Scene 7

Jackson knocked on his sister’s apartment door, taking a sip of the coffee in his left hand to try and kick his mind into gear. He was tired after a weekend of sleeping on his sister's couch and not being able to get decent sleep with his mind going over the last day over and over again. After hearing the security chain being removed the door opened. “Morning Maddie.” He said to her handing over a brown paper bag and a coffee to her he had in his other hand.

“Aww I was hoping to see my little sister this morning, not my boring little brother.” She said, seeing him wearing his normal garb.

“Mocha caramel dark roast coffee and a blueberry muffin in the bag. Hand them back if you want to give me shit.” Madison didn’t move from her doorway, she just looked her brother over for a second as she sipped the sugary coffee. He was wearing a blue t-shirt with the logo of some cartoon he liked when he was younger and some jeans.

“I will keep the offering and hold back on my god given right to tease my younger sibling, but are you sure you want to go shopping like that?” Jackson looked down at himself, then to what his sister was wearing. She had on a pair of cut off jeans, a tanktop and black sandals, the light from the hallway lights glinting off her bright red toenails.

“Yeah, it is fine. I’m not trying to find someone to take the last name Heart or anything, especially when we are going to go buy clothes for my new job.” When her little brother called her and told her the story of what happened at work she was thrilled to help with shopping, though he did hang up on her first when she wouldn’t stop laughing.

“Dresses, skirts, heels, makeup, jewelry, your own panties and bras.” Still standing in the hallway Jackson gave a tired glare at his sister.

“I told you last night, that won't be needed, pants will be fine and I don’t need heels or well most of any of that.”

“Jackie, Jackie, Jacquline.” Madison shook her head while thinking of that line from the tv show that was on HBO, sweet summer child.

“I told you to not call me that, what happened to not teasing me?”

“That went out the window when you decided you know better than me about what a young woman needs to wear to the office.”

“Like you would know what to wear to the office, you have never had an office job in your life.”

“I have to stop being a shit. I have an office job now.”

“Bullshit, you work from home.”

“I get to work from home, but that doesn’t mean I don’t have to go to the office every once in a while.” After years of making a living mixing drinks she finally had a job that could turn into a career and being able to work from home as a junior programmer made the job that much better. “Besides you have told me how your office is old school with dress codes. I’m betting girls in your office are either highly encouraged to not wear pants or the dress code specifically says skirts and dresses. Now that you are going to be working as Jacqueline Heart, that dress code applies to you.” She would have poked her brother in the chest, but her hands were full with the morning treats he brought her.

“But…” Madison saw how crestfallen he was and tried to reassure him with a grin. “I know this isn’t easy for you, but I promise I will do everything I can to help you not get fired and ruin your chances at a future. Though you have to promise me you aren’t going to argue with me about girl stuff, I am the one with all the experience.”

“Fine, I promise.” Jackson huffed, He considered the females in the office, some of them did wear pants, but it wasn’t often and tended to be those at the supervisor level or higher that did it. He thought she was wrong about the dress code, he couldn’t say about what was encouraged or not other than his observations and those were more directed at checking the attractive woman out than examining what they were wearing. There was a chance she was right, he hadn’t really read the employee manual, but he wasn’t going to admit it out loud.

“Good then the first thing you need to do is run on home to get that corset I lent you.”

“Why?”

“Because when you use it you're just about my size and it gives you a much nicer feminine form. Something you need when trying on clothes for what looks best on you.”

“Can’t you just pick stuff out?” Madison gave her brother a look that just said ‘are you kidding’

“Umm no, we are going shopping and doing it right. So you go get the corset and come back here, then I will make you look more presentable. Unless you are okay with everyone seeing a boy trying on dresses? There is nothing wrong with that, specially you being transgender and all that, but people will stare.”

“I’m not trans anything Maddy.”

“What would happen if that lady from HR or your boss heard you say that? Or someone heard it and told them you said it?”

“Fair point.” He had to admit that would get him in trouble, he just needed to do this so he could start his new role as Mr. Dunn’s Executive Administrative Assistant. When he had come back from lunch and was shown what his job would entail it was answering phones, taking messages, organizing mail, filing paperwork in the filing cabinets on their floor and working with other secretaries… even Dunn didn’t bother to use the fancier title when talking about his role. He would be working with some of the females he ogled around the office to keep the mass of filing cabinets organized that were kept on another floor. Then of course his other duties were to take meeting minutes, get coffee and if seeing what the other girls did was any indication he would also be cleaning up conference rooms and having to do other little things he was ordered to do.

“Glad you agree, now go back home and so you know. You did a horrible job removing your makeup.”

