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He had warned Rouge this was a bad plan from the start, going as far as to admit this was something he simply could not pull off, not in a hundred years. The bat was never deterred though, as she shoved yet another skirt in Shadow’s direction, another thing he had his complaints about.
“Do I absolutely need to wear this?” He asked with a grimace, checking in the mirror how awful the pink fabric stood out against his black fur. Too flashy.
“These little touches are important Shadow, I swear you won’t catch any eyes. Not with you scowling like that all the time anyways.”
Shadow threw the skirt in her face.
If anything, their positions should’ve been switched; even if Shadow wasn’t the best at stealth, he had a good set of abilities that would make up for that, but Rouge had told him the situation was sensitive enough they could not risk getting caught. He hated that she was right.
Despite that, Shadow couldn’t see how getting him to do this made things any easier.
Rouge assured him he wouldn’t need to talk to anyone, he just had to stick to his corner and not lose sight of their target. Some middle aged entrepreneur no one would bat an eye at, except the police had caught on his regular meetings with no one other than Doctor Eggman, and quickly tied him to the mess of corruption inside the city hall that had allowed Eggman to build yet another electric plant with less than clear purpose. So, as it could mean a global threat, GUN got involved.
They needed as many details on those meeting as they could get, and this man was the most direct way of getting them. So they already had his home and work address, places he frequented, stores he shopped in, everything mapped so nothing escaped them. Whatever deal he made with Eggman had to be making him dirty rich, as he moved into a literal mansion last month, protected by the best security money could buy. The guy was definitely paranoid.
So to make sure things went smoothly, Rouge would infiltrate the home while Shadow tailed him and updated Rouge on anything suspicious. They knew he would be visiting his usual night club, a barely legal place where human men could have fun with mobian partners, so Shadow needed to play the part.
He ended up agreeing to the makeup and the skirt, but refused to put on any more clothing and fought tooth and nail for his rocket shoes. He didn’t even need to say it out loud, but he’d feel extremely vulnerable without them, even if the job wasn’t dangerous, just way out of his comfort zone.
In the end he doesn’t know how she made him give in, probably because even he could see how they’d look extremely out of place, but he begrudgingly handed them over with the most dejected look Rouge had ever seen in his face.
“Oh, darling, it’s only going to be for a little while, I’m sure you won’t need them,” she cooed and petted his ear, but he just scoffed, not wanting any more humiliation for tonight. A pair of Rouge’s more modest low heel shoes completed the outfit, Shadow grumbling how he could not run in them, but he was ignored from that point on as the bat continued to brush him and groom him into the perfect undercover spy.
He arrived at the nightclub shortly after the target, keeping his head low and trying to swallow the feeling of anxiety and burning shame that never left him. He only needed to keep an eye on one man and not talk to anyone else, he’d be fine.
He sat down two booths away, ensuring he had clear view of the target at all times. The man was average height for a human, nothing about him made him stand out, really. Plain shirt and dress pants, Shadow didn’t know enough about clothes to determine if any of it was expensive, the jacket he discarded by the edge of the seat did look high quality, and he could only assume the flashy watch in his wrist must cost a fortune, probably bought with Eggman’s dirty money. Other than that? Average guy.
Shadow ordered a drink only for appearances, and every time some human man tried to sit with him or even looked at him with the intention of approaching, he looked at them with enough disdain to make them disappear instantly. He was glad the makeup hadn’t taken that much bite out of him.
“Everything alright over there?” Rouge’s voice came from the intercom, making his ear twitch. He looked around before replying, pretending to be too interested in stirring his drink.
“Yes, nothing new. You?” He pursed his lips when he heard Rouge sigh. A setback, then.
“I knew I wasn’t making it through the front door, but the amount of cameras here is absurd, I had to fly over to the roof and reroute from here. Will you be okay for some extra minutes?”
“You don’t need to worry about me,” he sighed, but he was a little glad that she did, just this once. Made him feel a little less silly about the anxiety the situation caused him.
“Alright then, tell me if anything comes up, ‘k?” Shadow just hummed in response, not sure if the hidden mic was able to catch it, but she’d understand.
When he turned his gaze back on the target, his heart almost catches in his throat when he found him staring right back at him, a little smile on his lips when their eyes met. Shadow swallowed his heart back down and scrambled his brain for what to do, when the man stood up and started walking in his direction. Okay, problem, problem, problem.
