#And then he realizes one day hey that's not cool. What they're doing to Jimmy is not cool. And that that includes him too

[tubbytarchia]

Hey so, funny thing happened

hey what if I cried

[robert-de-niro-only-fans]

Escape

Jimmy Conway x Paulie's Daughter! Reader

Hiiiii, this fic is a little surprise I've been working on and I've got a few others in the works. I hope you guys love it! ❤️

TW: smut, mentions of crime and crime families, murder, marriage, mentions of pregnancy

Word Count: 5.2k

As you stand in front of the mirror, your head spins from the morning you've already had. Women everywhere, whizzing around you doing your hair and makeup, getting you into your wedding dress. All that to make you a bride.

And you do look like a bride, you think as you stare into the mirror.

Behind you, you hear a familiar voice, "Ahem, ladies, could I get a moment alone with our bride?" Jimmy. He's being extra charming today, as many of the women left the room giggling because he spoke to them.

"Wow... (Y/N), you look gorgeous..." he creeps up behind you and delicately places his hands on your sides, as if he might break you. He looks at you in the mirror, before gently placing a kiss on your shoulder. "You're gonna stop traffic when you walk down the aisle. I can't wait to see it," he moves your veil and hair to give you a kiss on the cheek.

You don't say anything, just stare into the mirror. After a small pause, Jimmy turns you around, "Hey, you alright?"

Finally, you get a good look at him in his tux: all black with an off white shirt and a deep green vest peaking out from the lapels of his tuxedo jacket. You let out a breath you didn't know you were holding, "Yeah, I'm okay, just nervous," you put your hand on his chest, looking him over again, "I'm glad you're here. You always calm me down, and you look great by the way."

You knew it was an unconventional choice, but you wouldn't have picked anyone else to be your Maid of Honor. And Jimmy was happy to do it for you, even with Tommy and Henry making fun of him for it, at least until they got asked to be bridesmaids.

These were guys that in another life, you never would've been friends with, probably wouldn't have even known. And truthfully, your dad didn't want you being friends with them, because he knows what they are: criminals, nothing but criminals. But they're the only family you have, and Paulie had to admit that it was so cute seeing you get into trouble with Henry and Tommy and then go to "Uncle" Jimmy to get you out of it.

Jimmy wouldn't have done that kind of thing for the guys; they needed to get pinched and learn what it was like, but he would do anything to keep your pretty face out of jail. Since you've grown older, old enough for your father to let you get married, you and Jimmy have grown to be best friends. He's not so much the Uncle he used to be to you.

"(Y/N)?" Jimmy starts, "we got something to tell you, honey."

Just from the man's tone of voice, you can tell something is terribly wrong; you just know him too well. At that point, Jimmy opens the door, and Tommy, Henry, and your dad Paulie shuffle in.

"What's going on?" you say sheepishly, taking a step back from the men before you.

"You may wanna sit down," Jimmy motions to the little couch in the room.

Your dad reaches for one of your hands and you pull it away, "What is it, papa?"

"Sweetie, let's sit down, so we can talk," he places a hand on your back, and you both sit on the couch together. Jimmy, Tommy, and Henry all stand around looking like tough guys: arms crossed, keeping an ear out for anyone who might be listening outside the door, their faces looking stone cold with a bit of worry in their eyes.

"(Y/N), that guy out there," Paulie starts, referring to the groom waiting to marry you, "he ain't the guy you think he is."

"What?" you ask quietly.

"Well, uh, the guys here-" he looks up at the three men standing around you, "Jimmy, uh..." He just couldn't say it to you.

"We've been keeping an eye on this guy, scoping him out," Jimmy finishes for Paulie.

"What? You were spying on my fiancé?" you ask, feeling hurt.

"You didn't think we was just gonna let you marry anyone, did ya?" Tommy pipes up.

"And I'm glad we did," Jimmy cuts back in, "that guy out there, (Y/N), he's a liaison for another crime family! They were using you for information, and now he's able to identify all of us."

"What? No... He's- he's... a union rep," you cast your eyes down as it dawns on you; it was all a lie and a great cover up so he could talk about his friends and you wouldn't even realize. God, did you feel stupid. If anyone was gonna catch him in that lie, it should've been you. "I'm so sorry..." you whisper as tears drop down onto your wedding dress.

