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Rise of the Guild Master

The Guild Master of Dewhurst has had a rough life. After many years of failure he rises to face his destiny and transform his decrepit Adventurer's Guild into the greatest Guild in all the realms. How? By filling it up with cute female adventurers who get powered up from making love to him, of course. Using nothing but his massive intellect, a sharp sense for business, a pair of magic eyes and a dick blessed by the Goddess herself, he'll transform a growing harem of misfits warriors into a team strong enough to defeat the Demon Lord... If the over the top town of Dewhurst doesn't kill them first, that is.

PunishedKom · Fantasia
Classificações insuficientes
256 Chs

Being a Good Boy

Waiting for Opal in her bedroom felt like the longest ten minutes of my life. I was naked as could be and my cock was painfully erect the entire duration. In a way I felt out of place laying atop the blankets of this luxurious four poster bed with satin curtains. This room, and the bed specifically smelled deeply of a mature woman and here I was in the nude, tainting it with my perversion.

It's a silly thought, sure, but I'm buzzed and very nervous about what's about to happen. I just received a very harsh, stern verbal beating that I entirely deserved from a woman I love from the bottom of my heart and then I was told to strip myself and await her company.

I won't apologize, it wouldn't be enough. Everything she said was true. Within the tangled web of relationships I'm weaving I'm definitely the one looking after Sam and Zutiria and there's no one looking after me. Not in the way that I need someone to. Or rather, there always was and I spent most of my adult life isolating her.

I can't say I'm sorry. I can only be better.

There's a knock at the door. It's slow and meaningful, and followed by the low tones of Opalina's voice. "I'm coming in."

I appreciate the warning, even if it's completely unnecessary. This is her bedroom after all...

Opalina emerges, having made her third second wardrobe change of the night. This time she wears a dark, deep blueberry colored robe with white fur trimming and lots of lace. It covers the entirety of her body, though hugging it tightly in all the right places. While not explicitly lingerie, it's very, very close.

Glaring down at me with a look of seriousness, Opalina approaches her bed in the darkness lit only by the flickering of scented candles spread about her bedroom. "Are you going to be a good boy from now on?" She asks.

"I don't know." I admit fully.

She raises an eyebrow and crosses her arms. "Explain yourself."

"I'm not used to having to rely on anyone else. I want you to be with me so that when I make a mistake, you can scold me and put me back on the right path. I can't promise to be something that I don't know how to be. But I can promise I'll try if it means I'll have you in my life."

There is, for the last time of the evening, a long and pronounced silence. Only this time at the end of it Opalina smiles in a pure, motherly manner and opens her robe in all its glory. "A very good answer from a very good boy." She says.

The blueberry robe falls to the floor and I'm stunned by what was hiding beneath.

Standing 6'2, Opalina's body is not thin by any stretch of the word. She has endless curves, she has a tummy, and her thighs atop her long, long legs are so meaty they all but clap together as she walks... and I have long since emphasized the sheer wonder of her breasts. She is a striking, classically beautiful woman the likes of which you see illustrated in ancient history books and sculptures inspired by the gods themselves.

Making her even more beautiful is her long and wavy auburn hair that falls along her back perfectly even now, stopping just shy of her generous ass. Her glasses are nowhere to be seen, leaving me alone with the deep, purple comfort of her eyes.

And if all that natural beauty wasn't enough, underneath the robe Opalina was hiding a devilish secret. Gone were her traditional pantyhose and skirt, instead replaced by sheer white stockings digging harshly into her plush thigh meat. A lacy, dream-like pattern flows across them and the both of them attach via white leather straps to an equally lavish white garter belt wrapped oh so tightly around her hips. If she had any more curves to give her entire ensemble looks like it would pop right off. Granted, it's far from the only thing that's about to pop.

