Ashleigh and the Governess, Ch. 5

She watched everything he did, remotely, with the help of all the security cameras built into the tea house. She especially liked the part where he went down on Julie in the break room and she had watched it several times. Aleksandra was ecstatic to be pimping out her own step son like this, especially because it meant that he was already open-minded to the idea of sexual servitude. She knew a few similarly open-minded women who would adore such a devoted tongue – they might not even think about it as cheating. Not when they saw his little device, and all the other things Ashleigh would do for them.
	It was meant to be devastating to his ego and judging by the shell-shocked expression he had for a while afterwards, it was working. Julie had been so easy to recruit into the plan. She liked that he was trapped somewhere – it made her feel that he was in a cage she could visit any time she wanted. Ash would have to receive her, and pay her attention, and dote on her on top of being a perfectly attentive lover. Although she had a full and active work / social life, she was thrilled for the opportunity play her part in Ashleigh's therapy. She happily studied the code of conduct the Sisters of Diana gave her, and was effusive about how much she agreed with their mission.
	It was risky for them to reach out to her.
	Yusra had been against the idea.
	"We have an entire team of ladies who do this exact same thing," she argued,
	"And we can be sure of their loyalty. If we get his little girlfriend involved this soon, she might double-cross us because she gets feelings for him again. I have seen this happen before."
	Aleksandra didn't care about the risk. She was possessed by a need to rub Ashleigh's face in his past this way; she knew it would satisfy her infinitely more seeing him do this on a girl he used to mistreat rather than an actress or whatever stranger Yusra had in mind. Eventually, she won out because Yusra realized how attached she had become to seeing this.
	"We can reach out to Julie," Yusra relented, "But none of his other exes. Not yet. And we will need to fully indoctrinate Julie into our thinking – she can cause damage unless she goes about things in exactly the right way."
	    Aleksandra kissed Yusra on the lips, and hugged her in a show of gratitude and affection. Arguments were foreplay for them most of the time, and they started kissing like teenagers in the midst of plotting poor Ashleigh's downfall.
	It was a potent aphrodisiac for Aleksandra, and Yusra turned out to be the perfect level of dominant towards her during their lovemaking. Sometimes Aleksandra felt that the imperious woman would take things too far; but this time it was very good. Now the Ukranian trophy wife with skin like porcelain was lying back so Yusra could finger her and whisper things in her ear that made the hair on the back of her neck stand up. She was constantly surprised at how well Yusra could play with her pussy – it was like the woman could read her mind and knew exactly how long to tease her, and when to rub frenetic circles against her clit with one thumb, while her middle finger reached inside to stroke her prominent G-spot with a very particular motion made her cum every time. Then Aleksandra would always grab the silk sheets between her long slender fingers, and arch her back as a stunning orgasm took over her senses and she never felt more like a queen.
	She never reciprocated the favor. Their relationship had an unspoken rule that Aleksandra would only be touched, and wouldn't touch Yusra very much in return: an excited squeeze perhaps, or a kiss or a bite but never penetration and certainly not oral sex. It suited her purposes; she had always been a pillow princess and didn't feel much desire to do that to another woman. Yusra's tongue was even better than her fingers, but she was a little more selective about when she would do that.
	It had occurred to her that Yusra might be sexually conditioning her the same way they were Ashleigh, but there was no one in her life she could talk to about it. She watched the video again, taking a newfound sense of enjoyment from Ashleigh's defeated body language as he put his head in Julie's lap to do something he didn't like. The symbiote must have been driving him insane.
	She drafted a mental list of the women who'd be most likely to accept this service right off the bat. Loretta would absolutely do it, and so would Penny – they were always whining about how men didn't take the time to satisfy them so Ashleigh would be a gift-wrapped solution to that problem. Others would be accepting but to different degrees, to begin with: their neighbor Hilda would definitely accept Ashleigh as her weekly housekeeper, and she would be fine with the boy hand-washing her panties but she would probably draw the line at having him hold them open for her to step into or any of the rest of the more intimate dressing duties.