Paulie immediately pulls you into a hug, "Hey, hey, it's okay, baby girl. It's okay. The guys here have a plan." He tries to comfort you as you cry into his shoulder.

"I'm so sorry, you know I'd never try to put any of you in danger. I'm sorry I was so stupid!!" You feel horrible and angry with yourself.

"Shhh... You gotta keep your voice down, honey," you feel Jimmy's hand rubbing circles into your back as he kneals next to you. "You're not stupid. It took us a long time to crack this guy. He covered his tracks well."

You turn to Jimmy, tears mixed with mascara running down your face. "Hey..." he says, pulling out a handkerchief and wiping the tears from your face, "Don't cry, angel. You shouldn't cry on your wedding day."

"But-" you get close to him, "it's not my wedding day anymore."

"Still," he pulls you up off the couch and into a hug, "you look too pretty to cry, and besides, we gotta get going."

You give him a confused look, trying to get it together, "Get going? Where are we going?"

"Well, uh, you and I are going on your honeymoon; Tommy and Henry know the rest of the plan."

"Honeymoon? We're not gonna cancel it?" you question.

"Listen, sugar," your dad grabs your attention, "this is the one day we can get your fiancé alone. He didn't dare bring any of his associates; we would recognize them, especially after all the recon we've done. So Jimmy's gonna sneak you out of here, and you're gonna go away for a while, and we're gonna get rid of this crook and tie up all the loose ends."

Just a few moments later, Tommy and Henry go back into the church to make it seem like everything is normal. No one is gonna think anything of Jimmy and your dad being with you, because that's the order the ceremony will go in. Your dad waits out in the hallway, as if he's waiting for you to put the last few finishing touches on your dress, and as everyone clears the hall to go to the church, he signals to Jimmy that it's time.

You and Jimmy quietly sneak out of your dressing room to head to the car. Before you run off, you turn back to your dad, giving him a big hug, "Please be careful, papa. I love you so much, and I'll miss you."

"I love you, too, (Y/N)," he gives you a kiss on the forehead, before you turn to head out the back hallway of the reception hall.

On the way out, Jimmy grabs a huge plate of hors d'oeuvres and holds the door open for you. You make your way out to this random convertible (probably stolen), seeing your suitcase in the backseat.

"Mines in the trunk," he lets you know, before setting the plate of food in the back and helping you in the car. Seconds later, you're peeling out of the church parking lot.

• • •

You and Jimmy can't help but laugh as you get further and further away from your wedding ceremony. You can't explain why you're laughing so hysterically, but it feels like old times getting into trouble with Jimmy. Plus, it's a welcome distraction.

"Jimmy," you interject the laughter.

"Yeah?" he asks, coming down from his laughing fit. You've already reached the highway heading from upstate New York into the city to get to the airport.

"Jimmy, I gotta get out of this dress," there's a serious tone in your voice that tells Jimmy this is more urgent than you let on.

He quickly whips out his switch blade, "Okay, lean forward." And then you feel the cool metal of the blade grace your back as he cuts the ribbons corseting your dress.

The dress loosens around you, and you look over at the man, "Thank you," is all you say before sliding the dress down over your hips, then throwing it up in the air, letting the wind take it down the highway. Jimmy has an impressed look on his face as he glances at you with a half smile on his face.

He reaches over, placing a hand on your bare thigh, pulling your wedding garter down your leg before holding it above his head and spinning it around like a lasso. "WOOOOOO!!!!" he yells at the top of his lungs as he flings the little piece of lace. Anything to make you laugh, and it does get a rise out of you.

There's a pause for a moment as Jimmy takes in the view of you in your white lingerie; his eyes don't linger for long though, because he doesn't want to make you uncomfortable.

Though, you can't help but feel sexy for moment before climbing into the backseat to change.

"Hey, bring that food up to the front seat when you're done," he says, looking at you in the rearview mirror. You smack his shoulder, realizing he can see you changing. He chuckles and flips the rearview up. You spend the rest of the trip leaning on Jimmy and snacking on the hors d'oeuvres on the tray, until you arrive at the airport.

