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Chapter 4: The Dungeon
For the next few months, I was the dungeon hole. Cal sort of gave me some space, letting me stretch out and learn my own way, but he was definitely my favorite during this period. He was key to making me into the Cupcake, and I will always be grateful to him for that. My pledge duties were different from everyone else’s. The other guys got paddled when they screwed up trivia questions or showed up late. They did pushups, ran errands, cleaned bathrooms, and hauled beer kegs up from the basement. When I messed up, the president or one of the other frat brothers would just look at me across the room and say, "Thirty minutes downstairs." Everyone in the house learned exactly what that meant within the first couple days. Nobody explained it out loud, but once they saw me in position, it was clear.
The first night I took the position, I just did what I was told. I went down into the empty basement at the assigned time, while guys were still hanging out upstairs. I knelt down against the couch. After a minute of waiting, alone, my knees got sore and I hopped up onto the couch, leaning over the back, reading lecture notes on my phone.
After a few minutes, the basement door finally opened. I didn’t look back, for some reason trying to retain some detachment from the ritual. I heard two voices, but I couldn’t place them at first.
“Oh shit, look,” one of them said, getting quiet.
It was one of my fellow pledges. I had kind of been hoping to get more attention from the older frat bros, especially Cal, but I didn’t get to choose. I was just a hole, and that was my duty to the frat.
They approached me quietly, and I heard belts unbuckle. My bare ass was sticking out, and I set down my phone, closing my eyes, getting ready to start my role.
I heard a bottle of lube click open, a squirt as it was poured out, and the squishy sound of lube being rubbed into skin. I guess they had already decided who was going first.
Suddenly there was a hand on my hip, and I flinched. The guy behind me pressed his dick against my ass, already half hard from rubbing lube into himself. He set something down on my back, and when I heard the porn sounds, I realized it was his phone playing some content for him to get off to.
I was somehow less nervous when I realized he was adding porn to the mix. I leaned back against him, silently willing him to put his dick in me and get started. He pressed forward again, popping the head of his dick into my hole. I tensed, but tried to relax as he pushed the rest into me quickly.
He grunted and breathed hard as he started humping me rapidly. It was difficult, but nothing like when Cal had fucked me. I was comparing them in my head. I reached down to squeeze my achingly hard dick. The pressure made it feel better.
“He’s jerking it!” the second guy whispered urgently, as if that mattered for some reason.
The guy fucking me went even faster, holding my hips and pulling me back into him. I had to brace myself by gripping the arm of the couch.
“Don’t cum inside him,” the second guy said, “I wanna go next.”
“Too late,” the first guy said with a squeaky, strained voice. He slowed down and pulsed inside me.
He pulled out, and I felt empty. I held still, letting a bit of cum drip down my leg. I sensed the second guy approaching me from behind, like he was inspecting my ass, hesitating.
“Fuck it,” he said, and I heard his pants swish as they dropped to his ankles.
He pressed forward, even more tactlessly than the first guy, pushing a very thick chunk of meat into me.
“Damn,” I muttered, the first words I had let out since they came down.
He didn’t answer. He just started humping me quickly, on a mission to cum inside something warm, even if it was a boy in his frat.
“It’s actually good,” he said.
“I know right,” the first guy replied. After a moment, he added, “I’ll see you upstairs.”
I heard him ascened the stairs as the second guy rattled my body for another two minutes while I jerked off slowly, edging to the anal stimulation. It felt so good I almost wanted to cry.
He finished with a few powerful thrusts, the pangs of pressure running up my core only adding to the joy of it for me.
He pulled away unceremoniously. I held my dick hard, deciding not to cum.
“You’re a really good sport,” he said, leaning against the wall as he pulled up his pants.
“I know, right,” I said. “I’m getting the hang of it though.”
As he ascended the stairs, I wondered how long I was going to be waiting for my next sperm donor.
To my delight, I heard my new favorite words just as he opened the door.
“I warmed him up for you.”
—[]—
Outside the house, nobody talked about our special Cupcake situation. Ever. Inside the house, it was just understood. Phones stayed upstairs. The basement door stayed closed. If someone new wandered too close to the stairs, one of the brothers would casually redirect them somewhere else. Alumni seemed to know about it already, like the whole thing had existed long before I showed up. The only thing that ever leaked outside the walls was the nickname. Cupcake. Sometimes one of the guys would call it out across the quad or in the dining commons. People nearby would snicker, assuming it was some stupid fraternity joke. Only the brothers understood what it actually meant.
The weird part was how quickly I got used to it. The first few nights my heart raced every time I walked down those basement steps. I felt like everyone could hear it. After a while it became routine. I started recognizing the sounds of the house settling late at night, the way the basement lights hummed, the worn spot on the couch where I usually leaned. Sometimes someone would walk down behind me and clap me on the shoulder, half joking, half serious. "Cupcake, you busy?" Eventually I realized I was looking forward to hearing it.
