Ashleigh and the Governess Ch. 2

It became abundantly clear to Ash that he wasn't getting access to his money back – a week since he had stormed out of the Sisters of Diana building, he was still getting his credit cards rejected and hearing the same vague answers at the bank. Everything was frozen, and he wasn't authorized to dispute it. His entire financial life was entangled with the Caldwell company, so when he was forcefully separated from it he didn't have much else to fall back on. He lost the ability to pay for things online since that always took a debit card, and he didn't have a big savings of cash or much he could sell to raise money during this awkward time.
	His friends weren't much help, either.
	He got a few nights' sleep at his friend Marcus's house. But even though the guy had an entire mansion to himself, he quickly started making excuses about he wanted his 'space' and unsubtly implied that Ash should find another place to stay and soon. But Ash had been looking for other places to stay the whole time, just with limited success – Marcus was one of his last resorts. Additionally, Ash found it embarrassing to ask people for help since it made it look like he was looking for a place to flop after his stepmom kicked him out of the house. And everyone could see that he couldn't afford a hotel or an apartment of his own elsewhere. He was begging, and they all knew it.
	It was truly humbling for him to have to rely on other people to feed and house him, and he despised the sense of weakness he was projecting to everyone in his social circle. Soon, word began to spread that he was broke due to his arrest and his stepmother was taking control of things, and that embarrassed him greatly. His friends started screening his calls and texts.
	Dennis Pacher was no help, either.
	"I thought I told you to keep your step mom happy!" the lawyer said to Ash, on another one of their phone calls.
	"Yeah, be nice to my step mom!" Ash replied, "You didn't say anything about a fat, Arabic 'governess'!"
	Dennis laughed.
	"Kid, how can I say this to you any more plainly? They've got you hook, line, and sinker. I warned you against this exact situation, when you picked up your first check."
	Ash didn't have a reply for that. Maybe Dennis had told him. But when they had that particular meeting he was ridiculously high off of some edible brownies, and didn't remember anything except the amount of money he was getting each week.
	"You can't be telling me that it's legal for them to have me wear some kind of chastity device."
	"Guys aren't allowed to masturbate in prison!" Dennis said,
	"If you get caught doing that, they can put you in solitary or charge you with indecent exposure. Why would house arrest be any different?"
	Ash cursed under his breath. Dennis changed his tone.
	"Kid, I might not be able to talk to you that much, going forward."
	Ash had no reply. Hearing Dennis talk in this awkward, sad way it made his new reality even more clear.
	"They'll probably want to be your only legal representation. They will probably block us from talking -- that will be easy for them to do. Write me a post card if you need to get in touch. Maybe I can reach out to you through someone they don't know about. But there isn't anything either of us can do right now. Just keep your head down and do your time."
	"There's no challenge? No appeals?" Ash asked. It was sobering for him to hear a phrase that Dennis probably said to every one of his clients that got sentenced to prison.
	There was an uncomfortable silence.
	"No. You waved those already. I'll continue working on your behalf, but don't get your hopes up. I'm sorry."
	Ash saw that there was nothing more he could do and went home.
	**
	He saw right away that Aleksandra had been busy, this whole time.
	The home had a new security system built into it, and Ash's password didn't work with this one. He had to knock on the door and wait to be let in. He noticed a new car in the driveway, and was afraid that it belonged to Yusra. His maid Marisol answered the door with a smile and a level of confidence he had never seen in her before.
	"Welcome home Ashleigh!"
	"Thank you. Is Aleksandra here?"
	"Yes. In the living room. She said for you to see her immediately."
	Ash marched into the living room, thoroughly humbled. He saw Aleksandra and Yusra sitting on a sofa together eating finger sandwiches and sipping tea. They remained seated and looked at him with cold indifference like he was a peasant they were granting an audience.
	"I realize I will need to listen to you. So I'm ready to accept this program," Ash told them, his cheeks going red.
