Exploring Boundaries

I’m sure my face must have been one of disbelief, but I knew I was going to do this. I was horny, and I needed to do this. From the looks of it, we were going to do this. His dick was rock hard again already. Our dicks even seemed to throb in sync. I kicked off my sandals and peeled my t-shirt over my head. As I hooked my thumbs into the waistband of my shorts, I hesitated. I became self-conscious of the fact that I was facing Lucas directly and was about to expose myself to him—although it wasn’t like there was much left to the imagination at this point. Outside the locker room, where I always tried to be exposed for as short a time as possible, I hadn’t ever been totally naked in front of someone else since I couldn’t remember—before puberty, that’s for sure.

What the hell. He was naked and hard and already stroking again in front of me. I pulled my shorts down and let them fall around my ankles. My long, thick dick flopped out in front of me. I stepped out of the shorts and moved to my gaming chair. I pulled it away from the desk and turned it to face Lucas. I sat down opposite him and started stroking.

“Fuck, dude. We have twin penises,” he says before he lets out a moan.

“I noticed. When you were putting on that show for me,” I reply. “But yours is a supersized version of mine.”

“So seriously, man, what did you think when you walked in and saw me there gooning at porn?”

“Well my first thought was to get inside and close the door before anyone else walked by and got an eyeful.”

“Thanks man.”

“But then my eyes just bugged out. Here I was standing the same room with you while you were stroking your hard cock, and from the sounds of it, about to blow a load. I didn’t know what to do. I was afraid if I didn’t say anything until you were finished, you might be upset.”

He was focused on me as he continued stroking slowly and listening.

“So that’s when I decided to say your name. You didn’t even hear me the first time. I had to say it a second time louder, and I was afraid I might have to yell so loud that someone outside our room might hear me. That’s when you spun around, and you know the rest.”

“Thanks. It’s hot hearing all that. But what was all this making you think? What were you feeling?”

“Well we already know it made me hard and pre-cummy.” That made him smile.

“It made me wonder if you’re gay,” I continued. “When I realized how I was reacting, I wondered if I’m gay. But honestly, watching the way those first three ropes of cum shot out of your dick and hearing the sounds you were making, it made me wonder just how damned good it feels to have your hole played with.”

“Well there’s no time like the present to find out,” he says as he hands me a bottle of lube. “It feels a lot better with lube.”

I squirted a dollop on my middle finger and reached under my balls, touching my finger on my hole.

“You’ll need more than that when you’re ready to stick a finger in. But that’s good for just massaging your pucker.” He pauses. “I gotta admit. That’s kind of hot seeing you play with your hole like that.”

“Well I gotta admit that this feels a lot better than I would ever have thought.” I run the pad of my slickened middle finger over my pucker, steadily pushing a little more firmly, but still not penetrating. I started stroking myself with my other hand.

“Wait until you’re brave enough to get deeper in that hole and start touching your prostate. It’s amazing.” He reaches over and grabs the lube, making a pour gesture toward me. I give my hole a brief break as I bring my middle finger around for Lucas to christen it with more lube.

“Give me your pointer and ring fingers, too. Once you stick one in, you’re going to want more almost instantly,” he says. I give him a skeptical look. “Just trust me,” he adds.

I return my middle finger to my pucker, which I then circle several times as I sit there thinking how the fuck have I been masturbating all these years and never discovered this? Which makes me wonder what other discoveries lie ahead, so I begin pressing my middle finger against the very center of my hole. To my surprise, it pops in with little effort and despite having somewhat thickish fingers, it didn’t hurt. It actually felt amazingly good.

Lucas is watching as my finger penetrates for the first time. It didn’t hurt when it popped inside, but whatever that intensely pleasant feeling was, it made me gasp. Lucas was ready with instruction and more lube.

“Now that you’re in, lube up your sphincter. Just smear it around inside the opening,” he instructs. I do as I’m told and find that the smearing action engenders sexy good feelings of its own. “Here, let me give you some more lube.”

I reach back over for him to apply more and then return my slippery fingers to my ass. This time my middle finger goes right in. And feels fucking good. Just like Lucas predicted, I’m ready to try another. I try to insert my pointer finger, but the hole is definitely tighter with my middle finger already in. It feels good to probe at my hole with my pointer with my other finger inside me. I start sliding it in and out, short strokes.

On one in-stroke, my pointer finger slides in, too, opening me wider and again I gasp. I stop moving my fingers for a moment and just lie there, taking in the delicious new feeling of having two of my fingers inside my asshole. I move them around a little, trying to stretch myself open more, the way that I had fantasized about doing to a girl someday.

“Find your prostate, man. Rub your middle finger over it by curling your finger back toward your hand, like you’re motioning someone to come over. Your prostate is a few inches up inside.”

I try but nothing.

“You’re probably not just deep enough. Try again, deeper,” Lucas suggests.

I try to slide my fingers a little deeper, and this time I definitely feel something pleasurable, but it is very brief. It felt like the very tip of my finger brushed over something that was firmer but just barely within reach of the tip of my middle finger. If I need to get my middle finger any deeper, I think I might have to insert more fingers, and I’m pretty sure I’m not ready for my whole hand.

