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The Inspector Makes Terrible Decisions

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To say the Midnight Crew were dangerous people would be an understatement. They were literally made up of a sadistic narcissist who enjoyed kidnapping and trying out different forms of torture, a behemoth cannibal who could rip people in half, and a moronic pyromaniac, all led by a man who expressed himself via stabbing and honestly believed that to be a healthy mode of communication. Dangerous people, indeed, as well as completely psychotic. The Pickle Inspector had done well to avoid them thus far, steering clear of their territory, covering his tracks during investigations, not asking questions when Sleuth came to the office with just as many stab wounds on his body as he had bite marks on his neck. But the Midnight Crew ran the city, and you can only avoid such prominent figures for so long.

They'd gotten a tip of the Crews next move. Nothing complex, a simple bank robbery, probably just to have something to do if not for the cash that they didn't really need (what with owning the city and all). But still, it was a robbery, and it was the first time Team Sleuth had a chance to head them off, take them by surprise. Of course they couldn't pass it up. Sleuth and Dick were rearing to go, hats on, candy stocked, but the Inspector felt only dread. He'd finally be placed on the Crews radar, and it could only end in blood. Most likely his own. But still, he went, because he was loyal to his friends and it was the right thing to do. It just wasn't the smart thing.

The Crew were already there by time they arrived, which was just fine, because they still had the element of surprise- Or would have, if Sleuth and Dick had opted for literally any strategy other than charging in screaming as they had. Sleuth and Slick immediately clashed in a knife fight, despite Sleuth having his keys with him, and Dick all but threw himself at Boxcars. How either of them were still alive was truly a marvel, in the Inspectors ever humble opinion. Deuce seemed thoroughly amused and distracted by the scuffles around him, watching closely, completely enraptured. He was no threat. The Inspector could remain undetected and-

“This is quite brazen, even by your teams standards.” The voice was smooth, flawless, and cold enough to freeze PI in his place. He'd forgotten about Droog.

“I- I- Th-this wasn't m-m-my idea.” He explained, forcing himself to move, to turn to face where Droog was approaching from the side. He didn't even have his cuestick out, or a gun. Perhaps he just didn't consider the Inspector worth a weapon. The mobster kept stepping forward, tilting his head, eyes narrowed, intent on backing the Inspector out of the room and into the hallway.

“Of course not. You're too cowardly. Or... perhaps too prudent.” The latter was the truth of the matter, but as he all but shook in his spot, rooted to the ground, it felt an awful lot like the former.

“I... It's i-i-idiotic, and d-dangerous to challenge the C-Crew directly. Th-there were smarter options.” He admitted, and he didn't want to give ground, to step back, but did so anyway as Droog pressed on.

“Indeed there were.” And there was the cuestick. “Much smarter options. Less painful options. You chose poorly.” He'd probably sound scolding, if he didn't sound so bored. The Inspector wrung his hands, breathing fast, looking around for some way out. Droog had corralled him into an isolated area, no one there to save him. The mobster prepared to swing, only debating if he should go for the ribs or directly for the head. But the Inspector's attention immediately snapped back to him as his arms drew back to swing, and quicker than he could follow a shaking hand dove into his coat and drew his gun.

Droog had not been expecting that. He froze, as did the Inspector, both analyzing the situation.

“P-please don't. I- I r-really don't want to, but I w-w-will shoot.” He swallowed hard, taking a deep breath. All of him was shaking, but his hands were stock-still. “I-I don't want to ruin s-such a nice suit.” He began to chew at his lip nervously, as Droog did something far scarier than draw a weapon. He smiled. His smile was like the rest of him, sharp, dangerous, and completely terrifying. The Inspector felt his blood chill as Droog lowered his weapon, his face returning to its neutral state after that brief break in expression.

He was thinking. That was obvious. Considering the Inspector closely, sizing him up, analyzing him, and the taller man had the distinct feeling of being laid out and dissected. That gun never moved, and neither did they, until a bang from the other room shook the Inspectors attention, and Droog took the opportunity to stride forward. By time the Inspector realized he was approaching, he was being slammed into a wall, his gun rendered useless, facing the ceiling as Droog pinned his arm to the wall by his wrist. The Inspector didn't dare to so much as breathe, blue eyes wide and frightened, meeting cold steel when they looked to Droog's.

