Converting the All-Boys School Homophobes (+Audiobook)

Everyone is 18.

Note to readers: Today I've included the full audiobook of this chapter. Feel free to give feedback in the comments section: 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: Jack

Before I left for college, I wanted to have my first sexual experience. My friends had all had girlfriends at one point or another, so they had all gotten some action at least. But we went to an all-boys school, and I never really wanted a girlfriend–I just wanted someone, anyone to touch my dick. When I looked at porn, I was even drawn to the gay category sometimes. I could picture myself in a room with a bunch of sweaty guys as we took turns using the mouth of some twink on his knees with a leash tied to his neck collar, or even being the twink in the middle. I certainly had the body for it. 

I had never admitted any of this to my friends. Most of them were pretty classically homophobic, with frequent gay jokes and even using the f– slur from time to time. We had certainly jerked off in the same room as others in the group over the years, but it was strictly business, making sure our eyes were focused on the titties on the screen, even if I was sometimes unable to resist the urge to peak at their cocks.

Their general uneasiness around the idea of gay people existing made me question my plans, but in my small town on a lake, the fact that we were a tight knight group made them my best chance of getting some action before high school. Part of me also wanted to show them that being gay wouldn’t be so bad. And, honestly, I wanted to prove it to myself too.

The first on my list was Jack. Little Jackybear. He was the horniest one of the bunch, and he lived the closest. At one point I’m sure I had seen his boner more times than I had seen my own. He was an overly hormonal teen with a priapistic, constant need to jerk off. Literally every time we hung out, either one-on-one or as a group, he would stand up at least once, lean his dick forward and show his boner through his pants, say “aight I gotta jerk off” and leave the room. If it was a sleepover, he often wouldn’t even leave the room, just whip it out and give himself a quick handy into a tissue or on his hand. The other guys would roll their eyes, but to me he was the perfect place to start.

His body was diminutive, smaller than the rest of us, but his dick was on the larger side. His little brother was short too, and also had a big dick. I only knew this because I walked in on them having a certain kind of contest one time. If my plan was going to work at all, it would work on Jack. Since he lived two doors down from me, I set my plan in motion one day in April of my senior year. 

|–[]–|

“Dude, Cody, what the fuck are you doing?” Jack’s voice cracked, half-laughing, half-panicked, as my lips grazed the base of his cock. His hands hovered above my head, unsure whether to push me away or grab hold of something—anything—to steady himself. His dick twitched in my hand, thick and warm, the veins pulsing under my fingertips. I could feel the tension in his thighs as he stood there, his boxers pooled around his ankles, his pale skin flushed pink with a mix of embarrassment and something else.

I looked up at him, my lips still inches from his shaft, and gave him a small, knowing smirk. 

“What does it look like I’m doing? You’re always saying you need to jerk off. I’m just… helping out.” My voice was calm, almost teasing, but inside, my heart was pounding. This was it. My first time. My first time with a guy. And it was Jack—Little Jackybear—the one who couldn’t go two hours without pulling his dick out.

His eyes widened, and for a moment, he didn’t say anything. Then, slowly, his hands dropped to his sides. “You’re… serious?” he asked, his voice trembling. His cock twitched again, betraying his words.

I didn’t answer. Instead, I leaned in and took him into my mouth, feeling the warmth of his skin against my tongue. He let out a sharp gasp, his hips jerking forward instinctively. His hands shot to my shoulders, gripping them tightly as I began to move, slowly at first, then with more confidence. His taste was salty, musky, and every nerve in my body was on fire. I could feel his tension melting away as his hands relaxed their grip, sliding down to rest on my back.

|–[]–|

It started earlier that day, when I walked over to Jack’s house with the plan brewing in my head. The sun was high, casting a golden glow over the lake connected to his backyard. I found him in his room, sprawled out on his bed, shirtless, scrolling through his phone. His small frame looked almost delicate in the dim light, his pale skin smooth and unblemished. His dark, wavy hair was messy, sticking up in all directions, and his blue eyes lit up when he saw me.

“Yo,” he said, sitting up. “What’s up?”

“Not much,” I replied, sitting down on the edge of his bed. I glanced at him, taking in the faintest trail of hair leading down from his navel, disappearing into the waistband of his sweatpants. My mouth went dry, knowing what I was about to ask of him. “Just… bored. Thought I’d come hang.”

Jack laughed, leaning back on his elbows. “Same. I was just thinking about jerking off, actually.”

I raised an eyebrow, pretending to be surprised. “Wow so you’re mixing it up today.”

He shrugged, grinning. “What can I say? It’s all I’ve got going for me. I don’t spend all day studying like you.”

I chuckled, but my mind was racing. This was my opening. I took a deep breath, my heart pounding in my chest. “Hey, so… what if I told you I could help with that?”

