Convincing My Straight Frat Brothers - Part 3: Expanding My Hole

Everyone is 18.

Leo watched as I laid back, while Jaxon milked his cock to get the final drops of cum out and rub them on my ass cheek. 

“You wanna just jerk me off then?” Leo asked as I melted back into the bed, a little bit of despair in his voice that he was too big to actually fuck me. 

“Bro just fuck me—I can take it,” I said, not even sure if it was true, “just use a lot of lotion.”

His eyes lit up upon hearing me say that. 

I knew that I would let him stretch me open as much as possible possible, even if it hurt and then hurt some more. I was determined to take it. Even through the intense pressure, looking down and seeing my hole stretched to the thickness of a pringles can was all I wanted.

Leo looked at me, his expression a mix of excitement and doubt. I nodded eagerly, reassuring him. He took a moment to gather himself before moving closer to the bed. His cock was so thick and long, I doubted it would be able to enter me, and I couldn't put my fingers all the way around it. He applied more lotion, smearing it all over his shaft and my hole, making sure we were both coated in the slick substance. I felt the previous load leaking out from inside me, grateful there was even more lube, and I took a deep breath to brace for the intrusion. 

“That’s not gonna fit,” Jaxon said as he got up on the bed. He placed his hands on my chest and held my body down, as if anchoring me to support Leo’s impending invasion.

Leo knelt between my open legs, his cock pointing straight at my juicy hole. The soreness throbbed inside me from earlier, but nothing was going to deter me from my ambitions today. He looked down at me with a glint in his eyes, then back at his own cock. He took it in hand and rubbed it against the cheeks of my ass, leaving a wet trail of precum and lotion on my skin. My mouth fell open in anticipation, as he leaned over me, his cock increasingly pressing against my opening, and whispered, "Ready?"

I nodded and took a deep breath. He pushed in, and the pressure was immense, like nothing I had ever felt before. My eyes watered and I bit my lip hard, trying to keep any sounds of pain in. Jaxon rubbed my chest and my hair, supporting me in a way. It felt like I was being split in two, but I had to show Leo that I could handle it. His cock was a beast, and I knew if I could take him, I could take any of them. He pushed in inch by inch, his slender abs growing rounder and fuller as he flexed his abdomen with the effort of holding back his desire to pound my ass like the others had. I focused on his face, his eyes tight with concentration and his mouth slightly open as he felt my tightness around his cock. Finally, with a grunt, he was fully sheathed inside me, his balls resting against my taint. He paused for a moment, looking down at the sight of his cock disappearing into my body. I knew he was enjoying it, and I wanted him to enjoy it more. 

"Do it," I whispered, begging for the release that I knew was coming. He took the cue and started to move, his thick cock stretching me out even wider than Cody and Jaxon had. Each stroke was, in a way, agonizing, but with every inch that he pulled out and pushed back in, the pain combined with a deep, new sense of pleasure that I hadn't known before. It was as if my physical body was being redefined by the shape and size of his cock.

Behind his massive third leg of a cock, Leo was a gentle twink, his strokes slow and deliberate, as if savoring every moment of our encounter. I could feel my ass stretching and adjusting to the sheer size of him, and it was an exhilarating sensation, one that made me feel both overwhelmed and alive. The smell of our mixed arousals filled the room, and the sound of his cock sliding in and out of me was the sweetest symphony. I reached down to start jerking myself off, the anticipation of his cum filling me up was too much to handle.

Jaxon moved his athletic body to drop his sweaty balls onto my face. I could smell the musk from his ass, and his balls left a distinct flavor of manliness on my tongue when I slurped them up. His cock had not gone down much since he pulled it from my ass, and it rested on my neck and chest. Leo took a deep breath, and started to pick up the pace. His cock was a battering ram, pushing into me with more force each time. My moans grew louder, and I could feel the cum boiling in my own cock. He was hitting spots in me that I didn’t know existed, and it was like an electric current was running through my body. The pain was morphing into a pleasure that I hadn’t ever felt before, a kind of masochistic bliss that was taking me to new heights. As my body moved with his thrusts, Jaxon's balls bounced up and down, and I could see Leo for brief flashes when his taint lifted off my eyes.

