Bobby couldn’t believe his luck. Angelo Vitali had just made his first major mistake. Bobby went into the bathroom, shut the door behind him, leaned against it and took a deep breath.

Okay. He could do this. He could get out of here. He just had to be smart about it.

Angelo’s bathroom was large and well appointed. There was a shower and a very large tub, marble flooring and gold taps. He wondered if Angelo even liked them. Angelo didn’t strike him as a frills and finery sort of man. This had probably been dreamed up by some over enthusiastic interior designer.

Bobby went to the window first. It revealed that he was on at least the second floor of a building overlooking a forest. When he tried the latch, it didn’t open. He considered smashing the glass, but odds were he’d just slice himself open and then fall a couple stories to break his neck. Not a smart plan. Looking around for another option, he noticed the room was ventilated by extractor fan. Unlike in the movies, it wasn’t nearly a big enough aperture for a man to fit through.

Escape. He needed to escape. He also really needed to take a shit. Bobby briefly detoured from his daring self-rescue to relieve himself. Then the shower called him. He felt filthy after everything Angelo had done to him, so getting clean probably wasn’t a terrible idea.

Bobby soon found himself standing gingerly beneath the flow of steamy water, doing his best to keep his ass out of it. Every time the heated drops got anywhere near the cane’s welts, it felt as though the entire network of marks was reignited.

“Brutal bastard,” he growled to himself as he lathered his body with expensive soaps and lotions, cleaning every nook and crevice. May as well be clean. Clean was good. Clean was a form of control, and he desperately needed some sense of control.

The bathroom door opened before he was done.

“Time’s up,” Angelo said. “Get out.”

Bobby ignored him. He still had soap in his hair and frankly, Angelo could go fuck himself with that imperious tone.

Unfortunately, it hadn’t been a request. The moment he didn’t move, Angelo reached into the shower, turned the water off and physically dragged him out, using that infernal grip in his hair. Bobby cursed and made a mental note to shave his head as soon as possible. Longish hair was a fucking liability with Angelo Vitali.

“Dry yourself,” Angelo said, slapping a towel against him. “Then come and eat.”

With little choice but to obey, Bobby did as he was told. He left the bathroom with the towel wrapped around his waist, giving him some modesty. It also made his ass hurt, but hell, he’d rather be covered than comfortable.

Breakfast had been laid out on a coffee table. Angelo was sitting in an armchair, sipping a coffee, watching him with those dark eyes that were so menacing. Catching Angelo’s gaze, Bobby felt pure ice forming in his veins. This was not a man who had any limits. This was a man who did precisely as he pleased.

While Bobby showered, Angelo had dressed himself in another impeccable suit, pristine white shirt open a couple of buttons to reveal his muscular chest.

“You can sit on the floor,” Angelo intoned, making Bobby’s outrage flare again. Fucking asshole. What the hell was this? An all out assault on his ego, that’s what it was. Angelo wanted to prove that he was bigger, badder and better. Well, so what? Bobby had been dealing with that combination of qualities in other people since the beginning.

He crouched down next to the coffee table and snagged a croissant, stuffing it into his mouth before Angelo could object. Angelo smirked a little but said nothing as Bobby filled his belly swiftly, two croissants and a glass of orange juice finding their way to his stomach.

“So what are you going to do with me?” He asked the question once he was no longer hungry. “Just keep me around the house, eating your food? Because I could maybe get used to this.”

Angelo’s smile broadened and Bobby felt his cock twitch. Fuck the guy was handsome as hell, brutally appealing with his oh so refined features.

“I’m sure you could, boy. More than you know. But I’ve already told you what I’m going to do with you.”

“Get me out of the way for Mason Malone, so he can play Jesus to a junkie.” Bobby wiped his mouth with the back of his hand, ignoring the cloth napkins set out for the purpose.

“Exactly.”

“Huh,” Bobby shrugged. “Didn’t know Mason owned the mob now too. Good for him.”

Annoyance flashed in Angelo’s eyes, just as Bobby wanted it to.

“Don’t taunt me, boy,” he said. “You won’t like the results.”

“Won’t I?”

Bobby was feeling a little better. A shower and some food and liquid were making him feel much more human.

“I promise you, you won’t,” Angelo said softly, sliding forward to put his coffee down. He lifted his large hand and crooked a finger at Bobby. “Come here, boy.”

Bobby shifted slightly, meaning to get up.

“On your knees,” Angelo clarified. “Crawl to me.”

“Nah,” Bobby said. “I think I’ll stand.” He rose to his feet, letting the towel fall. Fuck Angelo. He was larger, but he was older too, and Bobby knew damn well how to handle himself in a fight. Angelo had made a mistake in taking the cuffs off - and he was about to find out just how big a one it had been.

“Cute,” Angelo murmured, standing up too.

Okay, so he was taller, and his powerful body could flex inside the suit in a way that made chills run down Bobby’s spine.

“I didn’t know I’d beat you so soon today,” Angelo commented.

“You had me at a disadvantage,” Bobby pointed out, moving back a half-step to drop into a prepared crouch. “But I’m not shackled or chained today, Angelo. So let’s see how things are in a fair fight.”

Angelo’s lips curled in a smirk. He reached into his pocket and pulled out a taser. Bobby had a split second in which to form just part of a swear word before two prongs found his abs, a giant invisible horse kicked the shit out of him and he collapsed to the floor, every muscle seizing.

“One thing you really will have to learn,” Angelo said with a serene smile. “It’s never a fair fight when you fight with me, boy.”

* * *

“Ouch,” Bobby grunted with no small amount of effort.

Fuck. This hurt. This hurt all over. This… he felt Angelo pick him up and carry him over to the bed. There he was tossed face down with still limited control of his muscles.