	It made them both smile, his Ukranian stepmother looked delighted. Yusra answered:
	"Good. You will start by giving us foot massages while we have our morning tea. Then Marisol will instruct you on the rest of your duties. From now on, she will be working as your supervisor to train you in her job. I've adjusted her salary to $75,000 a year due to her increased responsibilities."
	Ash felt his blood start to boil. They were paying his maid $75,000 a year so that instead of doing any actual work, she could just stand over him while he did her job? And the job consisted of being a servant for Yusra and Aleksandra, which he would be stuck doing for the next three years!?
	"Okay," Ash said, realizing that if he made a negative remark they'd probably just make things worse for him.
	"Good! You learn quickly. Oh before you do any of this, you need to put your new house arrest system on. Sashenka, you give to him now."
	 Aleksandra placed a aluminum briefcase onto the coffee table. When she opened it, there was a large glass and metal canister with something inside of it that was moving around trying to escape. Ash had never seen something like it before – it looked like a spindly rambutan fruit that could by rolling around on its many arms. He felt extremely uncomfortable when he gazed at this pitch black thing, which appeared to be using its arms like an octopus would its tentacles, to try to jimmy open the reinforced steel lid of the glass cylinder.
	"Here you go!" the blonde woman said as she gave him – he didn't know what.
	It moved like an animal sometimes and a machine sometimes. He had the distinct feeling that if he let this thing out of the bottle, it would kill him or do something very, very bad.
	"What the fuck is this?" Ash asked.
	"Here, easier to watch this video."
	Yusra queued up something on the TV. A Sisters of Diana logo appeared, then a woman in a lab coat started giving a talk about why they invented this product and pointing out things to help explain it better.
	"Our device completely stops any attempt at sexual misconduct," she said,
	"It is made with a bio-synthetic material – so it's more of a symbiote that bonds with the wearer's dermis so tightly that they are sharing a neural network. It can re-configure itself in many ways, changing the way it looks or feels. But above all else, this is a chastity device that will completely prevent the user from having an orgasm – all erections will be met with serious corrective pain."
	They looked at a computer image of the device with an X-ray filter on, that showed how it could 're-configure' itself to shoot microscopic tentacles into the person's genitals which gave it the ability to mimic and block sensation. Ash couldn't believe that such a thing existed. It horrified him to think that this malevolent thing inside the glass canister could take control of his body.
	"Please remember to put this on the subject yourself. I will demonstrate the pairing procedure now."
	Just when things couldn't get any stranger, the scientist lady walked over to a man completely in the nude, standing with his feet shoulder width apart and his hands clasped behind his head. He looked at the device with horror as the scientist approached with a flirty grin – Ash saw that she wore high heels as part of her outfit. He was clearly dreading this moment, but the scientist lady was giggling and thought this was all very fun. She lowered both of her hands down to his junk and the device practically sprang from her hands onto his genitals, smoothing its way across everything.
	The sound must have cut out – the guy's face became very red and he looked like he was screaming at the top of his lungs as the symbiote wriggled its way in. It looked horrendously painful. The guy was smashing his fists against the white floor of the laboratory, but he didn't make any attempt to touch himself. Finally, he found his composure and returned to his former position, except now his genitals were encased in the skintight black latex device.
	Aleksandra turned off the video.
	"You can strip down, now, and I will put it on for you."
	Ash just looked at her. She was pretending like it was normal, he was about to strip down completely nude so that she could put some torture device on his dick?
	"I thought we don't have to do this until we appear before the judge," Ash tried to argue.
	Aleksandra giggled.
	"Why? Do you want to masturbate a few more times before you put it on?" she asked, "No. You start working now. Strip. Marisol, you will bring Ashleigh some of his new clothes to wear."
	"Yes, miss," the middle-aged maid replied, walking away at a brisk pace.
