He is Your Master Now Pt. 10

The last six months with Cassilda come culminate in a true, life changing event as Ambrose is herded to a flashpoint in his life after which, he can no longer smother his true self. But questions and mysteries still remain that must be resolved.
He is Your Master Now Part 10: A Shock to the System.

With Pippi taking the lead, the walk to the parlor on this day was more circuitous than any route Ambrose had ever taken within Carcosa Manor. With each awkward step of the way, the butt plug lodged in his ass made its uncomfortable presence known, which of course, was the purpose of the long route to the parlor.

When Ambrose started learning to apply his own makeup, his attempts were somewhat clownish, he especially kept overdoing the blue eye shadow. Since that time he had learned that applying makeup on a professional level was more complex than he realized. The most important skill he had to acquire was the ability to layer his makeup with an eye for nuance and balance. Next, he did his fingernails anew and all that was left, were the garments Pippi had picked out and his hair.

"There are many small breasted and flat chested attractive women out there, and for Cassilda's purposes, it's OK that you're somewhat flat chested. But since this is going to be your first time out as a girl, you're going to be paranoid about every tiny little detail, which is why we need to do as much as possible to convince you that you're more than passable until you become accustomed to outings.

She presented him with a padded bra of modest dimensions to enhance the tiny breasts he had developed, as a result of his diet and exercise routine.

She explained, "If we go too big, you'll think your breast look too fake. The fact there are also women out there with big, fake looking boob jobs won't do much to ease your mind. That bra will give you realistic and natural dimensions. Always remember, when you're a hot piece of ass, which at least Manuel thinks you are, a little bit of titty goes a long way.

"Ordinarily, I'd have to teach my students how to tuck, that's hiding your cock and balls between your legs, but because of your size, these tight panties will do just fine."

The panties had a strange protuberance in the front.

"What's this thing here?"

"Oh that? You're going to wear capri pants that are pretty revealing. That thingamajig there simulates a camel toe. Most women are wary of showing camel toe, but in your case, it'll add peace of mind."

That made sense to him and actually did lessen his anxiety just a tiny bit.

She handed him a form fitting pull-over sweater that was just thick enough so that the bra wouldn't show through. It was of a style that left his smooth, tender midriff and lower arms bare.

Next came the snug aforementioned capri pants that indeed left little to the imagination. By the feel of them, he could instantly tell, before examining himself in the mirror, that they highlighted his ass. His most valuable physical attribute apparently.

Since it would take more than thirty days for his hair to grow past his shoulders, Governess Nurse proved to be competent at trimming and shaping it. She also instructed him on how to fix it in different styles based on its length at the moment.

He also learned how to properly choose and fit a wig. In his old life, Ambrose assumed that wearing a wig was as simple as putting on a hat. He now knew how to expertly pick out the right wig for the occasion and clothing, prepare his natural hair to accommodate it and how to avoid separation between the wig and his scalp. Of course only the finest wigs were at his disposal. He prepared his hair and picked out his wig but Pippi insisted on fitting it.

After he had applied his makeup, it was obvious that she didn't want him to look in the vanity mirror in anticipation of some big reveal, which was ridiculous as he had already seen himself in drag every day.

The look was finished with bangles, a beaded necklace, a gold ankle bracelet and earrings. For his feet, Pippi handed him, black platform shoes with enclosed toes that added two inches to his height.

Since he was not looking forward to going out while dressed, his mood was very grim as he approached the three-way mirror, through which he had not seen himself since his first night at the mansion.

When he dressed for Cassilda, the lingerie made it easy to dismiss his sexiness as artificial because lingerie was inherently sexual and did much of the work, and it also came off as kinky to boot. This was very different.

As soon as he saw himself in the three-way, he had an epiphany. He could sexualize any clothing just by wearing them, rather than the other way around. Had he been wearing filthy, ripped jeans, a stained flannel shirt and scuffed Doc Martens boots, he'd still be quite attractive.

He kept turning at odd angles to catch glimpses of his curvier body from different perspectives and caressing himself all up and down.

If Ambrose saw a woman who looked like this in a night club, he would definitely hit on her. But he'd probably have to compete with hunky jock types who would like nothing more than to jam their big cocks into his--- her mouth. What happened next occurred before he could catch himself.