Because you skipped the wedding ceremony and reception, you arrive way earlier than you're supposed to, but it's no issue, Jimmy already worked it out by moving your flight up. It also works out better, because there will be goons at the airport looking for you, but by the time they get there, you and Jimmy will already be gone.

• • •

After a few hours when you arrive in the Bahamas, Jimmy gently runs his fingers through your hair to wake you up from your nap. You were conked out on his shoulder, exhausted from this morning. "C'mon, sleepyhead, let's go have a honeymoon," he helps get you up and grab your bags.

"Mmmm," you yawn following him, "you say that like it's your honeymoon or something."

"Well, it is now," he chuckles, grabbing your hand to lead you off the plane. After a warm welcome from some locals at the check in desk, you head over to your private villa, right on the beach. Even though it's already dark, the island is beautiful. The warm breeze makes the palm trees wave; the sand is soft under your feet; and the sound of waves crashing is seriously so relaxing.

Inside your villa, it looks so cozy and clean, and you're so ready to get some dinner and go to bed. That's just what you do. Jimmy calls the office to order dinner to your little beach house, and you pop into the bathroom to take a shower and change.

By the time you're done, dinner is too. Jimmy greets you with a little side hug and pulls your chair out for you to sit down at the table. "Comfy? In your little robe and all?" he asks, eyeing you up and down quickly.

"Mm-hmmm," you moan, stuffing your face with delicious food. Jimmy chuckles at you before doing the same.

After getting your bellies full on tasty seafood, you decide that it would be a good idea to go to sleep, that way you can make the most of your time on this lovely island.

As you and Jimmy make your way to the bedroom, you're met with a reminder of why you're there in the first place: rose petals and candles littering the room.

Jimmy sees the way you pause, "Do you want me to get rid of this stuff?"

"I- uh, no... It's okay," you look back and forth between him and your bed.

"Here," he says, leading you to the couch, "Stay here."

He goes into the bedroom and closes the door behind him. For a few moments you hear huffing and thudding as he blows out candles and throws them in the trash, and you hear his arms hitting the bed as he wipes the rose petals away. Jimmy exits the room with a trash bag in tow, tossing it out on the front patio before returning to the living room, breathing a little heavy, and holding his arm out, motioning you to the bedroom.

You stand up and put your arms around him, giving him a soft kiss on the cheek, "Thank you, Jimmy."

He places his arm around your waist and presses a cheek to your head, "You're welcome, sweetie. Now go to bed."

"You're not coming?" you ask.

"I'll sleep on the couch. You have a good night, and sweet dreams," he gives your arm a squeeze before heading to the bathroom to get ready for bed.

As you settle into bed and try to sleep, it sinks in. Your relationship that you'd been so happy in is over... And here you are in another country for an undetermined amount of time while your ex-fiancé gets "taken care of." Even though his intention was to hurt you, you can't help but mourn what feels like the loss of your happiness. In fact, there's only one place you can feel happy right now, and you won't sleep until you're there.

"Jimmy?" you whisper through your sniffles. You stand before him as he sleeps soundly on the couch. "Jimmy?" A little louder this time, and that does the trick.

The man takes in a sharp inhale through his nose and his eyes pop open, "(Y/N), hey," he rubs his eyes, "you okay?" You just stand there quietly sniffling, and then Jimmy sees the redness in your face, "Hey, hey, c'mere honey, c'mere." He holds the blanket up for you to climb in, and he immediately wraps his arms around you, cuddling you in his cozy little spot on the couch. You simply bury your head into his chest, and let out a few tears. "Shhhh, shhh," he says as if cooing a baby, "it's okay, I'm here, everything's gonna be alright."

• • •

The sun brightly lights the whole open floor plan of your beach side escape, warming you and Jimmy in your bundle of blankets. You awake to the feeling of his fingers lazily combing through your hair, and when you crack your eyes open, you see him happily smiling down at you. You place a hand on his chest, and he covers it with one of his own, giving your fingers a squeeze.

"Morning, you hungry?" he greets you.

"Mmmm... Good morning, sweet man," you happily nuzzle into him.

