Rise of the Guild Master

Am I really going to do this?

Now? 

I lift the depressing looking knife and hold it out before my eyes, giving it a thorough once over using my analytical prowess.

This thing definitely won’t get the job done, but I sold all the other old weapons laying around a few years back. With no heroes staying at the Guild I had no reason to keep any. They were all just gathering dust in the storage rooms ever since their owners abandoned them. 

One of the many duties of an Adventurer’s Guild is to store any gold or items that an adventurer asks us to.

Weapons, armor, kill trophies, supplies... there used to be a veritable treasure trove that our Guild protected for our trusting adventurers when Grandpa was in charge. Strictly speaking, selling items left in storage by an adventurer is very against the Association of Adventurer’s protocol, but... their owners were never coming back.

Nobody would miss them and I needed the gold.

This old iron blade is the last actual weapon I have left in the guild. It must’ve belonged to a halfling, or maybe a gnome. Calling it a short sword would be more than generous, it's practically a knife. I kept it for self defense but I should have held on to a sword, an axe, or really just about anything else instead. 

“Will this dull thing even cut?” My eyes tell me no, but I can’t help thinking aloud. Out of morbid curiosity I press the blade up against my arm, nowhere lethal obviously, but it had me thinking. Being alone in a dark room tends to make you do that.

As the edge slides up closer to my skin, an existential sigh leaves my lungs.

I don’t want to become an adventurer- I’m a middle aged, washed-up sad sack who spends a fair amount of his days day drinking and reading erotic fiction.

Even if I’m in decent shape, it’s not like I can just pack it all up and go out slaying monsters. It’s way too damn late for me to just... just... oh, Goddess.

One last time...

Please...

Just one last time...

If I had even a single Adventurer, then... I’d know that this is what I should be doing with my life...

As if on command, the door suddenly explodes into a mess of sharp wooden splinters.

A crimson red boot kicks right through like it was no big deal at all. Powerful and efficient, my decrepit halls just became that much more ruined but at the moment I don't care. Whoever did this had power. Lots of it.

I look up to the figure who now stands in my doorway, silhouetted from the light shining behind them. They step forward with purpose and confidence, not walking into my Guild so much as swaggering. As soon as they enter fully I'm finally given a better look at them. 

Perhaps my analytical eyes were too distracted by divine intervention, because I didn't outright notice it at first. But the longer I stare at the intruder, the more convinced I am that I’m currently gazing at one of the most beautiful girls I've ever seen.

She has a head full of bright, sunlight colored blonde hair tied haphazardly into long, flowing twintails. Her hair suggests that it rarely goes brushed yet this unkempt quality only serves to give her a wonderful boyish charm that’s all her own.

Focused eyes of emerald pierce right through me when we meet and the expression evident on her face is a confident smirk. Her features look almost sculpted by the goddess Lux Ultima herself, being perfectly proportioned and otherworldly in their beauty. The only blemishes on her pink, healthy skin to be seen are a collection of rather fake looking freckles on each of her cheeks and a small pink bandage applied to the tip of her nose.

She wears red gloves with black sleeves, a brown and gold belt across her wide hips, and matching red boots with black thigh highs which dig perfectly into her thighs. As far as her armor goes she’s wearing a  skimpy red breastplate covering a questionable portion of her rather large, heavy-looking breasts, red shoulder pauldrons, and an embarrassingly revealing red, heart shaped crotch plate (arguably) covering her lady bits.

Why would she wear this? Is she expecting someone to stab her solely in the pussy and ignore all of her perfectly exposed skin? I thought armour was meant to protect your vitals, but what the fuck do I know. It looks more like a fetishistic parody of armor than it resembles anything an actual adventurer would ever wear. 

All this is topped off with one gigantic fuck off iron slab of a sword strapped to her back. The fact that she could haul that thing around with breasts like those makes me wonder if this chick has ever even heard of back problems.

“Sup, Boss? You’re the Guild Master here right?” The intruder finally speaks. Her voice is youthful, energetic and perhaps even a tad bit boyish.

She begins to approach me, the sound of her heavy steps creaking the wooden floor so badly that I grow worried that the poor Guild won’t be able to handle the weight of her sword.

“I’m here for some Quests, you got any good ones on... the... board...?” She stops her question as her eyes get a better look at me, or more specifically, what I’m doing. Her eyes shoot open with shock.

