Xander Shows Me My Prostate

"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 un-spooked 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 for 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 breath. 
 
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 kinda 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. 

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This is the first part of an ongoing story, and you can find more of my writing at www.alexpendragon.com