As for gynecologists, I think it´s best if you ask a friend or relative to recommend someone they´ve been to so you´ll be certain that he/she is careful and a good professional.
I´ve had my share of scary gynecologists, but in my case the male ones were mostly much gentler so it´s really a matter of luck I think. The last one I visited for routine exams (the pap smear) was a woman and she looked kind enough but she hurt me (it never hurts me when they do those exams) and at the same time made very unkind comments about my body, like "oh nooo you´re sooo thin, ugh" - a real doctor out of hell type of lady. She kind of brought me down but after a while I just got mad at her, I suppose she was being neurotic for her own personal reasons. But I´m not ever seeing her again!
(Anyway, not to frighten you blackhippie, I´m sure this gyn wasn´t the norm!)
And about losing your virginity, well you can take it seriously or not but it will affect you anyway. As a teenager I was stupid enough not to take it very seriously, I just wanted to not be a virgin because all my friends weren´t, and so I went to bed with a guy I didn´t much care about (though he was very attractive physically). Anyway, I think that´s why it hurt. I think it would´ve been much easier if I had been really in love with him. But anyway, I broke up with him very soon afterwards and had a hard time trusting other guys enough to do it with them, even if I liked them. So in all, I think it made me very insecure.
Of course, some years later I met a wonderful guy and with him everything went very smoothly and pleasurably because we had great communication and were very much in love. But now, this older and wiser boobie friend of yours will recommend: don´t rush it!!! It will happen anyway, and better later than sooner!!!
take care,