Scene 10

Hearing the banging on the front door that wouldn’t go away, Lincoln opened his bedroom door wearing only a robe that he threw on over his nude body to see who wanted their attention at five in the morning. He had only taken a few steps into the living room when he stopped, seeing his roommate come from his room. Jackson’s long hair that was flowing with curls the previous night looked a mess, but he was still wearing the corset, the lacy panties and stockings. His eyes roamed over the ass and long legs with those sexy stockings on, his body reacting to the sight of the sexily clad woman despite his mind telling him that wasn’t what he was actually seeing.

Groggily Jackson opened the front door as far as the security chain would let him. Seeing his sister he closed it, removing the chain and opened the door wide so she could come in. When she had said she would come to him, he didn’t expect to see her before the sun came up. Madison smiled at her brother, as she walked in holding two packs of Slim Fast diet shakes, one strawberry flavored, the other chocolate. “Good morning little sister, how are you today?” She then looked past her brother to his roommate. “Good morning Linc, sorry to wake you. Maybe I should get a key so it doesn’t happen again.”

Lincoln waved at the girl, noticing she was wearing the same thing as the previous night, except her heels had been traded for a pair of gladiator sandals. “Yeah, that sounds like a good idea. I’m going back to bed till my alarm actually goes off.”

“You are here way too early Maddy, how are you so… so chipper?” Putting the cans on the kitchen counter she showed her top teeth as she smiled. “Simple, I haven’t gone to bed yet and I have had a good deal of coffee. You weren’t the only one to go home with someone last night.”

Oh… good for you and also I don’t need to hear about that.”

“Look, we all can’t be so lucky to live with our lover to have sex whenever you want like you Jaqueline.” She could practically see the water in his body starting to boil like a cartoon character as she teased him.

“Stop, please.” Jackson cupped his face for a second, before slowly running his fingers down his face. “If you are here can you please help me take this corset off, it is killing me.” She was a bit surprised her brother was still wearing it, but she was happy he was committed to the plan. The way he complained made her think she was wasting her time helping, thinking he would fail and end up being blackballed like he mentioned. Him still wearing it, doing waist training by sleeping in it gave her hope he was going to actually stick with it till he could move from the massive company.

“Sure, let me just put your shakes in the fridge.”

“My what?” he looked at her confused, still trying to get his mind to boot up for the day. Madison held up the back of strawberry diet shakes. “With these you should trim down, one or two pounds a week, combined with the waist training you started on your own you will be able to ditch the corsets in not too long.”

“Oh…” He didn’t much like the idea of a diet, but after wearing the **** device to give him a more feminine form the option of doing without it sounded like a good one. “Great!”

When he was done getting ready for the day Jackson shifted from one heeled foot to the other, feeling uncomfortable in the constricting clothing. Again he was wearing a garter belt to hold up his dark stockings, the pushup bra made the breast forms looks much bigger on his chest, she had showed him how to use makeup to conceal the seams, making them look like real tits in his low cut sleeveless, ruffled black or gray or dark gray blouse. She even had him in another corset, this time it was worn to be seen, the blouse tucked into it, but it went under his knee length tight pencil skirt, that was paired with a wide elastic black belt. He wasn’t used to any of it, especially the four and a half inch gray and black heels with a lace finish.

Jackson didn’t have a big mirror to look in like his sister had at her flat, but from what he could see and feel he didn’t like it. “I don’t want to look like this… I feel like I’m dressed up like some bimbo secretary that is just thirsty for men’s attention.” Madison laughed, remembering more than one comment he had made when he started at Mega Corp about hooking up with one of the sexy secretaries, how they were all just for eye candy, hired for their tits and ass.

“You are the newest secretary and you said you wanted to blend in. Also this style is so you Jaqueline, if it wasn’t why would you have picked it out?” It was his turn to glare at his sister, something they just did to each other when they thought the other said something stupid. Both knew it was her that picked out the clothes, but she was obviously having fun with his current lot in life. She did have a point about blending in, he just didn’t like the clothes, they made him feel **** and restricted.

“Executive Administrative Assistant.” Jackson corrected, but it only earned him a stern look. Jackson frowned, blowing on some of his hair to move it out from blocking some of his vision. It didn’t help, Maddy had styled his hair so it would do just that, to make him look alluring.

“Alright, let’s get you a breakfast shake to put in your purse for lunch and then I will drop you off at work.” Jackson looked over at the black leather tote bag purse, he had to not only dress like this but carry around something so feminine just so he could have things with him, he wasn’t sure why girls didn’t have real pockets.

“Let me guess, it has tampons and a condom in there.” He jeered, but it only caused Madison to laugh again.

“It does, I moved the contents from your other purse to this one. You have to be prepared, do you think we should stop off somewhere to pick up a travel size mouthwash for you?”

“Jesus Maddy, I don’t need to buy mouth wash, could you just stop with the sex jokes at my expense. Don’t you think it's hard enough on me looking like this, without reminding me that I wont be getting laid anytime soon?”

“Someone is touchy this morning, but sure I can lay off.”

“Thank you…” He felt exasperated to have to even ask her, he wanted to yell and tell her to back off with the teasing. That sadly was just part of their relationship with one another, both always giving each other a hard time while still being there for the other, plus if he tried commanding her to do anything she would just do it more to spite him.

Picking up the purse he moved it to the crook of his elbow like his sister had shown him, he turned to start making his way out the door when his sister stopped him. “Hey I have a favor to ask, and it is a big ask.”