	Aleksandra watched the video one more time of that beautiful scene of Ashleigh getting on his knees for a girl, then she had to get back to 'work.' At the Sister's request, she had to constantly be seeking out and creating new ways to demean and humiliate the boy, otherwise they ran the risk of him normalizing the experience. It was a relatively small risk, to be honest, and this practice was from before they had invented the chastity symbiote which made conditioning people trivially easy. But Aleksandra only needed the smallest excuse to make his life hell. Now, she had her cinder boy who could never run away, and just had to bow his head and work that much harder to make her happy. She luxuriated in the feeling, and now she had a desire to share that feeling with others.
	She and the Sisters had an enormous pool of talent to pull from.
	As Yusra said, they DID have ladies on the payroll whose job was to teach clients how to be very good at giving oral sex. Some of them were cosmopolitan, Harvard-educated types like Dana Wellborne but others were exotic dancers and even some financial dommes and sex workers looking to get into a different line of work. That was part of their outreach: a program they offered to save women from having to work as prostitutes... by having them use their bodies to teach sex prisoners how to eat pussy better in exchange for a paycheck from the Sisters of Diana. Most of them saw the irony but they didn't care; they were getting $100,000 a year in taxable income for a tiny fraction of the work they were doing before and they couldn't be hassled by the police or by the clientele.
	That was just one branch of their outreach. The Sisters of Diana had companies in every industry but the ones that interested her the most right now was their contacts in housing, media, and market research. They made it so easy for her to execute her plans that all Aleksandra had to do was describe what she wanted and they did all the legwork to make it happen. One thing she described came to be a startup called Lucia that was meant to address the housing shortage in their city.
	She was basically converting her home into a large-scale dormitory / hostel for women, with very attractive rent prices and maid service included. In all the promotional material, they emphasized that things like massages, facials, and pedicures would be available at any time for an extremely reasonable price – fifty cents an hour, at most. They had received a flood of replies and now they had to screen people to see who was the best fit. One of them caught her eye: her name was Dasha and she was an unusually light-skinned Pakistani woman who said that she had grown up with servants, and would be very happy to live in a house that had them in America.
	Aleksandra looked through her photos. Dasha's family had an estate rose farm in Pakistan that clearly earned them a lot of money. In one of her photos, Dasha was sitting on a chair that was being carried on the shoulders of four different men. Someone like that could be a fantastic member of the house because she could model how to treat the help in a more antiquated way.
	Another one of the applicants was a quasi-celebrity. Elizabeth Alsace, who was the half-sister of Mara Alsace – that actress who was in all the papers when she married a prince and had a royal wedding. Aleksandra could see the jealousy on Elizabeth's beautiful face in every photo she saw of the woman. Elizabeth was active in new age circles and did things like yoga retreats and crystal healing, although she never seemed to be in a good mood for all her efforts. Even if Aleksandra was wrong about Elizabeth having a deep-seated anger that her sister had married a prince and not her, she was still the sort of high-maintenance rich girl that she wanted to keep around. Unlike her sister, who was brunette, Elizabeth had platinum blonde hair and she was considerably more tan. It was like she wanted to look radically different from her au naturale sister, so that she didn't mind if she looked a little basic.
	Those two would probably get invites. With that decided, she turned away from Lucia towards another project she was working on. She thought about it when she looked at the large, nondescript canvas bag in the corner of the room. How she looked forward to Ashleigh's face when he opened that little 'gift!' Inside of the bag, each contained within its own zip-lock bag to prevent the odor from contaminating the whole room, were leather ballet socks. Not just any socks though: each pair was nearly 'dead' from use – from the countless hours of athletic young women dancing and working while wearing the canvas leather-soled footwear. On a wild hair, she decided to open one of those ziplock bags to get a glimpse of what Ashleigh would suffer through and she couldn't even bring herself to remove the shoe from the bag!
	It was Yusra's idea. More demeaning busywork for their little prisoner: she wanted him to clean these dance shoes using only his tongue, paying great attention to the insoles. She would only be satisfied when he had stripped down the entire insole layer by layer– licking it again and again to remove the dirt and sweat and oil that had accumulated in there. But that wouldn't be enough. He would then need to detail the little indentations that had been created by the women's toes, leveling them out as best he could. And what should he do with all the dirt and detritus that came off of the horrid things? Swallow it, of course! And nearby they would give him a little dog's bowl of water so his tongue wouldn't try out. They could add drops of an Indian essential oil known to change the way people taste things to the drinking water, so every part of it would be more foul and unpleasant.
