There were some days Stiles really hated his job as a prison guard. The inmates were rambunctious, if not overtly violent, the food sucked, because even if he brought it from home the dreary atmosphere just sucked the enjoyment out of it, and the staff, save for a few people like his father, the warden, or Jordan and Chris, his fellow guards in this block, were complete sadistic assholes. He’d already reported at least two people to the warden, which they called tattling to daddy, which had not earned him any good will, save for Jordan who thought it was a noble idea.
Of course today was one of the days he kind of loved his job, which he knew made him a sick, sick person. It was prisoner intake day and, seeing as Jordan was out sick and there had been a ruckus in the block earlier, Stiles was left to do it alone, since there was only one guy coming in.
When he met Officers Boyd and Reyes at the door, he got a good look at the man and he had to school his reaction. The guy, early thirties and built like a brick shithouse had stubble that went on for days and bright eyes that made Stiles want to swim through them. He was surly too, which was a weird thing for Stiles to like, but he was surrounded by surly men all day, it only made sense he’d end up sexualizing it. Or at least, that’s what he’d told himself. Leading him back to another room, he began the procedure for the mandatory strip search.
He had the man, Derek Hale he read on the sheet, disrobe as he watched. He kept a critical eye, but he couldn’t help but have his mind wander a bit as the man peeled each article of clothing off, strong shoulders giving way to a furry chest and perfectly toned abs. Stiles stole a glance at the man’s cock, nicely shaped and hanging between his legs enticingly, before moving around behind him and finding the most perfect ass he’d ever seen. It was nice and round, with just the right amount of meat that he knew he could just grab hold and ride for hours. It was lightly furred with most focused in his crack, rather than his mostly smooth cheeks.
Walking back around, Stiles went through the motions of the search, hoping his hard cock wasn’t visible in these stupidly tight pants the guards were made to wear. Once almost everything was done, he moved to the final task. “I’m going to need you to bend over and spread your cheeks,” he told the new inmate, told Derek.
Derek’s face soured even more so, but he did as instructed. Stiles inspected him, shining the light. He didn’t find anything so he stood back up.
Then he had an idea, and asked Derek to end over again. Taking one gloved hand, he ran his finger through the soft fuzz of Derek’s crack, fingertip skimming over his rim lightly. “I think I see something, I’m going to have to do a full cavity search,” he told him, receiving a distressed noise from Derek. “Move to the table over there and plant your feet wide, hands on the table,” he told him as he ushered Derek forward.
“I, I don’t have anything in there, I swear,” Derek told him, voice a bit less gruff than before. “You don’t need to do this, really officer.”
“I’m sorry Mr. hale, but once I’ve seen something I’m bound by law to check and be certain,” Stiles intones, reaching over and grabbing a bottle of lotion they had lying on the desk. He uses some on his finger, getting it a bit slick before pressing back at Derek’s entrance. “Just try to relax, this should only take a minute,” he said, pressing the barest tip of his gloved finger inside the man’s heat.
Derek’s body tensed at his intrusion, and he placed his other hand on his hip, stroking gently to try to help him relax. “It’s alright, this won’t hurt,” he told Derek; pressing a bit more inside him, first knuckle passing his rim. Now that he had it inside, he twisted it and turned it, finding that Derek shuddered at the movement. He repeated it a few times, earning the same reaction from the male.
“Mr. hale, are you… Are you deriving pleasure from this invasive exam?” he asked, voice all seriousness.
“I… No… No, sir,” Derek breathed, but his breathes were coming heavier now, and when Stiles looked through the gap in his meaty thighs, he could see his cock slowly filling with blood.
“Good, we wouldn’t’ want things to get awkward, now would we,” Stiles said, smirking as he pressed his finger in more. He pulled it out, then pressed back in again, over and over, watching as Derek slowly shifted his stance, legs spreading wider unconsciously to give him more leverage, to let his finger go in deeper. He rooted around for a bit, turning his finger to and fro, speeding up a bit as he fucked him one it, until Derek’s pressed into it, arching his back to take more.
