Scene 25

The job of an administrative assistant wasn’t difficult for Jackson, but today as he went about his duties he discovered more than just a few mistakes he had been making:

Files put back in the wrong places or just the files put in backwards, double bookings on his bosses calendar, and notes from phone calls put on sticky notes instead of in emails.

To him it looked like he was taking over a job from someone who was struggling with the tasks and it wasn’t until now, when his mind wasn’t medicated that he could see it all. He knew it wasn’t just the medication, but the constant whirlwind of thoughts that plagued him, was some guy checking him out? Did someone see through his disguise? Should I check my makeup? And a thousand other thoughts.

Today he was free from some of that, but not all. After he had left Mr. Dunn’s office and closed the door, the older man hadn’t so much as popped his head out, though some of that he knew was from being over booked for meetings thanks to past him’s mistakes. Still though, his mind kept going back to his previous thoughts, wondering what he had done wrong to be rejected.

Certainly he enjoyed the fact he did not have to perform THOSE certain duties, or at least that shame and guilt at the potential consequences for it. Focusing on the little things kept Jackson from panicking or getting overwhelmed, though he did take the time to schedule and move up his next appointment with Kimmy, his therapist. She couldn’t know everything he was going through, not without opening a different can of worms, but he was hoping she could be of some help. It was Kimmy that had wanted him on different medication, and considering the choices he had made on what the doctor prescribed it felt like she had been right.

Not wanting to just dwell on the positives and negatives of not sucking his bosses dick, Jackson attempted to arrange time for company on his lunch break. It turned out Tabitha wasn’t in the office today, a reason why he hadn’t seen her in the break room that morning and Lillian had turned him down. Her saying how she was trying to diet and didn’t trust herself to not just order the largest bowl of pasta available. Her response made her earlier comments about eating a doughnut and hating him for being skinny come more into focus. Spending time with a gorgeous girl would have been a good turn for the day, so instead he tried for his back up. Jackson had just seen Abe the night before, but talking with him about football or even his music collection would be a heck of a lot better than sitting by himself thinking about what he should have done. ‘Should I have just gone for it when he said I wasn’t convincing enough?’ The thought turned his stomach.

Before he could reach out to a third person though an email came through that put a stop to every other thought. It was a correspondence between human resources and the doctor's office discussing his next steps for transitioning. Jackson’s mind felt numb as he scrolled down to read it from the bottom up. What he read horrified him and he couldn’t help but skip over several emails like jumping to the back of a book once a mystery was introduced in a story. The doctor was under the impression that he wanted breast augmentation surgery and wanted it sooner rather than later and had been discussing it with human resources and his employee insurance about coverage and dates. The last email was from Mary in HR, Jackson read it, then read it again before just staring at his screen.

“Good morning Ms. Hart.

I hope you are having a wonderful day, as you know, I am assisting to get everything sorted out for you. Though I can imagine that this email will make any type of day you are having, better.

As you are aware, part of your employee compensation package here at Mega Corp is full assistance in handling the financial and logistical hurdles that come with your transition. After working with our insurance provider and your chosen medical professional, I am happy to present you with the date of your surgical appointment. While normally you are not entitled to use more than a few days of your paid leave time within your first ninety days I have spoken personally to your supervisor, Alexander Dunn, on your behalf. He mentioned a lot of changes happening relatively soon, things I can not go into now, but he was not only willing to allow you paid leave, but is also donating some of his own accrued vacation time to your cause.

If you need anything else please feel free to reach out.

I am truly excited for you.

-Mary”

What Jackson had no way of knowing was how surprised Mary was at Dunn’s willingness to be supportive of his employee after their first discussion on the topic of a transgender employee working under him. The only thing Jackson could focus on was the date listed in the email, it wasn’t just some far off thing that could be ignored because Linc would be in charge by then. The date of the appointment was before his friend would even be back from his work trip, let alone be in charge of anything. Suddenly that new scheduled time with Kimmy felt way too far off and the receptionist said it was the soonest she had an opening. ‘No, no, no, no, I won’t…”

The tight white hairband lightly squeezing his head and keeping his hair in place suddenly felt like a vice as Jackson became very aware of every single article of feminine clothing. The gentle touch of the hosiery and softness of the panties. The bra around his chest, his chest that had fake breasts glued to him and pulling on his skin, the restrictive nature of the skirt and blouse that hugged his body and the support and pressure from the corset around his waist and lastly of his arched feet in the heeled boots. He hardly noticed the feel of the makeup or taste of the lipstick, but in this moment with his heart picking up speed he felt it too, tasted it and smelled it along with the perfume that hung in the air around him. Swiveling his computer chair around, Jackson looked once again at the closed door to Mr. Dunn’s office. His own words he had just spoken of refusing what he had just read haunting him. ‘I have to… he wanted me to prove I wanted not just him, but this… does he know I’m faking it?’

While the beats per minute from his heart jumped up, so did Jackson. Getting to his heeled feet he moved too quickly to his bosses door, putting one hand on the solid wooden object. Jackson could hear his heart beating in his ears, the world felt off and very wrong. It was like playing a video game when boss music started, but no boss or monsters appeared, you were just in some dark corridor just waiting for things to end. “Stop, stop, stop.” Jackson whispered to himself, now rushing back to his desk and throwing open his bottom drawer so he could get to his purse and his phone within. Quickly he called his sister, when it went to voicemail he hung up and called again.