His gaze lingered on his bigger and shapelier ass. "Woo! Now that was an ass worth fighting for," he exclaimed as he whirled girlishly to face Pippi. He was brimming with excitement.

Pippi happily nodded her head in approval. "That ass could cause a barroom brawl."

His euphoria didn't last long as he noticed that his nipples had hardened, and he had goose bumps all over his body. That was when it dawned at him that he was excited about seeing himself as a gorgeous girl. The type who was perfectly capable of finding a sugar daddy and milking him for all he was worth.

It took a few moments, but he managed to regain his composure, mostly.

"I--- I--- was ju--- Just relieved that--- you know? That I look convincing. BECAUSE!" he hastily added, "no one will look at me strange or in like--- disgust. Because they won't know--- they won't know I can pass.

He took a deep breath " I'm relieved that I can pass. I mean it seriously that that's why I'm um--- excited."

"Of course," said Pippi. "But we have to run. Manuel should be waiting for us by now."

"Manuel? Why us he here?" he asked worriedly.

"Well he's going to drive us of course. Why would you even ask that?"

The lasting image of himself as a fuckable woman had caused Ambrose to momentarily forget that Manuel was the chauffeur. When Pippi told him that he was waiting for them, his mind imagined that the big man was waiting for something other than driving them around.

Once outside, Manuel marveled at Ambrose with open mouth.

"Holy fuck and God dayammmmn Ambrose!" he shook his head in amazement. "I have to tell you--- but you probably know by now because I haven't been too subtle, that I have a thing for you. But damn, seeing how sexy you look in regular street clothes? I can picture myself parading you around Manhattan, going to plays, fancy restaurants, night clubs--- I'd be proud to be seen with such a sexy little thing. Other men would be salivat---"

"OK. That's enough out of you," said Pippi good humoredly. "Do you always lay it down that thick?"

"Only when I'm inspired," he sucked in his breath theatrically and breathily said, "and I'm definitely inspired."

"Thanks." Ambrose was part mortified and part encouraged that he'd be able to pass after seeing Manuel's reaction, which was an obviously genuine reaction.

But, up until that moment, he hadn't really been sure that Manuel had not been expertly trolling him all along in a mind fuck sort of way. There was now no mistaking his attraction. And with that, he realized that this strong, virile looking man was actually, genuinely gay, or at least bisexual.

He retroactively felt vulnerable over Manuel's past flirtations. It put his uncomfortable feelings from the dance lesson in a whole new light. Particularly when Manuel became considerate of his feelings when he noticed Ambrose' half hardon.

It would seem that despite his blatant flirtations, Manuel's protectiveness of him was sincere. That signaled romantic intent, which was more involved than lust. This realization made him recoil in in alarm as that would make it more difficult for the big man to take a hint when Ambrose would try to discourage him.

Once again, Ambrose tried to escape by trying to envision the Yellow Sign, but Pippi broke through his concentration.

"Since we'll be going out in the public; it won't do to use male pronouns with Ambrose because some asshole might cause trouble."

"Yeah well they better not pull that shit around me," Manuel turned to Ambrose. "If anybody messes with you, they better be prepared for a good old fashion beat down."

Ambrose turned away.

"As I was saying," Pippi continued, "while we're out, it's 'Ms. Sweet'. Now, for a first name, 'Ambrose' won't do, obviously, and 'Ambrosia' sounds a little too--- much. There's also the fact that I hate the whole thing of feminizing a crossdresser's male name too cliché. But we still have to choose a normal name for when you're out, so for now we'll use Amanda."

Perhaps it was his paranoia at work, but Ambrose zeroed in on the fact that in the spelling, "Amanda" began with the letters A-M-A-N, as in: A MAN. Perhaps this was another one of Pippi's subtle digs. But after realizing that "da" didn't seem to fit, he figured that she chose it because at least it began with the letters A and M, just like "Ambrose."

Manuel opened the door while addressing Ambrose as Ms. Amanda "...if you please" he gestured at the interior of the limousine with one hand and extended the other to help Ambrose in.

