Xander Shows Me My Prostate: Xander Shows Me My Prostate, #1

Chapter One

srsly try it dude

I shook my head at Dan's text, though I couldn't help but grin.

ur a freak I punched back.

sure ;) but u no u want to try

Dan had been on at me for days, telling me about how he stuck his finger up his ass while he was jerking off one time and that it was the best fucking thing he's ever felt. At the time I told him it'd be different if he had a girl who'd give him head and fuck him, but then neither of us is having much luck in that department right now. 

So, instead he says he was checking out this sex messageboard online and found all this shit about how whacking off with a finger up your ass feels, like, ten times better. And Dan's a freak, like I told him, and so was bound to try it. Supposedly he's been doing it twice a day, every day, for three weeks now, though he only started pestering me to try it myself last weekend.

Don't get me wrong, I mean I understand that some people like putting things up their butt. Gay guys, for instance, and while I'm not gay I don't have an issue with it. I'd just rather be the one putting my dick up some girl's ass if there's gonna be ass involved, y'know?

But Dan's persuasive, and there's no girl who'll even let me get near kissing her, never mind fucking her, and he got me wondering what all this ass stuff might feel like. 

And that's why, now that my parents and my big sister are out of the house for the afternoon, I'm down to my boxers in the bathroom wondering how, exactly, the logistics of the whole thing are supposed to work. I guess I'm not really all that ass-aware: it's just there, it does its thing, and it gets washed in the shower with the rest of me. So far it's all been one-way, though.

Dan's got this lube that he found in his brother's nightstand after he went to college, and he hardly stops talking about how it makes the classic fapfapfap sound when he's beating his meat. There's not much that looks like it would do that in our bathroom cabinet, though; the closest I think I'm gonna get is my mom's lotion.

I pump a few squirts into my right hand, squeeze my fingers around to get them all slick, and then realize there's no way I'm going to get my hand in my boxers without getting them all greasy. So I try to tug them down with my left hand, and by the time I've done that I'm starting to feel a bit stupid. 

First try and I'm getting more lotion down my ass crack than anywhere else, so I put one foot up on the toilet seat. With my back to the mirror I can see my butt cheeks spreading, enough for me to dip my finger in-between and just prod at my hole a little. 

It feels... tight. Like, no-entry tight. I push a bit more, and my ass starts to dimple under the pressure, but it's not exactly letting my finger in and I'm nowhere near feeling turned on by it. If I didn't have a fistful of make-do lube I'd be texting Dan and calling him a fucking liar right about now. 

Then again, Dan said he did it laying down, on his back, so maybe that's where I'm going wrong. I grab a towel from the rail and go back to my room, glad that the house is empty so that I don't need to worry about running into my mom with my junk all hanging out. Yeah, she used to bathe me when I was little, but I don't think she needs to see how my dick grew up, right?

If I thought getting my boxers down with one hand was tricky, getting the towel spread out on the floor is even harder. This had better be good, else I'm gonna give Dan some serious shit when I see him next. 

Lying on my back, with my legs apart, I can reach down between my thighs and poke around my hole. It does feel different to before - softer, somehow, less tensed up - and if I press my fingertip in I can feel it starting to give. It's feeling pretty good even without my finger going in there, and my dick is starting to chub up too.

I'm not gonna lie and say I've got some porn-star scale massive cock, but it's big enough I guess and it does what it's supposed to: keep me occupied before bed and, hopefully, eventually, get inside some girl. It's lengthening across my pelvis as I trace the tip of my index finger around my ass, my balls pressed up against my wrist as I dig around in my crack.

I reckon I could probably get off like this, but I want to see what Dan's talking about, so I push some more. It takes a few seconds, and it feels crazy-weird initially, but I've got the first half-inch or so inside eventually. My ring is clamped down tight around my finger, and it's a little uncomfortable, but at the same time I don't really want to take it out. 

Super-gently, still half worried I'm gonna damage myself somehow, I push a bit harder and ease some more finger inside myself. It's hot, and feels really slick, but that could just be the lotion I'm using. Not so much uncomfortable any more, just... unusual. 

I'm so focused on the feelings swimming out from my ass that I don't realize at first how my cock has gone major-boner hard all of a sudden. I wrap my left hand around it and give it a squeeze, and my butt clamps down in sympathy on my finger.