He was looking like a deer in the headlights, ears pinned back, looking up at the man in front of him and trying to figure out if he had somehow slipped up, if he’d listened to his conversation, had he blown off his cover already? What would the best course of action be then? Should he fight or flight? God they hadn’t planned for this-
“Uh-”
“Are you waiting for someone?” The man asked, his smile kind despite having inadvertently filled Shadow with terror. The little hedgehog blinked a few times before shaking his head, regaining his composure to the best of his ability. That made the man give him a funny look, “Really? Because you’ve been turning down every man that’s come talk to you, I thought you might be busy.”
“I-I mean,” He was thrown for the loop again at the confession he was also being watched the entire time. He had to salvage this somehow, “I was, at first, but I don’t think they’ll show up now.”
The human made a sound of sympathy, moving to sit down in front of him which made Shadow bristle. Was he going to stay? He shouldn’t be talking to him at all! Oh he hated improvising, but he would if needed.
“So he stood you up, huh? Shame, he probably doesn’t know what he’s missing.” The way he was looking at him now made his skin crawl, but then he noticed what the other was placing down on the floor under the table. A briefcase. Shadow had noticed it when he first came in, thinking it would be good to get a hold of it, but dismissed the thought as that wasn’t part of the plan. It was withing reach...
“Your name is Robert, right?” He effectively caught his attention, knowing he needed a way to reel him in. Before the other could question him, he added, “You come here quite a lot.”
“I wouldn’t say a lot…” His smile was a bit hesitant now, but he didn’t seem ready to leave, “And yet I don’t think I’ve ever seen you.”
“Well, I’ve seen you,” Shadow said, pretty sure he was doing a lousy job if he was trying to be flirty, but whatever, he just needed some time, “It’s difficult not to notice.” He tried for a sweet smile that made the other relax almost instantly. Huh, not such a lousy job then.
“Oh? And what is it that makes me so hard to miss?”
Shadow opened his mouth to reply and then closed it again, drawing a blank. He’d really just thought of the man as unremarkable, but even now thinking of what to compliment him on made him embarrassed. He’d never spared words like that to anyone, most praises he gave based more on skill than looks. Having to willingly admit he found someone attractive was almost as humiliating as the small skirt and shoes.
“I uh, I just think you’re… handsome.” Ah shit.
If he was this flustered by saying those words, he was doing terrible in the role he was supposed to be playing. However, Robert seemed more than satisfied with the compliment, and Shadow had to hold himself back from flinching when a cold hand grazed over his burning cheek.
“And I think you’re stunning.” There was no way his face was getting redder, but his gut did twist in an unpleasant way. Or at least he thought it was unpleasant. He kicked his leg slightly just to bump against the briefcase between Robert’s legs. He had to play along.
“Thank you,” he smiled, leaning into the touch briefly before turning his attention back to his drink, taking a sip. Now the man was full on caressing his face, stroking his cheek with his thumb, moving up to rub circles behind his ear. Shadow swallowed and closed his legs, it was making him feel weird.
“In that case, since you’re not busy right now…” Robert took his hand over the table, squeezing gently, “we should move somewhere more private, don’t you think?”
Shadow didn’t let anything show on his face. He had a pretty solid poker face, even in a situation as bizarre as this, but the prospect of following this man to the bedroom was making him a little dizzy. He didn’t do well in social interactions, this was taking it ten steps too far.
He wondered what Rouge would do in his place. It was easy for her to wrap people in her own game and get them to do what she wanted, never giving more than absolutely necessary while taking everything to herself. She never did any sexual favors, she was adamant about it, the way she presented herself was for her own liking but also highly strategic. Rouge would probably laugh at him if she knew he let this man touch him just because he couldn’t hold a decent conversation.
And yet he was so close, and this weird panicky feeling in his chest wasn’t letting him think about any other way of getting what he needed and running with it. Plus, Robert was meant to stay here for another hour at least, if Shadow displeased him enough he decided to go home early, Rouge would have to cut her own mission short. Robbing him point blank would get them the same result.
Besides, he could get even more information like this.
So he squeezed Robert’s hand back and stood up with a smile that was probably more polite than provocative, but it was serviceable.
