I'm guessing he's doing a bit of both because he's self-conscious about it - probably from watching too much pr0n or something. It's the same thing women do when you all ask if you look fat or say something like, "I don't want to go out anymore, I look terrible in this outfit." You all know you look just fine but you want your boyfriend to say it to you so that you can feel better about how you already feel you look.

For the record, I HATE people who fish for compliments. Mostly because I like to give genuine compliments, not because you decide you want one. Your boyfriend is doing just that. He wants you to say, "no baby, you're packing just enough for me." That serves two purposes for him: 1) it compliments him by letting him know that what he's working with gets the job done; and 2) it alleviates any issues he has about his size. Basically, the dude has some esteem issues when it comes to his schlong.

Now, I can imagine it being very annoying. Like I said, I hate when folks fish for compliments, especially if I'm generally complimentary towards them. So perhaps you should just let him know that you like what he has and wouldn't be with him if you didn't and there's no need to continue to ask about it. By the way, I'm only suggesting this because he's a man and men shouldn't be this way. I'd never suggest that women stop asking for compliments. I might not like the fishing, but I'm not crazy either. Compliments-on-demand seem to be a woman thing so I can accept and live with that.

Contradiction, thou art my bride.

It was written.