Rise of the Guild Master

Chapter 14: The Seeds of a Harem Are Planted


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“So... besides getting me to fight the good fight and earning some gold, what else do we need toget things popping around here, Boss?” Sam sets aside her embarrassment as she leans toward me with a severe expression. Gone is the bashful Princess, replaced by an almost intimidating presence filled with determination and resolve. At least, she would be intimidating if it weren't for her sexy body still on full display.

The answer to Sam’s question isn't as simple as we have to do this or we have to do that. Rather, all sorts of tasks need to be fulfilled before we can truly call this Guild active once again. First and foremost would have to be...

"Adventurers, Sam. We’re going to need more adventurers."

"What, am I not enough for you?" Sam crosses her arms, smiling back at me with sass and a raised eyebrow.

"Nope," I answer her bluntly, shaking my head. "We only need a few more, not too many. The Guild is in no state to handle a ton of guests, and I just don't have the mental fortitude required to clean this place myself."

"Such a lazy, lazy man..." The brat sarcastically clicks her tongue before continuing, "Not that I blame ya or anything. I wouldn't wanna clean this mess up, either."

Lazy? Perhaps.

As I've already explained, It’s my fault this Guild is in such a sorry state. I won't linger on this fact and instead will look at it in another light. Sam taught me that I need to cling to my selfish desires and use them to better myself. One of those selfish desires is that I don't want to be the one to clean the Guild. After trying to do it myself for so many years, I'm putting my foot down. It's too much for one person, and I don't think Sam would lend a hand, either.

Therefore...

“I don't know what kind of adventurers we can conceivably convince to stay here when the Guild looks the way it does, but I can clean a room or two at most so we can have a little extra lodging if we end up finding anyone. Then, once we start building up that wonderful revenue, we can look into hiring housekeepers and eventually even some carpenters for renovations.”

Sam tilts her head and grabs a lock of her hair betwixt her fingers. As she twirls it around, the girl begins to smile with a devilish grin. "Ya might not have to clean any rooms if ya play your cards right, y'know..." She says with an equally mischievous tone in her voice.

"And what is my naughty little Princess implying, hm?" I reach out with my hand and cup her chin with my fingers.

Sam smirks, looking right into my eyes as she openly says, "Oh, nothing. Just that if ya found some more cute girls like me, then they could sleep in our bed, and ya wouldn't have to do any cleaning. Isn't that right?"

"Our bed?"

"I know what I said," Sam's face takes on a stubborn expression while still glaring at me.

"Sure, fine.” I shrug, hiding the fact that I’m more than a little happy to hear her call it that, before continuing and saying, “a harem isn't exactly in the cards right now, Sam. Even if I wanted one-"

"Which you do,"

"Yes, which I..."

Sam cracks up at making me slip yet again. Damn, she's good at this.

"C'mon, Boss. Ain't like it's all that surprising. Most dudes in Karnalle dream about being big, important, and rich enough to have a harem."

She's right. The tradition was made mainstream by the first King of the Realm, Rhoivandis Lundreame. Together with his six brides-to-be, Rhoivandis defeated the Demon Lord Orsovis, united the lands, and created the seven provinces. Nowadays, I believe the tradition is less about honoring the former King than it is for having an excuse for polygamy, but you don't see anyone complaining about it.

"Even if you're correct and I desire a harem, it's a miracle I’ve even managed to attract one girl. I'm not expecting to have much more opportunities to increase my bedmates, Sam."

"Just think about it, Daddy. You get another few adventurer girls like me, wrap 'em around your finger, and you'll have a devoted army of warriors who work their hardest so they can please ya on the battlefield and in bed!" To promote her point, Sam's smile expands until she looks like a lewd little vixen, where she then reaches into my lap and grasps my manhood through the blanket. Her grip is tight, firm, and she jerks the length a single time over the covers.

"Besides, do ya really think I can handle this monster all on my own?" She giggles, licking her lips. "I'm just one girl, y'know. Hell, I needed more breaks than you did last night!"

"Mmm," I lift my head back and put my arms out behind me, leaning into the developing handjob. Thoughts of playing around with loads of pretty Fighters and Mages fill my head, as do the sounds of a Guild overrun with perversion. "You really aren't joking about this, are you...?"

"Nah, course I ain't joking." Sam sees that I'm open to the pleasure she's dishing out and snakes her hand under the cover to take my cock into her grip. Her hand radiates warmth as it pumps my shaft.

"If we somehow managed to expand my roster of adventurers and lovers, where would that leave you? Are you sure you don't want me all to yourself?" I sneak in a bit of teasing amid strokes, delighting in seeing Sam's cheeks burn red. 

