Rise of the Guild Master

It's almost amusing how fast my mood is able to flip on its head. Sam and I may have been having ourselves a nice little dinner, and the conversation we had was the most fun I can remember having for a very long time, but all it takes is a single question from the Princess to pull me out of the moment and right back into an awkward pit of sexual dread.

Sam leans over the table. With a purposeful glint in her eye, the adventurer asks, "Dinner was nice, and all, but boy am I tired. Hey, speaking of... what's the sleeping arrangement gonna be like, Daddy?"

I almost choke right then and there on the last drop of my cocktail. Sam is worried while witnessing my strong reaction, but once I recover, the cheeky brat only feels more empowered by her effect on me.

Clearing my throat by pounding on my chest, I look Sam in the eyes while trying to remain in control of myself. "Because you were gone shorter than I expected, I didn't have time to clean up one of the spare bedrooms for you. The adventurer dorms in the west wing happen to be in a sorry state, too, so... there really isn't any other option for you except for-"

"Say it," Sam smirks, narrowing her eyes with glee. "Say the words, Boss. C'mon. You got this."

"Except for my bedroom..." I admit with a heavy heart, placing my forehead into the comfort of my palm.

"Nice," She laughs, celebrating her small victory. "You were too busy jackin' it to do your job, huh? No big deal. Happens to the best of us!"

Embarrassed, I slam my fist into the dining table loud enough to rattle the plate. "There were extenuating circumstances which made my sexual release a necessity. If I didn't follow your advice, I would have remained out of sorts."

"Hey, hey!" She places up her hands, smirk still wide on her face. "I ain't judging! You got a point, too. I mean, look at yourself. So calm and relaxed... wait, nope. I think you're getting worked up again, Boss. Maybe you should have another go at it?" The classless Princess starts stroking off an invisible dick with her hand to really amp up her teasing.

I breathe in through my nose and look away as best I can. "Oh, me? I'm not flustered at all. Why would I be? It's not like I'm being constantly being harassed by my newest employee, no. That surely wouldn't be cause for concern."

The precocious brat tilts her head like a confused but very determined puppy, leaning in even closer across the table. "Got a question for ya, Boss."

"Assuming your question is appropriate, I may have an answer in return."

Sam takes me by my blind side, asking, "You aren't freaking out just cause it's an age thing, right?"

"What?" I look back at her, now just as confused as she is. "I'm afraid I don't follow."

"This," Sam gestures to herself and then to me. "Whatever the fuck's going on here. At first, I thought you were all worried cause I'm a whole lot younger than you, but... there's something else, isn't there?"

Before I can answer, her eyebrows raise as if she's just figured out the punchline to a joke only she is privy to. "Oh, no way...! Are you a virgin, Boss?" Her eyes glimmer with what looks to be optimism, of all things.

"I don't see how that's any of your-"

"Any answer besides 'no' is an instant yes, just so ya know." She giggles.

I need to remember that this girl is much more perceptive than I give her credit for. Any attempt to wiggle out of this conversation will only make me appear more suspicious, thus increasing her teasing. "Sam, I'm an adult. If you absolutely must know, I obviously have many sordid affairs under my belt, and I am a frequent purveyor of Dewhurst's many brothels."

"Frequent, huh...? Wow, sure sounds like I'm in good hands." Sam lays a trap.

"Indeed you are, I-" I say, only realizing the slip up I just made before it's too late.

Sam snorts and falls onto the table, squealing left and right. "Fuck, you're so fun to mess with! Oh, man..." The brat wipes a tear from her eye, saying, "Just own up to it, Boss. Nothing wrong with being a virgin... I mean, I would know."

I give the girl a suspicious look as if I don't quite believe her.

Sam takes my glare as an accusation and leaps out to defend herself. "Hey there, the fuck's with that look you're giving me? Why it's almost like ya don't think I'm a virgin!"

"You're putting words in my mouth,"

"Only words that you're saying with your eyes!" I chuckle at the way she phrased it, knowing it's somewhat true.

"You're dressed like a harlot and have done little more than flirt with me from the moment you burst through the doors," I tease back. "Forgive me if my expectations were misguided. I have no idea why that might be the case..."

Sam starts to get angry on account of my sarcasm, and it's a fearsome sight. Her cheeks flush, and she throws her emptied mug at me. "I said it's ‘cause you're cute! Gods!" Sam yells. "Can't a girl just flirt with a dude she just met without it being weird? Is that too much to ask?!"

Dodging the cup with an amused smile, I retort, "It is when the man is fourteen years older than you,"

"I said it once, and I'll say it again, old man," The bratty Princess points her finger at me like she was issuing a challenge. "I know my type!"

Sam and I end up catching each other's eyes before the absurdity of this little back and forth resounds between us. I laugh, and soon enough, she joins in alongside me. For a moment, we just enjoy the feeling of being around someone else who inexplicably 'gets' us.

