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Late Night Devil, Put Your Hands on Me

Summary:

Daryl picks the wrong pocket, and has a long night that might lead to more?

Tags are progressive and this ended up absolutely leading to more so there's that.

Notes:

This is an idea from Berserker2166 that I kidnapped and ran with. We're in a discord for Degan if you're interested ask tillthewheelsfalloff!

I might add more chapters, I have a vague idea and will update tags as I add chapters

(See the end of the work for more notes.)

Chapter 1: Meeting Negan

Chapter Text

Daryl snagged another handful of stale pretzels as he passed the bowl, earning a glare from the bartender. If he didn’t buy something soon he knew they would toss him out. Getting tossed meant that he wouldn’t be able to come back for a while, and this was one of the few bars that still had pretzels, and sometimes peanuts, out for clients with questionable food safety standards to dip their hands in and eat for free. But the thirty dollars in his pocket had to make it until his next payday in a week, so he couldn’t buy a drink and still expect to put gas in his bike to get to work. 

He should have had plenty, but Merle had needed bail money and last time Daryl waited he ended up with added time from fighting in jail and had his bail revoked. Merle was crashed on his floor, Daryl having sold the couch two months ago to make rent, the idea of going back ‘home’ also wasn’t appealing. 

With no other option, he turned to leave anyway and he spotted him.

Tall, older, striking dark eyes, and black slicked back hair. His shoulders filled out his leather jacket, but Daryl couldn’t tell if it was muscle or trick of the jacket. He’d bet on muscle, but he’d been wrong before. A flick down to check out the rest of the stranger, and Daryl’s eyes snagged on a wallet that was sticking out of his back pocket, easy pickings. Switching gears, Daryl lined himself up so that he would brush past the guy as he walked by, muttering a “Sorry,” as his hand brushed the top of the guy’s pocket and snagged the wallet. 

A tight painful grip wrapped around his wrist, bones grinding, skin hot. Definitely muscles

“Hey, let go!” Daryl snapped, his voice pitched to carry and draw attention. He was smaller than the angry stranger, he widened his eyes and gave a little tug, trying to garner sympathy from those around him. This wasn’t a biker bar where the weakness would just get more people to pile on, and he could already see the patrons nearby frowning as they turned around.

The stranger tugged him close, easily forcing Daryl into his space. The look in his eyes was hot, but Daryl couldn’t tell if he should be bracing for a punch or not. The smile on his lips wasn’t enough of an indicator as his whole face looked dangerous and slightly cruel. 

“Usually, I have to buy a guy a drink to get him to stick a hand in my pants.” Daryl shuddered as the man’s breath tickled his ear and the growled words caused blood to pool south. “But this works too.”

“I ain’t no fag,” Daryl snapped, glaring and adding another tug, but less obvious. Then he suddenly flushed, remembering that he chose a gay bar for the night. One man who had stepped forward to defend him jerked back like he’d been hit and glared before pointedly turning away.

“Not sure you should be using that word here,” the stranger purred and Daryl flushed at the way the tone seemed to caress his skin. 

“Fuck off,” Daryl said, all heat gone from his voice, a token protest.

“That’s more my style, anyway.” His eyes twinkling, the stranger let his wrist go, snagging his wallet back. “Come on. I’ll buy you a drink.”

He didn’t wait for Daryl to answer, his hand grabbing and digging into Daryl’s shoulder as he manhandled him over to a corner of the bar, away from the door and closer to the bathrooms. Daryl’s treacherous body couldn’t decide if he should be scared or turned on, he had his own muscles, but was being manhandled like he weighed nothing. If the stranger tried to get him out of the bar he would put up more of a fight, but it was better to follow along with the risk that the cops could be called. 

As soon as they got to the bar the bartender materialized, looking chipper and focused on the stranger. “Negan, sir, what can I get you?”

Shit. It was obvious that the stranger, Negan, was known here. No way he was getting out of this unscathed, desire cooled as anxiety started pressing at him. 

“Hey, Dwight, get me a whiskey sour. Get my friend here a tequila shot.” Negan looked at Daryl with heat and challenge, and Daryl fought down surprise as he would have ordered a tequila if he was given a chance. “Go ahead and add an orange slice.”

