ISAAC:

    I was looking forward to a fun Friday night. For once, I actually had a date. She was a woman I'd met through a mutual friend, and while I didn't think there was much of an initial romantic spark, she was smart and fun to talk with. So the evening promised to be a pleasant one no matter what.

    Well, it would be if I could manage to get into the bathroom to shower and shave. I had to leave in an hour, and Eli had been in the bathroom for quite a while. He was heading to Noah's house for the night. That had been his plan anyway; Noah's mom was out of town and so it was just his older brother Jacob there with them tonight. But the added bonus for me was that I could bring my date back here if things started to swing that way, and we'd have the place to ourselves. I had already straightened up everything in the living room and my bedroom twice and vacuumed the entire house. With nothing else to busy myself and time running short, I finally stripped down to my boxers and knocked on the bathroom door.

    "Hey Eli, what's up?" I asked, sounding a little impatient. "You've been in there forever and I've still got to get ready. Can you hurry up?"

    "Yeah, I'll just be another second, Dad," he replied. I waited there for about two minutes and was about to knock again when the door opened. My son stood there with a towel wrapped around his waist, his wet hair neatly combed and a smile on his face.

    "Sorry, Dad," he said. "I was just... getting ready."

    "Getting ready for what?" I said, a little curious. "Going to Noah's? Are you guys going out somewhere tonight?" I was fine with them being over there with just Jacob for the night, but I didn't want them going somewhere else without me knowing where it was.

    "No, we're just going to be at Noah's," he said, and I could tell he was being truthful.

    "Okay," I responded, my curiosity still not satisfied. "Well you were in there for a while, and I heard the toilet flush three times and the shower go on and off at least twice. Are you okay? You're not feeling sick, are you?"

    "No, I feel fine," he said, shaking his head and suddenly looking a little timid. "I just... needed to get ready."

    "Get ready for what?" I asked again.

    "We're going to... I mean..." he said haltingly, before taking on a determined stance and looking me right in the eyes. "I was going to tell you tomorrow, but... Noah and I want to… do it tonight."

    That caught me off guard. I knew he and Noah did plenty of messing around. I'd even seen them doing things, though they didn't think I was awake at the time. I'd always figured that they might eventually fuck, and sometimes wondered if they already had. But clearly they hadn't yet, and now here it was. The big day.

    "Oh," I said. "Well that's... great. I mean... it is, right? Are you... excited?"

    I realized that was a dumb question to ask a sixteen-year-old, and Eli's face confirmed that assessment.

    "Uh, yeah," he said, raising one eyebrow and sounding sarcastic. "I'm sooo excited, Dad."

    We both laughed and that helped the awkward moment pass. And then I had a realization.

    "So, all this time in the bathroom," I began, "you were..." I trailed off, not sure what word to use. Cleaning? Preparing?

    "Getting ready," Eli repeated the words for the third time, nodding comically and briefly taking on the tone of someone talking to a child. He's almost grown up now, I thought to myself, with a mix of pride and sadness.

    I smiled again at him, not sure what else to say. So I went with saying how I felt.

    "I love you, Eli," I told him, and pulled him in for a hug. He let out a classic teenage groan, muffled since his face was pressed into my chest. But he hugged me back.

    "I love you too, Dad," he said, sounding surprisingly sweet. I felt his lips against my skin and chest hair as he spoke, and I realized I was holding him pretty tightly. I let go and he pulled away, a smile on his face.

    "Alright well... I've gotta go get ready," I said.

    "Oh really?" he replied with a teasing tone, his eyebrow going up again. "Are you gonna get lucky tonight too?

    "That's none of your business!" I said, laughing, and I smacked his towel-covered butt playful as he turned to head down the hallway. He snickered and looked back at me with a wide grin before going into his room.

    I stepped into the bathroom and took a look at myself in the mirror. "I still have it, right?" I silently asked my reflection. Maybe Eli wouldn't be the only one getting lucky tonight.

