I'm going to choose regular because I want someone I can just live regular domestic life with and have no danger and drama but like...I might have him dress up in a mafia suit for a good time once in a while OKAYYYYY?????
summary | in this case, who is the lion and who is the lamb?
warnings | 18+ CONTENT TO THE MAX !
there are: mentions of weapons, drugs and mentions of potentially drugging someone (no actual drugging), loose descriptions and mentions of organized crime, brief mentions of potential murder and other assaults, oral sex (f. & m. receiving), unprotected sex, slight public oral sex, mentions and descriptions of dick pics, and anything else i may have missed
word count | 6.8k+
author’s note | yall…. yall…… i can’t believe this has come to life. just... enjoy the ride LMFAO - might make this a part two, i have no idea yet
this was 110% supposed to be for @fosterkidwiththebrokenjaw because i wanted to murder them w a jake smut and i didn’t tell them ANYTHING about what it entailed.. i did send a few sneak peeks in our nsfw writing chat on discord, but shit i think i needed this more than them lmfao
edited by the lovely, @screechesincoherently <3
BEFORE YOU READ, PLEASE REREAD THE WARNINGS AND ENSURE THIS IS SOMETHING YOU WANT TO READ.
Your father had been explaining to you the ways of his business for almost two years. In the two-year span, you had managed to learn the tricks of the trade. You had sat along the walls of meetings with various other gangs within the city – figuring out how everything intertwined and the reasons why everything was tied together. You studied each specific family, figuring out their members and their roles. It was another form of school for you, having notes upon notes surrounding you.
You figured out where your father’s exports came from – where your family had gotten any of the drugs, weapons, and money. Your family had close connections with a Colombian family who sold you cocaine to distribute, getting half of the profits your family made (although, your family lied about the amount, so it was more 40/60 than anything).
The Irish had a mass import of weapons that came religiously. The guns they provided could be linked to several murders of which your father ordered. The police would never be able to solve them though, the Irish are smart about their weapons trade. They had dealt weapons to your family for decades before another family had swooped in and stole their imports right out from underneath your nose.
Within those two years, you had also learned how to protect yourself. Hand-to-hand combat was something you excelled in, especially when it came to boxing and mixed martial arts. A few of the other soldiers within your family had adorned slings and bandages after fighting with you. Secretly, you thought they went easy on you since you were the boss’ daughter.
When you weren’t using your fists, your weapon of choice was always Chinese ring daggers. It was something you picked up on rather quickly – taking the life of someone with a blade was much more worthy than that of a gun. Although, you did happen to have a Desert Eagle 50AE that you happened to favor over any other gun you had been trained to shoot. Anytime you needed it, it was tucked away in your holster, itching to be fired.
With you having stayed within the dark for years, most people had thought that you had died. Your father turned cold some odd years ago, which is why most people had believed you to be dead. The only way a man goes that cold in such a short amount of time was because of a loss in the family. Which wasn’t an entire lie.
Your mother had been the one to pass away, taking with her your father’s humanity. Her death left him absolutely broken. While your father was working towards getting out of the business, he instead flung himself into his work. He worked so hard he became one of the top bosses within the city. There was only one family that rivaled your own.
The Kiszka family had been around for a long time. The family inheritance had been passed down from generation to generation. With Karen and Kelly Kiszka stepping down from power, the Kiszka twins have taken over. Their eldest sons, Jake and Josh, had been training for this their whole lives.
After gaining their Masters in Business, the twins were ready to take on what their father had left for them. The ruse their entire business was built on an auto body shop – which seemed a little too normal in comparison to who they were underneath all of the masks. The Kiszka’s under the microscope could be linked to various amounts of crime. After all, they were your biggest competitors in heroin trade. However, that wasn’t the target your father wanted to go after them for.
The first big deal in their reign was going to be a weapons deal with the Irish. And your father wanted in on that – wanted to usurp their guns from right under their noses just like they had done to your family some years ago. However, there was only a slight issue.
Your father had no idea what and when the deal was going down, but he knew it was sometime soon.
That’s where you came in.
Your job was to get that information from one of the twins – it didn’t matter who. When in the debriefing room, you found yourself drawn to one over the other. Jake Kiszka had a death stare that could kill a man and make women come on command. His twin brother did too, but he had nothing on Jake. Your mouth began to water at the sight of Jake, although you knew better than to think of it as anything other than a job.
David, your bodyguard in which your father assigned, was your getaway driver – however you needed him. The two of you had to come up with a plan together to gather the information you needed. If there was anything you had come to find out about Jake, it was that he loved beautiful women.
You, David and your father had gone over the plan almost a hundred times before the day of the operation. You were to go to the gala they were having which had been disguised as a fundraiser. While there, you were to seduce Jake and get him alone. Once you had done so, you were to knock him out via drugs or by the use of force and use his fingerprint or his facial identification to get into his cell phone where the information would be.
