Sleepover with Will and Conner — Chapter 2

Everyone is 18.

Chapter 2: Turning Around

When I turned back to my two buddies on the couch, I saw two devious smiles. They had been whispering to each other while I was turned around.

"What?" I said, wondering if they had gotten cold feet again, if this was too gay, or something like that.

"You, uh..." Conner started, "you have a nice ass. It looks like a girl's."

I felt my face turn red and my cock start to get hard again. Did I hear him right?

They started stroking their dicks and looking at me sort of hungrily. I had known these guys forever. I never expected them to lean this far into gay shit, especially since all we did was talk about girls and pussy. When the night started, I was just hoping we could jerk off together and bond as bros. But I guess after leaning over and sucking their dicks, things had changed.

My submissive nature and the desperation for intimacy drove me to respond to them. I walked over to the coffee table and turned away from them, leaning over it. “Does it really look good?”

“Yeah,” said Conner as he smacked my ass, hard enough to leave a handprint. I heard them laugh as I flinched. Will joined in, slapping my other cheek, earning another chuckle from them, but I didn’t flinch this time. I held still where I was, submitting to their gaze, until I felt their hands on me again. This time, they were gentle, just rubbing and squeezing my cheeks.

“It actually does look like a girl’s ass, if it weren’t for his balls hanging down,” said Conner. I laughed at that one.

“You take the bad with the good,” I said, reaching back to spread my cheeks apart. I could feel their eyes staring into my pink, hairless hole. One of them pressed play on the porn on the TV, and I looked up and saw a girl’s pink asshole. I pictured that I was her, a bizarre feeling, but hard to avoid since I was literally letting two friends play with me and pretend I was a girl.

I felt my hole wink involuntarily as I stretched my cheeks.

“Woah, that’s cool,” said Will. I couldn’t believe they weren’t freaked out by any of this. These were two of the straightest guys I knew. But, young male hormones will make you do whatever you need to do to have a better orgasm.

When the guys on the screen started fucking the porn star, I sensed what was coming next.

“Should we… practice… with him?” Will whispered tentatively to his shorter lookalike sitting next to him. 

“Practice sex?” replied Conner, his voice suddenly less confident. 

“I mean, as long as no one would know, I’d do it,” Will said flatly, apparently already having made up his mind.

They were talking about me like I wasn’t even there, and that was somehow comforting. It was like getting a window into their private lives, how their thought process worked when no other friends were around, because I had become just an object to them. 

“I will if you do,” said Conner, and as I watched the girl on the screen getting pummeled by large, thick, pink cocks, I braced for whatever was coming next. 

Will grabbed both my hips, and I felt his cock line up to my cheeks. No ceremony, just going straight for what he needed. I felt his warm spit drip right onto my hole, and then the large, round head of his meat stick was pressing against me. The sensation was bizarre at first. I felt a strange pressure and tingle. When I relaxed into it, and leaned back, he knew I was ready. He pressed forward firmly, breaking the tension my hole was producing, and slipping the head of his dick inside me. 

My initial reaction was oh fuck, I’ve gone too far, this is gonna hurt, but he must have sensed my reluctance, as he placed a cool hand on my back, rubbing gently, silently telling me that it was all ok. I finally looked back, and seeing Will’s face, his mouth dropped open in pleasure, his smooth skin shimmering from the glow of the TV, I knew I wanted this. Making him feel good was giving me everything I needed. 

Conner sat on the couch, watching the show, gently tugging his thick cock. They had both already cum twice tonight, first in a three way jerkoff race, and the second in my mouth when they wanted to know what blowjobs felt like. I guess their limits for what constitutes “gay” had fallen off completely, because now they were set on stretching my hole and filling me up.

As Will pushed in further, I became sort of numb. A single tear from the tension dripped down my face. The slight pangs of my organs readjusting continued, but the burning of the stretching of my hole was gone shortly. Before I knew it, it had actually started to feel good, like I was getting a massage on the inside, and my inhibitions disappeared. If they were willing to look right at my asshole and decide they wanted to fuck it, then what could I possibly have to be ashamed of?