Ambrose was mindful of Manuel's prediction on the day they met, that Ambrose would one day smile at him, so he always made it a point to avoid smiling at Manuel. And now, after the realization he just had, plus the memory of his urge to smile at the end of the dance lesson, he made a show of not taking Manuel's hand and churlishly threw himself into the limo. He instantly regretted it when the ponderous butt plug angrily made its presence known.

Manuel laughed good naturedly. "You are a stubborn one Ms. Amanda. But that's OK. I'LL get you to smile one day. Your stubborn persistence is only going to make that smile that much sweeter."

"Ms. Pippi, if you will." Pippi grabbed his helping hand with smiles and sunshine.

"I always make it a point to appreciate a gentleman. Thank you Manuel."

In the limo, Ambrose expected some consternation from Pippi for not being more receptive to Manuel's advances, but she never brought it up. That didn't exactly ease his mind however, because punishment was sometimes preceded by calm.

Pippi addressed Manuel as they passed the gates of the estate. "I'm going to put up the partition so that Amanda and I can have a word in private for a while."

"Well, heck, Pippi, you don't have to clear that with me."

"It's the lady in me. Sometimes I can't help but be polite where others wouldn't, and you certainly deserve to be treated politely."

"Aw, that's very sweet Pippi, and I seriously hope that part of that private talk will be you playing me up to Ms. Amanda Sweet back there. That's a tough nut to crack and I can use all the help I can get."

Ambrose stared blankly at him through the rear-view mirror. It wasn't clear to Manuel if he was angry or not, so he just winked, causing Ambrose to turn away.

"I guess Some things weren't meant to be Manuel." And with that, Pippi raised the partition.

"I only wish he paid that much attention to me," said Pippi to Ambrose. "But I understand why you wouldn't want that. You being you and all," a subtle reference to his issues with minorities.

But at least Ambrose felt relieved that he wouldn't be compelled to actually like Manuel in that way.

"I chose this week for this outing because not only are we near the end of your training, there are no new movies and since it's early, there shouldn't be too big a crowd. But there will be a bit of a crowd, it's Friday after all and this is the only multiplex for quite some distance. Basically, I don't want you to feel overwhelmed. Also, we should be able to just go in.

"Since I've been doing this for a while, I'm aware of a few things you should consider. Of course, you're going to be incredibly nervous, maybe even a little scared in the beginning."

"Ya think?" Ambrose couldn't cut back on the sarcastic edge. Pippi ignored the remark anyway.

Pippi managed to convince him to see a chick flick romantic comedy because there was likely to be much less men in the audience and he wouldn't feel as self-conscious. The alternatives were dramas he probably wouldn't like, an action film and a sophomoric guy's comedy. He'd definitely feel nervous in the theaters for the last two. It didn't really matter to Ambrose because he was going to be nervous no matter what, but it was a good call.

"Since you don't know the area, I'll tell you that the movie theater is part of the mall we'll be shopping at; it'll be a seamless move to the mall. The theater is more to ease you into the whole experience. You need to keep in mind that even though you're still going to feel self-conscious, most people are going to just pass you by without even noticing.

"BUT--- and you knew there'd be a 'but,' I have to say that you and I are head turners, so we will be getting some attention, and unfortunately some of it might not be so nice because some guys can't take a hint. You need to be more mindful of that and of not letting it get to you, than of being mindful of getting found out."

"Do you really think no one will see through all this?" Ambrose gestured at himself.

"Hell no," she said excitedly. "Look, crossdressing is a fetish for a lot of men, but generally, they try to blend in. You've probably passed a few in your life without even noticing.

"But you look waaaaaaaay too sexy and that's going to work in a weird way. Your gorgeousness is no doubt going to get you noticed, but that gorgeousness is also going distract them. I mean, look at you. No one is going to think you're a man. Duh!" she said snarkily while returning his gesture at his face and body.

But was it really snark? "a man duh" also sounded like "Amanda" and in fact, the very last statement could be seen as both reassuring and belittling . She said, no one was "going to think you're a man" after all. And yet she still genuinely liked Ambrose. Perhaps this part of her was a quirk that was out of her conscious control. She might not have even realized that she was giving him a back-handed compliment.

