There are many reasons Adam Milligan hates his father and just the Winchester name in general. One was because his father for most of his life was a no show. Secondly because it's his father's fault his mom was gunned down, because he wanted to play occasional white picket fence, and didn't tell them he was a Mafia don. He hates his brothers who got him involved in the life despite repeated attempts of Adam to get away once he found out.

But what he hates the family the most for is this. Being taken captive by the Angelus family. He was nineteen was the Angelus family kidnapped him, while aiming for his brothers, instead. Nineteen and finally away far enough with a new name, and no Winchesters on his trail. He was burning brightly through Pre-Med, aiming for Med and an eventual Doctors Without Borders, when he woke up to gunshots one night, Dean and Sam showed up at his doorstep, bloody, and turned his whole world upside down. And then the bastards escaped, and Adam didn't, and someone by the name of Zachariah had caught him, deemed him a good present, present for the two heads of the family. Michael – the older brother had taken one look at him, and not even caring about the fact that Adam was fucking wounded, had laid claim to him. That's what he's been ever since. A receptacle for his lust and substitute for the Winchester brother he obsessed over – Dean. And the Winchesters didn't come for him.

-

“You're late.” Michael says as he enters Michael's study not even looking up from the documents he's studying, but the gun trained on him motions for him to come closer. Adam's run all the way here from the other wing of the house, the moment he found out Michael called. He's breathless, panting, and considering he's still made it late: terrified, because it means he's going to be punished for this.

Gulping he closes the door, not bothering to lock it behind him – it's a rule, he can't lock the door whenever he's alone with Michael – and sends a prayer that Michael is in a good mood. And if he isn't, he prays that Michael's ire isn't Winchester related. That's when it means Michael's at his worse. He's far too rough, leaves too many bruises, leaves Adam far too sore.

“What are you waiting for?” This time Michael does look up, eyes harsh, his voice is far too level, and the temperature in the room feels like it shot up. Yep definitely Winchester related. Adam gulps, scrambling towards the desk and trying to make sure his hands aren't shaking as he unzips his pant, and undoes the buttons on his shirt.

The gun is still unexpected after all the times Michael's used it before. Adam's not sure if he'll ever get used to it. It's cold against his skin as Michael trails it down as Adam undoes his shirt, right into Adam's open pants making Adam shudder when it touches his cock (another rule, no underwear); and then right back up again until it's at his lips. He's almost hesitant when he opens his mouth and lets Michael shove it inside. Michael cocks the gun, and Adam forces himself to be as calm as possible, to not gulp or show any more signs of fear. Michael doesn't like him being jittery.

Adam waits for Michael's next move. It doesn't happen, but Michael simply glares at him. Adam realises exactly why Michael hasn't done anything yet. If his mouth wasn't busy around the nozzle of the gun he'd be hastily murmuring apologies. Instead he starts sucking the nozzle as if he were sucking Michael, eyes closed because he's half terrified he's perhaps got what Michael wanted wrong.
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