He cups a hand on the back of your head, "Whaddaya say we get some breakfast, then ya wanna go swimming later today? Hm? We got that beautiful beach right out there." His head motions towards the large glass doors that look out onto the sand and sea.

"Only if we can stay here a little longer," you hum into his chest, perfectly content with just cuddling up to him all day long.

"Okay, princess, we can stay a little longer."

• • •

After a relaxed morning (yes, you both dozed back off to sleep for a while) and a nice breakfast of fresh fruits, juice, and pastries, you wait on the back patio for Jimmy to change into his swimsuit. When the sliding glass door glides open, you turn and see the man in swim trunks that hit about mid-thigh, short sleeve button up shirt that's unbuttoned, a gold chain, and a cigarette. Of course Jimmy dresses like that for the beach.

"Whaddaya think? How do I look?" he jokes at you.

You walk over and places your hands on his bare chest. "The view looks pretty good from here," you chuckle lowly.

Jimmy grunts, "You better watch those hands of yours," he warns, moving you off his chest before lightly taking your fingers in his. "Alright, let's go," he says, leading you towards the waves.

"Ya know, uh," Jimmy catches your attention.

"Hmm?" you chirp, hand still happily in his.

"How come you're still wearing this?" he asks, holding your hand up, and tapping his thumb on your engagement ring.

"Oh... um... I'm not sure, honestly," you look down at your hands, wringing them together and fidgeting with the little piece of jewelry. As you take your first few steps into the ocean, you slip the ring from your finger. "I guess it doesn't mean anything anymore," you ponder to yourself before chucking it into the water.

Jimmy raises his eyebrows in surprise, "You didn't wanna sell it?"

You turn around and pat him on the chest, "I know you and the boys back home will make me more money than that ring is worth. It wouldn't surprise me if it was fake, knowing what I know now."

• • •

Time got away from you as the two of you enjoyed your day in the sun. After walking along the beach and Jimmy dunking you in the waves a few times (don't worry, you got him back), it's already early afternoon. And boy, were you beat.

"Hmmm, I think it's time for a nap!" you yawn, "This sun has got me drained."

"Wanna go inside?" Jimmy points to your little beach house.

"Yeah, but I don't think I can walk another step," you whine playfully, giving the man puppy eyes.

There's a long pause as Jimmy gives you a serious look, but he's only kidding. "You want me to carry you, don't you?"

"Yes, please!"

And with that, your feet are swept out from under you. Jimmy walks you across the sand and through the sliding glass door, right to the bathroom.

"What are we doing in here?" you question as he walks right into the shower, "Jimmy?!"

"Gotta rinse all the salt and sand off," is all he gets out before the shower faucet sprays cold water on you and the man holding you. You squeal loudly and practically jump from Jimmy's arms! You hold onto him tightly for warmth; luckily the water heats up quickly though.

"You bastard!!" you yell and give the man a swift pop on the chest.

"OW!" he giggles and rubs the spot that is quickly turning red.

Your face forms a pout, feeling bad for smacking him, "I'm sorry." You take a step forward and rub your hand on his chest to sooth the spot. When you place your other hand on his chest, you look up at him. Suddenly you feel his strong hands gripping the back of your head, and his lips meet yours. Your back comes into contact with the shower wall, and you're completely surrounded. You feel the muscles of Jimmy's arms squeezing around you as his tongue urges it's way into your mouth.

You could hardly explain it: the timing and the situation feel so wrong, but he feels so 𝘳𝘪𝘨𝘩𝘵, like everything you had ever wanted- no, 𝘯𝘦𝘦𝘥𝘦𝘥.

Water soaks your hair, your face, your bodies as Jimmy fiercely kisses you. He's almost scared to stop.

But when you gently suck his bottom lip into your mouth and give it a nibble, it's game over.

Your friend-turned-lover rips open the shower curtain and starts walking you to the bedroom, his lips and his body never leaving yours. His tropical shirt slaps the ground in a wet heap, quickly followed by his swim trunks.

His lips find your neck, and you finally get a moment to catch your breath. Pressed against him as you step backwards, you feel his hands frantically working the straps of your swimsuit. You pull back from him just enough to see his face, and he freezes like a deer in headlights.