I can see why this would look bad.

She doesn’t understand the context, she only saw a sad looking man in shades sitting in a dark and lonely room with a knife pressed up against his skin.

I can hardly fault this girl for jumping to the conclusion she does.

With an unexpected savagery the adventurer girl stomps towards me so hard and angrily that my concern for the structural integrity of the wooden flooring all but doubles. Her face contorts into worried rage. She strongly rips the knife out of my grip and with her free hand the adventurer smacks me squarely across the face. 

She’s definitely strong enough to wield such a massive sword... the power of her slap alone is so strong that it feels like she somehow slapped the soul right out of my body.

With exaggerated tears, my guest looks me straight in the eyes with that beautiful, piercing green glare of hers. “BOSS, DON’T EVEN THINK ABOUT IT! YOU HAVE SO MUCH TO LIVE FOR!!”

I stare at her incredulously. Normally I’d pick up her implication immediately but I was more than a little stunned by the searing pain in my cheek. “Excuse me?”

She throws the knife over her shoulder and it falls flat on its side. “Look, Boss... I know this place looks shitty and all, but that’s no reason to kill yourself!” 

I blink awkwardly, rendered speechless from the strange situation I find myself in. “Thank you for the concern,” I manage to spit out. “But I believe there’s been a misunderstanding. If you just let me explain myself-”

With no warning whatsoever the blonde adventurer suddenly wraps her arms around the back of my neck and pulls me forward to bury my face in her deep cleavage. They’re soft and warm, sure, but her metal breastplate is very uncomfortable to feel pressed against the side of my cheek.

I can’t help but find myself feeling relaxed, though, as this situation brings to mind a woman very important to my heart that I haven’t seen in a long time. She used to pamper me in this exact manner way back in my childhood...

“It’s not worth it! We can work through this, Boss. We’ll sort this place out! Once I get moved in and all that junk and we get some quest money flowing we can start planning some renovations. This place could look a lot more bitchin’ for sure. We need like, weapons hanging from every wall and trophies from slain monsters should be on display everywhere you look! Fuck dude, you know what would be a REALLY good idea is if-”

“Alright, alright. Please calm yourself.” I raise my hand in objection as she squeezes me tighter to her iron chest. “There was a lot to unpack there but let’s start with the basics. I wasn’t going to kill myself.”

“Wha?” She blushes and suddenly stops hugging me into her tits. Skeptically, she looks at me with a raised eyebrow.

“I was considering a change of careers. That knife is- WAS the only weapon I had lying around and I was wondering if it could even cut. I absently mindedly held it up to my skin while lost in thought. You see, I was thinking about becoming an adventurer.” I sigh wistfully at my words as I say them.

The adventurer girl looks at me quizzically for a few moments before her cheeks puff out from trying to hold back a large amount of laughter.

She fails miserably.

My guest erupts into such a childish fit of loud, obnoxious, downright uproarious laughter that she bends over and holds her stomach for support. I give the girl ample time to finish up her fit but every time the laughter starts letting up she just just keeps looking at me and laughing harder. Just as I decide she’s starting to seriously irk me, she slams her fist down on the wooden desk and a decent chunk of the wood breaks and falls down to the dusty floor below.

“YOU? An adventurer?! Boss c’mon stop fucking with me...! What are you, like forty?”

I indulge in a nervous habit of mine as I adjust my shades from irritation. “I am only thirty-two. I’m sure I could make it if I tried.”

“Thirty-two? I guess you’re not THAT much older than me.” She holds back a playful, slightly bitch laugh. “Don’t kid yourself, Boss. You know most heroes start training from a young age right? Course you do, you’re a Guild Master!”

“Yes. I’m the Master of an empty Guild and my savings are likely to run out by the end of the year. I’ve got no idea what else to do with my life.” I don’t know why I’m being so open with this young adventurer, but despite her brashness she comes off warm, comforting and open.

She makes me feel like talking about this type of stuff with her isn’t a big deal.

“Well shit, yeah, I guess that’s pretty fucked. I thought Dewhurst was supposed to be THE village of Adventurers?”

Her words make me sigh from a deep, personal sense of disappointment. “You’re more than a little too late for that, you missed the heyday by a good twenty-two years or so. I think you want to head to Perlshaw, they’ll be better able to take care of you than I ever could here.”

