Converting the Homophobes – Chapter 5: Tyler

Everyone is 18.

Chapter 5: Tyler

Tyler surprised me.

Not because he was down — but because of how he was down.

Unlike Dylan’s resistance or Jeff’s hesitation or even Jack’s smirking curiosity, Tyler just… showed up one day, unannounced, and said:

“I’ve been thinking about what you’ve been doing. With the guys.”

I blinked. “Okay?”

He sat down at the edge of my bed, unusually serious for someone who once tried to skateboard off a moving golf cart.

“And I want to try stuff too,” he said. “Not because I think I’m gay or whatever. But like… I just want to know what it’s like to connect like that. I’ve never really done that. Not even with girls.”

That caught me off guard. Tyler had always seemed confident — loud, wiry, always with something to prove. But beneath all that, he had this oddly monk-like quality. He didn’t party. He didn’t date. He wasn’t religious, but there was a weird purity to him, an innocence but not naivete. Like he was waiting for some invisible green light to live.

He looked at me now like I was that light.

So we kissed.

It was gentle, exploratory. Tyler’s lips were a little stiff at first, like he was thinking too hard, but then he softened into it. I could feel him adjusting — breathing through it, allowing himself to be guided. He liked being held, liked when I cupped his jaw or ran a thumb along his cheek. His hands stayed mostly in his lap, unsure of what to do. He was quiet afterward, thoughtful, like he’d just eaten something new and wasn’t sure if it agreed with him yet.

“I thought it would feel… louder,” he said.

“Louder?”

“More shocking. More wrong. But it didn’t.”

“Still motivated?” I teased.

He nodded slowly. “Yeah. Just… figuring out the shape of it.”

“Do you want to… have sex?” I ventured.

“Yeah,” he said quickly, trying to remain casual. We stood in front of each other and stripped. His tight body and blonde hair looked good. I wondered where his lack of self-assuredness came from. I was hoping that letting him fuck me would give him some confidence.

I could tell he liked being the one who was kissed. He liked being reassured. For someone who’d barely dipped a toe into intimacy, Tyler took to affection like someone who really needed it, like he’d been touch-starved for years.

When I reached for his hard dick, an enjoyable thickness in my hand, he did the same to me. We stroked each other for a bit, and absorbed the feel of each other’s touch. When I pulled the lube out of its hiding place, I sat on the couch and leaned back, lifting my legs to show him my hole.

He just stood there, his face showing uncertainty. I looked at him, waiting for him to chalk up the courage he needed, when he surprised me.

“Actually,” he started, pausing to form the words, “Can you do me?”

“Oh,” I said.

“I mean, it’s ok if you don’t want–”

“No,” I interrupted, “I just didn’t expect… aren’t you…”

“Just do it,” he said, trying to avoid any discussion about it.

I nodded, taking the lube back from him as he leaned forward onto my couch, showing his ass to me. It was round and sexy, glistening with a subtle layer of sweat, he flinched when I reached for his butt cheek, then relaxed as I began to massage it, enjoying the flesh in my hands. I got down on my knees, the natural pleaser that I am, and leaned forward to shove my tongue into him. He melted back into me, and I felt his body quiver. His breath got louder, and his hole twitched on my tongue. He was still tentative. I could tell in his body language that he was waiting to see what I would do next, holding his breath.

I leaned back and paused, still kneeling behind him, my hands gripping his hips, the smooth curve of his ass warm under my palms. I took in the view. Tyler’s back was taut, the muscles tensing as he leaned forward, his breath shallow but steady. I could feel the heat radiating from him, the faint tremble in his legs as he braced himself. His body was lean but strong, the kind of build that came from years of skateboarding and restless energy. His blonde hair stuck to the back of his neck, damp with sweat, and I traced a finger down his spine just to watch him shiver.

I’m going to make this good for him, I thought, my own heartbeat quickening. He trusted me with this, with something so raw and uncharted. I wasn’t just going to take him—I was going to show him what it meant to let go, to stop thinking so damn much.

My tongue again pressed on his hole, teasing, tasting the salt of his skin. His breath skipped a beat, and I felt him push back slightly, encouraging me. I circled him with slow, deliberate oral strokes, letting him acclimate to the sensation. His body was tight, unyielding at first, but as I deepened the pressure, I felt him relax inch by inch. When I finally breached him, sliding my tongue inside, he let out a soft, broken sound that made my stomach tighten. His hands gripped the couch cushions, his knuckles white, but he didn’t pull away. If anything, he leaned into me, his hips tilting back to meet me. I pulled his butt cheeks onto my face, enjoying the smothering that his male ass gave me.

