Chapter 34
DREW
Iwant you to fuck me.
Never have those words sounded better than they do coming from Jackson Monroe’s lips. My cock jumps at the words. The movement is so pronounced that Jackson’s eyes track it, and a startled laugh escapes him.
“Did your dick just…”
“It has a mind of its own around you,” I admit, heat creeping up my neck.
Jackson blushes too, the color spreading down his chest in a way that has me wanting to map it with my tongue. He shifts his weight, and I catch the nervous energy radiating off him.
“I’ve never…” He swallows hard. “With a guy, I mean. But I—” He looks away, then back at me with determination. “A few weeks ago, I tried. With my fingers. I couldn’t stop thinking about you, about how it would feel with your…” His eyes drop to my cock again. “Inside me.”
The image slams into me—Jackson alone in his room, fingers working inside himself, thinking about me. I surge to my feet, crowding him against the dresser.
“You fingered yourself thinking about my cock?” I growl.
He nods, pupils blown wide. “I came so hard, I saw stars.”
That’s it. That’s all I can take. I grab his hips and walk him backward until the backs of his knees hit my bed. With one gentle push, he tumbles onto the mattress, staring up at me with a mix of anticipation and nerves that makes my protective instincts roar to life.
“We’re going slow,” I tell him, already moving to my nightstand. “This is your first time, and I’m going to make it good for you, Jacky.”
I pull out the lube—thank God for my optimistic shopping habits—and a condom, setting them on the bed where he can see them. No surprises. No rushing.
Jackson props himself up on his elbows, watching me with those impossibly brown eyes. “I trust you.”
Three words. Three simple words that hit me in the heart. I lean down to kiss him, slow and deep, trying to pour everything I feel into it. When I pull back, we’re both breathing hard.
“On your back,” I murmur against his lips. “Get comfortable.”
He scoots up the bed, arranging himself against my pillows. The dried paint on his skin cracks and flakes with every movement, but neither of us cares. I grab a towel from my hamper—it’s already dirty anyway—and climb onto the bed between his legs.
“Just relax,” I tell him, uncapping the lube. The click makes him jump slightly. “I’m going to take such good care of you.”
I warm the lube between my fingers, taking my time. Jackson’s watching every movement, his cock already showing interest again despite his recent orgasm.
“Spread your legs a little more,” I coax, and he does, revealing himself to me completely.
The first touch of my slick finger to his hole makes him gasp, his whole body tensing.
“Shh,” I soothe, using my free hand to stroke his thigh.
“Breathe. I’m not going inside yet, just getting you used to being touched here. ”
I circle his entrance slowly, the tight ring of muscle fluttering under my finger. Jackson starts making these tiny noises, trying to hold back but not quite managing it. His hands fist my sheets, and I watch his face carefully for any sign of discomfort.
“It feels kinda weird,” he admits, then quickly adds, “but good weird. Keep going.”
I add more lube, probably too much, but I’d rather overdo it than risk hurting him. When I finally press the tip of one finger inside, to the first knuckle. Jackson’s back arches off the bed.
“Oh, fuck,” he gasps.
“Too much?” I freeze, ready to pull out.
“No, no, it’s…” He looks almost surprised. “Different when it’s not my own fingers.”
I push in a little deeper, watching his face intently. His brow furrows in concentration, and I can see him actively trying to relax. “You’re doing great,” I tell him, working my finger deeper. “So tight, baby. Can’t wait to feel you around my cock.”
He moans at that, his hole clenching around my finger. I start a gentle rhythm, in and out, letting him get used to the sensation. When I curl my finger, searching, his whole body spasms. “Holy shit,” he pants. “That’s—fuck, Drew!”
I press against the spot again, and Jackson makes a sound I’ve never heard from him before—raw and desperate and absolutely filthy.
I grin, adding more lube before working in a second finger.
The stretch makes him tense initially, but I keep rubbing against his prostate, and soon, he’s pushing back against my hand, chasing the sensation.
“Look at you,” I murmur, scissoring my fingers gently.
“Already so eager for it. Been thinking about this, haven’t you? About how I’d open you up?”
“Yes,” he gasps, no hesitation. “Wanted it for so long. Wanted you.”
My heart all but stops beating as I focus on making this perfect for him.
By the time I work in a third finger, Jackson’s a writhing mess.
