Juliebees is right...the best thing to do is relax. When you are afraid of the pain of what is coming, your muscles tense up thus making the vagina tighter. Lubes will definitely help (unless you feel that you produce enough on your own). All you can do is ask him to go slow to start. I'm in the same situation as you (only I didn't have sex for almost 2 years). I was single for a year and I dated my current boyfriend for almost a year before we had sex for the first time (...I don't know why I waited that long! trust me it was hard)...but anyways, I just relaxed my body when he was entering and usually started in the missionary position (since the woman is the most "open" in this position). When you feel ok with that, switch positions and see what works for you. If he cares for you he will want to make sex pleasurable for you as well and he will move at the pace you are able to move at. GOod luck and have fun!
Teresa
My boyfriend is both long and wide. Everytime we do it, it hurts pretty bad when he first enters. He often stretchs me out with his fingers before he enters me. The best advice I can give you is to relax and use lots of lube!
A hymen does not re-grow, but the tissues around the vaginal mouth do get tighter with time if they are not widened by "use" so to speak. A friend of mine's mom had no sex for about 20 years, and she (the friend) told me that her mom's doctor used the phrase that she was "almost like a virgin" at that point. I empathize with you about the new boyfriend's shape. Men get this goofy idea from porn films that a big size is cool, but boy, it can hurt. I had a boyfriend who was built sort of fireplug-like in that department, and frankly, sex with him was never very fun. He wasn't long as much as wide, and even a lot of lube didn't help very much. Anyway, try lube and a lot of foreplay, and see where you get. Good luck!