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Chapter 16 by Teeleh Teeleh

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Let the Guard Fuck You

You let out an audible sigh and nod your head compliantly.

“That’s the spirit,” the guard says, fidgeting with the cell lock.

The armored woman gives you a meaningful look as she locks the cell behind her. “I’ll kick the shit outta you if you try anything foolish, so don’t.”

You roll your eyes and nod again.

She strolls over to you and stands over your naked form. “Joshua, right? Or should I just call you meat?” She chuckles lightly as she begins doffing sections of her heavy armor.

You pout slightly at her aggressive tone. “Joshua would be preferable. And you? Got a name? Or should I simply refer to you as the ****?”

She snorts. “I much prefer the term opportunist, thank you very much. As for my name, you’ll have to earn that.”

You wait patiently as the woman removes pieces of her armor with practiced precision. After several long awaited minutes, the woman eventually strips down to her smallclothes.

She regards you for a moment with an amused expression. “Try not to drool, all right?”

You think to offer a rebuttal, but you are stopped in your tracks as the woman unceremoniously removes her beige cotton bra and tosses it across the room.

You are immediately enraptured by the sight of her voluptuous, bouncing breasts. The busty woman grins knowingly at your leering expression, and begins pinching and teasing her swollen red teats.

You feel your cock growing with needy arousal as you watch this woman’s sensual display. She notices you shifting uncomfortably as she erotically rubs her magnificent orbs. “I’ll show you mine if you show me yours…”

You bite your lip sheepishly at the thought of her incoming mockery. You can see the bulge in her panties; The guard’s cock is definitely larger than yours.

You’ve already committed to this, so you might as well just get it over with. You begin openly stroking your small penis on the floor in front of her.

“Aww, so cute. Joshua’s got himself a pretty little pecker.” She giggles playfully as she slides her beige panties to the floor, revealing a sizable, half-masted member.

She begins stroking herself with one hand and massaging her nipples with the other. “Like what you see, little man?”

You nod absent-mindedly as you slowly beat yourself off to the display.

She eagerly pushes you onto your back with her right foot. “I heard that the Mistress trained your ass the other day. She’s definitely bigger than I am, so you should have no trouble accommodating me.”

The woman firmly but carefully presses her foot against your cock in a show of dominance. “The Mistress may own your loyalty, but for the time being, I own this. Isn’t that so?”

You bob your head affirmatively as she confidently rubs the length of your cock with the sole of her foot.

“Mhm…mhmm…Yes mommy~~”

She leers at you. “Mommy, hmm? You want to play it like that?”

You look at her with embarrassment and shame. “Uhh, n-no, it just came out like that. I didn’t mean-”

“Shh…” She coos, manipulating your cock with her foot. “That’s alright, baby. Mommy is here. Are you gonna obey whatever mommy says?”

You nod eagerly.

“Good boy.” She kneels down in front of you and pushes you into a mating press position. “Hands up here, little man. Hold your legs behind your head.”

You obediently do as she demands.

“Mommy owns this as well, doesn’t she?” You grunt uncomfortably as she lines her thick cock up with your tight pucker.

You incline your head agreeably. “Yes, mommy. Please fill my slutty hole with your big, dominant dick.”

She nods with approval. Wasting little time, she spits a thick glob of saliva into your hole and lubricates the entrance.

The guard woman grips your mediocre member in her hand and begins pumping it as she slowly eases her cock into your anus.

In this strange sexual position, you find that you are particularly inclined to take every inch of her prodigious phallus. You moan like a whore as you feel her length bottom out in your ass. The guard withdraws halfway out of your anus, before thrusting herself forcefully into you once more.

She repeats this deliberately slow dicking for several repetitions, before giving your ass a thorough slap and intonating her new intent. “Time to pick up the pace, little man. You ready?”

You grimace in pain and arousal as you meet her gaze with resolute eyes. “Y-yes mommy. I’m ready.”

With only the slightest hint of acknowledgement, the guard then immediately begins penetrating you with revitalized vigor. Your eyes go wide as you feel her massive member swiftly and repeatedly gliding deep into the recesses of your anal cavity. The woman furiously strokes your small cock as she skillfully claims your ass with gusto.

You feel an orgasm starting to build within you as your insides are rearranged by the guard’s invading member. She continues to pound you relentlessly, her breasts bouncing bountifully up and down for your enjoyment.

The woman feels the lustful, incoming climax building in your loins. She bites her lip suggestively as she rails you like a two-bit whore. “Gonna cum already? Hmmff…Mommy really turns you on, huh? Hnnphf…that’s kinda hot. Go on, then. Don’t hold back on my account. Cum for mommy.”

She deftly massages your length in her hand, intentionally pushing you over the edge. Your eyes roll back in their sockets as you are rocked with an otherworldly orgasm. She angles your cute cock toward your stomach, and you ejaculate all over yourself.

The guard coos huskily as she manipulates your cummy cock in her hand. “Good boy. Mommy’s turn now.”

