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My Brother's First Time

Category:  BROTHERS 


    When Reed and I were left with no choice but to go live with our half-brother who we'd never met, I was super nervous about how the whole thing might go. We were used to strangers coming in and out of our lives thanks to our mom's many boyfriends, but we'd never met a half-sibling before. Thankfully, Darren turned out to be even better than we could've imagined. Not only was he an overall decent guy, but he was also gay, just like me. 

    The day after new met, I already felt comfortable enough to turn to Darren and ask him about the ins and outs of gay sex. He was 33, so I knew he had a lot more experience than I did. Being the cool big bro that he is, Darren even bought me my very first dildo that day at the mall. 

    From there, things went a bit further than just "cool bro" territory. Darren found out I liked to suck Reed off. Reed and I always knew what we were doing was weird, but we both enjoyed it so we saw no reason to stop. It wasn't long before Darren let me suck him off as well. Then, I finally lost my virginity when Darren and Reed both fucked me. I couldn't think of anyone I'd rather have my first time with than my two brothers! All of this happened within a few days of meeting Darren, so our relationship was definitely off to a sexy start.

    Now, two months had passed since Reed and I came to live with Darren. I couldn't say the three of us had sex every single day, but it certainly happened at least a few times a week. Darren and I took turns being bottoms; Reed continued to insist that he wasn't gay, he just "liked to fuck." I didn't exactly believe him 100% but I felt no need to force a label upon my brother.

    Tonight was Christmas Eve and for the first time ever, this felt like Christmas on TV and in the movies. Since we lived in Arizona we never got any snow, and our mom never bothered to put up decorations or cook a large family meal. Growing up, Reed and I got presents every now and then, mostly from school and other places that gave out free toys, but with no tree and no stockings it never felt particularly festive.

    This year however, Darren's condo was decorated top-to-bottom, complete with a fake tree and plastic wreaths on each door. The ornaments were just the right amount of kitschy and I loved it. Reed pretended like he was too cool for Christmas, but I could tell he was glad we got to experience this. He was still tattooing people and making more money than ever, which he used to buy the pile of presents waiting for Darren and me underneath the tree.

    Tomorrow we were scheduled to go to Darren's mom's house and spend Christmas Day with her side of the family. But for tonight, the three of us were on our own, watching TV all cuddled up on the couch. I was in my favorite spot, right in the middle. I rested my head on Darren's shoulder while using my right hand to idly trace the outline of Reed's dick through his gym shorts. 

    Like clockwork, Reed's dick hardened to full length within seconds. Under the blanket, Reed took my hand and shoved it in his shorts so I could grab onto his boner. By now, neither of us were paying attention to the holiday movie and Darren either didn't notice or pretended not to. Pretty soon, Reed had his shorts down and I was full-on jerking him off. You'd have to be in a coma to miss this.

    I sat more upright and reached over to Darren's crotch. By now, I felt comfortable being forward as I knew both of my brothers were into it. I cupped Darren's nuts through his boxer briefs, feeling the warmth from his sack. He didn't even budge, only gyrated his hips against my hand. I could feel his dick get hard and didn't waste any more time before sliding my hand under his waistband and freeing his meat. Just like a kid with new toys, I was perfectly happy with both of my older brothers' dicks in my hands.

    Darren pulled the blanket off us and tossed it to the side. This gave me much better space to work my brothers' cocks. My head swiveled back and forth between their crotches, my mouth already wanting a taste. Feeling festive and generous, I got on my knees in front of them. They sat closer together, tossing aside their respective shorts and underwear to grant me full access to their tools. 

    I put Reed's cock into my mouth first. Instantly, I got a whiff of his natural musk. He tasted slightly salty from a mixture of sweat and precum; the combination drove me wild. I felt a hand on the back of my head, I thought it might've been Darren's, and he encouraged me to bob up and down on Reed's meat.     

    Pretty soon, my eldest brother joined me on the floor in front of Reed. Reed spread his legs wide, giving us both plenty of room. Darren and I looked at each other and then both of our mouths went to Reed's heavy ballsack. I swirled my tongue around his nuts while Darren went even lower, lapping at Reed's smooth taint. This must've been a first for Reed, as he started groaning and used his hands to push both of our heads even closer. 

    Darren and I then worked our tongues up Reed's shaft before making out with his cockhead in between our lips. We each took turns deepthroating, making sure to kiss every time we swapped. Reed's cock was glistening with our saliva, and I knew I needed him inside me.

    "What do you say you give me a Christmas present early?" I asked Reed after feeding his cock to Darren. "Let me ride this dick."

    "What're you waiting for?" Reed smirked at me.

