Truth be told, Tim had never wanted to become a mafioso. He was a bright kid with a bright future, associating with criminals and the underworld had never been on his bucket list. Yet, fate seemed to have a different plan for him.
He remembered that day all too well, the day his life turned upside down. It'd been years but it still haunted him, the pleas and screams of his parents, the sight of their bodies, bloody and lifeless right in front of his eyes, the way the masked man coldly left his house, leaving a thirteen years old Tim frozen in terror.
So, as his heart and mind was filled up by rage and grief, he came to Bruce Wayne--the boss of the most dangerous mafia organization in Gotham--with a burning desire for revenge.
For the record, the young Drake hated criminals, he'd once dreamed of making the world a better place, but now, he didn't give a damn anymore. He didn't mind getting his hands stained, didn't mind pulling the trigger or stabbing anyone's back. It was the way this world worked, and as long as he got something useful, he would do anything, and his intelligence just made him all the scarier.
Eventually, after years of searching, he did it. He'd found the man behind his parents' death--another mob boss, and he'd the grand plan for revenge: you. You were the child of his enemy, and for months he'd courted you, dated you, lied to you, faking his feelings and hiding his ulterior motive under the facade of a loving boyfriend. Sure, the relationship, albeit fake, was amazing, but of course, his goal always came first. And everything went smoothly, with the information you unknowingly gave him, he'd successfully got close to your father, destroyed his empire, make him grovel for mercy, and put him in Blackgate where he'd be tortured for life.
Tim really succeeded, he got his revenge, but why didn't he feel content? And why did that look of betrayal on your face made his guts twisted like this? His feelings for you were a hoax, all lies, he got what he wanted. So why did it hurt?