Jewel Ascending

Never run afoul of the law in Allegoria.

Randolph James Johnson tugged demurely at his skirt as he waited to be addressed by the judge. His appearance today should have been his final appearance before the court. For 6 months he had followed the guidelines and the rules of the courts sentence but now having finished his sentence and probation he was eager for it to end. But instead of finally receiving official recognition from the court of his satisfactory completion of his sentence and walking out of court a free man, his lawyer had informed him that new charges had been leveled against him that very morning.

Allegoria took sexual harassment allegations very seriously. Despite the complete lack of corroborating evidence the court had chosen to believe the testimony of his female accuser over his denials to the contrary.

Randy still wondered about the fairness. Sexual harassment allegations meant that only female judges would sit court and the prosecuting attorney assigned was almost always female as well. Randy had been required to hire a female attorney to represent him as well instead of use his usual attorney, who happened to be male.

Once the judge had determined that he was guilty he was sentenced to live for six months dressed as a woman. He was expected to learn what it was like to live, behave, and act as a woman so as to understand women better. The goal was that with his new found understanding of women’s needs and issues he would no longer be inclined to harass them.

The irony was that there was a full month long ‘boot camp’ in prison where he was forced to learn how to dress and act as a woman before his sentence even began!

And then he was legally on probation, sent back home were he was living and working at his normal job, being seen by his employees and his friends. But six…actually seven months was enough! His sentence was complete! He had complied with all the strange and unusual demands of his sentence. It was time served and he should be allowed to resume his right to present as male!

He was a man damn-it!

Randy’s lawyer nudged him as his case was being called up and it was time for him to present himself and take his place in the dock.

Randy had learned quite a lot during his sentence and he also knew that the mere act of walking up to the dock would be looked upon as a either a mitigating factor or an aggravating factor depending on his appearance and performance.

Randy took great care as he stood in his kitten heels to carefully smooth out his 1950’s style dress. It was a case of everything old being new again. The dresses had undergone a revival in popularity back in the 2050s and now 50 years later they were once again considered fashionable.

The bodice and skirt of the dress fit Randy perfectly. As an importer of women’s clothing he was in a unique position to understand the importance women placed on a dress that fit well.

Randy had adhered strictly to the court ordered sentencing guidelines. If the dresses he wore were ill fitting it would have been an aggravating factor. The blue floral print pattern of his dress was cute without being loud or flashy. It was also tailored to fit his court mandated enhanced figure; bra inserts to attain the appearance of having a B cup bosom, and hip and thigh padding under his pantyhose to fill out his figure. With his naturally slim waist the final overall effect was adorable and he wore it well.

Randy had also been careful that morning with his cosmetics. He had used subtle colors, pastels and nudes to feminize his appearance although with his epicene features it was hardly necessary. He would never be viewed as a bloke in drag, not would he be ‘made’ out in public unless the viewer scrutinized very closely, but rather as a youngish woman who took good very good care of herself.

His only concern was his blond hair. Randy had always kept his hair short, routinely cutting it down to a crew cut. The sharp appearance worked well with his epicene features. But to appear feminine the court wanted more. He had been required to wear wigs until his hair had grown long enough for a stylist to be able to fashion it and once his hair was long enough he was allowed to forgo the wigs. The stylist had styled his naturally blond hair in an adorable pixie cut complete with blonde spit curl centered on his forehead. It was fairly easy to maintain as well.

Randy knew that his walk to the dock was also being scrutinized. He made sure to use proper posture and walk with shorter steps. The heels actually helped some as when walking heel to toe his hips would sway more femininely than his previous typical masculine gait.

Randy wanted his sentencing completed and made every effort to meet the sentencing demands of the court.

As he arrived in the dock and carefully walked up the stairs to the elevated platform he now stood in the center of the courtroom where all eyes were upon him. He held up his right hand as he was sworn in. He vividly recalled how it got to be here in the first place.

**

“Look Karen, I’m not saying that it isn’t a good idea. Selling more skirts is good for business and I don’t care who we sell them to, but the method you suggest is ethically questionable.”

“How is it unethical?” Karen bristled at being challenged.

Randy watched carefully the woman standing before him. Karen took the time for daily salon appointments to have her makeup expertly applied. Her reasoning was that if that was how the wealthy nobles and elite wives did it, hiring personal cosmeticians to attend to them daily, then she deserved it as well, damn the cost!

Despite her beauty he knew her too well. To him, she always looked like a pit viper poised to strike.

Her long luxurious red locks of hair framed her perfect heart shaped face. Her cute button nose, courtesy of the cosmetic surgery his father had provided seemed to wrinkle slightly across the bridge when she was poised to become angry.

Randy uncharitably imagined the way her hair style flared out from her ears was like how the head of a cobra would flatten out into a hood.

Her plump full lips, fuller now from a recent collagen injection treatment, were firmly pressed together from impending anger. Her thin eyebrows arched high above her eyes, but not from surprise. Her expertly applied eye makeup would have been stunning if her expression wasn’t drawing them together in readiness for confrontation.

Randy sighed internally and struggled to control his ire. He steeled himself for another verbal altercation with her. In the months since his father’s death she had been relentless.

And rather than dress for business Karen always liked to be the first to try on and model the new fashions that they imported. She always justified it by stating her need to be seen in current fashion as a way to promote her business.

Her fashionable figure hugging sheath dress expertly accentuated her perfect figure. Very serpentine, he imagined.

Her full 36DD breasts (breast augmentation being yet another gift from his father’s money) her tight and firm 24 inch waist line (from the hours she spent at the gym or starving herself) and her full firm 36 inch hips and pert yet full round bottom (how many exercise bicycles has she gone through this year anyway?)

The hem of her dress hung even with her upper thighs so that her long legs could be displayed to full effect. An effect that was magnified by her 4 inch Christian Louboutin heels, straightening her posture, lengthening the appearance of her legs, improving her back and shoulder alignment to emphasize her DD bust…

Randy took a deep breath before continuing. It was like he was always trying to tip toe around broken glass when dealing with her. Despite his best efforts an edge was creeping into his voice.