I couldn't hold the gasp in, the feeling was so intense. I give my cock another couple of slow strokes, really more milking it from root to tip, and my hole starts pulsing and fluttering. There's a big, glossy bead of precum starting to ooze out of the tip; I'm not a big drooler usually, but I seem to have opened up the floodgates somehow. 

Eventually I'm pushing my finger inside in time with yanking on my dick, and soon I'm going all the way in, right down to the knuckle. It feels weird and brilliant and I'm having to stop my other hand from speeding up to a blur and blasting goo in, like, twenty seconds flat. 

I've got my head pressed back against the floor and my finger punching up deep inside my hole when things go wrong. First I know about just how wrong is a voice from the door.

Whoa, dude.

My head snaps up, and the rest of me freezes. It's not my parents, thank fuck, but it is my big sister's friend Xander, and he's stood in the doorway kinda gaping at me in surprise.

Now, I've gotta tell you something about my sister's friends. She's this total lesbian, and seems to have found all the weird alternative people in our town and gathered them all up. Most of them are major douchefucks - the sort of people who think they're really cool and have ironic meme tattoos like that three wolf moon picture but with the Kardashian sisters' heads all howling - but Xander is probably the main exception. He's a really great guy, and I always enjoy hanging out with him when he comes over to see my big sis, and he never makes a deal out of the four or five years difference between us. 

So I'm more than a little mortified that he's found me spread out on my back, legs apart and a finger up my ass, jerking off. My mouth has fallen open, and the only thing I can think to say is dude, I'm not gay. Then feel dumb about it, because it's not like he doesn't have gay friends, but still. This has to look majorly sus.

He grins, kinda shrugs and tells me hey, no harm no foul, sorry for walking in on you.

I shake my head a couple times, the rest of me still frozen with my hand wrapped around my boner and my finger pushed just about all the way up inside my hole. 

Seriously, I'm not like some weird closeted dude, Xander I start insisting. I'm just...

He holds his hands up in kind of a 'slow down' way. Look, dude, you're not gay, I get it. You're just having some fun.

I watch his face to see if he's laughing at me, which would be totally out of character for Xander but then again this is a pretty out of character situation for us to be in. He doesn't seem to be, though. 

Seriously, buddy, a guy's ass is fair game is all I'm saying he tells me, grinning again. Lucy loves to tip me over the edge with a sly finger in my hole when we're fucking.

Xander's got this awesome, super-hot girlfriend called Lucy. Not conventionally gorgeous, like a model or something, but just wicked-fine in her own way. The thought of Xander pounding between her legs, and Lucy sliding a finger up his ass while he does it gets my cock jerking and pulsing again, and it's all I can do to stop myself from automatically stroking it.

Yeah, a bit of prostate action is awesome he's saying, and I'm frowning at that. He looks at me, what I guess must be obvious confusion. Dude, your prostate.

I kinda shake my head.

The bump in your ass that makes the fireworks go off.

I'm seriously not getting it. Dan told me to put a finger up there and jerk off, and that's what I'm doing, and while it feels great in a sort of this is new way it's hardly fireworks. 

Xander takes a step into the room. He's wearing these semi-baggy denim cargo pants, the kind with plenty of pockets, and a ribbed white wife beater shirt, and I can see the crazy cool half-sleeve tattoo he has snaking up his arm and over his shoulder. Like I said, some of my sister's friends are so try-hard it's painful, they look like they've dive-bombed a piercing store and left with anything that's stuck, but Xander just has a medium gage in one ear and a tiny bolt thing through his eyebrow.

Look, bud, if you're not getting fireworks you're not doing it right Xander tells me, and I kinda have a half-secretive attempt at an explore - y'know, trying to feel around inside myself without making it look like I'm probing up my ass with another guy in the room - to see if I can figure out what he's talking about, but I can't.

He shakes his head, grins. You've got the angle wrong, dude. 

I'm beginning to get pissed off at the whole situation, like Dan set me up to make a fool of myself in the first place. There's still a part of me that's kinda surprised at how relatively unspooked I am that Xander is seeing me naked and jackin' off. Usually I avoid times and places where other people might even see me undressed, like in the locker room at school. 

Look... he pauses, like he's thinking about something hard. You want me to help you out, dude?