As the guys on the screen started cumming on her face, I knew Will was going to get extra horny. I gave him permission by reaching back and grabbing his hip, guiding him further into me. I felt his body press against mine, two naked males in the prime of our lives enjoying each other’s physical sensations. I wanted to feel more. I reached between my legs and grabbed his balls. From the feel, I noticed how much bigger they were than mine. I tugged gently, until he pulled back and started thrusting in my ass. Numbness turned to discomfort at the repeated stuffing, but quickly changed to tingles and pleasure. Conner got up and stood next to me, holding his large cock at the base, wiggling it absentmindedly as he observed Will pressing into me repeatedly. 

“You can go harder,” I said out of nowhere. I didn't even know if I meant it, but Will didn’t hesitate, holding my hips tighter and starting to thrust more quickly. I took it surprisingly well. I even liked it more when he was going fast.

“Yeah,” I said, “that actually feels good.”

“Really?” said Conner and Will at the same time.

“Yeah… guys, it’s like… really good,” I said between breaths as I started to feel my body getting rocked by Will's thrusting.

“That’s crazy, bro,” Conner said, as Will started pushing as deep as he could inside me. He added more spit to his cock, and pulled my body back as far as it would go onto his crotch. I was taking his full dick, and I didn’t want to be anywhere else in the world. I started making involuntary noises from my throat. It started with a sort of grunt, then a couple breathy moans. 

Conner shushed me, and quickly placed a hand over my mouth. I guess controlling my body was something they were getting used to. I looked at him with my eyes half closed as Will continued to pound me, apparently approaching an orgasm. I was so full of lust I couldn’t even remember my name. Conner could tell I was fully out of it from getting fucked, and he stuck a finger in my mouth. I sucked on it like it was his cock, and I could see him getting hornier by the second. My own cock was throbbing between my legs and leaking a sticky string onto the coffee table. Conner surprised me by reaching down and grabbing it. The sensation was overwhelming, and I let out another moan, before he covered my mouth with his other hand. He proceeded to start jerking me off, the most intense sensation I had ever felt in my life, as Will’s body started to slap loudly against my ass. 

We were making so much noise, I was surprised no one had come in yet, but in that moment I didn’t care about being caught. All I cared about was cumming and taking a load. It didn’t take long for Conner to make me cum with his hand, using my pre-cum as lube and focusing on my head. I was squirting a load onto the coffee table in seconds, and Will wasn’t far behind. 

“I can feel it pulsing,” was all he said before he buried himself balls deep inside me and throbbed. I felt the load pulse out of him rhythmically, and the pride from him getting off inside me was the best feeling in my life. 

He pulled out of me kind of quickly, and I immediately hated the sensation of feeling empty. I wanted to chase the rush I was getting from being stuffed. Even after I came, I wanted more in my ass. I assumed Will would have some post-nut regret again, since this was so obscenely gay. He sat back on the couch, and picked up his phone casually. I could tell he needed some me time to digest what he had just done.

Luckily, Conner was ready to go, and stepped behind me, quickly taking Will’s place. I arched my back to make sure he could see my hole, and just as I felt Will’s load start to leak out of me, Conner pushed it back inside, his larger cock stretching me more than Will’s had. Even if it took a minute to get used to it, this was exactly what I wanted. 

Conner didn’t take his time rearing up. He went straight in, as deep as he could, and I heard him exhale in pleasure. It was like he had finally felt something that he’d been dying to try. After just a few seconds, he pulled out of me, and I instantly felt empty again.

“Over here,” he said, and I looked back to see him gesturing at the couch. Will was sitting there on his phone, completely naked, his thick, wet cock resting on his thigh. I sat next to Will, and lifted my legs, looking up at Conner, waiting for him. To my delight, he squatted down, held my legs by the bottom of my thighs, and lined up his cock again. When he couldn’t get it in, I reached down for him, and lined him up with my hole. He pushed. And when I felt it pop into me, everything was right in the world again.

