'Sup, ya gawgeous beans! I'm beyond the moon excited to start off this story, and I really hope that you guys would get to enjoy it as well!

But, of course, as I've already said before I'm more than open for honest criticism in the comment section to help me grow better as a writer. Again just please remember to be RESPECTFUL, m'kay?

And so, without further ado... Here's le prologue! 🙆🏻‍♀️

⊱ ────── {⋅. ✯ .⋅} ────── ⊰

      LEONARDO VALENCIA has always been a playboy. From his teenage years and even now in his mid-fifties, Leo has a very keen appreciation for women from all sorts of backgrounds.

He is a gentleman with a silver tongue and charismatic charm to boot. It's quite rare for him to chase after anyone, as most women actually come flocking naturally to him. And say what you will about the mob boss, but he sure does know how to treat a fine lady.

His first serious relationship was with a classmate of his way back in his senior year of highschool; a lass by the name of Daphne Carter. She was a pretty little thing, along with a sweet personality to match--the very epitome of a good girl.

She was a complete contrast to their school which was full of rebellious kids and careless staff. She was studious, and actually cared about her education.

Which came as a total shock to everyone when she and Leo started dating. It all began when he was having trouble with Math and Daphne, who had empathy, offered to tutor him.

To say that her parents were horrified would be an understatement. Their precious daughter, helping an infamous crime lord's son? PREPOSTEROUS!

And as the hopeless teens' feelings for each other bloomed, Daphne's parents were absolutely livid. Not a day went by when they didn't scream at her, chiding her for losing her damn mind and fraternizing with a lowly gangster.

But they never said anything directly to Leo. They may be furious, yet they were smart enough not to mess with him. Who knows what could happen to them?

The students were the exact same. Every person who ever bullied Daphne before immediately backed off, and she was constantly under Leo's protection.

But fairly soon...everything went downhill.

Leo and Daphne welcomed a baby girl to the world just right after they graduated. Her name is Francesca, and she inherited her mother's bright green eyes. For a while, they were both happy with their unexpected little family. Leo even considered marrying Daphne to make things truly official.

However, it was simply not meant to be. Having enough of it, Daphne's parents finally gathered the guts and stood up to Leo. They were not about to be family with such a criminal--they'd rather die!

And so, they forced Daphne to leave with them. They used Francesca, their own granddaughter, as blackmail; claiming that they would find a way and give her up for adoption unless Daphne agrees to their conditions.

Daphne had no choice. She loves Leo with all her being, but their child was her top priority. And so, with a heavy heart, Daphne packed up her belongings and the Carters were never to be seen again.

In her wake, she left a letter with shaky handwriting.

To my dearest lion:

You know that I am desperately in love with you. From the moment you gave me a smile--a genuine smile--when you correctly answered an equation, you already had my heart. I felt like I saw the REAL you back then, not the Leo I keep hearing about with a wicked reputation. You treated me very gently, and every passing second I felt so wanted and loved. I've honestly never been any happier in my entire life.

Which is why this is so difficult for me... I wish it didn't have to be like this. I wish that I could stay with you and watch as our little Francie grows. Her first steps, her first word--I truly wish I could be there.

I'm so sorry, Leonardo. I love you.

Forever Yours,
Daph

P.S. Please... Don't come after me. It's better this way.

"Better this way..?" Leo murmured, burning tears blurring his vision before ripping up the letter to hundreds of pieces. "Dammit, I wish I never met you!"

His yelling caused Francesca to awaken from her nap, wailing from her crib. But he couldn't even register it as he collapsed to the floor, the tears now freely streaming down his cheeks.

Fast forward six years later, Leo was quickly rising in the ranks. It wouldn't be long before he would become the next don, his father getting old and weak then the title would be passed onto the eldest.

Francesca was never shielded from the harsh reality of their familial lifestyle. What use would it be, anyways? Despite being a child, she already pretty much knew about everything. But she never once complained or feared it. In fact, she never looked away or covered her ears. She was just there, observing the recurring violence with pure curiousity as her innocence was blatantly stripped away.