I can't explain why I feel so comfortable around this brat, so I can't really hold it against her if she feels the same way around me.

We soon catch our breaths as the moment passes, and after it does, Sam stands up. Leaving her spot on the opposite side of the table, the young warrior walks over and sits down at mine. Rather than scooting away from her and putting some distance between us, I let it go. It’s mainly because it feels nice to have Sam so close, and also having to force myself to deny our chemistry is starting to become rather tiresome.

Sam props her elbows on the creaky wooden table, asking me while staring at the ceiling. "Do ya mind if I ask a personal question, Boss?"

I prepare myself for another flirty jab, answering, "I suppose,"

Her actual question is more upsetting than I expected. Had I known, I would've much preferred another flirty jab. "How did this Guild become so rundown and crappy looking?" She asks.

"Long story," I sigh, joining her in staring at the ceiling. "And before you try anything cute like 'well I'm not going anywhere', it's a long story that I don't particularly feel like telling." I say. Not now, at least. Not after such a nice day. Hell, not after what might be the only nice day I've had in so long.

Sam is insistent, however. With a sideways glare, she lets me know with her disappointed gaze. "C'mon... give me a summary or something. I wanna know. Especially since it sounds like there's a lot of baggage there."

"Are you always so nosy?"

"Depends on if I find the person I'm talking to interesting or not,"

"Was that a compliment?"

"You're the smart one, you tell me!" Sam nudges me in the ribs with her elbow.

Her cuteness brings my mood back up a bit, so I tell Sam an abridged version of the truth with a shrug. "I just stopped trying. Not much more to it when you get down to the meat of things. Cleaning and maintaining the building was impossible for one man to do by himself, but-"

"Didn't you ever have anyone around to help out?" Sam asks, her concern growing harder to contain.

“I did until I couldn't pay them any longer. That was a very long time ago, though. Not having any assistance wasn't the reason I gave up. I had already been taking care of the Guild on my own for years until then."

"Well, if that ain't the case, why did ya give up?" Sam turns to face me, looking worried about discovering the answer.

"It just felt like the right time," I sigh, sinking further into my seat out of shame. "After Bridgebury, your... well, the King was under a lot of pressure to do something about the Demon Lord. That led to the Perlshaw Guild being built, which ended up putting Dewhurst off the map completely. Nowadays, I don't even get travelers using my Guild as a resting point. Not that I can blame them, I would rather stay at an inn, too, if I were them.."

The girl grits her fists and sits up straight, taking on a combative pose. "Are you saying the Demon Lord led to all this? That bastard...!"

"No," Laughing, I shake my head. It would be nice if I could use the Demon Lord as some sort of scapegoat for all my problems, but that's just not the case. "I have no one but myself to blame for the Guild turning out this way. My whole life has just been one bad decision after another, and living with that weight has damaged me."

"Boss..."

"I can't stop myself from thinking that if I had tried a little harder, maybe this wouldn't have happened, and maybe this Guild would be thriving... which is a bad habit to fall into. When you start contemplating on what you might've done differently if only you had a chance to change all of your mistakes, you sentence your brain to a self-imposed prison spiraling ever downward. You think maybe this, and maybe that, or maybe this... maybe, maybe, maybe. What a dreadful word." I stare at the bottom of my empty glass, wishing I had more alcohol after launching into that tirade.

"Uh... that was..." Sam gulps, wiping sweat from her brow.

"Depressing?"

"Concerning." The girl gives me a worried frown.

"I did tell you not to ask me about the Guild, didn't I?"

"Yeah, but I didn't think you were gonna go all doom and gloom on me..."

"Sorry," I feel a bit bad about dragging her down, but there's a good reason I didn't want to talk about this.

Sam took it worse than I expected, and she shocks me by banging her fist on the table with righteous indignation on my behalf. She looks me in the eyes and grabs me by the collar, declaring, "You're selling yourself short, Boss. I can only speak for myself, but you've been super helpful and really nice to me even though I keep messing with ya. Hell, you're even good at cooking and mixing up drinks! If you aren't the best example of what being a Guild Master is all about, then I don't know what is."

Once she's done delivering her counter-argument, the girl lets go of my collar, and it takes me a moment to respond. The conviction in Sam's voice is almost convincing, and I feel it stirring something up in me that I've long since forgotten. When she says that about me, I nearly catch myself believing I could become the kind of man this girl thinks I am.

"That's very nice of you, but you should know that just because I look the part and act the part, it doesn't mean I'm good at the part." I tell her, cursing my pessimism as it forces me to deflect any and all praise.

As a result of my unchecked self-deprecation, Sam's irritation rises. "You're too hard on yourself, you know. Do ya got something against being happy, or what?"

"I wouldn't say I'm against the idea, just unused to it."