We stare at each other for a moment. I guess he's asking me if I want him to help me jerk off, which would be a total new element to whatever friendship-by-proxy we've got going on by virtue of him being in my sister's clique. I know I should say no, and pull my finger out, or maybe, y'know, just ask him to leave so I can whack off like a normal guy and put all this behind me, but I don't. In fact I give this little half-nod, and that seems to be all it takes. 

Xander walks over, and drops to a crouch in front of me, just ahead of my legs where they're pulled up. 

This isn't weird shit, okay? Don't get stressed out over labels and shit like that, he tells me.

He's not warning me - like, insisting he's not gay himself, and that I'd better not dare assume differently - but it's like he doesn't want me to freak out. And I'm not freaked, not really; my cock still hasn't gone soft, after all. 

So dude, look, it's all about the angle, Xander says, and he takes my right wrist and pulls my finger free.

All of a sudden it hits me that he's got a perfect 20/20 view of my ass, cock, and balls, and I can feel myself starting to blush. 

Um, dude... I start, and he shakes his head at me. 

Don't freak out, okay? We make eye-contact for a second, and he slowly nods, just a little. Nothing to be ashamed of with this equipment, my friend. He's grinning at me, and I can't not grin back at the compliment.

Xander reaches out his hand and kinda hooks his forefinger across the head of my cock, until it's glistening with precum. I'm holding my breath as he does it, totally unable to move. Then I can feel his fingertip pressing where my own hand was just before, and my slick, lotioned-up ass just lets him inside, and before I know it he's got his whole finger in me.

I gasp, and my dick burps up another big gob of goo that slowly oozes down and around my fist. Xander's looking down, I guess to where his finger is pushed, with this look of intense concentration on his face. 

So bud, he starts, still not looking up at me.

I can't help it, I start to gently frig my cock, as slowly and hopefully unnoticeably as possible, the feeling of him in there is so strange but I don't want him to take it out again any time soon.

You need to hook your finger forward until you find the bump, that's your prostate.

I can feel him exploring in there, twisting his finger where I'd just been jamming it in and out. It's pretty much more of the same, though, until bam, suddenly I feel like I've stepped on a live wire.

My legs jolt out, and I accidentally hump my butt down onto Xander's hand and almost send him toppling backwards. He chuckles and kneels down properly, as I grip my dick with a super-hard hold just to stop it from blasting off over my head and getting stuff on the ceiling, the feeling is that good.

You want some more? He asks me, and I nod like a dog, desperate to feel that sensation again. He's got this huge grin on his face, but I don't care if he's laughing at me because his finger is jabbing at that place inside and I'm seeing stars. Soon, I'm frantically beating off as he pokes and strokes up inside my ass, feeling my balls churn like they want to shoot up out of my cock along with my load. 

Dude, this is totally hot I hear Xander say, and when I look down he's rubbing the front of his jeans with his other hand. I can see they're tented out with his dick, and after a minute or two of palming the length of it through the fabric, he tugs open the button fly and half pulls them down his thighs. 

Underneath he's got these black Armani briefs on, with a big thick slab running up the side of his hip. I glance up at his face and he winks at me, then tickles his fingertip across that magic bump so that I bang my head back and momentarily lose the ability to breathe.

When I look down again, he's tucked the waistband of his briefs under his balls, and his cock is hanging out, way thicker and longer than mine. His pubes are closely cropped down and it makes him look even bigger still, some part of my brain taking note and deciding I need to try that myself. Y'know, when I'm not flat on my back and having some guy finger my ass. Xander's left hand is kinda tugging on his dick, but he's giving most of his attention to what is going on with my hole. 

Dude, you're not gonna... y'know... I say to him, suddenly apprehensive, and he shakes his head. 

Don't worry bud, just letting some tension out myself, yeah? 

I nod, and he keeps gliding across my prostate while he fists his dick, kneeling so far up close to me that sometimes I can feel the slick head of his cock brush against my thigh. 

You reckon you could take another? he asks, and while I'm trying to figure out what he means I feel his finger suddenly pull free and then, almost instantly afterwards, the sensation of my ass being stretched even more. Two fingers, dude, he laughs, and I'm about to say something when he hooks both of them up and really grinds against my button.

That's all it takes to push me over. My hand is a blur on my dick now, other hand gripping my balls to stop them from rocketing up inside my groin, they're pulled so tight. The first blast of cum clears my head, and I can hear it spatter wetly on the towel behind me. The next few shots land across my cheek and my chest, and I'm gasping and puffing as I try to process all the sensations. 