Beneath the garter belt she wears absolutely nothing. I can see her mound, wet and eager for me even though we've yet to even touch outside of our kiss. Above her cleft is a humble little bush of auburn, trimmed tastefully. It truly made her seem much that more mature than my other lovers, although I love them all.

Last, but certainly not least, the tits I've dreamed of for so long now sit out in the open for me to see in their full resplendence. Her skin has the slightest olive tan to it, but despite that the only word I can use to describe her massive globes of breasts is creamy. So big and so smooth that it looks like I could drown in them and sink into their depths. Her dark pink nipples look so sweet and inviting, calling on me to take them.

I feel like a child again, looking up at such a perfect and mature woman and feeling small, vulnerable compared to her.

"You're so beautiful..."

Smiling, she sits down on the bed. "And so are you, my precious little man. Come here." She pats down on the meat of her thighs. "Come, come. Don't be shy."

I do as I'm told and scoot from my place on the center of the bed down to her thighs and lay atop them, mirroring the situation we were in just earlier in the night, only now with a much more intimate undertone.

"Good boy..." She smiles, reaching down to massage my scalp with her deceptively powerful fingers. "What a gooooood, good boy you are..."

"Is it.. Normal for those two little words to feel this good...?" I clench my eyes from an intense and emotional satisfaction the likes of which I haven't felt before.

"What even is normal, Dear? If the words 'good boy' make you happy then why would you ever get hung up on something so banal as normality? Is someone going to judge you for your tastes? Here? When you're alone in a room with a woman who would give you the world if you asked it of her?"

"Mmmm..."

"My poor little man needs to stop worrying and using his brain so much, even though I know that's what he's best at. Always such a smart little boy..." Her gentle voice coos and fawns over me, swimming into my ears and sending a shiver running through me with each and every word. "MY smart little boy..." She giggles softly with pride.

"Look up at me, Sweetheart." Opal commands of me.

"Yes." Opening my eyes I can very clearly can't see past her heavy breasts.

"Look at them. What do you see?"

"The biggest breasts in all the realms."

It's hard for her to contain herself with that one, but she does her best to stifle the laughter all the same. "Probably not, but they're all for you. How long have you waited for this moment, Dear?"

I blush as I'm compelled to answer. "Ever since my first erection." It's incredibly embarrassing to admit, but I do it regardless.

Opal leans over, her right hand placing itself on my pecs as it slowly starts to travel down south. Meanwhile, her tits start to spill down closer and closer to my face. "I think such patience deserves a reward. What does my sweet little man want? Go on, tell me."

"I want to suck Mommy's tits so bad, so very, very bad..." My hips buck at the thought and she laughs. Not in a mean, judgmental way, but in sincere amusement at my perceived cuteness.

"Go on, Sweetie. Help yourself." Opal lowers her delicate pink nipple into my mouth while grabbing my aching cock in her hand at the same time. I moan into her hard, pink pebble as I suck on her bosom for the first time.

"Mmmm... I've wanted you to do that for so, so long... Just as I've wanted to do this." The mature woman delights herself by stroking her skilled and gentle hand up along the length of my sensitive manhood in a slow, teasing manner.

"That said, I didn't take you for the type to get a tattoo... at least not in such a delicate place."

"What? Oh, no... that's... a rune Zutiria placed on me. It's so I fit inside of her." I blush upon explaining an odd highlight sex life to my newest partner.

"How interesting. I don't know the first thing about that sort of magic." She laughs in a low, sultry moan. From the look in her eyes I can see Opalina imagining my thick, towering meat pounding itself forcefully into the little Mage's tiny hole.

It only arouses her further.

Her fingers are deliberate and never do more than softly caress my shaft. From balls to tip she brushes against me with her nails in between full strokes. This rhythm of teasing is so caring and nurturing, unlike any handjob I've had before.

As she starts to put more force into it by squeezing the base of my cock and milking upwards, my breathing grows even heavier and in a reflexive panic I moan and bite down on the tender nipple.

