He is Your Master Now Pt. 09

After suffering an almost unfathomable humiliation that left him devastated and confused, as well as receiving tough love from Pippi, Ambrose steels himself to ensure such an incident never again happens. The days seem to pass by quickly and as his training nears its end, Ambrose experiences two pleasant surprises as well as coming to a thorny conclusion about Manuel.

He is Your Master Now Part 9: The Mystique of Femininity.

To date, the incident with the five men was the most traumatic experience of his life up to the point where the fifth man, Mr. Benson Auto Repair on Duke Road off 9D, seared his ass with a single, open-handed slap. That spank itself pushed his trauma to the point where he was left devastatingly unsettled.

The strength that man had to possess to deliver such pain in a single blow, contrasted with the multiple spanks he had to give Andrea to achieve the same result, and with a paddle at that. It made him feel completely insignificant.

At lunch, Pippi had to keep prodding him to eat. He was aware of her just enough to absentmindedly chew and swallow meal without tasting whatever it was that he was served. He was feeling too many emotions, and on a scale from one to ten, each one was at eleven. Very near to the top of that list was his utter helplessness when it came to serving Cassilda.

Had he not experienced it himself, he would have never guessed that it was possible for someone to be bound--- no, enslaved to someone by their own desire for that person, to the point where they would endure this feverishly mad existence.

Sex truly was a drug; he was an abuser of that drug. That was the only way he could explain what was happening to him: He was a drug addict and drug abuse lead one down corridors one would have never imagined traversing.

Drug addicts who had previously lived mundane lives would do all sorts of things for a hit of whatever chemical compound enslaved them. Sell valued possessions, steal valued possessions and money from trusting loved ones, sell their bodies for sex to anyone who would pay regardless of their orientation, go homeless and give five dollar blowjobs in crack houses, or allow themselves to be passed around by gang members and frat boys alike, simply as a goof.

But when viewed from that perspective, living in a mansion with all his needs provided for while engaging in sex on a cosmically pleasurable level, was as far from hellishness as one could get when chasing a high.

He was told that Cassilda only wanted to occasionally fuck him as man fucks a woman. But as he reflected on his predicament, it seemed his humiliation was to be an integral factor in Cassilda's plans. He should have realized that earlier but even if he had, he'd still willingly submit to even her smallest whims.

But If it was the case that his humiliation was to take a more central role in his relationship with Cassilda, it seemed to him that it would make more sense to let him retain his masculinity, such as it was, because a small but powerful woman dominating him would magnify the power imbalance. It didn't occur to Ambrose that being so strongly opposed to his feminization, but putting up with the ordeal anyway, actually contradicted this rationale.

In any event, he was beginning to suspect that Cassilda was going through too much trouble to feminize him and that could only mean that once the process was complete, he would never again fuck her in his capacity as a man. And yet he still wanted her more than he had ever wanted anyone.

But even if he'd never penetrate her again, there was still the fact that she had let him fuck some of her female followers; that custom might still hold, and then there was Andrea. His climaxes had been nearly as powerful with those other women and with Andrea, as those with Cassilda. Clearly, that was a product of Cassilda's influence.

Ultimately, he came around to the idea that he could accept being Cassilda's bitch plaything if he could still get to fuck the others.

But what if she snatched even that away from him? Would he cling to the slimmest of hopes that she could change her mind at any moment and allow him to penetrate her? Would he find himself still living and hoping for a change of heart on her part decades later when he was an old man? Was she that powerful? Was his need for her that powerful? He suspected that he would indeed live out the rest of his life in sexual limbo.

Then there was the spank that rattled him to the core.

Despite everything he knew about himself, his body betrayed him when he felt the sting of a strong man, who was cruelly indifferent to his feelings, spank his ass.

For much of his life Ambrose had been called an asshole or a scumbag. He knew he was not a nice guy. Perhaps on some level, he knew he deserved to be spanked. And perhaps he had such a strong reaction because perhaps the act was meant to deliver a much-needed penitence that would set him on a better path. And perhaps because he had grown accustomed to seeing Andrea and a few of the others, enjoying corporal punishment, perhaps his body just didn't know how to process what happened and merely followed suit.

