He is Your Master Now Pt. 06

At the start of his first full day at the mansion, Ambrose decides to submit himself to whatever fate Cassilda ultimately plans for him, even though he is still daunted by whatever that fate might be. As a result, his stress is greatly reduced. Then, a new, unforeseen player arrives and contributes to his newfound mental well-being, even as she works to facilitate Cassilda's plans for him. Through it all, however, like a shark unseen in the cloudy distance, there remains some fear.

He is Your Master Now Part 6: Going Deep.

The kitchen was brightly lit courtesy of the morning sun pouring through the windows. Ambrose expected to find Governess Bishop there, but she was nowhere to be found. Instead, he found Governess Goode who had traded her vintage nurse's uniform for a vintage maid's uniform. Unlike Andrea's sexy maid's outfit, hers was strictly practical.

Aside from being a nurse, she was apparently a good cook. The pancakes she served him were arguably the most delicious he ever tasted. There was a quality to them hard to define. "Organic" came to mind, but that didn't seem to cut it as there was a heartiness to them that bordered on the sinful. They seemed to be as out of place in time as the governesses; as if they were from an time when people had the kind of short burdensome lives that placed worries of cholesterol and heart disease well out of reach of their concerns.

They echoed an era when even if one's meal was not as rapturous as these pancakes, no one ate mindlessly. They savored their food regardless of quality and thanked whatever god or gods they worshiped for the simple reason that they had something to eat.

For a few short moments, Ambrose managed to lose himself in the sensuality of texture and flavor in what should have been simple fair, but it didn't take long before his thoughts turned to the painful memory of his "deflowering" from the previous night--- indeed from all the events of yesterday.

Soon he was worrying over what was to come. There was a real concern that perhaps the peace that finally stilled his mind and allowed him a merciful sleep was only the result of a fatigued mental state, and not because Cassilda had accepted his very sincere oath of fealty and calmed him somehow with her bewitching talents.

Movement at the corner of his eye caught his attention. He turned toward it.

A somewhat tall woman, about thirtyish, was walking toward him. In keeping with the Governesses' penchant for vintage clothing, she wore garb that could best be described as that of a stylish professional woman of the 1950s: a grey form fitting skirt with a slightly contrasting line pattern with large black buttons running down the length on the left side. She wore a matching woman's business jacket over a navy-blue blouse. As she came closer, he could see that some of her height was due to tasteful high heels designed to accentuate her legs while still retaining an air of professionalism. She wore sheer black nylons and sported a pearl necklace as well as pearl earrings.

The fact that she was not wearing a pillbox hat with a net veil draped over half her face, or dainty white gloves didn't stop his imagination from trying to see them.

"Ambrose Sweet." She walked over to him and stood looking down at him for an uncomfortably long time. When she cocked an eyebrow at him, Ambrose stood, realizing that he was expected to stand and greet her formally.

She smiled pleasantly and extended her hand assertively. They shook hands and she motioned him to sit again.

She turned to Governess Goode and dismissed her with a polite "We won't be too long," after which Governess Goode left the kitchen with a respectful nod.

"My name is Cheryl Benson, but you can call me Pippi; everyone does."

Ambrose suddenly felt a tinge of unease. He didn't relish meeting a new person, having to figure her out, order his behavior to account for her existence, accommodate whatever she had in store for him, and then worry about how much clout she had with Cassilda.

Pippi pulled up a chair and sat on its edge, across the corner of the table and leaned in just a bit too close to Ambrose.

"So--- what are you?" He asked cautiously.

"What am I?" she asked in mild but amused disapproval.

He wasn't really in the mood to be on his toes so soon after last night.

"I mean--- what--- who are you to me." He sighed in agitation at his own rudeness. He should know by now that in anything involving Cassilda, it was best to be as polite as possible.

"You seem a little agitated and nervous; I don't know how to interpret that. But in answer to your question. I'm a trainer of sorts." She had a briskly assertive way of speaking.

"Trainer? I don't even know what to expect anymore so whatever---."

Pippi seemed surprisingly pleased. "That's about the best response I've could've hoped for."

"Why?"