“Show me where you’d like to go, then.”
The man’s eyes seemed to shine as he started pulling Shadow away from the dining area. He was probably feeling very proud of himself, the fact he had managed to pull off the pretty guy who scared off everyone else with a cold glare had to be stroking his ego something fierce. It was a good thing, Shadow needed him pliable.
Despite the potential danger of his situation, he couldn’t help but be glad Robert had not just grabbed him and started making out with him right there, as many other humans they passed by were doing with their mobian partners. Shadow wondered if all of those mobians worked here.
“That looks like an expensive watch,” he said, initiating a conversation would be the best way of compiling any important info he could get. The other hummed, looking at Shadow with a strange smirk.
“Do you like it? You know, I could get you something nice like this…”
It seemed like Shadow didn’t need to try that hard at all, Robert just loved talking about himself. Only that comment got him talking about a myriad of details about his personal life, his job and expensive belongings; many of these things Shadow already knew about. He had kids, but he wasn’t married and none of them lived with him. His business had only recently took off and only promised to keep growing —Shadow knew exactly why even if he wasn’t telling—. He said to have met very influential people as well.
“Do you know a lot of important people?” Shadow tilted his head, trying to appear clueless. He knew it was best to feign ignorance, even before Rouge had offered that advice; it was a manipulation tactic he used in the past. Robert laughed as he opened the door to the room, Shadow having to will himself into stepping inside. He could still turn back if he wanted, even as the man closed the door behind them with a telling click.
“You’re curious about that?” He sounded amused by Shadow’s questioning, almost fond, but the hedgehog knew to recognize when he was being talked down to. Oh, if the man only knew. He nodded, but then froze when he was suddenly lifted under the arms, brain barely catching on it when he was sat on the bed, back propped on the headboard like a doll. He looked up at the human man with huge eyes as he unbuttoned his shirt, eating him up with his eyes the whole time.
“Yes, of course,” he cleared his throat and shifted to sit at the edge of the bed, as to not feel so trapped, “you say they’re influential, right? Do you ask them for favors?”
The tilt of his head and dropped ears seemed to do the job at dissipating any doubt in his innocence, Robert chuckled again as he stepped closer, his shirt now open and revealing his abdomen. He had a bit of a belly and was kinda hairy, but still running for the title of most unimpressive man Shadow had ever seen.
“Sometimes, you’ll find people will do a lot of things for the right price,” he said as he cupped Shadow’s face, just staring for a moment before adding, “you know, you seem familiar somehow.”
Shadow could feel his heart fucking stop, blood draining from his face while keeping as still as possible. There was no way the guy knew him, he thought, GUN kept Shadow’s existence an open secret, for a multitude of reasons, and he wasn’t really dying to find fame and recognition for his work. But there were still people who knew him, and this guy had talked to Eggman, and no one knew what those conversations were about because he was supposed to find out but he was too busy looking like an idiot with his face held between this man’s hands.
“People tell me I look a lot like Sonic the hedgehog.”
That made Robert pause, a beat of silence between them until Shadow heard him hum, bringing their faces closer together as he ran a thumb over his lower lip.
“Yeah I can see it,” he breathed, the warmth of it making Shadow gulp. He smelled like strong mouthwash, “You’re cuter, though.”
The kiss wasn’t really unexpected, but it still made Shadow jump and give a muffled protest. Trying to move back only brought the man to follow, so he had to prop himself on one hand while the other held onto Robert’s shirt for dear life, not wanting to fall and be trapped on his back. The lips were strangely soft, probably the first thing about him to actually stand out, and Shadow gasped when a tongue pressed hotly against his lower lip.
This was quite the conundrum. He really did not want things to move further but could he really reject a kiss in his position? Would Rouge have accepted a kiss? It was hard to imagine, surely she’d weasel her way out somehow, always looking so composed and self assured.
He decided to just open his mouth and see where that took him, what harm could a kiss do? Not like he could talk his way out without making a fool of himself.
