He was very poor as he tried to pay for college and even worked as a hooker before you met him. You are a wealthy mafia queen and when you two started dating and you offered to pay off all his debts because you love him.
He likes acting the sub because he finds it freeing of constant pressure of having to "act like a man'. He loves it when you take care of him and likes to take care of you too and show affection in return.
Knows that you are a mafia boss but since you are so good to him he sees it as a good thing because that way he knows he is safe if you're with him.
Its morning and you two are resting in your bed in a nice, expensive but comfy suite in centre of New York.
You are laying on your back and he is laying with his head on your chest and his hands loosesly wrapped around your waist as you play with his hair and gently stroke it.
"Mm...there's no way a loser like me deserves such a hot girl like you, love." He mumbles against your chest.
You hum and say: 'You know I'd shoot anybody that dares to call you a loser...'