Rise of the Guild Master

The Chapter with Emotional Milf Sex



Although Opalina is the third woman I’ve made love to in about just as many weeks, I’ll never get used to the amazing sensation of a girl accepting my manhood into her loving embrace.

The older woman squeals in delight as I burrow deeply inside of her eager, dripping pussy, her voice becoming a breathy mess by the time I bottom out and hit my cockhead against her deepest inner wall. 

Although she allowed me on top of her, the skilled healer is still very much the one in control as evident by the wrapping of her hands around my wrists shortly after I grab her by the hips.

We stare at each other there in the dark for just one short moment until she jerks my wrists forward. “You can move, Dear. Please... give me your dick. I need it...”

Her blush rises as I draw back from her tight tunnel up to my cockhead and in one fell motion I drive myself down once more even stronger. Opalina bites her lip in as she quivers in pleasure from my massive cock splitting her in half. “Is it everything you’ve dreamed of...?” I ask while mashing myself upwards into her sensitive clit.

“And... mmmn... and then some...” She reaches out with one hand and draws my neck forward, pulling me into another deep kiss. Our lips dwell sweetly on each other as I start pumping myself at a steady yet slow pace.

“You’re stretching me so wide...” Her purple eyes are full of haze and lust, and the more I thrust the more the curvy woman’s own hips start to grind against me. “I’ve never felt so full before in my life...” Opalina moans loudly, and her words do nothing but inflate my growing ego.

She motivates me to pick up the speed, so gritting my teeth I saw in and out of her clenching cunt, taking the time to thrust in every direction to explore the sensations of my new lover.

Her pussy isn’t the outright tightest I’ve had, but like the rest of Opalina being inside it makes me feel so warm and safe that I almost feel drunk from the unique sensation it wraps my cock in. Her lips tighten from time to time, sucking down and kissing my manhood in a delightful way that serves only to pull me deeper and deeper into her lovely slit.

As my pace increases, so too does the jiggling of her many curves. Most noticeably her heaving, heavy breasts still slathered in my semen. “Sweetheart... I’m not like the other girls you’ve had so far...” Opalina moans, trying her hardest to keep up eye contact despite the increasing pleasure between her thighs.

“I’m not a teen... and... mm... I’m not a petite little mage... you... fuuuuuck... I’m a woman. You don’t have to worry about breaking me...” grabbing hold of her bouncing mound in one hand, Opalina brings her flesh to her lips and in an effort to arouse me even further she starts taking long, slow licks up the side of her tit to lap up the delicious remaining cum leftover from my earlier explosion of lust.

“Fuck... me... HARD.” Opalina bites her lips while squeezing her perfect breast and it drives me mad. I can’t take it any longer, I need her. I’ve wanted this woman for as long as I can remember and now that I’m hers, I need to prove I’m worth the trouble.

So I fuck her hard.

Opal’s back arches and I wrap my arms around her torso, laying my weight down on her curvy body. Her legs criss cross around the back of my hips to lock me in place as I work up a feverish pace with my powerful cock. “Yes... YES!” She cries, her mouth forming a silent ring as moan after moan escapes.

In and out I pound my throbbing length into the older woman’s dripping snatch, each time a heavy wet slap ringing out as my balls smash up into her ass from this position.

Opalina has put me in a situation I’ve never been in before. With Sam, I was exploring someone else for the first time. With Zutiria I had experience, but she’s small and delicate and needed care. But with Opal I’m definitely the one with everything to lose. I feel an intense need to please her, to impress her...

While I don’t intend to inquire it’s clear that my partner has experience and I need to live up to her needs with more than just my size alone.

I need to make her remember the way I fucked her for the rest of her days.

My lips dive into her neck and she yelps as I give her a powerful hickey on her neck between thrusts of my cock. “So ROUGH!” Opal moans loudly, and I do it again. And again.

Every time I kiss her and leave a mark of my love she bucks her hip up the length of my manhood with such force it stings my hips in return. This intense and pleasurable reaction of hers motivates me to seek out more and more stimulation and more ways to fuck her.

Just how hard did she want me to go? I decide to push my limits.

I unwrap myself from our embrace while not letting up the pounding of my cock inside of her, and hold myself up with one hand on the bed. With my free hand, I cup her cheek and stare into her cloudy eyes.

