Anal Between Friends Doesn't Count As Sex 03

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Chapter 3: My Loophole

It had been two weeks since the first time. It still didn’t count as sex or gay or anything like that in our minds, although we had gotten comfortable using the term "bi" when his brother, Rhys pestered us about it. Two weeks of sneaking off and fucking as often as we would normally sneak away to jerk off alone. I had basically stopped cumming alone, saving it all for when I was getting my ass stuffed by my friend. We did it between classes, after practice, on random afternoons at his place after school. We always found a way. It was easy and comfortable, and not complicated. His girlfriend didn't know, and we were under the delusion that she wouldn't care since "nothing except vaginal sex counts as sex." We didn’t even talk about it. We just knew when the moment was right.

One day after school, we ended up in his room again. The place where it all started. The air had the familiar scent of his boy smell and clean laundry, and his sheets were still tangled from the morning. I had gotten the habit of making his bed for him whenever I came over, since I just liked it that way, and he never made his bed. Just as I bent over to straighten the twisted linens on his bed, he locked the door, turned up the music, and turned to me grinning.

“Quickie?” he said.

“Obviously,” I replied.

He lay back, still in his jeans, and I slid down between his legs. It wasn’t exactly planned, but we had fallen into the habit of touching each other whenever we were alone, and it always ended with at least him cumming. I knew what he liked, and it was simple. He wanted warmth and wetness on his cock, and my place was between his legs. And, if we had time, he always took advantage of my hole. I leanred how to start slow until he was breathing heavy. It made him harder, and made him moan more, if I just held his dick in my mouth and teased him with my tongue, waiting until he was aching for it before I gave in and swallowed him whole. My mouth worked him up, and before I could even think about it, he was tugging me up by the waistband of my shorts.

“Turn around,” he whispered.

I didn’t hesitate. Whenever he gave me a command, I would drop any plans I had in my head and obey. I lowered my shorts just enough for a quickie, in case we had to dress quickly, and bent over the edge of his bed. I only had to wait a second before felt him press up behind me, his dick already lubed from his secret stash of baby oil. It was quick and urgent, our hormonal bodies taking over. I bit my lip as my body adjusted to the rapid stretching, but at this point it didn't take long for me to loosen up, even with his size. It was easy to relax when I knew that in just a minute, there would be a split second where pain turned into warmth. When it did, my body relaxed into it. He held my waist tighter, moving fast, like he was racing against time.

The buzz of his phone cut through the music. He froze for a second and reached over the nightstand, checking the screen. A text from Rhys lit it up.

Rhys: Mom and Dad are on their way home.

Michael laughed under his breath. “He knows.”

“Ally of the year,” I said, barely able to speak between breaths.

My laughter was cut short as he slammed into me, making a clapping sound against my body. He leaned forward and held my head into the mattress as he rapidly humped me like the desperate boy he was. He needed an orgasm and it was about to be cut short, unless he got the job done quickly. I was scared for half a second before I relaxed into it. He wrapped both arms around my chest and abdomen and held me tightly, moving only his hips as he fucked me like a rabbit. He was really too big down there to use me with that much vigor, but I understood the urgent need and I only responded my squeezing my ass muscles as much as I could, helping him along and waiting for my reward. 

He finished quickly, both of us out of breath. We didn’t even bother pretending it was anything more than a release. Just hormones. He flopped onto the bed, shirtless and smiling, while I wiped my cummy butt with a towel off his floor, pulled my shorts up and tried to catch my breath.

“Rhys is too observant,” I said.

“He’s saving our asses,” Michael said, grinning. “Literally.”

We cracked up. He sat up, brushing a hand through his hair. “So, uh… Emma’s been acting weird.”

I turned toward him. I felt a little knot in my stomach. “Your girlfriend?”

“Yeah. She noticed I’ve been hanging out with you a lot more. She asked why I can’t just have that kind of fun with her.”

I raised an eyebrow. “And what did you say?”