"MN-" Opalina's eyes flicker and she bites her lip. "Gentler, Dear... gentler. I don't know how you're treating those girls of yours, but you need to be tender with a woman... unless she asks you otherwise." A slow, thoughtful laugh bellows out from her chest making her heavy tits jiggle.

For just a moment I leave her nipple and take a breath of air, looking up at the beautiful, curvy goddess. "I'm sorry..."

Her reassuring smile that I can barely see peeking over her breasts comforts me instantly. "Don't be sorry, Sweetheart... Just be better. That's all Mommy could ever ask of you... Ok?" Opalina emphasizes her point by squeezing my cock and rubbing upwards once more, slowly and tightly.

Stifling a moan, I nod my head. "Yes... yes, I'll be the best I can for you...!"

My sweet, auburn-haired doctor licks her lips and begins stroking my hair from her lap with her left hand. "That's a good boy... a very, very good boy. Now be a dear and don't be shy, I said you can help yourself to my breasts, yet you're being so reserved and holding yourself back. Just remember, love... be gentle. Be kind. Show them how much you love them."

I waste no time following Opalina's instructions and I immediately wrap my lips around her proffered pink nipple and suck down sweetly on it and the surrounding areola. She hums in response out of pleasure, while with my hand I finally sink my grip into the heavenly mound of her right tit.

It's softer, squishier and fatter than any breast I've yet felt, and while Sam is plenty stacked the Doctor's assets are at the very least twice as big. Rather than sticking out like a sore thumb, however, when on the body of a curvy and mature goddess such as Opalina they seem natural and perfect. I never dreamed they would be offered like this to me on a silver platter, but I always hoped.

Caressing and massaging the creamy flesh of her right breast with my hand and lapping, swirling and teasing my tongue around her left nipple at the same time, Opalina's arousal grows and I feel her thighs shift and grind purposefully into each other under my head.

She rewards me by increasing the affection her playful hand gifts my cock. She transitions from slow, purposeful rubbing to a deeper and more intense cock massage by gripping down and pumping up and down. Opalina pauses every so often to skillfully tease my tip or fondle my balls exactly when I want them to be.

"Mmmmm..." She closes her eyes and rolls her head back. "This is the biggest, hardest, manliest cock I've ever seen... I'm so proud of you, my sweet, sweet little man."

'You're welcome for that one, bee-tee-dubs. I thought it'd help get you on the right track. Maybe I'll make it bigger again later, too.' The unseen Goddess sees fit to interrupt the passionate atmosphere built between us by planting her words into my mind. I don't respond, but Opalina immediately notices my distraction.

"Sweetheart?" She looks down at me over her tits, concerned.

"Sorry..." I pull from her nipple, leaving a small trail of drool connecting her to my lips. "It's just... you're so good..." Moaning deeply and arching my back, Opalina seems convinced well enough and she giggles proudly of her own skill.

"It's ok, Dear. Just enjoy it. Do you want to cum for Mommy?"

"Yessss..." I barely manage to squeak out since as soon as she says it she starts wringing my cock.

"Good." Up and down, up and down Opal squeezes with a focus and purpose in mind. "Do you like this?"

I nod, now unable to say anything beyond my increasing groans.

"Mmm, you're so cute. Stop holding back for me. Your girls have told me all sorts of things about you, you know..." She laughs, a slight look of curiosity twinkling in her eye. "I really, REALLY want you to cum for me, Sweetheart... please... please cum."

She pumps harder, slapping her fist against my pelvic mound with every heavy thrust.

"Be a good boy... please... cum..."

Opalina moans loudly for my enjoyment, and wrapping her fingers and thumb in a tight ring she wrings the one last passionate time it takes to push me over the precipice.

The boiling desire in my balls to unload at her touch finally bursts outwards, spewing an unnatural and powerful cannon's volley of my white hot load into the air. Rope after rope flies and falls down, coating her hand and plastering my pelvis so heavily that it pools down the sides of my hips and trails down onto the luxurious bed below.