In and out. Simple as that.
The day of your nerves were nowhere to be seen. You smoothed out the material of your floor length dusty rose gown that hugged every part of your body just right, giving you the figure of an angel. With one last swipe of your strawberry flavored lip gloss, you left your room. The only sound you could hear in the hallway was your heels against the marble flooring. You felt powerful.
A swift left turn and you had made it into your father’s office. “You look absolutely beautiful, Dollface.”
“Thank you, Daddy.” You kissed his cheek with your own, not wanting to get your lip gloss on him. “Is David ready?”
“Just about, I believe,” he spoke, but was cut off with the sound of his phone ringing on his desk. He sighed begrudgingly and answered it. His voice was curt, making it known he was irritated with whomever called. “Jesus Christ. Fuckin’ put some bullets in his kneecaps til he talks. He knows something.”
You pulled your cell from the little golden clutch your father had gotten you on your sixteenth birthday. You scrolled through the text messages you had from various friends and other family members, pulling out David’s contact.
“You better come quick. I am not going to be late to this event.”
“You’re fashionably late to every meeting. You’ll be fine.”
You rolled your eyes at his message, about to put it back in your clutch before it pinged again.
“You just think the target is hot.”
He wasn’t wrong. Jake Kiszka was hot. There was no doubt about that.
The car ride to the venue where this was being held was a little longer than you wanted it to be, but it gave you time to make sure you had everything in order. Hidden within your clutch was a switchblade your father gifted you as a child. Your mother was not fond of you having a knife, but the look on your face of pure happiness had helped set her feelings aside. Everything else in there was mundane; a cellphone, lip balm, a compact mirror, and a pack of gum.
There were many photographers outside of the building, wanting to get a peek inside. You figured there would be a few inside, for publicity. The mayor had stood in front of you, standing with his wife and his two children as they got their pictures taken. You had snuck in through a side door, not wanting to be photographed.
The entire ballroom was decorated with light pink chiffon strung up against the walls and doorways. You swore that the attention to detail was very minimal – only effort being put in towards the stage where a podium sat and the tabletops had decorations sat in the middle of them, a small bouquet of white and pink roses.
A band sat towards the back of the room, playing lightly while everyone conversed and found their way to their tables. Your eyes scanned the entire floor looking for Jake, seeing if you could find him without needed to look for his twin too. You imagined the two of them wouldn’t be anywhere near each other – not needing to be for business purposes.
Your eyes finally landed on Jake, seeing him talking to the mayor. You walked over, grabbing a champagne flute from a server’s tray and took a sip. You licked your lips slightly, lip gloss smearing onto the glass. Jake’s eyes flickered to you as he noticed you walking towards him, continuing to talk to the major. You stood carefully next to them, patiently waiting for the right time to interrupt their conversation. “I hope I’m not interrupting anything too important.”
“Not at all. We were just discussing some detailing I need done on my car.” The mayor spoke, putting a firm hand on Jake’s shoulder. “Did you need to speak to him?”
“No, not really. Just wanted to do a bit of flirting before the whole thing starts, but I can always come back later.” You shot Jake a wink and began to sit down at one of the tables. You pulled out a compact from your clutch, using the mirror to look at the floor behind you in the general direction of where Jake and the mayor were standing. You couldn’t find him, which prompted a frown to form on your face.
“You wanted to flirt with me?” He asked, sitting down next to you.
“I did.”
“And why would that be?” He asked, putting his elbows on the table, searching for a motive within your eyes.
“Because I think you’re very handsome, Mr. Kiszka.” You took another sip from your flute, feeling the fizz on your tastebuds. Your eyes locked with his, seeing a slightly cocky smirk rise to his face. “Do you have a problem with that?”
“Not at all.”
The casual flirting between the two of you carried on through dinner, to which Josh and another one of Jake’s brothers had joined you at the table. You had learned his name was Sam and that he was very uninterested in his father’s business, being immersed in studies of the universe and its secrets. If it wasn’t for the mission in front of you, you would’ve actively tried to go home with Sam instead. You heard Jake whisper as you were busy asking the waiter for another drink, “Boys, she’s mine.”
The waiter handed you a double vodka and cranberry, placing it down in front of you while you thanked him silently. You turned back to the conversation, noticing the shift in tone between the three of them. It was almost as if they were competing for your attention. You easily slid the conversation through various topics, trying to focus on the other two rather than Jake. You noticed the way Jake’s patience wore thin. “I think it’s very interesting that you’re studying astronomy, Sam. I am a lover of space myself.”
“Are you? Do you have any other loves?”
“A few,” you started, a brief intermission to take a sip from your glass. “I have a passion for nature; geology is something I’ve thought about studying, but I have to take over my father’s company when he eventually retires, so it’s more of a hobby now.”
“What does your father do?” Josh asked curiously.