“I told her I just have a lot of fun with you. Which was true. She looked kind of hurt, so I… y’know, tried to make it up to her.”

“Meaning?”

He smiled sheepishly. “I, uh, went down on her for the first time. She said I was really good at it.”

I blinked, then chuckled. “So you couldn’t tell her that you’ve been learning on my body.”

He laughed, covering his face with his hands. “Exactly.”

“That’s crazy,” I said, feeling a twitch of something between jealousy and fascination. “Did she cum?”

“She said she thinks she did.”

“How does she not know?”

“Girls are different... I guess?”

We both cracked up again, our laughter filling the small room. Then, out of nowhere, a voice came from the doorway.

“I think that means she didn’t cum then.”

We turned. Rhys was leaning against the doorframe, holding a bag of chips.

“Dude,” I said, covering my face. “You can’t sneak up on me like that.”

He shrugged. “Your door doesn't actually lock, you know. It opens easily with your fingernail.”

Michael threw a pillow at him. “Ever heard of knocking?”

Rhys caught the pillow midair, smirking. “So, do you guys take turns being the girl, or is it always my brother?”

I groaned into my hands. “Oh my god.”

Michael threw another pillow. “Get out!”

“I think I’m bi too,” Rhys said casually, as if that wasn't awkward as hell.

We both froze.

“Really?” Michael said, blinking.

“Yeah,” Rhys said, still munching his chips. “I jerk off with my friends sometimes. It’s better than alone.”

I nodded slowly. “That’s… fine.”

Michael sighed, half amused. “Guess it runs in the family.”

Rhys grinned. “How big are your guys’ dicks?”

“That’s enough!” Michael yelled, hurling the last pillow. Rhys dodged it effortlessly, laughing as he walked out and closed the door.

The room went quiet again, then we both started laughing so hard we nearly fell over.

I wiped tears from my eyes. “Do you think his dick is as big as yours?”

“Shut up!” Michael said instantly, face red.

We couldn’t stop laughing.

—[]—

Monday hit hard. I hadn’t heard from Michael all Sunday, not a text, not a meme, nothing. That wasn’t normal for us. I found him at his locker before first period and tried to play it casual. The first thing I noticed was that he was doing that nervous thing he does, where he licks and nibbles on his lips, making them even bigger and pinker than normal.

“Hey,” I said.

He kept his eyes on the books in his hands. “Hey.”

“You ghosted me yesterday.”

He swallowed. “I told Emma everything.”

My stomach burned. “Everything everything?”

“Yeah.” He finally looked at me. “She’s upset. And we can’t do it anymore. Apparently it does count a little bit.”

I stared at him, waiting for him to say he was joking. Just a moment of denial, but it was real. Heat rose up my neck and my stomach burned. “So we’re not even hanging out now?”

He shook his head once. “I’m sorry.”

I turned to my locker so he wouldn’t see my eyes water. I shoved my stuff inside and walked the other way before I said anything I couldn’t take back. I made it through classes without hearing a single word the teachers said. At lunch I sat with different friends in the quad and picked at my food. When Michael and Emma came out together, I stood up and left without looking back.

After school I told my brother, Billy. He’s a couple years older, and I figured he might actually have advice. I found him in the living room playing some racing game in his underwear and a t-shirt, the sound of the engine echoing through the room. I sat on the arm of the couch, saying "you need a job."

"I work remote," he replied without looking up.

"I... don't think that counts."

He chuckled, and I just waited until he paused the game.

He glanced over. “You look like hell.”

“Thanks,” I said flatly. “So Michael’s done with me.”

He raised an eyebrow. “You mean your buddy you've been basically living with recently?”

“Yeah. He told his girlfriend everything about us doing some bro bonding. Now it ‘counts,’ apparently.”

He whistled quietly. “Rough.” He handed me a controller. “Wanna race? Might get your mind off it.”

“I can’t even think right now.”

“Then talk,” he said, leaning back. “What happened?”

