Weekends With Wes #1 - Your Virginal Visit

Author's Note: The stories in this series were written for one specific commissioner, who's been a fan of my stories for a long time, who most know as Moo Pup Cruze. I'm posting them here with their permission, but probably won't post them wider than this. The stories are a bit extreme at times, so consider yourself warned.

***

You’re excited to spend the weekend with me, aren’t you? Hot fella like you, hot fella like me, there’s a lot of fun stuff that the two of us can get up to for a couple of days. You arrive on Saturday morning and we make some small talk. For the last few weeks, perhaps out of a slight nervousness, you’d been sharing some of your previous, sexual exploits. It had been out of a desire to come off as experienced and prepared, but even now, you worried that, perhaps, it had made you seem like a bit of a braggart, or perhaps even worse than that, like you were much too eager to shore up your own bonafides, and were oversharing from a place of insecurity.

As we were chatting and smoking our cigars together, I started asking you about one of the tales you’d regaled me with in particular. In this story, you’d told me about two daddies that you’d serviced at the same time, starting at their feet, working their way up to their cocks while they smoked cigars and made out with each other. Eventually, you’d ended up spit roasted by both of them, one pumping a load in your ass, the other shooting all over your face and beard. You confirmed it, adding a few key details. One of the bears had been heavyset with a bushy white beard, wearing flannel and jeans. The other had been more muscular, wearing a leather harness and vest, with a bigger cock. It had apparently felt great in your hole. I just smiled, then I told you that there was something that I wanted to show you.

You followed me into my little office, where my computer was booted up, the screen black. I had you sit down in the chair in front of the computer, and I wiggled the mouse. You realized that the black screen was actually a paused movie, ready to play. I clicked the middle of the screen, and after a few moments, the intro scene to a porn flick started to play. You looked up at me, confused, and asked why were we watching porn, and I just shushed you, and fast forwarded a bit to the second scene of the movie, which featured just the sort of scenario you had just laid out for me in such vivid detail.

Two daddies, one older, dressed in flannel and denim, the other in leather with a bigger cock, sitting on a couch, smoking cigars, while a young cub licked their feet clean. Together, we watched for a few minutes, as the cub worked his way up to the men’s cocks and started sucking on one, and then the other. “So, is that you?” I ask, “It doesn’t look like you. He’s quite a bit hotter than you are, in all honesty.”

“Look, so it’s similar to what I described, I never said it was unique,” you say, feeling a bit defensive.

“Don’t play me for a fool,” I say, “It’s exactly the fucking same, every little detail you made sure to tell me, it’s right fucking there.”

It’s just a fucking coincidence.”

“Yeah? How about the rest of these, they all coincidences too?” I ask, minimize the porno, and there’s a file folder with at least twenty other movies in it. “Because all of these videos have two things in common. First, they all have a scene it them with that handsome cub from the first one, and two, you’ve described all of them to me, in perfect detail, as your own sexual fucking exploits.”

“That’s, I mean...That’s ridiculous,” you say, but even you can hear the doubt creep in, the confusion. This isn’t how this was supposed to go. This wasn’t supposed to be happening.

I open up another video, and fast forward. “I think this was what you described as your first flogging, right? You were strung up against a St. Andrew’s cross, back out, while a big muscle bull redded that back of yours, before moving onto paddling your ass, and fucking you right there against the cross. That was what you said, right?”

“Yeah, but again, it’s not--”

“And here’s this one, where you worshiped that guy’s musk, the construction worker, right? Licked him from head to toe, then he’d sat down on a rim chair and let you service his hole while you jacked off, and he finished by standing up, shooting all over your face, and then pissing on you through the rim chair.” I skipped around the video to each little detail, letting it play out in front of you, the same story you were so certain had happened to you, suddenly thrown into doubt.

“That’s not the most insulting thing, you know,” I said, “It’s the fucking theft. You even used the guy’s photos on your profile. Did you think that when you showed up, I wasn’t going to notice that you looked so fucking different?”

