Rise of the Guild Master

Sam isn't going to let me stall out answering her question, not now that I'm finally beneath her and at the girl's absolute mercy. The mighty Princess bares her youthful, naked body down against my own, drawing my eyes up into her stunning form and her gratuitous curves. Despite already seeing most of her figure thanks to her attire, the bits I was missing out on were somehow even better than I had dared dream.

Narrowing her eyes, the girl grinds down her naked pelvis into mine. "Did... you... like... what... you... saw...?" The fiery brat asks slowly and quietly while pushing down even more weight on my rapidly expanding manhood. A soft moan flees my lips, the distinct valley of Sam's cleft parting around the outline of my cock.

I can feel her pussy heat through my boxers. She’s so warm.

Swallowing nervously, I pull my eyes from Sam's tantalizing indecency and look up at the girl's face. "Sam, get off of me. This is... unacceptable... why in the Goddess's name aren't you wearing any-"

Sam rolls her emerald eyes, and I see just how pretty they look as the moonlight creeps in from the window behind my bed. "The fuck kind of stupid question is that s'posed to be, Boss? Did ya think I somehow had a full set of pj's stashed away in my bra? No, dummy. You saw what I came in with, nothing but a big ol' sword and the clothes on my back."

"Right..." My sweating becomes more profuse as I nod at her statement reflexively. "If pajamas were the issue, you could have asked me for something to wear to bed, though... it might not fit, but-"

"You know damn well this ain't about the pajamas,"

"Sam..."

"So, ya aren't gonna answer me, then?" Sam's voice fills with a shrill venom. Her eyes transform into piercing daggers, striking holes into me with just her deep, dire disappointment. Out of irritation, the girl clicks her tongue and frowns.

"You know that I can't," I scramble to try and explain myself out of this awkward situation to little avail. All of my squirmings just make Sam use more of her superhuman strength to push me down. "Damn it, you can't just ask me to-"

"I can, and I did," Sam growls, demonstrating she's no longer having it. "Man the fuck up and look at what I've got so you can tell me what you think."

Pinned and trapped like a cornered animal, I gaze up at the nude figure straddling me in the shadows. Surprisingly, night vision is not one of my ocular abilities, but there's more than enough light coming in for me to make out every last detail of this girl's young, generous body.

Sam's sizable, soft, round breasts fall down from her chest in a perfect teardrop shape. Impossibly perky despite their robust size, they only look more prominent than ever before without the straining confines of her breastplate.

In the center of each enticing tit sits a pink and pert nipple, with an areola that's not too large or not too small surrounding it, no larger than a golden coin. The open air of the room, or perhaps Sam’s arousal, has pointed and hardened the tips of these delectable nips, making it hard to stare at them without feeling an intense need to suck from them.

Her bare naked skin is without blemish, her body defined primarily by curves upon succulent curves. A few parts of the girl are on the thicker side, mainly her wide hips, meaty thighs, her fat bottom, and of course her chest, but I can't understate how much I'm into that. Her mound has a little bit of extra meat, too, and it's hairless to boot.

Behind her, Sam's golden hair flows down her shoulders, past her back, and down to her butt. The sheer amount of hair her puffy twin-tails were holding back is astonishing, but it's impressive to see just how much letting it all down does to change her image. 

Before, Sam looked like a bratty tomboy with all those unkempt curls. Now, those same curls cascading off in every direction make her look like a beautiful and even sensual goddess.

In every regard, this girl is immaculate, resplendent, and plenty of other pretentious words I could rattle off the top of my head. So why can't I answer her question? Why can't I tell her how much I like what I see?

Is it because the age gap between us complicates matters, and I fear what others would think of me if I pursued her?

Is it because Sam is almost certainly the Crown Princess of Karnalle and that becoming involved with her would potentially land me in heaps upon heaps of trouble?

Perhaps it's neither of those things, and it's just because I lack the self-confidence required to tell her how I feel. Hell, the age gap is hardly a problem when you look at all of this Realm’s political marriages. Maybe it's just that I don't feel like I deserve any of this. I really don't even know at this point.

