Let's call him *Bob* Well Bob is 7 years older than me and has been my brother's BEST friend since high school. My parents love him and my brother loves him. We are not dating, I basically just asked him to take my virginity before I went to college and he agreed and we've been sleeping with each other ever since. We're not in a relationship, to put it crudely we are "buddies." Bob cares for my whole family and loves my brother, so I'm still a little fuzzy on why he would go behind my brother's back just for sex.
I trust him with my body and I still talk to Bob about my life problems just like I used to do before the sex.. just now after every conversation we have sex. I've been telling myself that I don't feel anything towards Bob outside the sex, and to be honest I don't know where I stand emotions wise.
I'm feeling torn between my brother and my own selfishness, but I really don't want to stop. So HELP! Do I stop and tell my brother? Do I just stop? Do I tell my brother and keep doing it? Or Do I just keep sleeping with Bob and pray that my family never finds out?

Bob wants to keep having sex and hope my brother never finds out. I want to keep having sex and for my family to know and be totally fine with it. (NEVER GOING TO HAPPEN)

Also any idea how to tell Bob that he needs to use lub because he's too big for me and I bleed every time?

If you have to ask... the answer is no, you should stop.

And if you're bleeding every time, you should be seeing your DOCTOR.

The problems with 'Friends with Benefits' of FBs is it's difficult for emotions to not become involved. He wants sex and you want a relationship. I assume you want a relationship because you all but say it in your post.

It is time to have the 'TALK'. Make sure you're both on the same page. It might be time to move on. Actually it is time to move on.

As for the other issues:
1). Don't ask him to use lube. Tell him to use lube. Go get some from the local drug store/wal-mart/grocery store/sex shop/convience store/etc. and tell him to use it or he doesn't get to insert Tab A into Slot B.

2). Bleeding or discomfort from sex is a bad thing. Blood, with the exception of menstral flow, is indicative of a problem. Vagina tearing or what not. See a doctor.

Um, you're a little fuzzy about why he would go behind your brothers back for sex?

I'm a little fuzzy about why you would ask a family friend to take your virginity...

Simply put - if you think you should stop and you're having doubts - then you need to stop.

Re the lube stuff - you seem not to be able to take responsibility for your own sexual activity - why can't YOU buy some lube and use it in the future?

Just STOP IT! Its so bad,of all people you chose your brother's best friend.. who ever he is isn't worth being a friend to anyone,he is just a green snake under a green grass,how would he feel if your brother was doing sameting to his sister.end it now before things get sour,and pray no one gets to hear about it.

OK you shouldn't be bleeding every time so I agree that you should see your dr. but if you don't want to stop, don't.. you don't have to make a decision today.. wait until you are SURE that you want to tell your family because once you do you can't take it back.. although I do think you should find someone you like enough to be in a relationship with.. trust me you don't want to be with someone who just wants you for sex... hope it helps