I had my phone up now, showing you your profile, your picture. A picture of you. Stammering, not sure what you’re even trying to explain or justify, I grab you by the collar of your shirt, pull you up to your feet, and drag you into the bathroom, plant you in front of the mirror. “So what the fuck is it. Are you fucking delusional, or are you just a fucking liar?” I hold the phone up next to you, so we can both compare your reflection to the photo ripped from your profile, and you realize, with a sinking feeling, that it isn’t you. You aren’t the guy in the photo. You look similar, maybe. Like a much less attractive older brother, perhaps. He’s muscled, and you have some muscle, a bit, but mostly you’ve gone to seed with a soft gut, not nearly as hairy as the fellow in the photo. Your beard is patchy, not like his, your hairline has receded much further back than in the picture, you keep trying to make yourself believe it, but you can’t...lie to yourself anymore. It’s not you, it was never you.

Confused and horrified, you start to cry, and I push you onto the toilet seat next to the counter. “Fuck, you really fucking believed it, didn’t you?’ I say, and then laugh, “You delusional fuck, you watched so much fucking porn, you actually thought you were a porn star! Fucking hell, I figured you were just a lying sack of shit when you showed up looking like this, but fuck--you actually swallowed your own bullshit too, what a fucking loser.”

You could feel all of these memories welling up, like some oily well had been tapped into at the base of your skull, the crude rising up and swallowing everything, warping it. You could recall all of those scenes perfectly, but each time you tried to put yourself inside the scene, your brain rebelled, dragging you out, putting you in front of a computer screen in your room, alone, jacking off your much smaller cock than the young cub had, imagining what it might be like to be him, trying to force yourself into him, squeeze your pathetic existence into his own somehow. It had started as a joke, really, impersonating him online, but people loved you, adored you, showered you with affection for the first time in your life, and you wanted the approval more than anything. So you’d kept going, and to help compartmentalize the guilt crystalizing in your chest, you told yourself it was real. That you should have been him, that you were him. The tears were slowing down, a muted horror taking their place on your face.

“So, give me a real one, one real fucking act of sex, not something ripped from some fucking porno,” I say.

You scratch your brain trying to summon one up, but that horror begins to bloom, as you realize there isn’t any. You’ve wasted years of your life in your room in front of your computer, jacking off to these same twenty-three videos, memorizing every detail of those scenes until you could recall them perfectly, then impersonating the young cub in a desperate bid to become him, until even you had believed the lie. “I...haven’t.”

“Wait, you haven’t had sex? At all? You’re a fucking virgin on top of it? Fuck, this is fucking perfect somehow, a fucking virgin...” I say, almost cackling now.

You’re still scrapping your brain, trying to summon up something, anything. One time, another man, or hell, even a woman, had touched your body willingly, and you simply couldn’t. All the way back, even in high school, you’d just been watching porn and jacking off, inserting yourself into the videos, fantasizing until you couldn’t even tell the difference between your perversion and reality anymore.

It was terrifying. You wanted to go back, you wanted to pull the veil back over your eyes, you wanted the confidence back, but looking at yourself in the mirror again, it seemed like you were even uglier than before, like more of your own imagination had sloughed off. You were just some overweight, middle aged troll. Of course no one wanted to touch you, you didn’t even want to touch you, you’d created an entire alternate persona just to imagine touching someone else. “Just...I’ll just go, I’m sorry, I...”

“Oh no, you think I’m just going to let you leave?” I said, “I cleared out my weekend for you, and you think you get to just waltz in, and then fuck off? Hell no, virgin, it’s time to get you fucking laid.”

You look up at me, and there’s a little kernel of hope there in your chest. You stand up from the toilet, tentatively reach out to try and pull me into a kiss, only for me to slap you across your face.

“Fucking--not with me you fucking idiot! After this shit you pulled, you think I want to fuck you?”

What the fuck is wrong with you? Of course I don’t want to fuck you, how the fuck could you have even thought that? The shame bubbles up again, but there’s no tears, just this naked sensation. Deprived of your lies for the first time in ages, you turn the contents of yourself that remain over and over in your hands, each side a new misery, a different embarrassment to the world.

“Come on, we’re going for a ride.”