“Something boring. He hasn’t told me much, won’t let me know a single thing until I finish school.” You lied straight to their faces. Silently, you thanked the band as they began to play louder, making an idea pop into your head. “Would one of you like to dance with me?”
Just as Sam was about to say something to you, Jake interjected. He stood from his chair and extended his hand out towards you. “May I?”
You took his hand and smirked to yourself. You gave the boys a little wave over your shoulder, smiling to them before turning your attention back to Jake.
How fitting – the song that began to play as you and Jake made your way to the floor. With a hand in his, you turned towards him, your throat slightly becoming dry at the thought of being so close to him. “I put a spell on you.”
You looked up at him through your eyelashes, leg stretching out behind you as you slowly sunk lower. You could feel the stares from everyone in the room. It didn’t take much, though. The palpable tension between the two of you was probably one of the other reasons nobody could stop looking. You dancing with Jake alone was the first – he had never made public appearances with anyone. There had never even been any rumors of secret girlfriend or anything. Jake Kiszka had sworn off from dating – at least to your knowledge.
His hand was warm against the skin of your back, guiding you through the motions of the dance. You tried your hardest to keep your eyes off of him, but there wasn’t anything you could do about it. Jake was fucking pretty. So fucking pretty you could absolutely devour him right this second if he gave you the chance. “If you keep looking at me like that, my dear, I’m not going to be able to keep my hands off you. Or my lips, for that matter.”
“Whoever said you had to?” You asked pressing the lightest kiss to the conjunction of where his jaw met his neck. He almost stumbled on your feet, clearing his throat as he messed up. Your leg slid up the back of his teasingly. He inhaled deeply before he heard you speak into his ear, your voice laced with a taunting tone, “You’re getting sloppy, Mr. Kiszka.”
“I’m getting hard, angel.” He whispered into your ear through gritted teeth.
“I’m not really acting like much of an angel right now, sir.” You smirked to yourself, knowing full well Jake could probably guess your expression.
“No, but I bet your moans will sound heavenly when I wreck you later.”
“Would you like to go somewhere a little more private and find out?” He almost came to a complete stop, halting your dance. You could feel the vibrations of the wheels in his mind turning, pondering over the best course of action.
“And where would that somewhere be?” He questioned.
“I have a hotel room here tonight. Although, I’ll be quite frank. Someone as handsome as you could take me just about anywhere.” You whispered into his ear before you left him alone on the dance floor.
You knew he would follow you, which is why you were not shocked when you were pressed up against the elevator wall. His hands were firm on the sides of your neck, hips pressing into yours. With the sudden onset of kisses, you barely had any time to react, arms slightly flailing before you finally kept your arms at his waist, sliding underneath his jacket. You pulled his hips into yours, his lips separating from your own to let out a low moan.
“You’re gonna kill me, aren’t you?” He asked, keeping his hips against yours as his breath fanned over your face. You could still taste the champagne.
“Guess you’ll just have to wait and find out.” You whispered and pushed him off of you as the door opened to your floor. He was hot on your heels, waiting for you to open the door to your hotel room as fast as you possibly could.
The room in general was supposed to be used to put Jake in. If you were going to use drugs in order to knock him out, you were going to need a place to put him. Not to mention, you had studied the schematics of the building for a week in preparation – knowing where all of the cameras and exits were is crucial in missions like this.
The second the door was open his hand gripped the back of your arm and shuffled the two of you inside. Your back was pressed against the door, almost knocking the wind out of you. His tongue mingled with yours once again, hands firm as they held you – one at your waist and the other against the door. Your fingers tangled into his hair, tugging on the roots, pulling his head away from your own.
Your lips slid easily against his jaw, working your way to his neck. He breathed heavily as you licked a stripe up his neck, sucking his earlobe into your mouth, nibbling on it slightly. His hand traveled up your back, hand landing on your neck. He gripped the back of it tightly, pulling your mouth away from him much like you had done to him.
“I’ll get on my knees for you. Not to pray, but you will be worshipped.” He whispered against your ear, decorating your neck with open mouthed kisses, tongue soothing any skin that he bit. Your body shivered in anticipation as a groan fell from your lips. His mouth traveled south, leaving a trail of kisses in his wake.
Your hand flew to the back of his head as he began to kiss over your dress, right on your mound. The feeling of his fingers sliding underneath your dress was something you got used to very quickly. He pushed the material of your dress just enough where he could easily see your panties.
His fingers danced along the waistband. His fingers felt cool against how hot your cunt was – dripping for him, soaking your underwear. He hummed, his middle phalange brushing past your clothed clit, settling at the base of your cunt. He looped his finger into the front of your underwear, pulling them down your legs. He helped you step out of them, letting your dress fall back down.