The drinks appeared instantly, making it more and more obvious that Negan was a big shot as every other person standing at the counter had to wait. Daryl watched as Negan picked up the drinks and gestured with his head to an empty booth, debating if he could run faster than Negan could shout at the bouncer to stop him.

Just suck it up, take your licks, and try to salvage this. Prior to tonight this bar was the closest thing to a safe space Daryl had. The free food and generally safer clientele being part of it. But another big piece was Daryl knew that if things got bad enough he could take someone in the bathroom and make enough money for gas or rent on his knees. The twisting in his stomach at that thought was nothing compared to losing his job because he couldn’t make it to work, or losing his shitty apartment because he couldn’t make rent.

Daryl slid into the booth and picked up the drink, flashing a look at Negan to make sure he was supposed to drink it. When Negan nodded and took a sip from his own glass Daryl downed the shot before slipping the orange peel off and devouring it. 

It occurred to him before he took the drink that it could be drugged, orange slice a code word, but there wasn’t much he could do about it. If Negan wanted him drugged at least he wouldn’t be awake for whatever revenge he had planned. If Negan didn’t want him drugged that wasn’t necessarily better, but he could make sure Negan knew he didn’t have to rough Daryl up to get what he wanted.

With that in mind, Daryl ducked his head and looked down at his hands, still curled around his shot glass, fingers spinning it slightly. “Sorry ‘bout your wallet. Thanks for the drink.”

Negan chuckled darkly and leaned back, his legs crowding towards Daryl’s side and boxing him in. “I’m leaning towards forgiving you.”

Daryl kept his eyes down on the table, fighting back the fear to focus on placating Negan, he intentionally shifted a little and knocked his legs on the inside of Negan’s. “‘Preciate it.”

“I know I’ve seen you around here,” Negan said, with a little challenging note in his voice. There wasn’t anything to say to that so Daryl hmmed in acknowledgement. “Speak when you’re spoken to,” the order silky smooth, used to telling people what to do. 

The tone sent blood pooling south again and Daryl fought back a smart ass comment that could get his jaw broken. “Come here sometimes.”

Negan looked across the table at him and Daryl could feel the stare, despite refusing to meet it. “Kinda strange if you aren’t gay. Although, I guess you don’t have to be to steal men’s money or get on your knees.”

Daryl clenched his jaw to keep back the angry retort. It wasn’t a question, he didn’t need to answer or say anything.

Negan sat across from him and waited. The silence stretched and Daryl felt the pressure building. “How do you… you been watchin’ me?” Daryl fought to sound more pissed off than scared, feeling like an alley cat trapped with a junkyard dog baring down on him. 

“Mmmm.” Apparently having to speak sentences was not something that Negan required of himself. “Come on, I’ll show you.”

Negan pulled back to his side of the booth and then stood staring down at Daryl, a challenge in his eyes.

Daryl felt the tequila sitting in his stomach churn as he stood up, Negan turned and walked away as though Daryl following was a forgone conclusion. Daryl shot a look over at the exit only to see the large redheaded bouncer giving him a glare. 

Daryl took a deep breath and followed Negan, who took him through an employee’s only door to the back room.

There were stacks of supplies everywhere, but Negan ignored them, heading towards two doors, one said lounge and the other had Negan’s name on it.

The fucking owner. Daryl had tried to rip off the owner of the bar. The door closed and the sounds of the bar disappeared with a finality. There were monitors on the wall, but Daryl only quickly glanced at them, taking the lay of the land.

There was a black leather couch against one wall, a large desk caddy corner to the wall of monitors, a swiveling desk chair, and a mini fridge completed the space. Multiple places to bend Daryl over, but the open space they currently stood in would be preferable. Maybe I can convince him to just let me blow him.

He hadn’t even gotten to keep the wallet. Whatever happened next, the only thing he was walking away with so far was a shot of tequila and a thin orange slice. Frustration welled and was instantly squashed, it wasn’t going to help him right now.

Negan was behind him, having closed the door, Daryl took two quick strides, getting closer to the desk, before turning and kneeling. 

Negan hadn’t moved, but there was a look in his eye and a bulge in his pants.

“While that’s a pretty sight. But I think we need to talk first.” A pleased rumble in his tone soothed Daryl some, despite his words.