 

ELI:

    Noah was snoring already, just a few minutes after falling asleep. We'd been cuddling in his bed after he fucked me, and he had passed out pretty quickly. I was wide awake though, thinking back over what had just happened. I knew tonight was a big deal for both of us, but I couldn't help thinking that it was a bigger deal for me. Noah had fucked a guy before, after all. A guy he'd met in his summer program last year. He didn't act like he was an expert or anything, but he had clearly enjoyed being the more knowledgeable one.

    It had been... fun. We'd made out, gone down on one another. I put on my red jockstrap — the one I'd gotten from the store clerk — and then he'd licked and fingered my hole for a while, which felt great. I loved wearing the jock when he did that; I'd quickly found that wearing it was always a turn-on for me no matter what I was doing. We got some lube and then... we did it. I had been on my back on his bed, with him standing at the foot of the bed. He held my legs and slid into me pretty easily. And that was it. I wasn't a virgin anymore. The rest of it was pretty cool, feeling him inside me, all the sensations on my hole, and then feeling his cock seem to get bigger right before he shot his load in my ass.

    He pulled out and we kissed some more and laid down on the bed together. I'd already told him that he didn't need to make me cum, that we could do that later. I really had just wanted to enjoy the experience. And I had. Hadn't I? I didn't not enjoy it. I guess I had just been expecting... more. But more of what? Fireworks? Uncontrollable moans of ecstasy? I knew it wasn't going to be like it was in porn. But maybe I should have been jerking myself off while we did it. Or something? I could try that next time.

    I suddenly felt thirsty and I began to untangle my arms and legs from Noah's so I could get up. I opened the bedroom door and the house was dark. Jacob had said he'd sleep in their mom's room tonight so that we could, as he put it, "have our fun." He knew what we had planned and he'd teased us a little bit, but he was cool enough not to make a big deal of this, which I appreciated. I actually secretly liked knowing that he was in the house with us while Noah fucked me.

    Still in just the jockstrap, I walked quietly to the kitchen to get some water. The front of the house was an open floor plan and it seemed dark and cavernous as I made my way to the cupboard to grab a glass and then fill it up at the sink. As I took a few sips, a voice from the shadowy living room startled me.

    "So how was it?"

    I jumped and almost dropped the glass on the floor. I looked over and I could barely make out Jacob's shape on the sofa. He must have decided to sleep out here.

    "Jeez!" I said to him. "You scared the shit out of me!"

    "But not the cum, I hope," he replied in a joking tone.

    "Very funny," I retorted, and then drank the rest of my water. As I did that, he got up from the couch and came to the edge of the kitchen area. I could see him a little more clearly. He was only wearing a pair of boxer shorts, the ones he always slept in.

    "So," he continued after staring at me for a moment. "How was it?"

    "It was great," I replied quickly, then realized how generic that sounded. "I mean... it was awesome. Really fun." Ugh, I sounded like such a dork.

    "'Really fun'?" he repeated, slowly. "Wow, yeah. Sounds like it was mind-blowing."

    "Look, it was fine," I said, feeling a little defensive. "I didn't expect it to blow my mind. It felt good, I liked it. Okay?"

    "Who are you trying to convince, man?" he asked, with a tone I couldn't quite place. Part of me realized that was a legit question, but I pushed those thoughts aside for now.

    "We can't all be the school man-ho right out of the gate like you, Jacob," I said, trying to match his conceit, and starting to feel a little pissed. Who was he to make fun of me, anyway?

    "Whoa, whoa, Eli," Jacob said, holding up his hands and walking closer to me. "I'm sorry, I didn't mean to come at you that way. I just... wanted you to have a great first time, I guess." I was silent for a moment and just looked at him. He wasn't razzing me anymore, and he seemed genuine.

    "Well it was cool, like I said," I responded eventually. "What was yours like?"

    Jacob smiled and got a dreamy look on his face.

    "It was awesome, man," he said. "Jennifer Wu. She was a college freshman, and I was 15."

    "Wow," I said. I was impressed and secretly a little jealous. Part of me wondered how my first time might have been if I'd somehow managed to have that store clerk fuck me, or maybe someone else a little older.

    "Yeah, she had her own apartment and everything. She really knew what she was doing and made it super fun." He stepped even closer and spoke more softly, as if telling me a secret.

