Jewel Ascending Ch. 02

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.