Converting the All-Boys School Homophobes –Chapter 1.5: Side Quest with Nick (+Audiobook)

Everyone in the story is 18 and consenting.

Note to readers: Today I've included the full audiobook of this chapter. Feel free to give feedback in the comments section or DMs: love it, hate it, needs a tweak for your preferences, etc. This will act as a preview (and beta test) of an upcoming Audio Tier, which is currently in the works (still tweaking the voice). Stay tuned, and enjoy! Cheers.

Chapter 1.5: Side Quest with Nick

The room was heavy with the scent of sweat, cum and pizza rolls, the dim glow of the TV casting flickering shadows across Jack’s bare chest as he leaned back against the headboard. His dark hair was still messy, his lips slightly parted as he chewed lazily, his eyes half-lidded with the kind of post-climax haze that made him look almost docile. An hour earlier, I had given my first blowjob to him, and even gotten him to try sucking me too. It was a surreal experience and an even more pleasant afterglow. He had just given himself another wank in front of me before the pizza rolls were even out of the oven, apparently even less inhibited than normal since the barrier I broke with him earlier in the day. He came on his tummy and wiped it off with the same crusty old tee from under his bed.

I sat cross-legged on the bed beside him, my own body still buzzing from the afternoon’s events. The memory of his cock in my mouth lingered like a secret I couldn’t quite let go of, and I found my eyes drifting down to the faint trail of hair leading to his waistband, wondering if he would be thinking about it too.

“You’re quiet,” Jack said, his voice breaking the silence like a crack in glass. He glanced at me, his blue eyes sharp despite the exhaustion. “You having any regrets?”

“Not even close,” I replied, smiling, “it was the best nut I ever had. I was more worried you were gonna think it was too gay.” 

He shrugged. “Not really gay to help each other get off. Not to me anyway.” He took another bite of a pizza roll.

My fingers toyed with the edge of the blanket, my mind already racing with the next step of my plan. Jack was just the beginning. I could still feel the weight of his body under mine, the way his hands had trembled as he held me, the taste of him on my tongue. It was addictive, dangerously so.

He raised an eyebrow as I tugged at the blanket, studying me for a moment before shrugging and reaching for another pizza roll. “Good. ‘Cause, uh… that was kinda crazy. But, like, in a good way.”

“Glad you think so,” I said, my voice light and teasing. I leaned back, letting my shoulder brush against his, feeling the warmth of his skin against mine. He didn’t pull away, and that little act of acceptance sent a thrill through me. He’s really not scared of me. Not yet.

The night stretched on, the two of us falling into a comfortable rhythm of lazy conversation and half-hearted jokes. But beneath the surface, there was an unspoken tension, at least on my end, a buzzing energy that I couldn’t ignore. I could feel it when Jack’s gaze lingered on me, the way his body shifted closer to mine when either of us moved. It was like he was testing the waters, wondering if he could go there again. Whether it was in my imagination or not, I was ready for more, and since he likes to literally jerk off every thirty minutes or so, there was always another chance with him.

But eventually, Jack’s yawns became more frequent, his eyelids drooping as the exhaustion of the day caught up with him. He flopped back onto the bed, his arm slung over his face, his chest rising and falling in a steady rhythm. He was only wearing his underwear, and his constant half erection pressed a moderately obscene bulge into the air, moving with his breaths. I sat beside him, my legs tucked under me, watching as he drifted off to sleep. His lips were slightly parted, his features softened by the dim light, and for a moment, I almost felt guilty for what I was about to do.

Almost.

As soon as I was sure he was out, I slipped off the bed, my movements careful and deliberate. I grabbed my phone from the nightstand, the screen lighting up with a single notification. A text from an unknown number, just two words: come over.

My heart leapt in my chest, and I couldn’t help the grin that spread across my face. Jack’s little brother. I had a feeling he was going to be texting me.