I told him everything in quick, clipped sentences. How Michael stopped talking, how Emma found out, how I felt like an idiot for thinking it was anything more than hormones. He didn’t interrupt me, just nodded along like an older brother does when he’s trying not to give away that he’s actually listening.

When I finished, he said, “Look, dude, you’re not the first person to get crushed by a guy. I mean, I didn't know you were into guys or whatever but I'm sure it's the same as when a girl dumps you. You’ll survive. Just remember that most people in high school don’t know what the hell they want anyway.”

I stared at the floor. “Yeah, but it felt so good having a casual thing. I just miss him being around. Even after one day it feels like shit that it's completely ruined like that.”

“It just means it’s over. For now.” He stood up and stretched, his shirt revealing the hard abs I was always jealous of, reminding me of the effects of hard work. In a weird way, it made me feel like everything was going to be ok. I just had to figure things out, put in some work. “You’ll be fine. You always are.”

Then he gave me a quick pat on the back that slid down into a joking pat on the ass as he walked toward the hallway. “Go do something productive. Or not.”

He left the door cracked open, and from where I was sitting I could see his room. Messy, clothes everywhere. Under the bed, half hidden by a shoe, was his fleshlight. He knew I knew about it. He didn’t say a word any of the times I had stolen it in the past. This time, it felt like he had left it exposed for me on purpose.

I stared at it for a few seconds, then sighed. “Subtle, bro,” I muttered to myself.

—[]—

The afternoon dragged on. And by that night I was alone in my room trying to get my head off Michael. I was going to town with the toy on my dick and using way too much lube, trying to drown out the ache. I shoved a lubed up toothbrush case up my ass, but it was nothing like Michael's living organ that felt so good inside me. I kept thinking about him, and it wasn't working. I was about to give up. That’s when my phone buzzed.

Michael: I’m outside.

I sat up instantly. Outside? I peeked through the blinds and saw him standing in a hoodie under the streetlight. He looked up at me and waved. My jaw dropped. I texted him, “Are you insane? It’s 1am!”

He texted back, “Just lemme in.”

Me: Everyone will hear you come in, wtf

Michael: I'll sneak in your window.

Before I could even respond, he was climbing up the patio garden wall thing that led up to my room. 

I just shook my head and helped him climb in quietly. He looked wired, like he’d run here. He took a quick look at the fleshlight next to my bed, but he was too manic to even address it. He had something else to tell me. He sat on the edge of my bed, scrolling through his messages. “Look.”

He handed me the phone. It was a text thread with Emma.

Emma: I thought about it. You should do what makes you happy.

Michael: Really? Even if it’s with him?

Emma: Yeah. You’re honest with me. And what we have is real. Whatever happens with him doesn’t change that.

Emma: Also, thanks for earlier. I finally know what an orgasm actually feels like now.

Michael: Anytime babe. I can't wait to do that to you again. So you’re good?

Emma: I’m more than good. Go see him any time you want.

I looked up, eyes wide. “That's fuckin crazy, dude. She’s actually cool with it?”

He nodded, smiling. “Apparently I gave her her first real orgasm. Fingers and tongue. She was so hyped she literally said this doesn't count anymore.”

I laughed in disbelief. “That’s insane. It doesn't make any sense.”

He leaned closer. “Doesn't matter. I didn’t even wait. I had to come here as soon as she said it.”

I shook my head, grinning. “You’re as crazy as she is.”

He kissed me before I could say anything else. We never even kissed before this. But we were more "in the clear" than we ever had been, and I guess this was his way of bringing us back into the sexual side of things. He wanted to kiss me, I guess, so he did. I pressed my tongue back to him, feeling the peach fuzz on his face press against mine. It wasn’t a shy kiss. It was hungry and messy, like he’d been holding it in all day.

"I didn't cum with her," he said as he pulled off my face.

"What?" I said, my mind fogged and not understanding.

"I just ate her out. After she came for the first time, she was 'done' and we just cuddled. I'm so fucking backed up."