Ambrose could detect no change in her body language before she answered, but he still got the sense that she focused on him more deeply as if to gauge his reaction to what she said next.

"It means you have no fight left in you and that makes my task a lot easier."

He didn't like the sound of that but he couldn't summon a modicum of rage. This was partly because in spite of his newfound calm, he was still a bit wary, and partly because he knew she was right. What's more, he had a sense that everyone associated with Cassilda was aware that he knew he had no fight left.

"While my job is to train you," she continued, "let me reassure you that we won't be having quite the adversarial relationship as you have with Bishop. Even so," she added soberly "you should keep in mind that we both have to answer to Cassilda."

"Train me for what?"

"Train you to be perfect for---" she paused a little overlong to let his imagination ponder the possibilities, "---Cassilda. I'm here to perfect you for Cassilda."

She relaxed a bit. "Cassilda considers you akin to an unfinished work of art. With that metaphor in mind, it's my job to chisel away at any excess that would spoil the poetic balance of the piece in its final form. I then proceed to smooth out the rough spots, and ready the piece for presentation by providing a fine polish.

"I'm going to ask you something Ambrose. And I want you to pause long enough to give serious consideration to your answer. You should also tell me the truth because you know I'll be discussing you with Cassilda and she has an insight into you. Well, she has an insight into all of us actually, like no one else in our lives ever has or ever will."

Ambrose nodded. "Go ahead and ask."

"How easy do you want things to go while you're here?"

"I can't answer that question without knowing details about my---" he added finger quotes, "'training'".

"Fair enough. Let me ask you then. When you look back on all those particular things you did because of Cassilda that wound up causing you some unpleasantness, do you see now that you made them more unpleasant by resisting, by having negative thoughts and just generally being ungrateful?"

"I suppose it's more pleasant to hand over your wallet to a mugger than having it taken from you."

"Hmmm" she muttered amusedly and paused. "That's a lot more cleverness than I would have expected from you. That's also a negative thought and unhelpful. But let's explore that metaphor anyway.

"Let's say Cassilda is the mugger, and that her plans for you are the equivalent of stealing your wallet. Metaphorically speaking, you should consider that if you tried to stand up to this mugger, that perhaps you stood no chance of landing even a weak punch. And that perhaps this metaphorical mugger overcomes your resistance by handing you a nasty beating --- again, metaphorically. Then he simply takes the wallet off your unconscious body anyway, leaving you in such a state that you'd probably require medical attention. Perhaps you might even suffer permanent injuries.

This is all metaphorically, of course. Metaphors are almost never perfect. In this instance, this hypothetical mugger wouldn't be providing you with a very comfortable lifestyle and the most mind-blowing sex you've ever had.

"So, I'll ask you again Ambrose. How easy do you want this to go?"

"I'll do whatever I have to do."

"And what does that mean? Remember, we're speaking metaphorically."

"I'll--- just--- hand over my wallet?" He asked, hoping it was the correct answer.

Pippi smiled, looked down at the remains of his breakfast and saw that Ambrose, like a child, had so saturated his pancakes with maple syrup that a tiny pond of it had pooled to one side of the plate. Unexpectedly, she leaned even closer and ran a middle finger through it until it was thoroughly coated with syrup.

Ambrose assumed that she meant to taste it which struck him as odd for a stranger. Only an intimate partner would do such a thing and even then, it would seem abnormal. It was simply gross to sample a strangers half eaten meal.

Without warning, she stuck that middle finger in his mouth.

"Suck it clean."

Although it was certainly an act most would consider an indignity, he felt trapped by his own declaration not to resist what may come his way.

He sucked her finger clean as delicately as he could while also worrying what she might have touched with her hands before she came into the kitchen.

She pulled out her finger and smeared it with syrup once again.

"One more time." Since she offered no instructions, Ambrose assumed she was just trying to double his humiliation.

Without even thinking, Ambrose paid attention to the contours, texture and shape of the finger. He was even mindful of her polished finger nail.

"Well. That was better." She walked over the sink, washed her hand and wiped it with a napkin. "But we have a lot of work to do. Finish up so we can get started."

