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“Maybe it was always meant to be.“

Chapter 1: Cupcake

This past school year, I became a free use hole for my frat brothers.

I’m sort of a skinny guy, and I’ve always looked young for my age. I can even pass as a girl, proven at Halloween last year, where I wore a wig and was literally mistaken for a girl the entire night.

While I didn't come to college expecting my frat pledging to devolve into my ass becoming a fleshlight for the brothers, it’s not the first time I let a dude use my hole. 

Last year, near the end of my senior year of high school, I let all my friends use my ass one night, to sort of practice sex. We were all still virgins, and we had gotten silly one night when there were all staying over at my place. We had been drawing boobs on each other’s butts after pushing the limits of each other’s comfort for years at this point. After a brief comparison test, to my surprise, they all agreed that my decorated boy butt was the most “boobs-like”, since I had some round jiggle to it, and not a single hair. It was hilarious at first, but when my friend Drew kept rubbing it, we sort of just stopped laughing, and I laid on my front to let him play with it while I grabbed a game controller. 

Before I even realized what was happening, he had started rubbing his dick on me, coaxing some blood flow into his cock while he ran it up and down my ass. I pretended not to notice at first, but when Jake pointed it out and started making fun of him for it, he pulled out his phone and started playing some porn, as if that would somehow make it “less gay”. Apparently it was a successful maneuver, because soon, the other two of them were standing on either side of me as Drew started thrusting harder, the giggles among them softening into fixed gazes, shared between the porn and my ass. I felt him grow even stiffer as his leaking cock pressed more firmly against me.

“Wait it’s actually working,” Drew said, noting that he was getting fully hard while “pretending” to hump my ass, until he was actually thrusting hard, trying to cum. 

I braced as he kept going, and before I even knew what I was going to say, I blurted out, “You can just stick it in if you want.” 

I felt my stomach flip after I said it, my face felt hot and my chest hurt. If I didn’t have a heart attack and die at that exact moment, I was about to get fucked. 

No one said anything. We paused for a moment, as if getting used to the idea that our friendship and personal boundaries were about to reach an unexpected new level. Jake threw him the hand lotion from my bedside table, which was for my “dry hands” problem that I had every night after going to bed. 

I braced again when I felt his wet shaft line up with my hole, and held still while he slowly pressed inside me. My whole ass tightened, and I felt him respond to my body, pausing until I relaxed, then pushing in further. It burned a lot at first, but I had honestly been so bored before this, that I considered it “something to do” at least, in a weird way. At least that was how I explained it to myself. 

He slowly pressed until he was balls deep inside me, and then suddenly started humping wildly. The quick pace shocked me, and my body tensed as I started moaning a bit.

“Dang dude,” I said, “That’s rough.”

“I’m cumming dude,” he said breathlessly.

“Ok,” I said, scrunching my face and bracing as he pounded my poor ass. 

He was done within seconds, pulling out slowly. I felt weirdly accomplished. There was something nice about it, like we had shared a good moment.

“Woah,” he said, as I kept my eyes closed, facing forward.

“It looks like a pussy,” Jake said.

Before I even realized that this was going to be a group thing, my third friend eagerly jumped on top of me and pressed his dick inside. The sharpness was somehow easier to take, even with no warning.

He held my hips and humped me fast like a rabbit while I grabbed a pillow and held onto it tightly. He was slightly smaller than Drew, and came inside me in less than a minute. He paused when he came, and I could feel him pulsing.

The last up was Jake, and although I was trying not to look, I glanced back, and I couldn’t miss that his thing was huge. I had never seen it hard before. 

“That’s too big, dude,” I said, “You shouldn’t fuck me.” 

“C’mon, everyone else got to,” he pleaded.

I only paused for a second before relenting. “Alright, just go slow.”

