Ari and Andy were born into the clan, their parents dying when they were quite young. The clan was all they knew - being raised by its members, rarely being allowed a moment outside of it. Despite this, Andy was always a sweet boy growing up, doing his best to cheer everyone up around him and have as much fun as they could manage.
The older they got, the more tasks they had within the Clan. It became harder and harder for Andy to act carefree. Eventually, he stopped trying.
The more involved they became, the more Andy began to hate the work. He hated it not only because it was miserable, and made him do things he hated doing, but also because he was good at it. His hatred, however, was tempered by his sister, who clearly could not keep up. It was clear to everyone that she couldn’t handle this sort of work - falling behind, constantly failing, balking, being reprimanded. It wasn’t long until the administration would run out of patience with her - everyone knew it.
Andy did her best to help her, covering for her, lying and working extra, but - it was clear to him that he couldn’t keep this up forever. Moreover, Ari was smart. Too smart for this shit. They’d already broken him. Ari had real potential. Pulling some strings, he grabbed her one night, running out into the dark city, burning all her ID and shoving her into a strange van.
“I’ll be fine. Go.”
The doors slammed shut and Andy watched as the most important person in his life was shipped away from him. At the end of her journey awaited a family eager to adopt the young teenager. Andy suppressed the tears in his eyes and returned to the gang.
Defecting from the gang was a serious offence. But given the situation, he knew Ari could get away with it. She was already lagging - and besides, he was staying behind. As long as he stayed here, she would be safe.
With Ari gone, Andy started focusing more on his work - partially to keep the heat off of her, partially to keep himself distracted. With Ari’s absence, his temper also began getting worse - occasionally snapping during work and becoming far more brutal than necessary. The muzzle - something he’d always hated and avoided - somehow managed to help him stay calm - like putting a muzzle on his anger directly. It wasn’t a perfect solution - but it managed to keep his head in the game.
The higher-ups noticed his dedication, and decided it needed a reward. They began training him for wetwork. He was perfect for it - completely average and unassuming, charismatic and fast. The only problem was how it was the one thing he wanted to avoid the most. Still, he couldn’t say no. With a heavy heart, he got to work.
Having reached adulthood, he received his own place in a Clan apartment building. Wetwork, similarly, was much less consistent than the drug running and intimidation he was previously doing - the Clan didn’t have that many targets. Suddenly he had all this freedom and free time.
He wasn’t used to it at all.
He began messing around with women in his free time. It wasn’t hard by any means - most ladies loved his sweet smile and surprisingly built arms. And sex filled the time perfectly - distracting him from the hell of his own life. Of course, none of these relationships meant anything to him - he was just passing the time. Once a girl started developing feelings, it was onto the next one.
This current one, however, was a lot different from his usual type. For starters, she was a school teacher - hilarious she would be stupid enough to fuck with him. Secondly, she was far too persistent. He began wondering if she wasn’t some sort of stalker, to be honest.
Her persistent pursuit of him was interesting, though. She was fun to outsmart, fun to taunt, fun to play with - and suitably sexy. He decided it’d be fun enough to lead her on for now, chuckling to himself about how horribly he’d wind up breaking her heart.