Her skillful hand keeps milking and milking every drop of my load, her voice encouraging me by moaning and making soft little noises of amazement.

This continues on for at least a minute straight until my ropes finally recede and I'm left a shaking, trembling mess from the best handjob of my life.

Now that she's done nursing my orgasm, Opalina surprises me by dropping the sultry and mature air of experience and addresses me honestly. "Sweetheart? Honest question. Not as your lover, but as your doctor."

"Yes...?" I shift off of her lap so I can better see her face, even though I desperately want to lay on her thighs for the rest of my life.

"You're aware that this amount of semen is... ah... medically speaking, absolutely fucking ridiculous, right?"

I can't help but laugh as she loses her air of authority. "Yes, I had a feeling but it's good to have a medical professional offer a second opinion."

Opal smirks at my coy response. "How does little Zuzu even handle such a massive load...?"

"She doesn't, but thankfully the sheets are there to absorb what she can't." I shyly look away, laughing under my breath.

"The girls told me it won't take you long to recover in between shots, is that correct?" She smiles hungrily at me and then scoops up a large stroke of my semen and deliberately laps it up like the sweetest of creams. Opalina is very careful not to avoid eye contact as her tongue licks more and more of my load into her mouth and swallows every drop.

"Yes... usually under two minutes... depending..." My pulse rises as I watch the unfolding show. Soon, after licking her coated hand completely clean, Opalina decides that scooping up my cum isn't practical enough for her and she scoots down to my crotch.

"Depending...?" Her husky voice utters and her purple, lusty eyes size me up with seduction from behind my cock. Then, Opalina opens her pillowy lips and droops out her tongue to start licking up every last inch of my thighs and hips for stray cum. Her voice produces breathy moans with every last taste she gets of me intended to drive me mad with desire.

I feel her warm, wet muscle explore my pelvis as it teasingly laps up every part of me that isn't my penis. This deliberate denial only makes me moan and roll my head back into the soft sheets below. Needless to say I'm harder than iron in no time at all, but she doesn't stop until I'm well and fully clean.

"Mmm, looks like I figured out how it works on my own." She giggles playfully. "But maybe Mommy should make your cock even harder before she finally lets you inside of her, hm? What does my sweet, sweet little man think of that idea?"

The thought produces a tiny whimper that I can't control. I meet her gaze and panting heavily, I manage to tell her, "I want whatever Mommy wants. She knows what's best for me..."

The sparkling delight in her eyes is plain for me to see, and her rosy cheeks flare with even more fiery passion. "Mmmm. Such a good boy."

"I really... REALLY like it when you call me that..." I groan, my cock throbbing in need of her attention.

She giggles and without saying a word, sits up and picks me up by the hips so that my ass rests on her thighs. I feel the plush softness of not only her supple meat, but the lacy lingerie pressed up against me. Her plan is obvious, and if I was throbbing before... now? Now my cock was thirsting like a madman.

"Of course you like it. You've always been my good boy." And with that, Opalina hunches over ever so slightly to wrap my cock in her gigantic tits. The contact with her soft, creamy flesh alone is enough for me to clench my eyes and arch up into her, begging the mature woman to fuck me with them. Now I know why she avoided licking up my cock, as my semen still clung to it and my upwards thrust lubed the way slick and easily enough for the tip of my cock to poke out the tip of her oversized cleavage. She put some real thought into this...

"My goodness...!" She coos in a low, exaggerated tone. "My sweet little man is so huge that even with tits like mine, you still pop out! That makes Mommy so hot... and so very, very wet..."

"Haaaah..." I look like an idiot. I'm melting and becoming putty, and again I buck up into her massive titties for all I'm worth.

"My, my... just can't wait, can you?" She giggles and takes both of her arms, wrapping them around her enormous boobs and constricting me. The squishy prison expands at her touch and makes seeing my tip impossible. "That's ok, Dear. I think you deserve to be spoiled a little."

