Chapter 6

The training had no real end, instead of going to the hotel and sitting in his office or checking in on the employees Calvin or more specifically Moriah put in a leave of absence for him, explaining the co-owner suddenly vanishing would look suspicious, so he was going on a much needed sabbatical, or so everyone was going to believe. The fact that he was told that while doing some stupid feminine exercises didn’t make it better. “I get what you are saying, but I don’t like it.” Cal said, while sitting on the floor in front of the couch in the living room. Today he was wearing some of his girlfriend's clothes, lacy thong panties that had the fabric stuck between his ass cheeks, a pair of black and pink bicycle shorts, a sports bra… that was stuffed, not that he needed one at all and a pink baby T-shirt that exposed just a hint of his belly that he was more than thankful wasn’t gripped by the cruel corset. “I’m also ready to take a break.”

“Baby, I know this a lot to handle, but you are one of the hardest working men… I know.” Moriah almost stumbled on the word men considering her once husband was wearing very feminine attire, she hadn’t even allowed him to leave the bedroom till he put on some makeup. “You were saying how much the heels hurt your feet, if you want that to go away, then you need to continue.”

He didn’t know how much her little exercise was really going to help, right now he was sitting with his feet pointed forward, stretched out and held under the couch to keep them in the position. Earlier she had him keep his back flat against a wall, step forward a little with his feet and do foot raises where he raised the balls of his feet. The entire thing was off putting, but every time he raised a concern or tried to talk his way out of the mess she either got stern, very loving and acting accepting or seemed to be hurt that he wasn’t willing to let her help him. “Yeah, five inch stilettos aren’t something most people walk around in.”

Clicking her tongue, Moriah put her hand on the man’s shoulder, giving it a light squeeze. “You aren’t just anyone, I know you want to look your feminine best and I promise this will help you do that. In fact, I have something to help you with your voice!”

Calvin was about to ask what it was, skeptical about sounding feminine, not that his voice was ever that deep, but Moriah had already left the room, coming back just as quickly.

“Here I printed this off for you, I want you to try changing your voice like we discussed and repeat this a hundred times.”

Taking the offered piece of paper it was a near thing that he didn’t outwardly groan. “You want me to read this a hundred times?”

Moriah had to head off to work, already being a bit late, she would love to stay at home and mess with the cheating bastard some more, but things had to get done. “I do, but I don’t want you to just say them, I want you to feel the words, taking them and feel them. So you are going to record yourself doing them, send the video off to me and we will go over it when I get home from work. Just because I have to go to the office doesn’t mean I’m going to abandon the man I love in his time of need.”

“Oh… I ahh appreciate it hon, but you don’t have to.” Calvin did his best to keep any sarcasm out of his voice.

“Think nothing of it love.” Moriah bent down and kissed the feminized man on the forehead. “Why don’t you try it once while I’m here.”

Looking at the piece of paper in his hand and then up to the woman he loved, Calvin nodded sadly. His body was smooth, having shaven his body with one of those pink razors just that morning before patting himself dry and applying skin cream. Right now he was working to help condition his feet to tolerate wearing heels longer and despite that he was pretty sure what he was about to read was worse. “I believe in manicures. I believe in overdressing. I believe in primping at leisure and wearing lipstick. I believe in pink. I believe that laughing is the best calorie burner. I believe in kissing, kissing a lot. I believe in being strong when everything else seems to be going wrong. I believe happy girls are the prettiest girls. I believe tomorrow is another day. I believe in miracles.” Saying that all left a sour taste in Calvin’s mouth.

“That isn’t a great start hon, you can do better. Try to soften your voice a bit more… I’m sure you will get it.” Moriah was already planning on adding more to the affirmation later, and if it was up to her Calvin, or Clara was going to repeat it enough that they were going to be dreaming about it.”

The manta was bad, going over it and having to watch videos on how to perfect a feminine voice didn’t make it better, but it was still a long way off from how horrible the day Moriah took him to the mall.

The worst day in Cal’s recent memory came when Moriah wanted to go to the local mall.It wasn’t just some innocent trip, no she wanted him to go out in public wearing women's clothing like he was some sort of willing crossdresser. “Moriah, please.” he begged when they were near the front door to the house.

“Clara, we are already going. You don’t have to beg me.” she said, relishing his anguish. Making her think back to one of the many times Bethany Long, the operations manager at her hotel had sat in her office with a crying young woman that felt violated because of her then husband. What happened between them had been consensual, but she didn’t think that would really hold up if things went to court considering the power dynamic between a maid and one of the owners of the hotel.

“That isn’t…” Calvin started.

“Stop trying to talk yourself out of this Clara, we are going and you are looking wonderful.” She had brushed his hair back, adding some hairspray to keep it flat instead of it poofed up like he often wore it. His face had been softened with the application of contouring and other makeup, while she had him dressed to look his feminine best. A multi colored plaid blouse that was white, black and a few shades of purple, the garment just hanging off his shoulders. It would have revealed the bra traps of the stuffed bra, but the black lightly pleated skirt hand suspenders built in, making the outfit just an extra little bit cuter in her opinion. She had him walking around in the heels she had bought from the escort he had paid, but for today she let her doll borrow a pair of her own heels that she had only worn once for a dinner party. Four inch stiletto heel black pointed toe pumps with red accents and then topped everything off with a small tanned leather purse. “Wait, are you afraid you haven't perfected your walk yet?” Moriah said with mock sympathy. “Aww, I promise you have a perfect little wiggle, but if you want to practice some more I can get the quarter.”