Lucas lets out a sigh. “Honestly, I started out with someone else doing it to me, and I’m sure that made it easier for me to find when I first started fingering myself.” His comment lingers suggestively in the air. Neither of us says anything. What he said was ambiguous. I’m thinking, Is he suggesting that he finger my ass for me?

This time I’m the one who breaks the silence. “Well this feels really good. I can see how someone else doing it for you might feel even better.” If he was being suggestive, I’ve just now given him something of a green light. If he wasn’t being suggestive, my comment can be interpreted in the same non-suggestive way. The truth was I desperately wanted to see how it would feel to have someone else touch my prostate, and at the moment, Lucas was the someone else most likely to do it.

Lucas just keeps stroking, and I realize I’m focused on his hand gliding up and down his huge shaft, his big balls bouncing up and down as they slowly creep closer to the base of his cock. I can’t believe how it’s turning me on. I look at his face and see he’s staring at me stroking like he’s entranced.

I let go of my dick and scooch down and forward in my chair so that my ass is now partially hanging off the seat. I pull my legs up and back and hang them over the arms of my chair. Then I reach with both hands under my thigh to grab my ass cheeks and spread them, exposing my now very horny hole to Lucas. I don’t know what’s gotten into me, other than I’m the horniest I’ve ever been in my life. Staring at him, I search his face for some reaction to my attempt to dare him into showing me what it’s like to have your prostate fingered.

He gets it. “Is this your way of telling me you want me to show you how it feels for someone else to do it to you?” he asks. I nod. He looks up at the ceiling and lets out a sigh. I make a mental note to ask him later what that was about.

Then he lubes up his fingers. He wastes no time, and I gasp when he first penetrates me with his thick middle finger, just like I did when I first stuck mine in. He immediately stops moving his finger to give me a moment to adjust to this new, invasive, but admittedly pleasurable feeling.

“Okay,” I say. “Keep going.” He begins gently pumping his finger, and I don’t know what else he was doing, but it felt better than anything I’d ever felt before. The way he was moving his finger was stretching my hole, too, and that was amazing.

 Lucas finds what he’s looking for. “There it is. Right there,” he says, and I simultaneously feel his finger probe an insanely exquisite spot. He obviously found my prostate, and he’s right: I won’t ever have any trouble knowing whether I’ve found it again or not. That feeling as his finger brushes against my prostate is fucking incredible. As good as fingering my own hole was, this was most definitely better—way better! I don’t know if it’s the angle or what, but his finger is clearly rubbing my entire prostate, not barely brushing it the way it felt when I was trying to finger myself.

Lucas works in another finger, maybe two, I’m not sure. He continues massaging my prostate as I stroke. He’s stroking his own dick with one hand while he fingers me, and I cannot resisting watching his fist glide up and down his shaft. I glance away only to check out his face, which is mostly expressionless. He’s focused on either watching me stroke or his own fingers fucking my ass. I can’t really tell which, though he’s probably watching both.

After several minutes of this intense pleasure, as Lucas continues fingering my prostate, I begin to feel that familiar sensation as my orgasm starts to build. Only this is more intense than ever before. And faster.

“Oh yeah, your balls are tightening up man,” Lucas says to me. “Getting’ close?”

I nod. He’s on his knees in front of me. He let’s go of his own dick which continues to bob around, precum oozing out of the slit. He grabs my balls in his free hand, tugging gently on them and massaging them as he continues fingerfucking me.

I shoot a load that hits me in the forehead, streaks across the side of my nose, and drips over the middle of my lips. A second volley hits my chin and dribbles onto my chest. At about the same spot, a third rope hits my upper chest. I am nearly in a convulsive state as my cock continues its outpouring, producing more sperm than I have ever shot in my life. Lucas watches me intently as my body and dick jerk in sync with one final orgasmic spasm. He stops fingering, but he keeps them in me, still. After a few moments, I sigh and begin to revive from my position of surrender. Only then does Lucas withdraw his fingers slowly, making me shiver. My ass feels weirdly empty.

Then he grins at me. “Did I lie?” he asks.

I smile back as I consider my reply. After a moment of thought, I lick the cum off my lips the way he had earlier. I give him a mischievous smile. “If that makes you gay, then I guess we’re both flaming homos!”

I could tell by the look on his face that that was definitely not the response he was looking for. He was looking for reassurance that we’re not gay. So he growls but then playfully shouts, “No! That’s my point! We both like girls, but we also like butt play. Not all butt play is gay!”

“True!” I reply. Now Lucas seems less okay with the fact that we might not be entirely straight. And that made me want to reassure him. To reassure us. But at the same time, I was thinking, Okay, maybe not all butt play is gay. But what about when your guy friend is fingering your prostate, both of you are naked, and you’re jacking off? Gay or not gay?

Lucas returns to his chair and assumes the position that I’m still in: ass hanging off the seat, legs hanging over the chair arms, both hands spreading his cheeks and exposing his hole to me. “Return the favor?” he asks.