You simply look each other over, taking in the features of the other's face for a moment, before you lean forward and place your lips to his chastely, kissing him just once or twice. His rough hands gently caress your back, and then things turn passionate again when he slowly removes your top.

You always thought you'd be nervous to be with Jimmy, but after all, this is a man that you trust with your life. Wait- always? Did this imply you'd thought about being with him before?

In the heat of the moment you couldn't make sense of it. All you know right now is that Jimmy already has you naked and on the bed. It feels like your emotions are in a whirlwind, but Jimmy makes you feel good and you want more.

Your hands rake through his still wet hair, as he showers your chest in affection by kissing and sucking at your collarbone and breasts. He travels further down your body with his ministrations, until he reaches your soft inner thighs. You can feel his five o'clock shadow scratching at the delicate skin there, before he stops and looks up at you nervously. You'd never seen this man look nervous before.

His eyes beg for permission to go down on you and his hot breath passes over your center. You simply push down on his head a bit as a signal to go.

With his elbows buried in the soft mattress, forearms wrapped around your thighs, and eyes closed in concentration, his mouth surrounds that little bundle of nerves, lighting a fire in your belly. The sound of him breathing through his nose and your moans fill the room. Every hair on your body stands on end and your toes curl at the feeling of Jimmy Conway giving you head.

Oh God, Jimmy Conway is giving you head... Jimmy Conway your best friend. Jimmy Conway your Maid of Honor? You quickly push that thought away, then raise your head to look down at the man happily working away between your legs.

This is something you never thought you'd do with Jimmy, yet here you are, and oddly, it feels so... comfortable. You aren't nervous at all. Of course, you can't speak for him.

You lightly scruff up his hair, breathing heavily, "Jimmy..." The first word anyone had said in a while.

"Huh?" he says just after a loud slurping noise. His mouth hangs open in a relaxed way as he catches his breath and looks up at you from under his brow bone.

You let out a laugh in the form of a puff of air and a smile. Jimmy returns the smile; it's a happy smile with a hint of playful mischief in his eyes. A giggle slips out of you, then you both start laughing. At what, you aren't quite sure... the situation, maybe?

Your lover crawls on top of you and cuddles you by pressing his chest to you and wrapping an arm around your waist. Your hands explore his back, lightly scraping your nails over his shoulder blades and the small of his back.

He lets out a soft but deep moan before moving to kiss you again. His fingers nestle in your hair as he softly shows you his affection with his mouth. Your hands rest on his cheeks as he centers himself on top of you, one of his hands gripping under your thigh.

"This alright, princess?" he says in a near whisper.

"Yeah..." you exhale.

"You ready?" He gives you a kiss on the cheek.

"Yeah," you repeat, "I am." You give him a warm smile, cupping a hand on his face again, as if framing it to take a mental snapshot.

His next actions are incredibly gentle, but it makes everything all the more sensual. He plants a few kisses on your neck and collarbone before sitting up on his knees. His arm wraps around your thigh, holding it up in the air, as he aligns the head of his member with your entrance. The tip slides in pretty easily because of your wetness, and you can see Jimmy's breathing deepen; after that, the man moves slowly entering you, making you feel every inch of his length.

You had barely started and you're already both a mess. The pleasure is almost too much to take. Once Jimmy starts to move his hips, he leans forward once again, hovering over you on his hands and knees. You look up into his eyes, feeling his hardness moving inside you. Wanting to be closer to you, he drops down to his elbows and brings his knees up. His hands stroke some hair from your face while his hips rut into yours at a teasing pace.

After appreciating your how pretty you are, Jimmy moves his lips next to your ear and lowly says, "You feel incredible, baby. You feel so good..." He gives you a series of sloppy kisses on your jaw and earlobe.

You simply close your eyes, relax into the man on top of you, and give him an airy moan in response, "You feel good too, Jimmy."

"Mmmm, you like this pace? Or you want me to speed up?" You can feel his hot breath against your neck.

"Maybe, um, deeper?"

"Deeper, huh?" he whispers in your ear, "You wanna feel more of me?" He throws a little chuckle on the end of his question, and he readjusts by hooking a hand under your knee and pushing it up towards you for a deeper feeling while remaining close to you.

