To do or not to do...I trust u guys so let me know. Options

[loveneko]

I'll be Anne, my best friend is Elle, the guy I like is Jack, and my best male friend is Bobbie.

I've known Jack for 4 years, and I've liked him for all four years, and through two boyfriends. I've always wanted to go out with him but he used to have this crazy crush on my best friend Elle so it never happened. Also, I don't know if he likes me, he says he has, and his friends say he still does but he's shy. Well I told him I like him. I broke up with my last boyfriend a bit of while back, he cheated on me, so Im not going to dwell on him.

Now, background info is really irrelevant, I think, so Ill get to the point. Jack is a virgin. I'm not. I was raped when I was little and Ive had sex since then with a past boyfriend. So while Im no pro, I know what to do. He knows my history and what happened to me, he's ok with it.
Jack is the Salutatorian in my school, I rank a few digits below him. I do his schedules, I correct his essays, I act as sort of a secretary for him. (Ive got it bad for the guy)
So we're both known for our smarts in my school, people are dying to see us go out, but he doesn't want to go out with me. He says its because he wants to be single so he can focus on his schoolwork, but we act similar to each other and I wouldnt waste time talking to him instead of doing my work either, so I dont understand how that works.
He would however, like to lose his virginity, and who else to lose it to, than to me? I dnt want him to be using me as a test dummy, but I want what he's offering me and I have the notion that if he loses it to me, he'll fall in love with me.

I dont want to fall in love with him though, but I know I more than likely Ill do just that. I want him though, Ive always been the gawky, nerdy girl, I play sports, Im athletic and the guys consider me a guy. Thats my problem. Jack had such a major crush on my best friend because she was hot, she had a great body, all the guys in my school worshiped her, she was popular. I was just her friend, and I hadnt "come out of my shell yet" as she likes to say. Now thats hes offering me his body, I want it, he's never been in love, he's inexperienced and I want to be his first, but I dont know if I should.
My best friend Elle says I shouldnt because Im not supposed to be sleeping with people in our circle of friends and there are no exceptions.
My best guy friend says its my choice, because Ive liked Jack for so long, he cant see how I would get past it, and that I should just get it out of my system now.

What do you guys think? Should I sleep with him? Should I not?
I want to, but I want to hold out until the end of the school year. I still want to come dangerously close though, what do u guys think?