The Princess doesn't appreciate my games, punishing me in response by suddenly going faster and using the palm of her other hand to rub and play around with my cockhead. I groan from the amazing sensation while Sam frowns, admitting, "Sure. Sometimes I'll want some alone time with ya... but I ain't just suggesting this for your own benefit."

"Oh?"

Sam's smile becomes even more perverted as she snaps back into it. "I ain't interested in hooking up with other dudes, but I still wanna play around with other chicks- the more, the merrier."

"You're saying you want... mn... you want some harem sisters, Sam?"

Sam blushes at the term but doesn't stop her playful hand teasing. "I-I dunno, that's kind of a formal thing, ain't it...?"

"Sort of. Legally speaking, 'harem sister' is the term for the relationship between multiple women who marry the same man, but plenty of unmarried polygamists use the term when playing around, too."

"M-M-Marry?!" Her Highness adorably blanks out, losing her rhythm and slowing her stroking to a crawl. Seems she has trouble processing much of my sentence beyond the idea of marriage. "D-Don't you think you're getting ahead of yourself, ya old perv...?!" To make up for the slack, Sam doubles down and jacks me off even harder, summoning an even more resounding groan from my core.

"For now, why don't ya just see what happens and be on the lookout, m'kay...?"

I was already into the idea of having a harem all to myself, even if it's a rather comical aspiration at this current point in time. Not only is it hard to conceive happening, but I'm pretty sure there are also guidelines preventing a Guild Master from engaging in a sexual relationship with his adventurers, let alone several of them. Given how I've already crossed that line, though, I find it hard to care. Consequences be damned, Sam is making me fully realize just how badly I want this.

"Maybe you have a point, Sam. I think I'd like having a harem."

"You think? Geez, haven't ya learned a single damn thing by now?" Sam rolls her eyes at me, making sure not to stop her teasing for even a second. "Say it like ya mean it." She twists her hand around my cock, mixing in new movements to earn just another small inch of pleasure for me.

After another moan escapes me, I lock eyes with the Princess and summon up my confidence to declare, "I want a harem, damn it. I'm going to be the best damn Guild Master there is, so it's only befitting that I deserve tons of beautiful women and as much sex as I want."

Hearing me state my fantasies so bluntly seems to do it for Sam. Her emerald eyes flicker with both pride and arousal as she continues to massage my throbbing length. Then, as if to reward me for my selfish fantasies, the little brat adds in her free hand to the mix and starts squeezing me up and down, using both at the same time. Like this, Sam ensures that not a second goes by without my cock being milked.

"Damn, straight, Daddy! You're gonna be an all-important bigshot, so we gotta get ya enough bitches to act the part." Her gaze becomes hazy with lust before she asks, "Mmm... even though you already got me, ya wanna fuck other chicks, don't ya, perv?"

"Fuck," My body shudders as Sam teases harder, jerking the truth out of me from my dick. "Fuck yes, I do. You're not much better, though... considering how bad you want to whore me out to other women just so you can eat pussy."

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Giggling like the precocious brat she is, Sam promptly tells me, "Shut up," and moves one hand to my balls to mix in a few surprising and tender fondles before. "How bout ya go and tell me more about the kinds of chicks ya want in your harem, Daddy..." As she says it, the Princess starts grinding her thighs together. The thought of me hooking up with other women is exciting her just as much as it is me.

"I'm not that picky, ngh... my tastes are wide... I like all sorts of girls..." I admit to Sam, but it's not enough to satisfy her.

"C'mon, be more specific!" She punishes me by stroking her thumb up the length of my aching meat all the way to my frenulum. Once she's there, she starts wiggling it under her pressure. My hips bolt forward from the jolt it produces, and another groan leaves me.

"Shit-" I throw my neck back and close my eyes as I look at the ceiling. "Alright, fine! I want all sorts of women to fill my bed!"

"Yeah?" Sam goads me on in a sing-song voice, continuing her tip teasing.

"Yes! Big breasts and small breasts, tall girls and short girls, skinny girls... thick girls... and everything in between! I want them to have all sorts of... interests... and... and-!"

"And what? Don't stop!" Sam bites down on her lips, her eyes watery with lust as she keeps on pulling out more and more of my deepest desires. "Be honest with yourself. What do you want, Daddy?"

"I want to have so many loves that I won't be able to go more than five steps without someone fawning over me! Everywhere I look will be a devoted lover of mine, ngh- Human, Elf, Dwarf, Beastfolk, Halfling... I don't care what race they are, so long as they have a pussy I can fill up with my cum!"