When he was done, Pippi began leading him up to the parlor where he had been shaved and dressed in lingerie the previous night. They were accompanied only by the sounds of their own footsteps.

"Is there any other staff here? Where is everybody?" He asked.

"Oh, they're around doing whatever it is they're supposed to be doing. I imagine they have instructions to stay out of our sight when feasible."

Despite her coordinated appearance and her manner of speech, Pippi's general mannerisms seemed less theatrical than most everyone else associated with Cassilda. It made her seem genuinely more down to earth and relatable than the rest, with the possible exception of Stephen the driver. Although Stephen did taunt Ambrose the last time they met. In all honesty, he realized, he would have been much worse if their positions were reversed.

"I feel like we snuck into a museum after hours." He tried to sound conversational.

"The old place certainly has that 'gothic' vibe. I can't decide if it's more Munsters, or Addams Family."

"I'm vaguely aware of those, but I've never really seen them. And yesterday I was a little too distracted to think about old TV shows, but you're right, it definitely feels theatrical. But I'm getting more of a Resident Evil video game vibe."

Pippi didn't seem to mind that he had a different take, but he still became somewhat self-conscious about not totally validating her impression.

"It's certainly theatrical," she continued, "but you have to keep in mind, everything here is real and not a prop. When you watch a haunted house movie, you're at least aware that it's not really haunted.

"Ooh!" she added excitedly, "The Overlook Hotel from that film, The Shining. Most people don't notice that the architecture in that movie makes no sense, but they still get a sense that something's off."

"I actually saw that movie and know what you're talking about because I saw a documentary about it."

Sensing that the time was right to pump her for some information, Ambrose paused her by placing a light hand at the crook of her elbow down the hall from the parlor.

Pippi looked down at his hand then up at him.

Ambrose immediately withdrew his hand with some worry.

"Until I or Governess Bishop say otherwise, you're not allowed to initiate physical contact with anyone. Not even a simple touch. You should also avoid accidental contact like an incidental brush, but in those instances, we'll consider the context. For example: you can't very well avoid contact if two of you are in a confining space. I'm going to assume you haven't been instructed in this until now and not let it go any further than here." Then more relaxed, "You have a question I suppose?"

His initial reaction was to ask how it was fair that he could be touched, prodded and much worse by everyone else and yet he couldn't even engage in a simple everyday gesture. But he quickly realized that fairness was not at play where he was concerned. Regaining his composure, he asked his question.

"What is all this?" he gestured around.

"What do you mean?"

"Is this---" he seemed worried over the possible answer "--- is this satanic? Is this--- is Cassilda some kind of satanic witch?"

Pippi gently grabbed his arm and resumed their walk as if his infraction had already been forgotten.

"The short, and, I think, satisfactory answer for you, is no. Cassilda is definitely not a Satanist or a witch. The unsatisfactory answer is, I don't know what this is. It defies all logic but for me it pays well. I had already seen some really crazy shit in my life long before I met Cassilda.

"Don't misunderstand me. I had never experienced anything supernatural as with Cassilda" she clarified "but crazy just the same, and I've learned not to question things that pay well but might still unnerve me. Cassilda as you know, is very generous. I could have retired three years ago, but then what would I do with myself. But that's neither here nor there. I suspect that that if I dived too deep into Cassilda's world it might drive me insane.

"I should also let you know," her tone became a little less light, "that as a matter of actual fact, witches are not Satanist. In fact--- and you really need to listen to me on this, I wouldn't talk about witches, witchcraft and Satan around the Governesses."

"Why not. Are they--- witches?"

"Fuck no. Are you fucking crazy?" Perhaps it was her physical bearing coupled with her outfit, but he found It jarring to hear the word fuck coming out of her mouth. It seemed too anachronistically modern.

"I don't know about any of that stuff." He said defensively. "So I guess they must really hate witches then."

"Ehhhhhhhh---- that's not it either." She said more relaxed though she seemed reluctant to expand.

Then Ambrose remembered a small incident from the day before.

"Yesterday, I heard Governess Corey call Governess Bishop 'Goody Bishop'. She didn't get it all out because Governess Bishop shot her a vicious look. I suppose it could be her first name, but it didn't seem like it. But anyway, it seems strange to me. I've never heard 'goody' used as a name or a title."