	They were both looking at him expectantly now. And instead of arguing back, he surrendered and felt a wave of shame as he took off his shirt, then his pants, then finally his underwear beneath their watchful eyes. It was deeply humiliating for him to be in the nude before them, especially because --
	"It is so small!" Yusra remarked, pointing at his now-exposed cock.
	"Hush!" Alekandra replied, although it was clear she agreed with the woman,
	"Hands behind your head, Ashleigh."
	Ash felt a tremble in his lip as he took this obsequious posture. He had never felt more exposed in his life – air on every part of his body, genitals on display for anyone to see. Aleksandra came up to him and opened the sealed container, catching the black thing when it tried to jump away. She warmed it up by rolling it between her palms a few times (the way it stuck to her palms and made a squelching noise made him think it was an ooze) then she reached down to place it on her step son's cock. Ash felt totally violated; each moment was terrible and he knew this was wrong. His cock twitched as he felt a woman's touch, then the chastity device quickly began slithering its way to embed itself on him.
	It was a really strange experience at first, having this gooey latex fingers wrap themselves around his private areas, creating a tight prison for his cock. It made it so that he would notice the thing holding him back at all times, not just when he was getting an erection. By itself, the device wasn't painful exactly. It felt like many strands of of a slippery wet material had wrapped him up, and it had hardened into a skintight film that covered every part of his genitals. But then, the tight chafing feeling started to make him hard (even in the absurd circumstances of his stepmother standing over him laughing while it all happened).
	Then the pain came.
	It brought him to his knees – every nerve ending alive with agony like someone had taken a sledgehammer to his balls. He looked down at them, expecting to see that the device had malfunctioned and crushed them in a vise. But it looked completely normal: a flaccid cock, and balls encased in latex. It completely hid the excruciating pain he was going through right now. And the pain evolved: first crushing like a sledgehammer, then it turned sharp and stinging like a venomous jellyfish was trying to give him a hand job.
	"AAAOOW!" Ash groaned, in so much pain he couldn't stand.
	He would do anything to make it go away. Everything became secondary to the pain: he tried to grab the device and remove it, but that just made things work.
	"Please turn it off!" he cried out. He was getting spasmodic cramps all within his abdomen.
	"Ashleigh, you want to make it stop?" Aleksandra asked.
	"YES!"
	"This is how you make it stop: You need to kiss my feet."
	Ash didn't even have time to think about this. He dove towards his stepmother's bare feet and started kissing them with frantic devotion. True to what she said, each time Ash kissed Aleksandra's pedicured toes he felt the pain go down. It was a lifeline and he clinged to it, switching over to her other foot in hopes of getting more relief. It worked, but only up to a point: the pain had gone down, but only by a small fraction.
	"Ooh, is big one! Go kiss Yusra's feet, and beg her to be your governess," Aleksandra commanded.
	Ash, driven by pain (although less pain than when he began), crawled over to the smug woman and started showering her feet with kisses. Aleksandra's feet been long and slender, but Yusra's were smaller and more plump with decidedly lower arches and shorter toes.
	"Please be my governess, Yusra! I'm sorry for how I acted earlier!"
	The trend continued: each time he debased himself in front of these women, it would lessen the pain a little. But it had diminishing returns and even after he had bathed Yusra's feet in kisses for an uncomfortably long time he wasn't fully relieved; he was still wracked with a stinging pain like a bee sting but at several different points where the latex device touched his genitals. It was still terrible, but at least the cramps had stopped – and those were the worst.
	Marisol appeared with Ash's new clothes.
	"Now you will do that for Marisol, and it should be back to normal," Aleksandra said, "Marisol, please take off your shoes."
	"Oh that's not necessary, miss," the maid demurred,
	"Ashleigh had a rule that I must wear shoes because he doesn't like my stinky feet. I wouldn't want to--"
	"I insist," said Aleksandra, and that was that.
