Follow Your Passion: A Seamless Tumblr Journey
Mafiaboss!Simon, who is a complete asshole to any and every damn one.
Mafiaboss!Simon when he gets absolutely starstruck for once in his life when he realizes the person he had a meeting for deals with was a woman and not a man.
Mafiaboss!Simon getting flustered under his balaclava and his men KNOW it, but you don't.
Mafiaboss!Simon just agreeing to whatever you say unless it's specifics cause he just can't find it in himself to say no.
Mafiaboss!Simon hating himself for thinking of taking you home and doing everything. Sex, cooking, movies. It don't matter. If it's you, he wants it.
Mafiaboss!Simon being crazy respectful, "Ma'am", "Miss", "Mrs. Y/N".
Mafiaboss!Simon going home afterwards to fuck his fist while whimpering your name like a bitch.
Mafiaboss!Simon not having the guts to ask you out till weeks later
Mafiaboss!Simon being absolutely rocked when you both agree to go to his home for the night, and you weren't afraid to fuck him silly.
Mafiaboss!Simon babbling in his thick accent about how good you feel, how pretty you are, and how much of a good mama you'd be to his kids. He didn't mean to say it. But hey? A kink you can use to your advantage for sure.