You were about to ask him to unbuckle your heels for you, but you kept quiet upon feeling his lips against the inside of your knee. Your breathing became more and more labored as you felt his lips go higher and higher. Just as they were about to touch your dripping cunt, he hesitated – feeling his breath instead. He blew on your core intentionally, soaking in the way your breathing faltered.
You attempted to push your hips off of the door and towards his face. He simply chuckled at your action, using one of his hands to keep your hips from moving. He collected the bottom of your dress in his hands, thrusting them towards you, “Hold this for me, will you dear?”
You complied, keeping the ends of your dress tight against your torso. Your chest heaved in anticipation, wanting Jake to put his mouth on you, touch you – do something.
Your prayers would soon be answered by Jake’s tongue licking up your thigh. When his tongue had stopped, just next to your cunt, he began to suck and bite into the skin – leaving a nice little reminder of your time together.
His hands pinned your hips down as his tongue finally touched you where you wanted him. Your hand went to tangle itself into his hair, but his hand gripped your wrist. He threatened with dark eyes looking up from between your legs, “You touch, I stop.”
You nodded back to him, tilting your head back against the door as Jake resumed pleasuring you with his tongue. His tongue drew out moans that came from deep within your chest. His fingers dug into the skin of your hips, fingernails dragging down slightly. One of his hands strayed from your hips, knuckle brushing the inside of your thighs.
The minute he added his fingers into the mix, your head tried to press into the door even harder, but there was nowhere else to go. Your knuckles turned white as you held your dress so tight – not being able to touch Jake was torturous. One of his fingers slipped inside of you, a drawn out swear fell from your lips, “Fuck.”
You felt dizzy – so fucking lightheaded the closer you got. You were lucky Jake was underneath you; he was the only thing keeping you from crumbling to the floor. He had slipped in another finger; the added pleasure of another digit made your brain melt. Little whimpers slipped past your lips in response to being able to feel Jake smirking against you.
You couldn’t even comprehend what was waiting for you when Jake actually got to fuck you.
Your eyes squeezed shut so tight, all you had seen was a blinding white light. Your thighs began to shake, moans became louder and louder. Jake’s fingers moved faster inside of you, as did his tongue as it flicked rapidly against your clit. The hand that remained on your hip kept you sturdy against the door as your orgasm wracked through you.
His fingers began to slow, keeping a slower pace to allow you to ride out your orgasm on your own. He removed his tongue slowly, leaving sloppy kisses around your clit until he left one last one on your thigh. He waited until your breathing slowed to its normal rhythm before he pulled his fingers from your cunt.
He kissed up your stomach, pulling your dress from your hands. He let it fall to the floor as he put his knee between your two legs. The kisses he pressed to your cheeks were light, keeping you on Earth. Your head was in a daze – mind hidden deep within the clouds of lust you were currently swimming through. “You alright, angel? Didn’t wear you out too much already?”
“Are you gonna keep talking or are you going to fuck me?” Your voice was slurred slightly, almost as if you were drunk. You barely had anything to drink. If your memory served you right, you had abandoned half of a vodka cranberry back in the ballroom.
“So impatient.” He murmured to nobody in particular before walking the two of you back towards the hotel bed. He pulled down the zipper on the back of your dress while his lips occupied your own. You pulled away from him and sat on the bed as soon as your dress fell to the floor. You undid the buckle of each of your heels and slid them off.
You shuffled backwards onto the bed until your back hit the pillows. You watched him as he unbuttoned his shirt. You figured he was doing it slowly for your benefit. As soon as the shirt was slipped off of his shoulders, he threw it onto a nearby chair. Your eyes scanned and focused intensely on the skin that was now in the light of the hotel room.
You hoped to God your mouth wasn’t hanging open due to the fact that you were staring so hard at Jake’s body. You pulled your bottom lip between your teeth as you watched Jake remove his shoes and pants as well. It didn’t shock you when you saw Jake’s black boxers underneath his black dress pants – he was too predictable.
He crawled over to you, nudging your legs apart with his hand. He settled between them, running his thumb over your bottom lip. He looked down at your figure, how ready and open you were for him. Your legs hooked around his waist, pulling his hips into yours. His moans were beautiful, as soon as his clothed cock hit your cunt. Your hands pulled at the back of his neck, tugging his lips towards your own.
You wasted almost no time, the hunger for his cock inside of you was driving you crazy. Your body burned for his touch, to feel him fill you up. One of your hands traveled away from his neck, sliding down his torso before rubbing his cock over his boxers. He pulled away from you, heavy breathing, “You want it?”
“Mhmm.” You spoke, slipping his boxers down his legs slightly before you pulled him out. You brought your hand to your mouth, collecting some of your spit in your palm, beginning to jerk him a little. He let out a soft groan into your neck.
“Where do you want it angel?”
“I think you know where.” You whispered back, brushing the tip of his dick through your folds.