“N-NO!” She immediately slams her fists down on the desk, large cracks now making inroads through the once pleasant veneer. I sigh, deciding it’s not worth confronting her about the ongoing property damage she’s causing.

“Oh man, fuck Perlshaw. I stopped there about a month ago to get my Hero license and fucked right off. Thank god you’re not as much of a creep as the guy who ran THAT place... Plus, it’s a little too close to the royal city for my taste.” The young adventurer nervously sweats, and her words cause me to raise an eyebrow.

“...You’re not some kind of criminal, are you?” I ask, unable to imagine why else she’d be so afraid of being anywhere near Imperalis.

“WHAT?! OF COURSE NOT!” SLAM. My poor desk. Rest in pieces.

I size her up, beginning to make use of my special eyes now that she’s raised a potential red flag. She seems nice enough, I don’t see any signs in her body language that leads me to believe she’s a dishonest person. Not to imply that my eyes are the be all end all bullshit detector, by any means.

Deciding to try and be a bit playful I sarcastically jest, “Then I suppose you’re some sort of runaway noble who fled to get away from her father and his stuffy advisors, hm?”

The look she gives me is the face of a child caught in a massive lie and, like any child attempting to maintain innocence, she begins avoiding any and all eye contact with the one who called her out on it.

“AHAHAHA, W-what the fuck are you on about, Boss? Me? Princess Samantha?! HAH! Y-You should try being a jester if this shit doesn’t work out, not an adventurer...!!” I’ve never seen a human being nervously sweat so much in my entire life and I honestly feel a little embarrassed for her.

Still... Princess Samantha? Is that one of THE Royal Family? We only have one king in Karnalle unlike some of the other realms and the horny bastard on the throne has so many children I can’t for the life of me recall if there’s one named Samantha or not.

“...Then what IS your name?”

“Sam, see?! SEE?! Look!!” Still nervously avoiding eye contact Sam fumbles her gloved hand inside her breastplate and pulls out a small card to present it to me. It’s a Standard issue Hero license from the Association of Adventurers at the lowest rank, Bronze. My eyes take in all the details it has to offer. Sam, eighteen years old, Human... Her class is Great Blader. I could have guessed that one, what with the ridiculously oversized hunk of iron she’s carrying around.

It’s not a fake license, I definitely would have noticed if it was. The damn things are notoriously hard to make forgeries of and few people would even bother since the barrier of entry towards becoming a bronze ranked adventurer is fairly low.

“Just Sam, huh?” I hand it back to her. “Is that short for anything...?”

She scoffs like I were stupid, “Well duh, It’s short for Sama-” Sam stops herself and panics before looking to the side. “Sam...ilda.”

“What kind of a fucking name is Samilda?” I ask bluntly, unable to hold my thoughts back.

“FAKE NAMES ARE HARD, OK?! I’VE NEVER DONE THIS BEFORE!!” I blink incredulously. “...Is what I WOULD be saying if Sam...ilda was a fake name and not a real name- which it is. It’s mine.”

If my desk were not already broken I would slam my face on it out of frustration.

“Alright, alright. Settle down. you’re obviously not leaving till I hook you up with a quest, ‘Samilda’ so let’s go ahead and get you saddled up with something appropriate to your skill level.” I pour on the business charm and even after five years of hardly getting a chance to use it.

 the lack of customers never dried up the skills, decorum and speechcraft I spent so long learning. I stand up from the ruins of what used to be my favorite desk. 

“You’re obviously a new adventurer, since Humans can’t get certified until they’re 18. Regardless, I need to know your quest experience thus far. How long ago were you certified?”

Sam beats her fist against her exposed breast like a proud gorilla. “Yesterday, my birthday!”

“...I see.” I knew she was eighteen, but now I’m starting to feel like a creep. I thought she was closer to nineteen with a body like that, but... apparently not.

Seeing my level of comfort drop greatly Sam suddenly sports a shit eating grin across her youthful, perfectly proportioned face and leans closer to me. She begins to teasingly run her gloved finger against my pecs and by looking down I can see a generous helping of apparently barely legal cleavage. “Oh my... is something the matter? Surely you’re a professional Guild Master and would NEVER look at such a young adventurer in your care with a pervy gaze... would you?”