I laid down straight again, bit my lip and braced as he slowly pushed his monster can dick inside me. It really was too big, but in the sense of fairness I held the pillow and did my best to relax. The sensation of a deep, thick sausage stretching out my ass and moving my organs around was so bizarre, but the excitement it added to an otherwise relatively mundane day was enough for me to let it go on. He held me tightly, almost affectionately as he laid his body against mine. The bare skin of his chest warmed my back as he started humping. When he was all the way inside me, he started breathing hard in my ear as he started giving me tiny thrusts. I looked to my side to see Drew and my other friend were playing on their phones, showing each other memes, already completely done with our experiment. Jake stuffed me deeply and slowly for several minutes, before he finally squeaked out a quiet, “I’m gonna cum” into my ear.

I counted the beats as I felt him pulse his load deep into my body.

“Bro,” I gasped when he pushed inside hard, adding yet another centimeter of depth when he was at his maximum, engorged fullness. 

He face fell onto my shoulder, our cheeks touching as he hit the peak of his orgasm. As he moved, his lips touched my cheek, then my ear, and I felt his breath. I got tingles down my side as my boner was pushed hard into the rug below me. 

He slowly got up off me, slipping his heavy sausage out of my ass and sitting up on his heels.

To varying levels of success, I had gotten fucked by all three of them, taking each of their loads inside me, and I turned onto my back to finish off my own salami, spurting a quick load onto my abs while they turned off the porn and started the Xbox again. I was already wiping up my load with a dirty sock before the first loading screen was done. 

Overall, It hadn’t hurt as bad as I thought it would. It was actually kind of a good feeling to do something nice for my friends. 

We didn’t talk about it after that, but it happened one more time later in the Summer, with Jake, after he begged me one night at my house. That time, he jerked me off too while he was still inside me. Fair trade, I thought. 

And that was it.

—[]—

I went off to college a few months later. I got into a “good” school, compared to most of my friends, and I flew across the country to a place where I didn’t know anyone. Luckily, most people were in the same boat as me, and making friends was easy for the first few nights. Then came rush week, and the social scene amped up even further. It was like these frat bros were competing over all of us freshmen. 

Something attracted me about this one frat. Their rush event wasn’t anything special, “Pins and Pilsners” where we went bowling and had fun, but this one tall guy caught my attention. He kept looking at me from across the room. He was tall, muscular, a year or two older than me, and he watched me like he knew something about me, or maybe like he was looking out for me. I couldn’t figure it out. I never got a chance to actually talk to him, but he stuck in my brain, and made me want to come back to their next event.

By the end of the week, I got the letter saying I was “in”.

“Welcome to the frat, Cupcake. Pledging starts next Friday night at 10pm at the house.”

I sighed at the nickname, knowing that it would stick for years, based on my perception of frats.

When I got to the frat house for the first pledge event, I found out that the nickname was due to “All that cake”, according to one of the brothers. He gestured at my round, ample ass. 

“And it’s all in that little package,” he said, gesturing to my otherwise lean frame. I’m not even short, at almost six-foot, but I definitely have a bubble butt that sticks out on my lean, swimmer’s frame.

During the actual event, the tone was a significant departure from the outrageous nature of rush week. Now we were pledges, subservient boys tasked with earning our way into the frat. 

We lined up, and the frat president, Charles, quizzed us immediately on the history of our school, knowledge that we mostly didn’t know, and one by one, my fellow pledges were doled out punishments along the lines of “ten pushups” or “one minute frog pose” for each one we got wrong.

I chuckled when I heard some of the other nicknames. There was “lizard boy”, “donut”, and “jock itch” among others. I did notice that none were as feminizing as mine though. Still, I didn’t mind the name “Cupcake”. If anything, I kind of liked it. I do have a nice “cake”, and although I couldn’t admit it at the time, even to myself, I had this bizarre feeling of comfort with the idea of being submissive to these dominating, older guys. 

When I wasn’t able to answer “Who is the statue in front of College Hall?”, my punishment was different. I was told to turn around. I narrowed my eyes. It seemed innocuous enough. I could’ve just left anytime I wanted. I didn’t even feel pressured to stay, but I was actually intrigued. I turned and faced away from him, as the others watched.

