Recap: Jason sent me a video of himself getting spit-roasted by two pornstars, like it was no big deal. I was jerking off to it when Drew walked in. Instead of getting mad, he dropped to his knees and started blowing me. And after? He said he wanted to try bottoming. For the first time. With me. He was serious. Nervous, maybe. But curious. And willing.
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Drew shifted closer, hand still wrapped around me. “What if you fucked me?”
My breath caught.
He smiled, a little unsure now. “I mean, I’ve never done it before. But… fuck it, right? I wanna know. I wanna know what it feels like. What it’s like for you.”
I stared at him.
“You don’t have to,” he said quickly, eyes searching mine. “I just...if watching that turns you on, and if you’ve been thinking about what it felt like to top Jason, maybe I can give you something better.”
I sat up a little straighter. “You sure?”
He nodded. “I want to try. I trust you.”
I didn’t say anything right away.
Just stared at Drew. Bare-chested. Hair messy. His lips still glossy from sucking my cock, and now he was offering me his ass.
“Are you sure?” I asked again.
He nodded. “Yeah. I trust you.”
I leaned in and kissed him. He hesitated just for a second; then kissed me back. A little awkward at first. Then harder. Mouth open. Hand on my thigh. He pulled away for air.
“You ready?” I asked, watching him closely.
He shrugged, tried to play it cool. “I mean… how hard can it be?”
I raised an eyebrow.
He laughed. “Oh - I don’t mean your cock. That thing looks fucking lethal right now.”
I looked down. Yeah, I was rock hard.
“C’mon,” he said, slapping my thigh. “Let’s move this to the bedroom. We don’t want my first time to be uncomfortable on the couch.”
“Look at you,” I teased. “First time bottoming and already demanding luxury.”
He stood up and started walking down the hallway, losing his clothes like it was a damn strip show. Tank top first, then compression leggings halfway down his thighs, dick swinging, that ridiculous ass leading the way.
“Don’t get used to this,” he called over his shoulder. “This is a one-time experiment.”
I smirked and followed him.
By the time I got to the bedroom, he was already lying on the bed on his back ...naked, looking confused.
“So uh… what do I do?”
I walked to the foot of the bed and tilted my head. “Roll onto your stomach.”
He did.
I grabbed a pillow from the side, lifted his hips gently, and shoved it under his waist. “There,” I said. “Elevate your fat ass.”
He laughed. “It’s not fat. It’s muscle.”
I climbed onto the bed, my knees settling between his legs, one on either side of his thick thighs. His ass arched up, round and firm, cheeks spread just enough for me to get a full view. Tight hole, slightly clenched, like it didn’t know what was coming. “For someone who calls my ass fat and jiggly,” I muttered, “you’ve got a fucking dump truck back here.”
He laughed into the sheets. “That’s what working out does, bro. It’s all pure muscle.”
“Sure,” I said, and leaned down before he could run his mouth again.
I spread his cheeks and dragged my tongue across his hole once, slow and flat. Just a taste. I felt him jump under me.
“Uh-oh,” he said, voice muffled in the sheets. “Holy fucking...Aaah...fucking Christ.”
I pulled back immediately, blinked. “What?”
He didn’t lift his head. Just groaned into the mattress.
“Everything okay?” I asked, hand resting gently on his lower back.
He turned his face to the side, eyes blown out. “That felt… too fucking good.”
I laughed, breathless. “Fuck, Drew. You scared the hell outta me.”
He laughed too, cheeks red. “No warning, man! You went straight for it.”
I grinned and lowered my head again. “What, you want me to kiss it first and ask politely?”
He mumbled something, still catching his breath.
Too late.
I spread him again and dove in. My tongue circled his hole, slow and wet, teasing the rim before dipping inside. His whole body tensed under me. Then relaxed. Then tensed again.
I ate him out like I meant it.
Licked deeper. Flattened my tongue and dragged it up. Let it flick just inside. He groaned, one hand bunching the sheets.
“F-fuck,” he muttered. “I don’t… know what to do with my hands.”
“Just hold on,” I said between licks.
He let out a sharp gasp as I pressed my tongue in deeper, flicking back and forth now. His hips shifted against the pillow. His ass started grinding up against my mouth. That cocky, competitive energy was still in him, but now it was twisted with surprise like he hadn’t expected it to feel this good. Like he was mad at himself for loving it.
“Holy shit,” he grunted. “I get why you like this now.”
I smiled against him. “Told you.”
“Bro,” he said. “You could start a religion with your tongue.”
I laughed. “Welcome to worship.”
He groaned again, deeper this time.
“Don’t stop,” he mumbled. “Just… fucking hell.”
I kept going. Ate him until his thighs were shaking, until his ass was grinding into my face like he needed more. My cock was throbbing hard between my legs, but I didn’t rush. He deserved this; his first time wasn’t gonna be some rushed porn move.
After another minute, I pulled back, breathing hard, face shiny.
“You good?” I asked.
He lifted his head slightly. “I’m… fuck. I think I’m addicted.”
I grinned. “That was just step one.”
He groaned. “Jesus.”
I reached for the lube, slicked my fingers, and glanced down at him.
“You sure you’re ready?”
