Converting the Homophobes - Chapter 3: Tommy

Everyone is 18.

Chapter 3: Tommy

“I could turn any girl straight,” Tommy used to say, cracking open a Monster and tossing a football one-handed across the school courtyard like a walking stereotype. “Hell, I could turn any guy straight too,” he sometimes added, usually with a smirk that dared anyone to question what he meant.

We never did. Not seriously.

Tommy was noise. He was the loudest in the group chat, the first to jump off a roof into a pool, the one who always insisted he didn’t care what anyone thought—but somehow always noticed if people were watching.

He had this way of filling space. Loud music, louder jokes, too many colognes. He could be exhausting, but there was something magnetic about him. Like a glitch in the matrix you couldn’t stop staring at. He was the most successful with girls, even claiming to have gone all the way on several occasions. He snapped our entire friend group a pic of a girl bent over, with his dick in the foreground, and the caption read “she said yes to anal”.

So yeah, I wasn’t sure how this conversation would go.

I invited him over on a Saturday. No one else home. I cleaned the living room like it was a date even though I told myself it wasn’t.

When he showed up, he tossed his backpack on the floor and collapsed onto the couch, like my friends often do. “Got anything to eat that’s not vegan?”

I threw a bag of chips at him. “Jalapeño flavor. That’s a personality type.”

He popped a few in his mouth, then looked over. “So what’s up? You said this wasn’t a hangout-hangout.”

I sat on the arm of the chair across from him. My heart was weirdly steady. I’d had this conversation twice already. But Tommy was different. He wasn’t cautious like Jeff or eager like Jack. He was unknowable, in a way that made me wonder if he even knew himself.

“I’ve been… trying some stuff,” I said slowly. “With guys. Before college. Figuring myself out.”

Tommy blinked once. Twice. “Like gay stuff?”

“Yeah.”

He nodded like I just told him I switched shampoo brands. “So what, you and Jack?”

I raised an eyebrow. “Why does everyone guess Jack first?”

Tommy grinned. “Because he’s a horny little fucker. Plus, he’s good looking. And he thinks no one notices.”

I was thrown—not by the observation, but the way he said it. Like it was normal. Like he noticed.

I leaned forward. “So… I was wondering if you’d want to try something. No pressure. Just—open-minded stuff.”

He didn’t answer right away. He kept chewing, staring at the TV even though it was off.

Then he said, “You know, you’re not the first guy who’s asked me that.”

I blinked. “Wait, seriously?”

He finally turned toward me. “Freshman year. My cousin’s best friend. We were at his lake house, one of those weekends when no adults were around for most of the day. We drank cheap rum and pretended we were way cooler than we were. He kissed me, and I let him.”

I didn’t say anything. I didn’t want to scare it away.

“He got weird after,” Tommy went on. “Like he didn’t mean to. So I made a joke about it, and he never brought it up again.”

“Did you like it?”

Tommy shrugged. “I didn’t hate it. I didn’t… not like it. But… no, didn’t really care.”

That was probably as close to a yes as Tommy was capable of.

“Why didn’t you ever tell us about it?” I asked.

“Dude,” he said, like it should be obvious. “I play varsity football. My locker is a crime scene of Axe and insecurity. You think I can say, ‘Hey fellas, ever wondered what it’d be like to kiss your cousin’s male best friend?’”

I laughed. “Fair point.”

He looked down at his hands. “I know what I am. But you’re brave for figuring yourself out. And I respect that.”

It was the most sincere thing I’d ever heard Tommy say. That was not the surprise I expected today.

After a moment, he added, “If you’re doing some victory lap with the guys before we graduate, I don’t wanna be left out.”

“So, you wanna do something?” I asked, careful, soft.

He glanced up, smiling faintly. “Only if we can still roast each other after.”

“Non-negotiable,” I replied.

We sat closer. No rush. No jokes. When we did finally lean in—tentative, kind of clumsy—it didn’t feel like a performance. We just kissed on the lips, with only the slightest bit of tongue. It felt like two people with too much armor on, just trying to see what was underneath.

Afterward, he rested his head against the back of the couch and stared at the ceiling.

“Okay,” he said.

“Okay what?”

“Okay I get it.”

I waited.

He glanced at me, one corner of his mouth twitching. “This whole time I thought being open-minded meant not being an asshole at Pride Month. Turns out it’s about… not being an asshole to yourself, too.”

I smiled. “You always talk like you’re narrating a Nike commercial.”

“Yeah,” he said. “But I mean it.”

A beat.

“Still think you could turn me straight?” I teased.

He laughed. “Nah. I think you’ve officially entered your bisexual king arc.”

I raised my chips in a fake toast. He clinked his soda can against it.

–[]–

Tommy’s eyes locked onto mine, a flicker of something dangerous and unspoken passing between us. The air in the room felt heavy, charged with an energy that made my skin tingle. He leaned back on the couch, his muscular frame relaxed but his expression sharp, calculating. 

