"So you gay, huh?"
"What?" I almost choked on my breakfast cereal when I heard my half-brother Reed ask me that out of the blue.
I felt like I'd been caught red-handed. Less than nine hours ago, I'd spied on Reed getting his dick sucked in this very room. Did he catch me looking – and enjoying the show? After all, I'd been jacking off while playing voyeur, and I bust my nut at pretty much the same time Reed did.
"We checked your DVR last night and found a bunch of those drag shows gays like to watch," Reed continued with a grin. "It's aight, we don't judge."
"You can't tell if someone is gay by the shows they watch," I said with a paternal tone of voice. "But yes, I am."
"Cool. Landon's gay as well," Reed added, acting like his little brother's spokesperson. Interestingly enough, Reed had outed Landon, but he never mentioned his own sexuality. I made eye contact with a blushing Landon, as Reed continued stirring the pot by saying, "You guys can go cruising together."
"That's not funny. How do you know about cruising anyway?" I asked.
"I'm 17, not 7," Reed rolled his eyes. Once again, he was sitting shirtless in front of the TV, eating cereal along with his shier brother. I sat on a chair a few feet from them, trying to get the image of the blowjob I'd witnessed out of my head.
"Can we go to the mall today?" Landon asked, potentially looking to change the subject. "There are some things we need to get."
"Sure, I can drive you there. But where do you guys get money from?" I asked my half-brothers. "You got jobs?"
"Yeah," Reed nodded without offering any further detail.
"Well, what do you do?" I pried.
Reed let out a loud sigh before answering my question. "We do tattoos, okay? We got a tattoo gun a couple of years ago and we've been tattooing, usually people our age."
"That's really dangerous!" I exclaimed.
"Relax. We know what the fuck we're doing. I've literally done hundreds of people by this point and there's never been an issue," Reed assured me. "We need to get some more supplies, so if you can drive us to the mall we can pay you for the ride."
"It's fine, Reed, you don't have to pay me to do things for you," I said. I found his constant offering to pay me for everything quite endearing, but also kinda sad. I suspected when their mom was around, she expected the boys to pay her for anything they needed.
A couple of hours later we were at the mall, where Reed announced he wanted to do his shopping on his own and he walked off. I found myself alone with Landon and when I asked where he wanted to go, he said "the food court." For someone as skinny as he was, he sure could eat! Barely two hours after breakfast and he was chowing down a double cheeseburger across from me.
"Landon, can I ask you something?" I said with a discreetly low voice. "Is your brother… treating you alright?"
"What do you mean?" the 16-year-old asked.
"Like, he never makes you do things you don't wanna do?" I asked. With Reed being such a dominant personality, I was concerned about Landon and I wanted to make sure he was alright.
"Oh, he can be a dick sometimes, but he's alright," Landon replied after swallowing a large chunk of his burger. "He looks out for me. Our mother used to have a loooot of men coming and going, and some of 'em were real assholes! But Reed always stood up for me. He likes to act tough, but he's a good guy."
I was surprised to hear Landon speak so candidly, considering ever since we met he'd been quiet for the most part. I wondered if it had anything to do with him learning I was also gay that made him feel more comfortable around me.
"So those assholes you mentioned… was our father one of them?" I asked the teen.
"I dunno, you tell me," he shrugged. "We ain't seen much of him. He'd show up every now and then, but it's been years since the last time. He never beat us or anything, if that's what you're asking."
I sighed with disappointment. "Never beat us" was a really low standard to set for a father, but I guess that was as much as I could expect. At least I knew he treated the rest of his children the way he treated me.
"Do you know how many kids he has?" I asked, curious about my family tree.
"No idea," Landon shook his head. "We saw this girl once at Walmart who looked around Reed's age, and our mom told us she was our half-sister. I think Mom and the girl's mom were knocked up at the same time."
"Classy," I said sarcastically. I couldn't help but let out a laugh.