Speaking of cold steel.

His breath hitched before starting up again when he realized where Droog's other hand was, holding his own gun, pressed just under the Inspectors chin.

“You let your guard down.” The mobster pointed out, needlessly, tone still bland but not nearly as bored as before. He did not allow the Inspector to reply, realizing he most likely could not whilst under such stress. “You're smart, Inspector, I'll give you that. Don't think I've overlooked the way you dig up information on us. You're good at covering your tracks, better than most, but I don't miss anything.” The gun was dragged down, cold along the pale skin of his throat, and Droog's eyes followed its path. It was entirely possible that the shiver that went through the Inspector was not completely fear-based.

“You're not a physically strong man, but you are not a coward. Anxious, definitely, but you can do what you need to in a pinch, can't you.” It was not a question. Droog's demeanour suggested that he didn't often phrase things as questions. The Inspector did not answer, simply observing as Droog's gaze snapped from the gun, back to the face of the man he had pinned. He leaned in, leaving only an inch between himself and the detective, watching his reactions, listening to his breathing. The Inspector thought he was more or less keeping his cool, all things considered, but when Droog's leg pressed between both of his own, he couldn't help but whimper. That was not something he had prepared for, not something he had considered, and the way Droog's lips twitched into a mockery of his previous smile told him that he had meant precisely what he had done.

“To continue with my previous observations...” Amusement laced his tone now. “You are not nearly as terrified as a man being held at gunpoint should be, pinned against the wall by a notorious criminal. Why is that, Inspector? You know I like hurting people.” Both men's eyes dropped back down to the gun, being brought back up, tracing along the side of the Inspectors face to rest against his temple. “You know I enjoy it, and I would enjoy hurting you just as much. So why aren't you scared?” That wasn't entirely true. He was scared, of course. Just not nearly as much as he logically should have been. Droog leaned in, until he was right beside the Inspector's ear, his lips moving against his skin as he spoke.

“Because you'd enjoy it too.”

Pickle Inspector was unsure if it was the words or the teeth that bit into his ear after they were said that made him gasp, a sharp intake of breath that melted into a moan as that leg pressed against him. He still had a hand free. He knew it, Droog wouldn't have overlooked it, it was intentional. He wanted to see what the Inspector would do. Sleuth would want him to put up a fight. Sleuth would want him to struggle and deny and make a scene. But somehow, that just didn't seem all that appealing to him. It would certainly be the smart thing to do. Droog was a dangerous sadist and certainly had something horrible planned for the gumshoe, but... But the Inspector just found that unbelievably exciting. Finally, he managed a word. A single word.

“Y-yes.” That was it, followed by a hard swallow, a shaky breath, trying hard not to grind down on Droog's leg like some horny teenager. He felt a tongue lap at the blood dripping from the bite on his ear, and couldn't help but squirm where he was pinned. Droog was making him wait, taking his sweet time before pulling back to look at him again. His expression was unreadable, something between interest, curiosity, and everything else that the Inspector simply could not decipher.

“When we all inevitably part ways tonight, do not go back home or back to your office. Come to my place.” He spoke low, quiet, quick. This would not be something for their respective teams to know about.

“You have a- a lot of places.” He scrawnier man pointed out, only earning a scoff for his troubles.

“Come now, Inspector, let's not play games here. You make a note to know where each of us are staying at any given point in time.” Not an implication the Inspector could deny, but one that made him blush nonetheless.

An increase in volume from the other room suggested the nights scuffle was coming to an end. The Inspector was treated to a single, hard kiss before he was left alone to slide down the wall, panting, hard, and wondering exactly what the hell had just happened.


Pickle Inspector showed up at Droogs place afterwards, just as he'd been instructed to do. This was Diamonds Droog, after all, not some sort of ditchable prom date to be stood up if he lost the nerve. He was sure whatever Droog did to him that night would be nothing compared to what would have happened if he'd neglected to show up.