The learning to walk in heels that felt like stilts had not been easy, when Moriah had been flustered with him enough she had wrapped one layer of toilet paper around his thighs before going over it again with duct tape to as she put it, help his feminine gait and then proceeded to do the same around his torso, taping his upper arms to his sides so that he kept his elbows in. Still he hadn’t been able to keep the quarter between his legs for long and that just prolonged the experience. “The mall sounds fine.” The experience hadn’t been pleasant, nor did he really enjoy taking a bath, though he could admit the hot water and bath bomb helped relieve the pain in his feet with the less than minor assistance of the Advil.

Walking out to Moriah’s car had been nerve racking, people he knew lived around there and even though he hadn’t seen anyone it didn’t mean others didn’t see him through their windows. The anxiety in him only grew on the drive out, at every red light he wanted to scrunch down and hide. Even if his Moriah had let him get away with that, the corset he wore didn’t physically allow for such activities. The entire thing was nerve racking and if his girlfriend didn’t think she was helping him live out some sick fantasy he would swear she was enjoying torturing him.

There were many stops at the mall, one of the first was a shoe store that catered to women. Where he ended up purchasing two pairs of heels. “These will be perfect for you for work, what do you think Clara?” Morah held up a box with black glossy rounded toe pumps with a three inch heel.

“Stilettos?” he said looking at the thin heel.

“I know, aren’t they just perfect!”

That was a topic he wanted to discuss. “Isn’t that a bit much for ahh…”

“Clara.” Moriah said with a warning tone. “Voice.” She gave her skirt wearing man a hard look, loving every second of the day so far. “Besides, we already talked about this. No need to hold back, you get to live out your fantasy and it helps our cause. Now let's look at buying you this pair and… this one.” she grabbed another shoe box with a black pair of stiletto three inch heels, these looking more like they were made of or covered in a felt like material. “Why don’t you sit down and try these on.”

‘I’m supposed to like this, heaven help me.’ Calvin thought trying to plaster a believable smile on his face as he took the two boxes from her. “Sure.”

The pointed toe pumps had to be exchanged for a pair half a size up, for a brief moment Calvin let hope take hold that they could call things done, but instead the woman he was once married to wanted him to take advantage of what she called an opportunity. “Now we got what you need for work, how about you pick out a few more for your personal time!?”

“But… Why, we have what we need. I mean we go those two and the ones at home.”

“I can tell are a bit overwhelmed.” Moriah took his hand in her own and patted the back of it. “Don’t worry, I’m here for you. For one, a girl like you can never have enough shoes, you know and I know it. If you hadn’t been afraid I wouldn’t accept you I’m sure you would have wanted to turn one of the guest bedrooms into a shoe closet.”

Picking up a single white heeled shoe that was five and half inches with a hidden inch and a half platform in one hand, she grabbed a similar one in black, but was a peep toe she held each out for her feminized man to see. “White goes with some outfits, black goes with others.” She then put each of the shoes in Calvin’s hands before grabbing a red strappy six in sandals. “Red goes with others, you understand? You have to mix and match for the right outfit and after today you will own more than just that costume you love so much.”

Putting the new shoe she had picked up into Calvin’s arms she put her hands on her hips when he didn’t respond. “Clara, you need to get your head out of the cloud and start paying attention, unless you want someone to find out your little secret.”

The lecture had only made skirt wearing man feel smaller and he did his best to shush her, only succeeding in getting her to stop when he promised to be a good girl like he had done during sex. The last thing he needed was her to let everyone know that he was actually a man wearing women's clothing.

When they left that particular store Calvin was now the not so proud owner of six different pairs of heels and as if it was a bonus his mind left him the impression his feet would be constantly sore. “Can we go home now?”

“Not yet, love.” she gave him a wink. “Best part of being a woman, something, having a little fun.” Moriah said to the beat of one of Shania Twain’s songs. “For now that fun is shopping and you need a wardrobe.”

From there they went from one department store to another, hitting small clothing stores in the mall like the upscale clothing store The Hanger. Calvin didn’t know how many places in the mall sold woman’s clothing, but he was mostly convinced they went to them all. Moriah hadn’t been happy with just picking out dresses, skirts and blouses for him, but insisting he participate. “Come on, you know you love the feel of this, a white linen dress on a hot day when you are out at the park is exactly what you need.”

“I’m not going to the park.” Calvin whispered. “This is just for work, I’m going to find out where the leak is and take care of it.”

“That's my girl, willing and determined, but you can’t work all the time. You will need a break and can’t stay inside all the time. Now do you like this dress? Should we find something a little shorter?”