"I know, right?" Landon laughed along. "At least that's the upside to being gay: no unwanted pregnancies."
I nodded as I sipped on my milkshake and then, for the second time today, I almost choked when Landon asked me an unexpected question.
"Darren… are you a top or a bottom?"
"Um, well... that's a very personal question," I stuttered. "Why do you ask?"
"I just wanted to know if it hurts. Having sex," he continued.
"What you mean?"
"You know," he whispered, looking around to make sure no one was close. "Takin' it up the ass. I've never done it before."
Was I really about to explain bottoming to a teenager – who was my half-brother on top of it?! This was wild, day two of being a big brother and my younger sibling wanted to know if I've ever been fucked.
"Um, aha, well," I chuckled nervously, feeling sweat on my forehead. "It can be painful, but there are a lot of things you can do to make it as comfortable as possible."
"Like what?" Landon chirped.
Our nearest neighbors were all several tables away, so I knew we wouldn't be overheard, yet I still hesitated. My hesitation stemmed from the fact that – biologically related or not – Landon was a near-total stranger to me.
"Lube, and lots of it, especially if the other guy is hung," I suggested, remembering my first time. It was during my freshman year of college with my dorm RA. He was shy like Landon, kinda geeky but surprisingly well endowed. I'd caught him jerking off in the shower, one thing led to another, and bam, I was no longer a virgin. Unfortunately, being in the showers, we didn't have access to lube and it hurt like hell. "Foreplay is really important, too," I mentioned.
"What's foreplay?" Landon asked, looking confused.
Seeing how interested he was and considering the fact he didn't seem embarrassed, I started to feel a bit more comfortable in sharing. I was impressed at how much Landon seemed to think of me as an authority figure already, almost like a son looking for advice from his dad. I liked to think of myself as trustworthy and decently experienced in life, so I was glad it was me filling him in rather than someone at school or online.
"Foreplay can be a lot of things. Kissing, touching, stuff like that. Though, with bottoming, that means rimming," I explained. My college RA never bothered to rim me that first time. He just slathered some shower gel on his dick and shoved it in. In the years since, I'd come to learn I loved rimming – both giving and receiving it. Nothing turned me on more than getting my tongue at a tight, smooth hole. I loved a guy sitting on my face before sitting on my dick; and I could get my ass eaten for hours as well. Landon, meanwhile, continued to look confused.
"Rimming is when you lick a guy's ass," I explained as Landon shifted closer, eager to hear more. "Just like how women like getting eaten out, guys like getting rimmed. Sometimes the guy doing it likes it even more than the one getting it. The last thing, probably the most important, is to go SLOW."
Landon nodded silently and looked down at his food tray.
"So, do you have a boyfriend or something?" I asked, breaking the silence.
"Wellll, there's one guy I'm really close with," he said vaguely. "We've messed around a few times, but I really wanna go all the way with him."
"Just make sure you're ready," I said, sounding like a real dad. I finished my milkshake and while Landon polished off my leftover fries, I wondered if he was talking about Reed. Of all people, did Landon want his older brother to take his virginity?! I knew I couldn't ask that, not without outing myself as a spying creep. Instead, I decided to do something proactive and I made an offer to Landon. "I tell you what, while we wait for your brother, why don't we go get you some lube?"
My half-brother perked right up. He grabbed both our trays and raced them over to the trash. Together, we made our way to a store that sold lava lamps, novelty sex items, and other random crap. The place was darkly lit, which helped give it an air of anonymity. All the naughty stuff was in the back, so that's where we headed. Luckily, we seemed to have the place almost to ourselves. The store had a wall of lube, sex toys, and edible underwear.
"I'd suggest getting something water-based," I mentioned. "It's less sticky than the other stuff."
While Landon explored, I busied myself with reading through some of the dirty birthday cards, admiring the naked men and crude jokes. After a while, I noticed Landon had picked out a bottle of lube and was now eyeing a selection of dildos. One of those also might help get him ready for his first time. I came up behind him as he was inspecting a twelve inch "Mega Dong."
