Jack of All Trades Ch. 01

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Jack meets the Mayor and reunites with his mature lover.
8.9k words
4.49
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Part 1 of the 2 part series

Updated 12/11/2023
Created 12/08/2023
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Chapter 1

A scowl descends upon my face as I analyze the predicament that has presented itself to me. Before my feet lies the main drag of what remains of Owosso, Michigan: a relatively small pre-disaster city which is now home to the relatively small post-disaster city/settlement run by the self-appointed Duke Wellbring. The Duke is a conceited man, his ego a ticking time bomb of self-destruction that has only temporarily gained him the power that he had surely always craved prior to the apocalypse.

For this reason, I am amazed that such a man would have reached out to me for assistance. His message to me arrived via the radio just this morning, urging me to hasten to the settlement for urgent repairs. A man such as the Duke would surely not have contacted an outsider such as myself without good reason. Perhaps his favorite toilet has backed up.

I sigh with exasperation and cast my gaze toward the settlement gates, which are two massive steel doors laden with barbed wire that span the entire length of the street. It's unlikely that they would be willing to open such a gate for only one visitor. I produce a map from my backpack and check my location once again. Sure enough, the entrance indicated by the radio message this morning lies directly in front of me. A snarl startles me from my concentration, and I turn to find a male zombie shuffling toward me from deeper within the alleyway in which I am currently taking shelter. Looking past him, I see that a pile of garbage appears to have been strewn about, indicating that he had been hibernating beneath the refuse when my scent awakened him. No wonder I hadn't seen him. You won't catch me digging through piles of trash in every hiding spot just to make sure there's no zombies tucked inside them.

Measuring my steps carefully, I dodge around behind the zombie and walk deeper into the shadows of the alleyway, luring him away from the street so I can dispatch him without arousing attention from his compatriots. As he stumbles closer, one of his arms detaches from its socket and plops onto the ground, nearly forcing me into a fit of laughter. I draw him in until he's out of the sunlight and remove his other arm with my machete, before decapitating him in one large sweep of my blade. His neck hangs onto the body by a scrap of flesh, but I can see that the brainstem has been severed, rendering the undead man truly lifeless. I kick the severed arms out of the way as I return to the entrance of the alleyway and swap my machete for the longer ranged pike that is held on my back. The pike is fashioned from a simple metal pipe with a long bowie knife blade welded to the end of it. I unwrap the protective cloth from the blade tip and stuff the cloth into my backpack before entering the street and making my way toward the gates.

My eyes dart back and forth across the street, watching intently for any large movement or disturbance as I creep down the center of the street toward the settlement. A novice would have attempted to stick closer to the side of the street, hoping not to draw too much attention, but anyone with even a day's worth of experience prowling outside settlement walls knows that leaving yourself as much room as possible to flee in any direction is more valuable than any type of cover. A zombie could easily lunge out from behind a shrub and bite you before you even know you've been detected.

A female zombie with no eyes seems to pick up my scent and begins trudging along behind me, her arms stretched out in front of her searching desperately for the delicious living flesh that she can smell so close to herself. I can see a line of drool slithering its way down her rotten neck as she follows me closely. I allow her to approach me slowly, backing toward the gates, until she's within reach of my pike, and I drive the blade directly into her head. The zombie slumps to the ground, and I continue on my path toward safety.

Now that I'm closer to the gates, I can see a smaller door has been set into the far-left side of the gate, and a pair of eyes is watching me intently through a peephole as I draw closer. I pick up my pace and head directly for the door, fending off two more stragglers before finally arriving at my destination.

Before I have a chance to introduce myself, the figure behind the door speaks first. Her voice is quiet and soft. "Are you Jack?"

"Jack of all trades and zombie exterminator at your service, miss." I keep my eyes on a swivel in case any zombies decide to throw a surprise party for me. "The Duke sent a message through the radio this morning. Said something needed fixing urgently."

I listen as what sounds like a very sturdy metal brace is removed from the door and it swings open, revealing the girl who would be my first encounter with the people of Owosso Settlement. She's short and rather thin, a little too skinny for my tastes, but with a face cuter than a mouse's. She moves aside so that I can enter the compound, and I see that she has a revolver hung on her hip.