“You want to promote skirts for men at the colleges by having them banned just so you can organize your protests and accuse the administrators of being…I dunno…sexist, or something.”

“And the outrage will force them to authorize the wearing of skirts for men who choose to do so. We get free publicity and a cadre of idealistic students who will agitate for change to show how progressive they are…it’s a win-win scenario.” Karen sharply interrupted. She would always rather be the one speaking than the one being spoken to.

“I know you did something similar to make kilts an optional uniform item in schools and for civil service uniforms too and yes, sales of kilts did improve, but don’t you think you are taking this too far?”

Randy was often frustrated by his stepmother’s smug superiority complex and her third-wave feminist attitudes about men. Coupled with her wild whims and her narcissistic and belligerent attitude…any discussion devolved into an argument and somehow those arguments always became about her. How she had ever managed to win his father’s heart when his mother died was beyond understanding. And now that his father had died and left the company to him she seemed to take great delight in making everything about his job more difficult and challenging than it needed to be.

For whatever reason, the business of importing fashionable women’s clothing came easy for Randy. In his first year since taking over his stepmother’s failing company he had turned everything around and made it profitable. After his father died and left him the company in his will he had continued to succeed and do even better. They were finally on track to have their first million dollar profit year.

Karen positively seethed with anger. She was incensed that her erstwhile stepson would challenge her decisions. Karen had worked too long and too hard to get to where she was today only for her dead husband to leave her company to his son.

After all, it was HER company. She had to do all the work of convincing her husband to fund her and provide the start up capital. And being a typical man he sure took a lot of effort and convincing. She had done everything to make him happy in order to get where she was and she put everything she had into making her business a success.

Sure, her dead husband’s contacts, and business and financial acumen may have contributed…somewhat…to her import and export business, and certainly his money didn’t hurt, but Karen knew that it was her ambition and drive, her willingness to do whatever it took! It was her fashion sense and her blood, her sweat and her tears that had been the real story that had made her company a success.

Karen was embittered when she found out about her husbands treachery…after everything she had done to satisfy him…and was determined that her flaming faggot of a stepson be put in his place. Sure he was good with the books and accounts, and made sure everything ran smoothly, but he didn’t respect her. It was Karen’s vision that was the real reason there was a company in the first place!

Karen didn’t consider herself as homophobic nor did she harbor any particular hatred of gays. But she couldn’t fathom how an alpha male like her dead husband could have a pansy assed bottom bitch for a son and expect him to manage something that rightfully belonged to her.

Karen’s anger boiled over.

“I think our market share speaks for it self, and marketing dresses for men, to men, is a way to expand our share and our profits. As a fag it seems like something you’d be good at.” Karen venomously replied.

The little twit couldn’t see the big picture. First it was kilts in private schools, then as optional uniform items for civil servants. Next would be public schools and college students, and then not just kilts, but skirts, and that would lead to widespread acceptance in society, and all that would translate into sales.

Randy bristled at the insult and finally lost his cool. Randy snapped at his step-mother…it was a momentary lapse he would later immensely regret.

“Look Bitch, I’ve taken your crap for long enough. First off, I’m not even gay…but you…you are nothing but a gold digging whore! You may have somehow fooled my father and spread your legs to convince him to marry you but I don’t have to take your crap anymore. Dad left this company to me. If it weren’t for me, with your bad decisions and reckless spending, it would have gone bankrupt months ago.”

Randy never noticed Karen’s assistant standing in the door way behind him witnessing his harangue.

“Because of me this company is profitable and successful. Even our in house fashions are getting brand recognition. I think a little bit of appreciation for me for saving your sorry ass and turning this failure into a success isn’t too much to expect and that you should listen to me when I give you advice. You just might learn something!”

Randy was breathing hard from the fiery passion of his delivery. He was completely unprepared when Karen gasped, blanched, and fled past him out the office door. She had never run away from an argument before.

Randy shook his head in exhaustion and exasperation. He wasn’t a confrontational person and he regretted losing his cool. He probably went too far, and despite her misplaced homophobic rant…he decided that he would go and try to make amends…later.

Karen ran past her assistant to her office. Her assistant followed her into the room and shut the door behind her.

“Did you see that? Did you hear what he said?” Karen sobbed and looked to be on the verge of collapse.

“Yes I did. I saw everything. I heard what he said.”

“How could any son talk like that to his mother?” Karen cried.

Cindy’s arrival could not have been timed better. Being there to witness the end of the confrontation she had orchestrated was perfect. Karen now had to make her portrayal of the aggrieved mother and widow convincing.

Karen hugged her shoulders and seemed to collapse in upon herself. Cindy took the bait and embraced Karen. Karen gripped Cindy tightly and placed her head on Cindy’s shoulder as she sobbed in feigned despair.

“What he said was intolerable and disrespectful and it has no place in a place of business.” Cindy moved to take Karen’s face in her hands and lifted it up to look her in the eye.

“You must take this to HR right away.”

“HR? This is his company. They won’t do anything.” Karen whimpered theatrically. She knew Cindy was a lesbian and was interested in her. Stringing her along had been child’s play; keeping her hopes alive of a potential romantic interlude while making her loyal to her.

“Well then file a report with the police. They have a department that specifically investigates crimes against women. Even white collar crimes and harassment claims. What he did was wrong.”

“Do you really think we should?” Karen asked as she sniffled and dabbed at her tears. Being able to cry at will was a wonderful talent.

“I think it’s for the best.” Cindy affirmed. “What he said and what he did was totally inappropriate.”

**

Randy awakened from his reverie and he listened in stunned silence as the new charges were being read and the prosecutor made her case.

“Your honor, the accused is a businessman; an importer of women’s clothing and accessories. One week ago he traveled abroad, to Rome to meet with clothing designers and manufacturers and sign contracts for import to Allegoria.”

