A couple days later, Sarah and Jim announce they’re going out of town for the weekend. Sam is given permission to spend the night at a friend’s, but Jenna has work in the morning, so she’s spending the night at home.
At least, she’s supposed to be.
I get to work on my laptop whenever I want, so I set up in the living room downstairs and grind away for a few hours, assuming Jenna is up in her room chatting with friends or something. At some point, my eyes begin to drift, and I’m eventually taken into a light sleep on the couch.
The sound of the front door creaking open jerks me awake. I glance around and notice my laptop on the coffee table. Then, I see Jenna slip through the front door, moving quietly.
“Jenna?” I ask, still blinking away some of the fog of sleep.
Jenna freezes, then glances toward me. She’s wearing a short skirt that shows off her legs, and a henley tank top that offers a generous view of her breasts.
“Sorry, Mar—Mr. Matthews,” Jenna stammers. “I thought you’d be in bed by now.”
I glance at my open laptop. It is past one a.m. Damn. Gaze moving back to her, I ask, “What—were you trying to sneak in?”
The grimace on Jenna’s face answers my question.
“Why?” I ask.
Jenna flushes. “I agreed to keep following my dad’s rules in exchange for not paying rent, even though I’m nineteen. He doesn’t like me going to parties or staying out after midnight.”
I look her over again before I can think better of it. A party? I wonder just how wild it was. She seems pretty sober.
Jenna clears her throat. “Are you…going to tell him?”
I hesitate. Should I tell Jim that Jenna snuck out to a party? It feels wrong to hide this from my friend. But I feel bad for Jenna. Nineteen is too old to be putting up with rules like this.
Then again, she did agree to them. Regardless, I’m not keen on the idea of lying to Jim, even if it’s just a lie by omission.
Jenna tugs at the bottom of her skirt, drawing my attention once again to how short it is. To how much of her thighs are exposed. “Maybe you could just…handle this instead?”
It takes me a moment to process what she said. Tearing my gaze away to meet her eyes again, I say, “Huh?”
“You could punish me for breaking the rules instead. Maybe then my dad doesn’t have to know?” Squirming a little, Jenna adds, “If you don’t tell him I snuck out, I won’t tell him about…whatever you decide to do.”
My face heats rapidly, and there’s a stirring between my legs. Is she actually implying…?
“Hm.” I clear my throat. “Maybe I can agree to that. Why don’t you…go up to your room, I’ll be there in a minute to decide an…appropriate punishment.”
Jenna nods, finishes closing the door, and hurries up the stairs. I wait a moment before rising to my feet, my attention on my throbbing erection.
Images of Jenna flash in my mind again. Images of her cleavage, her legs, the memory of her touching herself. I’m sure as hell not going to pass up this opportunity.
Still, I try to get my cock to relax a little before I head up the stairs, taking a few moments to think about work in an attempt to distract myself. I’m not sure I’ll be able to keep it down when I see Jenna again, but I’d like there to be at least some build up.
I walk up to her room and see her door ajar. I push it the rest of the way open and step in. Jenna’s laying on her bed on her stomach, and her head turns back to watch me as I enter the room.
My gaze slides over her ass, which she has pushed up at an angle that seems deliberate. As I stare, she rolls onto her back, and now it’s her breasts I’m staring at.
“Do you always dress like this when you go out at night?” I ask
She flushes. “Like…?”
“Showing off your body like that.” I walk toward the bed and stand over her. “Making yourself fucking irresistible.”
Jenna’s face flushes, and she squirms, squeezing her legs together. “I probably shouldn’t be dressing like this either. I just…can’t help being naughty sometimes.”
And just like that, I’m rock hard again. I rest one of my knees on the bed. “Maybe you do need a little punishing.” I move my other leg onto the bed so that I’m straddling her. Jenna lets out a slight groan.
“What do you think?” I ask her. “Do you deserve to be punished?”
“Yes sir.” Jenna nods.
I move my hands to her tits, the tits I’ve fantasized about for days. I squeeze them through her shirt for a moment before letting my hands slip beneath the fabric. I groan with pleasure. My cock throbs.
“M—Mr. Matthews,” Jenna stammers.
I fantasized about her moaning my first name, even heard her say it when I watched her, but something about Mr. Matthews is even more arousing. I begin to grind against her, letting her feel my erection through my pants. She whimpers and arches her back, pushing her breasts up. I squeeze them for a few more seconds before forcing my hands to pull away.
I fumble to unzip my pants and free myself. Precum is already leaking from my tip. I shift my focus to her legs, pushing her tiny skirt up to give myself a full view of her thighs and her lacy black underwear. I grind against the soft skin there, letting my precum coat it.
“It’s going to be so easy to take you,” I tell her with a groan, inching closer toward her entrance. I let my of my hands slip between her legs, and am surprised by how wet she is. “Oh, you like this, don’t you? You naughty girl.”
Jenna moans and arches her back again. “Fuck—yes sir. I’m a slut.”
“Fuck,” I gasp, feeling myself get closer to the edge. I’m not going to last long once I’m inside. Maybe…
I shift my weight so that I’m a bit further up her body. I grab her breasts again and squeeze. “Your tits are so perfect. This slutty little shirt can barely hold them, can it?”
Jenna nods and moans again.
“Stroke my cock,” I order her. “I’m going to cover them with my cum.”
Jenna obeys, taking my length in her hand and sliding it up and down. I pull her shirt down to expose her bra. Her massive tits jiggle with her movements.
“Fuck yes,” I gasp. “Fuck. Just like that. I’m—I’m so close—fuck! I’m going to cum all over your tits—”
Her tits keep bouncing as I reach my climax and coat them with my cum. I move my hands to her wide hips and squeeze them as I finish, completely overwhelmed with pleasure.
“That’s right,” I groan. “My cum belongs on your tits, you little slut.” She looks so fucking perfect like that. Some of my cum has landed on her neck, too, and a little on her face.
I slide my hands back down to her thighs and continue squeezing, imagining them coated in my cum, too. I have different plans for my next load, though.
It doesn’t take long for me to get hard again. I push Jenna’s legs farther apart, earning a yelp of pleasure that makes me shudder with satisfaction. It’s easy to move her underwear to the side and give myself access. I eagerly thrust into her. She’s tight and wet as she envelops me, and it takes everything I have not to cum immediately.
Jenna gasps as I fill her with my cock. “Your so big,” she whimpers.
I begin pumping hard, and her gasps and groans continue.
“That’s right,” I growl. “Take it. Show me you can be a good girl.”
“Yes sir,” Jenna manages between breaths.
“Say my name,” I demand.
“Yes, Mr. Matthews,” she replied quickly. “I promise I can be good. I’ll be a good little slut just for you.”
“Good girl,” I growl. I spread her legs even farther, relishing the gasp I get in return. “This is what happens to naughty girls who sneak out dressed like sluts. They get filled with my cum.”
“Oh god, Mr. Matthews, please. Please please give me your cum—”
I spill my load with a loud groan, finally pushed over the edge by her needy whining and the sight of her massive breasts bouncing with my thrusts. I keep pumping until I can’t anymore.
I slide my cock out and watch my cum leak from her hole.
“I hope I catch you sneaking out again,” I tell her in a low voice with a smirk. “I already can’t wait to turn you into a cum dumpster again.”
Jenna flushes, a slight smile touching her lips. “Yes, sir.”
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