Converting the Homophobes–Chapter 4: Dylan

Everyone is 18.

Chapter 4: Dylan

Out of all the guys, Dylan, the last on the list was the least likely to even be a maybe.

Not just in terms of who he was — but how tightly he clung to it. And not just to me, but to anything that veered off-script. The rest of us had always joked, flexed, ironically flirted (except in my case not so ironically), and even occasionally jerked out a load in front of one another, but Dylan never did any of that. He didn’t give an inch. He would always find a reason why he had to go home if the joking turned toward nudity or overly gay jokes. He was raised by a military dad, went to church every Sunday, never laughed at “sus” jokes, never even looked at us in the locker room. He wasn’t just straight. He was structurally reinforced.

But that didn’t mean he wasn’t fun. Dylan could be hilarious when he wanted to be — dry, sharp, unexpectedly clever. He hyped us up when we were being dumb, filmed our worst backflip attempts, dared us to sneak into the community pool after hours. He just kept a hard line when it came to anything remotely gay. It was like an unspoken rule, that maybe only I noticed, that gay jokes represented the one space that he never stepped into. It just happened to be the one space I lived in more and more.

It was like his world was built on clean lines and solid walls — taught that boys don’t cry, that pink was a “girl color,” and that gay was... not discussed. He wasn’t a bully, but there was a quiet stiffness to him, like someone who learned early on that safety meant staying silent.

So I didn’t bring it up at first.

Instead, I started small — teasing comments when we were in a group, little moments of touch, brushing shoulders, nudging knees under the table. When we played basketball and he’d clap my back after a shot, I’d leave my hand there a little too long. Just to see if he noticed.

He actually always noticed. And he always pulled away.

Meanwhile, things were ramping up with the others. Jack and I had practically developed a routine. Jack’s brother, Nick was out to other guys now and I think even his family knew. He had grown bolder than I ever expected. Jeff was quietly into it, warm and loyal. And Tommy — well, Tommy had made it a sport. Some nights we’d just look at each other and know it was “go time,” like it was on the schedule. I enjoyed Tommy teaching me how fun it can be to take orders, to do things on command, to be a pseudo-secret slut hole for another guy. I had avoided talking with any of the guys as a group about my gay adventures, even though I was cycling through them on a nearly daily basis by this point. Even though people definitely started talking about it around school, I wanted it to stay somewhat clandestine until I had achieved some sort of completion of my project. I didn’t want it to be officially open news, if that makes sense. The boys and I had developed a certain flow that was keeping me satisfied, and my boy-meter was regularly filled.

But Dylan stayed a question mark.

He wasn’t oblivious. One night after practice, he caught me on my knees in front of Jack behind the bleachers. Even though he had his shorts up before anything was revealed, Dylan got an idea of the obvious and gave me a look like I’d spat on the flag. I texted him later just to say “you good?” and he left me on read for two days.

I started to give up. Maybe he wasn’t ready. Maybe he never would be. And maybe that was ok.

–[]–

Then, mid-May, things shifted a bit.

We were out at the lake, just the two of us. He needed a buddy to go canoeing with, and he asked me. I wondered why he had to go canoeing on this specific day, but it was a chance to be alone with him, maybe clear the air a bit, and maybe get him to open up to an extent. A quiet Friday afternoon. It was cloudy, the air thick and warm, the kind of weather where you don’t know if it’s going to rain or just stay sticky all day, but at least I wouldn’t get a sunburn.

He didn’t talk much at first, we just started rowing to the far side of the lake, then came back to center when we mutually decided we needed a break, or more honestly we mutually acknowledged that my arms were going to fall off without some respite. We skipped rocks and took long sips of Gatorade like it was the only thing anchoring us to the planet.

“So,” I said eventually, “what’s been going on with you?”

He didn’t look at me. “Nothing.”

I let the silence breathe, then said, “You’ve been acting different.”

He sighed. “You’ve been acting different.”

“That’s fair.”

A long pause. Then he sat up and stretched on the edge of his canoe seat, peeled off his shirt, and let his feet dangle over the water on either side of the canoe, his crotch open wide and aimed at me. But, to him, this didn’t signal what my dirty mind would have wanted. It was a simple move — but I could read from him that it meant something. He was letting his guard down a bit, inviting me in. I stayed silent and observed the pristine quietness that we only ever experienced when we got out to the middle of that lake. The quietest place in the world.

“I don’t hate you,” he said, finally. There was a long pause, until I finally looked at him. 

He continued, “I don’t hate anyone. But all this stuff you’re doing… it freaks me out.”

“I get that.”

He stared at the water. “My cousin came out last year. Half my family stopped talking to him. My dad said it was disgusting. Like a disease.”

My mouth opened slightly at the new information. It made sense, knowing his family, and it reinforced what I had known from him all along. I didn’t say anything. I didn’t want to fill the space too fast.