The room was a blur of sweat, groans, and the sound of flesh slapping against flesh. My body was on autopilot, just taking in the pleasure that Leo's massive cock was giving me. The pain was still there, but it was a part of the experience now, something to be embraced. Jaxon started stroking himself as he took over jerking me off as well, the sensation building up to something unimaginable. I recall feeling like I was almost going to cry with a mix of joy and adrenaline. Leo was getting closer, and I could feel his cock thicken and swell inside me. His breath grew ragged and his grip on my legs tightened. When Jaxon liften his body off my face, I looked up at Leo, his face a mix of concentration and pure, unbridled lust. It was like watching a wild beast claim its prey, and I was more than happy to be that prey. His strokes grew faster, and the headboard banged against the wall in rhythm with our movements. I knew the other guys in the house had to be hearing this, but I was hoping that would only increase recruitment for my new project of fucking my way through every dick in the frat that would have me. 

And then it happened. With a sort of growl that seemed to come from deep inside his body, Leo shot his load into me, giving me a a series of pulses that stretched my hole as he coated my insides. It was like nothing I had ever felt before, different than the loads I took before him. The pressure was immense, and for a second, I thought he had literally punctured my lung with his cock. But it wasn’t painful, not really. I was numb to the pain at that point, only feeling a tingle in my core. It was a strange, overwhelming sensation of fullness that seemed to reach up from my ass into my chest and light me up from the inside out. I moaned around Jaxon’s cock as Leo’s warm, sticky cum filled my ass, feeling like I was being claimed by a creature of pure lust and power. Jaxon pulled out and furiously rubbed the head of his cock, aiming it at my face, and released several squirts of my new favorite meal toward my open mouth. I licked what I could from my lips before he put his dick back inside to milk his last drops onto my tongue.

After they both finished, we all kind of just laid there for a moment, breathing heavily. Leo’s cock was still in me, and I could feel it pulsing slightly as his body and cock began to relax. Jaxon was lying beside us, letting his cock hang down over his balls, and looking at me with a mix of amazement and incredulity.

“You’re a fucking champ, man,” Leo said, his voice thick with satisfaction.

I couldn’t help but beam with pride, despite my body feeling like it had just been used by a jackhammer. “Thanks, Leo,” I replied, feeling his cock slipping out of my now-loosened hole, making me feel empty.

Leo looked down at me with a smug grin. “No problem, bro. I didn’t know you had it in you.”

“I honestly never would have guessed you would have a cock as big as a pringles can!” I said, still in awe at his cock.

“Well you can have it anytime,” he said, “when my girl is busy.”

“Same with mine,” Jaxon chimed in. They gave each other a high five.

“I honestly think I’d be happy to go room to room in this house taking loads.” I said, acknowledging my real ambition after today.

Leo lifted his twink head as he was pulling up some grey sweatpants. “Make it happen bro. A guy’s gotta have a dream.”

When Jaxon and Leo looked like they were ready to get back to doing whatever they were doing before I walked in, I took Jaxon’s discarded underwear and wiped myself off, threw them in the corner, and headed out of the room.

As I left Jaxon’s room, still feeling the echoes of the invasion of my now battered hole, I kept thinking about what Leo said. Make it happen, bro. The thought stuck in my head. I had already been amazingly lucky, barely having to convince the first three guys that I wanted to experiment with their dicks. I glanced down the hall, looking for any other open doors. The only one ajar was that of one of the frat bros, Skye, a more reserved guy in the frat who really only loosened up at parties. I think he honestly liked jerking off more than sex. He often went upstairs to his room alone, even after spending the night flirting with sluts. Even I would still take a warm hole over my hand, usually. Sky had chosen the room at the end of the hall because it was more often left alone, as no one walked by it unless they were coming to his room directly. So there was not much foot traffic down that way. He would be an interesting challenge.

I approached his door carefully, rubbing my sore ass. I didn’t want to assault him too abruptly with my nudity, so when I saw him at his desk, facing away from the door with big headphones on, I knocked gently on the open door. He didn’t react, causing me to hesitate, watching him for a moment. His hair was slightly damp, likely from a post-shower moment, and the way his loose tank top hung off his frame gave me a glimpse of his toned arms.

I knocked again more firmly, but he still didn’t react. I cleared my throat. “Hey, Skye.”

I knocked lightly, and he didn’t react. I stepped inside and cleared my throat. “Hey, Skye.”

He quickly closed a bunch of browser windows on his computer, then turned his head and looked at me with wide eyes, pulling one earcup off. “Oh. Hey. What’s up?” He tried to be nonchalant, but his nervous look gave away that he was busy shucking his corn while watching hardcore vegetable content on his computer.

I stepped around the corner, revealing my naked body to him, now covered in scratches and traces of the juices from all the events of the day, my heart pounding. “Just saying hey. Quiet night?”

He looked curiously down at my red, floppy cock, then back up at my face with a curious expression. “You good?”