Perhaps, perhaps, perhaps, perhaps, perhaps. And endless series of 'perhaps' offering no real answers.

But this rationale evaporated when he remembered the sensuous sensation of the spanker's hot, moist breath on his ear. That was what had pushed him over the hump. A masculine voice delivering an offer, a promise, that was his for the taking.

Benson Auto Repair on Duke Road off 9D.

The man had placed the ball, as they say, in Ambrose' court and sitting there, barely cognizant of eating a meal that had grown cold, he couldn't be sure that he wouldn't play along.

He suddenly started to cry, just like a "little punk-ass bitch" he thought.

Pippi was unmoved. "Hey, you had to learn. Better now, rather than two or three weeks later, when you'd be expected to know better. The punishment would then be much worse. Believe me."

She mistook his tears for trauma, rather than the uncertainty he suddenly felt about his sexuality.

She went on to explain what she meant about a worse punishment. "One time, Cassilda got twenty men to watch her fuck one of her guys doggy style while all the men spit on him. It went on for so long, that she had to re-lube the guys asshole. And when the men started having difficulty working up enough spit, she had those who could, piss on that little punk ass bitch. You think you feel awful now? If she did that shit to you, it would have broken your brain. You'd probably go the rest of your life with Cassilda in a blank state unaware of what was being done to you. That bitch was strong enough to come through it on the other side. You're not that strong. So consider yourself lucky."

Of course that did nothing to make Ambrose feel better. He cried some more.

"OK, I'll tell you what, we're going to call it a day, so you can compose yourself. Understand that I don't have to do this," she pointed an angry finger near his face, "I'm doing it out of the goodness of my heart."

"Goodness of your heart?" he said through wracking sobs.

"Hey, you know what Ambrose?" she got really angry. "You need to grow the fuck up. We're not playing games here. I get paid for results and all I need is one single failure for Cassilda to get rid of me and hire someone else. So if there's even a tiny chance that you can jeopardize that, I'm going to slap you down as hard as I have to."

She took a deep, calming breath.

"Look, I can be nice to you. Admittedly, sometimes it's going to be manipulative, and sometimes it'll be genuine with some corrective stings added. But sometimes, Ambrose, it'll actually be real affection. What I'm saying is, this will all go a lot better for you if you find a way to get on my good side and work your way up to my genuine affection. Now stop being a little punk-ass bitch."

There goes that phrase again: Little punk-ass bitch.

He stopped crying long enough to ask, "You used 'little punk-ass bitch' as an example of an ana-chronism" he stumbled over the word, "and the man who--- hit me said that same thing. Did you set up even that tiny little detail? Or did you make it up on the fly."

"I set it up."

"But how is that possible? You couldn't possibly know that you'd have to punish me today."

"I was going to be using that phrase a lot for when I'd have to use it. It was only good fortune that today was the day."

"So that man was a gladiator, and I was the 'weak opponent that can't even compare'; a practice slave."

"I was teaching you a lesson and I needed it to sting as much as that slap on your ass."

"So he was told to hurt me too?" Ambrose started sobbing again.

"No. That he did on his own. Which is why we paid him less. It was a nice touch though," she said indifferently.

"Listen," she said softening her attitude, "if you're mindful in everything you do during your training, and you don't fuck up again, this will have been the worst thing that could have happened to you. That would mean that the worst is over if--- you behave and give yourself over to the training. Now, go to your room until dinner, then it'll be bedtime after that. I'll see you tomorrow."

She stood up, but before leaving, she delicately lifted Ambrose head by the chin and planted a kiss on his forehead. It was a parent's kiss meant to reassure a punished child that they were still loved.

"I know you don't believe it right now, but I really do like you, Ambrose. One day soon, you'll see that I do."

And with that she was gone after sending him to his room just like a child but with the exception that at least he'd get to have supper.