I glanced back at Jack, his body sprawled out on the bed, his breathing deep and even. He wouldn’t wake up. Not for this. I tiptoed to the door, pausing only to put some pajama pants on over my underwear before slipping out into the hallway. The house was quiet, the air cool against my bare skin as I made my way down the hall to the door across from the bathroom. I found Nick in the doorway, peeking his teen head with his moppy curls out, waiting for me.

The door opened almost immediately, and there he was—Jack’s little brother, his short frame leaning against the doorframe, his dark eyes glinting with mischief. He was shirtless, his chest smooth and pale, his sweatpants hanging low on his hips, the unmistakable bulge straining against the fabric. His hair was a mess, sticking up in every direction, and his lips curled into a smirk as he stepped aside to let me in.

I never knew Nick that well, except for seeing around the house when I was hanging with Jack. I always had a feeling he was as horny as his brother, never bothering to conceal an erection in his pants as he would suddenly leap through the room on his way to his bedroom or the bathroom. We had heard his porn playing when he thought we were gone, and it was always group stuff. Moans of every gender would echo through the walls and we would chuckle at his naivete, forgetting to check who else was home. He was also just as homophobic as the rest of the guys. The few times Jack did let him hang out with us, he joined in on the fratty words including the f– slur. Seeing him watching us through the window earlier was the first sign I had that maybe there was more to him. I had already had my first oral today, but the goal of converting all the fratty homophobes in my friend group still comprised my task list–but this little side quest wouldn’t distract from that.

“Took you long enough,” he whispered, his voice teasing. His eyes raked over me, taking in my bare chest, thickened with muscle compared to his physically naive frame. My pajama pants,  slung low on my hips, betrayed my growing erection. 

He looked down at my cock, then back up to my eyes. “Thought you could hang with me after you’re done with Jack.”

“He went to sleep, so…” I replied, stepping into the room and closing the door behind me. The air was thick with the scent of cologne and something else—boy bedroom smell I guess. My gaze dropped to his crotch, the bulge in his sweatpants more than enough to make me want to get on my knees again. He was shorter than Jack, but his cock… fuck.

He noticed where I was looking and chuckled, a deep, throaty chortle that sent a shiver down my spine. “I’m getting hard.”

“I don’t hate it,” I said, suddenly nervous about what was happening.

“Are you guys…” he muttered quietly, “gay?”

“Kind of, at least me,” I said, “I think Jack just went for it ‘cause I asked though.”

He looked down, a bit unsure, thinking. “I could be gay. I think. If you wanna do the same stuff with me.”

I didn’t answer. Instead, I dropped to my knees in front of him, my hands already reaching for the waistband of his sweatpants. He didn’t stop me, his hips shifting slightly as I tugged them down, his cock springing free, thick and heavy, the head already slick with precum. It was bigger and longer than Jack’s, plumper, the veins more pronounced, the tip a deep, flushed pink. It was a proper handful.

“Fuck,” I breathed, my fingers wrapping around the base, feeling the weight of him in my hand. His pubes were sparse, and I pulled his nuts out toward me. He let out a soft groan, his hips jerking forward as I leaned in, my lips parting as I took him into my mouth. His taste was familiar yet different, sweatier than his brother, more intense. His body tensed, his hands gripping my hair as I swallowed him down.

“Shit,” he whispered, his voice shaky, his hips rocking into my mouth. His cock hit the back of my throat, and I gagged slightly, pulling back and licking along the shaft before taking him in again. He was thicker than Jack, harder to take, but I didn’t care. The challenge only made me more determined, my tongue swirling around the head as I worked him deeper.

His moans grew louder, more desperate, his fingers tightening in my hair as he thrust into my mouth. I could feel the muscles in his thighs trembling, the way his breath hitched with every movement. He was close, so close, and I could feel the thrill of power coursing through me as I milked him, my lips locked around his cock, my tongue teasing the sensitive underside.

“Fuck, I’m gonna cum,” he gasped, his voice breaking, his body shaking. I didn’t stop, swallowing him deeper, my throat tightening around him as he burst, hot and thick, filling my mouth with his cum not even thirty seconds after I started. It leaked out of my mouth as his cock made it difficult to swallow, and I felt the juices dripping down my chin, the taste salty and bitter, but I didn’t care. I kept going, swallowing every drop I could, my lips still wrapped around him as he shuddered, his body going limp. He leaned forward, his hands on my shoulders after he was spent of energy.

