Losing the V-Card! Help please?

Lily

I'm 17 years old, and have been in a relationship with my SO for a bit over 5 months now; I feel like I'm ready to get more intimate with him, to check out my V-card. My SO isn't a virgin; he's been with two other girls long before me. We've had some intense foreplay before, but never actual intercourse.

However; I'm terrified of becoming pregnant. We have condoms and he always used the pull-out with the previous girls (so he's very experienced with it), but there's still the tiny chance of becoming pregnant that frightens me beyond belief!

Also, as I mentioned, we've had some intense foreplay before, and while it did feel good, an attempt at fingering hurt terribly bad- I ended up bleeding a tiny bit afterwards!

And hearing horror stories of some friends losing their v-cards too young and regretting it have also kind of made me worry about losing mine. I feel like I'm ready to be close to my SO in that way, but I also don't want to end up regretting it someday.

So my questions to you fellow Glow users are:

How old are you when you lost your V-card? What did it feel like? How much did it hurt? How did you know you were emotionally ready? Do you regret it? Did you ever regret it? And what is the best way, in your opinion, to prevent pregnancy?

(Also, birth control is not an option for me. My parents are very militant when it comes to me and relationships, and insist on treating me like I'm 11).