He froze, his grin fading into questioning. “What do you mean?”

I hesitated for a moment, then met his eyes. “I mean… I could take care of it for you. If you want.”

His expression shifted from confusion to disbelief. “Wait… you’re serious? You’re… into that?”

I looked at him in stillness, my cheeks burning, but my voice nonchalant. “Yeah. I mean… kind of.”

Jack stared at me for what felt like an eternity, his face unreadable. Then, slowly, he stood up and walked over to the door, locking it. “Okay,” he said, his voice low. “Let’s do it.”

|–[]–|

Now, here we were, his cock buried deep in my throat as I bobbed my head, my tongue swirling around his shaft. His breathing grew heavier, his hands gripping my hair as he thrust into my mouth. I could hear the muffled sound of his moans, feel the way his body trembled with each movement.

“Fuck,” he whispered, his voice shaking. “I can’t believe this is happening.”

I pulled back slightly, looking up at him. “You like it?”

He nodded, his cheeks flushed. “Yeah. I… I really fucking like it. Shut the fuck up.” He threw his head back and pushed my head back down onto him to bob some more. But I smiled, my lips coming back off his cock. “Good. Now it’s your turn.”

He blinked, confused. “My turn?”

I released him from my mouth and stood up, my own hardness pressing against my jeans. “Yeah. You’re going to blow me too.”

His eyes widened. “No way bro you’re on your own for that shit.” 

I advanced my finishing move. “I’ll make you cum if you do me.” 

The conundrum bounced around in his horny brain for about two seconds, before he sighed and reached for my shorts. I let him pull them down to below my balls, making my rock hard cock stick up straight toward his face. He closed his eyes in a squint and put his mouth on me tentatively. He went down a couple inches until he almost gagged and pulled back out, holding my salami in his hand from the base.

“It just tastes like skin,” he said with surprise in his voice.

“I thought the same thing,” I laughed, “Good start. I wanna go a little further.”

As his eyes widened, I pushed him down onto the bed and climbed over him, straddling his naked, teen chest. His hands instinctively went to my waist, his fingers trembling as they gripped my skin. I could see the conflict in his eyes—the fear, the curiosity.

“Hey,” I whispered, leaning down so my lips brushed against his ear. “You’re not scared, are you?”

He swallowed hard, his gaze flickering down to the big cock throbbing in his face. He had gotten it in his mouth easily, but now he was going to feel a little more. With a shaky breath, he closed his eyes and opened his mouth, freeing himself to submit to my cock. His eyes squinted tighter as I pressed into his mouth, his lips stretching around my shaft.

|–[]–|

I pulled out and let the tip of my cock rest on his lips, and felt his warm breath on my skin. I heard the tentative flick of his tongue against my tip, and I couldn’t help but glance toward the window. There, just barely visible through the crack in the curtains, was Jack’s younger brother, his face pressed against the glass of the low, first story window, his eyes wide with shock. I could see his hand was down his pants, moving furiously, and I could see the unmistakable bulge straining against the fabric.

I smirked, my gaze lingering on him for a moment, letting him get a good view of my ass and my cock going into the mouth in front of me, before I turned my attention back to Jack. “Take your time,” I murmured, running my fingers through his hair. “Make it good.”

And as Jack’s lips wrapped around me again, tentative at first but growing bolder with each passing second, I couldn’t help but think that this was just the beginning. There were so many more boys to convert, so many more mouths to explore. And I was ready for all of it.

“That’s enough,” I said, slowly pulling my shaft from his mouth, “that was awesome dude.”

“I know right?” he said.

“Thanks for doing that, I know it’s not your thing,” I said, as I squatted back down to get his cock back in my mouth.

“Honestly, it’s a fair tradeoff. Wasn’t too bad,” he said, then closed his eyes and put his hands behind his head, melting into the bed as I started again on his shaft. I got an extra special thrill, indulging in how well my plan worked out today. Maybe the rest of the guys wouldn’t be as hard as I thought. Jack was as ready to burst as I was at this point, and I stroked my shift rapidly as I pushed him toward my throat and bobbed and swallowed.

“I’m gonna cum,” he said after about fifteen seconds.

“Mmhmm,” I mumbled around his cock as I kept going. I could tell he was shocked I wanted to swallow it, but he closed his eyes, and even started touching my head for a bit as I milked his squirting cock into my mouth. It was my first taste of cum, and it came at the perfect time for me as it pushed me right over the edge, and I squirted out a load onto his bed. When I milked the last drop out of him, I swallowed it all in one gulp. The way it left a trace of cum in my mouth and throat reminded me I was different now. I was marked as a new guy. I looked up at him, his naked body, his floppy cock resting on his thigh, his red face, and I wondered what his brain was going to do now that we’d cum.

He looked at me like he was thinking about something, and tilted his head to the side. “You want pizza rolls?”