Scene 2

“So let me get this straight, you want me to make you look like a pretty little office girl?” Said Madison, Jackson’s older sister by two years.

“That isn’t what I said at all Maddy.” Jackson glowered at his sister as they both stood in her studio apartment. Once he decided he was going to go through with it he texted his sister to see if she was home. He knew it was going to be embarrassing to just ask her for help, but he couldn’t really do a good job on his own. When she said she was, he headed over to her place with the Chinese food instead of heading home. Fried dumplings were going to be a better bribe for her and Linc was a big boy, he could fend for himself.

“Sorry, all I heard was my baby brother asking me to doll him up to be a pretty girl.” She let loose a series of giggles as she divided up the dinner onto plates.

“I said…” He added extra emphasis to his words. “That there is a contest kind of thing at work for dressing as the opposite gender and if you do a good job, you get put in a raffle for a Mustang GT and if you do the best, you get two chances to win and like two thousand dollars.” He watched his sister divide the food evenly as she pulled them from the containers with chopsticks.

“You know we can eat out of those containers, right? You don’t have to dirty plates.”

“Not all of us live like slobs Jackson. So, if I help you, you get a chance to win a sports car and I get what exactly?” After asking the question she picked up a dumpling with her chopsticks, dipped it into the sauce and took a bite. Making eye contact with her brother as she chewed on the morsel.

“You are getting dinner and the joy of knowing you are helping your baby brother. Plus the knowledge you get to torment me with makeup and whatever. You know you are going to be laughing about this for days after you see me in one of your dresses.” He gave his sister a once over, he was a little short for a guy, but not so short it really bothered him. When he took the time to think about how he was the same height and build as his sister, like he was now then he had a problem with it. Today, today though it would come in handy, so long as she agreed. He couldn’t wear what she had on today to the office, but he was sure she had something professional in her closet. Today his sister was wearing a low cut thin strapped sleeveless blouse that showed off her cleavage, some tight jeans that ended above her ankles and a pair of peep toe black heeled boots. Their build and height were about the only thing they really shared, their hair color was similar, but she kept hers in a short sheik look compared to his own that was much longer. She had inherited their mom’s blue eyes while his were brown like everyone else in the family.

“I want the weekend.” Madison said now looking at her little brother like he was prey.

“No, and for what?”

“If I get to have you as my dress up doll so you can be pretty for everyone at your office, then I want you to do everything I say for the weekend. That way you can move in heels without breaking your ankle or worse ruining my shoes.”

“I don’t need to wear heels Maddy.”

“If you want my help, you will be and if you argue with me further, the heels will be higher.”

“I’m not arguing with you, I can just wear… what do you call them flats or you know just normal dress shoes. I was thinking maybe I come over here or you come to my place early Monday morning, I will have coffee and bagels or something. You dress me up, you get some laughs and then I head off to work.”

“Four inches.” She said, crossing her arms under her ample bosom.

“What? I don’t understand.”

“The heels you are going to wear on Monday will have a four-inch heel and if you keep arguing with me it will be five. Of course, you can go do this on your own.”

“This is not worth it, coming here was a mistake.” Jackson reached over taking the last dumpling from his plate and hers before shoving them both into his mouth. Chewing slowly while starring into her eyes. Madison for her part narrowed her eyes down to the now empty plate and then looked back to her annoying little brother.

“Time for you to leave. You can do this on your own, but I can’t wait to hear what Dad will have to say when he hears his little boy decided to become a working girl.”

Jackson stopped chewing for a second and swallowed everything in his mouth. Almost coughing as he **** it down. “Don’t even joke about that, besides he would probably just give me a hug and say it was so nice to have a daughter that wasn’t a dyke.”

“Jesus, I dated one girl, and you will just never let that go. Wait, why am I talking to you? I said get the fuck out!” Her voice started to raise as she pointed towards the door of her small apartment.

Walking towards the door Jackson was grumbling about why he should have even bothered, as he did, he saw an envelope on the counter from his father. Much like the ones he had back at his place. Their dad enjoyed writing actual letters, saying everything meant more when it was done by hand. It wasn’t that he didn’t use a cell phone, but the conversations were never more than a minute or two. Everything else was in the letters, he used to write back, but lately all he really did was cash the checks that were sent. Far as he knew his sister still took the time to write him back home. That was one of the reasons he was doing this, so he didn’t have to keep cashing those checks, so he could stand on his own. Jackson stopped moving, touching the opened envelope.

“Does he still send you money?” He asked without turning around.

“No, he got the message after about six months of me not cashing his checks. He says he just wants to make sure I am taken care of and that he is there to help.”

