4
Tommy climbed onto the bed, positioning himself on all fours above me as I settled back against my pillows.
He backed his ass toward my face while simultaneously leaning down and taking my cock back into his mouth, and suddenly I was lying on my bed in a sixty-nine with my male roommate—his perfect, pink asshole inches from my lips while his mouth worked my shaft with the wet,
practiced hunger of someone who'd been doing this far longer than I'd been thinking about it.
I gripped his butt cheeks with both hands. Spread them. Leaned forward and dragged my tongue from his smooth taint upward, across the ridged, muscular ring of his hole, and felt him shudder from head to toe.
The taste was clean. Faintly sweet from whatever product he used with something earthy underneath. And the texture—the tight, warm, responsive pucker beneath my tongue—made something snap in my chest.
I licked again. Harder. Heard Tommy moan around my cock, felt the vibration ripple through my shaft, and the feedback loop—my tongue on his hole, his mouth on my cock—was so devastatingly good that I stopped thinking about categories altogether.
I ate him like I hated how pretty he was, gripping his cheeks hard enough to leave marks, spreading him open, burying my tongue against his asshole with a hunger I hadn't known I possessed.
I licked and sucked and pushed my tongue inside him, feeling the tight ring yield, feeling the heat beyond it, and every moan Tommy made—muffled by the cock in his mouth—drove me deeper.
I spanked him a few times—hard—and watched the pink bloom spread across his smooth cheek and felt him gasp around my shaft.
I spanked him again. Grabbed his ass in both hands and pulled him harder against my face, and the sounds I was making—wet, guttural, starving—were sounds I'd never made with any girl.
"Fuck," Tommy gasped, pulling off my cock. His voice was wrecked. "You eat ass like you've been doing it your whole life."
I didn't respond. My mouth was busy.
Eventually—after minutes that felt like hours, after Tommy had begged and writhed and pushed his ass back against my face so many times I'd lost count—he pulled away. Reached into his nightstand. And placed a bottle of lube in my hand.
"Go easy," he said, climbing off me and positioning himself on all fours at the edge of the bed.
His perfect, pink, spit-slicked hole was right there—open, waiting, glistening in the overhead light.
He looked over his shoulder at me with those blue eyes.
"You're the biggest I've ever taken. So just... be patient with me."
I looked down at my cock—huge, slick, throbbing, aimed at something I'd never aimed it at before.
I squeezed the lube and slicked my cock until it shone.
The lube was cold and the contrast against the heat of my shaft made me hiss through my teeth, but I stroked it on—base to tip, slow, thorough—watching the light catch every ridge and vein as my hand worked the slick surface.
Nine inches of hard, glistening cock, pointed at something I'd never pointed it at before.
Tommy, meanwhile, was putting on a show.
He'd squeezed lube onto his own fingers and was reaching behind himself, sliding them over his hole with a deliberate, unhurried thoroughness that was clearly as much for my benefit as his.
I watched him work the gel across the tight, pink ring until it glistened—puckered and shiny and obscenely inviting—and felt my cock throb so hard in my grip that I had to squeeze the base to keep from losing it right there.
"Finger me a couple times," Tommy said, glancing over his shoulder. "Make sure it's nice and slick inside, too."
I should have hesitated. Six hours ago, I would have. But six hours ago I hadn't had this pretty-boy’s mouth on my cock, and I hadn't eaten his ass until my jaw ached, and I hadn't already crossed so many lines that the original boundary was a dot on the horizon behind me.
I pressed my index finger against his asshole.
It yielded immediately—a soft, warm give that pulled me in—and the heat that closed around my finger was staggering.
Not warm. Hot. Tight in a way that pussy had never been—a gripping, silky, almost muscular squeeze that clung to my finger like it was trying to keep it there.
My cock jumped in my other hand.
This is going to be nothing like pussy, I thought, and the thought didn't scare me. It made me harder.
I pulled my finger out and pushed Tommy flat onto his stomach.
He went down willingly, his slim body pressing into the mattress, and lifted his hips just enough that his ass rose into a slight arch—the perfect angle, that pink, lubed hole on display between his smooth cheeks.
Prone bone position. I'd fucked girls like this a hundred times. The familiarity of the position was a lifeline my brain clung to, even as everything else about the situation screamed this is not the same.
I rubbed the tip of my cock against his hole. Slow circles. Feeling the slick heat of the ring against my head, the way it clenched and released, clenched and released, like it was breathing. Tommy moaned into the pillow and pushed back against me.
"Stop teasing," he whined. "Push it in."
"I can't," I said, and I hated the words the moment they left my mouth. "If I go in right now, I'm going to cum in about three seconds."
The admission hung in the air. Colton Asher—the guy who could last an hour with the hottest girls on campus—was confessing that a twink's asshole had him on the verge of premature ejaculation.
I hadn't worried about coming too fast since I was sixteen, but the novelty of this—the wrongness of it, the taboo, the heat—had reset my brain.
Tommy laughed softly into the pillow. "Take your time, big guy. I'm not going anywhere."
I breathed. In through my nose. Out through my mouth. Felt my pulse slow by a fraction.
Then I gripped the base of my cock—hard, firm, anchoring—and pressed the head against his hole.
It slipped off. The lube and the tightness conspired to deflect me, my cockhead skidding across his taint.
"Grip it tight and really push," Tommy coached, his voice muffled by the pillow. "Your dick is huge and I'm tight. It's going to take some work."