She picks up the pace, ravaging your anus at a breakneck speed. Your mind goes blank as you are fucked into the floor like an insensate slut. The woman uses your ass repeatedly for a number of uncountable, painful minutes before hitting her limit.

“Alright, baby boy. Mommy’s about to cum. I’m gonna fill your ass to the brim, you ready?

You bob your head idly in acknowledgment.

Your tongue lolls to the side as you buck your tiny penis wildly into her practiced palm. You feel a wild arousal course through your body as the guard woman hilts herself deep inside you.

She groans in orgasmic pleasure as she erupts, painting the walls of your innards with torrent after torrent of her thick seed.

Your body responds to the pleasurable **** in kind, and you feel your cock cumming for a second time.

As the woman presses herself into and slowly comes down from her orgasm, she notices that you ejaculated alongside her. “Mmm…did you cum again, baby boy?” She lightly rubs your jizz in her hand. “Mommy really knows how to make you feel good, huh…”

“Mhm…” You look up at her with submissive eyes as she slowly withdraws her burgeoning phallus from your ass.

The guard rubs her cummy secretions all over your thighs, and chuckles at the display. “You sure are a mess.” She gives your ass a loud *THWACK*.

You wince in pain but say nothing as you silently inspect your cum-coated body.

The woman stands to her feet and begins retrieving her clothing. “I don’t normally care for that sort of roleplay, but you’re a cute little guy, so how could I refuse?”

You manage to sit up and rally your resolve. “S-so, a deal is a deal. You owe me one, right?”

She shrugs, donning her bra and panties. “What, you mean that dicking I just gave you wasn’t adequate payment? You should be paying me…”

You frown at the guard as she starts to don her armor.

She gives you a wink. “I’m just fucking with you. Yes, I owe you one--within reason. I’ll check in on you periodically to see if you’re ready to cash in.”

You sigh in relief, and unapologetically watch as the beautiful crimson woman criminally covers her body with armor once more.

“So, about that name…? You ask with playful inquisitiveness.

She looks at you with skeptical eyes. “Do you think you earned it?”

“I think I showed you a good time.”

“It was adequate, I suppose.” She gives you a wink.

You offer her an unconvinced look. “Perhaps I ought to call in my favor, then.”

She raises her eyebrow at this. “For what, my name? Can’t say I’ve seen that one before.”

You shrug. “Well, if you won’t give it to me freely, then I see no other way forward.”

She stops armoring up and studies you for a moment. “That favor could get you out of a tight jam. Why waste it on such a superfluous whim?”

“Because I need friends in this place. People I can rely on.”

“Like Minerva?”

You feel struck by her sudden, verbal ****. While you remain earnestly loyal to the Mistress, you can’t help but feel shame for how that situation with Minerva went down.

You meet the guard’s gaze. “That was a mistake.”

She looks down at you disdainfully. “Yeah, it was.”

You sigh. “Look, I’m trying to balance loyalty with honor, all right? You try being the Mistress’s favorite pet. It's tougher than it looks.”

“Yes, I imagine it must be excruciating for you.” The woman begins donning her armor once more.

You pinch the bridge of your nose and collect your thoughts for a moment. “I won’t betray you. I learned from my mistake. What the Mistress doesn’t know won’t hurt her, right?”

The woman looks meaningfully at you for several uncomfortable seconds before nodding. “A shame you figured that out just now. Small comfort for Minerva.”

You look away, nodding your head slowly. “She was a friend of yours?”

“Something like that.”

You sit silently for several minutes in brooding resignation. Eventually the guard finishes armoring up and makes her way to the cell door.

“Keep your favor.”

You slowly look up at her.

“And clean yourself up. It’ll be hell for us both if the Mistress sees this mess.”

You bob your head slightly. “I will.”

The woman exits the cell and locks it behind her. She regards you contemplatively for several moments, before curtly breaking the silence. “It’s Persephone.”

You cock your head to the side in confusion.

She sighs, crossing her arms. “My name. It's Persephone.”

A wan smile crosses your face. “It was a pleasure to meet you, Persephone.”

“Just keep it to yourself, this time. If I wind up like Minerva, the Mistress will be the least of your worries in this place. Count on that.”

You dip your head agreeably. “I understand. See you soon?”

She tentatively nods. “Soon-ish. Try not to fuck anything else up between now and then.”

Persephone then unceremoniously begins striding down the dimly lit hallway.

You spend the better part of the next hour tidying up your cell and eagerly lapping up all of the evidence. You feel unbidden arousal swell through you as the taste of Persephone’s pungent spunk lingers on your tongue.

It seems that you have made a new ally. You can’t say that you’re fond of the subterfuge, but you can be loyal to the Mistress and maintain additional friendships, right?

You recline on the stone floor of your cell and contemplate how to handle the Mistress moving forward. Lesson four is coming up soon, so you’d best prepare for it.

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