He wasn't sure if the way his hand shook as he knocked on the door was nerves or fear or excitement, but he felt perhaps it was a combination of all three. He had no idea what he was doing, no precedent for the situation. All of his... intimate encounters had been sweet, loving nights with Broad, and he was sure that this would be nothing of the sort. That uncertainty was what left him fidgeting and standing stock-still once brought inside. He went only where Droog led him, did as he said, and the mobster didn't seem very inclined to ease his nerves. Coat, hat, and shoes were left at the door, and it seemed everything else would soon follow, as Droog led him to his bedroom and undressed him. Or, began to, then paused.

“I'm aware you can barely manage to dress yourself, but I don't suppose you'd be able to manage undressing yourself?” He raised an eyebrow in question, and his guest flushed bright red as he caught onto the implication. Droog was asking him to strip for him. That... That he could do. He could never be confident or sexy about it, but he could go through the motions. He nodded stiffly, and Droog stood there, studying him for another long moment before stepping away and loosening his own tie as he sat back on the bed. The Inspector took a deep breath, trying not to think of the hard grey eyes observing him as he loosened his own poorly done tie. He was about to slide it off, when he was interrupted.

“Keep the tie. We'll need it later.” Droogs tone was off-handed and casual, but PI couldn't help the small noise he made in response, the way his breath caught. He began to unbutton his shirt, slowed by his shaking hands but managing all the same, sliding the collar underneath the loosened tie and the shirt from his shoulders. That, he was allowed to let drop, and he tried not to think too much about how each of his ribs were visible, about how sickly shadows would be cast on too-pale skin. He continued not to think about it as he continued to undress, only looking back up at Droog once he was completely naked. The mobsters expression hadn't changed at all. He stood, tall, but still shorter than the Inspector, and circled around him, pulling his arms back and binding them with the tie. The Inspector tried not to think about other situations where Droog would be tying someone up. There were many things about this he was avoiding thinking about.

“How's that?” The mobster still sounded so sure, so calm, as he tested the bindings. “Not too tight?”

“I-it's fff-f-fine.” Pickle Inspector was just beginning to be appreciative, though surprised that Droog had checked, before he was shoved down to his knees.

“Good.” Droog brought himself back around into the Inspector's line of sight, undoing his own pants and pulling himself out. He was already hard, the Inspector noted with some astonishment. From watching this pathetic scrap of a man undress? Or perhaps simply from having a member of Team Sleuth willingly tied up, naked, and on his knees before him. He began to wonder which was more likely, when a familiar cold feeling pressed against his skin. The same gun from before, sending a shiver through his bones, catching a whine in his throat. He looked from it to Droog nervously, trying to convey a wordless question. Droog was utterly unmoved, the hand free of the gun gripping onto PI's hair.

“Open your mouth, Inspector.” He did so, of his own volition and not because of the gun pressed to his- His tongue. He had expected something else, and it was evident that Droog had planned it that way. He tried not to panic as the gun was pressed into his mouth, looking up at Droog for something, anything. “I wouldn't bring you into my home to kill you, Inspector. It'd stain the carpets.” As much comfort as he'd get from a man like Droog. But then, if he wasn't planning on blowing the Inspectors brains out, then why did he-

Oh. Right. Of course.

The Inspector got to work, sucking on the gun eagerly, running his tongue along the quickly-warming metal. He raised his eyes to look to Droog again, and while his expression was still completely neutral, his breathing had quickened. Now was the Inspectors time to observe, and he watched the mobster carefully as he moaned around the gun. The hand in his hair tightened, Droog's breath hitched, and then suddenly he was pulled back, the gun removed and replaced with what he had originally expected. He took in as much of the mobster as he could manage without choking or gagging, sucking hard and being very careful of his teeth. He was sure he was overthinking it somehow, but Droog seemed to be enjoying it well enough, hips twitching forward as it he were restraining himself from fucking the Inspectors mouth. In fact, the thought of Droog doing just that made him groan around the cock in his mouth, and he almost missed the small sound Droog made in response.

Eventually, he was pulled back again, and dragged up off the floor. Droog really did seem to enjoy manhandling him, pushing him back onto the bed. The Inspector watched eagerly as Droog placed the gun aside and removed his own clothes. Where the Prospitian was all skin and bones, Droog was scars and muscle, dark skin littered with evidence of a darker past, a sentence which would be constrained to use in terrible romance novels were it not so accurate. He climbed on top of the Inspector, who found himself wishing he could hold onto him. The restraints were definitely exciting to him, but he was used to being able to hold his partner close. Though, he hadn't been expecting what he was used to, and it was definitely not what he was getting. The Inspector lost himself in this train of thought, so thoroughly that he did not even notice Droog reaching to a bedside table, hooking his legs over his shoulders, or actually applying the lube he'd been reaching for before, until a finger was pressing inside of him. That was certainly something to come back to. He gasped at the sensation, squirming against it, causing Droog to set a hand on his waist to steady him.