We got in my car together. You’d arrived in the middle of the afternoon, and evening was already settling in over the city as we drove in uncomfortable silence. Uncomfortable for you, at least. I seemed perfectly at ease, like I’d had all of this planned and up my sleeve since you’d arrived. I’d allowed you to embarrass yourself in front of me for hours, pretending to be some hot porno cub, when it was plain to see that you were anything but. I must have known your secret before too, sussed out who you really were behind the screen, and I’d still invited you here, knowing that. You weren’t sure whether you should feel grateful or terrified. Someone wanted you, for something. Not for sex, for something else but being wanted was all you really needed to fill that gaping loneliness that you’d been trying to backfill with delusions all your life. We drove into a rougher part of the city, passing a number of strip clubs and small theaters, before pulling into the gravel lot of an adult video store.

“Friend of mine runs this place,” I said, the first words since I’d gotten in the car, “We already made arrangements. Get out.”

You do as I say, and follow me inside the building. It’s even grungier on the inside, which you find hard to believe, and there’s a hefty fellow behind the counter who nods to me when we enter. “That the guy?”

“Yeah, you all set up?”

“Come on back.”

Past the racks of videos and magazines for sale are some banks of booths, and past those, behind a partition, you find a row of gloryholes. The owner pops open a panel, and I push you inside after him. The narrow, dark space smells of sweat, the floor is sticky, and you try to back out, muttering something like an apology, or a begging for mercy, but I just shove you in hard enough that you fall to your hands and knees.

“I think you’ve wasted enough of my time, virgin. Time to pop that cherry. Now, you’re uglier than I was expecting, so I think this will do just fine, wouldn’t want you to have to try and convince some guy to let you suck their cock. And just to make sure you’re good and safe here all night long, my buddy here has a horse for you to ride.”

The owner pulls a chain, and a bare bulb pops on. There, at the far end of the narrow passage, gloryholes on both sides, is a fuck bench. You try to scramble up and past me, but I grab you by the hair and shove you forward again, pulling your clothes off. Between the two of us, we haul your fat ass onto the bench, belly down, and strap you on, securing you fast. Your face is mashed up against one wall, and your ass is pressed up against the other, with barely any room to squeeze. I shove a spider gag in your mouth and crank it open, before securing a thick collar around your neck and securing it to eye hooks on the side, locking your mouth in front of the hole there. We use a leather belt around your waist to do something similar to your ass, making sure you’re well aligned in the process. The end result is you, perfectly bound and ready to use between two glory holes. I thank the owner, and he just chuckles, saying it’ll be nice having a tight hole back here for once. I just chuckle, and throw you a glance. There’s something there, something I’m not telling you, but with your mouth forced open, you can’t very well ask me. We turn off the light, plunge you into darkness, and the door opens and shuts behind us.

There’s no real way for you to measure the passage of time, there in the dark. For a long time, nothing happens. After all, you arrived in the early evening, and the shop doesn’t see much traffic, especially in the back, until it’s good and dark. You try to call out, beg for help, but either no one can hear you, or no one cares, and you aren’t sure which might be worst. Eventually, a cock thrusts its way through the hole in front of your mouth, proceeds to fuck your throat without ceremony, and cums. You end up swallowing most of it, but some of it runs down your chin and dribbles onto the floor under you. The suddenness of it shocks you--technically, you aren’t a virgin anymore. It was deeply unsatisfying. Then you hear boots through the thin wall behind you, brace yourself, and another cock works its way into your virgin hole.

The pain is excruciating. You scream, but whoever is fucking you doesn’t seem to care. You hear a voice, speaking to someone else, “Fuck, Rick was right, the horse hole is fuckin’ tight tonight...”

“Serious? He usually only finds the old whores to ride it. He said it was some virgin tonight, lookin’ to lose it.”

“Fuck, what kind of loser would want to lose their virginity at a gloryhole? I wouldn’t belive it, but fuck, this thing is grippin’ me...”

He fucks you for a few minutes, and your hole refuses to loosen or relax, only clenched and tight as he forces himself into you, tears streaming down your face from the pain. He cums, and almost immediately, a second cock takes his place, likely the guy’s buddy. You’d hoped that the first violation would help ease the pain of the second, but it doesn’t. It hurts just as bad as the first time did, perhaps even worse, because this fellow takes his time, and is somewhat thicker than his friend.