	If he misbehaved, or if he failed to meet some capricious deadline, they had a few ways to punish him on top of what the symbiote would automatically do. Aleksandra was wealthy enough that she could dump out the water altogether and just fill the dog bowl with thousands of dollars worth of pure Gymnema sylvestre oil to make it unbelievably potent. She could not imagine how that would affect him; but she very much wanted to see it. Or to switch things up, she could dump liquid capsaicin into the bowl – the chemical that makes food spicy -- so that he couldn't help but cry as he did it. Here was the extent of her mercy: that she would allow Ashleigh to use two of the filthy ballet slippers as kneeling pads while he worked because of course he would have to do it on his knees. Maybe somewhere in view of Aleksandra, but far enough away that she wouldn't be subjected to the smell.
	She loved how futile it all was that Ashleigh was trapped doing this odious labor, and he got nothing to show for it in return except staying out of jail. She had 25,000 opportunities to find some reason to correct him but even if he did it all perfectly, so what? She or Marisol would examine the shoes, then throw them in the trash, then he would move on to the next pair, chop chop! She loved that he had no choice but to accept the things she ordered him to do – the sense of power Aleksandra felt from this was better than being in love, better than any drug. She could stay high like this for weeks, for the rest of her life.
	Aleksandra realized she was daydreaming, and chose to give Dana a call.
	"How are you Aleksandra? It's good to hear from you!" the attorney said with genuine warmth.
	"I am good. Would you like to play tennis with me tomorrow?"
	"Yes, absolutely!"
	"Excellent. I will have Ashleigh there too, he will act as our ball boy. I have a very cute outfit for him to wear."
	Dana laughed.
	"Is 11 AM okay?"
	"Sure."
	"Hey while I have you on the phone," Dana said, "We are ready to move forward on your silent auction idea... I've already heard back from several celebrities who are happy to donate a pair of shoes. It will be a lovely way for you to debut the Lipka Organization."
	"Yay! I am so excited! Has the payment come through?"
	"Yes," Dana replied, "And thank you for that. I'll get the ball rolling, and we can start planning to put something on, by end of next quarter."
	"I earmark two hundred thousand dollars for you to use for the silent auction," Aleksandra said.
	It was designed to be a a high-dollar fundraising event; but more importantly it was a way of draining the Caldwell finances and funneling them over to the nascent Lipka Organization. The Sisters had done some legal jiu-jitsu where one company took out a loan, then gave it to a charity that it also controlled, then got a tax break for making a charitable donation and thus created money from nothing. With the added benefit of legitimizing Aleksandra's reign over both companies – everyone would see where she stood, and the new role Ashleigh would serve in the company.
	"Thank you! I can't wait. See you tomorrow!"
	Aleksandra Lipka went back to work, doing the more mundane aspects of managing a real estate business. Ashleigh was a big part of her life, but like every woman in his life she had a vast social universe outside of him. Ashleigh on the other hand, had nothing except for her, and the people she appointed to manage him. It was exactly the sort of power disparity that she liked in her life; shrinking his world down until his main concern was the dirt beneath her fingernails and the way she liked her tea.
	**
	Ash had not been more mortified in his life when he saw the outfit that Aleksandra wanted him to wear at the country club. He looked like a deeply confused boy playing at being a ballerina: he had on a white long sleeve shrug that covered his arms up to the shoulders but didn't go any further down his torso than his shoulderblades. The thumbs of the sleeves were cut out, so that he could show off his sparkling white manicure. The other parts of the outfit were a white leotard and a pull-on skirt that would cover his obvious bulge. The skirt had a white-to-blue ombre pattern, it would really draw some looks. An oversized baseball cap completed the look, and he was at least grateful that the large visor would cover his face from certain angles. Between that, the big fashion sunglasses, and the fact his hair was in a ponytail pulled through the back of the hat, Ash figured he was incognito.
