Jordan in training

Placing his purse on the small desk Jordan glared at the thing, it was overly feminine and he hated it almost as much as he hated wearing the heels. At least the walk to the Bus and into the building was enough for him to figure out how to walk in the things without falling down. “Hurray for natural balance.” he mock cheered himself as he turned on the computer. He was mostly alone in the area; Tiffany wasn’t in yet nor was his boss a Mr. Adam Wesker so it was smooth sailing to get up to the fourteenth floor. He didn’t even have to deal with a bunch of guys hitting on him, maybe this getting in early thing was the way to go for as long as he was stuck here and he hoped that wouldn’t be long.

Opening up his email he saw one from a Mrs. Bridget Gunther from twenty minutes earlier. “Wow she gets in real early.” He said as he read through the email. It looked like yesterday the goal was just getting to know everyone, that is why they only had Jordan doing things like fetching coffee. Business hours for both today and tomorrow he would be getting some hands-on training to fit his secretary role. He didn’t care if they called it an admin assistant or a PA, he knew what the job was. What kind of training could they really give him, didn’t they see his certifications in IT and his work history? He read through the list, phone training, business and phone etiquette, printer training, learning to file, basic typing skills. Geeze this was going to be mind numbing, but the at least there was a good thing about all this. It looked like Mrs. Bridget had Tiffany train him. Apparently, Tiffany was promoted to front desk manager and worked on this floor so she knew the ropes. Mrs. Bridget was doing him a solid and she didn’t even know it. This was odd to him, the job title changes for Tiffany sure just sounded like a different way to say secretary, but she had to do it on the ground floor, not much of a promotion.

Jordan was just starting to read the next email, a welcome to the team email blast to the floor to welcome Jordan Applegate to the company when he heard his name in a tone that sounded surprised. “Jordan!” Janet stood before him dressed sharply in a nice knee length dress with a trim suit jacket, she was holding a few things. It looked like a purse, a laptop back and a plastic bag with boxes in it.

“Oh hey Janet.” Jordan said to his ex-girlfriend. He had completely forgot about talking to her about the current predicament, and now here he was dressed like a woman sitting at a desk.

“Don’t you oh hey Janet me...” Janet looked around before leaning in closer “Mister! What is going on here!? No scratch that, you're coming with me.” Jordan had just started to turn his office chair to the side before Janet grabbed his wrist and practically dragged him into the woman's bathroom.

Turning the lock on the door once inside she turned back to Jordan scowling. “Explain... Now.”

Jordan swallowed hard and told her what happened from the time they lost talked. “I, I just can’t believe you I mean... It obviously happened. But Jordan things going bad around you all the time and it is always other people's fault. Tell me now that you could not have avoided this.”

Jordan could feel Janet’s anger, it was pretty sure she wasn’t this angry when they broke up. “Yeah, I guess I could have avoided some of..” The sentence didn’t get to be finished when Janet snapped the fingers on her left hand and pointed at Jordan.

“You guess, well here is something you don’t have to guess about. You wanted to still be friends; well, you have fucked that up big time mister... Missy. Jordan, you don't seem to grasp what you have done here to you and to me.”

Jordan for his part bit his lip and looked down to the floor “Yeah I know I screwed up, why else would I be here looking like this. I know if it doesn’t go well, I could make you look bad.” He looked up to Janet with pleading eyes. “It is going to be okay though I will be able to get my clothes soon and with my computer, I can find another job. I will take anything; I screwed this opportunity up but maybe I can reapply later for a spot on the IT team once I pick up something that can get me out of these clothes.

Janet looked at her once lover and moved behind him moving his shoulders so he was facing the mirror. “You still don’t get it. Yes, you can leave here, and yes that will look bad on me, but that won't fix this.” She said pointing at the two women in the mirror. “You told HR you are a woman, Mrs. Gunther is a sweet southern lady that I have worked hard to get on the right side of and you lied to her. You made it so I lied to her. Do you know what will happen if others find out who you really are? Do you?”

