Frat Boy Prepares to Get Pegged

The rumor mill in the frat house was grinding faster than ever, and this time, the story wasn't about some wild party or a half-naked girl on the roof.

It was about me.

They all knew I was the most sexually adventurous guy on campus, the guy who had experimented with everything from threesomes to public sex. But this time, the gossip was about me getting pegged by my girlfriend on Saturday night. And that was the part that had the whole house divided.

Down in the basement, a group of guys—let's call them the "Alpha Squad"—were slapping their knees and cackling like hyenas. They were mocking me, calling me a faggot, a traitor to the brotherhood. "Dylan? Getting fucked by his own girlfriend?" one of them jeered. "The King of the Hill is finally taking it from the bottom. Please."

On the other side of the room, the guys who were always down for a good time—the ones who were actually my friends—were egging me on. Tom, my best friend, was the loudest of them. "You gotta do it, man," he said, clapping me on the back. "It’s a new experience. Embrace it. Show us what you got."

I sat on the edge of the couch, nursing a beer, trying to look cool but feeling the heat rising in my cheeks. I was the most sexually adventurous guy they knew, always trying new positions, always experimenting. But this? This was outside even my comfort zone.

The truth was, I had made a deal with my girlfriend. She had agreed to let me fuck her in the ass this Saturday night, but only if I could take it first. She wanted to see me take it up the ass just to prove she was the dominant one in the relationship, just to see if I had what it took to be on the bottom.

The thought of sitting there with a giant dildo up my ass while she laughed at me terrified me, but the thought of burying my cock in her tight little hole made me harder than anything else. But the fear of being called a sissy was real.

That Friday night, Tom showed up at my door with a heavy-duty cardboard box. "Alright, big guy," Tom said, kicking the door shut behind him. "Let's get you ready."

I rolled my eyes. "You really dragged all of them out here?"

"Yeah," Tom said, grinning. "A few of us are staying over. We’re gonna help you prep. Get you loosened up. Get you in the mood. It’s gonna be epic."

It was a ridiculous scene. The guys gathered in my bedroom, sitting on the floor, the floorboards groaning under the weight of six college guys and a mountain of beer cans. We sat around and drank for a couple of hours, the air thick with the smell of stale beer and anticipation. We laughed about how silly this was going to be. They hypothesized about the size of the toys. "She’s just gonna use a small dildo, right?" someone asked.

I sighed, taking a swig of my beer. "She said she’d start small. But I don’t want to seem weak. I don’t want to get up there and say I can’t take it. I want to be able to give her everything. I want to be able to fuck her in the ass, you know? I want to give her everything."

The guys nodded in sympathy. They knew the struggle. They knew the fear of not living up to expectations.

After we’d been drinking for about two hours, the buzz had really set in. The room felt warmer, the laughter more boisterous. I stood up, my knees slightly unsteady. "I'm ready," I said, my voice a little louder than usual. "Let's do this."

Tom reached into the box and pulled out a sleek, chrome contraption. It was a fuck machine. It had a heavy base, a long, telescoping rod, and a motor that hummed with a low, menacing power. It looked like something out of a sci-fi horror movie, but it was terrifyingly practical.

"What the fuck is that?" I asked, backing up a step. I stared at the machine, my eyes wide.

"That," Tom said, holding it up like a trophy, "is a fuck machine. It’s better than you fucking yourself with a dildo. It’s more realistic. It gives you total control to just let go and enjoy it."

I looked at the machine, then at the guys. I thought about Saturday night. I thought about my girlfriend. I thought about the embarrassment of failing. The logic somehow made sense. I picked up a beer from the table and chugged it. "Okay," I said, wiping my mouth. "If you're gonna do it, pour me another beer. Then tie me down tight so that I can't chicken out and get away."

We got to work. They secured me to the bed, my wrists and ankles tied to the bedposts. The restraints were soft leather, but they were tight enough to keep me from moving. My ass was in the air. Tom set up the machine near the foot of the bed, aligning the rod with my face-down-ass-up form. We lubed up the toy—a medium-sized dildo with a realistic curve—and then they lubed up my ass.

The cool lube contrasted sharply with the heat of my body. I felt exposed, vulnerable, and incredibly turned on. I looked up at the guys, my eyes wide with anticipation.