“More...” She says in a husky, breathy tone. “MO-”

Before she can repeat herself I shove my thumb down into her mouth and her eyes widen from surprise. At first it almost seems like she’s about to gag, but she gets used to it faster than I expected. Her plump lips clamp down passionately around my thumb and she starts sucking it expertly with all the lavish attention she would give if it were my cock.

Her tongue swirls against me and I push it deeper, just testing what I can get away with. Opalina’s eyes roll backwards as I touch the back of her throat, and I call out to her amid frenzied thrusts of my hips, “You fucking like that...?”

“Mmmm... mhmmm!!” She nods her head while still sucking on my thumb, and the pleasure makes me gasp. To really throw her for a loop I even start pulling out of her wet mouth, her suction doing everything it can to keep me in place. But it doesn’t matter since I thrust it down back to her throat again anyway.

She becomes breathless and her pussy tightens around my shaft, overjoyed beyond belief at my rougher play. It felt almost as if her body itself was rewarding my aching cock for teasing her mouth.

When Opalina can’t take it any longer she opens up wide for air, and that’s when I grunt and put the entire force of my body into hard thrusts. “AH!” Her voice becomes raspy from her screams, and I can hardly manage to do anything other than ream her cunt like we were nothing but mindless animals.

I can tell she’s getting close so I use all the control I have to stop myself from blowing early and decide once more to test something out. “Cum for me...” I say, before slapping her gigantic breast.

“AH, GODS THAT’S SO GOOD!” The mature woman’s body jolts as if hit by lighting and that inviting look in her eyes begs me for more. I strike her titty again with my open palm and she cries and squeezes me between the lips of her pussy, becoming so tight I can barely pull myself from her tunnel.

“CUM FOR ME!” I repeat, this time instead of hitting her I grab her by the nipple and pull it out roughly as far as her impressive breasts will let her stretch.

“YESSS, I’M CUMMING I’M CUMMING I’M- HAAAAAA...!!” Opalina’s face seizes up and all my hard work pays off at once. Her body shakes. Her pussy convulses. Her hands pull me to her face to fill her empty mouth with my questing tongue and a torrential flood of her love juices squirt onto my cock like a fountain.

It’s too much for me to bear.

Tensing up my body and contorting my face into raging ecstasy, I cum directly inside of her needy cunt. Each spasm shoots another thick rope of my essence deep, deep into her clingy sex until my love spills out the sides of her labia and makes a sticky mess of our mashing crotches.

I sit there quivering inside of Opalina, reveling in the post-coital bliss I’m feeling by filling her up for the very first time. It’s such a lovely, intense feeling that is amplified when I reach my lips down to hers and kiss her.

It’s a soft kiss and it doesn’t last all that long, but the two of us are left smiling and giddy after its completion.

“Good boy.” Opalina proudly looks into my eyes and rubs my hair affectionately, her voice riddled with exhaustion and sounding even huskier than normal.

My body grows tired and I start to fall against her, but she embraces it and pulls me into a sweaty hug. Opalina smells of sex, and it causes a stirring in my still embedded cock. A stirring she notices very quickly.

Opalina rolls me over without any warning and in a flash it seems as if her weariness is all but gone. She now straddles my hips and is kneeled over with my manhood still inside her. “Sorry, Dear. But you’re not getting off that easy...” Her low, teasing voice lets out a slow and breathy laugh. “I said I was claiming YOU, didn’t I? I just let you have some fun.” She whips her gorgeous auburn hair out of her face and suddenly begins bouncing and grinding her hips on my cock.

“FUCK! I... I just came... I...!”

“And?” She gives me the look of a sadistic predator gazing down at prey already in its clutches.

I underestimated this older woman, and over the next round she proves it to me as hard as she can. 

She transforms from the subtle, gentle and encouraging type of older lady into a vicious queen cougar, impaling my rod inside her with reckless abandon and no regard for whether my poor body can take it. Given just how much sheer meat she has, she weighs heavily down on my hips and creates a powerful, impactful clap every time her ass drops down to take me.

Every last part of this beautiful woman jiggles intensely as she gives me the ride of my life. Her heavy thighs, her massive tits, her slight tummy, everything bounces and makes way from the heavy impact of our fucking.

Not wanting to let Opalina down, I do my best to buck my cock into her sensitive folds but this will be my fourth shot. While it’s true I’m blessed with some sort of divine stamina, it doesn’t extend to my body as a whole. Just because I CAN fuck endlessly all night doesn’t mean I should, especially when I’m all but being ravaged and devoured mercilessly by this savage seductress. My body is aching.