"Gods, Daddy... you are such a damn perv, holy crap..." Sam is practically drooling at the thought of my perverted fantasy. Whether she imagines me fucking all of these as of yet non-existent girls, or she pictures all of the fun she would have with them by my side, Her Highness is clearly into it. She pushes her thighs together, grinding them into each other. "Show me how you would cum inside all those naughty adventurers... c'mon, Daddy... show me... show me...!"

Intent on pushing me to the limit and then some, Sam grabs on even tighter to my pulsing dick and doesn't let go. My beautiful young lover pumps my cock harder and harder, making damn sure we start the day off with as big of a bang as possible. Gods, she doesn't disappoint. My balls contract as I scream my orgasm into reality so strong and so fast that I don't even have time to warn the Princess.

An explosive volley of my white-hot semen explodes out of me, rope after rope coating Sam's face and tits before leaking down all over her persistent hands. Sam doesn't mind. She just keeps jerking until she's covered in an unbelievable mess of my own making.

Before it can completely coat her, though, Sam opens up her mouth and sticks out her tongue to catch the rest of my climax. Like a good little brat, she swallows the last few blasts before letting go of my cock once she's verified it's been appropriately nursed to completion.

I fall back against the bed, my body overtaken with post-orgasmic bliss as Sam starts the unnecessary but deeply appreciated task of cleaning herself up and eating it down.

"Mmm, nothing like a little breakfast in bed. Thank you, Daddy." As soon as she's done, Sam teases, laying down atop my chest and licking her lips like a devious imp.

"Anything for my Princess," I sigh, smirking down at her with a growing smile. Now that my nut has been achieved, I enter that ever-familiar state of sage-like clarity. "Gods, I just agreed to something ridiculous, didn't I?" I ask, realization setting in.

"You bet your ass you did," She laughs. "It sure is easy to get ya to do whatever I want, Boss. All it takes is one good handjob, and you're wagging your tail and barking on command for me. Good to know!"

"That's hardly unique to me, Princess. I'm sure you'd find most men more agreeable after giving them the same service. More importantly, I thought we were going to leave the bed?" I narrow my eyes at the nefarious girl who managed to tempt me to spend the morning screwing around once again. While sighing, I scoop up a drop of semen from her cheek that she missed and playfully push my finger into Sam's mouth.

Sam laughs, then sucks down on the finger and cleans it of my sexual fluid. "Ya coulda told me not to jack you off, you know."

"Yeah, yeah..." Leaning down, I crane my head to kiss Sam on her forehead, eliciting another giggle from the coquettish blonde. "Are you ready to get going for the day, or..."

She tenses up, tilting her brows down in disappointment at me. "Really, Daddy? Kinda selfish to just sit there and take a handy without giving anything back, y'know..."

Rolling my eyes at my lover, I concede and tell her, "You're scarily good at getting what you want, I swear... alright, have it your way. Come on up here, Sam."

"Oh, hell yes!" Understanding right away what I intend for her to do, Sam stands up on top of the creaky mattress and walks across it until her naked body looms over me like a giant. From down here, I can look straight up and see just how aroused this naughty Princess of mine actually is. Her fantasies have left her dripping sweet nectar between her thighs, and as she spreads her legs to show off, a long, thin strand of her juices falls from her lips onto my face.

"Daddy knows how much his Princess loves it when she gets to ride his face, huh?" Sam asks, her voice trailing off and becoming lewder by the second. While awaiting my answer, she drops to her knees and straddles my neck. Her steaming pussy is hardly a foot from my mouth- so close I can almost taste it.

Over these past few days with my Princess, I have acquired a taste for cunnilingus. Not too surprising considering how I'd always pictured myself enjoying it, but after seeing how wild it drives Sam and hearing all the luscious noises she made whenever I ate her out, there was no way I could resist falling for the act. Besides, it's not fair if you don't give back what you get. Sex is a two-way street.

"I sure do, so why don't you stop wasting time and-" Sam interrupts me in the most glorious way imaginable. By plopping her big, fat ass straight down on my lucky face and pressing her lips to mine.

"What was that, Daddy? I couldn't hear ya over the sound of you so desperately wanting to eat my tight little pussy...!" Sam sighs contentedly as I take her teasing to heart and get straight to work, lashing my eager tongue against the pink, wet folds of her labia.

The taste that awaits me is nothing less than pure lewdness given liquid form, filtered through a good deal of sweat. We were fucking fairly hard last night, and neither of us has had a bath yet, so the desperate stink of sex is still heavy on her body. Especially the part she's grinding up and down my face.