"Nice piece." I say, gesturing to the gun. "Revolvers are very reliable weapons outside the walls, though usually much too loud to be of any practical use."

She fondles the wooden handle and blushes a little bit. "Gift from my pops. Never used it before."

"Well, keep her oiled up and clean and she'll still shoot when the time comes." I finally take my eyes off the girl and observe my surroundings. The settlement stretches about 5000 feet of the main street, with all the buildings on either side of the street converted to housing and useful facilities such as storage, an armory, and bathhouse. The other end of the street is blocked off by an impassable 20-foot-high steel barricade, lined with even more barbed wire. I suspect that all the back sides of the buildings have been similarly barricaded or sealed shut to prevent entrance from any location aside from the main gate. The asphalt along the middle of the street has been completely removed and converted into rows of gardens, which the settlers appear to be working together to cultivate. At a glance, I can see tomato, carrots, onions, lettuce, green beans, and various types of peppers laid out neatly in rows. A small group of people are currently using 5-gallon buckets to sprinkle water across the plants, taking care not to trample any of them. Many others are wandering about the open street, conversing and heading from one building to the next, some carrying boxes or baskets of laundry, others simply strolling with a friend or relative.

I'm truly impressed. I hadn't known that Owosso Main was such a thriving location. The hustle and bustle of the settlement at mid-day is reminiscent of life before everything went awry. Casting my gaze to the left, I can even see that one of the buildings has been converted to an indoor playground full of plastic slides, monkey bars, and other such playground equipment. About a dozen or so children can be seen running and laughing as they play tag and various other games.

The girl clears her throat, and I return my attention to her immediately. "Apologies," I say, "haven't seen a settlement this prosperous in a while. Such a sight can rather easily captivate the longing eyes of a wandering hermit such as myself."

The girl smiles and nods, then points to a small enclosure off to the side of the main gate. "Bite check." She says, and I sigh. I go through this process daily upon entrance to settlements new and old alike, but it's still a little bit off-putting when the inspection is overseen by a cute girl or perhaps an unscrupulous woman such as my good friend over at the Riverside gatekeep. I follow the girl into the cloth enclosure, thankful to at least be allowed the comfort of relative privacy. In some lesser-developed settlements, visitors are simply stripped and inspected at spearpoint right at the front gate in broad daylight.

The girl lets the door flap close behind me and flicks the light on. The illumination is harsh, but my eyes adjust quickly. Illumination is key when performing an inspection. Even a single tooth mark hidden in the armpit could lead to the devastation of an entire colony. Lansing Main is historical evidence of that fact.

I set my backpack, straps, holsters, and weapons to the side of the door, and remove my clothes with a lack of hesitation cultivated by years of inspections. The girl hides her surprise very badly, and she bites her lip a little bit as I peel off my boxers and toss them on the table. My body is in incredible shape, honed to perfection from half a decade of walking and crawling and fighting my way through the city streets and backwoods of central Michigan. Scars and embellishments adorn my skin, a testament to the hardships my line of work entails. It's no wonder that I'm the only person who's ever been known to travel incessantly to assist settlements with their various maintenance and zombie issues.

I stand in the center of the room and look at the girl expectantly, waiting for her to do her job. Her bashfulness is making me really want to tease her. She approaches me slowly, flashlight in hand, and gestures for me to raise my arms, which I do. She scours my body carefully, checking every inch for any sign of fresh zombie damage. The most recent wound is on my back, a week-old puncture wound from backing into a scrap metal piece while holding off a trio of zombies in a cramped alley. The girl runs her fingers over the wound and whistles softly. "Must've hurt."

"Not too bad. I've had worse." I peek over my shoulder at her as her eyes roam my chiseled frame, drinking in the sight of a lad in her age group naked before her. It's clear to me that the settlement doesn't have any guys her age and she's probably feeling quite restless.

"I can see that." She says, returning to the front of my body and kneeling down. She checks my thighs and calves a little quicker than she'd done my upper body, and switches off the flashlight, exhaling audibly as she backs away and turns around. "You're good." She says, setting the flashlight on a shelf next to the door.