“As you can see from the photographic evidence, when the accused was abroad he had dressed in a male dark blue business suit and tie and forgone his court ordered makeup, dresses and heels. To be perfectly clear, at the time of this business trip he was subject to court order to dress as a woman and maintain a feminine appearance as part of a plea to avoid jail time from his conviction for sexual harassment of an employee at his place of business.”

“We also have signed and notarized witness statements that Ms. Johnson was wearing male clothing upon his return and did not resume his court ordered apparel until the next day.”

Randy flinched internally when he was addressed using female honorifics. After six months it was still uncomfortable for him. He listened as his attorney defended him.

“Your honor, my client did indeed travel abroad and wear men’s clothing for his business meetings. He did so at the behest of his company’s acting CEO and court appointed probationary monitor. Would the prosecutor actually have him wear dresses and appear as a woman outside the borders of our great nation?”

“Whether he would or would not is irrelevant. The sentence clearly allows for a probationer to travel abroad for legitimate business reasons and when abroad it is understood and encouraged that a citizen represents their country and should not take actions that are dishonorable or would bring shame or embarrassment to our country.”

“Our office of protocol clearly advises and encourages travelers to do their best to fit in and be polite and respectful of other countries cultures and laws when travelling. Attending a business meeting abroad being a man when dressed femininely could easily be considered impolite, improper, and disrespectful of the business associates he met. Loss of business trickles down through loss of business employment and eventual loss of tax revenue.”

After the prosecutor lay out the complaint and her evidence before the judge, and his attorney argued for him the judge motioned him forward in the dock so as to allow him to speak in his own defense.

“Your honor, I was told that it was OK to wear men’s clothing for the trip by my acting CEO as long as I informed the prosecutors office beforehand, which I did in an email to the prosecuting attorney handling my case. I was only gone for 5 days and I resumed my sentence mandates as soon as I returned. I followed the law as I understood it.”

Randy felt weak as he threw himself upon the mercy of the court and still indignant for what he considered entrapment.

“Very well,” the judge intoned. She looked at Randy as she appeared to take a moment to consider his statement. “The court will recess for lunch and return with a verdict in 30 minutes time.”

**

Randy sat quietly and pondered the sequence of events that led him to his business trip. It was all Karen’s fault.

Randy smoothed his dark blue knee length A-line skater skirt under him as he sat down at his desk. Despite nearly 3 months into his 6 month sentence he still marveled at the feeling of his panties when his hands slid past. Panties were confusing for him. They were actually more comfortable than the men’s underwear he previously wore before his sentencing. Some days he even forgot that he was wearing them. And the cool air that caressed his legs…

Randy shook his head in annoyance at the conflicting feelings. The sooner he finished his sentence then the sooner he could leave these feelings behind him.

Randy reached down and pulled off his high heels. Those he unequivocally would not miss. They hurt his feet terribly. He took a moment to relax and slip them off and rub his aching soles through his sheer taupe nylon pantyhose when his stepmother barged right into his office.

Since his original conviction she had seemed to undergo some sort of change in her behavior. She had become much worse. Her pithy and antagonistic attitude had been replaced with one of smug condescension. She was named by the courts as custodian of his business while he was on probation. She was also court appointed as his daily monitor to verify his compliance with his probationary requirements.

Randy was now legally required to answer to Karen. She took great delight in criticizing him and his business decisions and now his feminized appearance at every opportunity, knowing full well that he couldn’t argue back or risk the appearance of having broken his probation by being disrespectful to a woman.

Randy sat back as she approached and absentmindedly smoothed his cream colored blouse down over his bra and breast forms and made sure it was properly tucked into the hem of his skirt. He glanced at his polished nails and noted the time on the woman’s simple gold bracelet watch around his wrist. Karen didn’t have an appointment.

Karen was wearing a fitted sheath dress that expertly hugged and complimented her curves. With an asymmetrical off the shoulder cut and a parallel asymmetrical hemline that displayed her toned thighs and legs; she made a beautiful presentation. It was one of the company’s in-house designs she was claiming credit for.

As always her daily salon appointment had made the most of her perfect features. Randy would have been attracted to her if he didn’t know what a narcissistic cold and calculating bitch she really was.

Karen took quick note of Randy’s appearance. She focused mostly on his makeup. His makeup had to be somewhat heavier due to his need for beard concealer and foundation. Otherwise his eye-shadow and mascara were satisfactory and his blush and lipstick were also satisfactorily if somewhat amateurishly applied. He had neatly trimmed and groomed his eyebrows into a feminine “M” shape.

Karen finished her perusal of Randy’s appearance and was actually slightly miffed. There were no apparent transgressions today that she could report to his parole officer. Randy actually presented as a passably attractive woman.

“Our Italian suppliers are balking again at the price quotes.” She began without preamble.

“What do you recommend?” Randy asked politely. Cindy, Karen’s assistant, was here with Karen to take notes…and witness his behavior no doubt. Randy’s boot camp had coached him on how to treat female employees respectfully but apparently all that involved was simply asking polite questions and then letting…err…encouraging them do whatever they wanted anyway. Randy was unhappy with this as the company was once again losing money under Karen’s inept control.

‘You need to go there and convince them to honor the original contract.”

“S’yeah, right. Go there…dressed like this…” Randy regretted his comment as he noted Cindy seemed to jot it down on her note pad.

“No, of course not” Karen smugly replied “you can go to Rome, change into your usual males clothing at your hotel, and meet with them later. Your probation is almost up any way, when you come home you can change back.”

Randy was surprised by this news and suspicious of Karen for suggesting it.

“Well I hate to be a pessimist, but you are the reason I am in this mess in the first place. Why would you want to help me?” Randy watched Cindy jot down another note.

Bitch.

“Look, obviously I don’t like you…but I don’t hate you either,” Karen lied “We can at least be civil to each other at work. Your sentence is almost up and nobody is going to care.”

“Helping you helps the business, right? And right now business is suffering. So go to Italy, meet the suppliers, and make the deal. You can check with your lawyer first if you really want to.”