“Fuckin’ perfect.” He muttered underneath his breath as he began to insert himself into you. You through your head back slightly at the sensation, already loving the way he felt. Once he was fully sheathed inside of you, he pulled out halfway and slowly pushed back into you once more.
“You don’t have to be gentle, sir, I won’t break.”
“Careful what you wish for.”
As soon as those words left Jake’s lips, his pace became relentless. His teeth sunk into the skin on your shoulder, muffling himself. Your hands occupied Jake’s hair, tugging and pulling in an attempt to get Jake as close to you as possible. You tried to keep your curses to yourself, but it was almost impossible.
He hooked one of your legs over his shoulder, keeping the other one at his waist. You let out a screamed with the change of position, not meaning to be as loud as you were. Jake brought a hand up to your mouth, leaving enough room below your nose for you to breathe out of. He fucked into you, hard and fast.
Tears of intense pleasure threatened to spill from your eyes, loving every single second of Jake filling you completely and then taking it all away – only to be whole again a split second later. You surely were becoming dizzy as you were before, but this was a whole other level.
Fucking Jake was something else. Compared to all the other people you had slept with before, they were no match for Jake. He hit the places within you that would forever be tied to your soul and engraved in your brain. You didn’t think anyone in this world would be able to fuck you the way Jake was. “Holy fuck, Jake, right there.”
Your hand slid between the two of you, fingers circulating your clit rampantly. The familiar orgasmic haze was beginning to set within you, the knot within your lower belly grew tighter and tighter. Your cunt spasmed around his cock, making him moan into your ear. “Shit,” he spoke through gritted teeth and furrowed eyebrows, “I’m gonna come, fuck. Where do you want me to come?”
“Anywhere, Jake, I don’t fucking care,” you whined. “I’m so fucking close.”
The second your orgasm hit you, it felt as if though you were transcending through time – all of your senses blurred together. You could hear colors and see sounds. You could feel Jake pull out of you, jerking himself until he spilled onto your stomach. He slid to one side, catching his breath. “Let me grab a towel, quick.”
You didn’t expect him to wipe his come off your stomach. It didn’t seem like he was one of those people, but Jake was full of surprises.
He slipped into the bathroom and began to run the shower. He asked if you wanted to join him, but you just stayed stayed in the bed, telling him you’ll be fine. You pulled his button up from the chair, threading all of the buttons through their respective holes. You searched through Jake’s jacket pocket and found a pack of cigarettes.
You unlocked and slid the door to the balcony opening, stepping outside as you had Jake’s pack of cigs in your hand. You pulled one out, putting it between your lips as you lit it up.
You sat in one of the chairs on the balcony, waiting for him to join you from the bathroom. Cigarette betwixt your fingers, you sit there in his button-up. All you needed him to do was go to sleep – that was it. If he fell asleep, you could put his fingerprint into his phone and get the information you needed for your father.
This certainly wasn’t part of the plan – having sex with him.
“I almost thought you had left already.” He spoke, bringing you away from your thoughts.
“And miss out on round two?” You smirked up at him, licking your lips as you looked at him fresh out of the shower. His hair was wet, water droplets falling onto his chest and back. You take a drag of your cigarette. “Not a chance, Jakey.”
“Who said there would be a round two?” He asked, leaning against the frame. You put your cig out on the ashtray on the small table next to your chair. You stood in front of him, putting a hand on his abdomen.
“I was hoping for round two.” You looked up at him through your eyelashes, sinking down to your knees. You were thankful he decided not to put his dress pants back on, leaving him in just his boxers. His hands collected your hair and held it within his fist, using his teeth to slip the hair tie he wore on his middle finger off. He wrapped the hair tie around your hair, the messy bun he had given you had already begun to tilt to one side.
The second your mouth wrapped around him after removing him from his boxers, he hummed in appreciation. Your tongue swirled around his head, before you took hold of him and licked up the underside of his cock. He groaned, pushing his hips forward a bit as one of his hands found your hair. You taunted him with his own words, spitting them back at him with a cocky smirk, “You touch, I stop.”
“Cheeky.” Jake gave you a fake smile. It was quickly wiped from his face by your mouth wrapped around his cock once more. His eyebrows pulled together the second his tip touched the back of your throat. Tears pricked at your eyes and you tried your hardest to keep it together. Today was not the day where you particularly wanted your gag reflex to act up.
You breathed in and out through your nose, trying to focus on the way that Jake looked. You loved the way that Jake looked while painted in pure bliss. His mouth hung open slightly, chest heaving, tongue swiping over his bottom lip much like his tongue did to yours earlier. “Jesus fuckin’ Christ.”
His fingers threaded through your hair’s terrible bun, tugging at the roots of your hair. You hummed around him, knowing that he had lost whatever game it was that the two of you were playing. You pulled your mouth off of him, smirking as you wiped some spit from the corner of your mouth with your thumb, “You touched me.”