My mischievous nature takes hold of me, and I decide to investigate just how restless the poor girl truly is. "You missed a spot." I say, and she spins around quickly, a look of nervousness on her face as she is forced to evaluate my naked body once again.

"What do you mean?" She says, tugging on her long hair as she attempts to make eye contact.

"I had a tussle with a rather persistent zombie in the alleyway just outside the settlement and he really could've tagged me anywhere. I'd appreciate a very thorough check of my lower body, just to be safe."

I approach her slowly and ever so gently ease my body against hers, reaching my hand around her waist and pulling her closer as my cock hangs between us, waiting to be given attention. She looks up into my eyes, still pretty uncertain but undeniably itching for intimacy. I feel her hand slide down the ridges of my abs to my genitals, where her slim, cool fingers wrap gently around my shaft and squeeze.

With the line well and truly crossed, she seems to give in to her desire, lowering herself to her knees and rubbing my manhood against her cheeks and her lips. She moans with pleasure as she smells and tastes the shaft of my cock, all the while massaging my balls gently with her hand. Her dry and cracked lips slowly part and envelope the tip of my shaft. I reach my hand down and help hold her hair out of the way as she begins sucking and licking my penis. She moans and sighs quietly as she enjoys the taste and the feeling of my thick cock filling her mouth. I close my eyes and follow her lead, focusing intently on the sensation of my rod disappearing into her cute mouth.

Wishing not to prolong things needlessly, I grab her head and begin thrusting slowly and gently. I can feel my orgasm approaching and allow it to build in intensity. "I'm going to cum." I manage to say, and she gestures to her mouth enthusiastically, still unable to speak.

I groan as I release a big load of thick cum into her throat. She moans and sucks diligently as I empty my entire store of semen into her mouth. After I'm finished, I pull my quickly deflating cock out of her mouth and check to see if she swallows. Her eyes lock onto mine as she drinks it down and opens her mouth to show me that it's empty.

I smile and stroke her hair. "Good girl. That deserves a reward." I lift her to her feet and spin her around, gesturing for her to put her hands on the table. She obeys and presents her backside to me. I reach around her waist and undo her jeans, then slide them and her panties all the way down to her ankles, helping her step out of them so she can spread her legs for me. She bends over completely and moves her feet far apart so that her tight little pussy and asshole are fully on display for my hungry eyes.

I kneel down and lean in, running the flat of my tongue over her entire slit. I lap at it like a thirsty dog drinking cool water from a bowl. I use my fingers to spread her labia and mash my tongue against her inner genitalia. I push the tip of my tongue into her vaginal canal and wiggle it as hard as I can. I lean back and grab her thighs, picking her up and laying her on her back on the table. I push her knees apart and return immediately to my meal, placing both my hands on her petite titties and using them as leverage to mash my face into her pussy as hard as I can while I eat her out. Her thighs clamp down on my ears and she puts her hands on the back of my head as she squeals and whimpers as silently as she can. I can feel her legs trembling a little bit and smile as I imagine what they'll be doing once I'm done. I redirect my focus on her clitoris with my tongue as I insert two fingers into her vagina and begin wiggling them. I take my other hand off her breast and push down on her pelvis, earning myself a truly delicious squeal of surprise from her. I increase the intensity of my fingering and licking, and soon, she admits that she's going to cum.

"Oh, baby, I can't hold it any longer!" she whines, and I watch her face intently as I flick her clitoris with my tongue. I feel her pussy clamp down on my fingers and she arches her back, covering her mouth with her hands as she squeals from the pleasure of the climax. I pull my face away and rub her clitoris vigorously as she cums, gleefully watching her legs spasm and shake. After a few moments, she goes limp and lies on the table, huffing and trying to catch her breath. I sit on the table beside her and begin rubbing her stomach and her thighs.

"How'd that feel? Better than a table corner?" I whisper in her ear as I administer my aftercare.

"I use cucumbers from the garden, asshole." She says under her breath, smirking weakly. I help her get to her feet and put her clothes back on, then quickly dress myself as well. I gather my belongings and exit the tent behind her, keeping my facial expressions even as I head directly for the Duke's establishment.