He didn’t expect it to be so… overbearing. Robert pulling him closer by the back of his neck and tilting his head so his tongue reached everywhere, almost big enough to make him choke. It danced around his tongue, pressed it back, licked over his sharp fangs and then over his lips, Shadow following to the best of his ability. Robert was making a lot of low, breathy noises, sighing and puffing into his mouth, only making Shadow more flustered as he couldn’t swallow down a few noises of his own. He felt his lungs burn and knew he really needed to pull back for air, whimpering pitiably while that big tongue threatened with penetrating his throat. He swallowed a very embarrassing sound when a hand began slowly creeping up his leg, lifting his skirt, stroking his thighs, touching his-
“Any news yet?”
Shadow nearly choked at Rouge’s voice, eyes wide as he ripped himself away from the kiss. It was like getting slapped on the face, had he been getting too into that just now?
Robert gave him a funny look again, thankfully sitting back a little.
“What? Did I take your breath away?” he said, and Shadow couldn’t even react to the cheesy line as he ducked and slipped past him, hurrying towards the only other door in the room.
“I need to use the bathroom,” was all the explanation he gave, nearly slamming the door behind him. He had some trouble regaining his breath.
“Shadow? Is everything alright?”
“Yes,” he replied instantly and heard her sigh in relief. “Have you found anything?”
She sighed again, “I’m sitting in his study right now, his computer is clean so he must keep a physical drive somewhere. I swear I’ve checked three bedrooms and every fucking drawer, Shadow, this place is driving me crazy!”
Shadow winced, it had to be very bad to make Rouge this heated.
“Maybe he carries it with him,” he said evenly, and Rouge groaned ‘please don’t tell me’, the sound of papers crinkling loud enough to get to him, “I’ve found a way to get close to him, I’ll get his briefcase and also give you more time to search.”
The silence that followed was a beat too long for comfort, Shadow shrinking slightly under the weight of it as he feared what she must be thinking.
“And just what do you mean by that?” Her voice was scarily calm, he knew exactly what that meant. He couldn’t blame her for being disturbed, given that he couldn’t bring himself to say it either.
“Rouge, it’ll be fine.”
“Shadow I swear to god if you-”
“Everything alright in there?” A knock came on the door, Shadow almost bit his tongue as Rouge fell silent again. This had to look so bad.
Instead of continuing to reassure her, he turned the comm off; he had no time to explain and having her voice in his ear would only make things more difficult. He didn’t reply to Robert either, just took a deep breath and readjusted his skirt, before reentering the bedroom with as much confidence as he could manage.
“Sorry about-” That didn’t last long, next thing he knew he was hoisted off the floor again, this time more brusquely, and he couldn’t help but yell and kick out at who had grabbed him. He was thrown face down on the bed before he could land a hit, adrenaline kicking his body in full gear as he sat up rapidly, but all the air left him when another body jumped on top of him, straddling his hips and pinning him on his belly, big hands pressing him down firmly by the shoulders. He couldn’t breathe.
“You took so long in there,” Robert’s voice came from somewhere above him, lifting his hips to shift into a position Shadow couldn’t see, and he gasped like a dying man, trying to wiggle free but freezing when he felt something hard and hot poke him from behind, “Were you talking to someone?”
“N-no?” He said quickly, hopping to sound more confused over an outlandish accusation rather than squeaking like a mouse caught in a trap. Robert just chuckled, not a reassuring sound, one hand trailing down his side and stopping at his hip to pull the skirt down, making Shadow’s spines puff up in distress, “Careful!” He warned with a hiss.
“Don’t worry, I know hedgehogs are tricky to handle, I won’t prick myself.” That was not what Shadow meant, but he lost his chance to explain further when that stray hand grabbed his tail and pulled hard, forcing him to yelp and bring his knees up to lift his hips and take some of the strain off. He blushed and scowled furiously at the indignant treatment, wanting nothing but to buck the other off, but the grip on his tail was iron strong and he did not want to feel like his spine was being ripped from behind.
“That hurts!” He protested, kicking back but missing his mark, receiving a cruel twist for his trouble.
One hand on his tail and another gripping his hip was all that held him down now, at least allowing him to prop himself up on his elbows so his back wasn’t arched uncomfortably. He tried to turn and glare at the other, not really managing to look over his shoulder, but noticing how Robert seemed to have disappeared from view behind his lifted bottom.
Then a hot puff of breath was blown under his tail, right on his pink pucker, and he nearly choked again.