“I’m well aware… but forgive me if I’m not an expert using makeup like you.” He said sarcastically. Jackson was upset he had to go back home and then come back here in order to get dressed up to go shopping. While his offer letter said his official start date was yesterday he hadn’t really done anything and today he was told to take the day to look presentable.

“Don’t worry Jacqueline, when I’m done with you other girls in the office will be asking you for makeup tips.”

“Joy, oh joy. That would just be a lifelong dream.” Jackson said in a deadpan voice before just turning and walking away from his sister to head home.

“I know and I’m more than happy to help. It is what big sisters are for!” Madison called after her brother as he moved towards the elevator. When he made it down the hall she went inside, opening the little brown bag to pull out the blueberry muffin, thinking about how the little jerk could be considerate at times.

Later Jackson stood in front of a large free standing mirror looking himself over in the purple dress with the white floral pattern. It wasn’t the first or second time that he was transfixed by the feminine face he saw in the mirror. With makeup his face seemed softer, his chin not as prominent, his lips seemed fuller. He would absolutely want to ask this girl out and that was a big part of the problem, If he made an ugly girl he doubted any of this would have happened. He was the type of guy that liked being the center of attention. He wasn’t going to lie to himself that there wasn’t a tiny thrill with getting it for how he looked dressed up, but it also made him feel so much more ****, making him pull in more instead of being his normal extrovert self. Dressing like this made him feel like he was another person, and even if that was part of the point, he hated it. Sliding his eyes over to his sister in the mirror he held in a sigh at the idea that even in heels he was the same height as his sister, him wearing white heels and her black. “Can I at least go shopping without wearing high heels?”

Madison smirked, thinking how he didn’t just say he wasn’t going to wear them or demand something else to wear, no he asked her like he needed permission. He had never acted subservient to anyone as far as she remembered and it gave her a sense of power that she was just loving. “Try asking again, but this time in the right voice little sis and tell me how much you are going to love going shopping for new dresses and shoes.”

“I really, can’t thank you enough Maddy for going shopping with me today. You have just always had a better sense of fashion than me and going out with you to get some more cute dresses and heels for work is just so exciting, I’m just so looking forward to this. You know me, I just love to shop, shop, shop.”

“How could I say no to my cute little sister when she flatters me like that.” Getting her brother to talk in that husky voice like he was a phone sex operator was truly the cherry on top of all of this.

At the mall Jackson had to resist the urge to pick the piece of fabric that was his sister's panties from between his butt cheeks. She gave him a thong panty, telling him how he could keep this along with the other pair she had given him. He was not enjoying the feeling of it, or having to wear any of the female garments. the purple floral patterned bell sleeve dress that came down to mid thigh or the sandals with a slight wedge heel. The shoes were much better than what Maddy was originally going to have him wear, but still he disliked it. When he had complained about wearing heels again Madison had told him how it didn’t matter how others dressed. Jacqueline needed to present as extra femanine and that he needed more practice walking like a lady, at that he decided he best leave it alone before he was wearing something he really did not want to be walking around in.

Jackson hated feeling the weight of the stupid breast forms she had gotten him and the pull of the bra straps on his shoulders, the compressed feeling of the corset and the million other feelings he shouldn’t be feeling, but his sister had declared that her little sister looked cute enough for a day of shopping looking like this, so he had little choice in the matter if he wanted her help and sadly he had to admit he needed her help.

As they started walking toward one of the major box stores attached to the mall, Jackson bent to the side just for a second feeling uncomfortable. “You know I hate this corset.”

“No problem Jackie, we can get a few more so you have some options and I think starting today you my little sister on a diet.”

“A diet! Why? I’m skinny enough as it is.”

“I like your confidence girl, but you could afford to lose a few inches. It won't be something drastic… no I take it back. We will start you with a crash diet, get you some supplements to make sure you have everything you need and then we will move you to a more balanced diet. More fruits, veggies and less meat.”

“Maddy, you remember that this is all temporary right?” Jackson stopped walking as he tried to give his sister a reality check.

“Two things.” Madison held up her index finger and middle finger. “One you said you wouldn’t argue with me. Keep that up and I will see about getting your tongue and bellybutton pierced and if you refuse to do that I will just stop helping. So you can either do as I tell you little sister without arguing with me, or you can argue still do what I tell you and we can go get you some new piercings or you can do all of this on your own. So what will it be.”

“What is the second thing?” Jackson was getting angry and as he brooded on what she said he ran his tongue across the front of his teeth with his mouth closed. The last time they were at the mall she had his teeth whitened and they just felt a little different after.

