* Requested by: @CocoaOtaku89 , @Nyuleen_200 & @Guccivanna *
Hey guys so this lemon is a bit dirtier than what I normally put out but then again to some people it might not be so bad, but regardless it's Diavolo so like what did ya expect lol?
Your hand hovered over the door to the boss's office, you were prepared to knock but hesitated. You were appointed as the mafia's new Consigliere, since the last one had been killed by the boss (which to be honest, frightened you to some degree). You climbed your way through the ranks just to get to this point and you were amazed at how smoothly the whole "interview" went. You met the mafia's underboss Doppio, and he seemed way too frail to even be apart of a gang. He smiled at you with kind eyes and was very thorough about what he expected of you taking on this new position. You had asked Doppio the burning question, who was the boss? But all he did was smile and said that you'd find out soon enough...
You had been apart of Passione for quite sometime, you surpassed most of the men around you going from a soldier, to a capo quite quickly. You only considered being the boss's right hand advisor because he himself seemed like a man who just radiated confidence. He was cool and collected and his movements were always calculated. He was definitely no moron, he was bright and that was the kind of person you wanted to work for (and for the obvious reason, you just wanted to know who he was and what he looked like).
You hoped the boss would accept you and help you grow develop just like you would do your best to help him. Doppio was pretty accepting of you already, but who's to say the boss felt the same?
Today you expected to meet the boss. You were nervous yet excited all at the same time to get to meet him face to face. So with a shaking fist, you knocked on the door.
No answer.
You knocked once more and was met with the same response.
Your hand moved towards the doorknob and you slowly turned it. The door was unlocked! You slowly opened the door only to be met with a dark room. There was some light just peeking in from between the closed curtains onto the boss's desk. You took a step forward and closed the door behind you.
It was dead silent, you could only hear the sounds of your shoes clack against the wooden floor. You felt a bit of anxiety as you made your way to his desk. Everything was stacked neatly before you, there wasn't a single thing out of place except for one paper.
Upon further examination it had your name on it.
Did the boss do a background check on you?
You went to reach for it until your heard a bone chilling voice speak behind you.
"Don't you know better than to touch other people's things?"
You froze in place at that voice. His arm had snaked it's way around your waist while his other hand was placed on your shoulder. He was very close to you, so close that you could feel his warm breath tickle your earlobe. His lips curled into a smile as he watched your trembling figure.
"I've been expecting you... It's nice to finally meet face to face."
"Well I wouldn't say face to face..." You commented trying to sound brave.
He chuckled, "I knew Doppio made the right decision in recruiting you... Brave and bold in the eyes of danger."
His hand went from your shoulder to your neck. He didn't squeeze, he just placed it around your neck, while his thumb stroked your cheek. You clenched your jaw. It seemed like he was trying to figure you out.
"Hmm..." He said out loud, "You may turn around," He spoke.
He released his hold on you, and you did as you were instructed to. There he was in the flesh. Through the sliver of light from the curtains, the boss's green eyes seemed to glow. From what you could make out in the dark room, he was a well built man in a striped, all black suit, with his bright pink hair pulled back. A devilish grin was plastered on his face as he made eye contact with you.
His hand extended out to you, "Doppio has told me good things about you," He started, "From what I've learned about you and what I've witnessed, I expect nothing but the best from you here on out."
You nodded, "Y-Yes boss."
You took his large hand in yours and shook it.
"Good, now lets get started..."
***
You completed a series of missions for the boss since you had been recruited. He didn't normally go out on these missions with you, it was either Doppio or one of the guys from the boss's guard team who assisted you at all times.
You performed all your tasks to a T and that made the boss like you even more. You felt privileged that the boss had finally trusted you enough to be on a first name basis with you (instead of you just calling him "boss" all the time).
Diavolo, meaning the devil, how fitting for a mafia boss...
On many occasions you were by his side from sunrise to sunset. It was tough for Diavolo at times to maintain his status and keep track of what was going on around the city, so he used you and Doppio to keep tabs. You two were the only people he trusted wholeheartedly...
