I was 17... she was 17... we'd gone out for about a year first, and had done plenty of other things, so we were both ready and prepared... didn't hurt her thankfully... who said you can't enjoy your first time? we started out good and have since become sex all-stars
*edit* the issue of hurting or not doesn't relate to member size... for example, I'm around 8"x6", and didnt hurt going into my 5'5" 105lbs gf, but her sister (5'6", 120lbs) got hurt by what her sister estimated to be 4"... her sister has been, well, fingered plenty too, so unuse shouldn't be an issue with that... I hope that made sense...
and Dimitry, you didn't just read that