Home > Becoming the Street Boss(4)

Becoming the Street Boss(4)
Author: Hayley Faiman

I stay standing outside, waiting. Luckily, I’m not forced to wait for long. Both Mia and Arlo appear. At least, I assume that’s who is in front of me. The woman is gorgeous, but she looks like a complete ball buster. I’m totally in awe of her.

The man, handsome and naturally in a suit, because that’s all the men in this world wear. I almost roll my eyes. Cliché. Cliché. Cliché.

“Pippa Mazzilli?” he asks.

Tilting my head back, I look up into his eyes. “Yes. Can I talk to you in private?” I ask.

He looks over to the woman, then to me and smirks. “Come into my office. I’m intrigued as to what you would like to discuss with us, here.”

They both turn around and I follow behind them. I don’t look around, choosing to keep my eyes to Mia’s back as I follow them. They guide me toward a door that opens into a small, narrow hallway.

We walk, passing by several closed doors, but Arlo doesn’t stop until we’re at the end of the hall. Reaching his hand toward the knob on the left-hand side, he turns it and steps inside. Mia doesn’t even slow down her steps as she breezes through the opened door.

Keeping my pace steady, I walk by as well. Arlo is standing with the door in his hand and closes it, flicking the bolt closed before he rounds his desk and sinks down in the leather chair behind it. Mia takes her place at his left, standing just one step behind him and to the side.

“Please,” Arlo offers, holding his hand out palm up toward a chair across from his desk.

Gulping, I walk over and sink down on to the edge of the seat. I can’t keep my knee from bouncing as I look at the two of them across from me. They are seriously intimidating. Arlo arches a brow as his eyes roam over my body, assessing.

“Please, how can we help you?”

Pressing my lips together, I inhale a deep breath, then release it on a sigh. “I want to auction my virginity,” I blurt.

Mia’s eyes widen. Arlo clears his throat. The room goes completely silent again. I watch, waiting to hear what they’re going to say. What’s the worst that can happen? They kick me out and make me leave? Actually, that would be horrible, because I would have nowhere to go.

Arlo looks down at his desk, then lifts his gaze to me. “Why?” he asks. “You’re free, Pippa. Why do you want to do this?”

“My aunt doesn’t want me to live with her anymore. It’s this, or be homeless. I need some money until I figure out my future,” I admit.

Arlo nods once. There’s a moment of silence, it feels like it lasts a lifetime as I wait for him to speak.

“I have three options for you,” he says, his voice low and even.

I bite the inside of my cheek, waiting to hear what he’s going to say. I have no clue what his options could even entail.

“One, you can auction your virginity. Two, I can have you trained and you can live here, be one of our girls.”

“Three?” I ask.

His eyes almost dance as he watches me, I can tell this is something I may not like, but he thinks is almost comical. Frowning, I wait for him to just tell me. Whatever it is, I have the freedom to tell him no.

“Want to get married?”

 

MASSIMO

 

 

She sinks to her knees. Her big blue eyes look up at me as she cups her tits and opens her mouth. She knows what I want, except she can’t be who I want.

Sliding my hand through the blonde hair at the side of her face, I gather a handful behind her head. Gripping the back of her hair, I tug her forward. She swallows me without resistance—expertly.

Closing my eyes, I imagine Pippa in her place. It’s been years since the woman has been on my mind and I can’t shake her. I pretend that it’s her dark hair I’m holding on to instead of this woman’s blonde. I imagine an olive complexion instead of the pale skin on the woman on her knees for me.

Opening my eyes, I pull her off of me, my breath coming out in heavy pants. I don’t want this to end yet. A blowjob isn’t going to be enough to satisfy me tonight. I need more. I need to fuck.

Jerking my chin toward the bed, she doesn’t even hesitate a moment. Instead, she stands and I watch as she makes her way over, climbing onto the mattress. She sits on her knees, her back and ass to me as she looks over her shoulder.

Walking slowly up behind her, I slide one arm around her waist, the other I dip between her thighs. Her lips touch the underside of my jaw, careful not to take too many liberties like touching my mouth without my permission.

Her pussy is damp as I slip my fingers through her soft folds. “How do you want me to come?” I ask.

She shakes her head once, her lips skimming my jaw still. “I should be asking you that, Massimo,” she breathes.

Smirking, I flick her clit and laugh softly when her thighs shake. “But you’re not. Tell me, cara. I want you to shatter.”

“I want you to fill me,” she whispers.

“Your ass? Your cunt? You have to tell me,” I say.

She pushes back, a cry escaping her pretty plump lips. I shiver when I feel one of her hands slide over mine between her legs. “Fill my ass, Massimo. I know it’s what you want. Play my pussy and fill my ass the way you desire,” she whispers sweetly, her Irish lilt filling the air around us.

Reaching for the lube and condom, I sheath myself, my hand between her legs still working her. She leans forward slightly, her hips shifting naturally as I continue to play with her pussy at the same time, I use my other hand to warm up her tight back entrance.

It’s not the first time I’ve fucked her ass, in fact, it’s one of my favorite things to do with her. She pushes her hips back, looking over her shoulder at me. Her eyes are wild, her nostrils flare as she rolls and shifts her hips.

“What do you want?” I ask as I sink two fingers inside of her back entrance.

I fuck both of her holes with my fingers, watching as her eyes roll in the back of her head slightly. Her words will be what I want to hear. I’ve paid handsomely to hear them, however, I do hope that at least part of her means them as well.

“I want you inside of me, Massimo,” she whimpers. “I need it.”

Sliding my fingers out of her ass, I align my cock with her tight rosebud entrance. My fingers don’t stop playing with her clit, in fact, I start to rub her harder, tapping her there every so often. Her hips jerk as she pushes back, taking more of me inside of her.

Gliding my free hand up the center of her back, I wrap my fingers around the front of her throat and gently pull her up so that her back is against my chest. Burying my face in her neck, I sink the entire length of my cock inside of her ass with one thrust of my hips.

“Fuck me hard, Massimo,” she begs. “You’re the best I’ve ever had. Only you know how to make me come,” she whimpers.

I don’t know if it’s bullshit, but her words cause my entire body to jerk. I imagine Pippa saying them. I’m a dick for that. I know that I am, but it’s also just the fucking truth. I’ll never have her beneath me like this, so all I have is my imagination.

“Play with those pretty tits, cara,” I rasp against her ear.

She nods her head, her hands lift to her tits, and without another word, I pull out of her a bit before I sink back inside. My fingers continue moving through the folds, then fill her, pulling out before I flick her clit—over and over.

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