Should: When you know the guy, or girl if so inclined, and know about safe sex. That could be when you're 14 or 34.
Did: Just after turning 21 & starting to come out. First guy was hot but had issues, and our one hookup ended way too fast.
Second guy had it goin' on "downstairs" but in his case the saying "His brains are between his legs" was true.
Then there were the months of clingy phone calls & voice mails after I dumped him. The fifth
and I had an insane time in the sack, for hours, but was also a one-hit wonder.
And so on. But with the chance to do it all over again I'd've saved it for Guy #5. Of course with the chance to do it all over again I would've lost all my cherries to the friendly redhead basketball player who drove my imagination wild in 10th and 11th grade!