioning along these lines?
I thought about it, and can only come up with two reasons for this: you're either feeling regret or some other detrimental emotions regarding the loss of your virginity OR you're trying to decide if you should lose your virginity.
If the latter is the case, then you need to decide based upon what you feel and believe - not what other people tell you. All I can do is wish you well in whatever choice you make (assuming I'm right about this) and tell you not to regret whatever your choice may be.
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