When he got to his small room, he saw that the wall over the dresser was dominated by a big screen TV. There was an accompanying cable box and remote on the dresser. At least he wouldn't be bored. When he turned it on, he saw that he could only get premium and pay per view programs. They wanted him to be entertained, but isolated from the outside world. He would later discover that he couldn't even get news on current events on news shows on those very same channels. How they did that, he couldn't fathom. But that was fine by him. At least he wouldn't lose his mind thinking about the man from Benson Auto Repair, Duke Road off 9D.

Ambrose began the next morning as a new man determined never to suffer anything close to what happened the day before.

The first few days after the spank were difficult as Gabrielle intensified his dancing lessons, while Pippi did the same with his workouts. Pippi herself was in much better shape than he had thought. His meals got higher in calories and fat content. After about a week, it all became easier and if he squinted at a mirror, he could already see small changes in his body.

So soon he marveled, though not happily.

Almost every night for the entire month, a different woman came to his room to pleasure him. Sometimes they were passionate but mostly they proceeded in a perfunctory manner. That wasn't the case for all the women who insisted they cuddle together, with him in the submissive role so they could caress his every curve. Those women always made love to him as a woman. Instead of being allowed to fuck these women, they licked his pecker as they would a clitoris, never once putting it in their mouths or even acknowledged his testicles.

Sometimes, he'd get to punish them, and he obliged only too happily, working out the aggression on them, that he couldn't on Pippi and Governess Bishop. But he enjoyed punishing them so much so that he had to be introduced to the concept of safety words. There was no safety word he could have used with Mr. Benson Auto Repair, Duke Road off 9D. But in that incident, he doubted that a safety word could have saved him.

His ejaculations continued to be intensely pleasurable.

Back in week two, he was given a bunch of books to read and a notebook. He was warned that he'd be tested on their content. They were all celebrations of the female or about female empowerment.

He began to understand that there was a strength to women that he hadn't perceived before. In a short time he wondered how he could be so clueless not just about women, but of lots of things.

He hardly saw Cassilda anymore but when he did, all she did was use magic dildoes on him. He was disturbed to find that even while staring at the Yellow Sign on her actual chest, he couldn't picture it the moment he closed his eyes, not even as an optical afterimage. He wanted to ask her about that, but he feared it was an out of bounds topic.

The first time he gave her a blowjob through one of those magic cocks, he stopped part way through, horrified when the rough plastic-like surface began transforming into something strange while he had it in his mouth. It was almost skin-like but not quite and even though his mouth was its normal warmth, the phallus actually dropped to room temperature.

The only rationale that he could come up with to explain this strangeness, is that those dildoes were real penises harvested from cadavers, refashioned for the purpose and somehow reanimated by contact with Cassilda's cunt. At least he hoped they were from cadavers, although "hope" was a strange word to use in this context. The other possibility is that they were sliced off men while they were still alive. Perhaps from former lovers. For the first time in his life, Ambrose was thankful for his small size; his cock wouldn't make much of a sex toy. But then again, it would make a decent oversized pacifier for someone during erotic baby play; something he had only recently become aware of.

Cassilda was able to calm his mind so he could continue and concentrate on his fellatio technique.

He had almost forgotten the effect that Cassilda's juices had on him when he smelled them and especially when he tasted them. When she came and flooded his mouth via the dildo's urethral opening, he had almost as strong an orgasm as he would have had she allowed him to fuck her.

During the one time they actually had a conversation, Cassilda told him that he was falsely ignorant. That his generally unpleasant disposition had filled him with contempt for things in general, and for women in particular, before he could even begin to think rationally about them and fold them into his world view. If he would just stop and think before even formulating an opinion, he'd become as smart as she knew he could be.

The fact that she believed him to be smart, at least potentially, had a great effect on him.

His relationship with Pippi had greatly improved. He finally saw that she really did like him and even Governess Bishop seemed to have warmed up to him.

The basic portions of his day hardly ever changed, for instance, after the purple robe was completely dispensed with, he spent much of the day naked, the only exceptions being when clothing was called for, such as dancing and exercising.

