Archive of Our Own ^beta

Sam Campbell was probably one of the few people on the planet who truly enjoyed Monday mornings. And why shouldn’t he? Monday mornings he got to walk into a tall, impressive building, take the elevator to the top floor, and step off into the offices of Campbell, Moore, and Brady. He had top billing in the top law firm in the city. And as he’d tell anyone who asked, the view from the top was quite enjoyable.

Particularly on Monday mornings. Because on Monday mornings, Sam arrived at the office early to switch out his secretary’s chair. Most days, the one at his desk was your standard-issue office chair. But tucked away in a closet in Sam’s office was a second chair. This one was a custom job; very expensive and worth every penny. Because mounted right in the center of the seat was a dildo, made from a mold of his own impressive cock. The lower half of the back of the chair was open, which meant that when his secretary sat in it, their ass would be perfectly displayed for Sam at his own desk behind theirs. The angle was such that unless a client or employee were sitting in Sam’s chair, or they actually walked behind the secretary’s desk, they couldn’t see anything.

His current secretary was a man named Dean Winchester. Sam was honestly surprised that Dean had stuck with the job so long—most of his secretaries lasted only a few weeks before storming out with a handsome severance check for their trouble…and their silence. But Dean had been there for three months now. Which was fine with Sam; he definitely enjoyed having the man working under him.

When Dean arrived at five to nine on Monday morning, he stopped dead when he spotted the chair, his cheeks flushing. Sam smirked as he leaned back in his own chair, looking pointedly at the clock. “Not much time, Dean. Unless you want to sit down as you are.”

Dean stared at him hard for a moment, and Sam thought that Dean might have finally had enough, that this would be the day he finally quit. But then Dean shrugged his coat off, hanging it on the rack by the office door before he reached into his desk drawer and drew out a small bottle of lube. He squeezed some out onto his fingers and then slipped his hand into the back of the waistband of his pants, causing Sam to chuckle and shake his head.

“No need to be modest, Dean.” Sam let his eyes flicker pointedly to the man’s belt and then back up to his face. “You know what I want.”

Dean gritted his teeth, biting back a sharp remark. The man had a biting tongue, and it was one of the reasons that Sam was absolutely sure that Dean secretly loved the things Sam made him do. The man probably knew of sixty different ways to tell him to fuck off, but he just glared at him before he turned around, hands quickly undoing his belt and then pushing his pants and underwear down in one quick motion. He braced one hand on his desk for balance, bending slightly at the waist, while the other went to his ass, a slick finger working into his tight hole.

Sam’s eyes flitted to the clock and then back to the fantastic sight of Dean fucking himself with his fingers, opening himself up to take the replica of Sam’s cock. “Three minutes, Dean. And then it’s business hours, so if you’re not seated someone may just walk right on in.” He smiled as Dean added another finger with the comment, twisting and stretching himself. Sam’s dick was hard In his slacks as he watched those thick fingers thrusting deep into the man.

When nine o’clock in the morning officially came, Dean was sinking down onto the dildo, the thick cock too much for his barely-prepared hole, the burning stretch setting his nerves on fire as his face flamed with humiliation. He didn’t think that the lawyer would actually unlock the office door at nine unless Dean was seated, but he wouldn’t put it past the man, either. God, if he didn’t need this job… If it didn’t pay so well… There were a ton of ifs that he used to excuse why he couldn’t quit. And almost none of them had anything to do with the tiny thrill that raced through his gut as his body adjusted and the pain began to ebb, leaving only a deep, full feeling where he was stretched open.

Sam watched as Dean shifted his hips slightly, his body tensing against the rush of pleasure that Sam knew would course through him as the thick toy rubbed against his prostate. “You know the rules, Dean.”

Dean didn’t answer him, but he went perfectly still. He wasn’t allowed to get off unless Sam gave him permission, which wouldn’t come until the end of the day, if at all.

By the time the lunch hour rolled around, Dean was about to go out of his mind. Clients and other workers filtered in and out of the office frequently, making his heart pound with fear and his face flush with embarrassment as he imagined one of them discovering what was going on, coming around his desk for some reason and seeing his ass stretched wide around the base of the fake dick, his own hard flesh leaking as he tried desperately not to give in to the need for movement, not to brace his hands on the armrests of the chair and fuck himself to completion. His cock was throbbing with need, inner muscles quivering. He hated it and loved it all at once, the humiliation of such a public display warring it out in his mind and body with the raging need to at least sate himself from what he was being forced to do.

Sam watched him squirm, sharp eyes tracking every minor movement as the man went through his daily tasks, each slight movement causing the dildo to shift a little in and out of his sight. His hand palmed his own hard cock firmly, the fact that he was essentially watching his own dick split the man wide open all day filling him with a slow-burning need.

When the clock on his desk flashed to noon, he stood up and moved to lock the door of the office, a smirk playing at his lips as he turned to look at his secretary. The man breathed a sigh of relief, slumping in his chair as a low moan escaped his throat. Sam walked over to him, circling around the desk to stand behind him as he saw Dean tense with the close proximity. He leaned down, one hand braced on the desk as the other came down to run a finger over the spot where the toy disappeared into the man’s body, teasing the sensitive stretched skin.

“You’ve been very good today, Dean.” His voice was low, silken praise and a dark promise lurking in the words. “Why don’t you reward yourself a little bit?” His mouth was close to the man’s ear as his voice dropped to nearly a growl. “Fuck yourself on that thick cock. Ride it hard for me.” At the secretary’s whimper, he smiled. “But if you come before I tell you, I’ll bend you over this desk and spank your ass raw.”