The machine started. It was a low, steady hum. The dildo slid into me, filling me completely. At first, I winced, my body tensing. The feeling was intense, foreign. But then, I remembered Tom's words: just let go. I took a deep breath, forcing my muscles to relax. As I did, the sensation shifted from pain to pleasure. The machine began to move, a rhythmic thrusting that was relentless and powerful. It didn't tire. It didn't get bored. It just kept going.

I moaned, my head falling into the pillow. I was being fucked, and it felt amazing. I closed my eyes, letting the machine take control. The machine was a machine, after all. It didn't care about my ego. It didn't care about being "gay." It just wanted to fuck.

After about seven or eight minutes, the machine was hitting that perfect spot. I was panting, my chest heaving. The sensation was overwhelming. I looked up at the guys, my eyes glazed over with lust. "Okay," I gasped, my voice barely a whisper. "I need a bigger toy."

The guys exchanged a look. "You sure?" Tom asked. "This one is pretty big."

"Fix it up," I insisted. "I want more."

They stopped the machine and swapped out the dildo for a larger, thicker one. It was a monster, a 10-inch monstrosity with a girth that made even the guys stare. They fixed it up on the machine. I took a deep breath, bracing myself.

The machine started again. The new size stretched me further, filling me in ways I hadn't known was possible. I let out a guttural moan, my back arching off the bed. I was in heaven. I was being drilled by a machine, and I loved it.

"Somebody get another beer," I shouted. "Pour it down my throat."

They did. The cold beer splashed onto my chest and stomach, mixing with the sweat that was already coating my skin. I chugged it, the alcohol adding to my intoxication. I looked at the guys, my eyes wide. "Okay, you fuckers," I said, my voice husky. "Everybody get naked. I'm not going to be the only one who's going to going through this."

The guys looked at each other, surprised but eager. They stripped off their shirts and pants, revealing their hard, dripping cocks. I watched them, my mouth watering. The sight of my friends, naked and aroused, only added to the visual feast. I pointed to the machine. "Do it. Keep going."

The machine continued to pound me, the rhythm relentless. The guys circled me, their eyes locked on my body. They watched the dildo slide in and out of my hole, the wet, sloppy sound echoing through the room. They were captivated by the curve of my ass, the way my muscles clenched and unclenched with each thrust. It was a beautiful sight. And the sight of my own massive erection, standing at attention, only added to the visual feast.

I started saying that I needed more lube, so they stopped the machine. They were about to lube me up, but I said, "You know what, let's just go for the biggest toy." They took out the biggest toy, this giant 14-inch cock, the thickness of an arm. Everybody's laughing at how ridiculous it is, but my hole seemed to swallow it up. I chugged another beer, and the sight of this was enough to drive everybody crazy. All of my friends were jerking off.

The machine groaned as it adjusted to the new size. The big 14-inch toy was a beast, a massive slab of silicone that looked like it belonged on a king. The guys laughed, shaking their heads. "Look at that," they said. "He's taking it all. He's a machine himself."

I, however, was in a trance. The feeling of being stretched so wide, of being filled to the brim, was intoxicating. I looked up at the guys, my eyes glazed over with lust. "More," I breathed.

They lubed me up again, the thick, sticky fluid coating my entire body. The machine began to move again, the 14-inch dildo plunging deep inside me. It was too much, yet it was exactly what I needed. I screamed, my back arching off the bed. The machine was relentless, pounding me into the mattress, leaving me gasping for air. The machine was a machine, and it was giving me the fucking of my life.

The guys were mesmerized. They couldn't take their eyes off me. They watched my ass swallow the massive dildo, my hole pulsing and throbbing around it. They were so turned on by the sight that they started to touch themselves. Their hands moved over their cocks, stroking them faster and faster. The room was filled with the sounds of our heavy breathing, the whir of the machine, and the wet, slapping sounds of the dildo entering and leaving my body. They were jerking off furiously, watching the machine piston in and out of my stretched-out hole, drooling over the spectacle.

Just as I groaned, "Hey, I need some more lube," the first guy didn't wait for a bottle. He whipped it out and blasted a thick rope of hot jizz right onto the dildo, coating it in white cream. "Dude, your cum is going up my ass," I gasped, feeling the warmth of his load being pushed into my hole by the machine.