Randy paused only a moment to consider before responding. He was eager to ditch the skirts and lipstick and have a chance to dress in normal men’s clothing, at least for a little while.

“Fine!”

Randy would do a quick check of his probation contract before he went just to make sure.

Karen smiled as her plan fell into place. Ordering him to go abroad since he really didn’t have the right to refuse under his probation agreement, should be the final trap she needed to remove Randy from her company.

**

After only 30 minutes recess court resumed and Randy listened as the judge called the court to order and pronounced her sentence.

“In the matter of the Crown versus Randolph James Johnson this court finds the defendant guilty of the crime of violating the courts sentence and knowingly traveling abroad to avoid carrying out your sentence as specified by the prior court decision and the sentencing guidelines for crimes of sexual harassment.”

The voice of the judge rose sonorously as she continued reading her opinion.

“As the court considers the aggravating factors of ignorance; ignorance of the law is no excuse, and misogyny; the documented disparaging statements made by the accused about women and to women during his probationary period, the court is compelled by sentencing guidelines under royal statute as decreed by the crown, assented to by the house of lords, and approved by the subjects via referendum and majority vote to an extension of your sentence as follows:”

“You are to be remanded to the National Social Services Administration and Maintenance Department to serve an additional sentence of empathy training for rehabilitation.”

“You are to begin your sentence by serving eight hours in pillory on public display.”

“Furthermore, upon completion of empathy training and pillory, this court sentences you to not less than 3 years and not more than 7 years of indentured servitude.”

The judge looked up from reading her sentence and stared directly at Randy.

“Laws still apply to Allegorian Subjects wherever they are, even if abroad. Society takes a dim view on subjects who try to flout the law and this court decision shall reflect that view.”

“Bailiff, take Ms. Johnson into custody.”

Randy stood stunned as the bailiff cuffed his hands behinds his back and slowly walked him from the courtroom. He was being sent to the Bimbo Lottery! Photographers from the media used flash photography to capture the scene as he was walked from the courtroom. Women’s rights advocates present in the gallery cheered the decision. He noticed his stepmother, Karen, in the back of the gallery, smiling at him.

Randy wondered if he was being walked slowly because of the high heels he was wearing or to extend his humiliation before the press. He couldn’t help but wonder, was this an exercise in humility or an exercise in humiliation?

Right now, it seemed like an exercise in futility.

Donna Hancock also sat in the Gallery.

Donna, formerly principal and headmistress of Sacred Heart Academy, an all-girls school took notes as she watched the proceedings unfold. Since her dismissal from the Academy she found unpaid work as an intern at a local law firm.

Donna worked as a paralegal and was “reading the law” under the supervision and tutelage of a senior partner of the law firm. In a few more months she would have the experience to finally try for the Allegorian Bar exam.

Donna noted how male suspects in court seemed to fair far worse than female suspects. And the new laws regarding gender based offenses were particularly troubling. Almost every time a man went to court a conviction was the result. When a woman went to trial the conviction rate was less than 10%. These tendencies and this trend also resulted in extremely harsh sentences for relatively minor offenses.

Donna watched as the suspect…no, convict now, was escorted from the court room to the cheers of the many feminists in attendance.

As she glanced at her watch she noted the time. She had to go. She needed to get to her other job now. The pay wasn’t great but it was keeping her alive and covering her expenses until she could become a lawyer and get a new start on life.

**

Back in her office, formerly Randy’s, Karen sat back in the comfortable office chair and gloated over her success. She summoned her assistant via intercom to come attend her in the office.

Karen had watched with satisfaction as her stepson was led away. He really looked pretty in his floral dress and kitten heels with his hands cuffed behind his back. His expression of shock was priceless.

Cindy entered the office and Karen wordlessly hiked up the hem of her skirt as Cindy took hold of her panties and lowered them down to her ankles before she knelt down between her thighs.

Karen was ready to enact the final part of her plan upon Randy. With his second conviction and his legal debts she could now force him to sell the company. She had already set up the shell company and arranged a buyer and made sure that her share of the sale would be more than adequate to set her up for life.

Legally she couldn’t avoid paying Randy his share but the trust fund she set up to manage his assets while he was in prison was in another shell company that she controlled.

Cindy placed her hands gently upon Karen’s thigh high stockings and pushed slightly to open her legs wider and give greater access as she began to tentatively lick Karen’s labial folds with her delicate and talented tongue.

She should have had the money already if her elderly husband hadn’t had a heart attack and died before she could have him amend his will, Karen pondered. Once that was done she would have made sure he had a heart attack at the time and place of her choosing.

Karen eased down her chair a little bit and then placed her legs over Cindy’s shoulders. Giving Cindy even greater access to her pussy she sighed in pleasure as her assistants’ oral talents were applied to her clitoral hood. Karen had become very wet with saliva, arousal and excitement.

But instead she had to actually work and plan and scheme to force her stepson to do the right thing. And now that her scheme had been realized, she was ready to cash in and move on.

Karen sigh softly as Cindy’s tongue now darted tentatively into and out of her pussy, teasing her vaginal walls. Karen’s pussy juices were flowing easily with anticipation.

Tonight the attorney’s will meet for the last time with Randy and they will execute the court order that will force her stepson to sign over control of his company…to protect his interests, of course…and then she can see that it gets sold while the state would ensure that her son can continue to follow the path she had laid out for him.

Karen’s excitement grew stronger as Cindy now teased her clitoris directly. Karen crossed her ankles behind Cindy’s back and spread her legs as wide as possible. She gripped Cindy’s hair to pull her in tight against her pussy…her orgasm…she was so close now…mmmm…yes…

It was perfect! Believe the woman…it was gratifying to see that her faith in the public outcries she had orchestrated actually worked.

Karen moaned in ecstasy as her eyes rolled back in her head and her mind blanked as her orgasm crashed down upon her and overwhelmed her higher reason.

After her orgasm subsided Karen gazed happily at her Assistant.