He’s leaking all over his stomach, cock fully hard again, and the sounds he’s making are going straight to my dick.
Every time I brush his prostate, he practically levitates off the bed.
“Please,” he finally begs, reaching for me with paint-stained hands. “Drew, please, I need—”
“I know what you need.” I slowly withdraw my fingers, and he whimpers at the loss. “Gonna give it to you, baby.”
I grab the condom with shaking hands, trying not to fumble it. My cock is harder than it’s ever been, the precome dripping steadily. When I roll the condom on and slick myself up with lube, Jackson watches with hungry eyes.
“How do you want it?” he asks.
“I want to see your face.” I place his ankles on my shoulders, the position opening him up beautifully. His hole is pink and wet from my fingers, clenching on nothing, and I have to close my eyes for a second to regain control. “Ready?” I ask, lining myself up.
Jackson nods frantically, and I push forward slowly. When the head breaches him, we both groan. He’s fucking tight, even after all that prep, and I have to fight every instinct screaming at me to thrust home.
Inch by torturous inch, I slide inside. My cock is big—not Gerard big, but enough length and girth that I’m impressed that Jacky’s not running for the hills.
His face is a masterpiece of sensation. His eyebrows shoot up toward his hairline, then pinch together in the middle.
His jaw clenches, teeth bared for a split second before his mouth falls open in a silent gasp.
His eyes flutter—closed, then open, then half-lidded—pupils blown so wide I can barely see the brown.
His fingernails bite into my forearms, ten perfect crescents that’ll be there tomorrow for everyone to see.
“So big,” he gasps. “Fuck, Drew.”
“Almost there,” I promise, though I’m only halfway. “You’re doing amazing, Jacky. Taking me so well.”
Fuck. Me. I’m finally fully seated, my hips pressed against his ass. We’re both panting like we’ve run a marathon, and I can feel Jackson’s hole clenching around me, trying to adjust to the intrusion.
“Just…give me a minute,” he huffs.
I’d give him forever if he asked. The sight of him spread out beneath me, stuffed with my cock, is enough to sustain me for years. But my body has other ideas, every muscle imploring me to move, to thrust, to claim.
I focus on his face instead. The pinch between his eyebrows slowly smooths out. A flush blooms high on his cheekbones, spreading down his neck. His chest rises and falls in deeper, steadier rhythms. Then his eyes find mine, and I feel the deliberate ripple of muscle around me.
“Fuck,” I hiss, my hips jerking involuntarily.
“I think…” He clenches again, deliberately this time. “I think I’m ready.”
“You sure?”
“Yeah. Just go slow.”
Like I could do anything else.
I pull out carefully, an inch or two, then slide back in. Jackson’s eyes go wide, his mouth popping open in a perfect O of surprise.
“Oh my God,” he breathes.
I do it again, easing back until just the head of my cock catches on his rim, then slide forward with a slow, deliberate push that makes his ankles tense against my shoulders. His toes—those thick, quarterback toes—curl and twist beside my ears, knuckles going white as they grip at nothing but air.
The sight makes me grin, and I pick up a slightly faster rhythm, still careful but steady. “Good?”
He moans. “It’s—fuck, I can feel you everywhere.”
I shift my angle slightly on the next thrust, and…there. Jackson’s eyes roll back, and he makes this sound, an almost monstrous groan that I want to record and debase myself to later.
“Found it,” I say cockily, hitting the same spot again.
“Drew!”
I pick up the pace, finding that perfect angle that makes his thighs tremble against mine.
His cock slaps against his stomach with each thrust, the head glistening and purple, a thin strand of precome connecting to the puddle forming in the hollow beneath his ribs.
His breathing changes—shorter, sharper gasps punctuated by these little hitches that catch in his throat.
“Touch yourself,” I command, and he obeys immediately, wrapping a paint-stained hand around his cock.
The visual is almost too much—Jackson spread out beneath me, taking my cock perfectly while he strokes himself. It’s the hottest thing I’ve ever witnessed.
“Not gonna last,” he warns, his hand already a blur on his dick. It’s almost laughable how he’s not putting on a show, he’s not trying to impress—he’s desperate. Lost in it.
I slow down my thrusts and watch how he masturbates, how he gives himself pleasure when no one else is around.