    "She even let me fuck her in the ass. I hadn't even thought about that but she was really into anal so she said we could do it. Man, all my friends were so jealous!"

    I noticed that Jacob was getting hard in his boxers as he thought about all this. Hearing him talk about it (and seeing his cock grow under that thin fabric) was making me hard as well, and I wished I'd put something on over the jockstrap. I didn't want him to notice, so I turned around and moved to refill my glass at the sink, even though I wasn't thirsty.

    "I guess that was nice," I said, turning on the faucet, "having someone really experienced who could show you all that." When Jacob replied I realized he'd come even closer, and he was standing right behind me.

    "You mean my brother's not an expert at fucking?" he said, laughing sarcastically. "Big surprise." I didn't know how to respond so I just took a sip of water. I was still hard and kept facing the sink.

    I suddenly felt Jacob's hand on my bare ass. He was rubbing one of the cheeks slowly. I felt him lean in and whisper close to my ear.

    "Maybe I should show you how it feels to be fucked by someone who knows what he's doing."

    I stopped breathing at that moment, not sure what to say in response. My cock was reacting though, to his words and to his hand on my butt. "Holy shit!" I thought. What is happening right now?!

    Probably sensing my tension, Jacob put both his hands on my shoulders and started massaging them lightly. For a moment I started to relax, but then I felt the hardness of his cotton-covered erection pushing against my ass.

    "What do you say?" he asked me more directly. "Can I show you?"

    "In your mom's room?" I replied, knowing already that I was going to say yes, but feeling like I needed to know what the plan was.

    One of Jacob's hands remained on my shoulder and I felt it grip me tighter. The other one moved down to my ass and I suddenly felt his fingers at my hole. It was still wet with lube, and probably a little of Noah's cum dripping out. I felt him rub his finger around for a second and then some of it slipped inside.

    "Feels like you're ready right now," Jacob whispered, and I felt his lips touch the edge of my ear. That did something to me and I let out a soft moan, just as his finger slid in deeper. For about a minute he slowly slid his finger in and out, never fully removing it, fingering me with his brother's cum as lube. As he was doing that, he also pushed up against one side of me and I could feel the hardness of his cock against my skin.

    I started to get a feeling through my whole body, it somehow felt like both relaxation and excitement. I braced myself using my arms on the edge of the sink and pushed backward, both into his crotch and onto his hand that was in my hole. I felt his knuckles against the back of my balls and I knew his finger was all the way inside. I could feel it moving around and the sensation was incredible. Noah had fingered my ass a bunch of times, but it was always just an in-out type motion. This was different. It seemed like Jacob really did know how to make it more pleasurable. I moaned again, a little louder and longer than before.

    I was really getting into it when he took his finger out fast. I was about to say something and then it was back in, along with another one. Another moan escaped my lips. Fuck, this was so... sexy. I hadn't felt like this with Noah earlier. Maybe this was so much hotter because it was unexpected. Or maybe it was because I thought of Noah mainly as a friend who I had fun with, but Jacob was just... older? Experienced? More manly? It all added up to something I couldn't name.

    His fingers withdrew from my ass again, leaving behind an empty feeling. I needed to fix that. I reached one of my hands behind me, without turning my head around. I found what I was looking for: Jacob's cock. He hadn't removed his boxers, he'd just put his dick and balls through the fly hole. I stroked his cock as much as I could with my arm twisted around behind me, and tried to guide it toward my hole. I wanted him inside me so badly.

    I felt Jacob's hand move to his cock to help guide it, and so I let go of it, returning to using both hands to hold myself upright as I leaned over the sink. His other arm wrapped around my body, right at the bottom of my ribs, and I felt the hair on his chest and stomach all along my back. Jacob's lips were right at my ear again.

    "You ready, baby?" he asked in a faint whisper. He called me "baby", I immediately thought to myself, and somehow that got me even more turned on.

    "Uh-huh," I replied, barely able to speak. And I felt the head of his cock push against my slick hole. There was a split second of intense pressure and then... he was inside. My legs suddenly felt weak; it was much more difficult doing this standing up, but his arm was around me and I let his strength support me. Jacob was still pushing in and I could hear him sighing softly as he kept going. Then he exhaled more sharply and I felt his waist pressing against the top of my ass. I had all of him in me.