Little Cindy…so cute…her totally submissive little pussy-licker…she was quite a find.

After the papers were signed she had a meeting with the buyer. He was handsome and well hung and there was no doubt in her mind that she was going to let him fuck her senseless.

But having Cindy take the edge off and sate her arousal would give her more stamina and let her control the pace and timing of the seduction. She didn’t want to appear too eager. She wasn’t a slut after all…

Karen could never bring herself to eat out another woman; the thought of her doing that actually sickened her, but the pleasure of receiving cunnilingus and oral pleasure was an entirely different matter.

Karen knew that she was effectively a lipstick lesbian and a pillow princess…willing to kiss other women to seduce them and then let those women satisfy her sexually but never reciprocate. Despite this she still had plans for Cindy.

Karen smiled at her good fortune of finding her.

Bright, with a bubbly personality and energetic, she had met her at a convention for up and coming clothing designers and manufacturers. Cindy not only had a degree in fashion and design but also minored in engineering. Her goal was to make the most comfortable and best fitting women’s athletic clothing possible.

She already had trademarked a company name; “Shü”, and was searching for a venture capitalist to provide the financial backing to launch her start-up.

Karen’s discovery of Cindy’s bisexual submissive nature was fortuitous. Karen’s seduction of her had been at times playful and at other times commanding. Karen had been quick to learn all of Cindy’s buttons and knew exactly how to push them.

Karen also considered Cindy’s clothing designs. She was truly in near genius territory. Her designs were optimally engineered for the female form. Her understanding of materials and fabrics made her clothing line simultaneously more breathable and more hydrophobic but also more flattering and functional. Kinesthetically speaking they moved like nothing else on the market. They were absolutely certain to revolutionize and dominate the women’s athletic clothing market.

Karen intended to take Cindy’s clothing line and also a small shoe manufacturer she had recently discovered and acquired and merge them into one larger company…If it worked they could make a fortune. If not then the tax write off’s would still be good for her bottom line.

Karen planned to bring Cindy with her to New York when she started her new life abroad as a wealthy heiress. It would be best to get out of Allegoria while she was ahead. Having a new business to run would give her something to do while she found her next aging and ailing widower to seduce. She was garnering a reputation in Allegoria and moving somewhere new would open opportunities. Bringing along a submissive slut to worship her pussy while she…hunted…for her next husband would also be a fine way to begin anew.

After all, she was a powerful, strong, and intelligent woman. Her dominance should be obvious to all. Obedience and respect were her due. It was only what she deserved.

**

The Pillory.

Randy waited, handcuffed, shackled and chained to his fellow prisoners. He had thought that at least for his public shaming sentence he would finally be out of his court ordered women’s clothes and wearing the typical unisex orange jumpsuit of the Department Of Corrections.

But as he was loathe discovering; that was not to be. In Allegoria; gender based offenses are considered especially heinous, and as someone who was found guilty of a gender based offense and under legally enforced mandatory cross-dressing restrictions he was required to wear a prison issued outfit specific to his crimes, and that outfit was to his mind positively indecent.

The first problem was the orange color of his booty-short panties.

The wide waist band had “Department Of Corrections” printed in black block lettering. It encircled his hips and sat low cut so that the top cleft of his buttocks was exposed to view. Inconceivably the wide waist band made the blaze orange section of the booty short panties seem even smaller. It would have barely constrained his penis had the court appointed mistress not forcibly and with what seemed malicious delight tucked his cock and balls away between his legs.

Now anyone who looked at his crotch would only see the smooth flat front and “V” shape similar to a typical woman’s anatomy.

Next was the fully formed sports bra in matching blaze orange color, the same color as his panties and as the other prisoner’s uniform prison coveralls. “D.O.C.” was printed in bold black lettering across his bust and “Department Of Corrections” printed in smaller lettering upon each bra strap over his otherwise bare shoulders.

That his bust had been fully padded out with silicon breast forms was yet another indignity that assaulted his senses. He had been mocked by the court appointed disciplinarian who told him gleefully that they were DD cup realistic breast forms.

They jiggled every time he moved; despite the sports bra, no matter how slight the motion. The disciplinarian who prepared him for the pillory had also used adhesive to apply them to his shaved hairless chest. It was disconcerting to him to note how their movement could be easily felt through his pectoral muscles.

Even the realistic silicon nipples stood prominently and created a noticeable impression through the fabric of the prison orange sports bra; making it look as if he had tits and his nipples were excited or aroused.

Finally, he wasn’t even allowed to wear the simple orange canvas dock shoes of the other prisoners. Instead, he stood precariously atop orange peep toe pumps.

The 6 inch tall block heel would have been terrible without the two inch platform toe to lessen the strain on his calves and ankles.

Every time he considered all the things that they had done to him his mental anguish increased.

His exposed toe-nails were all painted a high visibility fluorescent orange with a high gloss shine, and his fingernails were identically painted. The acrylic nails that had been glued onto his fingers were easily over a half inch long past the end of his fingertips.

His makeover at the hands of the court appointed cosmetician was equally humiliating.

Gone were the subtle effects he had perfected over the past six months; the minimum required to satisfy his sentencing parameters. Instead he was given a far bolder makeover than he would have ever done himself.

His face was painted in a way any streetwalking whore would be proud to see. Deep blue eye shadow and dark eyeliner had been applied to give his eyes a cat’s eye appearance. Heavy rouge on the apples of his cheeks and long fake eyelashes tickled the upper part of his face and eyebrows and made him blink often, which had the added effect of making viewers assume he was fluttering his eyelashes at them. His eyebrows had been plucked and shaped into gentle arches that gave him a “surprised bimbo” appearance.

The deep red lipstick that was applied to his lips was given a heavy coat of lip gloss such that the overhead lighting reflected as highlights from his full, pouting lips. The layering of his lipstick also made his lips look fuller and the make-up look ‘deeper’ and more luscious.

One prisoner seemed to be muttering something over and over again, shaking his head in denial.