With each thrust you let out a grunt or breath of some kind, "Oooh... T-that's- Hnnng!"

"That the spot, baby girl?" Jimmy smiles to himself, happy that he's pleasing you.

A very shaky "mm-hmm" is all you can manage.

Jimmy speeds up his movements just a little, but still maintains a leisurely and romantic mood.

With a gasp, you start, "Jimmy, I- I'm-"

"Cum for me, baby," he coos, lightly sucking and nipping at a little spot on your neck.

"Fuck- Jimmy..." your climax hits you hard, making your head spin, and the only thing you can think about is the man before you, "Jimmy, I- I love you. I love you, Jimmy!"

Before you even have a moment to think about what you'd said, you hear, "I love you, too, (Y/N)," and several grunts and groans as he finds his release inside you.

Jimmy rolls off of you and trucks himself into your side. You hold the man in your arms tightly as you both come down from the high you just experienced. You turn your head to see him nuzzled into the crook of your neck, almost as if he's asleep. He cracks his eyes open at you and props himself up, putting his face close to yours.

You feel... shy for some reason as you press your lips to his, almost as if this is somehow more vulnerable than what you'd just done. You kiss each other softly, over and over, for what feels like a few minutes.

"You know, I didn't know you were close to finishing too," you tell Jimmy, trying to break some tension.

"Mm, well, I told you you felt good," he gives you a half smile, "I didn't know you loved me."

"Oh, well... It just kind of came out, but, uh, it was true. Still is." Another sweet kiss.

"You remember when I told you I couldn't wait to see you walk down that aisle? That was true too," he tells you.

You aren't sure where that came from, and it confuses you, "But... You knew I wasn't gonna get married that day."

"Yeah, but I am gonna see you walk down the aisle one day... when you marry me," he looks down and bites his lip.

You let out a flabbergasted little breath, "Jimmy..."

"C'mon, (Y/N)," he coos, "I love you. I wasn't gonna ever let you marry that other guy. Why do you think I looked into him so hard?"

"I don't understand. Why didn't you just ask me out years ago?" your question ends in a whisper.

"'Cuz I didn't realize what I had 'til I saw it in another man's arms," he tangles his fingers in your hair for another kiss, "but I'm not gonna let it get away from me this time."

• • •

Needless to say, you didn't see much of the beach or much of anyone the rest of your time in the Bahamas. You two already knew everything there was to know about another person, so you spent a lot of time exploring each other... in new ways.

So, it's bittersweet going home to Brooklyn. You'd been away a few months to let tensions between the two crime families die down. You would miss all of the alone time with your new man, but you're so happy to see your dad again.

"Thanks for driving us home from the airport, papa," you say, giving Paulie a side hug as he unlocks the door to the house not too far from the cab stand. You're greeted with hoots and hollers from Tommy, Henry and Karen, Tuddy, and a few others as you step inside. "What's this?!"

"Oh, uh, just a little surprise," Paulie chuckles, "A welcome home party for Jimmy and my girl."

Everyone starts exchanging hugs, giving you and Jimmy a proper New York welcome. As you put your arms around Henry's shoulders, you hear Karen from behind him, "OH no! I know ya not still wearin' your engagement ring," she grabs your hand and pulls you toward her to inspect the ring closer. Her voice lowers a bit, "No, this one's different. It's got pearls on it."

The room is filled with confused faces, until Jimmy takes your other hand in his, "Well, uh, we were on a little island for 2 or 3 months, pearls was all they had!"

Suddenly you're surrounded with Ooh's and Aah's and an "Attaboy Jimmy!" as it dawns on everyone that you're engaged.

"Hey, wait 'til they tell ya about how I'm gonna be a grandad!!" Paulie announces, and again the room fills with noise from everyone's surprise and congratulations. Any other family might have found it odd that you rushed into a new relationship, but this group likes keeping a closed circle, and everyone had their bets placed on you and Jimmy from day one.

Speak of the Devil, you feel his arms slip around you and a hand rests on your baby bump. He whispers in your ear, "I love you both so much. This is the way it always shoulda been."