Part 5: Every Night Before Bed
I lay there, chest still rising and falling, cock half-hard and slick with spit, when the door creaked open again.
Oliver stepped in—and I froze.
He was wearing a jockstrap.
Just a fucking jockstrap. Tight, black, hugging his ass, the strap cutting under those soft cheeks like it was made for him. His dick was already hard, poking up toward his stomach. He looked nothing like the shy little nerd I’d moved in with. This version? He knew what he was doing.
And in his hand? A small bottle of lube and a foil-wrapped condom.
“You ready?” he asked, voice low.
I sat up, my cock twitching at the sight of him. “You’re not real.”
He smirked. “Come find out.”
I didn’t need more of an invitation.
He tossed the lube and condom onto the couch and climbed on top, straddling my lap like it was his new favorite seat. That jockstrap left nothing to the imagination—his cock was throbbing, his skin flushed, and when he ground down against mine, we both let out a sharp breath.
“Miss me?” he asked.
I laughed, rough. “You been hiding this the whole time?”
“Call it long-term planning.”
He leaned in, kissing me hard, teeth and tongue and hunger. My hands found his ass, gripping it through the straps, kneading that perfect bounce as I rocked up into him.
“You brought everything,” I muttered.
“I came prepared.”
I grabbed the condom, tore it open, and rolled it on while he slicked me up with lube—slow strokes, teasing, watching me twitch with every touch. His fingers were slick and steady, and when he reached back to lube himself up, I could barely keep my hands off.
He knelt over me, steadying himself with a hand on my chest. And then I felt it—him lining himself up, the head of my cock pressing against his entrance.
“You sure?” I asked, my voice hoarse.
He looked me dead in the eyes. “Been sure for weeks.”
And then he sank down.
Fuck.
My hands flew to his hips, steadying him as he took my cock inch by inch. He was tight, warm, perfect. His mouth parted, a deep moan spilling out as he lowered himself until I was buried fully inside him.
He stayed there a second, adjusting, breathing.
“Fuck, you feel huge,” he panted.
“You feel incredible.”
He started to move—slow at first, his thighs flexing, rolling his hips in smooth, careful motions. Every drag of my cock had us both cursing. His head fell back, sweat beading down his neck, lips parted in bliss.
I watched, mesmerized, as he rode me.
This wasn’t awkward. This wasn’t shy. This was controlled. Confident. Filthy.
“You’re taking me so well,” I groaned. “Fucking riding me like you were made for it.”
He leaned forward, bracing himself with a hand on my chest, the other grabbing the headboard for leverage. And then he picked up the pace.
The sound of skin slapping, the creak of the bed, our moans—everything blended into a rhythm, raw and desperate.
I reached up, grabbed his waist, and started to thrust up into him from below. Deep. Hard. He gasped, his legs shaking, his cock bouncing against his abs, leaking pre-cum like a damn faucet.
“Dan—fuck—don’t stop,” he cried.
“Not a chance.”
I sat up, wrapped my arms around him, and flipped us, pressing him flat onto the mattress without ever pulling out. Now I was on top—driving into him, hips slamming, sweat dripping onto his chest.
He wrapped his legs around my waist, ankles locking behind my back.
I leaned in, bit his neck, and growled, “You love this?”
“Yes,” he moaned. “Harder—please.”
So I gave it to him.
Thrust after thrust, his body arching into mine, fingernails dragging down my back. His moans got louder, his cock twitching between us, untouched but close. His cheeks were pink, his mouth wrecked, and every sound he made just pushed me closer to the edge.
I reached between us and stroked him, fast and rough.
That was all it took.
He shouted my name, his whole body tensing as he came hard—thick, white ropes shooting across his chest and belly, his walls tightening around my cock like a fucking vice.
I lost it.
I buried myself deep and came hard, groaning into his neck, hips bucking as I emptied into the condom, wave after wave of release hitting me like a truck.
I collapsed next to him, both of us panting, drenched in sweat, cum everywhere.
We lay there, catching our breath. His leg was still hooked around mine, his jockstrap hanging off one thigh, and his smile was lazy and smug.
“So…” he said after a minute, voice wrecked. “Every night before bed.”
I turned my head, grinning. “And every morning.”
He laughed, resting a hand on my stomach. “You better keep up.”
“You better,” I said, kissing his temple. “I’d love to unload after a stressful day.”
He chuckled again, then looked me in the eye.
“I’m serious about the ‘minimum,’” he said, tone dropping. “Once every night.”
I raised an eyebrow. “Just once?”
Author Note:
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