After a few weeks someone hung an expensive-looking, ceremonial robe on a hook near the basement stairs. Nobody ever said whose idea it was. One night the frat president tossed it to me and said it made the whole thing look more "professional." The robe became part of the ritual. I would walk down the stairs, tie the belt, and take my spot near the couch while the guys joked around or watched whatever YouTube brain rot they were streaming, coming over to use me intermittently. It actually made everything feel strangely organized, which made it somehow hotter.
Different guys developed different habits. One guy literally made me lie flat down and called me a girl the whole time so he could get off. One brother always insisted the lights stay off except for the glow of the television. Most of them didn’t talk at all, but one guy talked constantly about whatever was happening in class or at practice, like we were just hanging out while he was stuffing his dick into me until he jizzed.
One guy always brought a blanket and draped it over my shoulders first, like that somehow made the whole situation easier for him. Everyone approached it their own way. Over time I learned the rhythm of the house and the personalities of the guys who lived there. Honestly, I probably got better acquainted with the guys than any other pledge.
Cal was different from everyone else. Most of the guys treated the whole thing like a joke, chuckling at the beginning, finishing quickly and getting the hell out of there, even if it was obvious how much they loved cumming inside me. But Cal never rushed anything. Half the time he would just sit next to me for a while first, talking about classes or the gym or whatever game was on TV. Sometimes he would ask if I had eaten that day or if the other frat brothers were giving me a hard time. The conversations felt normal, almost calm compared to the energy of the rest of the house. I would basically start things with him, getting him hard and telling him to fuck me. And once he got into it, he was the best fuck among the whole house. His big dick split me open and found buttons inside me that no one else came close to touching. He would take his time and even throw me around in different positions. He knew what I liked, and gave me everything. He was the only guy who would jerk me off when he fucked me, and along the same lines, he was the only guy in the house I ever gave head to.
But after the deed was done, he was sort of back to being just another frat bro. Friendly, and helpful, sure, but not the caring guy I had come to adore.
The contrast between my duties and punishments and those of the other pledges never stopped being funny to the guys upstairs. When someone else missed a trivia answer during pledge meetings, they got paddled. When I missed one, Charles would just grin and point toward the basement stairs. "Thirty minutes," he’d say. The room would erupt with laughter and someone would clap me on the back while I headed downstairs. It became part of the rhythm of pledge season.
Weeks turned into months faster than I expected. By the time initiation night arrived, the whole thing felt normal. We stood in a line with the other pledges during the ceremony while the older brothers talked about loyalty and tradition. When it was over and we were finally full brothers, the house exploded into celebration. Beer everywhere, music shaking the walls, everyone yelling over each other about surviving pledge season.
Nobody told me to go downstairs that night.
I went anyway.
The basement was quiet compared to the chaos upstairs. I hung the robe on the hook, leaned against the couch, and waited. A couple guys wandered down eventually, surprised to see me already there. Two brothers came in, muttered something to each other, and closed the door behind them. They took turns on my ass while the music raged upstairs. They got their nut, and I got my fix. After a while I cleaned up, tied the robe again, and headed back upstairs.
It was getting quiet, and about time to go home. My dorm was across campus at the Quad.
Cal stopped me in the hallway.
He didn’t say anything at first. He just took my hand and led me toward his room. Inside, the house noise faded to a muffled thump through the walls. For the first time all night everything felt quiet.
He stepped closer and kissed me. It was the first time anyone had done that. The moment caught me off guard. I stood there for a second before leaning into it. It felt warm, almost calm compared to everything that had happened during the semester. I grabbed his sides and he held my hips tightly, pulling our bodies together. We fell onto his bed as I felt his big dick start to press against me.
I pulled away after a minute. “I never kissed a guy before.”
He almost rolled his eyes as he chuckled. “Okay…”
He looked me in the eyes as he rolled on top of me.
"Pledging’s over," he said quietly. I could smell his minty breath, like he had just chewed gum.
I looked at him for a second before answering.
"I’ll still be your pledge," I said.
He smiled at that.
For the rest of the year, Cal was the only one I slept with. Most nights I ended up in his room at the house instead of walking back to my dorm. Sometimes we just talked or watched whatever game was on while the noise of the house carried through the walls. Other nights we ended up tangled together under his blankets, the rest of the world fading into the background. It felt different from everything that had happened downstairs. Cal never treated me like the Cupcake in those moments. With him it was quieter, slower, almost normal, and I realized I had started looking forward to those nights more than anything else. Maybe this is what a boyfriend is like. It’s hard to say.
But whatever it is, I like it.