Chapter 36 by johnmary56
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Week 2: Wednesday, 13th Dec 2029, Morning
I woke earlier than Yoko again, her soft breathing steady beside me. Last night's gaming marathon must have been exhausting, unbecoming behavior for a ****, but I'd just used her money to purchase nine new additions to my collection. I'd overlook her indulgence this once.
I delivered a sharp slap to her bare ass, watching her body jolt and wiggle like a startled worm. The temptation to wake her properly with my cock buried in her tight ass was strong, but anticipation for my new acquisitions overrode immediate gratification. Nine fresh slaves awaited their first day of training, and I had extensive plans for all of them.
Making my way to the office, I sent a brief message to Jennifer and Seraphina requesting their presence, along with my morning coffee. Seraphina's application for Vice Head Girl would be waiting, and while she'd earned the position through her exceptional qualifications, I savored the ritual of making refined slaves document themselves like livestock. The psychological impact of self-commodification never lost its effectiveness.
There was something intoxicating about highly educated slaves, watching a distinguished academic transform into a **** fucktoy at my command proved endlessly fascinating. Gives whole new meaning to the phrase 'fucking her brains out'.
Lost in these thoughts, I barely noticed their arrival until Jennifer's voice cut through my reverie.
"Permission to enter, Master. I've brought Seraphina for your inspection."
They waited respectfully outside my open doorway, Jennifer stood naked and poised while Seraphina crawled naked behind her on hands and knees, a leather leash connecting her collar to Jennifer's grip.
"Come in."
Jennifer entered with practiced grace, immediately dropping to her knees before my desk. Seraphina crawled to position behind her, both slaves maintaining perfect posture. With ceremonial precision, Jennifer extended Seraphina's application with both hands.
I accepted the document and leaned back against my desk, studying my Head Girl and prospective Vice Head Girl with deliberate slowness.
"Stand. Both of you."
They rose in unison, hands clasping behind their necks in the standard display position. Their firm tits thrust forward proudly while their legs spread just wide enough to expose their pussies completely. Perfect form.
Scanning through Seraphina's application, one detail caught my attention. "Inexperienced with penetrative sex," I read aloud. "Jennifer, what's your assessment? Show me her pussy."
Without hesitation, Jennifer moved behind Seraphina and dropped to her knees. Her face positioned level with Seraphina's hips as she gently spread the her pussy lips with both hands, exposing the pink flesh within.
"I refuse to believe it, Master," Jennifer said, her breath warm against Seraphina's exposed sex. "A cunt this delicious? How could any previous owner resist fucking her senseless?"
"Care to explain, Seraphina?" I asked with an amused smile.
"Thank you for the compliment, Jennifer." Seraphina's voice remained steady despite her **** position. "My previous masters were my father and brother. When I reached sexual maturity, Father was already quite elderly. My enslavement served primarily as proof-of-concept for the Utopian Orphanage, demonstrating his absolute faith in the system by subjecting his own daughter to it."
She paused, a slight tremor in her voice. "He fucked me only twice. First during my graduation ceremony, using the spoilage of my virginity as the ceremonial seal of my slavery. The second and final time was on his deathbed, he wanted to die in ecstasy, and I was honored to provide that final service. Despite our unconventional relationship, we loved each other deeply."
Her expression darkened slightly. "My brother found our bond disgusting. I could see the desire in his eyes, but his pathetic restraint held him back. He considered himself superior to Father, too moral to use me sexually while finding it perfectly acceptable to sell me for funding. Regardless, my ass remains virgin, and I'm grateful to have preserved that hole for you to claim. I hope to serve you as my third and final master."
"Well," I said, setting down her application, "I invested over a million in you. I intend to utilize all your holes, and that brilliant mind, extensively."
"I expect nothing less, Master. I exist to be your personal cocksleeve."
"Such crude language," I teased. "I expected more sophisticated vocabulary from someone with dual doctorates."
Seraphina cupped her heavy tits, lifting them slightly. "Well Master, I do have two of these that are far more entertaining than any diploma."
"Those fun bags will get proper attention later. Right now, we have eight new slaves requiring immediate evaluation."
I moved to the sofa, both slaves gracefully following, dropping to their knees beside my legs with practiced precision. The fluidity of their movement never ceased to amaze me, how naturally trained slaves adopted the kneeling position, thighs slightly parted, ready for inspection or use at a moment's notice. Muscle memory born of perfect conditioning.
"Let's discuss the four bodyguards first. Seraphina, you handled the auction yesterday. Give me a comprehensive briefing on who they are and why I can trust them with my safety."
"Yes Master." Seraphina's voice carried the measured tone of academic authority even in her submissive position. "All auction items were processed through the Free Cities Network. I was originally scheduled as merchandise myself, but they found the concept of me auctioning myself off particularly... entertaining."
