He is Your Master Now Pt. 07

With Pippi's personality standing in contrast to that of Governess Bishop's, Ambrose resistance to his as yet unknown fate continues to wane. Once arrived in the gym he begins to realize that Cassilda's plans for him are much grander than he supposed. A surprising encounter with Andrea adds a new wrinkle to his experience.

He is Your Master Now Part 7: The Road to Metamorphosis.

The large workout room was filled with a strange mix of both modern and vintage equipment, the latter which appeared to date back to the 1920s, though he wasn't sure as he was not an expert on such matters. By the looks of their fabrication, they appeared to have been recently manufactured. But it was quite possible that the mansion's effects somehow prevented them from aging. He would later find out that was the case except when it came to objets d'art, furniture and the like, which somehow managed to age gracefully.

"You can be a little more relaxed while we're down here today because our work will require a lot of contact, and feedback," said Pippi. "But you should never assume that will be the case every day."

Ambrose decided to test that by asking a question.

"Sex with Cassilda is pretty rigorous. Since I first met her, I've been having a lot of sex. I think I'm in pretty decent shape now, so why do I have to work out?"

"Before I answer, I want to reassure you that although Cassilda wants to enjoy you as a man enjoys a woman, you'll still get to get to have sex with your roles reversed back to what's considered norm ---"

"You already told me that, but why do---"

"I'm answering your question Ambrose. I said you could be 'more' relaxed down here, not 'totally' relaxed. It's rude to interrupt." The light tone of her words and calm expression on her face signaled that she was being instructive rather critical.

"I'm sorry," said a chastened Ambrose.

Pippi continued. "Ultimately, when Cassilda puts you in the role of a woman, she'll want you to be a little soft and a little curvy. In order to satisfy that need we'll need to do some body sculpting." She paused, allowing a moment for Ambrose to speak. When he didn't, she asked if he had a problem with that aim.

Ambrose wanted to object in the strongest terms, but his resolve was evaporating quicker with each moment. He shook his head. "No, I don't have a problem with that." It was clear he did but Pippi decided not to push the matter.

"OK," Pippi clapped her hands and breathed excitedly. "I'll need to see what I'll be working with so, off with that robe."

Once again, the familiar fear of exposure pecked at him, but he dared not hesitate and untied the sash, letting the robe fall to the floor. Pippi quickly turned away from him, annoyed, which struck him as odd.

With the side of her face turned to him, she expanded on her instructions.

"I'll also be training you to show a little more grace and proper etiquette; try to be mindful of everything you do and let's try that again. Put the robe back on, tie it and when I turn to you, take it off, fold it neatly, hand it to me, and I'll put it away."

When, from the corner of her eye, she saw that he had donned the robe, she turned to face him. Ambrose followed her exact instructions, but he was also careful to always shield his inadequate penis with the robe. He tried very hard to make it look nonchalant and lacking all self-conscious as he walked toward her, slowly raising the robe, to always keep it the between his cock and her line of sight.

She paid no mind to this clumsy attempt to delay the inevitable, and turned to go pack the robe in a drawer in what looked like a large metal dresser.

When she turned back to Ambrose, she could see that he used a hand to cup his dinky dick. It was amusing, and it could've been annoying because by this time he should understand that when he was asked to disrobe in the mansion, he was not to shield any part of his body. What kept her from being annoyed, however, was what he was doing with his other arm; it was placed across his chest.

He was trying to hide his nipples! Just like a shy woman would.

This puzzled her, not only because men generally don't cover their "breasts", but also because Ambrose had already been fully naked around Cassilda an unknown number of times. The Governesses had also seen him naked, as well as Andrea and some of Cassilda's chosen followers, whom Cassilda referred to as her maenads. No matter. The fact that he did so now, right after she told him they would be working to give him a woman-like body--- well, that was highly significant.

While she did teach her male students demureness, for when the situation calls for it, those who arrived at that characteristic naturally, had done so only after seeing significant changes in their bodies. To date, Ambrose was the only one of her male pupils do so prior to this phase of the training. This was as a sign that deep down inside, unknown even to his conscious, he was already resigned to the feminization process, and whatever protests he may have along the way, no matter how strong, could be overcome with firm persistence, rather than extreme corrective measures.