Jackson motioned to his body all dolled up. “Think I might owe you something big for the help destroying my life at my request.”

“Well my lease is up at the end of the month, and I was going to move in with my last boyfriend…”

“The one you cheated on, so he dumped you?” She gave him a hard look.

“What kind of man doesn't want a three-way with two hot girls? He didn’t want to join, but that didn’t mean I still didn’t want to have fun with her.”

“I didn’t say he wasn’t an idiot, just that you cheated on him. So what do you want? A place to crash for a while? Maybe this time get someplace more affordable or get a roommate like I did.”

“Well I was thinking I could move my stuff into your room, put my things and yours into storage. Having me around would mean you always have someone to help you get ready, till you are ready to preen all on your own.”

“That sounds more like moving in, and me giving up my bedroom to you.” Madison gave a small shrug.

“It isn’t like you can keep your boy things here, what if someone from work came by.”

“I’m not inviting anyone over Maddy…”

“Have you considered if they came by on their own? What if someone in HR that knows you are supposed to be transgender doesn’t believe you and comes by? What would happen to you then?” Jackson took a few small steps backwards, the only kind of steps he could really take in the heels and restrictive pencil skirt and sat down on his bed thinking about what she said.

“They would fire me for fraud.”

“See? So me putting up my things would actually be helping you and I would pay rent too, so it would be split three ways. Combine that with the extra money you are pulling in and you might actually be able to have a savings account like a real adult.”

“I umm would have to talk to Linc about this, I’m sure he would love to have you around. We would need to get an air mattress for a place for you to sleep, our couch is not comfortable to sleep on.” Madison waved her hand in the air to dismiss the idea.

“I will be bringing my bed, I have a much better one than you. Some nights we can snuggle together like when we were little living in that two bedroom apartment. I don’t mind sharing a bed with my little sister, but other nights you can sleep with your boyfriend.”

“Yeah… you can feel free to sleep with Linc and I will take the bed, I promise he will welcome you. He has had the hots for you forever, no matter how much I tell him you are a major pain in the ass. “

“Sorry sis, I’m not going to steal the love of your life.” Jackson closed his eyes, she had only promised to not tease him about sex, he should have been more specific earlier.

“Ya know what, sure. I owe you and that could be a big help, but we will discuss the details later.” Jackson thought how having his sister around would be aggravating, but it would only be for a short time till she found another place and while she was here cheaper bills would be a welcomed change. He had no doubt there would be hurdles, but he could work them out later. They were siblings and looked out for one another, and he really did owe her. He couldn’t imagine it going well for most people if a brother asked his sister to make him look like a woman so he could keep their job.

“Fantastic!” Madison moved over to her feminized brother, pulling him to his heeled feet and giving him a big hug. “I will take your house keys and make a copy today. Thanks sis!”

When Jackson was coming into the building he scanned his badge to get past the turnstiles; it had been updated with a new picture on Monday. As he placed one foot in front of the other, swinging his hips and hearing the sound of his heels echoing the tiles he felt nervous. Like someone was going to confront him about being dressed up like a girl. Only his boss, Mary in HR… and Linc knew who he really was, but that didn’t mean others wouldn’t figure it out, it wasn’t like he suddenly became a different person just because he wore different clothes and makeup.

“I just love that skirt.” The comment came from a pretty platinum blonde girl with a spunky haircut and almost golden eyes. They definitely caught his attention, enough so that he hardly paid attention to what exactly she had said other than it was a compliment. “Your eyes… they are…”

“Contacts, but I just love the look, but Mr. Edwards.. My boss said I can’t wear them again, he said I looked pretty, but it wasn’t professional.”

“Oh, that is too bad, they make you look like you could be an angel.” The girl leaned forward on her desk, allowing him to get a good look down her blouse at her assets.

“I know right!? That would be amazing. Say, I’m Lily, or Lil.” The girl put one hand over the nameplate on her desk covering her first name. “Just not Liliana, I asked Mr. Edwards to have it fixed, but he said they didn’t do nicknames, very unfair cause I know they do, he just doesn’t think it is professional.” She held up her hands making air quotes as she said the last word. Jackson had almost forgotten the way he looked with the spunky and pretty girl being so friendly to him. He had walked past her, and admired her more than a few times, but she never so much as said a word other than a friendly greeting, the same thing she did to everyone.

“I’m Jack… Jacqueline.”

“You're new right? Your badge says it was made on Monday. I hope you like it here, some of the boys can be a challenge. Mr. Edwards is nice enough, I don’t mind when he looks at me, he never touches, not like some of the others here. You will have to be careful, some of them want…” He watched as the she pursed her lips together and tilted her head to the side like she was trying to move it so the thought would come loose. “Well extra effort, the kind we can do to help relieve stress, or spend time with a client they want to impress. Listen to me, I don’t want to scare you off. I’m sure whoever you will be working under will be like Mr. Edwards, well behaved, but strict or they might even be better.”

She looked over her shoulder at the three screens she used for work. “I need to get back to it, but I will message you later and maybe we can do lunch!”

“Sounds fun!” Walking away over to the elevators Jackson felt odd about the encounter. He would love to spend more time with the girl, but he didn’t see him as a male. As someone she wanted to be with… it was good that she didn’t know the truth, but at the same time it felt wrong to not be seen as a possible partner. Jackson was so wrapped up in thinking about how she didn’t see him as a man that he didn’t notice the man behind him as he kept pace, his eyes glued to what he thought was an attractive girl's ass.