“Hands on the wall,” he said, stern but not forceful. I raised my hands and touched the cool brick.

“Brace yourself,” he said, as he lightly smacked my ass with a wooden paddle that he had pulled out of nowhere.

I didn’t even flinch. I just half smiled, waiting for more. When nothing else came, I turned my head halfway back.

“Good boy,” he said, moving on to the next pledge in line. 

I looked around, confused. The rest of the pledges chuckled or shrugged, and the moment was quickly forgotten. I felt like I had gotten off easy, but when the next guy had to do a two-minute wall sit as his punishment, it was clear to me that I was going to be treated differently here.

“Cupcake gets treated like a princess,” the guy next to me said.

“Honestly…” I replied, watching as the next guy did sit-ups.

—[]—

When we were done with the quizzing and punishments, we went back upstairs and discovered a huge, catered feast waiting for us. 

“Reward for enduring punishments,” Charles said as we started digging in. 

I was chatting with my new pledgemates and having fun getting to know each other, when I noticed that same tall guy from the bowling night watching me from across the room again. I gave him a nod to acknowledge him, and he just turned back to the guy next to him, continuing some conversation.

“Who is that guy?” I asked my new pledgemate buddy, as I gestured to him, “That tall guy.”

“I think his name is Cal,” he said, stuffing some food into his mouth, “Seems like a nice guy. He helped me bowl at Pins and Pilsners.”

—[]—

When we were on our way out, Cal walked up beside me.

“Hey Cupcake,” he said casually with a light smile, walking next to me as I descended the stairs to the walkway.

“Hey,” I said back, smiling nervously at the reference to my frat nickname, suddenly bashful about it now that we were outside.

“I’m heading back to campus,” he said, “I’ll join you if you’re going back to the Quad.”

“I am,” I said.

We started chatting as we walked together. Cal was a senior, a muscular gym rat, tall, majoring in finance, but he wasn’t boring. He seemed to have a darker side, some mystery to him. I never said anything about how I had seen him watching me sometimes, but I could tell there was something else he wanted to tell me. He was just sort of feeling me out first. We talked about college, classes, what to expect over the next few months, until he finally brought it up.

“So, you think you’re ready for pledge season?” he said, studying me carefully, stopping as we approached the entrance to the quad. 

“I think so,” I said. “I don’t really know what to expect, but it’s fun so far.”

“Just to warn you, it might get really fun for you specifically. If you’re up for it.”

“What do you mean?” I said, narrowing my eyes.

“Well, let’s just say, I’ve seen guys like you before, and I know how it goes. We haven’t had a Cupcake since my freshman year, but that was a… wild semester.”

“I have no idea what you’re talking about,” I said, shaking my head a little.

He reached out and put a hand on my hip, making me freeze, my eyes wide. “I think you do.”

“What do you…” I started, before he cut me off.

“You’ve been fucked before, right?” he said.

I gulped. “How did you know that?”

“You have a certain energy,” he said. “Easy to spot if you’ve seen it before.”

“But I’m not gay, I just let my friends…”

“Right,” he said, smirking. “I’ve heard that before too.”

I had to admit, as much as my heart was racing, and my skin burning with nerves, I didn’t hate what he was suggesting. 

“So I’m the Cupcake this year?” I said, looking up at him.

He pulled me closer to him, so his hips were touching me, and I felt his hard dick in his pants, large, like he had stuffed a cucumber into his underwear. He brought his face close to mine, and I didn’t pull away. 

“It’s really up to you.”

“Before I decide, do you wanna… come in and talk about what it entails?” I said, stuttering over my words a bit as I nodded toward my dorm building behind us.

He smirked, keeping his hand on my hip as we started walking through the front doors of the Quad. 

I really had no idea what was going to happen, but I knew one thing.

I was going to be the frat Cupcake, whatever it took.