"Fuuuuck..." Sam rolls her head back, staring at the ceiling as I penetrate the narrow entrance to her slippery slit with my hot tongue. The girl bucks her hips, grinding her pussy and then her ass into my nose before rubbing her mound onto my tongue again. Once she's there, I lavish her with all I've got.

The more I lick, the heavier the honey dripping from Sam's pussy flows. Every little movement I make inside and outside of her hole gets a reaction out of the Princess, whether it be a moan, more grinding, or rising and sitting on my face again like she’s riding a bull. For my side of things, I enjoy the feeling of her soft, curvy ass resting its weight on me. Even the struggle to take in the air between licks and kisses fills me with a dangerous sort of satisfaction.

To get a better handle on the girl bucking away on my face, I reach up and grip Sam's hips in my hands. She welcomes my touch, so I grab down real hard and push her down even harder into my mouth. My tongue snakes itself even deeper into the Princess's wetness, savoring the taste of her tangy womanhood.

"Yes, Gods... yes..." Sam grabs my by the hair, pulling up and squeezing my head between her thighs. The pressure is intense, but my dedication is even more so. Even between a rock and a hard place, nothing can stop me from eating this pussy. "Daddy..." Sam coos, her pleasure starting to rise.

For a moment, the girl lifts her hips and looks down at the mess she's made on my face, marveling at the slickness covering my lips, my nose, and my cheeks. Her eyes are now totally glossed over in her own abundant perversion. "Mmm. You’re rushing, aren't you? No fun, Daddy. What's the hurry? I ain't going anywhere."

Pulling away from her silky pink sleeve long enough to answer, I meet her gaze and give Sam a sympathetic smile. "As much as I love playing with you, my dear, I really do want to get the ball rolling." Without delay, I pull down Sam's wide hips of my own volition, planting her ass back on my face as I start to feast from her dripping crevice while the girl is still taken by surprise.

Sam yelps from the onset of sudden pleasure brought about by the second my hot, wet tongue circles her pointy clit. Seeing how much she loved it, I began mixing precise attacks on the quivering weak point into my routine. So intense is her ecstasy that the Princess grabs me by my hair, like a rider taking the reins of their steed. She pulls up, shoving me into her pussy as her grinding picks up steam.

The girl gives me almost no time to catch my breath, relying less on me to get off and more on her own persistence. We can't have that, now, can we? My ego is at stake here, and I'm not about to go letting my Princess use me like a toy. I double the speed of everything I do to Sam, forcing her to cease her grinding and arch her back, moaning at my aggressive licking and oral caressing.

"Fuck, fuck-!" The beautiful girl whines in a lusty, fevered pitch. One of her hands leaves my head and gropes her bouncing breast, squeezing it to seize more pleasure out of her sensitive mound. "Daddy," Sam whimpers, her lower lips twitching and convulsing against my tongue. "I'm getting so fucking close...!"

Even though I could tell she was nearing the finale on my own, hearing Sam actually say it out loud excites me so. It rallies my enthusiasm, goading me to really sink my hands even deeper into her flesh. I hungrily force her to shove her entire weight downwards onto my face, even at the cost of hurting my jaw and disrupting my air intake. My sacrifice is well rewarded once Sam starts filling the room with the lewd noises of her perverse gratification, and she climaxes right as I forcefully burrow my tongue as deep as it can go, whisking it around like a vicious tornado.

Sam cums her cute little brains out, and I don't have any intention of stopping until my jaw physically locks up. Once I hit this point and try to pull away, though, Sam's body spasms from the pleasure and she sandwiches me between her thighs involuntarily. This fully cuts off my air in exchange for the deliriously soft experience of being drowned in her feminine flesh. Being squished by her legs like this feels like a dangerous sort of heaven, but I'm sure it's nowhere near the level of excitement Sam herself is facing.

She continues to moan and howl her way through her climax before eventually rolling off of me and settling down on the bed like a pile of twitchy pudding. "Damn..." She says, sighing and wiping some thick sweat from her brow. Then, with a smug expression, the brat lifts her eyebrow and turns to face me. "Ya really went crazy on me there. I think I'm gonna have to lay around for a while after that one, Daddy... looks like we won't get around to adventuring today either."

"Like hell we won't," I sit up and nudge Sam playfully in the ribs a single time before rising fully from the bed. "I'm going to go and get myself ready for the day. By the time I'm done, I expect you out of this damned bed. Understood?"

The lazy Princess laughs as she grabs her rib with her hand, saying, "Fiiine." and at last putting things into motion. I don't know what this new day has in store for us, but I'm oddly optimistic about whatever it may bring.

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