“Fuck, love, come on. I’m almost there,” he spoke hurriedly, replacing the feeling of your mouth with his hand as best he could. “Please, please let me finish.”
“Nobody ever said you couldn’t come in my mouth, Jake, I just told you that I would stop touching you.” You winked at him, watching him finally connect the dots. He aimed his cock towards your open mouth, jerking his dick until he felt the urge to come. His breathing truly faltered now, being able to audibly hear it from your knees.
“Fuck, I’m gonna come.” He spoke lightly, huffing as his salty come finally touched your throat. The groans that came from him were stored in a secret part of your brain that would only come alive in the night time – as nobody is around you, with a hand in your underwear thinking about Jake.
You had stood up from your knees, walking past Jake to go inside. You removed Jake’s button up, climbing into bed. The sheets felt so comfy wrapped around you. Jake collected himself and shut the sliding door behind him, locking it. You felt him slip beside you, wrapping an arm around your middle. “Would it be too much to ask you to get breakfast in the morning?”
“You already know how this will end, Jake,” you whispered, brushing a finger down the slope of Jake’s nose. He didn’t seem so scary close up – neither did any of his brothers. Maybe that’s why they could get away with so much. “They always end like this.”
“I suppose they do. Although, I was hoping you were going to be more than a one-night stand.”
“I’ll see you again someday, Jake. This will not be the last time.” You lied through your teeth. You had no intention of seeing him after this. Mostly because you knew deep down that seeing Jake again could very easily mean that a hit would issue for you. He’d eventually find out that you had stolen information from him. He’d trace back the ambush to you and your little ruse.
You had waited until his breathing fell under the guise of sleep. You slid out of the bed easily, being careful not to wake Jake. You grabbed his phone from the bedside table, looking to see if it was a fingerprint phone or facial recognition. You held the phone up to his face, hoping to God it would go through although he was sleeping.
Once it unlocked you scoured through his messages and contacts. You found the information you were looking for and took a quick picture of it. You were curious as you held Jake’s unlocked phone in his hand. You quickly swiped out of the Messages app and landed on his Photos.
You scrolled through all of them, seeing various pictures of him and his brothers doing various things; a few pictures they were all sporting cigars, some of them had beers in their hands and in some of them they held both. The pictures that really intrigued you were the ones of just Jake – phone held out as he took a mirror selfie of him naked.
His body looked as it did before you, fit but not too much where any abdominal muscles were defined. The picture in itself was better than any of the dick pics you had ever gotten before. His face was like stone, giving barely an expression as if he took it without any effort; as if he hadn’t taken and retaken this picture a hundred times – keeping this one, and only this one from all the ones he had originally taken.
His cock was pretty, standing tall with arousal. You swiped through the photos, hoping that there was a series of them behind the one you landed on. And much to your approval, there was. In the other photos he had, a firm hand was wrapped around his cock, the veins in his hands protruding – which caught your attention right away aside from how pretty his cock was.
Next there was a video of which you played as soon as you were out of earshot. You turned the volume up on his phone slightly, making a mental reminder to turn it back down before putting it back on the nightstand. His breathy moans sounded familiar to you, having just heard them yourself. He was fucking ethereal as he came, cum dripping onto his hand before the video ended just after you had heard a low “fuck” come from Jake.
Before you went any further, you returned his Photos to the main menu, locking it before you put his phone back exactly where he left it on the nightstand. Your breathing was heavy and you swallowed thickly, crawling underneath the covers next to Jake. He had felt the dip in the bed you had created, pulling your body close to his as he turned around.
You let sleep overcome you until the morning when you woke up before Jake. You thanked your lucky stars and carefully removed yourself from the bed. Somehow, within the night, Jake had ended up pulling you completely on top of him in his sleep. You definitely slid off of him when you realized what position you were in.
The insides of your thighs ached as you stood up from the bed, but you put the thought and the pain aside to hurry the fuck up, and get the fuck out of there. You found your dress on the floor and pulled it up your body and zipped it to the best of your ability.
You pulled the little notepad that belonged to the hotel from the desk, and with the hotel pen, you scribbled a little note onto it. The note you wrote was a quote from someone you couldn’t remember the name of, “One night stands are like chess, only the loser demands a rematch.” You had also mentioned that you would see him again (for his benefit) with a little wink in your cute, slightly boyish handwriting.
You left it by his cellphone and looked around the room for your shoes. Once you slipped on your shoes you threw your hair up into a bun to get it all out of the way.
With a single text to your phone, David had let you know that he was outside waiting for you. David sat in the driver’s seat, impatiently waiting for you to make your way to the lobby. You hopped into the back of the SUV and immediately removed your shoes as the door closed. “Did you get the information?”
“Good morning to you, too, David.” He rolled his eyes and huffed out disappointingly. “Yes, I know where the drop is gonna be. I took pictures of his messages, I’ll let father know.”