Oh god dude, that's so hot, I hear Xander mutter, and then I feel his cum land on me, heavy lashes of it against my thighs and across my balls. He's groaning, still pumping his fingers in and out of my twitching hole. 

We sit there for a while, deep breathing all round, as we gradually come down from the high. Xander gently pulls both his fingers out of my ass, and rubs his palm in all of the cum - his cum - that's across my groin. It should feel fucked up but it doesn't, not at the moment anyway. 

So that's your prostate, he tells me, smiling, and I look down to where his cock is bobbing gently, a little deflated but still hanging horizontally out from his flat groin. Lucy must really feel that when it's in her, I suddenly think out of nowhere. Not that it feels like something I can really ask him about, even after what just happened.

Thanks... I mean... I start to say, and he nods, already understanding. 

No worries. But dude, damn, it smells like fuckin' cum city in here, you might want to take a shower. I grin sheepishly, as he tucks his dick back into his briefs and then wipes his fingers on the towel. We make eye contact again, and that smile of his is back. Glad I could help you out, buddy.

Now I'm wondering if maybe Dan isn't the only freak around.

Chapter Two

I was embarrassed as fuck, and also couldn't stop getting hard thinking about it, and that was a pretty fucking difficult mix of things when you throw in the fact that I literally couldn't stop thinking about it. My brain would be caught up in a movie, or food, or whatever bullshit chores my mom and dad were making me do, and then bam, suddenly I'm thinking about how incredible it felt when Xander's fingers nudged across that panic button in my ass, and I'm blushing and boned up all at the same time.

I say panic button because that's how I was starting to think about it: the super-sensitive spot inside me that was gradually making me go nuts.

There was no way I could wear the usual boxer shorts any more, they were zero fucking use at hiding my dick when it reacted. I ended up pulling on the compression shorts I had for football at school, just because they were tight enough to keep things at least a little bit subtle down there. Rather than, y'know, my hard cock just wagging around in my sweats 50% of the time.

Problem was, the way they clung to my dick just ended up reminding me of Xander's erection, and the way it'd bulged in his briefs. Not that I was getting off on thinking about how hard he'd been, but fuck, the guy was fit and while I usually would've said briefs were kinda dorky, on him they looked pretty amazing.

Made me wonder if Lucy liked him wearing them. Definitely a lot sexier than my baggy plaid boxers, even I could tell that.

Maybe it would've been better if I'd just been jerking off morning and night, my fingers hunting down that nub inside me that Xander had located. My buddy Dan, the kinky freak that had got me into trying all this ass stuff in the first place after he read about it on some dirty messageboard, had told me that after he realized how it felt he'd been shoving his fingers up there twice a day for weeks. He gets addicted to this shit pretty easy.

I'd liked how it felt - okay, that was an understatement - but, even though my body had clearly enjoyed the idea, I hadn't tried it again. It'd been three days since I'd blown my load all over myself as Xander pumped his fingers into my hole and then bust all over my crotch, and I had to admit I was a little bit worried about just how much I was thinking about it, and how doing it again seemed so incredibly tempting.

That sort of thinking led you down the path to freaky-Dan territory.

I couldn't be completely sure that if I started jerking off that wouldn't automatically end up with me playing with my hole again. It was kinda wild to me that I'd gone for, like, eighteen years without ever thinking about my ass as something other than boring and functional. Now, just the idea of pulling on my dick had my brain instinctively jumping ahead to how it would be so much better if I was rubbing my prostate at the same time.

Fuck Dan, and fuck Xander too. Fuck them both for screwing me up like this.

I'd gone from jacking it twice a day to basically three days of cold turkey, and fuck, my body wasn't happy with it. It wasn't like I was some sort of sex addict - I mean, shit, it wasn't like I was getting any of that regularly from girls, either - but if I didn't cum first thing and then right before bed it was just a given that my brain would struggle to focus right. That's what happens to guys, y'know?

Three days without cumming and my mind was in meltdown.

I was starting to do embarrassing shit, like touching myself when I shouldn't, or even dry humping without realizing it. Watching TV or playing some video game, and finding I was grinding the controller or the remote against my dick through my jeans, maybe. I knew it'd gone too far when I was making a sandwich and ended up rubbing myself against the edge of the kitchen counter while I was doing it. My body just desperate for some sort of friction.