	 Ash didn't say a word to anyone at the country club but he could feel every time someone looked at his ridiculous outfit. He tried to hide behind the womens' gym bags he was carrying as they sauntered through the lobby saying hi to people they knew. Nobody addressed him, but he stood out like sore thumb looking like a girl sailor / ballerina while everyone else was dressed upscale casual or business formal. He felt incredibly at risk, like he was in a fragile bubble of anonymity but as soon as it popped and someone recognized him, he would be a laughing stock. Then his thoughts darkened; he realized that at some point Aleksandra would expose him.
	She just wanted to tease him for a little while, first.
	His cock was lifted so that it pointed towards his bellybutton and kept in place there by the symbiote. It started to transmit sensations in such a way as to deceive him and give him the feeling he was exposing himself to people. It did this by mimicking the sensation of cool air blowing across his balls with every step. as though his skirt weren't there, and this made him ludicrously self-conscious. Although he saw some people he knew, they got to the court without anyone recognizing them. They at least let him keep his head down along the way.
	"You will be ball girl," Aleksandra said to Ash, "You know what this means?"
	Ash was vaguely familiar. That was the lowly-paid person who stood on the side of the tennis court and dashed out to fetch the ball whenever it hit the net or went foul, then threw it to whichever player had the next serve. The country club was always hiring for the position because nobody seemed to want it. He was sure there was a more modern name for it than 'ball boy' or 'ball girl' though.
	"Yes," he replied.
	He helped them with their shoes and socks first, then got ready to attend their game. The first problem was the fact that he couldn't stand around while he waited to be used. Aleksandra made him take the position he would have to take if they had photographers at the game: on his knees with his hands out touching the ground in front of him, so that his face was near the cement and his bum was high up in the air. It made absolutely no sense, and it was painful to maintain but both Aleksandra and Dana would laugh when they saw him take this pose, so he knew he would have to keep it up.
	When he had to retrieve the ball, he couldn't run at it like they did in the tournaments. The only 'valid' way for Ash to move (IE, the only way his symbiote didn't punish him for attempting) was by emulating a catwalk model. He needed to keep the head high, shoulders back, arms swaying naturally, to walk in measured steps and to maintain a focused gaze. Ash could only walk so fast, which lead to the absurd situation of the ball outrunning him while he was walking after it – Aleksandra roared with laughter to see it. It created an obvious delay of game which drew all the more attention to them. Anyone could be watching.
	When he finally got to the ball, he had to raise it high above his head, then roll it on the ground to whoever. He was not allowed to throw it. Sometimes they would make him kiss the ball for luck, or walk it over to them. He also served as their towel and water attendant, bringing their bottles out to them whenever they were thirsty and holding spittoons when they just wanted to rinse out their mouths. It was not enjoyable work for him, but he was at least thankful to be out in the sun. Better than being locked in the shoe closet, certainly.
	Ash had to be extremely conscientious of how he used his hands during all of this work, because the shimmering white nail polish was still wet. It wouldn't dry at any point: it was the special sort of polish that only dries beneath a specific kind of LED light. This was a way for Aleksandra and Yusra to 'test' him, and he could expect a severe punishment if he so much as smudged a nail. It was nearly impossible to fulfill this whim of hers. How was he supposed to unlace her tennis shoes, and take off her ankle socks, then do a foot massage for her and put her shoes and socks back on, without a nail touching something at some point? All it took was the smallest brush.
	Nor did Aleksandra try to make him fail. She patiently sat and watched him unlace her shoes with surgical attention, then take off her steaming hot socks like he was disarming an explosive. She found it very entertaining, and was just catching up with Dana and enjoying her day anyway so the lag didn't matter.
	"Ashleigh, you keep wrinkling your forehead. Are you aware of this?" Aleksandra asked the boy as he carefully massaged her alabaster feet during half time.
	"I must be worried about something."
	"We will get you Botox," she said decisively, "I do not like to see you frown."
	Ash couldn't believe her nerve, but had to keep rubbing her feet all the same. She would rather inject venom into his face just because she didn't like to see his honest emotions? It was yet another freedom she would take from him.