You slipped the straps of your dress down your arms. Slipping on an old university sweatshirt, you dialed the phone number for your father, letting it ring. With the phone between your cheek and your shoulder, you shimmied on a pair of athletic shorts.
“Hello, Dollface.” He answered affectionately.
“Hi, Daddy. I got the information you wanted.” You smiled, taking the phone in your hand. “I’ve got it all on my phone.”
“That’s a good girl. You want in?” He asked, already knowing your answer. You giggled into the phone, confirming his suspicions.
“You know I do.”
“You’ve got it. As soon as you get back, we’ll have a meeting with the team. Okay?”
“Okay. I’ll see you when I get back. I love you.”
“I love you, too. Bye.” David sneered as soon as you hung up the phone call with your father. You gave him an inquisitive look.
“I can’t believe you fucking slept with the target.”
“I did what I had to do to get the information from our target, David. It doesn’t matter how I got the information, all that matters is that I got it.” You climbed into the front seat from the back, managing to not kick David in the face. “You couldn’t have picked a different vehicle? My dad has like twenty.”
“Why would I pick a different car?”
“I don’t know... I feel like it looks super fucking suspicious having me get into a black SUV leaving the hotel in the dress I wore last night. Most Uber’s are just... normal cars.”
“This is a normal car, Y/N, I don’t get what you mean.”
“Okay, whatever. Doesn’t matter anyways, we’re twenty minutes from home.” You pulled out your phone and scrolled through various social media sites until you were safely back in the driveway of your home.
***
Your father had gotten the shipment of guns that was meant for the Kiszka family. It had was the second mission you had ever been allowed to be on without your father present in any way, shape or form. You walked around the house like top shit after that.
Weeks later, you had gotten an invitation to a meeting with your father and the Kiszka family. You had swallowed thickly before walking into the restaurant your father had told you to come to. It was a sweet Italian place that had been open for years – the family who owned it originating from Italy.
You straightened up your posture, walking over to the table with false confidence carrying you. He looked up from the restaurant table, finally looking at something other than his phone. He was met with your gaze, to which his eyes opened wide. His lips parted slightly while his tongue brushed over his bottom lip. He stood from his chair, extending out his right hand. “We meet again.”
“I told you we would.” You slipped your hand into his and watched closely as his lips pressed a light kiss to your knuckles.
Story No. 3 of my Season 7 Countdown Project! Also: I’m still taking prompts for future missing scene fics.
Summary: “My time undercover in the mafia was actually kind of lame. I mean, I wanted it to be badass, but I'm good at computers, so I mostly just helped them switch over from AOL.”
The story of how Jake became the mafia’s IT guy. Takes place during Undercover. (Read on AO3.)
What he doesn’t tell any of them, after he’s back, is that going undercover with the mafia is mostly just- really lonely.
Jake spends most of the first week alone in the crappy one-bedroom the FBI hooked him up with in Bushwick, waiting for one of the Ianuccis to get in touch. At night he lies awake on his mattress on the floor, mustard-yellow streetlight glaring through the grimy bedroom windows, and thinks that he’s already failed his assignment, that he couldn’t pass himself off as a disgraced cop for even one night. (The irony does not escape him.)
Then a guy calls Jake’s burner at 3 in the afternoon on the sixth day, and he introduces himself as Derek and says he’s downstairs. It’s now or never. Jakes takes a deep breath and blows it out hard, then steels himself and heads down. By the end of the week, he’s got a pierced ear and a gold-chain necklace and a cigar burn on the back of his neck, just below the collar of his new silk shirt. Years ago, before he’d gotten into the Academy, Jake had thought about getting a tattoo (“yippee ki yay” in calligraphy, very classy) in that spot and he’s grateful now that Gina talked him out of it. The burn was an initiation, and it didn’t hurt as much as he’d thought it would, but the scab is itchy and sometimes when he thinks of the smell of it he gets a little nauseated.
Leo Iannuci sends him out with Derek on a couple of jobs – mostly picking up cash from people they’re extorting from, but sometimes they’re the ones making the threats and Jake hates that part, hates it so much. Derek’s a nice guy, an Academy dropout who seems to shed his tough-guy attitude with his velour jacket every time they leave a bodega or laundromat or some other business where he’s had to smack someone around. Derek always does the hitting, never makes Jake do it, and Jake can’t decide if it’s because he likes the violence or if he just senses that Jake really, really doesn’t.
Either way, he’s grateful, and he has to keep himself from feeling too much fondness for Derek just because he protects Jake from the dirty work. Jake’s gotten that talk from the FBI: It’s natural to think you’re making friends, making connections, they’d said. But you’re not. Don’t ever forget that. Jake is always, always on his own.
About a month in, Jake is at Leo’s penthouse in Flushing, reeking of cologne that one of the Sals had doused him in while another Sal held him down, when Leo swears loudly and slaps the side of his computer, a rickety old desktop with a fan that sounds like it’s working triple-time.