"You might wanna start off with something a bit smaller," I whispered in his ear, making him jump and laugh at the same time. "That six-incher next to it might be easier."
Landon smiled, reaching for the dildo without picking it up from the shelf. He looked at me, and I knew exactly what he was asking. With a smile, I took the lube he had picked as well as the 6" dildo and an anal douche, and I went to the register to pay for them while he waited for me outside. The stuff came in a discreet black bag that didn't give anything away, so I handed it to my half-brother outside of the store and we quickly headed back to the food court.
Reed came to meet us there not too long after. The three of us made our way back to my condo in the later afternoon. Landon rushed inside, saying he needed to take a shower. I noticed he brought the shopping bag with him. I wasn't surprised he was eager to try out his new toys.
I distracted myself with cleaning and other chores while Reed lounged shirtless on the couch in loose basketball shorts. He lay on his back with his legs splayed out, his bare feet close to him and his knees bent. When I looked over at him, I could see he wasn't wearing underwear, and when he shifted his weight slightly I watched as his long soft dick slid down to rest against his thigh. I licked my lips before I could catch myself and I quickly looked away, needing to adjust myself.
Landon finally appeared after nearly an hour and a half, but I didn't draw attention to it. I started making dinner and surprisingly, Reed offered to help. It was obvious he didn't know his way around the kitchen other than to use the microwave, so I taught him some of the basics of cooking. His prominent bulge was clearly visible the entire time, but I did my best to keep my eyes on the vegetables I was cutting, hoping I didn't lose a finger. Later, I had him finish the salad for me while I made meatloaf. Landon joined us just as everything came together and we sat at the table to have dinner. The boys took care of the dishes and afterward they showed me photos of some of the tattoos they'd done. I had to admit they were quite good, especially Reed's work. I still didn't like the fact they were doing it under the table without any kind of insurance, but I couldn't blame them for needing to make some money. From what I could gather, neither their mom nor our dad ever gave them anything.
Once again, the boys outlasted me at night, and I left them alone to finish the movie they were watching. As I left, I saw Landon rest his head on Reed's shoulder. In a somewhat tender display, Reed put his arm around his younger brother, letting Landon rest his head on his lap. I was glad they had each other, and as I went to bed, I fell asleep with the mental image of Landon resting on Reed's thighs. The image turned into a dream where Landon started blowing his brother, right there on the couch.
I woke up not too long after falling asleep, hard as a rock. I felt like I needed to check that the boys had turned off all the lights and electronics… or maybe I was curious to see if I might catch them in the act again? Leaving my room, I could tell that the TV was off, as were nearly all the lights. In my guest room where the boys were staying, I could see a thin line of lamplight escaping from a crack in the door. I crept stealthily to the doorway and I was able to peer in. The boys were on the bed, sideways to me, both completely naked. Landon had Reed balls-deep down his throat, while Reed leaned against the headboard with his eyes closed and moaning softly. Reed kept both hands on the back of Landon's head, guiding him up and down his teen meat.
"Ready for me to eat your ass?" Reed whispered and Landon looked up at him, Reed's dick leaving his mouth with an audible pop.
"You mean it?!" Landon questioned, excitement shining in his eyes so brightly that I could even see it from where I was standing.
"Well, you're always giving me such bomb head, I figured I'd return the favor," Reed winked. "Stay on your hands and knees and face the window."
Landon did as he was told and I was treated to a view of his perfectly smooth ass and hairless hole. His unused pink pucker winked at me, causing me to salivate and making my dick throb harder.
Reed got to his knees behind his brother. The bed wasn't that high, so Landon's ass was right at his face-level. Reed placed his hands on each of Landon's cheeks and spread them wide. As he leaned in, I was given a second hole to stare at, almost as hairless as his younger brother's. Landon moaned when Reed's tongue made contact with his hole. Reed began to hungrily munch his brother's ass, making Landon squeal in pleasure. My eyes darted between Reed exercising his tongue, to Reed's hole that gaped and winked at me, to his hanging ballsack and erect dick that was streaming precum onto the carpet.