	With a cheeky smile, Marisol stepped out of her battered pink flats. Ash could smell her feet right away and it got worse the closer he got. How long had she owned that particular pair of flats? How many hours had she spent wearing them while doing physical labor in this house? Unlike Aleksandra and Yusra, Marisol's feet weren't freshly pedicured. But the smell is what got to him: sharp and pungent, specific to Marisol, right up in his face as he kissed her feet. She gave delighted laughter and had a good time with it. Finally, the pain stopped, and it sank in for Ash the reality of what he had done.
	He was kneeling on the floor naked (except for the latex device that now covered his cock), in front of three women and he had kissed all of their feet. The pain was gone, but seared into his memory. A pain so bad he would do anything to avoid it, as urgently as if he pulling his dick from off a hot stovetop. He started to put on the clothes that Marisol brought for him.
	It turned out to be a tight white camisole that went down to mid-leg, and something for him to wear around his waist: A black hostess apron designed with white rosebuds in the fabric, and it had white trim along the hemline and pocket line. Although it was nice to get clothes, he felt absurd standing in front of them dressed like an exhibitionist maid.
	"You will do our foot massages now," Yusra told him.
	Ashleigh, now wearing his uniform, knelt before Yusra and started massaging her feet with iris essential oil – the bottle seemed like it cost a fortune. Yusra and Aleksandra ignored him for the most part, except for when they'd ask him for more pressure, or berate him for doing the same strokes too many times. While he kneaded Yusra's soft soles, he felt his cock stir and was relieved that for some reason, the device wasn't punishing him for getting hard. Maybe it had a cooldown phase?
	That was how his training began. For the first several days, Ashleigh was either slaving away to clean the house to Marisol's standards, or else he was personally attending to Yusra and Aleksandra, mostly by massaging their feet. If he fell short of their expectations, he was punished. Marisol was ridiculously nitpicky about his work. She wouldn't tolerate the smallest error: he had to clean each room fully, sweeping and dusting and mopping everything even if there was no dirt anywhere because he had cleaned the room the day before.
	If Ash missed a single strand of hair, though, that was enough for Marisol to yell at him. And then she would punish him the way Yusra had explained: by taking one of her smelly flats and spanking him twice. He came to be mortally afraid of those spankings. While Marisol never hit him very hard, each time she spanked him the symbiotic device would pick it up and deliver excruciating pain to Ash's captive genitals. Like she was stomping them, even though she hadn't touched them at all during the two strokes she put against his backside.
	He was having a hard time learning the job, which entailed a lot more than cleaning. Marisol had an enormous list of things for him to do, always. She went so far as requiring him to burn sage and palo santo to cleanse Aleksandra and Yusra's rooms, along with other new-agey and time consuming rituals. Much of it was just mindless drudgery like requiring him to get on his hands and knees and finishing the entire floor with a microfiber cloth. And Marisol would always keep him up against a time constraint; she knew exactly how long it took to clean a room and she would give him just barely enough time to do each one as long as he really hustled. It was creating a constant sense of anxiety in Ash. He started to feel permanently haunted by the notion that he was doing something wrong – failing for some small but important reason when he desperately needed to do right by making Marisol, Aleksandra, and Yusra happy. If he displeased Yusra in particular, she would cause his chastity device to mercilessly punish his captive balls until he was crumpled on the floor begging for mercy.
	But the chastity part was more annoying.
	He didn't realize how much he thought about sex until the chastity device started stinging him every time he got an erection. He didn't realize how much he was masturbating and looking at pornography / cruising for girls until he couldn't do it anymore. It became absolutely frustrating for him especially because the longer he went without an orgasm, the easier it was for things to arouse him. To make the pain stop, he didn't always have to kiss Aleksandra's or Yusra's feet – sometimes he would be told to kiss Yusra's dirty panties, or her socks, or her collection of shoes. This resulted in him developing a weird fascination with women's undergarments: they gave him relief, but they were also a symbol of his punishment, and he really didn't like putting his face into one of Yusra's stockings she had worn all day as she ran errands.