"He's already a sissy bitch," she thought. She wouldn't have to force sissification on him, she could tease it out. It wouldn't be completely easy, and she'd still probably have to apply some harsh corrective measures along the way, but she was relieved to see that Ambrose was a natural.

There was always a danger in forcing sissification on a man and desiring Cassilda or fearing her wrath wasn't always enough to ensure their cooperation. Some of the men were capable of seriously hurting Pippi or even killing her. As a precaution, Cassilda, no matter where she was in the mansion, was always present in the mind of a student. The more prone to violence they were, the harder she'd stay their hand. The problem was that she had to reach deeper into the more aggressive ones and risk breaking them psychologically.

"When you're told to present yourself nude, it's because we want to see your body. Your entire body."

She became a little more serious. "I now have to repeat my instruction to you. It's rude for you to create a situation that calls for any of your superiors to correct you. Now, because of how I operate, I'm unlikely to punish you, unless it's part of the training, or you commit some trespass that can't be ignored. You'd do well to get used to following my orders without pause because it's also my job to help you avoid any unpleasantness in the future, because as you well know, others won't be so kind.

"Now put your arms by your side," she said firmly.

He was actually relieved to learn that Pippi was not generally prone to deliver punishment, but mindful that she could change at any moment. When he placed his arms by his side, she took a step back and looked him over. Ambrose steeled himself for the kind of mockery over his size, that he had long ago come to expect.

"Hmmm." She said in surprise. "You have really nice skin. It's pale, but it's the kind of pale that gives it a nice, soft, creamy quality.

The effect she had on him by not mentioning his small penis was relief beyond measure. Another effect was that for the first time in his life, he was aware of the quality of his skin. He had never even given it a single thought before, and he didn't like that Pippi found it soft and creamy looking.

"Turn around please."

Ambrose, grateful for any opportunity to hide his penis didn't see a downside to showing Pippi his ass. He happily did an about face.

"Holy smokes Ambrose. That ass! Oh my god! Give me a moment. I have to take it in."

When an uncomfortably long interval had passed, she gave him her assessment of his backside.

"There a word for an ass like that: 'delectable'. Are you even aware of what a fine ass you have?"

There were two ways he could interpret her compliments. She was either telling him that he had nice man buns, or that he had the kind of ass some women might envy, and that some men would like to squeeze. So long as the attention was off his penis, he accepted the idea that the latter was more probable.

He remembered an argument once, where the other man told him to "get your candy ass the fuck outta here." He was as heated as the other man, and spoiling for a fight, but the insult had bothered him more than it should have, so he let the matter drop and angrily walked away. Other than that, no one had ever mentioned his ass.

She walked closer and prodded at him with a finger several times and squeezed each cheek in turn.

"Perfect firmness. If I was a blindfolded man, I would swear you were a woman" She said admiringly.

He startled when she smacked each cheek lightly.

"The jiggle characteristics are very enticing; among the best I've seen."

She spanked him again, several times; pretending to verify her initial assessment, but really keeping him off balance. She returned to face him.

Ambrose suddenly had a semi hardon to contend with. Pippi ignored it and rubbed her hands together to warm them before reaching toward his pecs. Instinctively, Ambrose sunk his chest away from her touch and flexed his shoulders forward giving his chest a protective concave form.

Pippi sighed with exasperation. "You're going to have to suppress the urge to cover up. But if you just can't control it, we have a fix for that I'm sure you'd like to avoid. Would you like to know what it is?" she asked darkly.

"Yes please" he said nervously.

"We round up about six to eight random men, throw a lot of money at them, and then bring them here to hold you down while they run their hands over every inch of your body--- you'd be completely nude of course. They'd be big, strong men and this would go on until your shyness was no longer an issue."

Since Ambrose certainly didn't want that. He forced himself to relax.