“Don’ wanna talk.” Negan’s face darkened and Daryl closed his eyes, knowing he wasn’t successful in keeping the attitude from his tone. But really couldn’t they just get it over with?

Hands around his throat made his eyes fly open and he fought the urge to jerk away, pissing Negan off more now would just make it all worse. A strong thumb and forefinger rested under either side of his jaw, applied pressure, and Daryl rose with it, heart pounding.

“I want to fuck you.” The words felt like a tidal wave through Daryl’s body, leaving ripples of desire and fear. He hadn’t done that before, had avoided selling his ass despite how it paid better than his mouth. Negan was attractive, smelling of leather and soap, could be worse he guessed. Of course, Negan could always make it worse.

Daryl looked into his eyes and was surprised to find kindness there. “Figured.” The words vibrated against the grip on his throat.

“You okay with that?” Daryl knew surprise showed on his face. “I’m not interested in raping you. This isn’t about the wallet. If you want, you can walk out right now, you can still come back and surf the free pretzels and condoms in the bathrooms.”

Oh, oohh . The thought stuttered through Daryl. He had a choice. To test that he leaned back, and the hand loosened from around his throat and fell down to Negan’s side. Negan took a step to the side, giving Daryl a clear line to the door.

Daryl took a step and Negan gave him more space. Desire pulsed hard without the fear to quell it. This could still go wrong, Negan was bigger and stronger and they were isolated back in his office. If Daryl agreed, what was he agreeing to? 

“‘K,” the word, letter ?, was all Daryl could get around the lump in his throat. But he realized he wanted and it seemed like Negan knew exactly what to do.

“You used the light system before?” Negan asked, still waiting off to the side, still allowing Daryl an out. Daryl knew better than to try and bullshit him and shook his head. 

“I ask you your color. Green means good, yellow means slow down, red means stop. You say red and we stop,” Negan reiterated with a bit of force and Daryl didn’t suppress the shudder that swept through him. “I like to be a bit rough, and I like to push you around. I don’t stop for no, or stop, or don’t. You tell me red or I keep going, got it?”

Daryl nodded, suddenly not entirely sure about what was about to happen, but also still interested enough to try. “Green is go. Yellow is slow. Red is stop.” 

“Exactly right. Now get on your knees.” Negan’s tone shifted and Daryl slid back to his knees, with the exit to his back and Negan in front of him. “Hands on your thighs, that’s it. That’s exactly right.”

Negan reached down and rubbed himself through his pants while looking Daryl over, he came back into Daryl’s space and stopped close enough that he could feel his body heat and the bulge was eye level. “Now take my cock out, and make sure I’m ready to fuck you with it.”

Daryl got a little lightheaded, a wave of desire crashing through him and pooling south. His hands came up and they were shaking, but he got Negan’s belt undone and his buttons and zipper dealt with. With how large the bulge had been, Daryl was expecting Negan to already be fully hard, but the monstrous dick in front of him was only sporting a semi.

Trepidation filled him, but when he looked up Negan was looking down at him with an eyebrow cocked. Daryl looked back at it and took it in hand, bringing the head up to give it a lick. Negan tasted clean and smelled of soap even down here, something Daryl could appreciate given the other cocks he’d sucked. After a second, he popped the head in his mouth, stroking with one hand while the other reached for Negan’s balls.

He gave an experimental light squeeze with both hands while sucking on the head. Negan made a groaning sound of approval and his hand landed on the back of Daryl’s head near his neck, resting lightly but also an unspoken order. For a moment, Daryl considered ignoring the threat, but it occurred to him that the light system didn’t really work with his mouth full of cock. Rather than push his luck on something as trivial as a blow job he started to bob to swallow Negan, but there was no way the whole thing was going to fit as it started to grow and fill his mouth.

Right as Daryl started to get concerned about choking, the hand in his hair twisted and pulled him off and up. The grip was just the right side of painful, and Daryl felt a whine build in his chest. Negan manhandled him around and suddenly he was backed against the desk, which pressed just below his ass.

“Clothes off,” Negan ordered, stepping back and not moving to undress anymore than pulling his pants a little further down. 

Daryl shed his pants, underwear, and shoes, feeling that if he hesitated Negan would take them off less gently and he couldn’t afford more right now. While he stripped, Negan reached to the side and opened what appeared to be a candy dish, inside were condoms and individual lube packets. 