I repositioned. Pressed. Pushed. Felt the ring resist, then start to give—a slow, incremental yielding that gripped the head of my cock with a pressure so intense the color drained from the skin.
“Ugh…” Tommy groaned. Loud. Guttural. A sound that came from somewhere deep and made the walls of our small dorm room feel even smaller.
The sound drove me forward.
I shoved—not rough, but insistent—and felt the tightness choke around my cockhead as it breached the ring. The heat was nuclear. The squeeze was inhuman. And Tommy was moaning into the pillow with a sound that was equal parts pain and hunger.
"You okay?" I asked, my voice tight.
Tommy nodded against the pillow. "Slow..."
I was slow. But I didn't stop. I couldn't. The sensation of his body opening around me—reluctant, yielding, impossibly snug—was pulling me deeper by instinct, and my hips were moving forward in tiny, grinding pushes that fed another half-inch inside with each one.
I looked down. Watched as the head of my cock—pale, the blood squeezed out by the vise-grip of Tommy's hole—disappear fully inside him.
The visual was surreal: my cock was inside another guy. The sentence repeated in my head like a news ticker, trying to find a place to land, and finding none.
Boypussy, I thought, almost laughing at myself. That's what this is. Boypussy.
The label was ridiculous. A mental bridge I was constructing to get myself from one side of this experience to the other without having to look down at the canyon in between.
But I couldn't think about labels for long because Tommy's ass felt too fucking good to think about what any of this even meant.
I pumped; shallow, slow. Just the head and an inch or two of shaft, in and out, feeling the ring grip and release around the ridge with each stroke. Tommy huffed into the pillow, his slim back rising and falling, his fingers clutching the sheets.
"How is your dick so fucking big, you jerk," he groaned, and laughed—a breathless, half-delirious sound that made me grin despite everything.
"Want me to stop? Is it too much?"
"It hurts," Tommy said, his voice honest and raw. "But that's part of what I like. Keep going deeper. Just slow."
I pushed—Inch by inch. Feeling his body fight and yield, fight and yield, the tight canal stretching around my girth in a way that made me understand I was bigger than anything he'd taken before—bigger than the bouncer,
bigger than whoever else had been here—and the pride of that mixed with the pleasure until I couldn't separate them.
Then something opened.
A deep, interior surrender—Tommy's body giving way all at once—and my cock slid the rest of the way inside in one smooth, devastating glide.
Really, it felt like I was being sucked up inside him.
My hips pressed flush against his ass. My balls rested warm against his taint.
Nine inches of me, buried to the hilt inside the tightest, hottest thing I'd ever felt.
"Oh, fuck," I moaned, and the sound was long and low and came from somewhere I didn't recognize.
"I can feel you throbbing inside me," Tommy whispered.
He could, because I could feel it too—my heartbeat pulsing through my shaft, beating against his inner walls, and the intimacy of it—the connection, the shared pulse—was something no hookup with any girl had ever come close to.
I pulled back, added more lube, and pushed home again. Then again. Finding a rhythm—slow, deep, full-length strokes that let me feel every inch of his canal gripping my shaft.
The sounds filled the room: the wet, rhythmic slap of my hips against his ass, Tommy's muffled moans, the creak of the bed frame, and my own breathing, heavy and ragged and completely beyond my control.
It felt better than pussy.
I knew it the moment I found my pace—knew it in my bones, in the base of my spine, in the way my cock was responding to this body with a sensitivity and an intensity that years of heterosexuality hadn't prepared me for; the tightness, the heat;
the way Tommy's hole gripped every vein on the backstroke and released on the push, milking my shaft with a precision that felt almost intentional.
"Turn me over," Tommy gasped. "I want to face you. I want to see your face while you're inside me."
I hesitated. On his stomach, I could pretend.
Could focus on the ass, on the arch of his back, on the familiar mechanics of fucking from behind.
But face to face—his dick, his balls, his face right there—there'd be no pretending.
No boypussy. No bridges. Just me, inside a guy, looking him in the eyes.
"Please," Tommy said.
I pulled out. Tommy turned over on shaky legs, and what I saw—his slim body, his flushed cheeks, his small hard dick leaking against his stomach, those blue eyes looking up at me with something that was more than lust—should have made me retreat;
should have triggered every defense mechanism I'd built over years of aggressive, performative straightness.
Instead, it made me pull him closer and inhale the scent of him.
Tommy wrapped his arms around the back of my neck and climbed into my lap, straddling me, his knees planted on either side of my thighs.
He reached behind himself, found my cock, and lowered onto it with a slow, clenching slide that drew a moan from both of us—mine deep, his high, our voices braiding together in the small room.
Then he rode me.
Up and down, slow at first, then faster—his tight canal sliding along my shaft with a wet, gripping rhythm that made my eyes roll back.
His arms stayed locked around my neck, his face inches from mine, and I could see everything—the pleasure in his expression, the way his lips parted, the flush spreading down his chest.
His small dick bounced between us, rigid and dripping against my abs.
And then, without deciding to, I kissed him.
My mouth found his and the kiss was nothing I'd planned and everything I didn't know I wanted—soft and deep and tasting like lube and spit and something sweeter underneath, and Tommy moaned into it and rode me harder, grinding down, taking every inch, his ass clenching around my shaft in rhythmic,
devastating pulses that I felt in the fillings of my teeth.
"Fuck—fuck—" Tommy gasped against my mouth, and something in his voice changed. Tightened. Cracked. “What are you doing to me? I’m gonna—OH FUCK!”
His body locked.
His eyes went wide.