Even with my thoughts churning in loops and loops, Sam allows me more than enough time to properly stare at every inch of her naked body for as long as I desire. While I know that some part of me desperately wants to break the silence and escalate things further beyond this point, I can't bring myself to throw caution to the wind even when so many of my fantasies are here looking right into my eyes.

What kind of loser has a stunning girl literally pressed up naked against his cock, yet all he can think about is how much of a disappointment and a failure he is? This one, apparently.

Still sounding disappointed, Sam raises an eyebrow and asks, "Been long enough, I think. Gonna take it ya still can't answer me?"

"Yes," Almost without hesitation, I admit the truth to her in shame.

"Gods, you could at least hesitate a little when you admit to having no spine..." She groans, looking frustrated beyond belief. Sam closes her eyes just as she's had enough and then leans down forward. Her heavy breasts drag against my shirt as she presses her lips forward like she was going to kiss me, only for her to slip past my guard and slide up to my ear.

In a purposeful yet quiet whisper, Sam asks, "Do you want to know why your Guild is in such a crappy state, Boss?"

I blink, suddenly surprised and taken aback thanks to this bizarre change in topic from the naked girl. "Excuse me?"

"It's because you can't stop acting like such a sad-sack," Sam says, her voice swelling with conviction making her sound absolutely sure of herself.

It takes a second for her words to actually register. When I finally understand exactly what Sam just said, I'm met with a mixed set of emotions triggering many different responses all at once.

I'm angry, and I'm sad.

I agree, but I disagree.

I try to lean up, to lash out at Sam and push her off of me, but Sam's strength puts a stop to that right and early. Even despite her power, I still struggle with everything I have.

I'm determined to yell or to tell this brat that she knows nothing about me and what I've been through. I want to tell her something, anything, really.

After battling long and hard against myself, I end up with, "What the fuck is your problem? You barge into my home, and you-BLUH?!"

I don't get very far. Sam takes my lips in between her fingers and shuts them tight just after I start talking.

The glare in her self-righteous eyes is equal parts awe-inspiring and demanding. When she's like this, I feel like a man forced to kneel before his sovereign.

"Shut the fuck up when I'm talking. You got that?" Sam asks, waiting for me to respond. I nod my head up and down, unsure of what to expect. Satisfied, at least for now, the Princess lets go of my lips yet keeps her disappointed gaze trained on me at all times.

"There's your problem right there," Sam sighs, shaking her head like she knows all the answers.

"What?"

"What do you think? This!" Sam gestures at me with her hand. "I'm talking about this right here, damn it. You just shut your trap like a total bitch when I told you to. You're weak... soft, even."

"And this has to do with my Guild... how?"

"It's got everything to do with your Guild, dummy. I'm sure you worked as hard as you said you did, but that entire time, you couldn't put your all into it... could you? Something was holding you back." Sam leans in close to my face. Our noses touch, her emerald eyes shining in the darkness as she glimpses into the deepest recesses of my soul. "How about it, Boss? Any idea what that was?"

Of course, I do. I'm many things, but I'm not a fool. I spend every day thinking about how everything is all my fault and how I've done nothing but screw myself and everyone else over just by existing. I'm well aware that I'm holding myself back.

But have I ever admitted it so openly? I don't think I have, and although it took this girl a lot to force it out of me, this might be my chance to admit to having a problem. My fists start trembling, and my mind feels like I'm on the verge of breaking down.

Sam's question whirls about in my thoughts like a storm until finally, my words are found.

"I'm the one holding myself back..." I mutter, scarcely more than a whisper.

The girl doesn't want me being evasive. "Louder," She says, pushing me out of my comfort zone.

"I'm my own worst enemy," I speak, following her advice as I raise my voice. 

"Better," Sam nods her head. "Any idea why that is?"

"Probably because..."

"Because what? C'mon, Boss. You're doing good. Stay with me, here."

"Because I... don't think I deserve to be happy, on some level..."

Fearing that my negativity is going to make things worse again, Sam loses some composure as she asks, "Well, why the fuck not?"

I spare her the details, remembering what it was like when I droned on about my depression after dinner. It would only drag me down further, and Sam won't stand for that. "Because my life has been nothing but mistake after mistake. Thanks to that, the people around me have suffered endlessly as a result." This is what I tell her, and it gets a surprising response from the girl.