“Allegoria, come for vacation, stay on probation.” He murmured.

The other prisoners at least seemed to try to be stoically clinging to their dignity.

Randy was lead out from the holding area last in line but he was also the one who attracted the most notice. Adrenaline and nerves gave Randy a sense of hyper awareness as if he could clearly see everything that was within view.

People in the mall gallery and walkways who had seen this all before and were by and large immune to the spectacle stopped to stare and point when he was escorted towards the platform. The other prisoners in their prison issued jumpsuits were largely ignored and the brunt of the public shaming seemed to fall onto Randy.

He heard one man mutter to another “Well you don’t see that everyday.”

Randy could clearly overhear one mother say as she reprimanded her son “See what happens to you if you mistreat a woman?”

The son, with wide eyes looking at the spectacle, solemnly nodded in the affirmative.

One by one the other eleven prisoners were quickly affixed to their respective pillories. There seemed to be a delay when they finally reach Randy and he started to wonder what the hold up was for him when one of the bailiffs brought out some form of low round padded rail attached to a single pole.

Randy felt as if he was hyperventilating, which had the unfortunate effect of causing his bosom to visibly heave.

“Relax honey…breathe…it’ll be over soon enough.” One of the guards watching Randy remarked sarcastically as he tried to calm him down.

Randy watched as the pole was inserted into a recessed slot on the floor. The padded rail in front of him was now even with his hips.

The bailiff roughly pushed him over the padded pole and held him down while another bailiff affixed his ankles to the bottom of the pole with the shackles he was wearing.

Randy already knew from his earlier sentence that wearing high heels would naturally give him a straighter more perfect posture, lengthening his calves and producing a longer appearance to his legs and as he was now affixed to the pole it was impossible to bend his knees. His legs were now pressed tightly together, secured to the pole.

The humiliation continued as his head and hands were now placed into the stocks and secured. He realized that his pillory was actually slightly lower than the “Hip Pad” meaning that his ass was now elevated higher than his head.

Randy struggled with the slowly increasing level of discomfort the position caused. The only relief he felt was when he lowered the arch of his back so that the hip pad bore most of his weight. This also lifted his feet up slightly and eased the pain in his ankles from wearing heels so high. The unfortunate side effect was that he was now publicly displayed in a position that could only be described as fully submissive.

“That’s right sissy, ‘splay dat ass!” Someone from the upper gallery shouted to the hoots and laughter from many of the other shoppers forming the crowd.

With sudden clarity Randy realized that with his high heels and legs firmly affixed to the leg pole, with his head lower than his bottom, and with the curve of his back collapsed downward, that his panty covered ass was fully exposed and on display to the public for his public shaming!

The booty short panties were cut such that his ass appeared quite rounded and feminine and the tightness of his panties caused the bottom seam of the panty to creep deep into the cleavage of his butt cheeks. Only a thong panty could possibly have been more revealing!

One final indignity was that unlike the other prisoners, his placard publicly announcing his crime was placed behind him, on the floor by his feet instead of on the pillory below his head. For the public to know what his crime was they would first see his plump full bottom barely covered in blaze orange booty short panties.

Randy fought his emotions as hard as he could but the humiliation of presenting his ass and face in public on pillory was just too much. He was unable to stifle the sob of despair and could not prevent the tears escaping his eyes from flowing.

Publicly shamed, Randy’s tears flowed freely. His tears caused his mascara and eyeliner to smudge and run down his cheeks. The bailiffs attending the prisoners and the public observing all reacted to Randy’s public shaming and contrition with varying displays of scorn, ridicule, amusement or acceptance.

**

The Hypnotherapist, the Pharmacist and the Head of the National Social Services Acquisition and Maintenance Department sat comfortably around a low table as they discussed the new training techniques that were to be implemented upon the newest group of servants.

“Let’s face facts,” the hypnotherapist began without preamble “If you continue to use strict corporal punishment as a training method you are limiting your program and will still face unacceptable levels of noncompliance among service providers.”

“And you say your techniques can reduce these rates?” Dr. Horace Jarrod Inon asked bluntly. As Head of the NSSA&M he entertained many petitioners and government contractors seeking lucrative contracts with the department. These two had managed to make it through the screening process to earn a personal meeting.

“Oi mate, I’m saying we can eliminate them completely.” The pharmacist smiled at Dr. Inon. His tobacco stained and chipped teeth and rough Irish brogue lending him a disreputable air.

“We have perfected a technique that can virtually guarantee compliance with training as well as increased acceptance as a service provider”, the hypnotherapist smoothly interjected.

Horace smiled politely at the beautiful hypnotherapist. She had a beautiful heart shaped face with near perfect features that she had accentuated with minimal makeup. Her cultured alto voice was soothing. Horace admired her professional appearance as well. A near perfect figure with long full styled brunette hair currently held professionally with a clasp behind her head.

Her dress emphasized her best features and also left her long nylon clad legs on display. Horace had a thing for women with nylons. One of his changes he instituted upon accepting his current position was to amend the dress code for all female service providers to always include pantyhose, tights, or stockings.

“And how can you make this claim, realistically?” Horace challenged.

“I believe you are well acquainted with Countess Jewel Delacroix?” The Hypnotherapist asked.

“Yes, I do know Lady Delacroix. Her husband was always an ardent supporter of the work we do here.”

“Indeed, a good man and noble, may he rest in peace.”

“Oi…car crash…terrible way to go.” The pharmacist awkwardly chimed in.

“My colleague and I have perfected a technique using hypnotherapy and pharmaceuticals that have conditioned Lady Delacroix to such an extent that she has fully assumed her role as the male-bride of Count Delacroix. The control is remarkable and has extended into her life now that she is a widow.”

“She intends to retain her female presentation despite her newfound freedom from the arranged marriage.”

Horace took that statement with a grain of salt. He was aware of several of the codicils of the count’s will and knew that Lady Delacroix’s willingness to continue presenting as female may have something to do with the hundreds of billions of dollars she now inherited as long as she remained and presented as female rather than any hypnotic conditioning.