Suddenly, the door to the bedroom burst open. The guys from the kitchen—the ones who had been mocking me just minutes earlier—stumbled in. They stopped dead in their tracks, eyes wide as saucers. The whole room went silent as they took in the sight: me, tied to the bed, my body glistening with a mixture of sweat and lube, the machine pounding me relentlessly, and my friends surrounding me, jerking off furiously.

The first of the "mockers," Chad, stepped forward, his chest heaving like he’d just run a sprint. He couldn’t believe his eyes. He stared at me, then at the machine, his pupils blown wide. He felt a strange mix of jealousy and curiosity as he looked at the dildo, now slick with lube and sweat, and the sight of my hole, now stretched wide and gaping, raw and red, pulsing and hungry, looking like a perfect little rosebud waiting to be plundered. "Hey, I need lube, Chad," I moaned, my voice breathless, my body trembling with pleasure as the machine drove the toy deeper.

Chad didn’t wait. He grabbed a bottle of lube from the table and squeezed a thick glob onto the toy, his hand lingering on the chrome shaft before he stripped off his pants. He grabbed his own cock, which was already rock hard, weeping pre-cum. He stood over me, aiming his dick right at the dildo. He pumped his shaft furiously, stroking himself with wild abandon, his knuckles turning white, his breathing ragged. Then, with a guttural grunt and a flick of his wrist, he shot his load.

The hot, white fluid spurted onto the dildo, coating it in thick essence. It mixed with the lube and my sweat, creating a slurry of sexual fluids that looked obscene. I felt it instantly—the warmth splashing against my sensitive skin as the machine drove the toy in and out again. I looked up at Chad, my eyes wide, feeling the heat of his seed mixing with the cold lube, making me feel incredibly full and used.

"Dude, your cum is going up my ass," I gasped, my body arching off the mattress.

Chad smiled, a wicked, predatory grin. "Yeah, but I never busted a nut in a dude, so it ain't gay. I just added my load to the party." He wiped his hand on my leg and went back to jerking off, watching his seed mix with mine.

The room went silent for a moment. The other guys looked at each other, stunned. They saw the look of ecstasy on my face. They saw the way my body reacted to the machine and the cum. They saw the sheer debauchery of the scene. And they started to get turned on. They couldn't help it.

"What's it like?" one of the guys asked, his voice trembling. "Having a load of cum up your ass?"

I chuckled, a low, husky sound. "It's actually kind of hot," I said. "It's warm and thick and filling. It feels like... I don't know. It feels right."

The chain reaction was immediate, violent, and utterly shameless. The guys who had been watching didn't just start jerking off; they attacked their cocks. They didn’t care about the "gay" label anymore, or maybe they never did. They just wanted to add their own contribution to the feast. They pumped their shafts furiously, fisting their meat until their knuckles turned white, their bodies trembling with pure, unadulterated lust. They shot their loads, hot streams of jizz splashing onto the dildo and directly into my body, coating the silicone dildo and filling me up with their essence. The room was instantly filled with the overpowering smell of sex, sweat, and semen. The air was thick enough to chew on, heavy with the sound of our breathing, the wet slapping of the machine, and the wet squelching of my used hole.

After an hour and a half of getting absolutely wrecked by the machine, my whole body was wet and sloppy with cum. I was covered in sweat, lube, and the jizz of my friends. I looked like a total mess, glazed and dripping, but I looked happier than I ever had in my life. I felt full, stretched, and completely satisfied. The machine slowed down, its rhythmic pounding fading into a slow, pulsing rhythm, and finally stopped, leaving me panting, my body trembling as the cold air hit my overheated skin.

The guys stood around me, their cocks still hard, their chests heaving. They looked at me with awe. They had never seen anything like it. They had never seen me take so much. They had never seen me enjoy it so much.

I looked up at them, my eyes glazed over with pleasure. I smiled. "I'm ready for a pegging by my girlfriend," I said. "But," I added, a mischievous glint returning to my eyes. "You guys think you can keep me in practice for the next time that she wants to peg me?"

The guys looked at each other, then back at me. With a nod and a smiled, they agreed. "Yeah," Tom said. "We'll keep you in practice. Every Friday night."