"So what?" Sam asks, tilting her head. For a moment, I'm baffled at how she could dismiss all of the people I've hurt like it was nothing... but then I realize that may be her entire point.

Unsure, I ask, "What the fuck do you mean ‘so what?’"

"What I mean is that it's not like you intentionally screwed other people over. I don't know what you've been through, but mistakes aren't something you should dwell on forever. They're something you should own up to, grow, and learn from. I may be just a kid, but even I know that much. I mean, I made tons of mistakes earlier today, and I had you there to point 'em out for me. If I can do it, why can't you?" The way Sam says it in her high and mighty voice makes it sound like she's mocking me, even if I know she's not. Sam is just telling me the truth, in that brash, honest way of hers.

"E-Even if you're right," I ask, a slight crack in my voice appearing due to my rising emotions, "How am I supposed to just... move past everything until now?"

"You could start by focusing on yourself, for one. Think about what you want, what you need. Then, remember that nothing in this Realm is handed to you and that if you want something, you gotta take it. Take what you want before anyone else can get their grubby mitts on it, and make it yours!" She pumps her fist in the air, making her breasts jiggle.

"And how will becoming a selfish thug like that help me?"

"Because you're the type who can't stop thinking all the time. We can't stop that without inflicting some brain damage, which I'm guessing you're against?"

"You presume correctly,"

"Right. So if we can't stop you, then we gotta get your big 'ol brain focused on forward momentum. Work towards everything you want, and when you get it, work on grinding towards the next thing."

Sam's proposal is a childish philosophy. Fill the hole in my heart by saying fuck it to everything else and taking more, and more, and more from the world until there's nothing left to take? Keep on grinding, and everything will be ok? Sure, whatever you say, Sam.

But... as childish as it is, there's an allure to her proposal. I picture myself having all the things in this world that I ever wanted. A bustling Guild, political power, tons of gold, beautiful women... if I had all these things and more, wouldn't I be better off?

Of course, I would. That’s a stupid question.

Sam's right. There's an entire Realm out there for the taking, and I'm here sitting on my ass, too depressed to be the one who does it.

"I got a question for you, Boss. What is it that you want more than anything else in the whole Realm?" The Princess asks, further stirring me to think on her proposal.

As I stare upwards into Sam's emerald eyes, I feel a churning sensation inside my heart taking hold of me. No longer do I feel like I'm on the edge of an abyss I can't crawl out of. This girl is now standing by my side and offering a hand to keep me from falling. Her words might be crass and her ideas simplistic, but they latch onto me in all the right ways.

With Sam's encouragement, I speak the words I've never had the courage to say until this very moment.

"I want to change. I want to move past all of my bullshit, to stop caring about what other people think, and to finally accept that I deserve to be as happy as anyone else." The words fall out of me like heavy stones cast into the ocean. They sink beneath the waves, and even if they surface again or wash back to shore, at least I made an effort to throw them out at all.

"That's a pretty good start, I think. We can work on it." Sam smiles down at me, her expression shifting from serious to supportive. She leads me on with her words, goading me to prove myself. "What else do you want out of life? What kept you going for so many years before you broke?"

I inhale sharply, tighten my fists, and summon my conviction. There's no other answer in my mind, so while staring right at the girl, I proclaim that childish dream of mine for the first time in ages, "I want to turn this place into the greatest Adventurer's Guild in all the Realm. Just like how it used to be."

"Just like how it used to be, or...?" Sam doesn't want me to settle for the low-hanging fruit so quickly, nudging me to grasp even higher. She's right. I shouldn't settle.

The fire inside me burns hotter still, and I correct myself. "Better than it used to be, damn it," I tell her, pleasing Sam to no end.

"There ya go!" Judging my words to be true and not just me saying what she wants to hear, the naked Princess becomes even more friendly and less domineering. Her smile widens, her eyes filling with pride over everything I've said. "That's a lot more like it, Boss. I knew you had it in you."

As much as I might feel good about myself, I recognize that this is all still a bunch of hot air on my behalf. "The struggle isn't over yet. I still have to prove I'm not just talking shit and that I mean it when I say I want to change." I say to Sam.

