Angelo was staring at him in a way that made him uncomfortable and concerned. Angelo didn’t look at Bobby the way normal men did. He didn’t bounce off the veneer and go away with some glossy impression. He studied everyone he looked at. Bobby didn’t know what Angelo was dissecting now, but he felt himself open and raw.

The plug was uncomfortable. He wanted it out. He was starting to shiver too. Clothing would be nice.

“So,” he said, forcing a smile. “Do you think I could get a sweater?”

“You have been a good boy,” Angelo allowed. “You can take the collar off.”

“And the…” Bobby let his eyes drift downward, even as he removed the collar. Just a simple buckle. He’d allowed that to keep him on his knees. What the fuck was going on with him? Who was he? Was he a man who kneeled before others and let them take anything they wanted? Bobby pushed the thoughts away. This is what Angelo was trying to do, make him question himself. He was just biding his time. Playing along with Angelo. That was all.

“You can take that plug out any time,” Angelo said with a smirk.

“I can?”

“On the condition you understand that it coming out means my cock going in. Removing the plug gives me permission to fuck you.”

Bobby’s eyes widened. “What… Angelo…” He wanted to appeal to Angelo’s better nature, but this man had no better nature.

“My cock, stretching your asshole,” Angelo clarified. “Nice and long and deep. Nice and hard. You’ll be my boy then, won’t you, Bobby?”

Bobby’s cock twitched. Fuck. The dark arousal was rising in him. Everything Angelo said and thought was utterly filthy. Utterly without redemption.

“You’ll wear a condom?”

Angelo’s grin widened. “Do I need to, boy? Have you been giving your asshole up to other men?”

“Fuck you,” Bobby swore, getting to his feet. He might be naked and plugged, but he had his limits. He wasn’t sure quite where they were anymore, but he was fairly certain they still existed in some form or other.

“Pride will get you hurt, boy,” Angelo said warningly, not bothering to rise from the desk.

He could have punched Angelo right in the face, but instead Bobby reached back, took hold of the flared base of the plug and pulled. It was impossible not to wince as the thicker part of it stretched his asshole again on the way out - and Angelo didn’t fail to notice that. He let out a derisive laugh as Bobby pulled the plug from his rear and threw the stinking rubber thing down between Angelo’s feet.

“One hell of a gauntlet, boy. Didn’t know you were so eager to be fucked.”

“You’re not going to fuck m…” Bobby didn’t even get to finish the sentence.

Angelo moved with the speed of a predator. He grabbed Bobby by the back of the neck and slammed him down against the desk. Hell, he was strong. Way stronger than Bobby gave him credit for.

“I told you what would happen if you took that plug out, didn’t I?” He breathed the words against the back of Bobby’s neck, holding him down while he fiddled with his belt and fly with his other hand.

Bobby tried to push up, but Angelo slammed him back down, using his larger bulk to devastating effect.

“You knew,” Angelo repeated. “I just told you, boy. You asked for this.”

“Let me fucking go, Angelo,” Bobby growled, pushing back again. He bucked across the desk, sending papers flying, but Angelo kept a hold of him and even as he struggled, pushed the thick head of his cock against Bobby’s asshole, keeping it right there at the squirming star.

“That’s the last thing you want me to do,” Angelo said, clamping his hand hard at the back of Bobby’s neck. “You want me inside you, don’t you. Say it.”

“No,” Bobby growled, arching his hips. Pushing his ass back. Making it easier for Angelo to take him. “I don’t want this.”

“Liar,” Angelo hissed, drawing his hand back to slap Bobby’s ass hard. “You know you want this. You just want this to hurt because you know you deserve to hurt.”

Bobby drew a sucking breath through his teeth. The cane welts flared underneath Angelo’s hand as the older man started to whip his ass all the while teasing his anus with the head of his cock. It hurt, but the pain felt good. Felt essential. He couldn’t do this any other way. His ass needed to be fucked. He needed to be dominated. He needed to be taken in the most shameful way a man can be taken, his ass fucked like a pussy, taken like a girl.

“I’ll hurt you,” Angelo promised, his voice rough with intensity. “I’ll hurt you like you need to be hurt.”

Tears formed in Bobby’s eyes. Not tears of pain. Tears of sorrow. For everything he’d lost and everything he’d become. Everything he’d always been, right in the depths of his dirty soul. Angelo wasn’t doing this to him. Angelo was just showing him what he was.

“Cry for me, baby boy,” Angelo growled, urging his hips forward.

Bobby let out a little sob. A blob of wetness fell onto the blotter beneath his face. Angelo commanded everything. His ass. His tears. His fucking soul.

“You’re a demon, Bobby, and a demon needs a devil,” Angelo panted as he sank himself himself deep inside Bobby’s ass, his cock claiming virgin territory with a rough thrust which made Bobby let out a pathetic whimper.

He was being fucked. Bare. There was nothing between them, nothing to protect him from whatever dangers lurked inside Angelo. He cried out as Angelo fisted his hair and thrust back and forth, his cock taking advantage of the remnants of lube and the looseness of his hole. With every stroke, Angelo narrated his descent.

“You’re not redeemable, Bobby. There’s no going back for you. Don’t look for a savior. One isn’t going to come. All you’ve got is me, and what passes for my heart.”

Fuck. Deeper. Harder. More. Please. More.

Thoughts fled. No more words. Just the pounding shaft which stretched his innards crudely wide, stroking the gland inside his hole with every back and forth. This was the worst thing that had ever happened to him - and it felt the best.

Angelo’s voice became ragged and he stopped speaking. Flesh met flesh, cock in ass. They were joined. One thing. One writhing, grunting, evil creature. Bobby couldn’t feel where he ended and where Angelo began. He couldn’t understand what he was anymore. He didn’t care. What was Bobby and why did it matter?

Angelo reared back and pulled out before thrusting deep again, making Bobby feel it all. Every inch of his hard flesh, spearing in and out.

Orgasm.

The notion floated to him through the haze of sensation. What was the point of it? He didn’t want an orgasm. He didn’t want this to end. He wanted to be here forever, completely debased.