It was hard for Leo to raise her, and not just because he's a single father. It was the emotional baggage that came along with it, and every time he looked into those emerald eyes of his daughter...he gets reminded of her.

Which was why that after all the years of being shut in, he finally agreed for a night out with his twin brothers Gabriele and Raffaele. It has been such a long time, Leo merely not having any will to play around, but he figured that some fresh air and an attractive woman or two could help ease his mind off of the stress.

Leo left Francesca in the care of his father, who quite surprisingly had a soft spot for his inquisitive granddaughter. Him and his brothers were about to traverse to a popular new club downtown, iKandy. But besides the fun, Gabriele and Raffaele mainly wanted to go there to scope out what kind of competition they had since they were also planning on opening up their own nightclub.

It was the usual. Blaring music, colourful strobelights, the occasional spiked drink. But there was another part of the club that is lavishly styled with comfortable white couches, lit up by faint gold and purple moodlights as well as neon décor.

It was a place of relaxation, away from the rowdy crowd of drunkards and strippers on the other side. Customers were chatting, clutching their various strong alcohol as they laughed amongst themselves.

Then, that was when Leo's eyes landed on a younger blonde woman sitting by the bar. She was dressed to the nines, her smooth legs crossed and crimson lips sipping at her dry martini before their gaze locked.

He will soon learn that her name is Camille LaGrand and she is, in fact, the club's business savvy owner.

Camille was everything Daphne wasn't. She's confident, seductive, and takes charge. Whereas Daphne is kind, meek, and fragile. Leo indeed loved her as much as she loved him, but Camille was an exciting and euphoric new taste.

She never took shit from anyone, and never hesitated at all to call out Leo whenever he said or did something that she didn't like. And that's what he adored about her; she always knew exactly what she wanted and how to get it.

Ultimately, though, that's what led to their downfall.

Camille was raging when she discovered her pregnancy. Leo tried calming her down, which only earned him a smack to the face.

"I fucking HATE you!" She screamed, her French accent ringing out. "Do you know what this means to me?! I have my whole life ahead of me, Leonardo! I don't have time for a goddamn baby, let alone do I even WANT it!"

"Maybe you should've thought of that before screwing me!" Leo retorted, clenching his fists angrily. "Even when we were on contraceptives, there's still always a chance of pregnancy!"

Camille laughed sardonically, faking a smile. "Oh, so you're blaming this on me? This is YOUR baby, this came from YOUR filthy cum!" She shouted. "You and your fucking pull-out game... PATHETIC!"

Their argument went on for what seemed like hours. Swears were spat, furniture was thrown; but, alas, they came to an agreement. Camille won't abort the baby, and Leo would have full custody over him or her. In exchange, they would never see each other ever again.

A perfect deal.

And that was when Alyssa was born. Leo showered her with all the affections that her sorry mother could never give her, and she was easily the favourite child.

Francesca had always been envious.

Then, as time passed, that was when Leo met Frey Thatcher.

She was caught spying on his family and exploiting them to a rival gang as payment for drugs. When she was brought in, she was delirious; sobbing and begging for her life nonsensically, telling the Valencias that she'd switch her loyalty to them instead if they just spare her.

By then, Leo has been appointed as the new don so the decision rested upon his shoulders. Should he kill her or let her go?

...He let her go. He felt pity--she was nothing more than a poor woman who managed to get stuck with the wrong crowd. He even promised to give her security, if she allowed him to help her with her addiction.

He still clearly remembers the disapproving scowl his father shot him as he uttered the words. Then he sighed and walked away, disappointment weighing on his too forgiving son.

Eventually, Leo and Frey increasingly drew closer until a romance sparked between them. After what seemed like a dreadful eternity, he actually felt like he could be happy again. He felt complete with the dark beauty, and they consummated their relationship by having a baby.