	"And maybe we'll get you some lip fillers, while you're there."
	With the utmost care, he tried to slide a new pair of socks back on her feet, but he smudged a nail. By his frustrated sigh, she knew what happened.
	"Ah. Is too bad," Aleksandra told him, placing a sympathetic hand on his shoulder.
	"Okay. For punishment, we will do the no urination for four hours. Starting now. Go to the drinking fountain and have all the water you can drink."
	The next for hours were so bad, Ash could barely stand it. The 'no urination' trick was like this: he drank a lot of water then the symbiote prevented him from urinating except for the tiniest dribble once every few seconds. To accomplish this, it was constantly manipulating his dick so that it would trickle out a few drops then stop – it was a maddening sensation, stopping himself from pissing so frequently. It made literally everything worse and every moment seemed to stretch out as he was subjected to this awful torment.
	He was grimacing for the rest of the game, and he dreaded to think about how much worse it would be when his face was stuck in a neutral expression no matter how much pain he was experiencing. With his head on the ground, all he had to look at was Aleksandra and Dana as they played tennis in their expensive outfits picked to show off their bodies. Even with all the pain in his knees and bladder, Ash was very sexually frustrated and he thought Dana had a fantastic body glistening with sweat, radiating heat as he touched up her sunscreen. Then he would become aroused about her, which the chastity device would punish him for in tandem with everything else going on.
	"Some men would have chosen to go to prison if they were in your situation, Ashleigh. Have you ever considered that?" Aleksandra asked him.
	He shook his head. She giggled in response. She had her feet in his lap and was receiving her post-game foot massage. She had beat Dana handily and was in a good mood. His stepmother was sitting on a padded bench with her long legs stretched out, watching him work.
	"Some men, they would have simply taken the years in prison," Aleksandra continued, "I know several men like that. But not you. This is what you chose instead, to dress up for me and to live under my rules. What does that say about you, as a man?"
	She let the question hang in the air. It was something he struggled with a lot: that people must think him a coward because he was doing all this to avoid prison. He was putting on pretty skirts and massaging his stepmother's feet to avoid his punishment; a far cry from the way a more hardened man would approach jail time. Wasn't that what Aleksandra was always communicating to him by the way she made him dress and act? That he was hiding behind his stepmother's aprons because he was too fragile and pitiable to do anything except pour her tea and clean up after her? But he knew prison would be worse, so he stuck it out.
	"I am happy for your help today. But you still are not acting grateful enough to me for helping you stay out of prison."
	"I am grateful!" Ash lied.
	He got uneasy every time she brought up the subject of 'gratitude'. It usually meant that she was about to punish him and was coming up with a pretext for doing so. His anxiety was through the roof.
	"Then how come you did not seem happy about the news? That the Caldwell group is investing in our company ten million dollars?"
	He just couldn't do it. He couldn't act happy about that, not convincingly. Even now he could only force a plastic smile that didn't touch his eyes. He had assumed there were guardrails in place that would stop Aleksandra from making major expenditures like that, but apparently not. When he thought about the Lipka Organization he would nearly suffer a panic attack. He couldn't act happy about this pure embezzlement scheme any more than he could act happy if he were swimming in the deep ocean and saw a big shark fin coming right at him.
	"I'm happy that they could fund such good charities," Ash said – he knew that Aleksandra expected him to lie, but he didn't know what she wanted to hear.
	"Maybe we will have you help by handing out invitations to people, here in the country club."
	"It's certainly a good idea, doing a silent auction with used clothing instead of stuff like artwork, or gift baskets," Ash said, trying to change the subject.
	"Thank you!" Aleksandra replied.
	To Ash's relief, this got her talking about the fundraiser instead of the idea of him handing out invitations at the country club, dressed in some mortifying outfit.
 	"Yes I wanted it to be very easy for the ladies to participate. Everyone has an old pair of shoes lying around. The Roseborough Ladies Ballet Company donated their slippers and toe pads from their award-winning performance. And we have contributions from smaller dance schools – along with pairs from models and actresses."
