The Mobster's Whore

Story Info
Mr. Aldine works out his frustration on Avery.
5.1k words
4.55
28.8k
54

Part 1 of the 11 part series

Updated 06/12/2023
Created 08/16/2021
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SiSub
SiSub
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I've been having a really, really fucking shitty day.

I was up to my eyeballs in cops and my enemies were having the time of their life enjoying my downfall.

I'd met with lawyers all day today and yesterday to try and figure a way out of this madness, but it wasn't looking good.

Right now, it was possible that I could face a minimum of twenty years in prison for my crimes.

Shit.

I hadn't gone home, knowing there would be cops waiting for me at my gate. For once, I needed to be by myself and just drink my damn sorrows away while listening to a consistent playlist and hope that liquor would alleviate my fears, even for a few hours.

I'd become a criminal in the most cliched way.

Poverty.

Watching my parents struggle to make ends meet to feed me and my siblings. My dad had lost his job in '88, and we only had my mother's nursing income to cover food and expenses for six people.

We'd had to move from a house in the suburbs to an old trailer in the wrong part of town. We got kicked out of school for changing districts and started attending the public school a few blocks from the park.

It was there that I got mixed up with the wrong crowd. I blinked twice and I was a part of the gang, running errands for my boss, a man named Big Earl.

He liked me, Big Earl. And I respected him.

He was the one who showed me how to take advantage of the situation and use my wits to get the most of a deal.

He taught me the basics, and five years after he'd taken me under his wing, I was in charge of my own little operation.

Big Earl didn't want me dealing with anything too bad, so he gave me the weed and told me he'd talk again when I tripled profits.

It took me about six months to achieve that goal.

That's when Big Earl decided to make me his right-hand man. Pretty impressive, for a nineteen year old, huh.

My parents were ashamed of what I did, but neither of them complained when I moved us into a better residence - it was still a trailer because I didn't want to attract any attention from the fed - nor did they say anything when I brought food to the table.

My sisters, both younger than me, didn't much care about what I did. At least not until Big Earl bit the big one and left me in charge of his various business at the tender age of twenty-one.

Drugs, laundering, protection racketeering, prostitution, bribery and some fraud.

Nothing special, nothing new.

I made it my goal to run a cleaner operation though, and I fired everyone who had been forced into a job. I wanted loyalty, people I could trust not to rat me out to the cops.

My prostitutes were the cleanest in the city, and they were about as classy as anything. The job was still disgusting, but they were grateful for the money, and I let them keep more than half of it since they'd more than earned it.

I own a building on the east side of town where the girls usually conduct their business. The cops didn't really know about it since I had put it in my brother's name - the only member of my family who didn't hate me.

So that's where I went. I kept a penthouse on the top floor where I usually slept when I was around that area on business.

The eighteen storey building had been remodelled years ago with a modern, sleek exterior and large, obnoxious windows.

The first floor was a lobby with crazy security, but you wouldn't know from the large reception desk and the posh gentleman sitting behind it.

The second floor was a bar, exclusive to certain clientele only. The third was a more... risque place where the girls got to take their clothes off and showed the fellas their goods if they wanted.

Floor three had a gym and spa, where they took care of themselves as best they could. The rest of the floors housed the girls, and the floor beneath mine were eight playrooms.

That's where all the nasty, dirty shit went down. And nobody had access to that floor without laying a hundred thousand on the table first.

I made my way up to the eighteenth floor, and glanced out the windows as the storm ragged outside, matching my mood perfectly.

I slowly made my way into the penthouse, turning on the lights I needed to find the bar and the phone.

My lawyers had advised me to only answer calls from them and my family, and the occasional legitimate business partner. Nothing incriminating, nothing suspicious.

So I picked up the telephone, and dialled two and pound for Mona's private residence.

While I ran the business, she ran the girls. She knew every single one of them, their preferences, their skill set, the shit they hated doing.

Despite it being past midnight, she sounded awake and alert.

"Mr. Aldine."

"Good evening, Mona."

"How may I be of assistance to you tonight, sir?" came her Southern drawl.

"I need something to take my frustration out on."

She paused for a second, surprised at my request because I never touched the girls. I just didn't.