It was yet another female, and they named her Tatianna. Everything was fantastic...or so Leo thought.

The temptation was just far too great for Frey, and she unfortunately lost her battle. She fell into a deep spiral once more, consuming herself with drugs and other questionable substances. And, under the stifling influences, she went for a drive and got involved in a car crash.

When the tragic news was delivered to Leo, he felt his whole body freeze.

No... No, it just can't be. It CAN'T be!

He felt a light tug on his pants. Looking down, Tatianna was staring back up at him confusedly.

"Mamma?"

Leo couldn't take it anymore, breaking down at that. He swooped his daughter into his arms, his body shaking as he wept.

Tatianna, puzzled, could only wrap her small arms around his neck. "I dun wike it when Papà cwies."

"I know, sweetie..." He sniffled. "I know."

The funeral was depressing--there was no other word for it. People donned in black as the sun hid away, and even other criminals they work with attended. But for them, it was nothing more than to take advantage of the opportunity to be under Leo's good graces.

All throughout the service, Tatianna was bawling. Calling for her mother, snot snivelling down her nose. Francesca and Alyssa were on either side of her, holding onto her to prevent their toddler half-sister from dashing towards Frey's casket.

Leo had enough of it, and in the middle of the service he jumped up. "SHUT UP! FOR FUCK'S SAKE, SHUT UP!"

And he stormed off. Back into the manour, all by his lonesome in the kitchen as he drank away his impending sorrows. Seconds turned to minutes, then minutes into hours--and he fainted.

He was an utterly miserable sight to behold, and no one dared to approach him...except for Nadine Arden.

She has been with the Valencia syndicate for several years now, and has proven to be one of the mafia family's best assassins. She did a lot of their covert dirty work without question or fail, and she secretly harboured feelings for the distressed don.

Seeing him like this placed a bitter taste on her tongue, and she just couldn't leave him. So with all her might, she propped one of his arms over her shoulders and carried him upstairs to his room.

When he plopped onto the bed, it was then that his eyes slowly fluttered open and clashed with Nadine's steel blue ones.

Through his drunken haze, however, he hallucinated; he wasn't looking at Nadine. Rather, he envisioned Frey.

"You came back for me." He slurred, a lopsided smile forming on his lips. "Oh, god, Frey... I missed you."

Nadine's eyes widened, and before she could snap him out of his reverie he suddenly pulled her down and their lips connected. She struggled for a bit, but he was bigger and stronger than her.

How many times she has imagined kissing Leo, that she would be the one with him instead. But she was always overlooked, and was nothing more than just another lackey... She didn't want to have him like this, but there was no way out of it.

So, she succumbed to the painful desire.

And the very next morning, regret hit them both like a freight train.

It was how Sofia came to existence, Nadine's bundle of pride and joy. She loved her daughter to bits even despite the circumstances. But it reached the point when she couldn't handle it anymore. Every single day she wakes up, and Leo regards her with such brooding and rueful eyes.

It ate her up more and more, until she decided to run away. She so desperately wanted to bring Sofia with her, but it was impossible. She barely had enough money for the two of them, and it was extremely dangerous to wander around the city aimlessly with a baby especially for a targeted contract killer as herself.

And so she tucked away a letter for Sofia, her favourite stuffed bear holding it.

To my little angel:

As you grow older, you will realize that things aren't always how they should be. I learned that the hard way. And though I may not be there with you physically, just please know that there's not a moment that I don't stop thinking about you.

I love you, Sofia. I don't expect you to forgive me, but I at least want you to know that. You are the best thing that has ever happened in my life, and even through everything I wouldn't change it for the world.

With all my heart,
Your Mother

Leo read through the letter before letting out a large exhale.

"Damn... It's like Daphne all over again." He grumbled, running a hand through his dishevelled hair. He folded the letter and shoved it into his pocket, trudging out of Sofia's room.