Being in a bit of a panic now Jordan shook his head. “Thanks to you, we have both committed fraud. That means if you are found out, not only would you be fired. I would be fired and then the company could have us both arrested. You have made a big mess Jordan and I have **** but to help you along or we both get fucked.”

Picking up her bags from the floor Janet put them on the sink. “Okay here is what we need to do. You said you are going to be able to bail soon as you can get into your room and find a job at fast food or whatever. So your goal Jordan is to appear like any other office girl here, no standing out cause you want to move into IT. If someone so much as uses a big word you are to look confused, do that lip-biting thing you do. It will look real cute with how you look now. What you have done so far is impressive, but you need more to blend in. I remember you calling some of the office girls and secretaries bimbos before Jordan, congratulations you get to really join them now.”

Jordan’s jaw as quivering “Please no, I can get by without acting dumb.”

“The ship has sailed and you are going to play the role you chose. You are always getting other people to pull you out of your shit Jordan, I’m tired of it and will not go to jail for you. Now let's take a good look at you.” Janet carefully looked over the crossdressed man.

“When did you get this skinny Jordan?”

“Oh, that is a corset I borrowed.”

Janet without asking started to unbutton Jordan’s blouse “Let me see.”

“Hey, slow down.” Jordan’s voice almost cracking

“That looks good, but I’m going to tighten that.”

Jordan shook his head slightly hating what was happening. He felt the corset get tighter and push the breath out of him. “That should do it, for now. I expect it to be at least this tight tomorrow. It will not only help give you a womanlier shape, but it will also help you stand and sit straight like a proper girl should.”

“Now I love what you did with your hair, I’m glad you did more than wash it. A little curl is a good look with your black hair. But you will need more makeup, here let me help you.”

Janet reached into her bag and pulled out her cosmetics, applying eye shadow, mascara, and some red lipstick. “Mmm yeah, that looks good. I will give you what I just used on you so you can touch up through the day, but Jordan. Tonight, you need to sit down and learn to do this yourself, from now on I expect you to look your best. Online you can learn how to contour and make your nose look smaller, the lip plumper I gave you should help with making your lips look bigger and more inviting.”

“I don’t want bigger inviting lips.” Jordan meekly protested the changes. He could see the eye makeup made his blue eyes pop and that with his matching shirt made him look more appealing, let alone his puffy red lips.

“Sure, you do Jordan, every girl wants to find herself the right now. Now Jordan you do not know how to present yourself as a woman and right now it mostly looks like you are shy, but we are going to fix that so you don’t get caught. I am saving the page reddit.com/r/HighHeels on your phone, along with reddit.com/r/MakeupAddiction, cosmopolitain.com/style-beauty/beauty. I expect you to be looking at these whenever you have free time, you have a lot to learn girl and if someone else sees you on the sites it will only help your cover. Now don’t try me, girl, if I text you a question from one of those sites, I expect you to have the answer quickly because you have already read them. Lastly, I have set up an alarm on your phone for it to beep twice every twenty minutes. That is your cue to turn on the camera function of the phone and check your makeup and touch it up with what I used on you in here.” Janet said as she smiled wickedly.

“The men here already wouldn't leave me alone, even when I told them I have a boyfriend.”

Janet moved over to her plastic bag pulling out a box, “Oh a boyfriend, that is the perfect angle. Men often want what they can’t have. Now put these on.” Janet held out a pair of five-inch stiletto-heeled black glossy leather shoes. “What no... Those are way too high, I can’t walk in them!”

“Jordan, Jordan, Jordan. You won't be walking you will be mincing around the office in them sweetie, you are just lucky I picked them up from getting repaired on the way in this morning. Just remember one foot in front of the other and sway those hips girl. The more the men think of you as a piece of meat the less likely they will be to figure out who you are. And remember you will be playing the part of the air-headed bimbo, that way no one will trust you with anything important, and the less likely you will be missed when you get another job.”