I smirked, sitting on the edge of his bed. “Yeah. I’m good.”

Skye raised an eyebrow. “Why are you naked?”

I shrugged, reaching out to brush my fingers along his arm. “I thought maybe you'd want an upgrade from your hand tonight.”

His eyes searched mine, hesitant but intrigued. “Bro, what the actual—”

I interrupted him by putting a hand on his shoulder and leaning in slightly, whispering, “I can take care of everything. Just let yourself relax and reopen those browser windows.”

He exhaled sharply, as if considering it. Then, after a long pause, he shrugged. “Alright. But don’t tell anyone.”

I grinned. He didn’t realize yet that I was converting into a fraternity slut. I watched as he hesitantly reached for the keyboard, bringing back the previous tabs where a milf’s pussy was being enthusiastically battered by two college-aged guys at once. Their dicks rubbed together, which was hot. Skye’s breathing was uneven, his eyes flickering between the screen and me as I slid off the bed onto my knees in front of him. I was far too sore in my ass to go for more anal. I mean, if he asked for it I would not say no, but I literally feared for the integrity of my hole if I didn’t put a cap on it at some point tonight.

I reached for his sweatpants, tugging them down, revealing the eager appendage beneath. Without hesitation, I leaned forward and took him into my mouth, savoring the salty taste of his fresh precum. He let out a strangled breath, his focus initially on the screen but his attention quickly shifting as my tongue worked its way around his cock and my hands explored his larger than average balls. He sat apparently frozen to his chair, with a nervous look on his face, refusing to look down at me. He took off his shirt and I saw that he had actually begun hitting the gym, as there was the slightest definition in his teen pecs.

He let me work at my own pace at first, his hands gripping the armrests of his chair, his chest rising and falling rapidly. But as I hollowed my cheeks and took him in deeper, he started to react instinctively. One hand tentatively landed on the back of my head, fingers curling into my hair.

“Damn,” he muttered, eyes still half-glued to the screen, but his focus was wavering. I could feel the tension in his body, the way his hips shifted slightly toward me. His need to maintain control was breaking down. I moaned around his length, sending vibrations through his crotch, making his grip on my hair tighten. He leaned forward slightly, his breath hot as he exhaled, voice dropping lower. “Shit… that feels good.” I loved getting the same compliment twice.

I took him deeper, my throat stretching around his girth, and that was when he fully let go. His other hand found its way to my head, gripping me firmly as he started guiding my movements, thrusting into my mouth at his own pace. The sound of the computer played in the background, but I could tell his focus had completely shifted to me as his shaft disappeared inside me.

His breathing grew ragged as he started to lose himself in the sensation, his movements growing more urgent, more needy. I could hear him swallow nervously multiple times, then breath heavily and gulp again. His thighs tensed beneath my hands as I braced myself for his increasingly deliberate thrusts, my lips stretched wide around his pulsing manhood. He was acting like an ape, purely primitive as he bounced his sweaty, college boy ass around in the chair, getting his pleasure from my mouth and throat.

“You’re taking it so good,” he groaned, his voice strained as he held my head steady, thrusting deeper with each movement. He twitched in my mouth, signaling he was close to releasing what I came here for.

I looked up at him through the oral ravaging, urging him on, my tongue swirling around him eagerly. His grip tightened one last time, and with a squeaky groan, he pushed all the way in, pulsing rapidly as he spilled his warm cum straight into my stomach.

I swallowed every last drop, savoring the taste as he shuddered above me, his fingers loosening in my hair. He leaned back in his chair, breathing heavily, looking down at me with a mix of disbelief and satisfaction.

“Holy shit,” he muttered.

I wiped the corner of my mouth, smirking up at him. “Told you it’d be better than your hand.”

He let out a breathless chuckle, rubbing a hand over his face. “Yeah… yeah, I guess you were right.”

I stood up, stretching slightly. “So, you’re probably gonna want to keep me around, huh?”

Skye shook his head, still looking dazed. “I mean… maybe.”

“You know where to find me.”

He exhaled, slumping back in his chair, still catching his breath. “Yeah.”

And with that, I left, amazed at my success in scratching an itch today that I had been struggling with for so long.

It was about midnight, and I was spent as hell. I went up to my floor, and hopped in the shower. The hot water was like a massage on my battered body, and all the spots of cum and spit and sweat on my body felt like merit badges as I washed them off in the cleansing stream. When I got out, I decided to air dry, and after a minute I grabbed my phone and headed naked out of the bathroom. When I got in the hall, I saw I had a message from Cody. 

“Party in the basement, no clothes for you.”

Fuck.