A few more years went by, and Leo transformed. He wasn't forgiving anymore--he was cold and ruthless. There was no space for mercy, and in a crime-ridden city like St. Desdemona the only way to survive is to be on top of every damn thing.

Flings were typical for him. No more romance, just straight casual sex. Love only weakens foolish bastards, and he was like that once. But he had needs, too, and in his age he's still got it.

His new affair? None other than Elise Monroe, Gabriele's girlfriend.

Leo's morals have been further and further slipping away, and after an inebriated one night stand with his own brother's lover it then turned into a sober two...three--four until it became a repetitive cycle.

But can you blame him; he'd think it to himself. Elise was a gorgeous specimen, with her wild curls and sharp tongue. It was such a shame that Gabriele was letting all of her go to waste. She often complained to him about how Gabriele would ignore her, too busy dealing with business and the thugs who crossed him. That would almost always follow with rough sex, making her forget who the hell Gabriele even was.

Before long, though, Gabriele found out. He spotted a positive pregnancy test thrown in the trashcan in their shared bathroom, and he knew that he hasn't had sex with Elise in a while so he most certainly wasn't the father.

When he confronted her about it, she at last came clean and admitted that Leo's the father. Driven with blinding wrath, Gabriele took no time at all and rushed over to Leo. He ensued a fight right in front of the girls, and even Raffaele was alarmed. He was usually the more riotous one, but Gabriele's rage was only understandable. And so he ushered the girls away, leaving his two older siblings to resolve things for themselves.

Once the adrenaline began withering away--both of them thoroughly beaten to bloody pulps--Gabriele simply stood tall, brushed off his clothes, and walked out.

Gabriele didn't speak to Leo for an extended time, and it was killing him. He realized far too late that what he did was incredibly wrong, and that he hurt his own family because of it. But when it was time for Elise to give birth, Gabriele accompanied her to the hospital with Leo.

It seemed as if a silent understanding passed between them, that Gabriele was willing to forget the terrible incident if he could just have his brother back. All they had was each other, and he'd be damned if he let a woman ruin them!

They sat in the waiting room with cheap coffee in styrofoam cups as the hours ticked by. No words were exchanged, and it wasn't needed. Finally, the doctor came out. But as they stood simultaneously, they noticed his grave expression.

They bolted inside, and there was Elise...dead.

But the scene was short lived as a loud cry cut through, and an elderly nurse very carefully handed Leo the infant wrapped neatly in a pink blanket.

Leo cradled the baby, gently shushing it. He really didn't know what else to do, sadly watching as his brother loomed over Elise. Her eyes were still open, tears staining her previously rosy cheeks, and swallowing the lump in his throat Gabriele shut them.

"What're you gonna name her?" He suddenly broke the tense silence, his voice cracking slightly as he tore his eyes away from Elise.

Leo instantly understood Gabriele's soundless plea. He yearned to be distracted by something--just anything to make the heartache disappear.

He looked down at his fifth and final daughter, so tiny and delicate as she sucked on her thumb. "Liliana."

Gabriele finally spared a glance at his niece, an ever so faint smile tugging at the corners of his trembling lips. "I'm sure the girls will love her."

⊱ ────── {⋅. ✯ .⋅} ────── ⊰

Wow... That was honestly pretty depressing for me and a lot for one backstory. I mean, I had my ideas and all, but I just didn't realize how heartbreaking it'd be.

Anywhore, on a lighter note, what're your thoughts? Please do tell me! And if you're curious then the five beautiful actresses on this part portraying the girls' mothers (in order) were Rachel McAdams, Erin Richards, Halle Berry, Blake Lively, and Michelle Pfeiffer. And yes, I was the one who made the (shitty) crackship GIFs.

There is definitely much more to come, so I hope ya stick around! But I politely ask that you please don't comment 'update' or 'when are you gonna update?' Don't get me wrong, of course I LOVE how readers look forward to my stories though I just find that rude and annoying!

Welp, with that said, buh-bye for now! 'Til next time, folks, and I hope you have a great day! 👋