vibrator advice please!!!!

Me and my bf have been dating for three years. We've been having sex for two of those years and I can never orgasm. I've been thinking lately and I think we need to use something during sex so I have a couple questions:
1) what brand and type are the best that are fairly cheap but still good? (I want to be able to use it with him but also by myself)
2) will anything mess with the condom during sex? Like break it
3) I am probably going to order it off of Amazon because I have a gift card. Will they just send it in a normal box? As well as other websites? I have roommates and I don't want them to know 
4) how do you use certain ones and is it awkward during sex
PLEASE HELP