Normally, I would scour fancy hotel bars for a quick lay, but I wasn't in the mood to fake being a gentleman.

My mask had been scrubbed off by the media, revealing the dirt and darkness I hid behind my exceptional smile and charisma.

There was no need, you see, for me to pretend to be something I wasn't just to get some pussy anymore.

I had about thirty, healthy, gorgeous women who'd been trying to tempt me for years. All I had to do was pick one.

"Of course, Mr. Aldine. What would you like?"

I poured a generous amount of my best bourbon in a glass with some ice in it, swirled the liquid around while I thought about her question.

"Experienced," I supplied. "I want her curvy, and a little soft, preferably with an ass and a nice pair of tits."

I took a sip, and swallowed.

"Resilient. Fearless. She should be able to... take what I'm going to do to her tonight. I don't want a girl who's going to cry when I get rough."

"Of course, sir. Any preference on hair and eye colour?"

I thought about it, then shook my head.

"You have carte blanche on those, Mona. I trust your judgement," I said, taking another sip.

"I'll have someone up in fifteen minutes," she said before I hung up.

I replaced the phone on the handle and moved to the living room, grabbing the remote and turning on the sound system.

I selected my favourite lounge music playlist and placed the remote down on the table before I went back to the bar to pour another glass of bourbon.

I took the decanter and set it on the table next to my right-back Chesterfield armchair, and sunk into the plush leather with a groan. I sat there, gun still in my holster, sipping slowly while I waited for the girl to arrive.

Thirteen minutes later, the elevator leading to my floor dinged, a sign that I had a visitor. I sat in the darkness of my living room, waiting for her.

I heard the door open, and her heels clicked loudly, confidently, against the wooden floor. Her steps were slow, measured, then a little unsure.

I was sitting so I could see her when she entered the room, but she wouldn't see me.

I thought she'd be shy about stepping into the living room, but her steps evened out once more when she saw the lights in the bar area, and she casually entered the room as if she'd been in here over a thousand times before.

My gut clenched at the sight of her.

Six-foot tall with a thick, curly mane cascading past her elegant shoulders.

Poised, confident, sexy.

She was wearing a short, spaghetti-strap lace dress that barely reached past her ass.

The skirt was loose, giving the look a softer feel. Her legs were long, toned, hips wide and belly flat.

Her breasts were full, tempting, and I desperately wanted to free them from their confines so I could squeeze and fondle as I pleased.

Her eyes were huge, brown and gorgeous, with an adorable little nose and full, pink lips. Lashes long, eyebrows trimmed and shaped to her heart-shaped face.

She paused with uncertainty, and looked around the room with mounting confusion. She frowned delicately when I didn't announce myself to her.

"Mr. Aldine," she called.

Her voice was sweet and soft. It reminded me of a delectable chocolate dessert, of figs and strawberries and marshmallows.

I didn't like how innocent and young she looked though, and I especially didn't like that she looked like she would cry if I raised my voice at her.

I swirled the liquor in my glass, announcing my presence. She turned towards me, and narrowed her eyes to try and spot me in the dark.

"What the fuck are you doing here?" I growled.

She frowned, and then began to fiddle with her fingers.

"I... Mona sent me. She said that you needed me... to alleviate your stress?"

I tilted my head and regarded her, then switched on the lamp on the table to my right, so she could see me.

As soon as her eyes locked on mine, her lips parted and those big eyes widened.

"Come here," I demanded.

Despite the surprise on her face, she practically floated towards me, coming to a stop just a few feet from where I sat, then clasped her hands behind her back.

This close, I could smell her subtle, almost candy-like perfume, and see the lacy choker she wore around her neck. It didn't take a rocket scientist to realise that she was more than a little intimidated by me.

She may have been the one looking down at me, but there was no mistake as to who would be serving who. Her eyes swept over my dark, wavy hair and my piercing blue eyes.

"What," I began, setting my glass next to the lamp, "Is your name?"

I beckoned her closer as I leaned forward, and she took two steps closer before answering.

"Avery."

"And how exactly is an innocent thing like you supposed to alleviate my stress?"

My voice was barely a growl, low and deep from frustration and need.

"Spread."

She slowly obeys, gasping when I slipped my hand between her inner thighs and grabbed at her firm, soft muscle with my large, callused hands.

