Pretending To Be Gay 16

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Chapter 16: Afternoon With Landon

A couple days later I went over to Miles’ place to chill, but Landon was the one who opened the door. He told me Miles was out running errands, and when I checked his location he was way across town.

"Damn," I said, "I should've checked with him before just coming over."

He glanced at me and said, "You wanna hang out for a bit?" I shrugged, feeling like it might actually be cool to catch up with him one on one after everything that had gone down, in the basement, with him and Greg and all that.

"Yeah, sure," I said. The house was empty except for him. His mom had left lunch out on the counter, so we just sat together in the kitchen and ate.

We caught up a little while we nibbled on enchiladas. He mentioned that he and Miles had both come out to their mom.

"She said she had suspected about Miles but never saw it coming with me," he said giggling.

I chuckled. "That's funny. I guess I wouldn't know either until you came out."

There was a short silence, before I asked, "So... how did you and Greg end up hitting it off? I mean, I was kinda hoping you guys would hang out after finding out you're both gay. But I didn't even get a chance to play matchmaker, unless you count inviting you both to that party."

Landed chuckled and let out an exhale.

"Well," he started, "I guess it started when I caught the three of you guys fucking that one night. I had never seen anything like that in person. It was surreal to see guys in person, that I knew, all fucking, even if one of them was Miles. I recognized Greg from school and always thought he was so hot. But like, you're so hot too. I was basically cumming prematurely in my pants the moment I saw your guys' dicks and butts out and stuffing them into each other. Miles was giving it to you so good, and I just wanted to feel what that was like."

I nodded, remembering the night well, and getting a bit hard in my pants as he described it from his point of view.

"And then Greg was so chaotic and kinky with you guys, it made me think he could take two dicks at once or something like that. I jerked off twice watching you guys, then literally had to take a cold shower or I didn't think I would get any sleep at all."

I laughed out loud at that line. "Yeah," I said, "I remember catching you coming out of the shower, flashing me your cock."

"Fuck, that was an accident," he said, "honestly."

"I know," I said, "still fun though."

"Yeah, so, honestly," he went on, "I felt like Miles couldn't be the only one having fun, and started thinking about coming out and all that. Then you guys sprang it on me that one day, and I just thought it was time."

"That's awesome," I said, trying to encourage him a bit.

"Yeah," he went on, "so, I already knew Greg was gay, and you were with Miles anyway, so I shot my shot with him once I saw him at the party."

"Yeah, I saw that," I said, putting down my glass of soda. "You guys were glued together at one point, then obviously you ended up fucking in the back house not far from me and Miles."

"Yeah," I said, "Maybe I have some rizz, or whatever, but once Greg and I were in the hot tub I gave him some verbal hints, which he didn't perceive at all, then I just put a hand on his ass under the water. That did the trick and he smirked at me and started grabbing my dick. It was so hot."

"That's the best, dude," I said, "Miles and me actually first got together in that same jacuzzi."

"No shit, really?" he said, almost choking on a bite of enchilada.

"Yeah, last year one time, we jerked each other off. Well, I jerked us both off. It was awesome."

"I bet," he said, but clearly wanting to move on from talking about Miles.

"So Greg and I just chatted and played with each other under the water until we decided to find a place to actually hook up, and landed there in the back house with you guys. Then we snap chatted every night for a while and we decided fuck it, let's go to prom together. I don't know if we're boyfriends or whatever, but yeah we chat and hang out a lot. He's actually sort of scared of coming out in general, but he was down to do prom so we just did it. People at school don't seem to give a fuck. And yeah. It all started that night at your pool party."

He smiled.

"Yeah," I replied, "I actually saw you fucking him. You have a nice ass."

He blushed a little, "Thanks man, obviously you're so hot too. I was so happy I finally got to put it in you that one time, even if it was pitch black in that basement."

"Yeah," I said, "I actually wanted to know for sure if that was you. I can't tell your ginormous dick apart from Miles' in the dark."

We started cracking up. "What the fuck is my life?" I said between breaths. 

"I wanted to ask, by the way," I said after catching my breath for a second, "do you know who all came down into the basement?"

"Ummm," he said, thinking about it and still partially laughing, "I definitely know that guy Danny was down there. I felt his giant balls and heard him talk."

"Yeah," I said, "you and me and Miles and Greg is all I know for sure."