“Fuck,” he muttered, his voice strained. “That’s…”

I didn’t let him finish. Instead, I pressed deeper, my tongue working him open, savoring the way his body responded to me. His hole twitched around me as his meat globes enveloped my face, clenching and releasing in a rhythm that felt almost involuntary. I reached around, wrapping my hand on his shaft, warn, throbbing and leaking. His breath caught, and he thrust into my hand, his movements clumsy but desperate.

“Easy,” I murmured against him, pulling back just enough to speak.

He nodded, his head hanging low, his shoulders rising and falling with each ragged breath. I returned to him, my tongue and fingers working in tandem now. I pressed a slick finger against his entrance, feeling him tense for a moment before giving way. He was tight, almost painfully so, but the way he moaned told me he wanted it. I pushed in slowly, inch by inch, until my finger was buried inside him. His body clenched around me, and I could feel the heat of him, the way he pulsed with every heartbeat.

“Shit,” he breathed, his voice trembling. “That’s… it’s…”

“Good?” I asked, curling my finger just enough to make him gasp.

“Yeah,” he choked out. “Fuck, yeah.”

I added a second finger, stretching him carefully, feeling him resist at first before yielding to me. His body was learning, adapting, and I could feel the moment it clicked for him, the way he began to move back against my hand, seeking more. His cock was slick in my other hand, and I stroked him in time with my fingers, the rhythm coaxing moans from him that were far less restrained now.

“You’re doing good, dude” I murmured, my lips brushing against the curve of his ass. 

He nodded, his breath coming in short, uneven bursts. I could feel his body trembling, the tension in his muscles coiling tighter with each passing second. I didn’t want to rush him, but I could tell he was close, his cock throbbing in my hand, his hole clenching around my fingers as if begging for more.

When I finally pulled back, he let out a soft, frustrated sound, his hips jerking forward as if chasing the sensation. I stood, my own cock hard and aching, and pressed against him, my body flush with his. He was taller than me, but in this moment, he felt small, vulnerable in a way that made my chest tighten.

“You ready?” I asked, my voice low, my lips brushing against the shell of his ear.

He nodded, his breath hitching. “Yeah. Just… go slow.” It was almost a question.

“Yeah,” I promised, reaching for the lube. I slicked myself up, the coolness of the gel a sharp contrast to the heat of my skin. I pressed against him, my cock nudging against his entrance, and felt him tense for a moment before forcing himself to relax.

I’m going to ruin him. The thought was both thrilling and terrifying. He’s never going to be the same after this.

I pushed in slowly, feeling his body resist before giving way. He was impossibly tight, the heat of him searing, and knowing what he was feeling based on my own recent initiation, I had to fight the urge to bury myself in him all at once. He let out a low, pained sound, and I froze, my hands gripping his hips.

“Okay?” I asked, my voice strained.

“Yeah,” he said, his voice shaky but determined. “Just… give me a second.”

I waited, breathing through the need to move, to claim him. When he finally gave a small nod, I pushed in a little further, feeling him stretch around me, watching his ass part around my flesh, his body adjusting inch by inch. When I was fully sheathed inside him, I let out a shuddering breath, my forehead resting against his back.

“Fuck,” I muttered, my hands tightening on his hips. “You feel so fucking good.” I had not topped much at all. But with someone like Tyler, it seemed natural.

He didn’t say anything, but I could feel his body trembling, could hear the way his breath hitched as I began to move. I started slow, shallow thrusts that made him gasp, his hands gripping the couch cushions so tightly his knuckles turned white. But as I picked up the pace, he began to move with me, his hips rocking back to meet mine in a rhythm that felt almost instinctive.

“Yeah,” I murmured, my voice low. I could see in his movements the same learning curve that I had experienced when I started this experiment. “Just like that. Let go.”

He did, his body opening to me, his moans growing louder, more unrestrained. I could feel the tension in him building, getting tighter with each thrust, and I knew he was close already. I reached around, wrapping my hand around his cock, and stroked him in time with my thrusts. His breath caught, and he let out a broken, desperate sound, his body jerking as he came, his cum spilling over my hand and the couch.

I didn’t last much longer, the heat of him, the way his hole pulsed around me, pushing me over the edge. I came hard, my hips jerking forward as I buried myself in him, my own release sharp and overwhelming.

For a moment, neither of us moved, the only sound in the room our ragged breathing. Then, slowly, I pulled out, feeling him wince slightly. He turned to face me, his eyes relaxed and hooded, his expression unreadable.

“So,” he said, his voice rough but steady, “that’s what it feels like.”

I nodded, my own voice still catching in my throat. “Yeah. That’s what it feels like.”

He ran a hand through his hair, thinking. “It was… better than I thought it’d be.”

“Good,” I said, my own smile widening.

Just as I leaned forward, lifting his legs to put my dick back inside him—of course—Tommy showed up. And Jack was with him.