I kept my eyes on her golden skin, and grunted like a barbarian when she tried to step away from me. I took my time touching her, marveling at the strength in her legs despite their softness.

As I stood up from the armchair, I let my hands trail upwards, stopping at her hips.

I looked down at her face, took note of the slight quickening of her breathing as I traced the waistline of her panties with my finger.

As I dipped a finger past the elastic, I tilted her head up with my other finger. Her eyes were slightly wide, searching and nervous as she waited to see what I would do.

"How old are you, Avery?"

She lowered her gaze to my lips, and then back up again. She forced herself to relax by inhaling deeply, and releasing slowly.

I slid my finger back up before touching her pussy, and let the lacy fabric go with a resounding snap.

I began to circle her, like a predator does when he's toying with his prey. Something inside me was hoping she would at least make this exciting for me.

I gathered her curls none too gently, and tossed them over her left shoulder, bringing my nose to her shoulder and inhaling the scent of her skin deeply.

Rosemary.

"Speak."

"Twenty-two, Mr. Aldine."

She shivered when I breathed onto the back of her neck, and shifted uncomfortably when I grabbed her ass brutally. She was definitely curvy and soft, with an ass and a gorgeous set of tits. But how much experience could a twenty-two year old have?

And she didn't exactly look resilient. I feared she would break the second I got rough with her, and I needed not to worry about shattering her spirit.

Despite my thoughts, I continued to fondle and touch her, running my hands over her flat belly and cupping her tits in my hands.

The girl looked smart, and she was downright gorgeous. She should be in a library, studying for finals or worrying about a boy not texting her back.

Not squirming like a mouse in a trap.

She gasped when I wrapped a hand around her neck, my grasp gentle and soft.

"I don't think you can handle what I'll be dishing out tonight, Avery. I want someone with a high tolerance for pain and humiliation."

I let my other hand slide under her skirt, and I reached between her legs and cupped her crotch.

"I can do that," she whispered eagerly.

I felt her body melt against mine, and I squeezed her lips with my fingers, pushing upwards almost painfully. She whimpered and moved to stand on the tips of her toes as the pleasure quickly turned to pain.

I tightened my hand on her neck, and she arched her back in response. I brought my face closer to hers, and gazed down at her closed eyes, the lip between her teeth.

I could feel her heat against my palm, the wetness seeping from her pussy and onto the crotch of those expensive panties she wore.

So pliant, so eager and ready for me.

Surely, this is what I wanted? Someone to bend to my will, to do everything I asked without question?

To submit to my dominance and allow me to do anything I want with that body of hers.

So why the fuck was I hesitating?

I dropped my hands and stepped back, and she inhaled deeply before fixing her dress primly.

"I don't think you can. Go back to your apartment and ask Mona to send me someone with experience."

I turned away from her and returned to my empty glass, pouring another measure of the amber liquid.

"Are you serious? Or is this some kind of test?" came her response.

"I don't have time for such nonsense. Do I look like someone who has the patience for tests?" I snapped.

She is quiet while I take another sip, and I wait to hear her heels click against the wooden floor, announcing her departure.

"Wait. I know I don't look it, but I can take whatever you want to dish out tonight."

I almost chuckled at that.

"I know about the case against you-"

I whirled around to glare at her, my outrage at her nerve plain to see. My hand tightened so hard around the glass that she glanced down at it with concern, perhaps worried it might crack.

She surprised me by standing her ground, though, and lifting her large eyes to my face as if curious to see if I would snap.

I loosen my grip on the glass, and let out a long, ragged breath to calm myself.

"I can help, I swear," she promised. "Please just let me try, and if I do anything that you don't like, you can send me away."

Well, there was that fearlessness I'd asked for. Though now that I was actually seeing it in action, I wasn't sure I liked it.

But why not? I couldn't possibly get any more riled up than I was now.

"Fine," I said. "Impress me, Avery. Should you fail, not only will you be sent away, but you'll be fired too, effective immediately. Do you understand?"

Her eyes softened, as if she somehow understood how on edge I was, and then nodded seriously.

"Good. Do your best."

_____________________________________

Okay, no pressure.

No pressure.