His fist swallows the head of his cock each time, twisting slightly on the downstroke.
He alternates the rhythm, sometimes fast and ruthless, occasionally slow and cruel, like he’s fighting to draw out the pleasure but failing spectacularly.
I’ve never been more obsessed with a single human motion.
I’m leaking into the condom, but my heart is leaking all over the room.
There’s something about Jackson getting himself off while I’m inside him that’s raw and animal.
I thrust in harder, flexing my hips to hit his prostate dead-on, and he nearly doubles over, paint and sweat and lube turning the moment into a beautiful masterpiece.
My own orgasm teeters at the edge, but I force myself to hold off, ravenous for every second of this. “Want to watch you come on my cock. Want to see how tight you get.”
That finishes him. Jackson’s whole body seizes up, every muscle locking, and then he’s coming with a shout that rings in my ears. He jerks, half-lifting off the bed, and his abs contract into a hard plate.
The first pulse of his orgasm goes off like a loaded spring, launching white streaks up his own chest to his chin, splattering over the already-dried paint.
But it’s the way his eyes go wide and find mine that does me in.
He’s staring at me as though I’ve wired him directly into a mainline of pleasure, and he can’t fucking breathe.
His mouth pops open, lips trembling, and he keeps coming in these drawn-out, shuddering waves.
Suddenly, something inside me snaps. The instant Jackson’s body locks up around my cock, the floodgates open, and every trace of self-control is torched.
My animal brain takes the wheel as everything narrows to the rippling way he pulses around me and the urgent slap of my hips meeting his ass.
I rut into him in a reckless, punishing rhythm.
Jackson’s head tips back, mouth wide and wordless, every vein in his neck standing out in furious relief. He’s not even stroking his cock for pleasure anymore, just grinding out the last dregs of release, a compulsion he can’t override.
I don’t bother holding back anymore. I fuck him fast and hard, chasing the desperate, gasping noises pouring out of him. Sweat and lube and the sharp tang of latex fill the air, turning it soupy with the proof of what we’re doing.
Jackson’s hands scramble for purchase on my arms, nails raking down my forearms, leaving stinging tracks.
He drags me close, needing me on top of him, and I bow my whole body over his, pressing his knees to his chest to get the perfect angle.
My cock slams into him, bottoming out every time, and his eyes roll back again.
He’s gone from making soft noises to straight-up yelling, swearing, and babbling my name.
“Fuck, fuck, fuck, Jackson—” My voice is wrecked, raw and hoarse, but I can’t stop talking. “You feel so fucking good—can’t believe you’re letting me—fuck—oh, shit, I’m gonna blow.” The words dissolve into nothing as my balls draw up tight.
“Do it, Drew. Fill me up.” Jackson is delirious, alternating between grunts and filthy encouragements.
Suddenly, everything else drops away—my name, my major, my entire personality, as I am reduced to the singular point of where our bodies meet. Jackson’s ankles cross behind my neck, dragging me even deeper, and I swear to God, he’s trying to break me in half.
I’m reduced to nothing but “uh-uh-uh, ah-ah-ah,” and I’m not even embarrassed. My hands are everywhere—fisting his hair, raking down his sweaty chest, digging into the meat of his thighs—as I jackhammer into him. The sound of skin on skin is wet and relentless, echoing off the old plaster walls.
My climax sneaks up on me, and when I finally hit the edge, I roar, “Jackson!” and slam into him one last time.
The orgasm rips through me, intense to the point that I collapse forward, crushing Jackson beneath me and riding it out as I’m torn to pieces.
Every part of my body surrenders control.
My thighs spasm, my arms flail as my fingers claw at the headboard.
My feet kick the bed, toes struggling to grab purchase on the bedsheets.
Even my ass jiggles as my cock continues to pulse inside Jackson, filling the condom to its breaking point.
For a full thirty seconds, I can’t hear anything but my own pulse thundering in my ears.
I blink, trying to clear my head, and realize Jackson is watching me with this dazed and tender expression that makes my heart stutter and my brain reboot.
His eyes are softer than I’ve ever seen, and I get the distinct sense he’s memorizing every second of this, tucking it away for later. The funny thing is…I am too.
His ankles slip off my shoulders, and I catch them, lowering his legs gently to the bed.
Neither of us speaks because there are no words.