Angelo had never indulged in anything other than short term passionate flings. It was easier to find and fuck someone than try to bring them into his world. But Bobby was already part of the world, and had to be kept close. Very close. For both their sakes.

Bobby didn’t understand, but he didn’t need to. All he had to do was obey. That was significant challenge for a boy used to calling the shots, but Angelo’s cane stood at the ready to remind him if necessary.

It was strange, to wake up in the morning and have Bobby there, snoring softly next to him. The boy spread out in his sleep, forcing Angelo to the edge of the bed to the point Angelo considered tying him up before bed to keep him contained.

As the days went on, the situation became increasingly intense. Bobby’s stubble was left in the bathroom sink. He farted under the covers. It was all getting incredibly domestic - in spite of the fact theirs was a relationship of captor and prisoner.

Angelo was used to being surrounded by a staff and a slew of bodyguards, but no other people in his personal space. Work usually dominated his day, but with Bobby it was often a matter of spending his day dominating the boy.

Bobby was raw in so many ways. He had all the makings of a boss, but he lacked the maturity to do what he needed to do. Angelo was taking advantage of that inexperience, but to his mind, he was also taking care of Bobby at the same time. Bobby was damn fortunate that Mason Malone had chosen Angelo to take care of the situation. Most other people in his business would have settled things with a bullet.

Now, as he stood and stared at the wreck that used to be his private bathroom, Angelo wasn’t so certain he hadn’t made the wrong choice.

“Bobby!”

“What?” Bobby lifted his head from the bed where he was napping - at two o’clock in the afternoon.

“Don’t say what to me, boy,” Angelo growled. “Clean up your damn towels.”

“Prisoners don’t have to clean.”

“Prisoners get their asses fucked if they’re not careful. Is that what you want?”

“That happens if I am careful too,” Bobby shot back.

“Bobby, boy. I am not playing,” Angelo growled. “Clean this room up. Now. This is not a frat house. This is my bedroom.”

“You have staff for that.”

Attitude. The boy was daring to talk back to him. Bobby needed a refresher in manners.

Without another word to his impudent brat of a prisoner, Angelo went to retrieve his cane. It was in the corner of his office, along with a few other implements Bobby was going to be introduced to if he wasn’t careful. Just as he picked the cane up, his phone rang. A familiar and fairly important number flashed on the screen. He would have to take this call. Bobby could wait.

“Mason, how are you?”

“I’m well, Angelo. How’s your guest?”

Angelo allowed himself a dark smirk. “He’s suitably distracted.”

“Really. Because his men are still sniffing around my compound.” Mason’s voice was clipped and tight. “Get a proper handle on him, please, Angelo. Or our deal is off.”

Mason ended the call abruptly, leaving Angelo displeased. It hadn’t occurred to him that Bobby still had outside actors capable of acting independently. This was a surprise, and Angelo did not like surprises.

He walked back to the bedroom, tapping the end of the cane against his leg. When he got there Bobby was sitting in the messy bed wearing nothing but a pair of black boxer shorts and reading a paper. He apparently considered their conversation to be at an end. He was very wrong.

“Well,” Angelo said, lifting the cane to whack it against the palm of his hand. It left a searing mark, but it also made enough noise to get Bobby’s attention.

“What?” Bobby gave him a guarded look.

“It seems your men have been carrying out orders. Your orders. Strange, given you can’t pay them anymore.”

“I guess they haven’t got that message yet.”

“Call them off, Bobby.”

Bobby sat up straighter, cocking his head to the side. Suddenly Angelo wasn’t talking to his little fuck toy captive anymore. He was talking to the man who had Mason Malone and half of New York on the run

“Why should I?”

“Because I’ll hurt you if you don’t.”

“You’re going to hurt me anyway,” Bobby said calmly. “You’re keeping me captive. I have no assets. No freedom. You have no leverage with me anymore.”