Taking small steps Jordan was unsure of himself but all this was happening too fast and he didn’t see any other choice. If he told Janet no everything would fall apart, not just getting money for Eric, but possible jail time. “Ready or not let's get back to the office sweetie and Jordan. It might seem like I am pissed at you and being cruel, but you know I’m only helping right?” In the last part, Janet said in a softer voice, the statement wasn’t entirely true. She was enjoying seeing her former lover looking like an office girl now that she had some control over the situation, but she really did want to make sure he didn’t get caught. For both of their sakes, but if she could get a little payback along the way the better.

Mincing past Janet, Jordan was all kinds of embarrassed, and as mad as Janet was, he was lucky she was trying to help him. Even if she was also trying to save herself. After a few steps, he saw one of the teenagers from the mailroom check him out as he walked by and something occurred to him. “What if someone touches me or something, do I go to Mrs. Bridget about it?

“Of course not, you are in your first thirty days, the company can fire you for anything. This place is a boy's club, I have been here for over a year and I wouldn’t report sexual harassment unless I had to. Jordan this place is a boys club, I told you stories about how they go through administrative assistance so fast, why do you think that was? For you though, what do you think would happen if HR looked into the issue, looked into you too closely. I don’t have faith in them getting in trouble at all, but that just sounds like a ticket for you to get us both in trouble, and don’t you dare get us in trouble. Just don’t put yourself in that type of situation, and if one of the boys touches you, don’t raise a fuss."

Walking back to the small desk Janet was going to wish him a good day, but standing behind the desk were Tiffany and Mr. Wesker. They seemed to be talking about something but stopped when the girls approached. “Miss Harrows, always nice to see you. I understand Miss Applebottom here is a friend of yours, but please do make sure you don’t keep her away from her desk too long in the future. She is late for her shift.” Janet wanted to say something snide to Adam, but she was going to let it slide she really loved the new nickname he just gave Jordan on accident. “I will leave you to it Jordan, have a great day with Adam and Tiffany.”

Tiffany moved away from Adam as he was talking and gave Jordan a hug. “Umm sir I was actually already here and my name is..” Jordan was pointing to his purse, oh he hated that he thought of it just then as his purse. Though as he was going to correct him on his name Janet gave Jordan a look that said drop it, don’t make waves so he stopped.

“What was that dear? I like the shy ones, but you will have to speak up.” Adam said looking his new secretary up and down, she sure had cleaned up from yesterday. Not the bombshell she could be, but he was enjoying the eye candy that would be just outside his office.

“Nothing... Sir.” Jordan said meekly biting his lip and looking at the ground like Janet had suggested.

“Don’t worry Mr. Wesker, Jordan is in good hands we will get her all trained up and ready to meet your expectations.” Tiffany came in trying to save Jordan some embarrassment. It was clear to her that the mousy girl she met was trying her best to dress for the job.

“I will leave you to it, Tiff,” Adam said as he walked into his office closing the door.

Tiffany looked at Jordan as she saw her still looking at the ground. “It will all be okay Jordan, this will all work out. I know you were already here, and just because he didn’t mention how much more effort you are putting in to fit in today doesn’t mean he didn’t notice. I promise you Mr. Wesker appreciates the effort you are putting in for him.”

Tiffany was all smiles as she led Jordan to his seat. “For him?” Jordan questioned.

“Well of course also yourself I see that silly, but we have a role to play here and must look out best to represent the men that stand behind us. Now, let's start with learning the phone, shall we? The typing skills can wait till later, I have a little surprise for you as a welcome gift.” The pure glee in the bubbly girl's voice was easy to hear and sitting this close to her he could really take the time to appreciate how she looked, and how she smelled. He was happy being able to see her all day, but he hoped she didn’t hug him too much or he might have to go re-tuck himself.

“Oh... A surprise?” The last thing Jordan needed was more surprises, today had been full of way too many of them and it had only just started.

“Oh yes! I have us a nail appointment at noon today, and already cleared a long lunch with Mr. Wesker and it gets better!” Tiffany’s voice picked up an octave at the word better. “Mr. Wesker is even going to pay for both you and me. Isn’t that great Jordan!? We get to spend more time together and get pampered while your boss pays for it. You are so lucky to have a friend like me.”

Suddenly the idea of spending the day with Tiffany didn’t sound nearly as good.