Even though none of the Governesses were present, Ambrose was fearful enough of their authority to include the title "governess", rather than just saying their names.

"You'll learn all about the Governesses at some point maybe. Until then, take my advice and stay away from the subject of witchcraft. Honestly, and this is probably hard for you to believe, they don't really want to hurt you, but they have--- I suppose--- 'anger issues' is the closest way I can explain their attitudes."

They had arrived at the parlor and entered.

"Have a seat." she gestured at the divan after which she wheeled a display cart over and sat beside him.

There was a green silk sheet the size of a large bath towel covering the items on the surface. Ambrose felt some slight apprehension over the odd assortment of indistinct shapes that lay beneath.

"OK. Remember what you said in the kitchen. You want things to go as easy as possible."

"Yes."

"Don't tell me yes. Tell me you don't want to be savagely beaten for your wallet. Tell me you want to hand it over willingly."

He had a nervous little chuckle in spite of himself, but he repeated her words.

Pippi lifted the silk sheet to reveal a variety of moderately sized dildoes and some other items that escaped his attention. The small sense of mirth he had been feeling was displaced by a little turmoil.

Ignoring his discomfort, she grabbed the smallest one, which he guessed may have been five to six inches, had a slight curve to it and appeared to be made of ivory. For some reason, through his concerned mental state he couldn't help but ask---

"Isn't Ivory outlawed?"

Pippi was taken aback by the question. "You're a surprising guy Ambrose. I asked that same question when I first saw it. As long as the ivory is from before the ban, it's legal to own, sell and purchase. This piece is at least a century old. To be honest, however, I don't think Cassilda is as constrained by such laws as us normal folks."

Pippi became more upbeat. "The fact that you even had the presence of mind to notice that and draw the connection, tells me that you're on the right track in that your resistance is so low, that you can think to ask about ivory laws. It may turn out that I'll be proud of having you as a pupil. And on that note, we should get started. Just remember, this is ultimately for Cassilda's pleasure."

Although Ambrose caught on that Pippi was cynically employing positive reinforcement, it hardly mattered since it stood in stark contrast to his treatment at the hands of Governess Bishop just last night. Perhaps that was by design.

As to the purpose of her training, the implication planted in his mind was that occasionally Cassilda enjoyed taking on the role of "the man" during sex and it was for this reason that he was being feminized. It was all for Cassilda's benefit.

"Wow." He thought to himself. He was being feminized. But it was fine because it was only for Cassilda after all.

"Now. Open your mouth and no matter what, don't close it. I just want to see how far you can take this in before you gag."

He was perfectly fine complying as readily as if she were a nurse sticking a tongue depressor in his mouth.

When he gagged, she placed her thumb on the dildo right where it rested on his lip, withdrew it and spotted where her thumb lay. Ambrose' eyes were drawn to the spot. He noticed there were etched ridges along the dildo's length at regular intervals.

She wiped the dildo with a paper towel from a stack and placed it back on the table. She then picked up a pen and pad located there and made a note as to how far he was able to take it in.

"Well, Ambrose, first, let me thank you for not putting up a fuss. I'm being real here. But, I must say, that was a little disappointing. You can do better. I have faith in you." She squeezed his hand softly for encouragement.

He didn't want to admit it to himself, although Pippi took the edge off her comment by expressing her faith in his abilities, he still felt disconcerted at having disappointed her.

"Do you think if we try it again, right now, that you can do better--- for me?"

Perhaps it was that she was making his ordeal more about meeting her expectations rather than humiliating him, whatever the case he did want to do better.

"Can you do better for me?" She repeated.

"I think so."

"Great." She said enthusiastically. "I'm going to try something a little different. I'm going to tell you exactly what I'm going to do. I know that doesn't sound like much of a technique, but it works better.

"So, obviously, we're going to go in a little deeper, but I'm not going to pull it out completely when you gag, I'm going to withdraw it just back to the point before you gagged. Then I'll let you recover for a moment or two, and then slowly try to proceed. Don't worry about drooling or getting any saliva on your robe.