A new mission was in the works. Diavolo needed intel on a rising gang in the city. He wanted both you and Doppio to go out to a party and find out whatever you could. You nodded at his orders and headed towards the door of his office.
"Oh (Y/N)?" He called out to you.
"Yes?"
Diavolo rose from his chair and went to the far side of his room. He picked up something that was draped over a chair and covered in plastic. You watched as he walked over to your and handed it to you.
"This is a dress for tonight's event," He spoke, "Do not be late."
You nodded once again and exited the room with the dress in your hand. You went to your bedroom and laid the dress out on your bed.
"Wow..."
The dress was made of silk, it was soft and smooth to the touch.
There's no way I should be wearing something this nice...
You removed the plastic that was covering the dress and held it in front of you in the mirror.
"There's no way he knows my size...Right?"
You unzipped the dress and carefully slipped it on. It was a perfect fit.
He must know the female body quite well...
The thought made your stomach flip-flop.
Does that mean he has experience with other women?
You quickly shook your head, "What am I thinking?"
You hurriedly fixed your hair and did your makeup. Thankfully you had the perfect set of shoes to go with the exquisite dress you were given. You were touching up the last bit of your makeup when you heard a knock at your door.
"(Y/N)? It's Doppio, are you all set?"
You grabbed a matching purse and opened the door to see Doppio standing there in a similar tux to what the boss would wear. His eyes trailed your body from head to toe.
"W-Whoa..." He commented, "The boss really does know how to accentuate a women's best features..."
"Thanks Doppio," You said feeling a bit awkward, "I don't normally wear this kind of stuff."
"Well you should, if the boss didn't already like—"
Doppio stopped talking and seemed to be suffering from a spasm of some sort. You watched as his eyes went from light brown to an emerald green, similar to Diavolo's and within a second it was gone.
"Are you alright?" You asked.
"Never better," He smiled, "Let's get going, we don't want to be late!"
***
The two of you arrived at the party. As you as you walked in you immediately identified your target, the supposed boss of the opposing gang sat at a round table with a couple other men. They all seemed to be enjoying themselves and just generally having a good time.
The point of this mission wasn't to make contact with either of them, but just to sit and listen to what they discussed. You and Doppio arranged to sit at a table that was just concealed enough for them not to notice you, but for you to hear every word they were saying.
"Might as well get a drink," You said to Doppio, "I think we might be here awhile."
Doppio agreed. He stood to grab you both a drink until he made a ringing noise. You looked at him confused.
"You'll blow our cover if you keep making that weird noise!" You whispered angrily.
"S-Sorry," He spoke, "I think the boss is trying to call me—uh be right back!"
You watched as Doppio hurried away from the scene.
What the hell was with him today?
Regardless, you figured he'd take a little while so you decided to get yourself a drink. You approached the bartender at the party.
"Hmm... What to choose, what to choose..."
You examined the drink menu for a bit until you saw a finger point at a specific drink on the menu.
"This one I hear is pretty good."
You looked up to see one of the opposing boss's men standing right beside you. He had a large smile plastered on his face.
Mission failed...
"O-Oh is it?" You said trying not to blow your cover, "I've never had anything like it before."
"Trust me, I know you'll enjoy it..." He looked over at the bartender, "Two of those please!"
The bartender proceeded to make your drinks while you stood by the enemy.
"So..." He started, "What brings you here tonight?"
The bartender placed your drink in front of you.
"Well," You said while stirring your drink with your straw, "If I told you, I'd have to kill you," You teased.
He chuckled, "Oh come on now, a beautiful woman like yourself here alone at the bar, you have to belong to someone here or at least know someone... Or maybe you're just a spy?"
"A spy? Please I'm far from one... I just caught wind of this party from a friend, she told me there'd be plenty of eligible bachelors to choose from."
"I see," he smirked, "Well has anyone caught your eye yet?"
"Well yes actually, there is a certain someone... I should probably get back to them before they get worried..."
You turned to leave but the opposing boss grabbed onto your arm.
"W-Wait! Are you sure? You just got here and I didn't get a chance to talk to you..."
You grew nervous, you weren't quite sure how to react in this situation. You didn't want him to get the wrong idea and you didn't want to totally blow the mission.