    I got up, pulling my pajama pants down before straddling my brother as he sat on the couch. I spread my cheeks and started to sink down but felt Darren's tongue first. I leaned forward and kissed Reed while Darren wet my hole with his mouth. Soon, I felt the familiar feeling of Reed's cock knocking at my back door. I sat down firmly with Darren guiding Reed's cock into my hole. I was so used to it that I was able to take the entire thing in one go. 

    Reed didn't waste any time and immediately started thrusting up into me. The force of his legs made me bounce like I was riding a horse. Darren was still on his knees behind me and every so often, I could feel his tongue on my crack as rimmed me at the same time as our other brother was fucking me. I was in heaven! I had to leave my cock alone or I knew I was gonna blow.

    "Alright, little bro, my turn," Darren announced after a while, standing up behind me.

    Regretfully, I dismounted from Reed, causing his dick to slap his abs with a loud noise. Next, Darren turned around and lowered himself onto Reed's cock. I saw Darren's face wince but then soften to pleasure as his hole accepted Reed's meat. Darren got one foot up on the couch and leaned his back against Reed's chest. He used his foot on the cushion as leverage to start bouncing up and down, his own hard dick going in circles. Not wanting to be left out, I got on my knees and popped Darren's dick into my mouth. Darren's up-and-down movement made it perfect for him to fuck my mouth.

    For the next half an hour, Darren and I took turns riding Reed's cock. The room started to smell like sweat and sex. Our bodies were slick with perspiration. We kept going until Reed signaled he needed a break.

    "Damn, you guys really love getting fucked," he said while we sucked on his balls and massaged his thighs. "What's it feel like anyway?"

    "Well, it probably seems scarier than it actually is, especially if you've never done any type of butt stuff before," Darren explained. "It's hard to describe, but it feels amazing when your prostate is stimulated like that. You can't really know until you've tried it.

    "Interesting. I think, uhh… I think I might wanna try," Reed suggested coyly, even blushing.

    Darren and I both sat back on our heels, exchanging eager smiles.

    "So, Landon, would you like to be the first guy that fucks your brother?" Darren offered, catching me off guard. Even though I'd fucked Darren a few times, I was kind of nervous about the prospect of fucking Reed.

    "Well, Reed did take my virginity, so it makes sense for me to repay the favor," I noted.

    We positioned Reed so he was on his knees on the cushions and his hands on the back of the couch. Darren went to find some lube while I feasted on my brother's virgin ass. I flicked my tongue across Reed's hole, making him shudder with pleasure. When Darren returned with the lube, he tapped my shoulder and squirted some of the gel directly onto Reed's hole.

    "Okay, we'll start slow," Darren coached. "Landon is gonna put his finger inside of you to help loosen you up. When he does, just try to relax and breathe."

    Darren nodded to me as if to say "you're good to go," and I used my index finger to gently penetrate our brother. I felt Reed tense, but I encouraged him by rubbing the small of his back. I got my finger in about two knuckles deep when Reed finally relaxed. I pulled my hand back and this time went in with two fingers. Reed gasped as he felt me stretch his hole. Darren sat on the couch, playing with Reed's cock and balls to help him relax.

    "Now, Landon, put just the tip in," Darren instructed. "Reed, I want you to push out from your ass, it'll help to let him in, got it?"

    Reed nodded, looking both worried and excited. I lined my dick up with his hole and squirted more lube on the head. I started to push in, slowly, painfully remembering what it was like my first time. I wanted my big brother to enjoy his first time.

    "Agghhh, fuckkkkk," Reed gasped.

    "Just breathe...big deep breaths," Darren whispered. 

    I stayed like that for a minute or two, letting my brother adjust to having a dick in him for the first time. Reed reached back and pulled on my hip as if giving me the okay to keep going. I held onto his hips and pushed in more firmly. I wasn't nearly as hung as either of my brothers, but Reed whimpered as I bottomed out. 

    "Fuckkkkk little bro, how do you do this with mine?!" Reed exclaimed. "But, fuck! This feels so fucking good!"

    I took that as my cue and started to slowly thrust in and out of my brother. Each time my hips met his ass, he grunted. I worked up a faster rhythm. Reed's grunts soon turned into moans. His cock bounced each time I slammed into him, making him drip precum onto the cushion. Darren bent down and took Reed's cock into his mouth, just like I'd done for him earlier. My brother's viselike grip on my dick was going to make me explode… and boy did I ever. 

    "Ahh, uhhh, I'm gonna, fuck, I'm gonna cum!" I cried out, shooting my load inside my brother's guts. At the same time, Reed moaned, shooting his own load into Darren's mouth.

    Suddenly, a knock at the door surprised all of us. Darren got up with a puzzled look on his face. He picked up his boxer briefs off the floor and he put them on, walking toward the door and opening it slightly, just enough to peek through. Then, Darren gasped loudly and only said one word.

    "Dad?!" Darren exclaimed just as I pulled my dick out of my brother's ass. 

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