"It certainly was effective."
"Thank you for your winning bid, Master. Regarding the bodyguards, their internal files provide fascinating psychological profiles. They were acquired from different global sources, handpicked from various organizations and subjected to several months of preliminary conditioning before being packaged for sale. However, their training regimens were truncated because the Network was so eager to capitalize on my auction that they rushed these other slaves to market prematurely, using them to create a worthy showcase around my sale."
I leaned forward slightly. "Details on each."
"The designated squad leader is Catalina Refugio. Born into plantation slavery in South America, she successfully orchestrated a **** revolt that resulted in her master's **** and the establishment of what she termed a 'liberated settlement', a sanctuary for escaped slaves."
"That hardly sounds reassuring for my personal security."
Seraphina's expression remained analytically calm. "According to her psychological profile, she volunteered for re-enslavement. Her settlement grew beyond manageable proportions, attracting **** slaves and unwanted attention from slavers and military forces. Despite her tactical brilliance in repelling multiple large-scale attacks, she recognized the mathematical impossibility of indefinite resistance. She negotiated a contract with the Free Cities Network, guaranteed protection for her established community in exchange for her personal submission. The agreement specifically prohibits new refugee intake while maintaining security for existing residents."
"Essentially, she's protecting her people through her own sacrifice."
"Precisely, Master. Her psychological profile indicates she views personal freedom as worthless compared to community safety. Any betrayal of her new master would result in the immediate re-enslavement of everyone she fought to protect. She's strategically invested in loyalty."
I nodded approvingly. "Next."
"Esperanza Espada, known operationally as 'EE.' Former royal bodyguard for the Spanish monarchy, captured during a resistance operation. She assumed her principal's identity, the princess, to facilitate the royal's escape, resulting in her own capture and interrogation."
"Experienced protection detail. Promising."
"Indeed, Master. Her file indicates extensive **** designed to extract royal family intelligence, but she never broke protocol. When ransom demands were issued, the monarchy abandoned her completely. The resistance, recognizing her commercial value as an intact, trained bodyguard, preserved her physical condition for eventual sale. Her psychological evaluation reveals complete abandonment of hope regarding rescue or recognition. She's psychologically severed all emotional ties to her former life and has formally committed to absolute service to whoever claims ownership."
"Someone with nothing left to lose except what I give her."
"Exactly, Master. Her honor-bound personality structure makes her psychologically incapable of betrayal once she's accepted a new master's authority."
"Third candidate?"
"Linh Sullivan. Vietnamese-born assassin with extensive underworld reputation. Her family was eliminated by a mercenary who subsequently adopted and trained her as his personal weapon. She operated under his direction for years until a political **** contract resulted in his **** and her capture."
I raised an eyebrow. "She knows her 'father' murdered her birth family?"
"Yes, Master. However, she was too young during the initial trauma to form meaningful familial attachments. Her psychological conditioning treated her handler as both father figure and master, creating a complex trauma bond. Her evaluation suggests she views herself fundamentally as a tool requiring direction rather than an independent person. She's actively seeking a new handler to provide structure and purpose."
"Or she could be an exceptionally skilled actress planning ****."
"A valid concern, Master. However, her psychological profile shows complete emotional detachment from personal desires. She literally cannot conceptualize existence without a controlling authority. Independence terrifies her more than ****."
"We'll monitor that carefully. Last one?"
"Yoon MinJung. Korean corporate spy specializing in social engineering and data infiltration. She maintained deep cover as an incompetent office worker while conducting industrial espionage. Her final operation resulted in capture and complete financial devastation through legal damages."
"Standard financial motivation then."
"More complex than that, Master. Her psychological evaluation reveals she views slavery to a wealthy master as a significant upgrade over poverty-stricken freedom. She's explicitly stated she'd rather live as pampered property than struggle as a destitute free woman. Her motivation is comfort and luxury rather than ideology or loyalty. She sees this as a career advancement rather than punishment."
"At least she's honest about her priorities. Security risks?"
"Minimal regarding rebellion, Master. However, her technical skills require careful management. She could potentially compromise digital security if given inappropriate access."
"Yoko's expertise will handle any digital threats she might pose."
"Then that completes the briefing, Master. Should I summon them for your personal inspection?"
"We can wait on that. Let's see the four influencers next. I'm genuinely curious what they bring to the table." I said.
"Of course Master. I hope their pathetic followers realize their beloved content creators are now getting fucked senseless by you. They must be seething with envy."
"Fucking them does provide novelty, but they serve more strategic purposes too."
"Strategic purposes? Forgive me Master, but they're just failed influencers with delusions of relevance."