“...” I say nothing, but that actually says a lot by itself.

Sam eventually stops waiting for my response and playfully punches me in the arm- teaching me the hard way that she’s not very good at controlling her own strength. “You’re pretty damn cute, Boss, not gonna lie. You know... I bet if a pretty little thing with daddy issues walked in she’d barely be able to keep her hands off you.”

“...Is that right? You know, with an outfit like yours one would hardly believe you would have daddy issues. It just makes you come off as so very cultured and intelligent. Really screams ‘I want my father to be proud of me’.” I sigh and look away, cheeks beginning to redden. This situation is getting fairly uncomfortable for me, mainly because...

Well...

I’m a virgin.

I may as well just out right say it.

I’m thirty-two and if I haven’t made it abundantly clear, no one in the town of Dewhurst has ever been all that fond of me ever since the incident with my grandpa.

We have an overabundance of brothels in this town so it’s not like I haven’t ever tried, but not one would allow me entrance. There are numerous girls who walk the Dewhurstian streets and in my loneliness I’ve even considered using their services but the temptation of a cheap thrill is never strong enough to overpower my desire to remain free of pelvic misfortune.

Goddess knows I don’t want the first trip to my physician in five years to be from a sexual disease... she’d sooner cut if off than heal it.

Like any man I have methods of escapism, I have my fantasies, and I have my right hand. I live vicariously through erotic fiction, which I collect, and have since resigned myself to a life of quiet sexual isolation.

So I never imagined that a young adventuress would just show up one day, start shoving me into her chest and awakening skeevy feelings inside of me...

But then Sam goes on to make it worse, using that most unholy and arousing of D-words.

“You know... I bet Daddy would look cuter if he took these things off.” The cheeky, youthful blond playfully tap tap taps the tip of her pointer finger against the golden rim of my glasses. “They’re cool and all but... c’mon. Really? This Guild is darker than a Gothiccan funeral. Who are you trying to impress by wearing sunglasses indoors?” She giggles and takes them off my face without knowing what she just did.

“SAM, FUCK- DON’T!!” Reflexively, I step back and cover my eyes behind my hand to block all incoming light.

Sam’s playful demeanor is instantly replaced with sincere, heartfelt concern.

“BOSS?! SHIT! WHAT DID I DO!? I’M SORRY, I’M SORRY!!” Sam hurriedly tries to put the glasses back on my face and accidentally drops them to the floor. They won’t break of course, they’re Dwarven-made. But Sam doesn’t know that. “FUCK!!”

When I reach over to try and pick them up for myself, we end up headbutting one another and she falls on top of me. It hurts tremendously because of how heavy her sword is and the pain makes me accidentally open my eyes.

Everything changes.

My heart starts beating faster than ever before.

This girl... 

Sam...

I can look at her. The way normal people look at each other... without my glasses and everything... it... it doesn’t hurt whatsoever.

She’s special...

She has to be.

I don’t know why else this could possibly be happening.

Sam, for her part, just stares awkwardly from her position on top of me. Not a single impure thought goes through my head even as her sword presses our bodies tight and close together. I know I’m staring, how could I not be? Her eyes are the most beautiful emeralds I’ve ever seen...

Sam senses that something is wrong with me and that I wasn’t just being an absolute creep. Her awkwardness fades and she looks down at me with concern. “Boss... are you doin’ ok there? Hello?” 

She doesn’t seem to be judging me at all, as far as I can tell she’s being entirely sincere.

I’ve been shut away from the world more or less for five years, and this is just... overwhelming.

I need to stop being weird, I need to stop-

“You’re beautiful.” I say, tears forming in the corners of my eyes.

“W-WHAT...?!” She stares back down at me not in revulsion, but in confusion. Of course she does blush, though.

Shit... fucked the whole not being weird thing up didn’t I?

“N-Nothing, please... glasses... please, help me find them... I can... explain...”

“I’m so sorry...!! Here! Here they are...” She hands them to me and I quickly press them back to my face.

“C’mon Boss, snap out of it...! I’m sorry, I’m so sorry I took your glasses, please... PLEASE don’t be disappointed!! I don’t have anywhere else to go...” Sam says as she sits up and extends her hand to pull me up.

I take it gratefully.