And with that she flutters her long eyelashes seductively and licks her lips, before finally starting to hump the entire length of my cock with her incredible, plush globes.

"Ahhhh," She rolls her eyes back. "You're... mmm... a lucky boy, you know? Not... mn... every woman feels good from this... but... my huge tits are so very... very sensitive..." At the drop of her last word she glides me out of her cleavage and slaps down so hard that the meaty smack of her tits actually echoes out into her bedroom.

"AH, OPAL!!" I've had a titfuck from Sam before. I loved it, and I love Sam with the bottom of my heart, but this is an entirely different experience. The sheer pressure and softness of her fat chest fucking me and the entirety of my cock is something I never could have imagined. My hips buck and my hands clench the sheets below as I watch this thick, stacked beautiful woman make me putty between her bosom.

As I call her name she bites her lips. "This... this isn't gooood." Her breathy voice moans just a tiny bit. "I just wanted to make you harder for me, Dear... but... oh... I can't help myself... do you want to cum in my tits, Sweetheart...?"

My jaw falls wide and I buck my hips even harder upwards into her, loudly I cry, "Oh gods yes please please PLEASE let me creampie your tits...! Opal... OPAL!!"

The words light a fire in her as she closes her eyes and squeezes her mountainous mounds even further around my desperate manhood until she's created such a soft, pillowy tunnel for me to fuck as possible. "Give it to me... Dear... I want it so bad... fuck my tits and cum in them... it's all you, I believe in you... Fuck them harder... HARDER-"

She gasps as I groan, starting to put everything I have into fucking her titties and making them jiggle uncontrollably from the power of my strokes. Again and again and again I hammer my cock inside her breasts, watching her face contort into that of a woman on the verge of a powerful climax.

With a look like that, I can't hold back. I fuck her tits with all the force of the many, many years I've longed to do this very thing. When I can no longer hold myself back I scream, "OPAL!!" out into the darkened, candlelit room and begin cumming such a thick, powerful load that it makes my first blast look like child's play in comparison. A handjob just doesn't compare to getting to fuck the biggest tits I've ever seen, after all.

Opalina herself screams as well, digging her fingers so hard into her sensitive breasts they leave a mark. From the way her body's shaking I can see that she's riding an incredibly powerful orgasm as my cum erupts out from between her lusciously large mounds like a burning volcano of my manly seed.

Even as I cum I keep bucking and bucking, using her tits to milk me for everything I have to give until she's slathered in so much of my semen that it blankets her chest and creates a warm, gooey pool in her cleavage.

After I'm done cumming, somehow it's just not enough. I didn't even lose my hardness this time, which happens now and again, but it's far from normal even with my 'divine enhancements'.

Opalina, still reeling from cumming from her sensitive tits, is in the same position. She wants more, and she wants it now.

She lays back properly down the center of her elegant four poster bed, leaving a massive trail of cum from her swaying tits as she does so. She spreads her legs and the sweet fragrance of her womanhood fills the air, and it's only now that I see how seeping and wet she is down there.

Presenting her pussy to me for the first time, she looks at where she left me and using her fingers my beloved doctor splits her puffy lips wide open to expose her tight, pink hole for me.

"Dear... it's time. All those years you made me wait for you... make sure it was worth it... understood?"

I sit up fully erect in more ways than one and kneel between her legs. Fist around my cock tightly, I line it up with her needy slit and begin to slowly push my head against her welcoming entrance.

"It will be." With those three words of promise I take a deep breath and thrust my everything into the dripping sweetness of my newest, yet paradoxically oldest, love for the first time.

I am so sorry for forgetting to upload this one, this chapter comes before 'The Chapter with Emotional Milf Sex' and is the foreplay. - Follow me on Twitter @PunishedKomics for lots of art of my characters and updates!

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