A few hours later Tiffany had to go run downstairs to take care of something before they went to lunch and the nail salon. She left Jordan with the simple task of getting Mr. Wesker some afternoon coffee and said she would be right back. Before he got up Jordan’s phone beeped at him and with a sigh, he pulled out his lipstick and touched it up in the phone app. This thing going off every twenty minutes was a little excessive, he hated checking and touching up his mascara or lipstick in front of Tiffany. Well hated doing it all together, but in front of her just made it worse. Mincing in his newly acquired five-inch heels Jordan stepped into Adam Wesker’s office, it had a solid wood desk closer to the back of the room, two chairs to the left of the door, and a small couch to the right of the desk where the manager sat now looking over some paperwork. The door swung shut behind Jordan and he came up in front of his boss. “Mr. Wesker sir, I have the coffee you wanted.” Adam Wesker didn’t look up from his paperwork and said

“Just put it on the desk near the keyboard.” Looking at the desk Jordan could move one of the two chairs out of the way to do that, walk past his boss behind the desk or just lean over it. With the way his feet hurt he didn’t want to take one extra step, he didn’t have to, so he bent over leaning on the desk, and place the coffee down. Jordan both heard and felt his boss at that moment. “Well... You know Jordan, seeing that view just now reminds me. Earlier I called you Applebottom, that was a mistake and I want to apologize.”

While he said that the man had stood up and pressed himself into Jordan as he bent over, and he could feel his hand rubbing his ass. With a gasp, he stood straight up “Mr. Wesker..!”

“When it is just the two of us how about you call me Adam.”

Scared and not sure what to do Jordan pushed on the desk to try and push his boss back, but doing so only made it seem at least to Adam that this girl was pushing her ass back into him from desire. Jordan tried to spin around to face the man but the turn on the narrow heels caused him to fall forward onto his knees in front of his supervisor, his hand reaching out to stable himself his left hand’s fingers grabbed onto his belt. “Oh, I see what you want you, little minx,” Adam said a large smile on his face.

“Ahem..” Tiffany said opening the door to the office

“Tiffany this isn’t what it looks like.” Jordan pleaded to the office girl he had spent the morning with, lusting over.”

“I’m sure everything is fine here, you just fell down, right Mr. Wesker?”

Adam laughed “Can't help it if a girl falls for me.”

“Come, come let's go Jordan, we don't want to be late for our appointment.”

Jordan shakily got to his feet and walked the best he could in the heels out the office door with Tiffany, glad that she saved him because he didn’t know what he was about to do. “Look Jordan, blow whoever you want. I get it, Mr. Wesker has the power to give you a raise anytime in the first thirty days and you want to thank him for treating us today. Just be careful, promise me?”

“I wasn’t going to... wait he can give me a raise?”

“You didn’t read the paperwork you signed did you Jordan, that’s okay when I first started I didn’t either. I guess reading isn’t our assets, but we have plenty of ways to make up for it. When you started here yesterday you had a base rate of pay for all new hire administrative assistants, but based on performance the manager you are placed under has the power to give you a merit-based increase to make sure we are paying all our girls what they deserve for their talents. It only makes sense for us to make more if we are putting in more effort, right?!”

“Yeah, you are right more effort better pay.” Jordan was lost in through as they rode the elevator down, he didn’t like Tiffany implying he was stupid with the reading comment, but also wasn’t going to correct her. He was so lost in thought that he had missed more of what she was saying, only hearing her say the phrase be careful again. “Oh of course I will be more careful Tiffany.”

Tiffany gave Jordan a side hug, “Good I don’t want to worry about you, I’m glad you agree that next time you need to close the blinds first.”

Jordan now regretted not paying attention to what she had said and didn’t like what he was agreeing with her about. As they stepped out of the elevator Jordan’s phone beeped again for the twelfth time since the alarm was set up and without really thinking about it he checked his makeup before they started toward the nail salon. “If we are lucky, we will have a little extra time, we can swing into a great shoe store nearby, I think I saw some of the heels there you were checking out online earlier.

Internally groaning, Jordan went on with his day, knowing it was only halfway over.