"You will," She nods her head at me, fully determined and sure of herself. "I know it."

I wonder why her confidence is so high when it comes to me bettering myself, so I ask, "Really? And how come you're so certain of that?"

"Because if you relapse, I'll kick your ass and put you right back on track the hard way if I have to." The strong warrior girl punches her open palm with the opposite fist, showcasing what will happen if I fall into my depression again. Usually, I wouldn't endorse such a violent treatment, but I feel it's just what I need in my specific case.

"I'm a lucky man to have you around, then." I smile up at her before finally becoming aware of Sam's nakedness once again. As we discussed such weighty topics, I grew distracted enough to ignore my attraction. That's no longer the case now that things have settled. I'm suddenly reminded of the burning hot lips of her pussy baring down against me.

Sam remembers, too. That playful smile of hers returns to her face as she says, "Now that you're not gonna care about stupid crap anymore, like worrying about other people's opinions of you, isn't there anything else ya want out of life? Maybe something a little more... short term? How about now... What do you want right now more than anything else?" Guiding my answer out of me, Sam rolls her hips a single time along my length, sending pleasure out for both of us.

I can't deny her any longer, and I don't care about any of the factors that make this 'wrong'. I want Sam, and I've wanted her since I first gazed upon the beautiful young warrior. Sure, she's only eighteen, and she's a Princess, at that. It would also be rushing things, I just met her today, and that's far from ordinary.

But at this exact moment, I just don't see why any of that matters anymore. They're excuses stopping me from moving forward with my life, and I will no longer be a slave to anything but my own desires and ambitions.

"There's a thing or two I can think of," I tell Sam, lifting my hips and driving myself into her pelvis. She bites her lower lip as my hardness willingly brushes up against her.

"That so?" Sam smirks, her cheeks turning a lovely shade of red as a small amount of embarrassment finally starts to work its way through her.

"Yes," Reaching out, I place my hand on the flat of the beautiful warrior's navel. Her flesh is so soft, so pure, and I feel like I could sink right into her. I run my fingertips down Sam's stomach and then around her hips, watching the chill of delight the girl experiences as they brush against her inner thigh. "I want to take out all the sexual frustration you've put me through today and fuck you like the little brat you are.

My declaration excites the girl. I watch as her eyes light up, and I feel it for myself when her lips twitch around my cock. In a low, husky voice, the tomboy asks me, "Then you know what to do, don't ya? It's time to man up and start doing what you want, Daddy..."

"Mmn," I don't even try to hide how turned on being called 'Daddy' makes me this time. I reward her for it by pushing more of myself up against her mound, and she grinds back down nice and hard in return.

At Sam's command, I... no, not because of her command. Because I want to, I sit up from underneath Sam and wrap my arms around the naked girl. She squeals excitedly as I pull her body close to mine and press our lips together in a passionate blaze of hot desire that's been building up from the moment we met.

Her lips are full, round, remarkably soft, and they taste faintly of the spicy cocktail I gave her hours ago. It's a delicious, fiery taste that suits her, and the explosiveness of the drink perfectly symbolizes our bombastic first kiss.

Neither of us holds anything back. After hardly any time has even passed, we're already sliding our tongues into each other's mouths. Since it's my first kiss, I know I'm not giving my best performance, but Sam doesn't say a word to tell me off otherwise. She's too wrapped up in having me all for herself.

The girl shows off her roughness. Her hands dig into the back of my shirt and into my skin with her nails. Sam does this while going hardcore on my tongue, thrusting her slick wetness down against my own and tracing every corner of my mouth with vigor. Sam's trying to figure out how to do this, too, but skill doesn't matter now.

Passion is the only thing that does, and both of us have that in spades.

Acting on my desires like this without a care in the world feels liberating to no end. There will be no more worrying, no more self-pity, no. Right now, there's nothing but the sweet, sweet victory tasted by sharing a kiss with my new lover.

Right or wrong, I want to fuck Sam with everything I've got. Once I'm done taking my pleasure from her, I'm going to un-fuck my life step by step to make sure that this Guild goes down in Karnalle's history.

Why?

Because from this point onwards, I'm going to do what I want.