There we sit facing each other, our holes exposed to each other, and my roomie is asking me to finger his asshole. And it’s hot as fuck! This day has certainly taken a turn I could never have predicted. Now I can appreciate why Lucas is asking me to finger him. I fully appreciate it in a way that I never could have less than an hour earlier. At the same time I’m thinking sarcastically, Yeah, this isn’t gay at all. Right. But I’m also caring less whether it’s gay or not because it feels so fucking good.

I let my legs down from the chair arms and stand up. I grab Lucas’s cumrag and wipe the cum off my face, leaving the cum from my chest down to my balls. I bend over to take a closer look at Lucas’s ass. I hadn’t gotten a very good look at his actual hole before. Hell, I didn’t even realize at the time that it would be of interest. Now with a front row view, I can see that his isn’t really different than the countless female assholes I’ve seen in porn, aside from being hairier. I had shot liters of cum imagining playing with assholes. They just all happened to be female assholes in those fantasies. Here for the first time, however, was an asshole literally begging for my attention. And even though I’d just had what was probably the best orgasm of my life, I was still horny as fuck. Plus, I figured fingerfucking Lucas was less gay than being fingerfucked by Lucas. So gay or not, I was giving in to this temptation.

I pick up the lube, squirt some on a finger, and dab it on and just inside Lucas’s hole. His dick is already at full mast, bobbing above his belly, a strand of precum extending from his slit to his abs.

“Fuck! That really does feel so much better when someone else is doing it,” Lucas says. I apply more lube, and his hole easily takes two of my fingers. I start searching for his prostate with the curled finger motion, and I feel something firmer than the surrounding soft flesh. Lucas grunts, so I flick my finger across it again.

He jerks slightly again. “That’s it. You found it.”

I feel a proud sense of accomplishment, immediately followed by the thought, Yeah, real proud, dude. Proud of fingerfucking your buddy’s ass. Nice! The first few of those homophobic thoughts had made me felt a brief twinge of shame or guilt. Now it just made me hornier.

Lucas is moaning, and the sight before me is even hotter than before. Here he was stroking his big dick in front of me again, but I am so much physically closer this time. Closer almost isn’t the word since I literally have two of my fingers in him. I’m still standing awkwardly above him, so I shift to a kneeling position to be more comfortable. At this point, his dick is practically in my face. I can smell that musky guy smell, reminiscent of a men’s locker room. Like earlier, I’m thinking, I could touch his cock if I wanted to. And for the second time, that’s exactly what I want to do. I’m still too timid to go further on my own, so I resist the urge. Instead, I apply more lube to my fingers, reinsert them, and start to work in a third.

This time when I add a finger, he sucks in air through his teeth. “Easy,” he says. I wait for a signal from him to continue. “Okay, go again. But this time, try pumping your fingers but keep flicking my prostate with each thrust.”

I do as instructed. I kind of get it already because it’s what he was doing to me. And so there I am with three of my fingers pumping in and out of my roommate’s ass as he strokes his dick. I could swear his cock looks like it’s swelled up even more, if that’s possible, and I notice his balls are beginning to pull up tight.

“Oh my god that feels so motherfucking good, man!” Lucas is lost in the pleasure. Precum is flowing over his fingers as he strokes. His balls pull so tight they disappear inside him.

Then he surprises me with another instruction: “Oh fuck, oh fuck, oh fuck. Lick my balls, man. Lick my balls!”

At this point, I’m using my free hand to stroke my own dick, which had already come back to life (another first). Although the rest of me freezes, I don’t stop pumping his ass with my fingers. But I’m wondering does he really mean that? Then I’m thinking how if I did it, I’d not only get a really good whiff of his musky junk, I’d get a taste, too. That is immediately followed by the realization that I can’t even see his balls anymore. They’re drawn up inside him.

The few seconds it takes for these thoughts to run through my mind are all it takes to bring him to the brink. Before I could decide whether I was going to lick anything for him, another eruption followed.

Lucas’s second load was even more impressive than his first. The first shot was like mine, to the forehead, down across the lips and dripping off his chin. This time he starts licking manically as soon as the cum was on his lips, and his second shot delivered cum right on his tongue. He deposited another couple of volleys on his abs, and his dick amazingly kept oozing out more pulses of cum.

When his orgasm completely subsided, he let out a deep breath and asked me not to pull out just yet, so I remained motionless while he recovered, like he had for me. If I hadn’t witnessed both his orgasms firsthand, I would never have believed that a guy could shoot so much cum and shoot so much cum twice within a few minutes!

As I knelt there with three fingers in Lucas’s ass, I tried to absorb everything that had just happened: I walk in and find my roomie masturbating to penis porn while he fingerfucks himself to an explosive orgasm. Then I strip down, start stroking my dick while I fingerfuck myself under his instruction. He takes over and fingerfucks me while I stroke my dick until I have my own explosive orgasm. And then I “return the favor,” as he put it. No. This day had definitely not gone as planned. But it has been a fantastic day.

After a few moments of silence, Lucas asks me to start pumping my fingers again.

“You want more?” I ask, surprised that he’s already ready for more.

“You do,” he says, gesturing to my crotch. I look down. I’m fully engorged. I look back at him. He gives me a devilish smile. “Or at least your dick does.” The physical evidence that I want more is undeniable.