What was really messing up my brain, though, was that while I wanted to say it was all about how amazing it'd been to cum that way, if I was being honest it wasn't just those physical sensations. The fact that it'd taken Xander helping to get off so incredibly, well, that mental picture kept surging back into my head. Even the shock at him walking in and finding me on my back with a finger shoved inside me had twisted, somehow. Less embarrassing - though yeah, it was still pretty fucking embarrassing - and more like a naughty thrill or something.

The fact he hadn't freaked out, or reacted badly, or called me a dirty pervert still blew my mind. Almost as much as the way he'd shown me how to finger myself right, even. I mean, sure, Dan and I talked about kinky stuff sometimes, but there were limits; I wasn't gonna just sit there in the room with him while he tugged on his dick and played with his hole.

Even if now there was some side part of my brain wondering whether Dan did it to himself the same way Xander had to me.

I would've thought Xander's reaction would be shock, or disgust, or maybe feeling embarrassed for me. Honestly, most of my big sister's friends were such try-hard weirdos, I'd be worried if they actually did like me.

Xander, though... it would've sucked if he'd decided I was gross or something. Not that we were friends, not really, but we were definitely friendly. The idea of that ending made something in my chest feel all twisted and sickly, even if I couldn't put a name to it, exactly.

He'd not said anything negative, though. In fact he'd been totally the opposite of judgmental, and just got to work showing me what I was missing. Looking back on it, I still can't quite believe that he fingered me while I jerked off, and that he jerked off too while he did it, but at the time it seemed... okay, not normal, but not crazy either.

It didn't stop me worrying about what he might be like when I next saw him, something I found I wanted but at the same time didn't want, too. Like, the memory of how he'd been might end up being better than the reality of running into him, if Xander had started regretting what'd gone down. Not that I got the impression that he would, not at the time, but then again you can't really predict shit like that.

So I was kinda excited and really nervous when I get home and hear my sister and a load of other voices in the kitchen. Nothing I can make out specifically, just a group of people all talking over the top of each other. Part of me wants to just go straight upstairs, bypass the whole scene, even though I did want to grab a drink from the refrigerator. But there's another voice in my brain saying that if I go in, Xander might be there, and seeing him would be pretty cool.

My legs are carrying me down the hallway before my brain has a chance to decide either way.

My sister's group is all friendly enough, even if they're try-hards, so I get plenty of head nods and what's ups as I walk through the kitchen. Trying to make it look like I'm feeling casual and all, rather than giving in to what I really wanted to do and look around eagerly to see if he was there.

Just stare at the refrigerator and focus, I tell myself. Go straight there, try to look casual, grab your fucking soda, and then walk out again. If you're feeling stressed, that's just because of the blue balls.

I pull open the door and grab a cold can; swing it closed behind me. Turn, to find myself facing Xander right across the kitchen island.

He's grinning at me. I blink back, feeling a dumb sort of shock even though it's hardly a surprise that he might be here.

Hey, dude.

I swallow, my nod back at him jerky and kinda forced. He's wearing this white t-shirt with the sleeves ripped off, as though he'd just torn at it until it was close to being a wife beater. Perfect for showing off his half-sleeve tattoo as it sort of winds up and across his shoulder.

Uh, hey, I manage to say, finally. Trying to figure out if my voice was all pitchy and squeaky, like I was still going through puberty or something, or if that was just my ears ringing from the surprise still.

Hey Luka.

Another blink, my head snapping around a few degrees like I'd got caught staring at him too long. His girlfriend, Lucy, was stood next to him, giving me a friendly grin. I had to swallow a couple of times before I could bring myself to respond.

Oh, uh... hi Lucy.

Like I said, Lucy is really fucking hot. Not in a conventional, pretty-girl way, but sort of serious and strong, somehow. Like, you could imagine her being a warrior or something, which sounds stupid but there's just this totally non-feminine energy there, even though she's got great tits and all.

The way they're both smiling at me is making me nervous. I didn't think Xander would've said anything about what he and I had done, would've felt the need to tell her, but then again we'd not discussed keeping it a secret either. It was totally possible that they had the sort of relationship where shit like that happens, but it's okay just as long as both the people are upfront about it too.

Which could mean that Lucy was standing there, staring at me, with the full knowledge that her boyfriend had pushed two of his fingers into my ass while I jerked off desperately. I'm not exactly sure how I feel about that idea.

Well, no, my brain isn't sure. My dick is twitching in my compression