"Yeah," he said, "I think that's it, as far as I know."

"Right," I said, getting quiet for a second, then asking, "So did you accidentally make any contact with Miles?"

"Fuck off," he said quickly, but laughing a little at it. He took a sip of coke, then added, "Honestly maybe a little. I couldn't keep track in the dark. We just never talked about it." He paused for another second. "God I hope not."

"Yeah," I said, "me too." Then we paused.

"So," I said, "Are you fully gay, or like, into girls too?"

"Just gay," he said after thinking only a moment. "Never really liked girls. How about you?"

"I think I'm gay," I said, "'cause after being with Miles for a bit, all I think about is men. But I used to think I really liked girls. I guess I just went with the norm. But I thought guys were kinda gross until I started experimenting with Miles. Girls seem clean, guys are disgusting. I just learned that I like the disgusting stuff." 

He chuckled. "I guess I just always wanted another guy underneath me. So you only watched straight porn?"

I was getting hard again, talking with my boyfriend's huge-dicked brother about what we liked sexually.

"Well that's a blended history," I said, "there's like, femboys and stuff like that, which I convinced myself were straight. And occasionally I'd check out some celebrity men, but I told myself it was just because I wanted to look like them."

"Right," he said, nodding agreeingly. 

Landon pulled up a video that he described as his "gay awakening," and I recognized it immediately. It was a scene from Euphoria where Jacob Elordi was having sex. 

"Yessss," I said, smiling big, "I literally remember watching that. I got the biggest boner."

I looked down and saw Landon's dick stretching out down his thigh in his shorts. It was so similar to Miles'.

Before my thoughts went any further, I had to text Miles. My thumbs were literally shaking a bit as I typed: "Can I fuck Landon?"

He responded in seconds: "HAHAHAHAHAHAHA"

I waited, not sure if that meant yes or no. I saw the typing bubble pop up, and the next message came through.

Miles: "Fuck yes you can fuck whoever you want, even him, but I'll be home in like 10 mins so just stay ready for me. I'll take his sloppy seconds idgaf."

I dropped my phone, barely reading past "Fuck yes", and moved my hand onto Landon's thigh. He looked at me with a sort of concerned look on his face, then asked, "Would Miles be cool with—"

"Yeah, he said it's cool," I interrupted, moving my hand over his shorts up to his hefty erection, and squeezed it tight. He groaned and looked me in the eye. "Greg is cool with it too."

I smiled big. It was on. He leaned forward and stuck his tongue in my mouth. 

I reached under his shorts and he started purring into my mouth when my hand came in direct contact with his dick. He was already leaking pre-cum, quickly and heavily, just like Miles did.

He pulled away. "Let's go to my room," he said, "Don't know when mom will get back."

I followed him into his room, and we stripped off all our clothes immediately when we got in. He set his phone on his nightstand and started a facetime with someone. 

I started to ask "What is—"

"Don't worry about it," he said, and shoved his tongue into my mouth again, lifting my legs as he started to probe my butt with his hefty cock.

When the facetime was answered, I heard Greg's voice. "Hey baby what's OH SHIT, OH HELL YES, OK OK SHIT I'M GONNA RUN TO MY ROOM DON'T END THE CALL."

I ignored it, but kind of liked it. Of course Greg was a part of this somehow. That actually made it even hotter. Landon pulled a bottle of baby oil out of his night stand, and soon Greg was set up on his end, fully naked and on his bed, his erection standing proudly in the foreground of the video.

Landon started fucking me, and Greg stroked himself on the camera, mumbling things like "Fuck I wish I was there," and "Fuck I want that dick right now."

Landon was a wild one with the rest of us, but he fucked me much more tentatively than miles did. He put it in slowly, and opened me up gently. I pulled his head down to mine.

"I've had a big dick before," I whispered in his ear, "you can make it hurt just a little. I kind of like it."

He got into the swing of things pretty quickly after that and started really pounding me. It felt so good taking another huge dick like Miles'. He held my hips tightly, and he didn't stop and take breaks.

It felt weird doing sex without Miles there, but I was starting to feel a bit sex-crazed, and I wanted to see what Landon looked like when he was fucking. It wasn't a connection like I had with Miles. It was just getting off, like when Greg jumped into our lives.