When he finally pulled away, his big cock slick with spit and cum, he looked down at me, his eyes giddy with satisfaction. 

“Damn,” he said, his voice rough, a smirk playing on his lips. “You’re good at that.”

“That was fun,” I said.

|–[]–|

I pulled away from Nick, my lips swollen and glistening with his precum, and turned around, bending over to present my ass to him. My skin was still flushed from the heat of his mouth, my muscles taut as I spread my legs slightly, giving him a clear view of what I was offering. I glanced back over my shoulder, my eyes dark with lust, and smirked. “You can fuck me if you want. If you’re anything like your brother, you can go again in like thirty seconds.”

Nick didn’t need to be told twice. His blue eyes widened, and he was up and behind me in an instant, his cock already hard and throbbing. He spat into his hand, rubbing the saliva over his thick shaft, the pink tip glistening under the dim light of his bedroom. He pressed the head against my asshole, the warmth of his skin sending a shiver through me. I could feel the pressure as he pushed in slowly, the tightness of my body resisting at first before giving way to his girth.

“Whoa, slow down,” I murmured, my voice trembling as he stretched me wide. He pulled back, spitting again, and this time he was more cautious, easing himself in with a controlled patience that surprised me. His hands gripped my hips, his fingers digging into my skin as he pushed deeper, his breath hitching with every inch. I moaned softly, my head falling forward, his pubes brushing against the small of my back as I reached behind me to guide him by his hips. He leaned in, his chest pressing against my back, his breath hot against my ear.

“You okay?” he whispered, his voice shaky but tender. I nodded, biting my lip as he began to move, his hips rocking against me in a steady rhythm. The feeling of his cock sliding in and out of me was electric, every thrust sending jolts of pleasure through my body. I reached back again, my fingers wrapping around his thigh, pulling him closer, urging him deeper. He responded by picking up the pace, his balls slapping against my ass with a wet sound that echoed in the quiet room.

Nick’s moans grew louder, more erratic, his innocence giving way to a raw, primal need. He leaned down, his lips pressing against my back, his teeth grazing my skin as he fucked me harder, faster. His breathing was ragged, his body trembling with the effort as he lost himself in the rhythm. I could feel him getting closer, the way his thrusts became more urgent, more desperate. His cock pulsed inside me, and I knew he was about to cum. He lasted a full ninety seconds this time.

Just as he started unloading into me, his maximum thickness making me grunt a bit as I adjusted pleasurably, the door suddenly creaked open. Jack stumbled in, wearing only his underwear, his eyes wide with shock as he took in the sight of us. His mouth hung open, his face pale, his body frozen in the doorway. His gaze flickered from me to Nick, his expression a mix of confusion and something darker. His naked chest heaved as he tried to process what he was seeing, his hands clenched at his sides.

“What the fuck…” he muttered, his voice barely above a whisper. His eyes dropped to where Nick’s cock was still buried deep inside me, releasing the last pulses of his intense orgasm and I could see the way his body tensed, the way his cock hardened in his boxer briefs. The sight of his little brother fucking me seemed to ignite something in him, a spark of lust that he couldn’t ignore.

“No fair,” Jack finally said, his voice hoarse, but lightening up. “I only got a blowjob.”

Nick pulled out of me, his cock slick with sweat and precum, and I turned to face Jack, still catching my breath. “Just put it in, dude,” I said, my voice teasing but inviting. “I’m warmed up already.” With that, I leaned back and lifted up my legs, showing my fuzzy, pink, teen hole with cum leaking out of it.

Jack hesitated for only a second before stripping off his boxers and climbing onto the bed. 

“I’ve never even fucked a girl yet,” he said, but he didn’t pause once as he lined himself up with my ass, taking the place of Nick’s cock from just seconds prior.