Little shit. Angelo kept his calm though. He was actually enjoying this dark sparring immensely, much more than Bobby’s domestic ineptitude.

“I’ll turn every part of you into leverage if you’re not careful,” he threatened. “Turn over boy, pull your underwear down. Let’s see how this cane makes you feel.”

Bobby gave him a cold stare of pure hate which only served to excite Angelo. Whipping this deserving boy’s ass was going to be one of the highlights of his day.

“If I have to put you into position, I’m going to whip your ass hole before I fuck it.” He let the crude threat hang in the air between them, loving the way Bobby’s face paled even as his eyes narrowed.

“You’re making a mistake, Angelo,” Bobby said, sounding ever more petulant. “A really, really big mistake.”

“I’ll give you my phone and you can call your people off after I cane you.”

“You can shove your phone up your ass,” Bobby snapped. “I don’t give a shit what you do to me. My men are going to find Aiden and make sure he gets what he deserves.”

His temper had betrayed him, as it always did. Angelo stepped forward, closing the distance between them. Bobby needed the cane - not because of his attitude, or because of his refusal to acquiesce, but because he would never amount to anything if he couldn’t control that impulsivity which made him give everything away.

Bobby fought, as he always did. Then he lost, as he always did. It wasn’t hard to wrestle him down and pin him in place, but it was fun to let him tire himself out, his hot writhing body kicking and squirming in protest. In the end, Angelo mounted him from behind, an arm around his neck, cutting off oxygen enough to make further struggle impossible.

“Stop fighting me,” he growled in Bobby’s ear as he crouched over the boy’s body. “You won’t ever win.”

“I’m winning right now,” Bobby squeaked back.

“How do you figure that?”

“My men are still looking for Aiden. They’re good too. They’re going to find him. They don’t give a shit about you holding me here. They trust me to get out.”

“Maybe I need my men to pay your men a little visit,” Angelo said. “How many pistol clips will it take to deal with your men, Bobby? How many of them are prepared to die for you?”

“Fuck you,” Bobby growled, furious. “You better not touch my men.”

“I’ll do whatever I like to them. Because they’re not your men anymore, Bobby-boy. They’re mine. I own you. And I own everything of yours.”

“You don’t own fucking anything,” Bobby said. He was going to go on, but Angelo had enough of the conversation. This rebellion wasn’t getting either of them anywhere. He tightened his arm, cutting off the flow of blood and oxygen even more. He felt Bobby go limp under him before he eased off and stood up. Bobby was still out. No problem. He could fix that.

Looming over Bobby’s inert body, he lined the cane up and brought it down with a hard CRACK.

Bobby screamed back into consciousness, his eyes wild and red with almost instant tears. Angelo brought the cane down again, catching his ass a little lower. Bobby tried to get up and get away, but Angelo reached down and caught him by the boxers, using them to hoist Bobby into a wedgied position as he slammed the cane against his deserving backside, the Lexan biting into Bobby’s skin over and over until there were a dozen lines crossing his rear and the little mafioso was crying out like a baby.

Angelo released him then, dumping him back onto the bed unceremoniously. “Go clean the bathroom.”

Bobby’s face was contorted and red with the pain of the punishment as he gingerly got up from the bed and did as he was told - as he should have done in the beginning. Angelo stood over Bobby as the boy went to the bathroom and gathered the towels, catching Bobby’s thighs periodically with the tip of the cane if he moved too slowly.

“Was that so hard?” He smirked the question when the room was suitably cleaned. Bobby didn’t reply. He was too busy wiping the tears he was trying not to cry from his cheeks and avoiding Angelo’s gaze.

Angelo held out his phone to Bobby. “Now, call your men off.”

“No.”

“No?” Angelo’s brows practically hit his hairline. “Boy…”

“Choke me out, beat me, I don’t care,” Bobby said, staring defiantly all of a sudden. “Aiden is a dead man, I swear it.”