She laid her hands flat on his nipples and smoothly roved around the area. Ambrose struggled to overcome the tickling sensation. Pippi then moved behind him and held him close as she began rubbing them lightly.

There was nothing tender or sensual to her ministrations. She was simply getting a professionally detached sense of them. But while on its own, her handling of his 'breasts' did nothing sexually for him, the vulnerability he felt courtesy of his nudity along with sensation of the rough material of her skirt and jacket pressed against his nudity, unexpectedly brought him to a full hard on.

"Your nipples are a tad large for a man; that's actually a good thing as far as Cassilda is concerned.

She pulled away. "You'll find some workout clothes and shoes in the middle top drawer of that box, put them on."

As he walked toward the box, Pippi issued a very loud wolf whistle.

"God damn Ambrose, that's some awesome, sexy, walk-bounce you have there."

He had no doubt she was being sincerely complimentary, but it was a barb just the same. By this time, however, her barbs were losing the worst of their sting, such was her positive personality.

He was dismayed upon opening the drawer and seeing its contents. But he took to heart Pippi's warning about having strange men feel him up, he would rather be whipped by Governess Bishop, and so his dismay was brief. He quickly chased it away by telling himself "fuck it."

Inside the drawer was a pair of very flowery, form fitting leggings, a matching sports bra/shirt combination that would leave his abs bare, some very girly looking sneakers and pink ankle socks.

When he put everything on, Pippi could hardly contain her glee. She went so far as to walk over to him and grab his hands. "Honey, you look hot. If you were at a gym right now, you'd have tons of guys hitting on you."

The joy apparent on her face made it feel as if she was trying to reassure him. As if he wanted to attract men. Basically, she came off as just a regular gal doing her best to encourage a less confident friend.

For the next three hours, Pippi walked him through a specific set of exercises most of which targeted his ass and pecs and told him he would have to perform these exercises daily and without deviation. She then showed him a workbook they would be following and making notations within to mark his progress. It was a thirty-day plan.

Thirty days!?

"We're almost done for the day, but I need to touch on some introductory dance moves that we'll be expanding on tomorrow. It's all part of the training."

Pippi flipped a switch at the light panel. At the far end of the gym, a dark corner lit up. There was a small dance studio located there, complete with a wall mounted ballet barre.

One of Ambrose' saving graces was that he happened to be a half-way decent dancer, though as a man, of course. But it was a sure bet that Pippi meant to teach him the kind of dance moves a stripper might employ, and he wasn't sure he could pull that off.

Strippers felt a transcendent joy in their snake like gyrations, as if they became aware of every inch of the muscles involved. That was the appearance at least.

Dressed as she was, Pippi couldn't really show him dance moves by example, she had to describe them, which also meant that she had to lay her hands all over his body, which she did.

Eventually, her touch, felt through the feminine workout garments that hugged his body, particularly his derriere, was more than he could bear.

"I don't mind if my male pupils get hard regardless of their size so don't be embarrassed."

They broke for lunch with Ambrose still wearing his workout clothes.

Of course, good ole Governess Goode was there producing another delicious meal. But the portion she served him was larger than normal. Much too large in fact.

"Something wrong?" asked Pippi.

"This is too much food."

"Your breakfasts and lunches are going to be larger for the foreseeable future. We have to account for the calories you'll be burning while training, but on top of that, we need to add some fat on you for me to work with if I'm going to sculp your body. "

Seeing that he was demoralize, she hastily added, "Trust me. I have an eye for these things, it's my job and I'm good at it. You'll look hot."

Looking hot meant looking feminine and that wasn't his concern in the least. He didn't want to have a womanly figure. Surely, she knew that. Even so, the sunny and enthusiastic way in which she reassured him served to take some of the sting out of what she said.

After lunch, there was a series of brief, introductory behavioral lessons. Pippi touched on etiquette, proper stature, how to walk with grace, how to sit, how to behave, changing the pitch of his voice etc... and then she was gone for the day.