There was a reason Mona sent me up here. Granted, she didn't like me much because I was always busy with assignments, leaving my clients unhappy and horny.

But I more than made up for that later. I was disturbingly great at what I did.

I just had to show Mr. Aldine that.

So, no pressure.

I reached forward and took the glass from his hand, and gently placed it down on the table beside the decanter.

He raised a brow at my forwardness, and I moved back to stand in front of him, tilting my head up and peering at him with my huge brown eyes.

His dark, glossy hair was messy on his head, as if he'd run his hand through it several times in frustration. A few strands fell over his brow, and I wanted to push them away from his brow, but I didn't dare.

His midnight blue eyes were already pinned on me like he was waiting for me to do or say something he didn't like so he could fire me. Those tempting lips of his were pressed in a thin line, his strong jaw clenched with tension.

Oh, but the man was fucking gorgeous.

An absolutely spectacular specimen of man at his prime.

Powerful, ruthless, raw.

There were very few clients who could turn me on like this, and I had to masturbate prior to the appointment, but just looking at him was enough to make me gush.

Without looking away, I lifted my hands to the lapels of his tailored blazer and gently began to take it off his broad shoulders.

I tossed the jacket on the armchair, and reached for the tie that still hung neatly around his neck, slowly undoing it before letting it fall to the ground at my feet.

His eyes scanned my features as I began to undo all the buttons of his shirt, his breathing steady and deep.

I pulled the rest of the shirt out of his pants with the same speed, and pushed it off his impressive arms. I broke contact when I caught the lines of a tattoo.

After tossing the shirt on the chair, I let my fingers run over one of the wings of the tattoo. It spanned over his shoulder left pec, and I wondered where the other was, where the body could be.

Mr. Aldine grabbed my wrist, his grip on my arm so tight I actually cringed. He violently jerked my hand off his chest and took a step towards me.

"Your attempt at seduction is amateur at best," he remarked.

I do not respond to this, but I do look up at his face and see the impatience, the anger, the danger.

I continued to undress him, unbuckling his belt and lowering his zip. Before I removed his pants,

I lowered the straps off each shoulder and waited for gravity to pull the fabric to the ground. I stepped out of the white dress, bringing me even closer to the ruthless man in front of me.

He tried to keep his eyes on my face, but the urge to look at the lacy whiteness of my lingerie proved to be too much temptation even for hin.

He released a breath and met my gaze once more, his eyes darkened with lust.

I keep my underwear on as I knelt in front of him. My knees ache against the hardness of the floor, but I ignored the pain and focused all my attention on him.

I began with his shoes, taking off first the one and then the other, then his socks and finally reaching up to pull down his pants.

He allows me to do all of this without complaint, without any more snide remarks. I pause when I have the elastic of his briefs between my fingers, and look up at him for permission.

He nods ever so slightly, and I peel the fabric back to reveal a very large, very long cock that immediately made my mouth water. I swallowed, and glanced back up at him again as if to confirm that this mammoth thing actually belonged to him.

"Impressed?"

I blinked at the arrogant question, taken off guard by the smirk spreading across his handsome face.

"Tremendously."

_____________________________________

She started slow, her movements sure and steady.

I think she was more focused on acquainting herself with what I liked as opposed to teasing me, but it definitely felt like the latter.

She reached up to take my cock in her hands, and held the length, her eyes appraising it like she wasn't sure where to begin.

She shifted forward on her knees, and then stuck her little tongue out, licking from the root of my cock and stopping just beneath the head.

She licked me until I was glistening with her saliva then cupped my balls in her small hand and squeezed gently.

I liked that she had taken her sweet time undressing me and was slowly trying to push me over the edge with this agonisingly slow pace.

And fuck if she wasn't winning our little bet already. I watched her work, her clever little tongue avoiding the head of my cock as she licked and licked.

I grabbed a wistful of her hair and pushed her head back so she was forced to look at me, and she smiled softly at the frown on my face, the intensity in my eyes.

I suddenly wanted to throw her on the ground and fuck her until she begged me to stop, or until we were both dead.

Whichever one came first.

I wanted to look into those large brown eyes while I fucked her senseless, squeezing those large tits as I buried myself balls deep inside what I already knew would be a wet pussy.

SiSub
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