He must have to special order them, was the only thought that ran through Daryl’s head as Negan rolled a condom on. The condom wasn’t like the free ones from the bowls in the bathrooms that Daryl was used to using, these looked expensive and were already lubed. 

Negan raised an eyebrow as Daryl fiddled with his shirt, before he took a deep breath and stared him down. 

“Shirt off,” Negan said, his tone firm and Daryl touched it again, his heart starting to pound. Negan stepped forward and Daryl almost let him take it, but if he was going to push back was this the right time? Was it a good idea to try the light system, see if it mattered? If it pissed Negan off and he didn’t listen then at least Daryl knew not to try it later, he didn’t want to try it when he needed a red if it was just going to make Negan worse.

“Yellow,” Daryl barely breathed the word as Negan grasped the shirt and he paused, assessing Daryl before letting the shirt go and stepping back. Relief made Daryl sway towards him, he listened , but now Daryl was worried that Negan would stop. “Green,” he whined, trying to communicate that he was good as long as Negan left his shirt on. 

Daryl stood there waiting for Negan’s next move, would he continue or had Daryl blown it? Negan looked him dead in the eye, and he tore open the packet with his teeth, spreading the lube on two fingers. “Bend over the desk.”

Daryl’s own cock started leaking pre-cum as he turned, a flush that was a mixture of embarrassment and desire spreading across his chest. A boot connected with the side of his foot, knocking his legs further apart as the unlubed hand pressed him further into the desk. He turned his head sideways and squeezed his eyes shut as fingers started tracing his crack, brushing against his hole.

“There it is,” Negan murmured as he started to press slick fingers against Daryl’s hole, the feeling was strange but not unpleasant, not yet.  

Daryl had heard mixed things about anal, he knew that it could hurt and hurt badly. But he also knew that a lot of guys really preferred it, and he wanted to know why. As pressure built there was a slight burn and the murmured instructions started back up. “Let me in. Come on, Gorgeous, let me in.”

“Don’t… Don’t know how,” Daryl finally groaned as the pressure increased and a finger slid in anyways. There was a pause as Negan held still at that, Daryl just had a moment to realize what he had revealed when Negan started rocking the finger in and out. 

“You’ve never done this before?” There was a strange new tone in Negan’s voice. 

“No,” Daryl grunted as the finger slid in and out. Now that it was in, the glide wasn’t painful, just different, but still nothing to write home about. Despite that, Daryl felt his erection take a little jolt at the motions, something about knowing that Negan was thrusting into him making him start leaking more.

He felt a second finger pressing along the first, but this time Negan told him what to do. “Push out a little, that’s it,” the second finger still burned but it was definitely easier. Then Negan was moving them both and Daryl couldn’t get over how strange it felt before suddenly he yelped. 

Negan had found something inside him that made Daryl both jerk away then rock back, needing it again. “Easy now, you’re about to break my fingers off. So fuckin’ tight, Gorgeous.” 

The words started to blur in Daryl’s mind as the fingers found that spot again and started stroking it from the inside. He barely registered when a third finger joined and a fourth, all of them petting him from the inside in a way that made him bite down on his lip hard enough to taste blood. When they left Daryl felt cold and empty and almost reared up, pushing against the hand pinning him with a breathy whined, “No, please,” punching out of him.

But then he felt the blunt tip of Negan’s cock against his hole and he pushed, desperate to have him inside and back touching that spot. There was pain, but it was short lived as Negan’s entire monstrous cock dragged against that spot. 

Once fully inside, Negan didn’t wait for Daryl to adjust, he started rocking right away, each powerful thrust pushing his hips into the desk and Daryl’s erection wept for attention where it was pinned. It was all Daryl could do to hold on and he knew he needed more and also less. 

“Wait… please… stop… I need…” Daryl gasped out, trying desperately to think through the pleasure/pain that was assaulting him. But Negan just picked up the pace.

“That’s not the right word,” Negan reminded with a punishing snap of his hips. “I know what you need.” He reached down and grasped Daryl’s hair again, pulling him up so that he was flush against Negan’s chest, the heat eating its way through his and Negan’s shirts. A hot arm appeared across Daryl’s chest to support him and press him further into Negan, the scent of leather enveloping him.

