SAWYER:

    "Ahhh, yeah. Fuck yeah. Fuck me, bro!"

    "Yeah, you like gettin' your ass drilled by your big brother, don't ya? Turn your face to the camera so they can see you."

    I did what my brother told me and I turned to the cam. There was no need to exaggerate the expression on my face; the pleasure that I was feeling as Kurt's cock ravaged my fuckhole was clearly visible. 

    It was Valentine's Day. My older brother Kurt and I had rented a hotel suite for the occasion. When we checked in, the receptionist assumed we were husbands since we had the same last name, and we just went along with it. 

    For the past five (!) hours, Kurt fucked me in the luxurious bed, in the jacuzzi, and up against the floor-to-ceiling windows overlooking Manhattan. My brother and I had been having sex for several months now, usually doing it at our apartment, so we wanted a change of scenery, both for our sake as well as our viewers'.

    "You want me to breed your hole?" Kurt grunted loudly. "You want to feel your brother's seed up inside you?"

    He was saying it like it was the first time, when in fact he'd cum inside me three times already today. 

    "Mhm. Please cum inside me," I begged, looking straight into the camera. With his hands on my hips, my brother's thrusting accelerated and it wasn't long until I felt his hard cock shooting inside me, filling me up with straight-man jizz.

    "Fuck yeah. Take that nut. Fuck yeah!" Kurt barked, thrusting rhythmically and emptying his balls inside of me. By the time we were done, our naked bodies were drenched in sweat, and mine had four fraternal cumloads inside of it.

    "See you soon, guys," was all I could say to the camera before switching it off. Then, my brother and I passed out on the bed. Neither one of us spoke for ten minutes while we caught a well-deserved break. 

    "Wow, that was amazing," I said finally. "Five hours of content. Even after we edit it down, that's enough for a month."

    "Only the best for our VIPs," my brother smirked. "But I gotta get going. I'm shooting with Jessica soon."

    "After all of THAT, you're gonna have more sex?!" I asked in shock. "Haven't you literally run out of sperm?"

    "Nope, thanks to those supplements I took," Kurt said. "Besides, I made a promise to Jessica and I'm not gonna leave her high and dry. We're live-streaming tonight for Valentine's Day. She decorated her room with all these roses and balloons and shit," he chuckled. "My videos with her are usually the most popular. Other than my videos with you, of course."

    He was trying to sound nonchalant, but I could tell my brother was really falling for Jessica by now. I saw it as a good thing. With a career like his, Kurt would have a hard time finding a girl who would be understanding and approving of what he does, and that wasn't a problem with Jessica who did the same thing (except that, as far as I knew, she didn't have sex with any of her siblings on camera).

    "Speaking of Jessica," Kurt continued, "she asked me to do something and I wanted to run it by you."

    "Oh. What is it?" I asked.

    "She wants to fuck me. Like, use a strap-on or a dildo or whatever on me," my brother said, and I could feel my eyes growing bigger. "A few months ago she did it with this other guy and those videos did really well. She wants to do it with me now, and people have been asking for it."

    "And how do you feel about that?" I asked my brother.

    "I'm… conflicted. Like, I'm not totally opposed to it, but I don't want my first time to be on camera. Honestly… I was wondering if I could practice with you first." 

    "You want me to… practice fucking you with a toy?" I asked. "I mean, I'll do it, but why don't you ask Jessica? Your first time doesn't have to be on camera."

    "It's because… I feel the safest with you," my big brother admitted, and it made my heart melt. I leaned in closer to Kurt and gave him a big hug.

    "Okay," I agreed. "I already have the perfect-sized toy to start with."

—

    A week later, my boyfriend Brock was at work and Kurt and I were home alone, ready for an afternoon of anal action. Towels were laid out on my bed, next to the lube and poppers and one of my smaller dildos from years back. 

    "Have you been taking those fiber supplements I gave you for the past two days?" I asked Kurt as we both stood naked in the bathroom.

    "Yes," he nodded. "Not to get too graphic but PHEW, they really made me go."

    "Good. Now I want you to use this," I said, handing him a douche bulb. "Did you watch the video I sent you?"

    "Yeah..." my brother said, looking a little dubious. "It seemed pretty easy, and this little thing is pretty thin." He poked at the nozzle with his finger, and then shot me a here-goes-nothing look. "Could you maybe... um... just put it in? The first time? Just so I know how it's supposed to feel?"

    "Sure," I said, smiling and taking the bulb from him. He turned around and bent over, and I got a nice look at his clean and somewhat hairy hole. My eyes, fingers and tongue were all very familiar with this part of my brother's body. But even so, the excitement of today made this feel new and thrilling.

    Feeling like some sort of doctor, I slid the thin tube into Kurt slowly, and then let him experience how it felt to be filled up by the warm water. When it was time to let it out, he said I could leave, and I waited on the bed for a while until he was finished. My brother emerged from the bathroom looking proud of himself. 

    "That went better than I thought," he said, and I was glad I'd thought of doing the fiber supplements. I thought briefly about the hours I'd spent prepping as a teen, before I really knew what I was doing, and I was glad that I was able to help Kurt graduate to this next level pretty quickly.

