I don't think society encourages it. I feel the opposite. Like society tries to suppress women's sexual desires. It's the whole "if a guy sleeps around, it's ok. If a girl does she's a slut." It should be, "if anyone sleeps around, it's none of your business unless they ask you, male, female, black, white, purple, gay, whoever."

It's no one's business unless YOU ask for their opinion. And then that's what it remains, their opinion.

And, the first time doesn't have to be awkward and/or painful. Mine was, because I was 14 and didn't pay attention in 8th grade sex education. You can read about anything and everything you want discreetly these days.

If it helps, the guy will probably be more nervous than you, even if he's had sex once or twice. Just google "how to lose my virginity without pain or awkwardness." Make sure the guy knows you're a virgin.

I don't think your first time should be "special" or whatever but I do think you both should be completely sober (date rape can happen easily this way). You don't have to just do it because he's there and you're there and you're bored. At least make sure the guy cares about you as a friend. Things didn't work out between my bf when I was 14. We lasted a whole 6 mths. But to this day we care about eachother a lot and always have. Besides, it's not going to help your self-esteem at all if a guy sleeps with you once because you want to get it over with then goes and tells his friends. I'm a mother now and this is what I would tell my daughter.

Have you tried talking to your mom about it? I'm lucky enough to have an amazing mom who I could tell anything to, even if it made her a little upset.