“The second thing.” Madison lowered her index finger, turning the hand around to flip her feminized brother off. “Is that the paperwork you signed said you have to pay back the money you were given for clothes if you left the company before ninety days. That means you will be my sister Jacqueline Heart for at least three months. So the question is, do you want to make it through this on your own?”

“No…” Madison moved closer to her disguised brother, leaning in with a big smile. “Good, because I’m really enjoying having a little sister to play dress up with.” Jackson groaned, but followed along with his sister into the store. Resisting the urge to do anything other than smile as she held up one dress and then the next and on and on. He was grumpy, but wasn’t even allowed to show that as she said that would only draw more attention to himself. Every outfit she picked out he had to try on to make sure it was just the right fit and look. All of the jackets fit much tighter than he was used to, the sleeves just a little shorter and even that was the best of the experiences. The long skirts she had him put on that he had seen more than a few girls at the office wear were called pencil skirts and were much tighter than he would have liked. The length he could get behind, especially compared to the shorter skirts and some of them were way too short in his opinion, but Madison only said how her little sister had legs that should be shown off. So his new skirt collection was full of skirts that made walking difficult with how tight they were and things short enough that he was sure HR wouldn’t approve of.

“Okay, no, just no Maddy. I draw the line at you trying to buy me a little black dress, in fact I don’t need that sundress you had me try on before either. I only need things for around the office.”

Madison pressed her tongue to the inside of her cheek as he looked at the black dress in her hands again, then held it up to her brother once more despite his protests. “Sure you do, what if you have to go out with your boss after house for dinner with a client. Or need a sexy little number for a date.”

“No one is going to date me while I have to dress up like this at the office, and even if they did I wouldn’t be wearing a dress.” Madison gave her brother a hard look.

“From what I understand you have a boyfriend now. You just kinda pointed at him and told him you were his girlfriend. I would never have the courage to do that to a boy I like, but you get it girl. You got yourself a boyfriend, so I imagine there will be some dates.” Jackson closed his eyes and counted to five before he responded, but he only made it to two before he mentally whimpered at his life and bad luck.

“That isn’t real and it was more of me blackmailing him to do it.” Madison shifted her head from left to right as she thought about that, then her smile grew.

“Blackmailing someone to date you, very nefarious and I wonder if he thinks that is hot.” She could see he was about to say something so she just kept on talking right over him. “You don’t want a bunch of people at the office hitting on you and I can really understand that, but you are going to have to do more than just say you have a boyfriend. You are a girl now, so you can put some photos of the two of you on your desk, get your little friend to send you flowers. Go on dates where you are likely to run into coworkers that way everyone knows he is yours and doesn’t try and take him from you. Or you know, the other way around.”

“But… I don’t want to do that.”

“Then you shouldn’t have claimed a man as your boyfriend, but you can always call up Lincoln and tell him you are dumping him. It will be a shame though, I think the two of you make a cute couple.”

Jackson looked at the dress in his sister's hands and took it from her, adding it to the pile of outfits he would be purchasing that day. “No, I can’t do that.” He said thinking of how Dunn had literally groped his ass the previous day.

“Don’t act all glum girl, just a few more outfits here and then we can hit the shoe store, but first give me your phone.”

“For what?”

“No arguing, just hand it over.” Jackson huffed again, before reaching into the purse his sister had given him and handing over his phone.

Jackson: Hey this is Madison, you free tonight?
Linc: Yeah, absolutely! Got something in mind?
Jackson: Was thinking about a date tonight, go out to a bar coworkers are at and then whatever.
Linc: Sounds good, yeah!
Jackson: Glad you are loving the idea, be ready around five thirty.
Jackson: Your girlfriend is looking forward to your first date
Linc: Wait, what!? I thought I was going out with you
Jackson: Sorry I don’t do men who are in a relationship
Linc: Fuck, I hate your brother
Jackson: No one is asking you to fuck my little brother, but you enjoy your time with my little sister.
Linc: Not funny

“There I have your first date set up with your boyfriend. Oh and we will be stopping off at the cellular store, we need to get the name on your account changed. Can’t have your caller ID showing up as Jackson anymore.” Jackson’s sour mood just got worse as he slid his eyes away from his sister back down to the black dress he put in the pile himself.

“If you don’t want to wear that for your date tonight I’m sure we can find you something you want him to see you in. Maybe some lingerie.”

“Could we instead just move on to shoe shopping?” He really didn’t like the idea of spending time picking out a dress for a date. Especially not when the longer this went on the more his sister wanted his opinion on each thing she picked up.

“Now you are starting to sound like my little sister. Let's go do that and then we can circle back for something for tonight.” Madison shook her body as she got more excited. “Let’s go pay for all this with your windfall and then we can move on to shoes, lingerie and makeup!”