“Motherfucker, it won’t let me fucking update!” Leo slams his fist down on top of the harddrive.
Jake looks around the room but everyone else suddenly seems to have important business on their phones, so he approaches Leo and says, “What’s the problem?”
Leo snarls at the computer. “I had to add some new clients to the ledger and now this son of a bitch won’t save the changes.”
Le’s “clients” could mean extortion victims or dirty cops or assassins-for-hire or any or all of the above. Jake hasn’t seen the ledger yet – he wasn’t actually sure there was one before this moment.
“You want some help?” he says, casually.
Leo finally turns his glare to Jake, staring him down long enough that Jake has to fight to keep from shifting on his feet and curling his hands into fists. “You any good with this shit?” Leo says.
Jake shrugs. “Yeah, I know computers.”
“All right, have at it,” Leo says, and gets up from the desk.
Jake sits, and Leo grips his shoulders, sudden and fast, fingers digging hard enough to bruise. And then just as suddenly he’s let go. He stays behind Jake, though, watching him click through open windows to find the source of the problem. It doesn’t take long.
“You’re using AOL,” Jake says. His voice sounds a little strangled to his own ears.
“Yeah, I guess,” Leo says. “So what?”
“So that’s your problem,” Jake says.
Jake’s definitely not an expert at computers, but he’s always had an affinity for the basics and it only takes him a few minutes to fix the immediate problem – an outdated file type that the desktop won’t recognize anymore. Jake saves the document, which, infuriatingly, is a table someone made in Microsoft Works. It’s so horrifically formatted that Jake can’t help but imagine the devastating stroke that Amy would suffer if she even knew it existed. She would seriously start bleeding out of her eyes.
Later that night, Jake smokes his first full cigar and convinces Leo to let him move all of their documents to a Google drive. By the end of his first full month undercover, Jake’s become the mob’s IT guy. It’s exactly as dope as it sounds. (It’s not remotely dope.)
+++
It takes him a couple of weeks to transfer everything to the cloud; he has to carefully rebuild all of the ledgers in proper spreadsheets. Leo assigns one of the Sals to keep an eye on him, but after the first hour Sal gets bored and retires to the couch to play Kwazy Cupcakes on his phone (the sound effects touch off a profound homesickness that Jake tries his best to ignore). So Jake has no trouble copying the ledgers onto a thumb drive that he later passes on to his handler. It’s almost all the evidence they need. Then it’s just a matter of waiting for the FBI to get its teams in place, to mark the right time and place to take down the biggest targets.
Jake does a few more jobs with Derek, and he just misses getting sent on a drug run that ends in a shootout and two of Iannuci’s guys in the hospital (Jake was back at Leo’s penthouse trying to figure out why his computer suddenly refused to talk to his printer). He knows he’s dodging literal bullets, but that doesn’t mean he sleeps well at night, or that his nervous system doesn’t light up like a Christmas tree every time someone racks a gun near him (which is pretty much all the time – mafia guys love cleaning their weapons).
Jake ends up giving a seminar to half a dozen Iannuci men (plus two women) on file encryption and two-step authentication and he feels a little guilty for teaching the mob how to evade hackers – some of whom will surely be cops – but weirdly, he’s starting to get bored, and he figures none of them are going to remember any of his lessons anyway.
The night before Marco and Angie’s wedding, Jake gets super drunk with a bunch of the guys and he sings “The Longest Time” with Derek, slopping rye whiskey all over their polyester shirts. The next day Jake’s going home. But that night, for the first time in 62 days, he forgets to be lonely.
End Notes:
Title is from Feed the Beast (Bash Brothers).
I know there is a lot of mafia-Jake fic, and that this take is not like the others. But I always thought Jake’s comment to Pimento about what he really did undercover was interesting and worth exploring. I don’t think it means the job wasn’t dangerous or super stressful for Jake, though my version is probably less so than some of the more violent takes some writers have offered (which are just as valid!).
I couldn’t decide if this story should be considered a missing scene for Undercover or Adrian Pimento. It fit better here for obvious reasons, but the revelation is in the later episode. But really, it doesn’t actually matter.
My darling beta @fezzle wisely pointed out that Jake the Computer Wizard doesn’t exactly fit with what we learn about him in Ticking Clocks. My solution/answer to this is that Jake is actually pretty good with day-to-day computer stuff (there’s quite a bit of evidence of this in canon – or at least, evidence that he’s not BAD with computers), but hacking-level stuff is way over his head. That’s why he starts Ticking Clocks full of bluster with the so-called security expert and then eventually has to admit he doesn’t know what he’s talking about. Unfortunately, what he actually says is “I don’t know anything about computers.” That could be the writers just forgetting their own canon, but I choose to believe that it actually fits just fine with Jake’s “I’m good at computers” in Adrian Pimento. It’s all about context!