“So,” he said, his voice low, almost a growl, “you want me to show you what it’s like to be with a real man?”

My throat tightened, but I didn’t look away. “Yeah,” I managed, my voice steadier than I expected. “If you’re up for it.”

He smirked, that same cocky grin that always made my stomach twist. “Oh, I’m up for it. But I’m not gonna go easy on you. You asked for this, so you’re gonna take everything I give you.”

Before I could respond, he was on me. His hands gripped my shoulders, and in one swift motion, he flipped me onto my back on my couch. The cushions sank beneath my weight as he hovered over me, his body pressing into mine. His breath was warm against my neck, and I could feel the heat radiating off him, like a predator cornering its prey.

He didn’t hesitate. His lips crashed into mine, hard and demanding. This wasn’t tentative—this was raw, unfiltered, and assertive. His tongue forced its way into my mouth, claiming me, and I let him. My hands found his back, tracing the hard planes of muscle beneath his shirt. He broke the kiss just long enough to yank the fabric over his head, revealing his toned chest and the faint trail of hair leading down his stomach.

“Fuck,” I murmured, my fingers grazing his skin.

He chuckled darkly. “You ain’t seen nothing yet.”

With practiced ease, he unbuttoned my jeans and pulled them down, along with my boxers. It was obvious now that he was not lying about his history of fucking girls around town. His eyes raked over my exposed body, and I felt a surge of heat under his gaze. He didn’t waste time. His hand wrapped around my cock, stroking me hard and fast. I gasped, my hips bucking involuntarily. “You like that?” he growled, his voice rough with the desire to make me submit to him.

“Yes,” I breathed, my voice trembling.

He leaned down, his mouth inches from mine. “I’m just getting started.”

He pushed me further back on the couch, spreading my legs wide. His fingers teased my entrance, and I tensed, unsure. “Relax,” he ordered, his tone leaving no room for argument. “If you’re gonna do this, you’re gonna take it like a man.”

I nodded, reaching for the hidden bottle of lube in the couch, handing it to him and biting my lip as he quickly lubed me up and pressed a finger inside me. The sensation was strange, unfamiliar, but the look in his eyes—pure, unbridled dominance—kept me grounded. He added a second finger, stretching me, preparing me. My body resisted at first, but he didn’t stop, didn’t slow down. 

“You’re tight,” he muttered, “but you’ll loosen up soon enough.”

When he finally pulled his fingers out, I felt empty, aching for more. He didn’t make me wait. He positioned himself between my legs, his cock thick and heavy in his hand. He lined himself up, and I braced myself. 

“Ready?” he asked, though it wasn’t really a question.

“Yeah,” I whispered, my voice barely audible.

He pushed in, and I cried out, the pain sharp and immediate. He didn’t stop, didn’t give me time to adjust. He buried himself to the hilt, and I could feel every inch of him inside me. 

“Holy fuck,” he groaned, his head falling back. “You’re so tight.”

He started moving, his hips slamming into me with a ferocity that left me breathless. Each thrust was rough, relentless, and I could do nothing but take it. My hands gripped the cushions, my knuckles turning white as he pounded into me. Soon, the pain began to fade, replaced by a deep, throbbing pleasure that built with every stroke.

“That’s it,” he growled, his hands gripping my hips hard enough to leave bruises. “Take it. You wanted this, so fucking take it.”

I did. I took every thrust, every grunt, every ounce of his dominance, and leaned into it. My body responded to him, tightening around him as I groped his body and his muscles. He groaned, his pace faltering for just a moment. 

“Fuck, you’re gonna make me cum,” he warned, his voice ragged. It was too soon, but I also wanted to feel him throb inside me.

“Do it, Tommy,” I pleaded, my voice breaking.

With a final, balls deep thrust, he came, his release hot and filling up my hole. He collapsed on top of me, his breath coming in heavy pants. For a moment, we stayed like that, his weight pressing me into the couch, his cock still buried deep inside me.

Then he pulled out, standing up with a satisfied smirk. “Not bad,” he said, wiping his hands on his jeans. “You’ve got some potential.”

I lay there, boneless and spent, my body still throbbing from his assault. My mind was a whirlwind of emotions—shock, pleasure, and something I couldn’t quite name. It was surreal that it simply kept working every time I asked my friends to fuck me. He glanced down at me, his smirk softening into something almost affectionate. 

“You’re a mess,” he said, his voice quieter now.

He reached down, offering me his hand. I took it, letting him pull me to my feet. My legs wobbled, but he steadied me, his grip firm. 

“You good?” he asked, his eyes searching mine.

“Yeah,” I said, my voice shaky but sincere. “I’m good. Just need a towel or something.”

He nodded, his smirk returning. “You can clean up if you want, but this is just a hydration break–I’m not done with you yet.”