He half hoped that Cassilda would summon him for sex that night, while also fearing the prospect because it could be a repeat of last night. But shortly after he went to his room, he heard a tentative knocking at his door. He was certain that Governess Bishop would have barged in without knocking, or at least knock before barging in whether he answered or not.

"Uh, come in," he called out.

He was not expecting Andrea and he certainly wasn't expecting her in black latex stockings, with matching greaves and bra. Her smaller cock was exposed as she wore no panties. The latex was very shiny and the way some it caught the light, in contrast to the dark parts, and how it shifted with her movements, fascinated him.

He looked up at her face. She had a serious set of smokey eyes; very attractive though just shy of looking ridiculous like a raccoon. Her lips were coated in jet black lipstick. Her expression could best be described as frenzied lust. She carried a large leather purse in one hand--- in the other hand, she held a black paddle.

Ambrose' world sunk to a new level of misery. It was only yesterday evening that Cassilda ordered her to give him a blow job, leading him to believe that at least he held a higher position than she. But here she was with a paddle, clearly to be used on him. Was there anyone in this crazy domicile that did not have authority over him?

"What are you doing here?" he said, trying but failing to hide his angry nervousness.

She pointed to herself and covered her mouth. Apparently, she was under orders not to speak. Through body language, she ordered him to take off his clothes.

He ultimately didn't know what he was going to do, but disrobing would give him some time to go through his options, although that did nothing to still his slight trembling. She next mime-ordered him to sit on the edge of the bed, although that required more body language because he was expecting to have to lay prone on his belly, or some other subservient position.

Andrea crouched down and began rummaging through her bag. She pulled out a dog collar, but before Ambrose could sink further into distress, she quickly put it on herself. Next, she produced a leash and attached it.

Ambrose breathed a sigh of relief upon realizing that the paddle was apparently not meant for him. He was also relieved that at least for now, he was apparently higher than her in the hierarchy. Cassilda obviously sent her to be paddled by him and perhaps more. The question was why?

Clearly, he was being manipulated towards greater submissiveness, why then was he expected to be dominant all of a sudden? Was it a calm before the storm type of thing? Give him a little prize before introducing some as yet unknown, true awfulness.

She pulled a ball gag out of the bag, put it in her mouth and cinched it tight. The image of her mouth held open, the extension of her jaw and her lips straining against the gag was unexpectedly and darkly alluring.

As she moved to lay on his lap, he sat further back from the edge to accommodate her. It was strange to feel her small penis resting on his lap, but since it was smaller than his, he wasn't sure he minded even though it was the first time he felt someone else's penis.

She handed him the handle of her leash. She did not hand him the paddle however, she placed it on the floor within her reach. Awkwardly, she reached behind her to touch his hand then she spanked her own butt lightly. Following her example, Ambrose spanked one cheek lightly.

Andrea abruptly stood up with desperate disappointment on her face. She clapped her hands lightly and shook her head no. She then clapped them much harder, turned and pointed at her ass before turning back to see if he understood. He did.

"I've never done this before. What if I hit you too hard?"

Andrea's answer was to angrily shrug, as if to say, "so what?"

Most of the porn Ambrose watched was rather typical of what young straight young males watched. He enjoyed some of the rough stuff on occasion, but the S&M stuff looked too weird and too involved for him to enjoy. From the little he knew, people who were seriously into S&M seemed to form fraternal groups and spoke of themselves as being part of a "community" separate from other sexual tastes. He couldn't imagine the same phenomenon occurring with something like blowjobs for instance; there was no "blowjob community." The level of complexity of the S&M community seemed akin to that of the customs of some foreign country.

He also struggled to understand why anyone would want to be intentionally harmed. Since he had never fully explored S&M porn, he could dismiss the activity as mere theatricality. But now he was expected to spank a woman who, to his way of thinking, apparently had little regard for her physical well-being.

Then there was the question of why she needed spanking and potentially, paddling. Had she done something to displease Cassilda or was this her reward for behaving. Before he could ruminate on the matter too long, Andrea laid across his lap again.

Ambrose spanked her harder. In response, Andrea bucked hard against him twice, but he got the impression that it wasn't from pain.