	All of this was done under the Arabic woman's supervision and she was a very strict governess: Ash had to surrender his phone and was allowed no contact with former friends (not that anyone was asking about him). The whole of his life became occupied with learning to serve women, under constant threat of cock and ball torture if he displeased them. They had him clean out his room and pack everything into cardboard boxes they shipped away (or more likely destroyed). He slept in Aleksandra's shoe closet, with a few of her badly used yoga mats – the ones she used for hot yoga – as his only mattress and it made him sick to put his cheek in the indentation that had been created by her sweaty soles after hundreds of hours of yoga.
	On the third day, Dana Wellborne visited.
	Ashleigh answered the door as he had been trained to do: by welcoming her to the Lipka residence. He blushed when he saw the smile on Dana's face as she giggled at his tight little maid getup. She stepped out of her high heels and started giving him orders right away.
	 "Hi Ashleigh! I have some bags in the car, would you mind getting them for me?"
	Although frustrated that she was treating him like a servant, that was pretty much the reality of his life now, so he just nodded and did as she asked. The bags were large canvas totes from Sachs and Chanel. He didn't look inside but guessed they were shoes, and he brought them to the living room to set them down on the sofa.
	"It's really amazing what a difference that uniforms create. Don't you think?" he heard when he was walking in.
	"Would you like a foot massage while you drink your tea, Miss Wellborne?" Ashleigh asked,  freshly embarrassed that he was required to offer a foot massage to each of Aleksandra's or Yusra's guests now.
	"Actually, could you start with my shoulders instead? I'm really sore after my workout class. I'd really appreciate it!" Dana replied, sitting up straight so he could massage her back while she sat on the sofa he was no longer allowed to use.
	Ash nodded and walked over to behind Dana to start massaging her petite shoulders through the fabric of her dress. He immediately felt himself get hard as he touched this beautiful young woman, but the device started stinging him, and resisting him as he tried to grow. It was a warning, but how could he possibly stop himself from getting hard when he was serving her in such an intimate way? Her shoulders were lean and muscular, and she let out a very cute moan when he did a particularly good stroke around the crests of her shoulderblades. His reward was more burning pain in his cock as it strained valiantly to get hard within its prison – a pain which got worse the more excited he was.
	"I need someone like this in my office," Dana teased him as he moved on to do the back of her graceful neck.
	This became extremely painful for Ash – but it wasn't debilitating, so he was expected to continue his work and wait for it to subside naturally. He could smell Dana's hair and it made him feel intoxicated. He couldn't believe that he was in so much agony, while doing something to provide someone else with so much pleasure.
	"When are we set to appear before the judge?" Aleksandra asked.
	"Next week. It should be open and shut. Ashleigh will serve three years house arrest in this home, with work release privileges."
	"And what if he fails his treatment?" Yusra asked.
	"Then Ashleigh would go to prison, or at best a private mental Institution. If that happens, he might be on the hook for ten years. But obviously we will do everything necessary to prevent that, as his supervisors."
	Ash despised the way that Dana was pretending to be his advocate, when she was on board with this evil plan.
	"You understand, yes Ashleigh?" Aleksandra asked him, "For three years you will do as we say? Wearing your little... device?"
	"Yes," he murmured, not even looking up from Dana's narrow shoulders.
	If he said no, it would be like stabbing himself in the balls – although saying yes wasn't much better. There was nowhere he could run. After their brief discussion about Ash's case, they went on to chat about other things. None of them tried to include him in the conversation as they talked about their personal lives and social plans. After he finished Dana's shoulder massage, he stood nearby in case any of them needed something and they had plenty of further requests.
	"Can I leave my shoes here for Ashleigh to clean?" Dana asked at one point, "I'm trying to sell them online but I want them to look good before I create the listing."
	"Of course!" Aleksandra said, "I can have Ashleigh help you with that. He will even take the photos and do all the online work, if that would make things easier."
	Ash gritted his teeth at the fact that they were all talking about him like he wasn't here, and had no say in the matter. It was really a blow to his self esteem that Diana didn't ask him, but instead asked his step mother as though it was only her opinion that counted.