“He still sends me money, and I take it. My job doesn’t pay enough, not really. I was hoping this thing at work would show I’m a team player and maybe get a promotion or something.” He turned around to face his sister, letting out a held breath. “To be my own man, I need you to help me look like a woman for work. Would you please do that?”

“After what you just pulled? Four-inch stilettos and I get you for the weekend.”

“Guess you win.” It felt a little funny to Jackson to be saying that after he made Lincoln say he was the winner. He had to promise dinner to get him to say it, he bailed on that and now karma had turned on him.

“Great, no time like the present. Why don’t you get into the bathroom and strip down, I will hand you things to use.”

“Now?”

“Yeah now. Get moving, the sooner I have a little sister around for the weekend the better.”

Jackson looked back towards the bathroom. “I’m already regretting this.”

“Yeah well, I regret Mom ran off when I was seven, but that doesn’t change the price of milk. Get moving.”

Doing as he was told Jackson was soon standing naked in the shower with the curtain drawn with a pinkish cream all over his body. It had been a little over five minutes and it was starting to get a little uncomfortable. “Hey Maddy! How much longer do I have to keep this goop on?” He yelled over the shower, he wasn’t sure if she was still in the bathroom or somewhere else in her apartment.

“Ten more minutes.” The voice came from outside the bathroom, so she wasn’t in there with him anymore. He was a little happy about that, he didn’t like the idea of the only thing keeping her from seeing him naked with a yellow shower curtain.

It felt like forever with him just standing there with nothing else to do but question his choice, but when he was told to rinse off he felt it was well past what she had said, but he didn’t have any way of keeping time. When he turned on the shower, he started to wipe off the cream with a wash rag and while he knew the point of all this was to get rid of his body hair, he was not ready to see it wiping off and leaving his skin hairless. He wasn’t the most hairy guy, but without his dark hair on his chest, arms and legs he felt like he was somehow more naked than he was a minute ago.

“When you get out, I have put some moisturizer on the sink. You need to rub it into your legs, feet, arms and hands. Then I have a different one in a pink bottle for your face.”

“Is that really necessary?” Jackson asked, feeling apprehensive about what he already did.

“If I tell you to practice cartwheels this weekend you should consider it necessary. Now I have sent you a video on your phone so you can tuck away your… well tuck away your dick. Then you can put on the panties I have laid out for you. After you put them on, they are your panties, I will not be wanting them back.”

Slumping his head on the cold tile wall he listened to his sister as she went on and on about what he had to do next. He could hear the barley contained glee in her voice as she talked about tonight, they were just doing some basics and tomorrow how they would go all out and go shopping so her little sister could get her own underwear.

“Maddy, I don’t want to go shopping for women's clothes.”

“It isn’t about what you want right now, this weekend is about what I want to do and how much payback I want to get for years of you being a little shit. That did sound like arguing, and I was going to let you wear some cute sneakers tomorrow to the mall. Guess we will have to do a crash course on heels tonight. Just remember little brother, every time you argue with me all I really hear is you asking me to make you even more feminine.”

Hearing the bathroom door close, Jackson stepped out of the shower, the first thing he did was pick up the panties his sister left. They were black lace boyshorts with a small amount of pink woven in. They were not normal cotton panties; she had left him something sexy. Most likely to torment him, but the very idea she had panties like this to just give away was a little unsettling. He could easily acknowledge his sister could be a smoke show as Linc put it, but he didn’t want to think about what kind of lingerie she wore. With a groan he tossed them back down atop the closed toilet and pulled off the towel from the rack, patting himself dry like he was told.

Things were just starting, and he already felt he was out of his depths. Cracking open the door and trying to ignore the feeling of cold air on his hairless body he called out to his sister. “I want it to be noted I’m not arguing, I’m just asking if you had… I dunno some different underwear?”

“We can pick some out in your style tomorrow, for now wear what you are given.” He couldn’t see his sister, but she couldn’t have been far considering the open floor plan of the apartment. The bathroom was really the only other room, in fact it was the only other door in the place besides the front door.

Grumbling to himself he talked in a higher pitch voice to mimic and mock his sister. “Tomorrow we will get some in your style.” He glowered at the pair of panties before getting to work with the lotion. Another ridiculous thing girls did, two different lotions one for the body and one for the face would be crazy enough, but he also knew Maddy had a third lotion that she put on at night after she took off her makeup.

“You set yourself up for a nightmare, you asked for this, and you did it twice.” Jackson said, pointing at himself in the bathroom mirror over the sink. “I better win that stupid car at least.” He said, shaking his head.