"He's clear." The girl says to the rest of the guards, and they nod affirmative. I see them giving me a side eye, and all I can think to do is shrug. One of them rolls his eyes, and I decide to vacate the premises before he comes up with something snarky to say.

...

The Duke's residence is much less extravagant than I had anticipated. For a man with such egotistical tendencies, I hadn't expected such a humble abode. He leads me through the makeshift home, past a library and a sitting room of sorts. There's no mirrors, paintings, sculptures, or similar such eccentricities. Just elegant but simple furniture and photos of people and places from the Owosso of old as well as photos of the settlement and it's folk. I follow him up the stairs and into his office, where I'm greeted with the sight of an older woman dressed only in a kinky maid outfit. The blouse of the outfit is designed to be open, and her massive breasts are sitting freely in the open air, suspended on the bottom by thin straps of lacy fabric to make them stand out proudly. Instead of a skirt, the lower half is just an apron, with nigh a scrap of clothing to obscure her backside. The woman curtsies elegantly as we enter.

"Welcome to the home of Duke Wellbring, Mister Jack." She says, smiling pleasantly as the Duke rounds his desk and sits in a shiny leather chair. He smooths back his silver hair and scoots the chair up to the desk.

"Anastasia, can you please fetch us some coffee? Thank you." He says, and gestures for me to sit across from him at the desk. I grab the chair and plop into it casually, trying to keep my eyes focused on the Duke as what I presume is his housekeeper struts to the door and exits. Her voluptuous, exposed ass cheeks sway and jiggle as she moves slowly and gracefully out of the room. "My wife, Anastasia. I hope you don't mind her appearance. 'Tis truly a blessed sight for the tired eyes of an old, physically taxed man such as myself." He leans back, eyeing me closely as I cringe internally. I keep my facial expression blank as I reply.

"I'm sure she's glad to be able to comfort you in such a simple way." I think I'm beginning to see where all the Duke's ego has gone to work. He cares not for materialistic things, and rightly so. Frivolous belongings are hard to come by these days. He probably enjoys the power he commands over the settlement as well as those close to him. I decide to conduct business as tactfully and swiftly as possible so that I can avoid being manipulated. I'm rather resourceful out on the streets, but dealing with people politically or diplomatically has always been a skill that's failed to manifest despite my attempts to learn. I often find myself talked into corners if I flap lips with shrewd people for too long.

"I'm glad you decided to expedite our request for aid. It's sure to become quite the tragedy if not addressed promptly." He passes me a piece of paper, and I pick it up to read. It's a note that appears to have been written rather hastily. "I found that on my desk a few days ago. It's a note presumably from my daughter, Serenity, claiming that she's dissatisfied with her life in this settlement and wishes to see the world, however ugly it may be."

"A pretty natural sentiment among young folk such as herself." I interject, and the Duke frowns.

"A conceited sentiment, born of ignorance and immaturity. The adventure and freedom of the wilderness outside the safety of the walls is not nearly worth the destruction it brings. Regardless, the note is not actually written by my daughter. It's been left by an infidel that we foolishly allowed to board inside our humble town. A man by the name of Thaddeus. He appeared at the gates a week ago and stole away with our daughter only a few days later. The grocer and our bartender both reported hearing him mention Cincinnati, and thus, I suspect that her future is that of a rather dark nature."

My eyebrows pop up at the mention of the Cincinnati settlement. In this post-society world, baser instincts returned to the forefront of human behavior. Such an unchecked, consequence-free environment led to a massive outbreak of violence, sexual deviance, and in Cincinnati's case, a resurgence of slavery in the free world. It's not a race thing, it's not even a sex thing. It's just the strong manipulating and using the weak in the same way that I use tools and weapons. The settlement itself is a testament to the depths of human depravity, having grown exponentially in the years since the apocalypse. Where other, kinder settlements have fizzled out of existence from starvation, illness, or zombie infestation, Cincinnati has thrived upon the sale of human beings. There are even slavers who prowl the wilds and infiltrate settlements in search of naive people to kidnap and sell for profit. Of the countless settlements along the northeastern portion of the United States and southern half of Canada, thousands of them participate in the sale, trade, and usage of slaves.