He pushed into me with a single, smooth thrust. I gasped, my back arching as he filled me, his cock stretching me in a way that made my head spin. Nick knelt beside us, his fingers tracing the curve of my rigid cock, his touch light and teasing.

As Jack fucked me, his hips slamming into my body with a rhythm that was almost violent, Nick leaned down and took my cock into his mouth. I had a feeling it was not his first time giving head. He must have been earlier than me in his own plans to get some action from his friends. His lips were warm, his tongue swirling around the head before taking me deeper. The combined sensations were overwhelming—Jack’s cock pounding into me, Nick’s mouth working me with a skill that belied his youth. I could feel myself getting closer, my body trembling with the need to cum.

“Fuck, you’re tight,” Jack groaned, his voice raw and lusting. His hands gripped my hips tightly, giving me a sense of submissiveness as he fucked me harder, his thrusts becoming more erratic. I felt him getting closer, the way his cock pulsed more rapidly and pushed even further up inside me, the way his breathing became more ragged. Nick’s mouth continued to work me, his tongue teasing the sensitive underside of my cock, his fingers playing with my balls, making contact with Jack’s abs with each thrust.

“I’m gonna cum,” I moaned, my voice breaking as the pleasure overwhelmed me. Jack’s thrusts became more frantic, his cock slamming into me with a force that made me start to see stars. I lifted my body up into the air as I came, as Jack rapidly pounded into me with all his power, and I felt him explode inside me, his cum filling me as Nick swallowed my own release, his lips locked around me as I came in hot, thick spurts. He gulped down what he could, as some white goo dribbled out around my shaft and onto my fuzzy balls.

Jack collapsed on top of me for a moment, his body trembling, his breath hot against my neck. Nick pulled away, a smirk playing on his lips as he licked his lips. 

“Damn,” he said, his voice teasing. “It tastes better than I thought it would.”

“That didn’t seem like your first time,” I said.

“They’ve never let me swallow before,” he replied, still smirking.

“WHO??” Jack insisted between breaths, sitting up and pulling his dick out of my ass with a wet plop.

He rolled off me, his chest heaving as he tried to catch his breath. He looked over at Nick, his expression a mix of disbelief and something else—something that looked almost like admiration. 

“You’re just as fucking horny as I am,” he said, shaking his head.

Nick chuckled, his eyes sparkling with mischief. “What can I say? Guess it runs in the family.”

I lay between them, my body still tingling from the intensity of what had just happened. The air in the room was thick with the scent of sweat and sex, the afterglow settling over us like a warm blanket. I glanced at Jack, then at Nick, a smirk playing on my lips. “So… what’s next?”

|–[]–|

The room was still humming with the energy of what had just happened, the air heavy with the musk of sweat and sex. Nick’s smirk lingered, his eyes flicking between me and Jack, like he was already plotting the next move. 

I felt the weight of their gazes, the heat of their bodies still so close to mine. My heart was still racing, but there was something else now—a hunger, a curiosity about how far this could go. I glanced at Jack, his blue eyes wide with a mix of exhaustion and arousal, and then at Nick, whose expression was pure mischief.

“Can we fuck you again?” Nick asked, a pleading look in his eyes.

Before I could respond, the young guy moved, his hand sliding up my chest and pressing me back against the bed. His lips were on mine in an instant, his kiss hungry and demanding, and I could feel the way his body pressed against mine, hard and eager. My hands found his waist, pulling him closer, and I absorbed the heat radiating off him, the way his heartbeat matched my own.

Jack watched for a moment, then went to check something on his phone.

“You’re not ready for this,” Nick teased, his voice low and husky, and I could feel the way his fingers gripped my hips, holding me in place.

Nick’s hand tightened around my cock, his thumb brushing over the tip, and I could feel the way my body tensed, the way my hips bucked against his hand. He leaned in, his lips brushing against mine, and I could taste the salt of his skin, the heat of his breath.