It doesn’t take long for word to spread. For the next several hours, there’s nearly always a cock in your ass, and every single one hurts. You receive no pleasure from any of it. You thought back to the porno you would watch, to that hot muscle cub, how he always seemed to writhe in pleasure anytime a cock entered him. You’d always imagined it would feel glorious. This just feels angry, and rough, and violent. Exhaustion takes hold, your limbs growing numb. For a time, you drift, accepting that you’re nothing more than two holes to use, that this too shall end. There are longer and longer breaks between cocks as the shop empties out, and at last, the door opens. Not a single other man had entered the narrow space all night long--you wouldn’t be surprised if the owner had locked it, to ensure you received every load that got dumped here tonight. He unhooks you without ceremony, tells you to get up from the horse, and when you can’t, he just pulls you off and dumps you on the ground with a grunt, the wind knocked out of you, grabbing you under one arm and hauling you out, your numb legs struggling to remember how to move.

He drags your ass outside, naked, and you see that dawn is just beginning to spread across the horizon. He chucks your clothes on the ground next to you, and tells you that there’s an uber coming to get you and take you back to my place, and as much as you don’t want to go back there and face me, you have no real choice. You’re in an unfamiliar city, no one knows you--the real you, that is--and all of your luggage is at my place. The car pulls up, you climb in the back, not making any conversation. Your cum crusted face and the stink of sex rising off of you is enough for the man to put on a look of disdain in the rearview mirror.

You arrive at my place in the early morning. You check the front door, it’s unlocked. You come inside, step into the living room, and freeze. I’m lying there, reposed on the couch, and lying on the ground in between my legs is the muscle cub. The real life cub you’d spent years imagining yourself to be. In real life, he was so much more handsome than you could have imagined, and from the sheen of sweat, the smell of smoke in the air, and the glow on our faces, you imagined that the two of us must have spent a long and pleasurable night together, while you were losing your virginity to scores of anonymous cock.

“Stay where you are, pup, we aren’t done yet,” I say to the cub, get up from the couch and walk over to where you’re standing, filthy and exhausted. “I packed your shit for you--you’d better hurry and call an uber for the airport, cause I got things to do, and won’t be dropping you off,” I say. “But before you go, I want you to know a few things.”

I lean in closer. “First, there’s no going back to the other side of the looking glass. You know what you are now, who you are now. I wiped all your social media last night, deactivated every account, changed all your passwords. You want to get back on there, fine, but you’ll be doing it as the sad little wanker you are from now on.”

“Second, I want to assure you that it’s always going to hurt. That hole of yours is going to be tight enough to crack a walnut for the rest of your life. You’ll always want it to feel good, and trust me, for the guy fucking you, it’ll feel amazing everytime, but that pleasure comes at a price that you’re going to pay in pain.”

“You might be thinking, then I just won’t. You went so long without sex, you don’t need it, especially after it’s proven to be so disappointing for you. Well too fucking bad. You’re going to need it--but the only time a guy will fuck you is through a hole. No one will match you on an app, no one is going to give you the sexual time of day, unless it’s your mouth, or preferably your asshole on the other side, and nothing else. You could just suck them off, but you’ll put your ass to the hole more often than not. That’s the only way someone will say something good about you, about how tight you are, about what a good fuck you are. They’ll never believe it could be an old troll like you with that perfect fuckhole--literally, they won’t. And if you want that validation, if you want anyone to say anything good about you again, you’ll have to take the pain, and get fucked. Now get out of my house.”

After a long day of travel, you arrive home. A home you don’t remember well, a single bedroom apartment that stinks of you, of cum, of shame, of regret. You sit down in front of your computer, turn it on, and there’s a file there on the desktop you don’t recognize, a video file. You open it up, and there it is, three hours of me fucking that hole little cub in just about every position imaginable. You watch it, try to get excited, try to get hard, but as hot as it is, you can’t. You can’t put yourself in that delusion, no matter how hard you try, and can’t see yourself there with me, and you can’t enjoy it vicariously. After twenty minutes, you close the window and begin to pace. Twenty minutes later, you’re looking up the nearest sex shop that might have a glory hole. Half an hour later, you have your ass pressed to a thin partition, biting your lip and trying not to scream as another man drives inside you, the pain never easing, but you listen.

“This fuckin’ hole man, fuckin’ perfect.”

It’s a pittance, but it’s all you have. You play it in your head, over and over, jacking your meager cock until you cum, and cry, and know that I broke you, for good, and you deserved every bit of it.