Scene 3

“I do not like this at all!” Jackson said, as he took a few more steps to try and stride across his sister's apartment. He hated what he was wearing, he hated that his sister wanted to train him to move and act like a girl when all he really needed for Monday was to wear a skirt and look like he made more of an effort than some other guy who probably would just put balloons in his shirt. It wasn’t even nine in the morning on one of his precious days off and he was wearing the black lacy boy shorts, with his male bits tucked away. He had to watch the video his sister sent to him three times before he built up the courage to push his balls back up into his body and pull back his dick so he could have a smooth front.

Around his chest Maddy had wrapped what she said was an overbust corset. The thing made breathing a challenge, but his sister had just said how her little sister would just have to learn to breathe from the top of her chest. It was uncomfortable with how tight it was, giving him a much more feminine form and pushing some of his fat up giving him the slight impression of actually having tits. This was a nightmare and his sister was only making it worse with her comments about how he could wear that as a top like she does sometimes when they find something to give him his own girls. Then she had crammed his feet into a pair of her glossy beige high heels with a small platform for the balls of his feet while the heel itself was a thin stiletto that he was sure was at least six inches, while she claimed it was only five. Like a five inch heel could be described with the word only.

The corset kept his back straight, restricting his movements and after he fell more than a few times his sister said he was just moving too much like a man and had to take more drastic measures. So now here he was doing what he could hardly call walking in her apartment with his legs tied together with a belt around his thighs and a rope tied around him, pinning his arms just above the elbow to keep them at his sides and then looping around his wrists to keep his hands out. He was sure he looked like some simpering sissy.

“You don’t like this? Well if you weren’t such an airhead and would move like you were supposed to this wouldn’t be necessary Jackie.”

“Maddy, don’t call me that.” Jackson’s waist hurt from the vice crushing him and his feet were killing him as they were **** to be arched in such a drastic way. The belt and rope were uncomfortable, but compared to the others it was nothing.

“Shush, no talking unless you are using the proper voice Jackie.”

“Maddy… please.”

“I said shush, now march!” Madison let out a fit of laughter enjoying the power she had over her brother, snapping a photo or two of him when he wasn’t paying attention. When they were little she tried to get him to let her give him a makeover more than once, but it never happened. Now she could do whatever she wanted and he had to play along and after everything he had done to her growing up he deserved a little payback.

She wanted to go to the mall today, but she thought it would be cruel to go there and make him try on and buy women's clothes looking like his normal self and with how he was moving around like a baby giraffe just learning to walk he wasn’t going to fool anyone. She supposed she could give him flats to wear, but where would be the fun in that? The extra day also allowed her to get her little brother an appointment for a makeover. Jackson was going to be pampered with a facial, a massage, getting some nice nail extensions, his hair done, teeth whitened, eyebrows threaded and that was all before they went shopping.

She wasn’t drowning in extra money to afford all of this, but she had called her father after Jackson had passed out on the couch asking him for a little bit of money to help Jackson look professional for a work event. The phone conversation might have been the longest she ever had with her dad, he seemed eager to try and help her any way he could and she could tell he was low key drunk. It was coming up on that time of year again when their mom left them and while she hardly thought about the woman she knew her dad never was able to let go of the fact that the woman he loved, the woman that bore him two children would think so little of him as to just walk out. Any consoling on the subject was only temporary, just one of the reasons why both her and her brother moved away from home as soon as they could. It was one thing to have a helicopter parent, it was another to have one that would remind them of who they lost.

Breaking from the thoughts of last night Madison called out to her brother. “When I said shush unless you are using the right voice I meant you should keep saying the lines we decided on.”

“Lines you decided on.” Jackson said under his breath.

“What was that!?”

“These heels are just to die for, I just have to have them. Maybe in a few colors, I have been a good girl and deserve to treat myself like the princess I am.”

“Thata girl Jackie, keep that up. Remember your next line.” The soft breathy voice grew more muted as her brother walked away, allowing Madison to stop stifling a giggle.

“Jackie, you can do this, you got this girl. You aren’t the smartest, but you can at least do this.” Jackson rolled his eyes, then looked over his shoulder at his sister. He had to look through some of his hair, unable to brush it aside with his arms tied. “Maddy, I sound stupid talking to myself like that. Do I have to?”

“That is just the type of girl you are Jackie, always talking to yourself. Sure it makes people think you are a ditz, but you don’t mind people knowing the truth about you. Now I think that is the last time I acknowledge you when you speak to me like that Jackie, we might need to get you a lozenge or something, your voice just sounds too boyish. For at least the next few days your tomboy phase is over.”

“Now stop getting distracted and continue your lesson.”

He didn’t grumble, he just turned his head back forward, did his best to take a deep breath and took another step forward to move closer to the front door. Imagining himself in a charcoal gray Mustang GT on his way to the bank to cash his first paycheck as the newest member of the marketing team, or the sales team… heck he didn’t even care if he got hired over to the accounting team. If he got that and Linc was left in his dust it would be all the funnier. That was what this was for, it was **** and showed him new levels of shame, but he could do this for a few days.