The rest of the thirty-minute drive was spent by Pippi talking about the past month and trying to tease out many of the thoughts and emotions Ambrose had gone through during his training. He tried to be as honest as possible about the truly awful parts, mostly when he was brow beaten into submission, but what he didn't enjoy about the conversation was pretending that he was happy to have been "broken."

Pippi was right about the choice of movie. The theater was sparsely inhabited, and it was mostly populated by women. As for the movie itself, the chick flick romantic comedy, it was actually enjoyable. They discussed it afterwards as they made their way around the mall, even though Ambrose' nervousness was heightened. He was surprisingly animated about the happy ending where the spunky career gal ended up with the nice guy who was under her nose all along, if only she'd have noticed that he was a smart, sensitive hotty. There was a side story that involved her friend, another white woman, who hooked up with a black man, though their respective races were not touched on in the film at all. It seemed to Ambrose that the universe was sending him a message.

His timidity amped up, however, when he began to notice all the ogling directed at them. Some men tried to be discreet about it, others not so much.

There was a lot of "hey baby," too many in fact, there were some inquiries as to his relationship status and there was one rude man who wound up calling them skanks for ignoring him. For a moment there, Ambrose feared the man would actually get violent regardless of the fact that they were bathed in daylight from the malls glass ceiling and in public. A big and burly man, came to their rescue and intimidated him, but not enough to keep the asshole from hurling impotent threats at him.

Both Pippi and Ambrose thanked the man who helped them, but it soon became apparent that he was expecting the pleasure of their company or at least their phone numbers (he took a particularly keen interest in Ambrose), but he didn't exactly have the confidence to actually ask. It seemed that he expected them to be overly grateful and do all the work of seducing themselves on his behalf. When it was apparent that they weren't interested, he stormed off angrily. Ambrose was very surprised when he realized that there had been nothing altruistic about his coming to their aid after all. Pippi wasn't surprised one bit.

"Usually, there aren't this many annoying men in a place like this," said Pippi.

It seemed to Ambrose that they could only fully relax in women's clothing stores.

They spent a lot of money on Ambrose at a lingerie store with Ambrose enthusiastically picking outfits--- for use with Cassilda of course. After that, they hit several stores to find sexy regular clothes.

There was a salesman at one of the stores who exhibited gay mannerisms that bordered on the stereo typical. Although Ambrose felt that the salesman was truly gay, he got the impression that perhaps he was signaling in order to make female customers feel at ease. He had a very strong fashion sense as evidenced in the manner in which he complimented both Pippi and Ambrose on their stunning appearance. Since he seemed to not know that Ambrose was a man, the compliments went far in boosting his confidence. He also got the impression that most of his compliments were meant for him and that his flattering of Pippi, while genuine, was more diplomatic in nature. For the first time, Ambrose felt a confidence that was catty in nature.

After they were done Ambrose asked if it was OK if they spent some money on men's clothes.

"I mean, all I have is what I came to the mansion with and I haven't seen those since day one."

"Well Ambrose," said Pippi, "do you really want to go to a men's clothing store dressed looking like you do now. I mean, that'll 'blow your cover'."

"I can pretend to be shopping for a boyfriend."

"Who just happens to be your size? How are you going to explain trying on the clothes in fitting room."

"I don't need to do that; I know my size."

"That attitude is why so many men dress like slobs even when they try to dress nice. But that doesn't even matter, you have more of a reason to try out men's clothes than the ones we bought because your body is no longer the same as it was a month ago."

Ambrose was speechless. Even though he had been trying on women's clothes while shopping, that fact was lost in the novelty of the experience. At no point did it occur to him that most of his men's sizes were now out of date.

He dressed professionally for his last job, dressed nicely to go to out on mostly fruitless dates, and he dressed comfortable for just doing nothing. He had an entire life of clothing back at his apartment, and all of it was useless now. He was a different person in habits, lifestyle and now in body. He wondered how long before his mind would follow suit.

"No. You're right. I just wasn't thinking."

Pippi placed a comforting arm on his shoulders. "You'll have plenty of opportunities to buy men's clothing when you're more appropriately dressed. Maybe we can get a couple of baggy items, like sweatpants and sweatshirts; you can pretend you're buying for a boyfriend today and wear them when you come back for men's clothing."