Miles came home early and walked into Landon’s room. Landon froze, unlike his brother who always kept going like a wildling when we got walked in on. I smiled at Miles. He looked surprised for a second, like maybe he thought we'd be done already, then smirked at me and said, “Wow, who’s been a bad boy?”

He made no comment about doing things in front of Landon, and instead just pulled out his fat cock and shoved it in my mouth, holding my head, like he was punishing me with the thing I liked most in the world.

I turned around so I could watch the hottest thing in the world, two genetic lookalikes with the biggest dicks ever, getting ready to take turns on me, one slightly taller, the other slightly thinner. I lifted my legs, showing my hole already gaping a bit from Landon. "You think you guys can both fit in here... at the same time?"

"No??" Landon said, a confused look on his face.

"They do it online all the time," I said.

Miles shrugged. "I kinda wanna see it, if you can."

"Just try," I said, "we have a whole bottle of baby oil, and all the time in the world."

"On that note," Landon said, then walked to his door and shut it, latching the deadbolt.

"Good thinking," Miles said, and they high fived. Seeing Miles and Landon, standing above me with the biggest dicks ever, high fiving, gave me some rush of adrenaline and hormones I didn't expect. It was like I was a freshman on the hockey team and two seniors were going to show me the ropes, but in an anal sex way.

"Fuck me," I said, finding no other words.

Miles grabbed my thighs and pressed into me slowly. I loved this angle, he was hitting my favorite spot, the one that made me cum hands free before. 

"Ok," Miles said, "now you put it in."

"Ok..." Landon said hesitantly. He grabbed one of my legs and tried to squeeze in next to Miles, but only the tip of his cock touched my ass, barely grazing Miles' shaft sticking out of my hole. 

"Lemme try it this way," he said, climbing up over me onto the bed, standing one leg on each side of my body. He squatted down, so his ass was pressing into Miles' abdomen, but his dick touched my hole where Miles' was, and it actually seemed like it might work.

"Bro, your ass is all over me," Miles said laughing.

Landon laughed too, "Shut up you love it."

We all laughed a bit at that one. Miles slapped his ass with one hand.

"No stop I'm gonna fall over," Landon said through a chuckle.

I could sense Miles' apprehension through his stiff body language and mild noises he made, but Landon pressed on, pushing his steely rod, covered in baby oil, into my hole against Miles' cock. As soon as he lined up properly and I could feel it slipping in slightly, I tensed up.

"Fuck," I said, "That stings."

"Damn," Landon said, "though it was going to work." He shifted to get up.

"No," I said, "Wait. Just gimme a minute."

Miles leaned over around Landon and looked at me, a big smile on his face. Landon's eyes lit up too, they were both as excited about this as I was, and happy that I was willing to push through.

Landon lined up again, and Miles started pushing a little bit in and out of me. I grabbed my cock and rubbed it, which helped ease things as Landon started to press forward again. I was grateful for his tentative nature, because it felt like there was an entire jar of tomato sauce getting shoved up my ass, which wasn't far from the truth. But the stinging was already less than the first time he tried.

"Go a little more in," I said.

He looked down at himself, and pressed a little further. Soon he was a couple inches in. It wasn't exactly the most pleasurable feeling in my ass, but I knew I would never forget the experience. Miles started pressing in and out of me, while Landon had a few inches inside of me as well. Neither of them could go balls deep while their bodies were angled like that, so it was really more of a game of stretching out my hole. A few minutes went by, and it felt like the first time Miles fucked me, as the burning turned to numbness, and even a few flickers of pleasant tingles at times. I held Landon's hips, as Miles started going a bit faster.

Suddenly Miles pulled out of me.

"I have an idea," he said, "they normally do it like this in porn."

He picked me up, like I weighed nothing, a skill Miles always has when he's horny. He sat back on the bed where I was lying. "Sit on me facing him."

I leaned back in a reverse cowgirl, and slowly filled my ass with his cock. I always liked this position too. Once I was sitting on him balls deep, he pulled my body back to lay on him. He looked around me over my shoulder down at Landon. "Now lift his legs and put it in."

"Gotta go guys, I jerked off twice, thanks for the show," Greg said on the facetime before abruptly hanging up.

Miles looked over quickly. "Was he here the whole time??"

Landon and I laughed, as I lifted my legs. I could sense I was slightly bending Miles' cock inside my body doing this, and it was pushing every button I had inside my ass. It was so hot, I was leaking pre-cum like a faucet.