"Well, that's a buncha bull crap. Even if ya can't see it, there's something special about you, and it ain't just a pair of magic eyes. The may you say depressing junk like that, the more I'm starting to think I ended up here for a reason."

If I were a more religious man, I might agree with her. I'm not entirely on board with the idea that the divine delivered this busty blonde brat to my doorstep simply because I prayed for another chance, but I'm not dismissing the possibility, either.

"If only I should be so lucky. Surely you don't think that her Holiness Lux Ultima led you to my doorstep to use you as some sort of cure for my mid-life crisis, do you?" I ask, mostly to get a read on her opinion of the strange possibility.

"I dunno about the Goddess, but I definitely wanna kick your ass into gear and get you to acting like such a sad-sack!"

My overwhelmed state gets the best of me, and I again feel humbled as I see just how far this girl is trying to go to cheer up a washed-up bastard like myself. It may seem pathetic, yet, I really don't know how to respond to such kindness. Doing my best to remain open to the idea, I give her a smile and say, "Part of me feels it's too late for that, but... it means a lot, Sam. It really does."

Sam senses my evasiveness and it makes her cross her arms, once again huffing and pouting while she does so. "I ain't giving up on you, Boss. Even if I have to use the sorta weapons that are only available to a sexy woman such as myself!" She declares so seriously that there's no doubt in my mind the girl means what she says.

"...Right, well, let's just hope it doesn't come to that," I stand up from the table, piling up our dishes one on top of the other. "In the meantime, you're welcome to my private quarters-"

"Pft,"

"My room." I correct myself, sighing yet admittedly amused at her immaturity. "It's too late to start cleaning up a room for you, and the dorms in the east wing are in even worse shape. There's no other choice."

Only moments ago, we were having a serious discussion that bordered on being heartfelt. Now, Sam is back to her same inappropriate antics, smirking as she says, "Inviting me up to your bedroom, huh? Now that's more like it!"

"Don't get your hopes up. I’ll be sleeping on the sofa back in my office."

"Whaaaat? Boo!" She blows a raspberry.

"You didn't really think that we were going to share a bed, did you? I've known you for less than a day."

Putting her hands on her hip and giving me a sassy look, Sam snaps back, "And who's to say I won't make ya share one with me, huh?"

"I don't care how much you like older men. You can't tell me you're possibly desperate enough that you would force me to sleep beside you."

Wasting no time at all, the girl proves me wrong by using only a fraction of her absurd power to kick my shin. Pain surges throughout my leg. Through sheer force of will, I barely prevent myself from collapsing onto the table and dropping the tray containing all of our dishes.

Next to me, the blonde brat gasps and pretends to be shocked as if she weren't the one who just kicked me. "Oh, no! Are you doing ok there? Looks like somebody went and got themselves hurt, Boss. There's no way I can let ya go and sleep by yourself, now. Someone's gotta watch over you!"

Wincing from the ongoing agony in my, I grit my teeth and ask, "Are you fucking serious right now...? Really? These are the depths you will sink to, Sam?"

"Shush," The Princess dismisses my concerns as she gets up from her seat. "That's enough outta you. C'mere, ain't no way I'm letting ya sleep on the couch in your own damn home!" She bends over, attempting to hoist me over her shoulder like I'm some sort of damsel in distress.

I push the mighty warrior away with my hands, stopping her before I can be entirely emasculated. "Will you just wait a damn moment?"

Snickering, the brat asks, "Why? You gonna tell me your heart isn't ready?"

"No, you damn rascal, I'm not even ready for bed yet. The dishes still need to be done, and there's plenty of paperwork for me to fill out regarding your quest so let go of me, already!" I tell her off, causing Sam to relent and back away. She's sad to do so, obviously wanting to have had a chance to manhandle me.

"Fine, fine... do your job stuff if you really have to. I mean, it's not like you'll be able to run away from me for too long with a leg like that!" She laughs to herself, a nefarious look in her eyes telling me that the night is far from over. "Where's our room, Daddy?"

Knowing better than to argue against her usage of that devilish word, I shrug, defeated as I answer, "Up the stairs, first door on the right. Make yourself at home."

"Oh, I wouldn't worry about that..." Flashing me a grin with her sharp, pronounced fang on full display, Sam sways her hips side to side while sauntering over towards the rickety stairs. She knows damn well what she's doing, drawing my eyes to her barely-covered behind and its luscious, full, fatty cheeks.

With a playful wink, the girl leaves me to my own devices and ascends. "Don't take too long now, m'kay? I'll come and get you myself if I have to!"

As I watch her go, I understand now without even knowing for sure that if I were to really sleep beside her, then my life will change forever. I can't pretend I know exactly what's going to happen, but I do know that it's unavoidable that something will.

Sam has spent all day toying with me, and I feel like I'm coming up fast on the point of boiling over. I'm only human. My patience, as well as my self-control, are both running thin...