At the beginning of the third week, Gabrielle began teaching him how to dance with a partner. Since it began with ballet moves, there were some moves she couldn't pull off because he'd have to be lifted by a partner. The rationale she gave for this type of training was that despite her size, Cassilda would be able to pull off that feat of strength. He believed this of course.

Gabrielle, going as far as she could without even attempting to lift him, moved on to continue his ballroom dancing lessons as well as other styles; each necessitating a wardrobe change that always featured an expensive dress of some kind, all tailored to fit him, even as his body changed. There seemed to an endless abundance of them since he never wore the same one twice.

On the Friday of that same week Ambrose, totally nude of course, entered the gym with Gabrielle, only to find that Manuel was waiting for them. He was wearing men's dance leotards that roughly matched his skin tone, giving the illusion, somewhat, of him being nude himself.

Feelings of inadequacy and fear began to well up in Ambrose once more. He was especially aware that his body was more feminine since the last and only time he had seen Manuel. But by this time Ambrose had learned to exercise control over his fears. He did not want another experience as the one with the five men. Especially the man from Benson Auto Repair, Duke road off 9D.

From the scant times Ambrose had seen snippets of ballet featuring men, he always figured that they wore something under their tights that made their genitals appear larger, though what that could be, he didn't know. Whatever it was, it appeared as if Manuel was wearing at least two of them.

"Ambrose, Ambrose, Ambrose," the big man could hardly contain his good humor. "I've been thinking about nothing but today since Gabriella asked me if I could help her out. You know, I had to cut her off before she could finish telling me what was involved because I just needed to know if I was going to see you again. When she said yes, that was all I needed to hear."

He crossed over to Ambrose and gave him a lifting bear hug.

He was more solidly built than Ambrose had figured; the complete ease with which Manuel lifted him was unsettling. He had no doubt the big man could actually throw him some distance. But what concerned Ambrose the most, was that he was still naked, and at the height in which Manuel lifted him, his small penis came into contact with the massive bulge at Manuel's crotch.

By this time also, Ambrose had mastered trying to imagine the Yellow Sign while being more aware of his surroundings. And yet, he felt some stirring in his loins. It was very weak, but it was there.

With the man from Benson Auto Repair, Duke Road off 9D, Ambrose figured that perhaps he was responding to his rough treatment.

Manuel was not rough, however, he seemed to genuinely like Ambrose and he was clean with a freshly showered smell. So why was he feeling the faint beginnings of an erection? Maybe it was his own powerlessness that he was responding to. Apparently, being powerless turned him on. It made sense precisely because he was helplessly attracted to Cassilda and she held all the power in that relationship, and so he had grown accustomed to their being an imbalance of power. It was obvious.

Powerlessness.

That had to be it.

It just had to be.

Sensing his discomfort, Manuel set him down, but he still had a grin that Ambrose couldn't tell was either sly or genuinely beaming.

"I'm sorry Ambrose," he sucked his breath in "but I'm just happy to see you and you look so amazing."

Ambrose just nodded in reply.

"Ambrose, Manuel just gave you a compliment," said Gabriella, "it's proper to thank him and return it."

Ambrose panicked at the thought of being punished over this tiny infraction. If he learned nothing else, it was that he should err on the side of caution.

"Of course. I was just surprised--- happily surprised," he wasn't, really.

He did his best to smile at Manuel. "Thank you--- for the kind words." It was difficult to get his next statement out. "And you look very handsome yourself I must say."

Damn it. He meant to say, "I might say" not "I must say." He was so keyed up that even that small difference in meaning was over magnified.

"Aww Ambrose, still with the fake smile," he looked at Gabrielle. "But that's fine."

Then turning back to Ambrose. "I want a real smile, not a forced one and I can wait as long as it takes. Because there's nothing like a genuine, sweet smile from a sexy little thing like you."

Ambrose small cock seemed determined to betray him. When Manuel noticed his semi-hard on, he stopped laughing. In fact, he put on a relaxed expression and turned to Gabrielle.

"Gabrielle, I'm sure you guys are on a tight schedule so maybe Ambrose should get dressed now so we can begin his lessons."