Landon got the idea and pressed his dick against Miles', trying to get inside my hole. It kept slipping out.

"There's too much lube, actually," Landon said, "same thing happened first time I fucked Greg."

Then he quickly wiped Mile's shaft and the area around my ass, completely unbothered to touch Miles' shaft, and pressed again against my hole. He finally pushed in. It felt so much easier from this angle, I felt like it was actually going to work now.

"That's not too bad," I said, "You can keep going."

The experimentation continued, as Landon started thrusting into my hole, and Miles started pressing upward in little humps into me, as best he could from underneath me. Landon started to fuck me fast, and I was able to stay hard and actually enjoy the sensation after a bit. This felt like it should be impossible, but I was making it happen. The theme of my life over the prior school year. 

Miles held me from behind, one arm across my neck like I was in a head lock. I was at the mercy of two studs who knew how to fuck, and they were getting all their pleasure from my hole, and it was starting to feel better over time.

I jerked my cock while they both humped into me, especially Landon, who was nailing me like he had something to prove. His legs were standing on either side of Miles', their bodies completely overlapping from the waist down, and when I looked down at the action going on at my ass, I saw their balls slapping against each other, no worries between them. It was so taboo and hot that I pressed myself over the edge without even expecting to.

"Fuck, I'm cumming," I said as I started to spray all the way up to my face, some even going over my shoulder and landing on Miles' face. I milked myself into a puddle on my abs as Landon started going ham on me, really ready to cum. Just when I realized that Miles had stopped thrusting altogether, and it was only Landon pumping my hole, I heard the tension in Miles' little whimpers in my ear.

"No, wait, fuck," he said, then he started cumming in my ass. And it was all because of the friction from Landon's cock rubbing against his, inside my hole. I could tell he didn't really want that to happen, but Landon was on another planet, just how Miles tended to be during sex, and he was doing his own thing. He came a moment later, without announcing it, just freezing inside me and throbbing while his face showed that he was on another dimension. The two cocks started to retreat from their maximum levels of hardness as Miles caught his breath under me and Landon's face turned toward coming back to reality. I felt the extra juice inside me lubricating their meats as Landon pulled out, letting the mixed cum run out of me and down onto Miles' balls and thighs.

I wondered what Miles would do, but his sex face was on, and he immediately flipped me over onto the bed and leaned into me, pressing the cum back inside my hole. I felt like he wanted another go at me after sharing me with Landon. Something was so hot about that, to be desired so much by two gorgeous guys that they became like zombies for my ass.

Landon left the room and I heard the shower start, while Miles was fucking me rapidly, already in his final phase of sex where he was going to pump my hole mercilessly until he came. When he wanted to bust a quick nut, nothing would stop him. In a minute or so, he stuck his finger in my mouth and grabbed my neck, finishing inside me.

We stayed still while his cock kept my hole open, and we both took a second to catch our breath. He finally rolled off me and slipped out of my hole, the sweat between our bodies allowing a feeling of cool air as we separated. I had never felt so stretched out. It really felt like losing my anal virginity the second time.

“That was so hot,” I said.

“It actually was,” he replied. He snapped a photo of me with remnants of cum all over my body, then showed it to me. My eyes and lips were cherry red and my skin was flushed. It looked like I had been in a fight, with red marks on my neck and shoulders.

"I wanna see my hole," I said. 

He smiled. "Ok."

I lifted my legs once again, and he took a pic and showed it to me. It hung open on its own, completely used and stretched open. It was so weirdly satisfying to see. I felt like I had accomplished something.

Landon came in a minute later with a towel on. He took one look at the two of us lying naked on his bed and gestured to Miles, saying, "ok, enough of that, no one wants to see that."

Miles rolled his eyes and stood up to leave the room, his big dick swinging and his perky ass bouncing as he crossed the hall back to his room. I stayed behind for just a second. 

"That was cool hanging out today," I said.

"Yeah, it was a blast," he said back with a chuckle. I walked out and turned toward the bathroom. I needed to wash off this layer of fun before it turned me into a gross monster. Miles joined me in the shower and we soaped each other up. I always get hard doing that, but my body had had enough, for now at least. He got to my ass and stuck a finger up my hole. It was so raw from the double pounding, but I let him do his thing. It was hot that he liked it.