"I'll enlighten you later. Tell me about each one first."
"Yes Master. This batch represents particularly fresh merchandise, all acquired from Old World territories where slavery commercialization remains underground. Their conditioning was minimal, as the Free Cities Network assumed their former celebrity status would sufficiently justify premium pricing. Perhaps they even calculated that new masters would enjoy their resistance when fucking them."
"Amateurs indeed. Continue."
"Catherine Bailey. British travel vlogger from inherited wealth, notorious for condescending content portraying developing nations as her personal playground. She specialized in judgmental commentary about New World faction territories, treating our superior systems as primitive curiosities for her privileged audience's entertainment."
Seraphina's academic tone sharpened with disdain. "She survived multiple **** attempts thanks to family ransom payments, but finally encountered a Mexican cartel uninterested in money. They wanted to send a message about entitled foreign bitches exploiting their territory for content. Rather than execute her, they sold her to us, believing New World slavery would provide more creative punishment than simple ****."
"Poetic justice. Next?"
"Tiffany Huang. Taiwan-born American who built a fraudulent financial independence empire. She marketed herself as a self-made success while secretly funding her lifestyle through increasingly dangerous loans. Her 'Female Financial Freedom' courses were particularly ironic given her complete dependence on borrowed money."
"The psychological irony is delicious, preaching independence while drowning in debt."
"Precisely Master. She borrowed extensively from New World financial networks, apparently believing American protection would shield her from consequences. When the debt matured and she couldn't pay, her government demonstrated exactly how much they valued one missing whore. Her transition from fake financial guru to owned property should provide excellent entertainment."
"She'll certainly appreciate the lesson in actual dependency. Next?"
"Madison Lux. American wellness influencer from privileged background whose entire 'self-care empire' was maintained by household staff while she claimed personal credit. Her morning meditation routines, organic meal prep, and fitness regimens were all performed by servants while she filmed herself taking credit."
Seraphina's voice carried analytical contempt. "Her downfall came through MLM pyramid schemes, she promoted wellness products that devastated her followers financially while enriching herself. When the scheme collapsed, her victims' lawsuits stripped away everything. Now she can practice authentic self-care by personally serving her master's every need."
"Jennifer and you will handle her training. Enjoy dismantling her fake empowerment brand."
"Thank you Master, I'll relish correcting her delusions. Finally, Karen Keller. This one particularly offends me."
Seraphina's composure cracked slightly, revealing genuine anger. "Double doctorate in Gender Studies and Social Policy, completely worthless fields that exist only to validate female victim narratives. Militant feminist who built her brand selling anti-male hatred disguised as academic theory. She literally marketed merchandise calling men inferior while preaching female superiority."
"I sense personal antipathy here."
"Forgive me Master, but this cunt gives legitimate academics like myself a terrible reputation. Her vegan supplement line killed a follower through malnutrition, yet she showed no remorse, only concern for her brand image. Lucky for her, all that cum she would drink would provide all the protein she need. She spent years teaching women to hate and resist male authority, making her current position as male property beautifully ironic."
Seraphina's voice turned venomous. "What's complicated about gender dynamics? Masters are male, slaves are female, hierarchy established through natural superiority. I fail to understand why such obvious truth requires doctoral study, unless the goal was deliberately obscuring reality with feminist propaganda."
"You'll have extensive opportunities to educate her on practical gender relations."
"Yes Master. I look forward to demonstrating how completely her academic arrogance crumbles under proper authority."
"I have extraordinary plans for these four. With systematic conditioning and strategic rebranding, I see an elite marketing and PR operation. Picture this, the wellness guru preaching her master's superior lifestyle instead of her hollow self-care bullshit. The financial independence princess explaining how complete economic dependence on her owner provides true fulfillment. The condescending travel blogger enthusiastically promoting group sessions where she and her **** sisters service me together as the ultimate cultural experience."
I paused, savoring the psychological architecture of their upcoming transformations. "And finally, the militant feminist will pioneer a revolutionary form of feminism, preaching that female superiority is precisely what makes women naturally better slaves. After all, if masculine traits were so valuable in slaves, why do we bother feminizing men into sissies?"
"We will achieve your vision, Master," Jennifer interjected with quiet certainty. "Whatever methods are required."
Of course they would. Their devotion was absolute, their competence proven.
"Let's break for now. Bring the bodyguards in this afternoon, I want to evaluate their security capabilities before dealing with the influencers."
"Yes Master," both slaves replied in perfect unison, their voices harmonizing in submission.
What's next?
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Free Cities Story
Loosely based on Free City Game
A man finds himself in a world very much like a game he's played.
Updated on Aug 31, 2025
by johnmary56
Created on Dec 5, 2024
by johnmary56
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