He started going even faster than before, really stretching me out. My breath started to hitch as I tried to adjust to Conner’s furious pounding. He was like a boy on steroids, his focused face set on cumming, as his unfairly thick rod disappeared repeatedly below my balls. I watched his body contract with every thrust. When did I start enjoying male bodies? I thought to myself. I really am becoming a girl for them. 

Before I could even get used to Conner’s battering of my hole, I saw Will’s cock get hard again out of the corner of my eye. He gave it a couple strokes, as is the male instinct, then reached for my head, trying to tug me over to him to blow him. 

Conner reached out and stopped him. “I’m using him, wait your turn.”

“He has two holes, dude,” Will replied, annoyed. 

I looked between them, wondering who was going to win this quibble, until Will got up on his knees, and brought his cock to my face. He straddled my body, his ass resting on my chest, as he lined up his cock with my mouth. Conner continued going to town on my hole.

“Bro, I can see your hole!” Conner whispered to Will insistently.

Will ignored him, pressing into my mouth. I tasted my musk and sweat on him, his jizz, and the essence of my ass. It drove me wild to see how crazy we were getting. He started out rough, holding my head with both hands and using me to rapidly massage his cock. I was in a position that should’ve been humiliating, but the thought was only a distant presence, overshadowed by the pleasure I was getting from the two dicks ravaging my body at the moment. 

“I’m gonna cum,” Conner said, his body plop-plop-plopping against me rapidly. My head bounced on Will’s crotch repeatedly until he pressed his cock into my throat and held it there, his balls squished against my chin. I gagged as I felt both cocks pulsing inside me at the same time. Conner reached down to rub my dick again, and I came, squirting up Will’s back and dripping down his ass cheeks. 

When Will was done, he pulled out of me and let me breathe. I sucked in a quick breath, and coughed and sputtered, recovering from the amazing oral sesh. Conner stayed inside me, his finger tracing the cum running down my abs, like he was curious about it. “It’s different from mine,” he said, his eyes focused.

“Bro, you nutted on my back,” Will said, annoyed, not realizing the irony of him having just cum literally down my throat. He got up to go to the bathroom.

When Will was gone, Conner looked down at me, my red face covered in tears and sweat. I looked back at him for a quiet moment, before he leaned down and kissed me. Our tongues found each other sloppily, not really knowing how to make out. Somehow, this was the most intimate thing we had done so far, and it felt good. It felt right. I could tell it had to be a secret from Will, for whatever reason, so when we heard him coming back from the bathroom, I accepted it when Conner pulled away from me, and pulled his heavy dick out of my ass. I started leaking immediately, trying futilely to tighten my hole. Conner sat back on the couch, quickly back in “manly mode,” and let his cock rest on his abs. Will came back wearing pajama pants and no shirt, and sat on the couch, grabbing the remote and scrolling through streaming options, silently. 

When I got up to go clean myself off, Conner stopped me. 

“Hey,” he said, “clean me up.” 

I smirked, knowing that he was putting on somewhat of a show for Will. I knelt down in front of him, and took his still hard cock in my hand, and leaned down to clean off all the cum and sweat and juices. In that moment, it hit me that I loved sucking dick, and that I would probably be doing it a lot more from then on. When he seemed to be clean, he gave me a light slap on the face, and I headed down the hallway toward the bathroom. 

On the way there, I noticed another room had a light on underneath. Their parents were two floors up, far away from us. I thought for a second and realized it must be Charlie’s room. My sick mind took over, and I tip-toed to his door, putting my ear up to it and listening. I heard moans. Porn moans. I thought for a long moment, seconds turned to a minute. I stood there, naked, probably risking a lot already just by walking around like that. Should I press my luck further, and see if I can get one more dick out of this household?