“Mr. Hale, I haven’t yet found any contraband, but I’m still not convinced. I think I am going to need to use two fingers this time,” he tells him, pulling out to coat his other finger in lotion before pressing both at his entrance.
“O-ok,” Derek stutters, practically sighing as the fingers breech him again.
Stiles scissors his fingers apart, watching Derek clench around him, notices how his legs are practically trembling now. Pressing in deeper, he gets the fingers all the way in before pulling out, fucking back into him with smooth glides of his wrist. Punched sobs fall from Derek’s mouth as he moves, and Stiles looks between his legs where the man’s cock drips steadily, pointed towards the floor thanks to its proximity to the table.
“P-please,” Derek whispers, and Stiles is pretty sure he didn’t realize he said it out loud.
As Stiles alternates fucking in and out of his hole and scissoring it open, Derek drops his head, bowing a tad more. He can hear the man’s fingernails scrape at the hard plastic of the table, trying to claw at it to stay upright. “Ah hah! I knew I saw something in there,” Stiles gloats, fingers pressing in more. Before Derek has time to say anything, Stiles presses two fingers against his prostate, licking his lips as he hears a wrecked sob wrench itself from Derek’s lungs as he shakes.
“I knew you were hiding this from me, weren’t you?” Stiles asks, standing now as he rubs at the pleasure spot, looking around to see Derek’s cock smacking into the underside of the table, flushed red and drooling pre-ejaculate like crazy. “What do you have to say for yourself Mr. hale?”
“I… I-I-I’m s-sorry,” he gasps, whole body shaking with pleasure, hole clenching tight around Stiles’ fingers.
“As you should be. We run a tight ship a round here, we can’t afford fresh meat bringing in any contraband. I’m going to have to test this out, make sure it won’t cause any danger to you or anyone else,” he says, rubbing small, hard circles into his spot. Stiles’ cock is so hard in his pants he feels he might burst, moving faster and adding more pressure as he feels his own release building.
Derek pants weakly, chest heaving as his cock leaks like a faucet. He pushes back, getting the fingers as deep as they will go, his own balls drawing up.
“Come on, give it to me,” Stiles grits out, hand like a blur as it moves in and out of Derek’s stretched hole.
“Please, p-please, let me. Let me c-c-um!” Derek gasps, before Stiles presses hard one last time and Derek shoots his load all over the floor. As Stiles feels the pressure on his fingers, he shoots in his pants as well, watching Derek slump over the table, spent. “There, ready for general population,” he says, smiling and taking off his gloves.
“Are we finished,” a gruff voice asks, snapping Stiles from his dream. His knees hurt, so he isn’t sure how long he was kneeling, staring at Derek’s asshole.
“Uh, yeah, yeah,” Stiles squawks, standing up and readjusting himself to try to hide his massive erection. “Nothing suspicious here.”
“I could have told you that, I’m not an idiot,” Derek grits out, standing now, covering himself with his hands. His eyes trail down to Stiles’ groin and he looks up with an odd expression, but says nothing.
“Flushing a bit, Stiles moves to grab the assigned prison clothing for Derek and hands it to him. “These are yours for the duration of your stay here. We collect laundry every other day, so try not to get them too dirty,” he tells him, surreptitiously watching Derek get dressed, which while not as fun as it was in reverse, is likely the last glimpse of his body he’ll get.
Once Derek is dressed he walks him down the hallway, noting Chris at the end of it near the prison bars. “Welcome to Beacon Hills Correctional facility Derek Hale,” he tells him, watching Chris open the gate. As the two men walk off, he notices Chris is walking a bit funny, almost a limp, but he writes it off to old age, Chris is practically a dinosaur compared to him and Jordan.
Walking back, Stiles recalls his little dream during the strip search. He’s a shamed of how much he liked it, even though in his heart he knows he’d never truly act on those impulses. Still, it was hot enough that he makes a stop at the first bathroom, rubbing one out in under a minute, cumming to the image of his fingers buried deep in the new inmate’s ass. “I’m so gross,” he says, wiping himself off before zipping up and heading back to work.