Helping My Gay Roommate With His Gag Reflex — Chapter 2

Everyone is 18.

Chapter 2: Two-a-Days

A few days went by before I even thought about bringing it up again. I wasn’t avoiding it, exactly, rather I just enjoyed letting Brandon stew. He kept sneaking glances, waiting for some sign that we were going to revisit “training,” but I didn’t bite. Not yet. I wanted him to simmer. Let the cucumber boy marinate.

Meanwhile, I made sure to keep things very casual. I’d lounge in my towel a little longer than necessary. Dry off a little too slowly. Leave my boxers in the middle of the floor like a breadcrumb trail of mischief. Every night I’d settle into bed, scroll through my phone, and tug on the waistband of my gym shorts just enough for Brandon to notice I was probably jerking off under the blanket, but not enough for him to be sure. He'd pretend to scroll Instagram, eyes glazed over like he was trying to read an IKEA instruction manual, and I’d stifle a smirk.

He never said anything, but the vibes? Loud.

Then came Friday night.

I’d brought someone back to the room. A girl I met at the bar with some of my friends from lacrosse. She had a great laugh and zero shame about crawling onto my bed like she’d reserved the slot. We didn’t do much beyond some vanilla sex, but it was still pretty hot, and she took a good pounding from me. I threw the condom in the trash as she got dressed.

Then the door opened.

He stood in the doorway like he’d just won a spelling bee. Big grin, backpack slung over one shoulder, an aura of post-victory glow about him. I was sitting on my bed naked, not bothering to cover up.

“I did it,” he said, as if announcing a job promotion, a bit sloppy from the party. “I sucked a cock! Start to finish!”

The girl blinked at him. I blinked at the girl. She blinked at me. Then she laughed and waved goodbye as she slipped out of the room.

I grinned. “You serious?”

“Dead serious. And he said he had never cum from oral before, but I got it done with my throat.”

"You know guys just say that to get girls to try harder, right?"

He rolled his eyes. I smiled again, happy that nothing was going to drop him from this high. 

I threw him a high-five. “I’m proud of you, man. What did I say? Natural talent.”

He plopped onto his bed, riding the thrill in his body like a parade float. But after a minute, the smile faded a little.

“You don’t wanna… see what I’ve learned, do you?”

I raised an eyebrow. My cock was still hanging half hard between my legs. “I’ve already seen you in action, man. You're a regular throat ninja.”

He looked disappointed. He really was addicted to my cock already, after just the one session. I had other plans for him though.

I gave him a look. He fidgeted.

“Did I ever tell you how I trained Chloe? Like, how we leveled up into... advanced material?”

Brandon blinked. “You mean, like... anal?”

“Yup.”

He sat up straighter. “I’ve never done that yet. Not even close. Besides shoving some household objects up there during my 'everything is sex' phase.”

“Well,” I said, stretching with a yawn, “no time like the present.”

I picked up the condom from the bin, and it was still warm.

“Welcome to college, gay boy.”

I smirked and walked over to him, gently pressing his shoulders down until he was lying on his back, just like last time.

“Warm me up,” I said, looking him in the eye. He didn’t hesitate, his hands immediately reaching for my hips. I was already semi-hard from thinking about what I was going to do to him. He opened his mouth, and I guided myself between his pink lips, watching as he eagerly swallowed me whole. His tongue swirled around the shaft, and I breathed heavy, gripping the back of his head to steady myself.

As he worked, I realized he wasn’t taking his pants off. “You can lose those,” I said, and he scrambled to do so, kicking them to the floor. His own cock slapped against his stomach, thick, pink, and already leaking. At seeing the way he reacted to me using him, I couldn’t resist. I pushed deeper into his throat, watching his body tense as he took me. His moans vibrated around me, and I glanced over to the cucumber on the nightstand. Grabbing it, I held it up so he could see as I poured the warm contents of the condom onto it, slicking it up with the remnants of my earlier load.

His eyes widened, and he moaned again around my cock, his hips shifting restlessly. I tugged his legs up, and pressed the tip of the cucumber against his little pink entrance. He tensed, but I didn’t stop.

 “Relax,” I said, pushing it in slowly, "focus on the cock in your mouth like a good boy."

His body opened for me, and I increased the pace, watching as he writhed under my battering. His throat tightened around my cock in pulses, as I continued to thrust the cucumber in and out of him, his moans turning desperate.