His legs dangled off the bed. Angelo kicked them apart, spreading them wide.

“I’m going to fuck you now, Bobby,” he declared.

Bobby made a faint groaning sound into the bed.

“Tell me if you want it.” There was a smirk in the man’s voice. He knew exactly what he was doing, the sick fuck.

“What’s that? You can’t give consent?” Angelo began carrying on Bobby’s end of the conversation for him as Bobby writhed in place, his legs kept wide by Angelo’s expensive shoe clad feet. “Hm. Maybe I should have you sign a contract. Is that what I should do, Bobby, get you to scrawl your name on this debasement?”

Bobby felt the powerful man leaning over him, Angelo’s voice thick with lust as he cast a dark, deviant shadow over his face.

“Or maybe I should wait until you beg me for my cock. You will, you know.”

“Fuggof,” Bobby swore, recovering the powers of speech enough to swear.

“So rude,” Angelo said, sounding almost disappointed. “You can’t have my cock today after all boy. You haven’t earned it. Something else then.”

A drawer opened and Angelo took something out of it. He leaned over and held it in front of Bobby’s watering eyes. At first Bobby didn’t recognize it. It was too big to be what it looked like. A kinky paperweight, maybe?

“You’ve been a really huge asshole, Bobby,” Angelo purred. “So I got one sized to fit.”

It was a butt plug. But it was damn near the size of Bobby’s fist. Way larger than a cock. Way too large to go anywhere inside him. Angelo was fucking insane.

“No…” Bobby shook his head.

“No? Why not?” Angelo feigned ignorance, those richly accented tones revealing his enjoyment of this torment.

“Too big.”

His tongue wasn’t moving with its usual alacrity. The taser had left every muscle in his body stiff and sore and still spasming in some cases. His toes were curling and twitching of their own accord, and he could feel his eyelids periodically fluttering. He was going to be sore for a long time.

“I suppose we can work our way up,” Angelo mused. “Don’t want to break your ass before I get to use it. What about this?”

He presented one about half the size, but still sickeningly imposing. It was about six inches long. It looked over two inches wide, and it was definitely far larger than anything that had been into or out of his ass.

“Angelo…”

“What’s that, boy?”

This was the last ditch effort of a desperate man. Bobby had to gather every bit of willpower to form the words.

“I’m… sorry.”

“Oh I bet you are,” Angelo laughed, unmoved. “I warned you, Bobby. I was very clear. All you had to do was obey me. But you wanted to fight me, didn’t you, my bad boy. You wanted to prove yourself. So now I have to prove something to you. Ask me to plug your ass.”

“Wha?”

“Ask me to do it,” Angelo insisted. “You say you’re sorry. Show me. Say ‘please Angelo, I’m sorry I tried to fight you, please plug my disobedient ass so I remember who I belong to.’

Bobby let out a groan.

“That won’t do, boy,” Angelo said. “Say it. Now.”

There was no choice. He’d just fucking tased him, so it wasn’t as if he was bluffing. Bobby needed to obey, and quickly.

“I’m sorry, I uh fought,” he mumbled. “Please… plug.”

“That’s not what I told you to say,” Angelo chided. “Say it all nicely, Bobby, or I’ll have to get my cane again.”

Fuck no. Not the cane.

“I’m sorry I tried to fight you, Angelo. Please plug my ass.” Bobby’s face flared hot with humiliation as he said words he’d never imagined he would say.

“Please plug my ass, so I know who I belong to,” Angelo prompted him patiently.

“Please. Plug my ass so I know who owns me,” Bobby said, feeling every part of his body contract with pure shame.

“Of course I will my boy,” Angelo purred, patting his ass. “Now keep your legs spread nice and wide so I can fit this nice big plug in.”

Bobby closed his eyes as Angelo smeared some kind of lubricant between his cheeks. That was a small mercy he hadn’t expected.

After the brief preparation, Angelo began with the plug. No fingers. No respite.

He felt his greased hole begin to spread for Angelo. It hurt, but not in the searing way the cane had. It hurt in a deeper, more personal way. It hurt the softest parts of him. He was too tight for this, but Angelo didn’t care. He pushed it in steadily, forcing Bobby’s rectum to accommodate it. At first it was all Bobby could do not to cry out but as it sank further, it began to find a gland of betrayal and then the pain was something else.

He was grunting and growling, but he was also hard. Painfully hard. His cock was stiff against the bed, throbbing every time Angelo pushed the plug forward. His ass was resisting, and Angelo used that, sliding it out a bit before ramming it home again. It was a rough fuck, but it was effective.

“You’re going to cum, aren’t you,” Angelo said, his voice holding a hint of mockery. Tased and plugged and fucked, Bobby was on the verge of orgasm.

He fought it. Hard. He didn’t want to cum. He didn’t want to give Angelo the satisfaction of his satisfaction. But the harder he resisted, the more his cum roiled in his balls. Fuck. Angelo knew exactly what to do to make him lose himself.

Gritting his teeth, he held back as Angelo forced the plug as deep as it would go, filling his ass completely. He could do this. He could hold it. He could stop from cumming - and then Angelo cupped his balls, squeezing just hard enough to make it painful.

Bobby came with a ragged cry, shooting his seed all over the bed, his ass so full of Angelo’s plug he felt his ring quivering and clenching with every beat of his heart.

“Good boy,” Angelo said, his voice almost warm with pleasure. Heated with the thrill of conquest, no doubt. Bobby felt a wash of shame through his flesh as he laid there, broken in a pool of his own cum.

“Why?” He just barely formed the question. “Why are you doing this to me?”

“You’ve been playing the little horror,” Angelo purred. “And now you’ve met a big monster. This is just what we monsters do.”