"Listen I—"
"You heard her..." A voice interrupted.
The hairs on the back of your neck rose as you heard that same deep voice you heard the first day you were hired.
How did he get behind you so quick without alerting you?
"She's with me."
There he was dressed in formal attire, standing tall and proud. He NEVER risked going out in public especially for a measly mission like this one. He tugged at your arm and pulled you close to him. His arm comfortably rested at your waist, he was trying to protect you.
"L-Listen you! You don't know who you're messing with!" The guy spoke.
"I'm sure," Diavolo smirked.
A couple of men were alerted by the commotion and surrounded the two of you.
Shit...
You panicked to yourself, both of you were out numbered.
Where in the hell was Doppio when you both needed him?!
You looked up at Diavolo who showed no hint of backing down, if anything, he smiled. He looked down at you.
"Do me a favor, and close your eyes alright?"
Close your eyes?
"B-But if you need me too I can fight—"
"Just trust me... You do trust me right?" He questioned.
"O-Of course."
Diavolo's emerald eyes were fixated on you, his expression was gentle when he spoke to you.
Was he trying not to worry you?
You took a deep breath and slowly closed your eyes so you could no longer see him and only saw black. He held you close to him and shouted the name of something.
Within seconds Diavolo loosened his grip on you.
"It's okay, you can open them..."
You opened your eyes to see that the both of you were now outside of the restaurant where the party was being held.
"H-H-How did we get here?" You said while looking at a rapid rate.
Diavolo chuckled, "Maybe I'll explain it to you one day... But for now let's get you home, I have all the information I need..."
You had what felt like a million questions you wanted to ask him. But couldn't figure out the best way to just ask. Diavolo jutted out his arm to you for you to take and gently took hold of it. The streets were quiet tonight, it was just the two of you.
"You're a mysterious man," You spoke as the two of you began your walk, "I find it hard to keep up with you..."
Diavolo smiled, "Well, I certainly can't deny that. My life is rather... complicated..."
You looked at his figure and how the moonlight lit up his face. He seemed at ease for once. He was always on edge and planning ahead to make sure no one knew who he truly was.
"Well I'd like to learn more about you," You spoke up, "I'm at your side twenty-four seven, I think I have a right..."
Diavolo stopped in his tracks. He removed his arm from your hand.
"I think you're making a mistake by saying those words..." He said in a low tone.
"I don't think so," You said trying to sound determined, "Please!" You begged, "Let me know what's going on with you Diavolo, I'm the closest person you have!"
He pressed you against the wall of a closed storefront. His pointer finger made it's way down your face towards your chest.
"You have no idea what you're getting yourself into..."
You swallowed hard.
"Are you prepared to take the plung into the life of one of the damned?" He whispered.
You felt your face heat up as he stared at you intently. You could see in his eyes that he was deeply troubled, there was definitely something he was hiding from you, but after seeing his reaction, you were prepared to give him as much time as he needed to tell you. Your body seemed to react on it's own as you reached out to touch his face and console him. Instinctively, he shoved your hand away.
He must be scared...
You took a breath and tried again, this time you were a bit more forceful. He must've seen the determination in your eyes to get through to him because this time he didn't stop you. He was surprised by your touch, but quickly felt at ease. He leaned his head into the palm of your hand and closed his eyes. He looked so vulnerable before you, you never imagined being in a position like this with him.
"Let me help you Diavolo, not because it's my duty, but because I want to be there for you." You whispered.
Diavolo gently took your face in his hands. He was confused by these feelings welling up inside of him, he wasn't sure how to contain them. He looked at you before him, he thought of everything you had done for him in such a short span of time, how he admired your courage and strength. When he saw the guy flirting with you at the party and how he reacted the moment he dare laid a finger on you. It made him furious, he would've killed him instantly if there wasn't too many witnesses around... perhaps another time...
He didn't have much time to give it any more thought because you had met him the rest of the way and boldly placed your lips against his. Astonished by the interaction he thought that maybe he should push you away, but you took hold of his wrists as they held your face. It was like you were sending him a message telling him that it was okay and this was normal for him to feel this way. He followed your movements and eventually picked up rather quick. He pulled your body closer to his and moved his hands down the small of your back.