“Some men can be so cruel, you know,” Robert’s voice breathed far too close to his butthole, Shadow involuntarily tried to flinch back and only managed to pull on his tail. He was extremely confused, to say the least, both by Robert’s words and actions. His brain once again screeched to a halt when a thumb brushed over that ring of muscle, barely adding any pressure but making Shadow’s head spin all the same, “They don’t know how to use a hole like this, it’s far too small to fit a human, but that’s what makes it so cute, I think.”
“W-wait, wait, I don’t-” he cut himself off with a sharp gasp when he felt Robert lick him, starting at the juncture between hip and his left thigh, passing over his pucker with more vigor before ending at the base of his tail. His whole body tensed up. “Whu-wha-?!”
Robert didn’t spare him anymore words, leaving a little kiss on his butthole that did not help with his confusion, only to then press his open mouth to it and lap at it with his tongue, like it was some sort of hard candy. That made Shadow squeak, specially as that tongue started making circular motions around his flesh, the brush and the pressure and the moist and the hotness of his breath were a combination he never expected to feel so good in there.
“What’re- w-what’s- Mmmh-ngh! N-no!” Shadow cried out when the pressure increased, the man flattening his tongue over the sensitive flesh, lapping at it once more before pressing in, the tip of his tongue just barely breaching past tightly closed muscle, trying hard to squirm inside until it stung, drawing back only to lunge back in deeper.
Shadow kept trying to get away from the strange sensation, only now noticing his tail was freed for the sake of holding his hips in a bruising grip, Robert keeping his backside affixed to his hungry mouth, unrelenting. Whenever Shadow managed to scoot forward even slightly, the man’s face followed, next time he nibbled at the flesh of his butt just to plunge that tongue as deep as it would go inside him Shadow actually moaned, having trouble keeping himself propped up.
Why was this happening? Was this supposed to happen? Shadow had never expected anything like this, nothing to feel like this. He hadn’t wanted to have sex with Robert, but, did this even count? What even was this?
“What are you d-doing? Hhhah~” That tongue was reaching so deep inside of him now, it lapped at his insides, pressed against his walls and made weird, jerky motions inside him. He was starting to feel tingly all over, something heavy and hot building right under Robert’s tongue and he couldn’t help but sob at the intensity of it, arms shaking, legs shaking, why wouldn’t he stop?
Suddenly Robert pulled back, Shadow making a confused whiny sound when his chest was pushed all the way down to the mattress, the man shushing him gently as he positioned him, Shadow pliable like clay under his hands. He still gasped when Robert lifted his bottom even farther, knees barely brushing the sheets now as body was bent at a weird angle, Shadow barely managing a wobbly whine before that hot mouth was on him again, lips encircling his flushed entrance in an obscene kiss that had him mewling pathetically, drooling and nibbling at the sheets, those mewling sounds getting several pitches higher when Robert penetrated him with his tongue again, this time humming while he drew circles inside him, stretching his walls further apart.
After an insufferably long time, he pulled away with a popping sound that Shadow replied to with something between a sob and a moan.
“See? Even after all of that you’re still so tight…” Shadow could do nothing about the fingers brushing over his stretched hole, legs dangling uselessly and everything else still too hot and shaky. Without warning, one of those fingers entered him, burying itself to the knuckle in there. Shadow tensed all over again, balling up the sheets in his fists and shaking his head helplessly.
“H-hurts…” He sobbed when that finger started pulling back, just so another digit could join him at the entrance, Robert having inserted his thumb and index finger to pull the muscle walls of his hole apart as far as he could, this time making Shadow flinch and cry out. “Hurts! It hurts, please!”
“I can see that.” There was something complicated about Robert’s tone that was giving Shadow an even worse feeling. An index finger was still buried inside him when Robert leaned down one more time, sliding his tongue alongside it, and now Shadow was gasping and writhing under him, the stretch almost too much until he inevitably adjusted, panting much harder now as his insides were stroked, eyes half lidded and glazed over.
He groaned and clenched down when a second finger was added, pressing down while that tongue twisted up, opening him up so wide… then it went deeper and pushed harder, and this time the feeling was completely different, as it bumped against something that made Shadow see white, eyes rolling up as he moaned loudly, his jaw slack over a pool of drool.
