I am in a May to December relationship.
It sounds like your bf is not old enough to be financially self sufficient so he can make decisions without the economic blackmail that his mother is pulling.
You said, "he is involved in a lot of sports so it would be almost impossible for him to maintain a job and school at the same time."
I have to say it sounds like you're dating a boy. And I mean a BOY as in too young for you. I think his mother has every right to want to protect her CHILD -which he is. I also want to point out that you're talking about a guy who isn't really old enough to know what he wants or what is possible for him - in relationship, career, etc. Frankly, I think you're robbing the cradle.
I think you need to do some internal searching. Why is this kid so attractive to you? Is it his innocence and immaturity that an appeal? Does he remind you of your first husband when he was that age? Is that a time of life you want to re-live? If so, then you need to do some work on yourself. It would not be fair to ask this young man to choose between his family and you. I think you need to be the grown up here and tell him to go home and find out what he really wants in his life. I think he'll be glad you did.
Good luck. And get busy working on yourself...and go find someone your own age.
I was wondering how his mom could "send him away" to go to work until you said he is still in college, so I"m assuming that he's only around 18-20 yrs old and you're 36-38.
You need to wake up and smell the roses!
Thank you for all of your replies.
Ok after reading through all of these posts again there are a few things I would like to say.
This situation can be looked at in a number of ways.. I do think the boy should go to school and grow up and all and I think OP you should let him go in love.. I mean he doesnt seem mature enough to handle this whole situation if he has to keep running back to his mommy for money and support. Yes; it would be different if he had a good job , could support himself and lived
You don't need a 20 year old friend.