One finger soon became two, scissoring and stretching, which was uncomfortable but something about it just made him want more. Once three fingers were able to thrust in and out of him smoothly, they were removed altogether. The Insepector waited for them to be replaced, but was met with nothing at all. He pried his eyes open, not sure when he closed them, and found Droog just looking at him. They stayed there like that for a moment, until the Inspector took a deep breath and made himself speak.


“Hm?” Such an eloquent response. The Inspector began to worry he'd done something wrong.

“Are... are you g-going to- um...” Sweet GPI, he couldn't even say it.

“Am I going to what. Is there something you want, Inspector.” He said it so flatly, it hardly sounded like a question at all. As always, Droogs intent was obvious. He wanted the Inspector to beg. It was only then that the taller man truly wondered what exactly it was that he'd gotten himself into.

“I- I-” He swallowed hard, trying not to let his breathing get out of hand. “I-I should v-v-v-very much like it if- if perhaps you- you could-” He couldn't do this. He couldn't. He had a hard enough time speaking as it was, there was no way. “If you c-c-c-could-” He tried again, breaking off in a frustrated whine. He tilted his head back, to look away from those piercing grey eyes, but Droogs hand moved from his waist to take hold of his jaw, turn his face back towards him. He leaned in close, like earlier, when he'd been pinned against the wall.

“If I could what, Inspector?” He all but hissed, and wide blue eyes just stared back at him as PI spoke very, very quietly.

“F-fuck me?” He tried, wincing at how vulgar it was. But Droog seemed pleased, backing off. The Inspector thought he'd get what he wanted, but was worried perhaps Droog would try to make him beg. Thankfully, the mobster simply pressed his length inside as the Inspector gasped, stopped from tilting his head back by the hand still holding him in place. Droog watched the Inspectors expression carefully as he slid inside him completely, pausing for just a moment before pulling nearly all the way out and slamming back in. The man beneath him cried out, and continued to do so as Droog set his pace, quick and harsh, and while hearing the Inspector cry out his name was definitely not an unpleasant experience, he was tempted to do something about it.

The hand holding onto the scrawny mans jaw slid down to his throat. He was so small compared to Droog, despite his height. It only took one hand to wrap around his neck and squeeze, effectively cutting off all air and noise aside from a quiet squeak. The Inspectors eyes were wide, frenzied, but like with the gun, once the initial shock dissipated there was a certain thrill that settled in, enhanced the whole thing. Droog, being the sadistic killer that he was, knew exactly how much time it took to choke someone out. He watched carefully, paying attention, and just as the Inspector danced on that edge, he took his hand away. He watched as the bony mans chest expanded with a desperate breath, as he gasped and coughed and moaned, pressing into Droog's thrusts before actually begging for more without any prompting.

“O-oh G-g-g-ah! P-please- p-please do it ag- again?” Droog didn't need much more incentive, squeezing the air from his partner until the other mans lungs were screaming, before allowing him to take a breath again. The way he squeezed around him when he was allowed to breathe was exquisite, and both of them were quickly reaching the end. Rather than choke him off again, Droog bowed his head, those threateningly sharp teeth of his biting deep into the flesh of the Inspectors shoulder. That was it for the Inspector. A last cry ripped itself out of his abused throat as he came, and Droog wasn't far behind as the Inspector squeezed around him. The broader man, however, made no sound beyond a low groan.

He pulled out and rolled off of the Inspector, and was surprisingly gentle in turning the other man just enough to untie his wrists, throwing the tie aside and rubbing feeling back into his hands. The Inspector had thought that after this encounter, Droog would throw him out or threaten him into silence. He was surprised to find himself pulled into the mobsters arms. Droog was much warmer than one would expect from such a cold man, but the Inspector pressed against him happily, smiling softly and already drifting off. He'd had quite the tiring evening, after all.