"Oh fuck, Reed! I can feel your tongue inside me!" Landon gasped. "Darren was right, this really does make my hole relax. It feels more… ready."
I was surprised to hear my name. I hadn't even noticed, but my hand was down my underwear, just like last night when I watched these two. I tugged at the waistband and let the fabric fall to my ankles. With my dick free, I started slowly stroking as I watched Reed continue rimming his brother's hole.
"Oh yeah? Ready for what?" Reed asked cheekily, getting to his feet and slapping his thick young dick against one of Landon's asscheeks, leaving a smear of precum. "You want me to fuck you or somethin'?"
"I thought maybe we could try this first," Landon replied as he reached under one of the pillows, pulling out the lube and dildo I'd bought him earlier.
Reed took both items from Landon, examining the dildo with amusement. Reed sat on the edge of bed, keeping one leg up and the other with his foot on the floor. I had a great view of his muscled torso and veiny dick right next to his brother's exposed hole. Landon wiggled his butt in anticipation as Reed dribbled lube first onto Landon's hole and then onto the toy. Reed tentatively pushed the head of the rubber dick onto his brother's ring. His arm muscles tensed when he found resistance.
"Relax," Reed soothed, rubbing his brother's back.
Reed tried again, and the tip finally penetrated Landon, who gasped in shock and took a sharp inhale. I mentally willed the two of them to go slowly.
"Does that hurt? Are you okay?" Reed asked with concern in his voice.
"It's alright. Hurts a little bit, but keep going," Landon encouraged.
Reed kept pushing the toy inside his brother until another inch disappeared
"Wait, just keep it there for a sec," Landon asked.
I could hear him taking deep breaths. It was confusing for me to feel concern, care, and lust all at the same time, but I was loving this live show. Landon nodded and said something I couldn't quite catch, but Reed once again started pushing the dildo inside him until all six inches were inside Landon's virgin chute.
"Ahh, it feels... good!" Landon finally exclaimed.
Next, Landon tried to push back onto the dildo to get even more of it inside him even though it was already all the way in. Reed, sensing his younger brother's readiness, started to gently pull the dildo out before easing it back in. I was proud of him for still going slowly, even if the toy was rather slender. Soon, Reed worked up a steady rhythm as Landon became more and more loose. Reed kept one hand on the toy and the other gripped his own dick.
"Stop, I wanna try something," Landon implored.
Reed pulled the toy out of his brother and I watched Landon's hole briefly hold the gape before sealing shut. Landon then got down to the floor on his knees, fitting comfortably between Reed's legs. He took the dildo from Reed and balanced it on the carpet. I watched my youngest brother slowly ease himself onto the dildo, accepting it back into his asshole. He took Reed's hard dick into his mouth, simultaneously deepthroating Reed and slamming his ass down on the toy.
As his head bobbed up and down on Reed's thick rod, Landon rose and sank onto the rubber boner. Landon's movements became faster and faster. He gripped one of Reed's thighs for balance while jerking himself off with the other. Reed had both hands on Landon's head with two fistfuls of hair, his eyes scrunched closed and his face contorted in ecstasy. He must be getting close! With a stifled groan, Reed shot to his feet and clamped his brother's head against his pubic region, depositing his load down Landon's throat with a loud "Fuuuuuck." As he swallowed his brother's seed, Landon blew his own load onto the carpet, just as I was erupting and spraying my cum on the outside of the door, missing my hand. Still in the midst of my orgasm, I knew that I had to get rid of the evidence swiftly. I tried to use my free hand to wipe my jizz off the door, but the door moved with my touch and opened with a loud squeaky noise.
That's when two sets of eyes shot right in my direction, and two teenage voices said,