I feel like you (and us JJBers) still don't have a full answer on WHERE his money goes.

Even if you both have iPhones (I think those are about the most expensive cell phone plans now, right?), that should only be about $200-300 per month.

So where is the other $1,000 or so going?

And if he knows how to drive, why can't he just borrow your car when you are at home? I'm not understanding why YOU have to drive him somewhere. (And doesn't Boston have pretty good public transportation? Why can't he take the bus/train or hell, bike it?)

And I think you really need to figure out why you are okay with lying to your parents. People who, by your own admission, have been supportive of your educational goals and who are footing your bills (and don't they ask why they don't need to pay for your cell phone?). This is how you repay them? By living with a guy out of wedlock (which you know they don't like) AND allowing them to pay for this guy unbeknownst to them (honestly, how would YOU feel if you were footing the bill for a complete stranger?)?
Unless this is some payback for them being crappy parents or something, I actually think it's pretty crappy of you to sneak your boyfriend in on their dime.