His lips found my cock, his tongue flicking over the tip, and my body shuddered, my hips lifting off the bed. I wasn’t ready to cum again, but I was still hard as hell. His hands gripped my thighs, holding me in place, and I could feel the way his mouth moved down my shaft, taking me in deeper.

“Dude,” I gasped, my hands tangling in his hair, and I physically sensed the way his lips curved into a smile against my skin.

Nick’s hand moved lower, his fingers brushing against my entrance, and I was surprised at the way my body tensed, the way my breath hitched. He leaned in, his lips brushing against my ear, his breath hot against my skin.

Before I realized it, he was putting his dick back in me, lubed up by two loads of cum. He lasted about the same as last time, and just as he was finishing, Jack had returned, with his phone playing some very heterosexual porn.

“What the boy needs,” I said, laughing. 

My ass was getting sore to the point where I wasn’t sure I would even be able to walk right, but knowing they would only last two minutes at a time, I sucked it up and switched positions to my side, and let Jack use my hole again.

The two horny monsters went back and forth throughout the night. The room was a veritable boy sex orgy, with one butt or another bouncing in the air at any given minute, and dicks sloshing inside my ass until they were barely producing a load at all, just a few drops into my sloppy, wet ass.

The rest periods between sex sessions extended longer each time until Nick finally fell asleep next to us, just as Jack pumped his final load into me. The way Nick’s innocent face slept so peacefully after ravaging my body like an animal made me smile.

“Let’s go back to my room,” said Jack as he turned to head out to the hall, his naked little ass bouncing with each step. I covered up Nick with his blanket and followed, finding the soreness in my ass was incredible and shocking. Worth it, I thought.

I awoke the next morning on the floor of Jack’s room, the harsh sunlight reminding me I wasn’t at home. I saw Jack was awake on his bed, stroking his cock under the blanket while looking at his phone.

I sat up and rubbed my eyes. “You never stop, do you?”

He didn’t even look at me. “Nope.”

Wordlessly, I crawled over to him, and stuck my head under the blanket. He didn’t protest, but didn’t stop stroking himself. The smell hit me immediately. Boy sweat, all the saliva and cum from the night before, his balls, and my own ass covered his dick. But, I had to admit I was somewhat hooked at this point. I reached for his wrist to move his hand away, and got to work on his cock with my sore throat, feeling battered from the night before. From under the blanket, I heard the door open. I froze, for fear that it might be Jack’s mom, but he pushed my head down from over the blanket, indicating it must be his brother. I shrugged internally and continued my new hobby. 

Less than two minutes later, I had drunk two morning teen loads from my friends, and they were slouched in different spots in the room. As I wiped my face, I decided to let them in on my plans.

I looked between them, suddenly nervous again. “So, about the other guys from school. Tommy, Jordan, them?”

Jack sat up straight. “You’re not gonna try anything with them too, are you?”

“I mean—yeah. Some of them, maybe. I think a couple of them might be open to it. They just don’t have the words for it. Going to an all boys school just makes people somehow more homophobic but also more gay at the same time.”

Jack whistled, shaking his head. “That’s bold, man.”

“That’s why I need you to keep your mouth shut.” I looked right at him. “No jokes. No stories. You tell anyone, and this whole thing blows up.”

He raised his hands. “Alright, alright. I swear. My lips are sealed.” Then he grinned. “Unless it’s Nick’s, obviously.”

Nick rolled his eyes but smiled too. “Actually,” he said, “I wasn’t gonna say anything, but… I’ve got some friends. Real friends. Guys I met online and started hanging out with. They don’t go to our school. They don’t care who’s into what. You’d like them.”

I blinked. “You’ve been doing stuff like this for a while?”

Nick just nodded, calm and confident now. “Let’s just say you’re not the only one who’s been exploring quietly.”

I felt my chest loosen. The pressure—of hiding, of guessing—suddenly wasn’t just mine to carry.

“Can you introduce me?” I asked.

He smirked. “Already texting them.”

Jack threw a pillow at him. “You two are gonna turn this whole town gay.”

I intercepted the pillow, grinning. “Maybe it always was.”