When I got a good rhythm going, I was ready to advance. I pulled out of his mouth and flipped him onto his stomach. My stamina was still high since I came earlier, and I wasn’t done with him yet. Gripping his hips, I guided myself into him, pushing in until I was fully sheathed in his warm and wet hole. He was plenty opened up by the cucumber. He gasped, his hands clutching the sheets, and I leaned over him, one hand wrapping around his neck.

 “You’re a good little faggot,” I muttered in his ear. His response was a broken moan, and his body arched back into me.

I pounded into him, and I was enjoying the loud slaps of my hips against his ass. When he was starting to really feel it, like I heard that only guys do, I guess from the prostate (?), he started literally begging for more, and that spurred me on. I went hard on his hole, and shoved my fingers into his mouth, letting him suck on them greedily. His body was trembling, and I just kept thrusting since I was not going to cum soon. But I sensed he was close to cumming even though he had barely touched himself.

 “Take it,” I muttered, my pace merciless. “You’re my little faggot tonight.”

He whimpered, and his body convulsed. He grabbed his shaft and squeezed, as if trying to hold off, but I didn't stop thrusting, and he came forcefully, getting it on his neck and chest and the bed below him.

I picked up my pace, and followed soon after, my thickness pulsing inside his tight hole, as he lay there with his mouth open. I pulled out, separating my muscular body from his slender frame, and watched proudly as my load dripped out. He collapsed onto the bed, breathing heavily.

 “Good boy,” I said, patting his ass before settling back on my bed. He smiled weakly, and I knew he was really hooked this time.

When I laid down and started scrolling through some insta, he got up to get in my bed with me. I wasn't into the idea, but I realized that I had another load in me, so when he reached for my chest as if he wanted to cuddle, I pushed him onto his back, and lifted his legs to his shoulders.

"More...?" he muttered, a mix of concern and curiosity on his face.

"Yup."

Having a living fleshlight in my bed that could take it rough, my cock was already hard and ready for another round. I gripped his hips and slid into him without preamble, his tight hole welcoming me with little resistance. He put his hands on my chest but I grabbed his wrists to hold them above his head. His body was still warmed up and pliant from before, and I quickly set a relentless pace, my hips slapping against his ass with a steady rhythm. He whimpered into the air, his abs tensing in pulses aligned with my thrusts. His balls bounced under his hard shaft.

"Thank you," he whimpered lowly, and I looked him in the eye and smirked. It was still hot how much he wanted me.

As I pounded into him, I reached for the cucumber on the nightstand, still slick with his ass and remnants of my cum. I pressed it against his lips. After some brief hesitation, he obeyed, his mouth opening to take it.

 I shoved it into his throat, watching his eyes water as he gagged around it.

"You ever heard of two-a-days?" I muttered between breaths as I stuffed both his holes. He squirmed and moaned, grabbing whatever part of me he could in the fast movement.

His cock twitched against his stomach, already leaking again from the intensity of the action I was giving him. I kept the pace steady, fucking his ass while the cucumber bobbed in his mouth, his moans muffled around it.

After what felt like an hour of this, I could feel myself getting close again. I pulled the cucumber out, tossing it aside, and reached down to grab his dick. His body jerked at the sudden touch, and I smirked, stroking him in time with my thrusts.

 “You earned a reach-around,” I muttered, my grip firm on his shaft. He whimpered, his hips bucking into my hand as I edged him closer to another orgasm.

Just as I felt myself ready to explode, I reached up with my other hand and grabbed his neck, my fingers digging into the sweaty, cum-streaked skin. I squeezed lightly, feeling his pulse hammer under my palm as I fucked him hard and fast.

“You can cum for me now,” I growled, and he did, his body convulsing as he spilled himself onto his body. I followed right behind, my cock swelling in bursts inside him as I planted another load.

When I finally pulled out, he collapsed onto the bed, gasping for air. I wiped my hand on the sheets and smirked down at him.

“Good job," I said, patting his ass, which I was starting to admit to myself was actually kind of cute. “Now get back to your own bed.”

He nodded weakly, stumbling back to his own side of the room. I flopped down onto mine, scrolling through my phone as he drifted off, completely spent. I chuckled to myself, knowing I’d just confirmed that this year was going to be great.