Rise of the Guild Master

Chapter 119: Healing Sex with My Princess


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Sam presses her lips against mine and her hands begin rubbing my shoulders through my clothes.

Because of her strength it feels phenomenal and she’s able to get all sorts of knots out that desperately needed attention. Thanks to constant deskwork I accrue a lot of them, so even now there’s plenty for Sam to work through despite getting a massage from Opalina’s yesterday.

The pressure is so intense as she works my neck with her fingers that I make many sounds that could be interpreted as lewd, yet Sam doesn’t say a word.

She stops herself from teasing me, smirking, or making any inappropriate comments. Seeing the crude Princess be so serious and unlike her normal self is astonishing, and it humbles me knowing how much Sam wants to be perfect for me in every way that she can.

It’s true that because she’s the youngest woman in my life, I probably write her off as a kid at times even when I don’t mean to... mostly because of her personality and her impulsiveness. But there’s so more to her than just that.

I need to remind myself that more often, even if she has trouble showing it.

“Pants.” Sam commands, and I follow her lead in lifting our hips off the couch for a brief moment to slide our pants halfway down.

I’m hard, but it’s not enough for Sam.

My lover begins to slowly grind the mounds of her pelvis against me with only the thin fabric of her panties separating our bare skin. It’s not her typical feverish rubbing but a romantic and lovingly paced attempt to bring me to my full length. She moans softly from the contact but does her best to look down on me with a mature, concerned expression on her face. 

It’s more than enough to make me swell with need, and Sam’s wetness grows more apparent as well. The once dry panties now drag her soaked slit along the length of my naked cock and she begins to pant and moan. “You deserve this, Daddy...” Sam whispers sexily into my ear.

“Don’t let stress defeat you... you’re stronger than that... It’ll... all be... mmm... ok... Ah!” The Princess smirks out of nowhere, a glimmer of her playfulness coming out of hiding. “I got an idea.”

Sam briefly stops what she’s doing and reaches inside of her thick leather top with both hands, quickly undoing her bra and dropping it onto the office floor behind her.

“Here we go-” She lifts the bottom of her shirt up over my head and pulls it down, covering me in darkness and pressing her naked breasts into my face for the second time today. We were out and about today, so there’s a distinct smell of her ripe sweat pervading from the leather top.

It’s like a slice of delicious heaven.

“Sam...”

I wrap my arms around her waist and pull her closer to me.

“You can stay in there as long as you need. You don’t gotta come out if you don’t wanna.” My lover giggles and she resumes grinding on my increasingly needy cock.

“When my friend goes inside can he stay as long as he wants, too?” I shift my hips upward, poking the head of my shaft against her feminine lips through the wet, hot and sticky panties barely covering the sweet hole that oozes in want of me.

“Absolutely.” Lifting her hips up ever so slightly, Sam pulls her sopping panties to the side and wastes no time dropping her tight pussy down on my cock inch by pleasurable inch in a slow, comforting way.

We both share a steamy moan of satisfaction quickly made greater by the Princess when she starts rocking her hips right back up and slowly back down. Up and down. Sam hugs my head to her chest, squishing both of her bountiful breasts into my face for my enjoyment. I reward her by beginning to kiss her sensitive flesh, and she sighs contentedly in response.

“Do you want to... mmm... just take the rest of the day off...?” Sam asks while lovingly sliding my long manhood fully into its home and clenching. “You don’t HAVE to tell us about the... the Bond Level junk...”

As I nuzzle up to her bouncy tits from inside the darkness of her shirt, I nod my head and say, “It would be better to just approach it tomorrow with a clear head. You’re right. I’m putting too much pressure on myself...”

“You always are, Daddy. Too much stress’ll kill you... we gotta make sure you let it all out before it’s too late... we both know you have a LOT of stress to work through. I’ll do my best to squeeze it alllll out...” Sam laughs in a low, gentle tone as she starts to more seriously pump her hips down onto my bare lap, smacking the bare cheeks of her ass repeatedly down against my naked thighs.

I feel safe, comfortable and content. Not unlike I do when I make love to Opal, but in a different way. Sam grounds me and helps me focus on the moment just like she always has, and I know I can rely on her when I need someone.

Wanting to show my appreciation for her, I start by digging my hands into her bouncing butt and help it glide me in and out of her loving pussy seamlessly. Every bump and fold of her tunnel constricts and convulses around me, overjoying my cock and enveloping it with warm, wet affection.