I’ve fucked Sam really, really hard before- but I was always in control. I’m not used to this... and it’s way... WAY too much.

“Is it too much for... mmm, for my little man...?” Giggling as usual, the healer licks her lips in pleasure.

“NO- I... I can still go... I can...”

“Shhhhh.” Opalina reaches her finger down to push against my lips. She smiles a sly smile and says, “Cum for Mommy.”

I don’t know how she did it, but at her exact words I slam upwards with all I’ve got and groan a gasping, guttural climax groan. My cum spills out no less violently the fourth time than the first, and her already flooded pussy gushes out my load so hard and loud that I can hear the wet sound of it rushing out of her.

Her eyes go white as I smash her pussy with unexpected, reactionary force and her hips lift a few extra inches off the ground. She almost falls over backwards in a powerful climax of her own before catching her balance by placing her hands on my knees.

I watch as Opal slowly rides my shaft, eagerly squeezing her muscles for me in an attempt to milk out every last drop of this load. As soon as she realizes the well has run dry, she finally rolls off of my body and plops off to my side.

Her breathing is ragged and deep. This took a lot more out of her than she was trying to make it seem... she’s not in the best of shape for her age, no matter how much I love her body facts are facts.

Turning to her, a warm smile brightens my typically somber face. “Was it worth... the wait?” I say between heaving breaths. 

Opal lays on her side and pulls me into a hug, from this angle I’m resting directly in her breasts. “No.” She says blankly, and for a moment I’m left with a broken heart. “You’re going to have to give me a lot more of that manly cock of yours to make up for the lost time, Dear.” She giggles and just like that my confidence is restored.

“If I can handle it, I’ve got two other girls on my plate too you know.”

“And you’re after even more? Sweetheart, you might want to start working on your stamina if you can’t even withstand a curvy old lady taking you for a ride.”

I raise my eyebrow at her. “I’ll have you know I can last a lot longer than this. You just wore out my BODY’s stamina... not my cock’s.”

There it is- that predatory glint in her eyes again. “Are you saying you’re ready for more?”

Shit. I yawn and nuzzle into her breasts and pretend to have fallen asleep. She laughs at my attempt and strokes my head. “Relax, I was only kidding. I’m good... for now. But I might wake you up in a few hours for some more fun.”

“I can live with that.” I say, muffled from between her tits.

“I don’t know if I can, honestly.” She sighs. “It’s a miracle I didn’t snap my back or tear a muscle. I’m not as young as I used to be.”

I roll my eyes. “I know how your aging magic works, Opal. You’ll be fine.”

She giggles that adorable little ‘fu fu fu’ laugh of hers, “Shush. I happen to enjoy pretending to be an old lady.”

I let out a contented sigh from my place in her chest and nuzzle to her even deeper.

For a short while we just lay there in each other’s arms, enjoying the feeling of being together. Eventually I feel the need to interrupt this quiet bliss because of a stirring in my ever-active mind. I need to know.

“What are things going to be like between us from now on?”

She’s quiet in response, but eventually says, “What do you mean?”

“Well... I mean how are you going to fit into my life? The girls really like you, and I know it’s a long ways away but I was maybe thinking that you could-”

“Shhhhhh.” She pets my head. “Things are going to be fine. You have your life, and I have my own to worry about. Somebody has to run this clinic.”

It’s not the answer I wanted, but it’s definitely the one I expected.

“We’ll go back to how things used to be. I’ll visit you a couple of times a week, only now it’ll be a sort of family get together between you, me and the girls. Only a hell of a lot kinkier.”

“Go on.”

She laughs me off dismissively, “Oh, shush... I will say one thing though, Dear. If you ever become successful enough that your Guild requires an in-house healer, well...”

Opalina pulls me out of her cleavage and up to her lips to give me the most intense and sweet kiss we’ve shared all night. “Consider this my application. Become a strong, successful Guild Master and I’ll be yours. Until then I’ll always be watching over you and supporting you from the sidelines. Understood?”

Was this her way of challenging me? Because if working my ass off and recruiting tons of adventurers to build my harem and my fortune means Opalina will become a permanent part of it, then... I can’t think of any greater motivation.

“Understood.”

Leaning over to kiss me on the forehead, Opal tenderly nuzzles into my face and praises me one last time for the night.

“Good boy.”


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