“I grew up thinking it was wrong. That if you were a guy and you looked at another guy like that, something was broken inside you.”

“But do you still think that?”

He hesitated. “I don’t know what I think. I just know that every time I see you next to Jack, or hear what people are saying… I feel weird. And scared. And… mad.”

–[]–

“Mad at me?”

“No,” he said. “Mad at myself. Because sometimes I wonder what it would feel like. And then I shut it down.”

I sat next to him, close enough for our arms to brush.

“I’m not trying to change you,” I said quietly. “But I want you to know that if you ever did want to try something, you wouldn’t be alone.”

He looked at me. Really looked.

“I’m not gonna kiss you,” he said. “I don’t think I’ll ever be able to do that.”

I nodded. “There’s nothing wrong with that either.”

Then he held out his hand.

I took it. His grip reciprocated mine, warm and tight.

We sat like that, watching the ripples of the canoe in the lake, saying nothing. Just holding on.

Eventually he let go and stood up. “Let’s go.”

We did. We went into his house and ate an entire half gallon of ice cream between the two of us, while we reminisced about all the years of fun we had had in the neighborhood, and how weird it was going to be to have an entire shift of our social groups when we went off to college. I left his house around sunset, and he embraced me in a full two-armed hug on my way out. In his own way, he had opened up in exactly the way I had hoped when I started this. I didn’t need every guy in my friend group to drop their pants and have an orgasm inside me to have a positive effect against the outdated mores inherent to all-boys schools. Dylan was a good guy underneath it all, and he didn’t want to be intimate with a guy.

And I was okay with that. That night, I was sitting on my bed in boxers and an old hoodie, flipping through Reddit and feeling weirdly proud of the way things had gone. It wasn’t a win, exactly — but it was real progress. It felt real.

Still, my body had grown to expect some sort of male body in and around me on a near daily basis, and I had made no plans on this day in case my time with Dylan had gone the same way as the others. I had become spoiled, and I started getting a bit jittery. I considered sending a thirsty proposal to one of the guys, but it was already late. No one would be up right now, I thought to myself. Just when I had resigned to finding a classic tube site video and stroking an easy load onto my tummy so I could sleep, my phone buzzed.

Tommy: “Get outside. Your backyard. Sesh now.”

I laughed, dropped the phone, and dropped my boxers, throwing on some shorts. I added socks so I could most quietly sneak down the hall, and slowly crept my way into the yard, my hood over my head. I instantly loved the rush of being outside for something naughty, in the cool moonlight, wearing a pair of basketball shorts on with no underwear. I could feel the breeze tickle my balls, and realized life was kind of… perfect? I texted him I was there.

Tommy crept into the yard quietly from the back fence, approaching me with arms crossed like a smug bastard.

“Took you long enough to respond,” he said.

“Long day,” I replied.

“Well,” he said, pulling me in, “lucky for you I’m a certified end-of-day tension reliever.”

He put a hand on my throat, and I looked at him in the eyes. He didn’t squeeze–it was just a reminder of who was in charge tonight, as if there were any question.

And just like that, my boy-meter was full again.

Tommy reached for my waistband, and with one finger pulled my loose shorts and let them drop to my ankles, exposing my rock hard erection pointing up at him. He grabbed it loosely with his fingers, while I left my hands at my side, letting him inspect me. He turned me around and guided my body down to my knees, then pushed be onto all fours. He left my hoodie on, and removed my shorts and socks, tossing them to the side. I closed my eyes and took a deep breath through my nose, my hood continuing to obscure my face, my ass exposed to Tommy and the moonlight. 

Before I realized it, Tommy’s tongue was going hard on my hole. I didn’t even flinch, just instinctually leaned back into his face. I was so horny, I could tell I was even looser than normal. In less than a minute, I felt a wet cock head press into my hole, and I leaned back to let him know I was ready. He wasted no time in penetrating me, working his way into my ass in the way he knew would work best: quickly. His pace grew until I started to worry that the slapping sounds would wake someone up. I glanced up to my house as I was getting pounded, Tommy’s hands on my hips, having his way with me. I sighed in relief when I realized the closest window was my brother’s room, and he just got back today from college. He was jet lagged and he always slept like a log anyway. No worries, basically an empty room.

I leaned back into the pleasure of my hole being battered, and even started groaning. Tommy’s muted huffs and puffs told me he was going to fill me up soon, and his big cock was slamming into the best part of my insides, so I let it all out and started jerking it, quickly spilling a load onto the grass beneath me. Tommy started to cum as soon as my hole started pulsing, and I leaned back to make sure he deposited his essence as deep inside me as was possible. Just as I opened my eyes, I tilted my head in curiosity. Were the drapes in there open a minute ago?