—[]—

Later that night, I was chilling with Miles in his room. Landon had gone out with his friends, and their mom was downstairs watching TV or whatever she does down there.

I scrolled through some socials while Miles played some game on xbox.

"Brittany and Joey broke up and got back together again," I said, my tone hinting at how silly their whole situation was.

"Ha," Miles said, without even really laughing.

"Hey," I said. Miles didn't say anything, but he was listening.

"So you used to have a bunch of jerk off buddies right?" I asked casually.

"Yeah," he said, a hint of a smile in his voice. "Always been a thing with me."

"Do you still do it?"

"Ummm," he said, clearly unsure of how he wanted to respond.

"You do??" I asked, surprised, but also turned on.

"I mean, sometimes," he said, "like, it just happens."

"Who do you do it with?" I asked, my curiosity peaked. "How have we not talked about this?"

"Well you know I used to jerk off a bit with Joey," he said.

"Yeah, I know."

"Then, umm, the most recent one..." he said, pausing like he lost his train of thought, but obviously just not wanting to tell me.

"Who was it?" I asked. 

He sighed. "Johnny."

My head flinched in surprise. "The fuck? My brother? The fuck??"

I wasn't mad. I was just absolutely shocked. 

"When... why, I mean, how... but... what the fuck?"

I was at a loss for words, but my brain couldn't tell my mouth to stop. Miles' round ended and he put down the controller. 

"Yeah, so, I was wondering when to tell you, but, yeah. The other day. When you were downstairs doing homework in your basement and I was chilling in your room. Johnny and I started talking. And, yeah, it's like a law of physics with me. Guys relate to me and we open up and talk about porn and dick size and stuff like that and, we share some porn and get a boner, and like, if they're down for that kind of stuff, like not in a gay way, a lot of straight guys will just not mind whipping it out if the moment is right, and yeah."

I was a bit flabbergasted.

As much as I hated thinking about Johnny doing something like that, jerkbuds started to become a real idea in my head. My eyes narrowed as I listened to him explain how it happened, because I didn’t want to hear more about Johnny, but I did want to hear more about Miles jerking off with a guy. It was a conundrum. I mean, after the day with Landon, I guess it was only fair, as strange as it was.

"Johnny is straight, right?" I finally asked.

"Yeah," Miles said, "as straight as they come. It just happened that once. It's actually really common."

My mind couldn't exactly wrap around that, since the first time I jerked off with a guy, it was Miles, and it ignited hugely erotic feelings.

Still, my dick got hard as hell thinking about Miles jerking with another guy, especially because I didn't know about it until now, so I told him to go on. He said one thing led to another and they were talking about girls and porn. It was like the jerk buddy stuff he’d always done in the past. Share porn, see if they’re cool comparing dicks, then ask if it’s cool if you just jerk off next to each other.

“Whose dick is bigger?” I asked. Then I immediately laughed and jumped across the bed and slapped my hand over his mouth. “No wait, I don’t wanna know about his dick! I don’t wanna know! I don’t wanna know!” I repeated the phrase as I blocked his attempts to talk, and we just laughed while he tried to mumble something around my clenched hands preventing him from speaking.

We didn't successfully change topics until we got a text from Rob in a group chat with a pic of another load on his abs, saying "Night guys 💦".

I chuckled and shook my head. "What is going on with that guy?"

"I don't know," Miles said, stripping off his clothes and climbing into his bed with me. "I'm just glad he's not being all religious and threatening anymore."

"Yeah," I said, putting down my phone, "that was fucked."

I turned to my side and he put an arm around me as I drifted off.

—[]—

The idea of having jerk buds stuck in my mind after that. I wanted to know who of my straight friends would enjoy doing shit like that. I was just bi enough to enjoy pretty much whatever porn was on the screen, and maybe with Miles' social skills we could get something going. We talked about it a lot after that and I heard story after story of all the times he had jerked off with friends, even sharing a hand once in a while, and in rare instances, a mouth.

The month of May rolled on like that. Sweet mornings with Miles, Rob getting intermittently rowdy and making us laugh, and Miles and me talking about jerkbuds, subtly, perhaps subconsciously, planning to make it a reality. Senior year was winding down, graduation was coming soon, and things were changing all the time. So, who knew what could happen next?