He laughs. “Always so eager. No.”
I flip him off, earning more laughter, before gripping my ass cheeks and pulling them apart. Pressure is applied to the butt plug as he pushes against it.
“Are you happy?” I grumble. “I’m not a liar.”
“No, you’re not,” he agrees. “In fact, I think I should reward you, sweet girl.”
I shiver at his words. “Oh yeah?”
“It’s a freebie.” His fingers brush against my pussy. “You want a freebie, beautiful?”
“Y-Yes,” I whisper.
“Beg.”
“Please fuck me.”
He smacks my butt cheek hard, making my ass clench and sending strange sensations shooting through me. “The freebie isn’t my dick, greedy girl.”
“You’re a tease, Win. A fucking tease.”
“Beg me to put my fingers inside you.”
“Please, for the love of God, finger me.”
He chuckles as he runs his knuckle across the opening of my pussy. “You’re so wet. Are you always this horny, Miss Elliott?”
“Only since I met you.”
“Good answer,” he croons as he pushes a finger inside me. “Fuck, look how tight you are.”
I gasp as he slowly fucks me with one finger. With the butt plug inside me, it intensifies the feeling.
“I bet that pencil-dick boyfriend you had didn’t even properly break you in,” he rumbles. “My dick is going to split you wide open, baby. It’s going to hurt. You’ll cry because you’re just a little girl who wants a big man’s dick but she’s too small to take it.”
His filthy words are always so fucked up, but they turn me on more than I’d like to admit.
“Your dick’s not that big,” I taunt. “Don’t oversell yourself.”
He pulls his finger out, and then I hear the zipper on his pants go down. I tremble as I anticipate him sliding inside me. When I feel the soft skin of his dick rub against my pussy, I whine, wiggling my butt at him.
“Does this feel small to you?” he murmurs, sliding it over my clit.
“It feels average,” I lie.
He hums in disapproval, teasing his tip over my slick entrance. I want him to push inside me. Instead, he rubs against me, never entering.
“Maybe I should put it here.” His words are cold as he tugs at the jewel of my butt plug. On reflex, I clench. “Ahh, relax, little one. You wanted to talk a tough game, and now it’s time to be tough.”
A whine escapes me when he begins pulling on the plug. It burns as he gently tugs it from my ass. He tosses it onto the desk with a loud clank.
“Tell me this feels average,” he growls, pressing his tip against my aching asshole. “Tell me.”
“I, uh, it’s big.”
“I said tell me it’s average.”
“Winston,” I breathe, “it’s too big to go there.”
“No, Ash, it’s average. You said so yourself. Beg me to put my average dick in your ass.”
“It’ll hurt,” I croak out.
“Fuck yes it’ll hurt, which is why I’m not going to fuck you with it.”
His words are confusing.
“I don’t know what you want,” I whimper.
“I want you to beg for me to fill you with my average dick.”
“Win—”
“I have work to do,” he says, his words going cold. “Get dressed and—”
“Put your average dick inside me, you piece of shit.”
Fire burns through me as he roughly pushes his not-so-average dick past the sore ring of my asshole. I scream, uncaring that Deborah can hear, and grip the desk as he painfully drives into me. It’s a slow push that hurts like a motherfucker. Tears leak from my eyes, messing up my makeup. His dick is too big. I sob, overcome with pain and embarrassment.
Why do I ask for this?
Why do I allow it?
He doesn’t move. He doesn’t fuck me. He doesn’t pull out.
No, the awful bastard strokes my hair like I’m a kitten.
“If I were to fuck you with no lube, I would tear your pretty ass up and make you bleed. You have no fucking idea what sort of restraint it takes to not do exactly that. I’m there. Inside you. Owning you.”
My body trembles as I cry. I can’t form words.
“But I’m not some teenage douchebag like your last boyfriend,” he rumbles. “This is just a freebie. To let you know what sort of dick you’re dealing with. It’s a preview before the main event. One day, I’ll fill this pretty ass up with my come. Today, you just get to feel it.” His hand works its way beneath me, seeking out my clit. Stars glitter in my vision as he rubs me there. “I want to feel you come with my dick buried in your ass. Then, you dirty, filthy fucking girl, I want you to wear my come all over your pretty face.”
“Win,” I sob.
“And you’ll do it, won’t you? Because you crave this goddamn crazy shit. Because you’re just as sick as me.”
He pinches and tugs and rubs at my clit until I lose all sense of reality. I come while crying, my ass clenching painfully around his too-big dick. As I’m shuddering, he roughly pulls out, making me scream.