    The hand that had been guiding his cock moved to my hip, the fingers slipping underneath the red waistband of the jockstrap. He used that hand to start guiding me into a very slow rhythm as he began to pull his cock out slightly and then push back into me. Earlier, Noah had started thrusting rapidly in and out, almost right away. That had felt good but this was ten times better. I was savoring every moment.

    "You doing okay?" Jacob whispered to me.

    "This is perfect," I replied, and I meant it. And just when I thought it couldn't get any better, his hand slid down from my lower chest, across my stomach and then onto the pouch of the jock. He didn't grip my cock exactly, it was more like his whole hand pushed against me and suddenly I was grinding into it. He'd push his cock into me and that would push me forward into his hand. Does he fuck girls this way? I found part of my brain wondering. Or anyone else?

    "Have you... unnh... have you done this with guys a lot?" I asked him as we continued our rhythm. At first he didn't say anything and in my semi-delirious state I wondered if I had said it out loud or not.

     "Actually," he finally answered, "you're my first." After he said that, he changed his grip on my pouch so that he just had my cock in his hand, and started stroking me slowly that way.

    I closed my eyes and felt myself smile. I'm his first, I thought. That's so cool! Jacob started moving a little faster, and I could feel him start to pull more of his cock out of me each time before he thrusted back in. His hand on my cock increased its pace at the same rate. The feeling of his chest hair between my shoulder blades suddenly gave me goosebumps, and the shiver from that flowed through my whole body. Both of us were starting to breathe more heavily, almost gasping. I noticed we were inhaling and exhaling right at the same time, over and over. In that moment, I felt connected to him in so many ways.

    These are the fireworks, I thought to myself.

    Suddenly I felt him inside me in a different way, somehow. Like a pressure that hadn't been there before. It was like a jolt deep within and suddenly I got that familiar feeling, and I knew I was about to cum. There hadn't been any buildup, it was just happening.

    "I'm gonna..." I started to say, but then the words vanished from my throat, replaced by a high-pitched groan of pleasure. My cock started to spasm and I felt the fabric of the jock becoming wet. Jacob was still stroking me, though more gently, and as my muscles tightened I heard him moan and start thrusting into me faster. As I finished cumming, Jacob's arm wrapped even tighter around me and he was pushing into me so hard that my feet started to come up off the floor. I kept myself in place with my arms. That intensity only lasted for a few seconds and then I felt his cock throb inside me over and over. He was filling my ass with his load, mixing it with the one his brother had left in there less than an hour before.

    "Oh my god..." I heard him say as he let out a breath, his words trailing off. I felt his forehead rest on the back of my head for a moment, an odd sensation. And then I felt his lips touch the back of my neck, staying there for a few perfect seconds of stillness, with him still fully inside me. Then we both exhaled more as he slowly moved backward and pulled out. I felt my ass moving backward with him, almost trying to keep him inside me longer, unwilling to let go. I crossed my arms on the edge of the counter and rested my head on them. I felt amazing, but totally exhausted.

    His cock wasn't inside me any longer but my hole still felt like it was open, and it made me jump a little when his hands lightly touched the inside of my ass cheeks.

    "Fuck," I heard him say quietly, as if in awe of something, and then I felt his finger at the edge of my hole. It triggered a reflex and I felt myself clench. I think it gripped the tip of his finger for a moment, and then his hands moved away.

    I stood up and turned around to look at him. I hadn't looked him in the eye since he'd been telling me about his own first time. He had the same smile on his face as when he had been talking about that girl. I realized I probably had a similar expression.

    He came in for a sort of bro-hug that lasted a little longer than those normally do. Then he turned around and walked back toward the dark living room.

    "Two brothers in one night, man," he said, laughing to himself a little. "That's a pretty fuckin' great story for your first time."

    I smiled to myself, silently agreeing with him and feeling pretty content. I headed back to Noah's room, ready to lie down next to him and get some sleep.

​

— The End —