Daryl keened as the change in position drove Negan deeper, and he stood on the tips of his toes to try and relieve the pressure on his hair and neck. Negan continued to grind into him and Daryl just panted, grasping at the arm and desperate to ride out the waves of a pleasure he didn’t know existed. 

Negan let go of Daryl’s hair and reached down to tug one of his legs up to rest against the desk, somehow getting even deeper. “You’re going to feel me for days. When you ride your bike, the vibrations of the engine will touch you deep. Where only I’ve been, you’ll feel it and remember me.”

Daryl knew that was going to be the case for more than a few days. He threw his head back to rest against Negan’s chest as his eyes started to roll into the back of his head, the words hitting him in some spot that only Negan knew he had. 

“Please… Fuck… Touch me,” Daryl finally gasped out.

The chuckle that rippled behind him made him see stars, even as a hand reached to lightly grasp his cock. “Like this?” Negan mocked.

“Harder… You bastard… Harder… Unngh.” Daryl’s words were choked off as teeth found his shoulder and bit down. 

“In that case, if you know what you need.” Suddenly, Daryl was airborne, strong arms scooping underneath his thighs and he was being carried. Little thrusts forced gasps from him, as each step took him backwards until he was sitting on Negan’s lap on the couch. “Fuck yourself on my cock.”

Daryl was already trying to move, almost mindless except for the knowledge that he needed it harder, faster, more. Hands guided him to the right angle and he started riding Negan, too far gone to care about anything but the spot inside of him and the feeling of Negan hitting it. It still wasn’t enough and Daryl wanted to cry, then suddenly Negan was reaching around and his grip was punishing, but also right, and Daryl was fucking into his hand and back onto his cock.

When he finally cums he was a mess, covered in sweat, his shirt practically see thru with it. He came all over the concrete floor of Negan’s office, and Negan was still hard and now moving in him and now it is too much, he was too sensitive and spent and he couldn’t take anymore. Right as he started to try and gasp out a yellow he feels heat as Negan stuttered and cums in the condom.

Daryl’s legs were jello, and Negan turned to the side to slowly slip out of him, before moving him into a more comfortable position on the couch. Daryl was still trying to catch his breath, left cold without Negan’s body pressed against his, when he heard Negan moving around the office, pulling his condom off and throwing it away. There was a rip of paper towels and then Daryl felt his legs being maneuvered, he was being cleaned up, the paper towels almost too rough on his skin. Negan left and there was the sound of a small fridge opening and closing. Then Negan was in front of him, crouched down with a small smile.

“Drink this.” It’s Gatorade, the blue kind. The top was already cracked which was good because Daryl’s arms were practically useless and he was pretty sure Negan wasn’t going to drug him so the extra courtesy was unexpected but welcome. A sandwich also appeared in front of him. “Eat this.”

Daryl sat up a little and looked around with dazed eyes. Negan was still dressed, now tucked back into his pants and the room was cleaned up, Daryl’s clothes piled on the arm of the couch.

“You are welcome to stay here for a little while, I have some things I need to attend to.” Negan’s voice was soothing and low, and he was carding his hands gently through Daryl’s hair. 

“Do you see that clock?” There was a big clock with the small hand pointed at the ten and the large hand was halfway between the one and the two. “At eleven-thirty I am going to be back. If you are still here I assume you are interested in doing this again tonight.”

Daryl paused drinking, looking at Negan. “If you aren’t here I’m assuming we’re done for tonight. But I am interested in doing this again, so let Abraham at the door know you’re here if you come and I’m not around.”

Daryl nodded, reaching for the sandwich and starting to unwrap it. Words were beyond him, but he struggled to make sure he understood what Negan was saying. 

Negan was leaving, he wanted to fuck again, if not tonight Daryl could come back another night.

The hands in his hair stop and Negan stood, looking down at him. Other than a slight flush to his face, no one would know he’d just fucked Daryl stupid in his office. But Daryl knew.

“I had fun. You did good. I hope to see you again.” Negan turned and left, the curt matter of fact praise making Daryl blush. 

Daryl took a bite of the sandwich and hummed around the barbeque inside. Idly thinking that no matter how much money was in Negan’s wallet, this was definitely the best way tonight could have turned out.