    I told Kurt to lie on the bed on his back, and had him slip a pillow under his lower back and spread his legs. With some lube, a bottle of poppers handy, and of course the small dildo, we were ready to get going. I applied the slick lubricant to my brother's twitching hole, and it was incredibly tempting to just slide a finger right in. It would have been quick and easy, but I also knew that I needed to stay focused on the task at hand. This was a training, and Kurt needed to learn how to take something bigger and longer than a finger.

    "AHHH!" my brother twitched as I inserted the tip of the lubed up dildo in his asshole.

    "Relax," I guided him. "Take a hit of those poppers like you've seen me do if you want."

    Kurt heeded my advice. After about a minute, his hole was relaxed enough to allow half of the butt toy to slip inside. I looked at my brother's face, which seemed confused, as if he was trying to decide whether he was enjoying this or not.

    "How's it going?" I asked.

    "It's… alright. I'll tell you to stop if something's wrong. Everything's cool so far. You can… uhhh… you can actually go a bit deeper."

    I smiled and drove the dildo further up my bro's hole. As much as I tried to "remain professional," the sight of Kurt's ass being penetrated made me pop a boner. My brother, on the other hand, seemed too nervous to get aroused. His dick stayed soft while I worked his ass for ten minutes. But then, after a while, Kurt's cock started to chub up as well.

    "Ahhh… Does this usually take this long to get used to?" Kurt asked. My brother was very competitive. 

    "Every guy is different", I said to him. "Some take to this quickly and get to enjoying it almost right away. For others, it can take longer to learn how to relax and really let someone – or someTHING – inside you."

    Indeed, once Kurt was able to let his apprehension go, things became easier.  I was able to slide almost three quarters of the toy in before meeting any resistance, and each insertion was still going further in than the last had.

    My cock was swelled to peak erection, and I started to use my free hand to jerk myself off. I loved these times when Kurt and I played around and the camera wasn't on. My brother's enthusiasm hardly felt fake or forced when we were shooting, but whenever it was "just us," he seemed even more relaxed and willing to let himself get lost in what we were doing.

    It was clear from Kurt's boner – which was now as hard as mine – that we'd found a good angle and rhythm. My brother was even fucking back onto the dildo a little, and I could tell he was eager to keep the new sensations coming. All of a sudden, he gasped and I saw a thick glob of fluid squirt from the tip of his cock and land on his abs. It was clear and viscous, and it was more precum than I'd ever seen come out of my brother's cock at one time.

    "Your cock is dripping like crazy, Kurt," I said with genuine admiration and arousal in my voice. "This must really be doing something for you."

    "Jesus, dude..." my brother moaned, sounding like he was almost at a total loss for words. "I've never felt anything like this. I had no idea. Fuck... I'm starting to see why you like this so much."

    "Yeah?" I smiled as I felt my cock getting even harder in my hand. "Am I gonna turn my studly big brother into a bottom slut?"

    Kurt couldn't help but laugh at my choice of words, and though he didn't answer my question I could almost feel the wheels turning in his mind. I wondered if this anal play would remain confined to his scenes with Jessica, or if he'd be open to including it in his videos with me eventually.

    "Oh man, I'm getting close," Kurt moaned after a few more minutes of me slowly siding the dildo in and out of him. My fingers that held the base of the toy were now brushing up against the edges of my brother's hole.

    "You're taking all of it now, you know," I said in a low voice. "Your ass is gonna do just fine with whatever Jessica whips out."

    "I knew you'd help me be ready for this, Sawyer," my brother said, sounding more and more breathless with every word. "You've shown me so much and... mmm... I love that I have you as a teacher and a... oh fuck!"

    Kurt let out a string of obscenities and the expression on his face became a mix of ecstasy and surprise. Suddenly, his rock-hard cock began blasting cum all over his chiseled abdomen. I realized I'd never seen Kurt cum handsfree before, and I wondered if I was witnessing the first time it was happening for him. His back was arching from the intensity of what he was feeling, and I watched a jet of cum leave his dick and fly over Kurt's head, hitting the wall behind his bed. Part of me wanted to lean forward and slurp that gorgeous member into my mouth to get the rest of his load, but I knew Kurt needed to feel the rest of this orgasm rock his body and understand what was possible just from anal stimulation.

    Seeing my straight brother in this state was enough to push me over the edge as well. I felt it coming so I got upright on my knees, my cock pointing right at Kurt. When I started shooting, my load landed straight on on my brother's ass, including the parts of his ass lips which were currently getting stretched out by the dildo. Just then, I pulled out most of the dildo and continued to shoot my cum right on it, before driving it back inside my brother's ass.

    "AHHHH!!" Kurt shouted loudly a minute later when I pulled the dildo out of his ass. The toy no longer had any of my jizz on it – it was all inside Kurt's ass now. 

    "Wanna take a shower?" I asked my big bro, slapping his ass as if to say "job well done."

    "In a minute. Let me lie here for a sec," Kurt panted, closing his eyes and turning to his side. 

    I put the dildo down and climbed onto the bed, cuddling up next to my brother and spooning him from behind, my still-hard cock resting between Kurt's freshly stretched out cheeks.