“I love you, Daddy...” Sam says as she holds my head inside her shirt.

“I love you too, Sam... so much...” I tell her the truth.

“Mmmm... keep going...”

“I love you, Princess. You’re the best...”

“More...”

“None of this would be possible without you... you changed me, Sam... and you’ve brought me so much... joy... and...”

“A-And...?”

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“And pleasure...” My hips thrust upwards roughly at the correct moment to emphasize my point, angling it so that the head of my cock scrapes up against one of her favorite spots and makes her squirm.

“Mmmmm!” She bites her lips and closes her eyes. “Don’t get ahead... of yourself...” Sam pants and begins slapping herself harder and harder down onto my cock but making sure to keep it restricted to slow, forceful thrusts. “I’m the one taking care of you, here...”

As much as I love her like this, being submissive to her doesn’t come as naturally to me as it does when with Opal. Ironically it makes me want to act a bit like Sam herself, cheeky and naughty... perhaps even a little bratty.

“Are you sure you can handle it? I have... ngh... a LOT of stress...” I tease and thrust up between the tight, drooling lips of her wetness right after she slides me out.

“MN-” Sam grunts and fights back by smashing down her hips so hard that it pushes me right into the couch below.

“Don’t make me angry, Daddy. You couldn’t handle it...” She giggles amid pleasured moans.

I can’t believe I’ve never imagined it, but thoughts of angry sex with Sam cross my mind. Dear Gods, she would absolutely destroy my pelvis if she ever used her full strength...

“AH-” Sam’s eyes roll backwards and she grits her teeth, “You... just got even harder... you’re such a fucking perv... mnnn- it’s... rubbing so many good spots...” 

My hands help her start to fuck me a little bit faster, and this time she doesn’t complain. Especially when I start sucking on her nipple. “Heh... you didn’t get enough of my titties this morning, huh...?”

“Even if I lived a thousand lifetimes, Sam, I could never get enough of them...”

She blushes, unused to more overtly romantic lines during sex. We don’t usually get this feelsy so it’s cute seeing her reaction. Usually it’s just dirty talk to accompany rougher play and spur me to greater action, but it’s different between us at this moment in time. Sam not only confessed to me but fully intends to eventually face her family one day so that we can even get married...

What would such a ceremony even be like? By the time it even happens how many brides are going to be there waiting for me at the end of the aisle?

It doesn’t matter. Right now, the only important thing is that Sam will be the first of them. It’s her right.

And I always give my Princess what she wants, no matter what it is.

“Sam... I’m... getting close...”

“I know... it’s ok... do it... fill my body up with your love, Daddy...”

Never one to disappoint, I no longer hold myself back and start thrusting roughly into her trembling pussy like there’s no tomorrow. My lips kiss, suck and bite her pink nipple with each and every thrust and it isn’t long before my Princess starts having a trembling orgasm against the powerful hardness I pound into her repeatedly.

She cries loudly, so loud that everyone in the Guild has to know what we’re doing now if they didn’t already.

That’s ok. I want them to hear me fuck this beautiful, young girl I love with all my heart.

I scream as my climax explodes out of me, intent on making sure they all hear how much pleasure she’s able to give me. Even though muffled against her tits and from within her leather top, I’m still loud enough in my ecstasy that there’s no way they can’t hear me while I’m cumming inside of Sam like a broken fountain.

Together we ride out the duration of our shared orgasm and once it finally draws to a close we both sit there upright in each other’s arms, my burning cum dripping out of Sam’s snug tunnel and down the sides of my half erect cock.

Eventually, Sam stretches the top of her shirt over my head so that we can both poke out. She’s grinning ear to ear and the warm sight of her youthful smile washes away any lingering stress I might’ve had leftover.

“Feel better?” She asks in a low, quiet voice.

“Almost-” I press my lips to her and steal a lengthy kiss. “...There. That’ll do it.”

Sam blushes, laughs, nuzzles her nose up against me and we just sit there quietly for a moment enjoying the feeling of mutual peace.

“Question.” I break the silence and Sam tilts her head.

“Yeah?”

“Probably would be a bad idea to have the kitties clean up the couch, yeah?”

Sam snorts in that goofy, boyish way of hers that drives me mad and shakes her head. “Gods, yeah.”

We laugh in each other’s arms and spend a good while just sitting there in my office, alone except for each other.

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