“So how do you plan, exactly, to be of service to our service providers?”

“Y’er whores, ya mean…” the pharmacist broke in “and we intend to do it with this.”

The pharmacist reached into his pocket with his gnarled rough hands and pulled out a small clear vial of pink liquid and placed it into the center of the table.

“I call it ‘Docility'” The pharmacist grinned again.

“And what, exactly, is it?” Horace asked, even though he had thoroughly read their written proposal and already knew.

“It’s a unique chemical that acts as a sedative, a hallucinogenic, a central nervous system depressant, a testosterone inhibitor, and a custom amphetamine that can increase susceptibility to cognitive suggestion.”

“Making hypnosis much more effective.” The hypnotherapist chimed in.

“Collectively these drugs penetrate the blood brain barrier and sit in the brain acting like a catalyst. They speed up and facilitate a chemical reaction without being used up themselves. The compound reacts in the presence of endorphins which enhances the desired docile and submissive behavior.”

“Every exposure to endorphins will compound the effect of the previous exposure, accelerating submission to the desirable behavioral traits.”

“And the drugs are perfectly formulated and targeted and do not work against each other.”

“So in a nutshell, the more the recruit orgasms, the more submissive and obedient he or she will become.” The hypnotherapist finished.

“So…no contraindication?” Horace asked. He was impressed with their presentation and the way they were working together to make their statements. They must have rehearsed their sales pitch beforehand.

“None.” The pharmacist replied proudly.

The hypnotherapist could see that Horace was interested and was ready to set the hook.

“What we propose is to train and condition the next few recruits into the department’s service provider ranks. We will demonstrate that our techniques can enable your professional trainers to condition the recruits with less than.04% behavioral variance.”

“I will also want to teach your in house therapists and hypnosis providers my methods that complement the susceptibility each recruit experiences when medicated.”

“So this vial contains enough medication for…” Horace let the question hang.

“That vial of liquid contains one dose.”

“So enough for one recruit?”

“Yes. One patient, one dose, administered intravenously; once a day for ten days and that is all the medication that is needed.”

“And ten days of hypnotherapy while the recruit is fully under the influence of the medication.” The hypnotherapist added. “A morning session of hypnotherapy followed by an afternoon session of sexual conditioning will accomplish in 10 days what takes the traditional training regimen 6 months.

Horace drew a sharp breath in surprise. “Sexual conditioning therapy is an advanced stage of training. Usually a recruit isn’t deemed ready until after 2 months of preparatory training.”

“Using my potion and her hypnosis your trainee will be ready immediately.” The pharmacist affirmed.

“I take it we have your interest.” the hypnotherapist declared confidently.

Horace decided to act decisively.

“We have a new recruit that may be perfect; a transferee from the Allegorian Penal System. He is slated to become a feminized service provider.”

Horace noted that both the hypnotherapist and the pharmacist raised eyebrows at this information.

“It’s an under-served fetish due to a shortage of acceptable service providers.” Horace elaborated. “This year’s national lottery only found one suitable candidate for induction.”

“Therefore I propose a test case, if you can demonstrate proof of conditioning for…” Horace looked to check over a document on his computer before continuing “Randolph James Johnson, then I will be willing do discuss a long term contract. We can compare his progress against the traditional methods we use on our one other feminized recruit undergoing training, the one who won this years lottery. Then see which one is most obedient. Agreed?”

The hypnotherapist and the pharmacist glanced only once at each other before responding simultaneously.

“Agreed.”

**

Randy sat in a comfortable padded chair. He gently tested the bonds that held him restrained and knew it was futile to struggle. Straps held his ankles in place. Another set of straps bond each leg at the thigh above the knee. A strap went over his lap and abdomen. Both his wrists were bound to the armrests of the chair and each of his upper arms were bound around his biceps. Another strap went under his armpits and over his chest. Another around his throat, and a final strap held his head back against the head rest.

Seriously, he knew before he even tried it would be futile. So he didn’t try very hard. It seemed the best choice to make at the time.

The therapist who greeted him for his induction and indoctrination into the National Social Services Acquisition and Maintenance Department had been kind. Her voice was sweet and soothing. When the officers escorting him from prison turned him over to the service she had insisted that he be treated kindly.

But then she had orderlies immediately escort him to this room and restrain him into this chair.

She said it was for his safety.

Randy was delivered to the NSSA&M still wearing his prison issue orange sports bra, booty shorts and pumps. They had taken him here directly from pillory. His feet and ankles were in agony from standing for so long in his blaze orange 6 inch peep toe pumps with 2 inch platform lift. Sitting down was a relief.

Once secured to the chair they had his eyes blindfolded; a spandex affair that sealed out all light from reaching his eyes. He was thrust into pitch blackness. He saw the room before they covered his eyes. It was dimly lit so all he saw was the chair and what looked like some medical monitoring equipment; nothing else.

Someone, he assumed it was a woman from the perfume he could smell; spent a fair amount of time attaching leads to him; on his chest, on his fingers, on his scalp, forehead and face.

Randy wanted to ask what they were about to do.

He couldn’t.

He bit down on the bridle bit gag that they had shoved in his mouth. He tried to force it out but it held snug by two straps, one over his head and one around the back of his neck.

He was embarrassed by the drool that was flowing smoothly down his chin and onto his chest. The drool was flowing slowly down the cleavage between his fake DD boobs. Prison issued breast forms for his public shaming in the pillory.

Once the technician finished attaching the leads there was a pause. Then someone pushed a needle into his arm. They left it there. He could feel tubing when they taped it in place.

Was he hooked up to an IV of some sort?

Were they giving him drugs?

Next a pair of headphones were placed over his ears; the old fashioned kind that covered the whole ear. Randy tried to shake them off but someone then strapped his head to the headrest of the chair and strapped the headphones in place.

After that it seemed he was left alone.

Randy sat and waited for something to happen.