He went back to his own desk and sat back, settling in to enjoy the show as Dean did as he was told, lifting himself up, the wide cock dragging slowly out of him, reappearing inch by inch until only the head was left inside, nudging at the inside of his rim. With a low groan Dean dropped back down, his hips rolling as he took the toy deep inside once more, a groan escaping him at the pleasure that went soaring through him, arching through every nerve from his toes to his fingers.

He set up a steady pace, hands braced on the chair’s armrests as he fucked himself. Sam watched, a swell of pleasure racing through him at the sight. He didn’t look away as he undid his belt and unbuttoned his pants, lowering the zipper to slide his hand into his boxer briefs. He wrapped his fingers around his aching cock, stroking in tandem with Dean’s movements as he watched the fake dick slide in and out of the secretary’s pretty, stretched hole.

Dean’s moans were becoming louder despite his attempts to hold them in, the sound spurring Sam on as he stroked himself, twisting slightly at the head with each pass, imagining himself buried deep inside of Dean, fucking him hard. He felt his orgasm creeping up on him and he grabbed at the tissues on his desk with his free hand, a choked cry escaping him when he spilled into them moments later.

He took a second to gather himself, his mind blanking from the pleasure coursing through him as he watched his secretary continue to ride the toy. Once his breathing slowed and he had zipped and buckled back up, he stood, once more circling around to stand behind Dean.

“So fucking hot, all stretched out and needy,” he muttered, his hand coming around to lightly graze his fingertips along the underside of Dean’s dripping cock.

Dean let out a strangled moan, grinding against the toy as his hips sought out more of Sam’s hand on his throbbing member. “Please, sir…I-I need…”

“I know what you need.” Sam’s voice was carefully-measured. He had no intention of relenting, of letting Dean come. “Are you close?”

Dean nodded. “So fucking close.” His voice was a needy plea.

“Sit still.” Though Sam’s voice didn’t get any louder, the command was unmistakeable.

Dean stilled his movements with great effort, everything in him wanting to buck his hips, bring himself to climax. A spanking might be worth it… His gaze fell on Sam’s large hand where it was braced on the desk. Maybe not.

Sam chuckled and went to unlock the door, pleasantly sated as he heard the frustrated groan that issued from the other man.

By the end of the day, Dean was a wreck. He wasn’t sure how he had managed to make it through without either coming or quitting and storming out to jerk off in his car. He felt like the slightest touch would bring him off, and when Sam locked the door for the final time that day he fell forward, resting his head on his arms, a whimper escaping his throat as the dildo shifted inside of him, rubbing against his swollen rim and over-sensitive nerves.

Sam settled back in his chair, taking a moment to appreciate the man’s desperation. He was in better shape, of course, but watching Dean for the rest of the day had kept him hard, and now that the work day was over he was trying to decide what he wanted to do first. A slow grin spread across his face when he finally came to a conclusion.

“Come over here.” The command was quiet, but in the empty office it carried easily. He heard Dean his as he stood, the dildo sliding out of him and leaving him achingly empty. He stepped out of his shoes and pants rather than pulling them up and came to stand in front of Sam, his angry red cock bobbing with each movement. “On your knees.” He smiled when the man obeyed and leaned back with his hands on the armrests of his chair. “Suck me.”

Dean bit his lip as he undid Sam’s belt and opened his pants, tugging at the waistband as the lawyer lifted his hips slightly to allow him to slide them down. And then Dean was leaning forward, running his tongue from the base to tip before taking the wide cock in his mouth, lips stretched perfectly as he lowered his head, sucking hard.

Sam groaned. God, the man was good at this. He was going to have to get him on his knees under his desk one day, make him suck him off nice and slow while Sam talked to a client, the possibility of being discovered chasing the wet, hot pleasure until he spilled into Dean’s mouth. He’d have to remember to tell the man beforehand to swallow it all down, not waste a drop.

The idea coupled with reality shoved Sam hard towards climax and he pulled the man off of him, the wet heat of his mouth leaving his cock just in time as he felt himself hanging precariously close to the edge. He took a second to catch his breath, and then he stood, pulling Dean up and turning him before bending him over his desk. He gazed at the man’s gaping hole, the muscles twitching in anticipation as Sam’s fingers came up to rub at the rim, dipping inside just enough to tease.

“What do you want, Dean?” Sam’s voice was low and smooth as Dean pushed back into his touch, trying to push the digits further inside of him. Sam could feel that the hot passage was still slick from the earlier preparation and the thick toy.

“Anything.” The secretary’s voice was wrecked when he answered, raspy and needy. “Fuck me, sir… Please, I need it so bad, need to come…” He let out a low whine. “Fuck, please, sir.”

Sam lined his cock up, pausing for a moment to enjoy the way his secretary pushed back eagerly, another needy moan tearing from his throat. “God, such a good little slut. You need it bad, don’t you? So fucking hungry for my cock.”

Dean sounded near tears now. “Please, sir, fuck me hard! Need it so bad; need to come.”

Sam finally pushed in, gritting his teeth as the tight heat surrounded him. He set up a hard pace, his hands gripping Dean’s hips hard enough to bruise as he fucked into him, driving them both closer to the edge with each thrust. “Touch yourself,” he ground the words out, and Dean let out a grateful moan as he gripped his own cock, stroking in time with the hard thrusts.

He came hard, the orgasm that had been building up all day ripping through his entire body as he screamed out his release, his cock pulsing and his release shooting onto the floor in thick spurts. Sam wasn’t far behind him, slamming in as deep as he could as his cock twitched, filling his secretary with his hot release as his muscles milked his cock.

They were still for a moment as they both came down from their pleasure-induced highs, breathing heavily. Finally Sam pulled out, looking down to see his cum start to seep out of the abused hole. He smirked, righting his clothes, and then headed for the door, leaving the man a fucked-out mess on his desk.

“See you tomorrow, Dean.”