It was getting heated between the two of you and your knees were getting weak as he touched you and kissed your lips, cheeks, and then neck.
"Diavolo..." You gasped, "...Not here."
"Don't worry," He spoke, "I'll take us somewhere private..."
***
Diavolo pressed you down on his bed. You never dared step foot in his bedroom in fear he would be angry with you, but here you were. You weren't sure as to how fast you guys got there, it was probably due to Diavolo and his secrets. You hoped he wouldn't make you wait too long to tell you what was going on, but then again right now, that wasn't your main concern. His lips trailed your neck and went down towards your chest. You laid before him and ran your fingers through his long pink hair. You had never seen it down before, he always looked so professional around you, but at this exact moment, seeing himself like this was actually pretty sexy.
His fingers moved up towards the straps of your dress, he pried them away from your shoulders and let them hang on the sides. His was able to get the dress off quite easily (I mean he bought it so of course he knew how to get it off).
As you laid their bare before him, he took off his shirt. You always knew him to be buff, you happened to notice on multiple occassions when he just had a button up shirt on, but now seeing him like this was just conformation. He also had tattoos on his arms that you never had the chance to see either... God seeing him like this was almost too much...
He trailed kisses all over you skin, in some of your more sensitive spots he gave you hickeys. Your lips attached to his as his hands traveled up and down your body. Your hand went down towards his pants, you took hold of his erection that was rising against his pants.
"F-Fuck..."
You helped him out of his pants, and then his underwear.
"Whoa..."
He was a lot... well bigger than you expected.
Your fingers wrapped themselves around his erection, you began to make pumping motions with your hand. You literally had Diavolo wrapped around your finger, his facial expressions changed into pleasurable ones as you continued. He knew he was close but refused to let you have him like this. He moved your hand away and pulled your panties down. He placed his head between your legs and began to pleasure you with his tongue.
"D-Diavolo!" You moaned.
He kept going, he enjoyed how you gripped at his hair and held onto the sheets. Your facial expressions said it all, you were enjoying this all too much... But like him, this was not how you wanted to finish.
"P-Please," You begged.
Diavolo seemed to like seeing you beg, a devilish grin formed on his face as he wiped up his mouth and turned you over so you were on your hands and knees. He positioned himself in front of your entrance and forced himself in.
"A-Ahh! ~ " You shouted.
Of course it hurt to some degree, but Diavolo didn't waste too much time in checking to see if you were alright. He continued to thrust in and out of you until the pain became pleasure. You clenched the sheets as Diavolo took hold of your waist.
You kept moaning and gasping as he thrusted. He eventually pulled you closer to him he had one hand on your chest and another cupping just underneath your chin. He tilted his head into the crane of your neck and proceeded to lick your supple skin.
"(Y/N)..." He spoke, "I...I—"
You felt Diavolo release inside of you. Thankfully you weren't that far behind and you found yours as well. The knot delightfully unraveled in your stomach.
Diavolo panted as he pulled himself out of you. You laid your head down on the mattress with your bottom still in the air.
"You know," He spoke, "I wasn't so sure we'd get this far, but I'd be lying if I said screwing you wasn't on my list of things to do..."
"Oh yeah?" You breathed.
He laid down on the side of you and looked into your eyes.
"You're still not going anywhere, right?" He asked.
"What?" You asked still feeling pretty exhausted, "You think something like that would scare me away?"
He chuckled, "Can't be too careful..."
You laid on your side and caught your breath. Once you had come down from that experience, your first thought was of Doppio for whatever reason...
"Hey... Where the hell is Doppio?" You asked, "Did he make it back to the mansion?"
Diavolo laughed hard.
"What?" You asked directing your attention to him.
"I'm sure he's doing quite fine to say the least... He actually lost his virginity today."
You sat up in the bed, "Oh yeah? How would you know that? You haven't talked to him since he disappeared at the party..."
Diavolo smirked as he pushed a few strands of his hair away.
"Well... Let's just say he couldn't resist and wanted to come out and play during our little escapade..."