He turned his face toward me. Still cocky. Still Drew. “C’mon. You’ve already made out with my hole. Let’s see what that dick does.”
Drew lay on his stomach, one arm curled under the pillow, the other bent above his head. His back muscles twitched every time I touched him. His cock was hard, pressed into the sheets, and his ass-arched perfectly with a pillow tucked underneath was already glistening from my spit.
I sat back on my knees and poured lube into my hand, rubbing my fingers together slowly.
He turned his head a little, voice muffled against the pillow. “So, like… what do I do?”
I smiled. “Just breathe.”
“I am breathing.”
“Not like that.”
I leaned forward, kissed his lower back. “Let me ease you into it.”
“Okay.” He sounded unsure. But not unwilling.
I placed one hand on his lower back, just grounding him, then used the other to circle his hole with one lubed up finger. No pressure yet; just touch.
He shifted, barely. His legs parted slightly wider on their own.
“Still good?” I asked.
He grunted. “Yeah. I think.”
I pushed just the tip in. Slowly. Gently. His whole body stilled, then tensed.
“Shit,” he muttered.
“Breathe, Drew. Breathe.”
“Yeah....uh...Yeah.”
I stayed there, letting him adjust. My free hand stroked slow lines up and down his spine. When he finally exhaled fully, I slid in a little deeper.
His hole clenched around my finger like it didn’t want to let go.
“Holy fuck,” he said into the pillow. “That’s… a lot.”
I chuckled softly. “You’ve fucked me without prepping my hole, like, how many times? Now you know.”
He groaned. “You made it look easy.”
“It’s not. But it’s worth it.”
He didn’t say anything for a minute, just lay there breathing. I moved my finger gently, letting him feel it, curling slightly. His hips shifted towards my finger.
When I slid in a second finger beside the first, he let out a surprised noise. Not pain. Not pleasure. Just raw sensation.
“Oh fuck.”
“Too much?”
“No, no. Just--feels insane.”
I kept it slow. Steady. Curling, scissoring. Watching how his body responded. There was something almost surreal about it. This man; this cocky, ripped gym owner who’d been railing me like a machine...was now face down, letting me open him up. And he was hard. Dripping. Loving it.
The video from earlier flashed back in my head. Jason...bent over, taking it from two sides, moaning like he needed it. I hadn’t been able to look away. Seeing him like that did something to me.
Not just because he was getting fucked. But because for the first time, the power had shifted. He wasn’t the top. Wasn’t in control. And fuck… it turned me on.
“Drew,” I murmured, voice low. “You’re doing so good.”
He gave a half-laugh. “Don’t make it weird.”
I smiled. “I’m serious.”
He turned his head toward me again. His expression was soft. A little flushed. Curious.
I added a third finger.
His hips jolted.
“Fuck,” he whispered. “Okay, that I felt.”
“Too much?”
“No, no.. keep going.”
I paused, letting him adjust again, then began slowly working all three fingers in and out. His body shuddered. His legs pressed into the mattress. His cock left a slick patch against the sheets.
“You’re opening up so well,” I said, almost to myself.
He groaned again. “I don’t know how you do this all the time.”
“It gets easier,” I whispered, twisting my fingers gently. “It gets better.”
“I’m gonna lose my fucking mind,” he muttered.
I kissed his lower back. “Good.”
We stayed like that for a few more minutes...him face-down, moaning softly, and me easing him open one stroke at a time.
When I finally pulled out, his hole clenched after me, twitching around nothing. His cock was still rock hard, leaking against the sheets.
I kissed the back of his thigh and whispered, “You ready for my cock now?”
He turned his head again, lips parted. “Yeah. I think I am.”
I reached for the lube again, drizzling a slow line down the crack of his ass . It slid over his rim, catching in the slick he'd already soaked up. I stroked myself with one hand, thick and aching and drizzled lot of lube over my cock and rubbed it. My other hand was rested on his lower back, steadying both of us.
“You sure?” I murmured, leaning over him.
He nodded once, cheek still pressed to the pillow. “I want to feel it.”
I lined myself up, nudged the head of my cock right against him, and paused. His body tensed just slightly.
“I’ll go slow,” I said. “Just breathe.”
“I am breathing,” he shot back...gruff, almost annoyed but I could hear the nerves beneath it.
I laughed quietly under my breath. “Right.”
I pushed my cock in.
Just the tip. Just enough to feel that first tight resistance around the head of my cock. Drew grunted low, his hips shifting once but not pulling away. I rubbed his back in slow, calming circles and waited.
“You okay?”
“…Yeah,” he said after a beat. “Keep going.”
So I did. Inch by inch. His hole stretched around me, clenching tight, hot and brand-new. My cock pulsed as I sank deeper, the grip of him unreal. By the time I bottomed out, he let out a shaky breath that sounded part pain, part disbelief, part fuck yes.
He buried his face in the pillow again. “You weren’t lying. You’re not that big… but fuck.”
I laughed under my breath and gave his ass a light slap. “Wow. Rude.”
Before he could say anything smart, I pulled back and slammed in a little harder.
His whole body jolted. “Uh-oo-ahh--fuckkkk-”
I grinned, staying deep. “Still think I’ve got a small dick?”
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