"I bet," I said, grabbing him.

I pulled him down onto the bed, and everything went fast. Clothes were gone, hands everywhere, my heart racing with excitement. It was sloppy and unfiltered, hormonal and in the moment, thinking only about our bodies. He crawled up over my face and presented his heavy package to me. It smelled like a male. It was that boy funk that I had gotten used to, and only briefly was afraid of losing. The brief time apart made me appreciate it even more, and I pulled him onto my by his hips. I nuzzled him with my face, feeling his giant cock spill drops of pre-cum against my cheeks and forehead. My lips mouthed against his balls, and my tongue coated them in saliva. His breathing was sharp as he held my head and guided me around his junk. I was lost in the smell of it all, the light hairs around his dick, the hardness that extended inside him all the way to his taint.

He pressed into my mouth and forced into my throat. I heard him exhale in pleasure as I gagged. I held his ass and pulled him in deeper. This night was going better than it started. I could tell from the involuntary pulsing of his meat pole that he was already close to cumming. I pushed him off of me.

"I want it inside me."

"You're a slutty hole," he said, as I flipped over and lifted my ass for him. 

Breathing, intermittent laughter, the creak of the mattress, his body slapping against mine. It was the loudest we’d ever been, reckless and sure that no one would hear or care. Every movement was familiar now, our bodies knowing where to go before our brains caught up. We didn’t bother trying to keep quiet; it felt too good to hide it.

I flipped over into missionary to watch his body tense as his thickness disappeared under my balls.

At one point, I said his name, just a whisper. His face softened for half a second before everything fell apart again into rhythm and pounding. He kissed me roughly and pressed in balls deep.

He grabbed the fleshlight from my bedside table, and spit on my dick, lining it up with the toy. He held balls deep inside me while he started to stroke me.

“I’ll cum right away like that,” I said.

“Me too,” he said back. He leaned forward to kiss me, somehow doing three things at once as he fucked me and fleshlighted me and massaged my tongue all at once. The sensation was too much and I groaned into his mouth as I started filling the toy. The orgasm felt more concentrated in my ass than my dick. It was pure pleasure in my body and I never wanted it to end. He pulled the toy off me and poured my huge load out, slowly. He dribbled it onto my abs, my dick and balls, and his own cock, where it met my ass. He used my cum as lube as he pressed into me again. It still felt amazing, even after I had cum, and fucked me quickly. I could feel him at the edge, and in a second he said, “I’m gonna cum inside you. Take my jizz.”

“You’re just a penis for me,” I said, conjuring up some new wording out of nowhere.

“I’m your cock,” he said. “You’re a loophole to pleasure my cock.”

“Cum in my loophole,” I said back, watching his face while he looked down at his cock going in and out of me.

“Fuck,” he said as he sped up and started throbbing inside me. It felt like I could literally feel his thickness unloading the goo inside me. I knew it was a huge load.

When his face finally softened, we were both drenched in sweat, slightly laughing and breathless. We didn’t say anything for a minute. He mumbled a quick “thanks” and kissed my cheek, wiping himself on his shirt and closing his eyes. It was late after all. The guy was tuckered out. He fell asleep fast, face down on the pillow, the curve of his back rising with each deep breath. I looked down his lean sides to the perky pillows of his ass. His whole naked body looked relaxed, like he had stopped overthinking things. I stared at the ceiling for a minute, just letting the pleasure wash through me, the relaxed post-orgasm feeling when everything is ok. My phone buzzed again.

Billy: Do you have a girl in there, or are you an animal with my fleshlight again? I think you’re gonna break that thing in half.

I burst out laughing quietly, trying not to wake Michael. I texted back: Don’t worry about it.

Then I put my phone on silent, rolled onto my side, and watched the way the moonlight hit Michael’s curly hair, his back and his taut ass. It was peaceful, whatever this was. 

I chuckled to myself as sleep took over. “Guess it still doesn’t count.”