After you have sex, how long should you wait till you do it again?

1) I have never had sex, but I have tried now twice with my boyfriend, and it has been incredibly painful. It felt like there was a barrier inside me, and the second time I bled. I feel like I am relaxed, and my boyfriend is very gentle and slow, but it still really hurts — more than I think it should. I am able to use tampons — I'm not that small — but I don't know what the problem is. Is it supposed to hurt this much? Could there be something wrong?

2) I'm a virgin, and the first time my boyfriend inserted his fingers in my vagina, it hurt a lot, and I got sore down there. I didn't reach an orgasm, but faked it so he would stop. I didn't enjoy it at all and I was wondering... is this going to happen when I have sex? Is it going to be as disappointing?

Do you think it is ok for boys to masturbate in really tight womens clothing such as bathing suits and bodysuits, tight overalls etc. If not, where can I get some help. Please help me.

My boyfriend went down to the Village last night and came back with a pierced cock and I am completely grossed out by this. Moreover, he wants to have sex with it on, but it is of the type that would definitely scratch my insides up. What should I do? Also, he's thinking about getting his cock sliced into two parts. Alice, he's freaking out on me. I'm scared for him.