“I’m... I’m ok...” I raise my hand towards her to assure her, wiping my tears and looking away from her radiance out of fear that it’d happen again.

“Uh, yeah right, what the FUCK was that...?!” She doesn’t believe me and gets up in my face. I wish she wouldn’t. I don’t think I like feeling like this.

Also, she smells nice. 

“I... need my glasses for medical reasons. They’re dwarven made- enchanted, I...” I struggle with trying to figure out just how much of what I just experienced I should relay to her and how best to describe my condition.

“My eyesight is special. In a way you could say it’s too good. Having my glasses off for even a split second... it’s like an explosion of clarity that I never asked for. It hurts. A lot. Even more so than when you slapped me.” I let out a cheap laugh, trying to ease the tension between us.

She doesn’t take the hint.

Sam takes my hands in hers and my heart practically explodes. She’s wearing gloves, but for some reason I still feel the warmth of her hands burning through. She looks me straight in the eyes with no hesitation.

“No. Whatever just happened to you it was... a lot more than that, wasn’t it? I... felt something too.” Sam squeezes my hands tighter in an attempt to comfort me but I can’t take it, I pull away and start walking away from this awkward situation and towards the quest board on the other side of the room.

“Thank you for the concern, but no. Happens all the time...” Clearing my throat, I extend my arm out towards the wooden board on the wall filled with quests. “Allow me to introduce Dewhurst’s one and only quest board. We don’t ever get local work from the townspeople these days but regardless there’s always plenty of Association issued daily quests. Like this one, always a classic for young adventurers looking to prove themselves and start small.”

I take off a quest flier and hand it to her. Sam is currently crossing her arms and staring at me with great worry, but her expression is slowly returning to that slightly determined look she came in with.

“Y’know, I’m planning on living here. We don’t have to do this right now. You need someone to look after you and frankly I don’t wanna leave you alone right now, Boss.”

The thought of her staying here was way too much for me to bear currently. Sure, an Adventurer’s Guild is supposed to always have spare rooms and dorms for adventurers who would prefer to lodge here instead of staying at pricy inns.

Here, though? All of those rooms are dilapidated beyond belief thanks to my neglect. The only room that’s livable at this moment in time is my own bedroom, and it only has a single bed.

Sam refuses to take the flier from my hands and continues to stare at me stubbornly. I sigh deeply and don’t stop trying to hand it to her until she takes it.

“Look, this is... totally normal.” I lie, and she knows it. “I know how to handle myself. Just... please go on this quest and give me some time alone for a bit to sort things out. It’s super simple, you won’t even be gone an hour. Just head out the eastern gate and slay five slimes. Please.” I look at her pleadingly.

Sam apparently decides that my terms aren’t so bad and takes the quest flier from me, but doesn’t break eye contact as she does so. She stuffs it into her breastplate.

“Go rest, Boss. Now. I’ll be back and we can talk about my lodgings... and whatever is going on with you when I get back. Ok?”

I nod my head with surprisingly meekness. Her voice comforts me, it’s confident and brash... gives me something to latch on to while I try and sort my messed up emotions.

“Yes, indeed. Don’t worry. I’ll be right as rain be the time you return, alright?” I try and feign a confident smile but judging by the look on her face I can tell it wasn’t very successful.

“...Good.” Sam raises a skeptic eyebrow. I don’t need my analytic eyes to tell me she doesn’t believe me, but she turns around and starts heading to the door she mercilessly kicked in. 

I will admit to my wandering eyes glancing perhaps too long at her shapely behind on her way out.

“See ya in a bit, Boss...?” She turns back to face me, still concerned, until her eyes trail downwards and she blushes fiercely. While it’s not quite as playfully as earlier and very clearly still worried for me, she seems relieved for some reason.

“Holy SHIT, dude. You uh... might wanna take care of that... Daddy It’ll calm you down a lot.” The supposed Princess points down with her finger before finally leaving the building with an amused smile on her face.

I look down in horror at my pants to be greeted with the biggest erection I’ve ever had.

I feel ashamed, confused...

Nothing about today makes any sense, I was supposed to be closing the Guild and becoming an adventurer. What is with all this additional nonsense coming out of the woodwork at the eleventh hour?

The only thing I know for sure is... I should probably follow Sam’s advice, and I’m so turned on I don’t think I’ll be able to make it upstairs.