Was the room getting warmer? Randy was a bit cold when he was delivered but now he felt warm. He was actually starting to perspire. For some reason he was very relaxed. Was it the IV in his arm? Were they giving him something?

Soft music began to play over his headphones right at the limit of his hearing. Randy strained to hear the tune. He found the more he strained and struggled to hear the harder it was…when he relaxed, the music seemed to get louder and easier to hear.

Something was happening…a voice…he could hear a voice saying something…repeating something…Randy relaxed more and the voice was easier to hear…

**

The hypnotherapist finished explaining the setup to the assembled NSSA&M training mistresses and technicians.

“As you can see our subject is in a sound proof room, completely restrained, isolated and deprived of most of his senses.”

“Sensory deprivation is part of the process?” An administrator asked.

“Yes…a necessary one.”

“We have raised the temperature of the isolation room to what we humorously call ‘womb temperature’. This with the sedative mix that makes up an important component of the drug will help to facilitate faster submission of the test subjects psyche.”

“I see that all of your instruments are here in this monitoring room. This is useful and important data that will be useful in proving the efficacy of this program.”

The hypnotherapist appreciated that the NSSA&M wanted to document the experiment and that they were monitoring the subjects heart rate, respiration, skin temperature, brain waves and a whole host of other instruments they insisted on using to monitor the test subject.

“You will find the uploaded app readout on this monitor. The app interprets the subject’s brain waves and senses reluctance or hesitation and follows a pre-programmed decision tree to compensate for and overcome the subject’s hesitation.”

The Hypnotherapist just smiled as she saw the patient was relaxing.

“The final component, indeed the most important and the only necessary equipment is this media recorder that contains subliminal hypnotic suggestions that are now being implanted into the subject’s thoughts.”

“As you can see the drug has been administered and entered the subjects system.” She began, pointing to the monitor that kept track of blood chemistry composition.

“The second part is simple subliminal suggestion.” She turned on the audio for her audience to hear.

“What you hear is this pleasant music. What Randy…er…excuse me, the subject hears on a strictly subliminal level is this…”

“You are a girl.” The soothing alto voice belonged to the hypnotherapist.

“You are a pretty girl.”

“You want to be a pretty girl.”

“You are good.”

“You obey”

“You obey your betters”

“You want to serve.”

“You want to serve your superiors.”

“You long to serve your superiors.”

The hypnotherapist turned off the speaker.

“The more he relaxes, the more pleasant the sensations he is experiencing from the drug, and the easier it is for the suggestions to take root. It goes on like this for some time, with subliminal suggestions expanding from the simplest suggestion to slightly more complex suggestions and conditions.”

“We’ve tried these techniques before.” One of the training mistresses interrupted. “There was no evidence that they had any effect on the subservient status of our subjects than those obtained by traditional methods of positive and negative reinforcement with the use of corporal punishment as appropriate.”

“Her hypnotic mental state coupled with the medication and these sequenced and organized subliminal implants will compel her obedience.” The hypnotherapist responded.

“Hypnosis cannot compel anyone to do anything that they wouldn’t normally want to do.” Another training mistress interjected.

“And that is exactly what makes our methods different. My method will build on the simple suggestions and expand upon them into more complex and elaborate conditions that the subject will encounter. She will first be conditioned to view herself as a feminized male whore. Next she will be urged to make a choice between two options. Finally she will face a series of conditions where she MUST choose and by then will be conditioned to follow her decision. She will have convinced herself that in the given circumstances her choice was the correct one and she must follow through. She must obey.”

“It still seems unlikely.” A monitoring technician spoke up this time.

“As they say, the proof is in the pudding” the hypnotherapist replied “In 10 days, you will see for yourself and I am confident that you will be convinced.”

**

The group reconvened later that afternoon as Randy was brought to the sexual conditioning center for his afternoon session.

The Hypnotherapist and the group had reconvened in an adjoining room and were watching the process of Randy’s conditioning with interest.

Normally a recruit would not be thrust into this situation until at least two months of training had elapsed. Having he subject receive sexual conditioning training on the afternoon of his first day was unprecedented.

The technician monitored the feedback from the EEG machine and was pleased with the results. Her subject was being thoroughly railed by the training mistress. The 7 inch long 3 inch thick neon pink strap-on dildo was fully penetrating Brandi’s ass and the pleasure centers of Brandi’s brain were lighting up the technician’s monitor.

The technician had studied the file of the subject in advance. Brandi, formerly known as Randy, had come to the Social Services Acquisition and Maintenance Department from the department of corrections after her court appointed sentence and reasonable punishment for gender based offenses was deemed to have been proven ineffective.

The technician’s attention was momentarily captured by an alert from the sensors embedded in the training mistress’s strap-on dildo. The pressure sensor was indicating that Brandi’s ass had finally relaxed fully and her ass was accepting the intrusion of the prosthetic penis. The technician noticed the graph of pressure resistance to time and found it to be within the “fast” end of the bell curve. It would seem that randy Brandi was a quick learner.

A special camera that was attuned to monitor surface temperatures was being used to monitor Brandi’s skin temperature and read the fluctuations caused by increased heart rate and respiration. Brandi was flush and her core temperature and skin temperature were clearly elevated from her exertions and the stimulation of her training session.

Not every male in the process of conditioning can respond to prostate stimulation so completely; or quickly, but Brandi was taking it like a champ. On all fours or on her back, in any position really, the prosthetic cock was able to easily stimulate her prostate gland with the result that the pleasure center of her mind was now being slowly flooded with endorphins.

Leads attached to sensors positioned to monitor her muscle contractions throughout her body were now indicating spasms and tremors of increasing frequency and intensity.

The technician smiled toward the training mistress and gave her a “thumbs up” signal. The subject was close to and about to orgasm from his…err, her…anal penetration.

The technician grimaced slightly, but for only a moment at her mental faux pas. Part of the sentence was that Brandi; formerly Randy was to only be addressed with female pronouns. Addressing her this way was also an important part of the conditioning process.