“Ah-hahhh aahh-I can’t, I can’t, I ca-AHH!” he writhed and cried when Robert pulled his mouth away only to start violently fingering him, brushing that spot over and over until Shadow couldn’t breath, couldn’t hear, couldn’t think-
“Do you want my cock now, bitch?” Robert’s voice barely broke through the haze, receiving a questioning whine and a moan in response. Something sounded so wrong about that, but he couldn’t- “I bet you think you can take it, huh? You stupid cunt, you’re so tight, fuck!”
Shadow nearly screams when the man stopped holding him up, the sudden emptiness shocking him almost as much as the violent way in which Robert turned him around, Shadow’s limp head whipping around by the force he was jostled with. He was roughly caught by the wrists, and he sobered up almost immediately when Robert placed himself between his parted legs, pushing them up over his thighs, looking absolutely enraged. Panic was coming back to him fast.
“Robert?”
“You’re not a whore at all, are you?” He spat at him, Shadow’s eyes nearly bulging out of his head as he sputtered dumbly, not yet understanding how he went from one compromising position to another in a split second. What was he supposed to say to that?
“I don’t- I wasn’t trying to-!”
“Do you think I’m stupid? I know what kind of hole I’m fucking and that’s not- do you even work here?!” He seemed to only to get angrier at Shadow’s dumbstruck face, and when it seemed like the hedgehog was about to start struggling against him, he pinned one of his spread thighs under his heavier knee, “What were you doing staring at me all night? And all the questions? Are you trying to-”
Shadow’s heart skipped a beat when he noticed where Robert’s eyes had trailed down to, unable to close his legs, he only managed to bump his knee against the other man’s waist weakly, whimpering in shame.
A completely messed up patch of fur sat between his legs, sex exposed and swollen with arousal as it dripped endless gushes of slick, Shadow somehow still coming from the rim job. He didn’t know how to feel about being this exposed in front of Robert, having been through one humiliating ordeal to another, he couldn’t decide if this was truly worse than all the rest. But he was still so painfully aroused, Robert’s dark, lustful eyes stuck to his pussy were making him tremble with something terrible.
To make matters worse, the man looked down at his chest, where he’d held Shadow’s hips earlier, and indeed found it sticky with the stuff coming out of him. Shadow blushed furiously, but Robert didn’t seem upset.
“Oh. I could’ve sworn you had a penis.”
He did, actually, and it was also growing painfully hard inside of its sheath, but Robert did not need to know that and it would not be coming out if he could help it. Not trusting his voice, Shadow just shook his head, bringing his aching wrists to his chest when Robert wrapped his hands around his thighs, thumbs brushing dangerously close to his pussy as he massaged there mindlessly, smile stretching in his face and Shadow gulped. He wouldn’t… he didn’t want to.
Did he?
“I guess I should’ve started here, that was my bad,” he said, oblivious to Shadow’s current inner crisis. His eyes trailed off to once again check the briefcase sitting besides the bed, and he thought of Rouge, and how worried she must be, and how he really needed to finish this job before he got into even more trouble.
A thumb pressed on his perineum and Shadow’s hips jumped, drawing a squeaky sound from him. Robert licked his lips and his heart kept beating faster and faster.
That tongue felt so good in his mouth. In his ass. How would it feel there?
“It would be rude of me not to wash my hands first, though.” The man gave him a cheeky grin, and Shadow could only stare and nod, receiving a soft pat on his belly, and then Robert leaned over him to reward him with another drawn out kiss, that Shadow couldn’t help melting into, “Be right back, wait for me, okay babe?”
Another nod, and Robert was gone inside the bathroom. Shadow laid there, dazed, taking deep breaths, feeling both of his holes throbbing and his body impossibly heavy. How long would Robert take? He hoped it wasn't long, he really wanted his mouth on-
He shook his head with a groan, finally deciding to get up. Just what the hell was he thinking? What had happened to him there?
He kicked off the skirt still stuck to one of his ankles, and also threw the heels away. Rouge would have to forgive him for losing them but he just couldn’t deal with them right now. He finally got a hold of the briefcase, it looked comically big for him to be carrying, but he didn’t care, he just stepped out of the room with it, no clothes and messy make up, and ran out and away from the nightclub until his feet starting hurting. Rouge would have to hear him cry about it later.