Hi! I'm seventeen, and my boyfriend is sixteen. We're both virgins. We've been dating for about a year, now, and I believe I'm ready to have sex, and I trust him with my life. The problem is I really dont' want to get pregnant. He knows how to put on a condom, and he's masturbated with one on (testing) with no problem. Should I go for it?

Also... does it hurt the first time? How's it like? I'm not expecting a hot session or anything, I'm actually expecting something like a chore, since I'll probably be in a lot of pain.

If you feel confident enough to take on the responsibility that accompanies becoming sexually active, then you might you are ready. Only you can know if you’re prepared and willing to relinquish your virginity, and I can’t tell if it’s the right moment or not. However, you and your boyfriend have done your research, seem prepared, and already practiced using condoms, which is great.

Everyone’s first time is different, and yes, sometimes it does hurt. If your hymen is very much intact, there will some skin ripping, possible bleeding, and pain the next morning. However, don’t let these temporary side effects deter you. I’ve described the pain before, but it won’t last forever. You will be able to have sex without pain and enjoy it. Just remember, like with any talent or skill, no one gets it right the first time.