“You know what, I think this one will be perfect.” Calvin said, wanting to nip that shit in the bud right now. The skirt he was wearing right now isn’t something he would consider too short if he saw a pretty little thing wearing it. The skirt wasn’t a micro mini or anything crazy, but it didn’t even touch his knees, making him feel exposed. No way was he going to get something shorter if she was letting him have a say in it. At this point he could tell his shopaholic girlfriend was in her element and what he said mattered little. A reason why he didn’t go shopping with her, the woman could spend all day and most of her account if she wasn’t careful. It was her money… well in this case his.

The count, that he believed was accurate, was they had picked up four skirts, six blouses, nine dresses, that would only be described as lingerie, more bras and panties than he knew what to do with and a large selection of pantyhose and stockings. “I don’t need all of this, we have spent way too much!” He complained thinking of the money, his money she was spending on this insanity. They were dropping off another load in the trunk of the car, one of the bags being nothing but assorted panties. He hated that he couldn’t even drive, sure he could kick off the heels and drive barefoot if he got the keys from Moriah, but there was the possibility of an officer pulling him over dressed the way he was.

“Girls need variety Clara and we don’t know how long you will be this way. Once you start working, I can’t go out shopping with you, it would not be appropriate for the owner to be seen with a junior maid now, would it? This is the second time I have had to tell you this.”

He hated this, he hated all of it and with every passing day things only seemed to get worse. Before the day before the shopping trip there seemed to be that extra little kicker to make him feel small. The blow that hit him this time was when Sidney called Moriah to let her know what he had been able to arrange.

Clara Diane Bent didn’t have a social security number and had no work experience and the best he could do was put her, he had actually used the feminine pronoun making Calvin vow to fire his ass the second this was over. He said that he could hardly justify hiring someone like that all and that the best he could do was have her hired as a junior maid. Going on to say that Clara should be happy he could arrange even that as an undocumented worker.

He let the undocumented joke slide, well almost slide, he had reached over to hang up the phone that was on speaker mode before telling Sidney to fuck off, but his hand got slapped away by the woman who sat next to him the couch.

“Oh my god, with her honey colored skin she could pass as being of Spanish descent. Clara you may need to work on getting your green card, I don’t know how I feel about sheltering an illegal worker at my hotel.”

Calvin knew she was joking, just messing with him, even if she tried to sound serious. “Our hotel Moriah and I don’t speak Spanish.” He was not enjoying the teasing and was about to try to hang up the phone once more when Moriah gave him a hard look.

That was when he heard the tisking sound from the phone, or more specifically from Sidney. “Only people I see… well hear are Clara the soon to be junior maid and one of the owners. Moriah Abrams is the only active owner here. Shouldn’t you be calling her Miss or Mrs. Abrams, don’t you think?”

That day Calvin had been wearing the maid outfit, it was bad enough that he was wearing the dress he had fucked a handful of girls in, but it got worse when Moriah had snapped a picture and shared it with the head of their security team. Calvin just imagined the taller, older man looking him over as if appraising how he looked. The dress wearing man wasn’t sure why in his imagination he also had a little head piece and pieces of fabric around his wrists, his stupid mind adding the extra touches that felt just a little bit more sensual thanks to his proclivities. Not a single demeaning word came from the phone about how he was dressed, but it more than pissed Cal off that Sidney was acting like he was just some maid.

Jumping to his feet Calvin almost immediately lost his balance. “Where the fuck do you get off on talking to me like that Sid? Talk to me like that again and you will find yourself in the unemploy…” The angry man didn’t get to finish his sentence, that was the first time, but not the last, that he experienced his ex-wife slap his rear end hard enough to cause him to yelp.

“Clara, Sidney is the head of security and you should be addressing both of us properly. Now apologize to both of us.”

Calvin hadn’t responded, just looked at her in shock before she slapped his ass again before she stood up, giving him a serious look.

His eyes growing wide, Calvin felt like the woman he had once been married to stood twelve feet tall, he wasn’t sure exactly when it had happened but the power dynamic in their relationship had shifted. “I’m sorry Mrs Abrams and I’m sorry Mr. Larson.” His voice sounded so meek to his ears, part of it was because he had been talking in nothing but a higher register, something Moriah had insisted on for the training over the past few days. Being hit like that had put him completely off.

“It is Miss Abrams, but you are forgiven Clara. Now why don’t you be a good girl and pose for a photo, or even better a video. You can pose for him and tell him thank you for getting you a job.” She then clicked the mute button on the phone before continuing. “I don’t know why you are acting like a child, some spoiled brat when I’m literally giving you the keys to your dreams, but I will not have you talk to Sidney like that. The last thing we need to have him quit! What would happen to the deal then? At this point if he wanted to quit I would suggest you going over his lap and let him spank you till your ass was red, but right now I’m not sure if you would consider the a reward or a punishment.” Pushing the mute button again she spoke to the man on the other end. “Just one second Sid.” She then muted it once more. “What will it be, Clara? Will you a good girl or naughty?!”

When Moriah saw the facial expression on Calvin, he looked broken. Normally a confident man, ready to take command as he moved around with a swagger she felt a rush of pleasure.

That night had ended with him posing and even doing a short video thanking the head of security for helping him… her get a job. It has been so bad and yet somehow today was worse.