	Ash could not fathom who would want to buy such a thing especially at the prices they would be aiming for: $100,000 for a pair of boots that some actress wore in every scene of a zombie TV show? Bids could easily get to six figures, they were supposed to get that high. How could Aleksandra seriously be planning on having a black-tie fundraiser, where the only thing to bid on was women's badly-worn shoes that somehow cost or raised ten million dollars? It was a mystery to him, but a malignant one. She kept him massaging her feet and calves for an annoying length of time until Dana said that she needed to leave.
	"We will get you the botox today, while we are out. And the lip fillers too. Dana, do you want to come with us?" Aleksandra said.
	"No thanks. I have to get back to work. But I'll stop by the tea house soon. Thanks again for helping to sell my shoes, Ashleigh!"
	Before they could leave, some other people came on the court. It was a women's volleyball team from a nearby private school. Ash was struck by how tall each of the girls were; they were a closely-knit team wearing grey and blue uniforms.
	"Is this the new ball girl?" one of the tennis players asked. Before anyone could answer, she went on:
	"How is your sports massage? I have three girls with very high arches and it's giving them neuroma pain in their feet. Could you start by warming them up, then you can help the rest of us do assisted stretches? I'm Sylvia by the way. I'm the captain."
	"I'm sorry, Ashleigh is coming with me right now," Aleksandra replied, "But she can help you very soon. Which school are you with? What days are you here?"
	It struck Ash that Sylvia cut him out of the conversation and was just talking to his stepmother on his behalf. Why did people always do that, even those who weren't 'in on the game'?
	"Tuesdays and Thursdays at about this time. But we have smaller practices too, and early morning stuff. Let's stay in contact. Nice meeting you."
	  Ash bowed his head to her and they all said goodbye. Aleksandra drove them to the plastic surgeon's office next. She made him change outfits to something a bit more reasonable before they went in. Along the way he made random, erratic motions with his brows and forehead to enjoy the freedom of expression for the last few moments he would have it.
	'This is a mixed blessing,' Ash thought to himself in the lobby of the medical office.
	It was an extremely upscale place catering to self-conscious rich women, probably some of the best surgery money could buy.
	'I won't be able to frown or wince or do much of anything. But on the bright side, at least Yusra won't be able to drill me so much on making feminine facial expressions instead of masculine ones.'
	Yusra had given him some lessons on that subject, teaching him to act like a naive youth who was impressed by anything and was infinitely happy to be bossed around all the time. This particular lesson didn't come to him very well, and he supposed it was easier to just be locked in to a 'resting bitch face' than to have to practice all these adroit, supplicating facial expressions that Yusra wanted him to make all the time.
	The visit with the doctor was different than he had imagined.
	First, he met with someone other than the plastic surgeon. The first woman he met introduced herself as Dr. Maeve, and she was some kind of speech pathologist. She held out a microphone and asked him to repeat sentences out loud after her. Although he found this strange, he wasn't about to go against a doctor's orders especially not with Aleksandra there.
	"When men speak, they tend to use loudness to emphasize what they are saying," Dr. Maeve explained, "But with women, it's more about pitch and variability. I'm just trying to get a baseline of your speech: things like pitch, and prosody."
	She put her hands on his throat to feel his lymph nodes, and the touch felt nice even if it was in a clinical setting. Was that the next thing Aleksandra would have him do? Learn to speak in such an efette way that it further influenced the way people treated him?
	Dr. Maeve left pretty quickly, and another doctor came in to do the Botox in his forehead, around the side of his eyes, and some lip fillers. Aleksandra watched all of this happen with a great interest but Ash didn't like having her there. The way she was looking down on him was so vindictive, like she enjoyed this for all of the worst reasons.
	"Thank you for getting this procedure for me," Ash said to his evil stepmother.
	She giggled to herself.
	"You're welcome Ashleigh! You are going to be an ambassador for the Lipka Organization. So it is good for us if you look a certain way. No more frowning!!"
	She said it like it was a joke. His forehead was numb and so was the area around his eyes (they had given him Botox there too for 'crow's feet')  so he couldn't even pretend to laugh. Instead, he meekly said, "that's funny," and it satisfied Aleksandra.