	"Oh my gosh, that would help me so much!" Dana said, then she turned to him and made a cute little face, "Ashleigh would you please do that for me?"
	"Yes, Miss Wellborne," he said, trying not to dwell on how tedious that job would be cleaning her shoes, then photographing them, then selling them online so that she could pocket all of the money.
	"Yay!" she cheered, clapping her hands together, "Oh, and I'm ready for my foot massage now. Thanks."
	Ash only allowed himself a moment of hesitation, then crossed over to the front of the sofa to kneel before Dana and rub her feet. He walked a little bow-legged and gripped his abdomen as a result of the aching pain still in his crotch – it felt like the device was deliberately allowing him to stay hard just so it could punish him for it, rather than trying to prevent anything. He took Dana's feet in his lap and started massaging them, noticing her French pedicure and the incredible softness of her soles. There were wrinkles around the ball of her foot that Ash was supposed to study, as though it might provide information on how to pamper her feet better. This was routine for him now: he was falling to his training that he had picked up from hours of doing this for Marisol in particular with all her Eastern healing modalities.
	"Have you decided where Ashleigh should work? Aside from here, I mean," Dana asked.
	"At the Norfax Tea Lounge. Definitely," Aleksandra responded,
	"My friend Adelaide owns it and she has been looking for a tea girl for ages. I really want her business to succeed, so I will send her Ashleigh to help. He can be the tea boy."
	All three women laughed at this, and Ashleigh blushed. The Norfax Tea Lounge was one of his stepmother's preferred places to spend her time. It was a popular meeting point for the women in the neighborhood where they could sip tea, eat little cakes, and take a break from their lives together in a comforting feminine space. She had dragged him there a few times and he never enjoyed it, although he could see the appeal. When she brought Ash before, he had felt like an awkward guest. But now he would be the help. He could hardly think of a more demeaning job title than, 'the tea boy.'
	And because it was a meetup spot for all the women in the neighborhood, they would all see him there working for minimum wage and tips, bussing tables and pouring tea and helping women with their coats. He would be waiting on women he knew personally, the sorts of gossiping real housewives who would judge him for doing such a 'low status' job when their own children had high-paying careers. The humiliation was almost too much to bear. And Aleksandra was so flippant about all of this.
	"That's a very good choice!" Dana gushed, "I'll make it so that Adelaide only has to pay Ashleigh at the prisoner's rate of thirty five cents an hour. That should really help her build her business."
	"Ah! I love it!" Aleksandra cried out, "But please also arrange it so that Ashleigh can come with me wherever I want and act as my driver, too."
	"Absolutely, I can do that," Dana said, "And I'll be at the Norfax Lounge all the time, so we can always meet there when it's more convenient!"
	"Marisol, please train Ashleigh on the responsibilities of a... tea boy," Yusra said, "And wax all of the hair on his arms and legs. I am tired of seeing it and I think the ladies at the tea lounge will feel the same way."
	Nobody ever argued with Yusra when she gave an order. Marisol curtseyed to her employer and said that she would add that to Ashleigh's training regimen whenever Yusra wanted. Ashleigh certainly wasn't looking forward to doing 3 years of slave labor in these absurd circumstances, but he really had no choice. His relationship with Aleksandra had changed so quickly; she was totally comfortable ordering him around like he was her lowliest servant and she treated him as just that, which was extremely different from how warm and gravious she treated her friends right in front of him. She had so many frivolous needs, and he was now stuck trying to satisfy them all while she just sighed and frowned and just found more reasons to boss him around and punish him. And what would Adelaide bring to his life? How his friends and their parents react when they saw that he was on probation and house arrest, working off his debt to society in a menial capacity beneath his stepmother's thumb?
	He couldn't even imagine people finding out about the chastity device. With nothing to look forward to, Ash applied himself to learning the job so he could at least avoid getting punished.