“Come on, come, answer!” He said to himself bouncing on the balls of his feet as he tried to retain some sense of control over himself. As his anxiety skyrocketed his body started to shake and he desperately pleaded for his sister to answer her phone so he didn’t go into a full blown panic attack. ‘Please, please, please answer!’

Back in the shared apartment Madison looked down at her phone muting it as it rang for a second time, her little brother, now sister was calling her. ‘Leave a voicemail.’ She mentally commanded her sibling as she sat on the sofa in the living room, legs crossed in indian style, still in her pajamas. She was in the middle of a meeting with two others, her boss and one of the senior programmers as they went over some of the errors that occurred from the most recent update they had implemented in their test environment. Errors that would have impacted clients if it had gone live and not tested, something her boss wanted to do because of a tight deadline. If it wasn't for her senior, the update would have had a financial impact and now wasn’t a good time for a phone call. When the phone rang for a third time she huffed, blowing some of her unbrushed hair from her face.

“I’m sorry to interrupt, but I have to take a phone call, it is an emergency.” She said after unmuting her microphone. ‘It better be an emergency.’ She told herself as she clicked the green accept button on her phone.

“Jack…ie.” She corrected herself before she called her sibling by their old name, their dead name. “This better be important!”

Hearing his sister's voice Jackson let out a breath he didn’t know he was holding and immediately marched himself as quickly as he could in his chosen footwear and skirt to the stairs where he could have some semblance of privacy. “THEY WANT ME TO HAVE SURGERY!” He said much louder than he planned as his anxiety burst out in those six words. Jackson’s voice echoed in the stairwell, causing him to move over to the railing so he could look up and down, hoping no one else was in the area. Not seeing anyone he went to move down the stairs thinking he could make his way outside to have a more private conversation but the second he picked one foot off the ground to step down he felt vertigo. He had gotten used to walking around in heels, but the way they **** his body to position itself left him feeling unbalanced as he teetered on the edge of the stairs. Quickly he grabbed onto the rail, deciding where he stood was a better choice than breaking his neck.

“Hey, hey. No yelling or the conversation is over.” Madison said in a harsh voice before her tone softened as she continued. “Now tell me what you mean by someone wanting you to have surgery. Are you okay? Did you have a doctor's appointment?” She asked now regretting snapping, worried that Jackie got some bad news at a doctor's appointment.

Gripping the rail to the stairwell Jackson took a few mincing steps backwards till his back pressed against the wall to the side of the door he had used to enter the area. “Yeah, yeah…” Jackson answered, his voice small as he let the vertigo pass. “Well not really, but… Maddy, I don't know what to do.” He said as his mind flashed with the option of just going home and crawling into a ball and sleeping till everything was okay. It was the same feeling he felt long ago when he found out his mother had abandoned him.

Much of the time Madison could hear a teasing and jovial tone to her siblings voice, she knew how well he… she was at hiding how they felt behind a smile and small pranks, many ill thought out. Hearing the small quivering voice on the other end of the phone quickened her pulse. “Jackie, what is going on? Are you okay? Do you need me to come get you?” She asked already moving to her bedroom so she could throw on some clothes that weren’t the pajamas she had been lounging in.

“No… maybe? I… I got an email they… ahh.” Jackson swallowed hard remembering the email he had just read. “Mega Corp and the doctor has signed me up for surgery to get tits!” While he had some intensity behind his words, they were spoken in a volume close to a whisper, the last thing he wanted was his voice to carry across the stairwell once more.

“Tits? Oh my lord Jackie.” Madison sat down on the edge of her bed before falling backwards to lay down, her legs dangling off the side as she pressed her free hand to her chest, feeling her quickened heartbeat to start to calm. “You can’t scare me like that! You can’t go and pretend like good news is something life threatening. I swear you almost gave me a heart attack. I thought the doc told you that you had cancer or something.”

“Cancer? What? No, but Maddy, listen this isn’t good news.”

With a shake of her head and a roll of her eyes Madison kicked her feet in the air, feeling like the little shit had gotten one over on her again. “Sorry, sorry, great news then.”

“Maddy… no! They want to mutilate me, turn me into some sort of freak I can’t.”

Hearing that Madison frowned, the conversation started to feel like a roller coaster. She knew this was good news and thought Jackie was pulling her leg, but it sounded much more like dysphoria, or how she understood it from her small amount of research she had done to try and understand her brother as he transitioned into the woman he wanted to be. She had read about how the feeling could be a paradox, how at times her sibling would feel at war with herself. Wanting her outside to match how she felt inside, and yet at the same time feel wrong when taking those steps, as if something was wrong with her. “Okay sis, you need to take a few calming breaths.” She said adding the word sis so that her sibling understood how she was accepted for who they were. “You are not a freak, no one is turning you into a freak. I know things are going fast for you, but your doctor wouldn’t move this quickly if he didn’t think you were ready and wanting this. Did you tell him you were ready?”

“No.” Jackson’s brown eyes darted from left to right after he gave the knee jerk answer. His meeting with the doctor was a bit fuzzy, but he did remember grabbing his fake chest in front of the man, but he couldn't remember what they really talked about. Leaving the office he recalled feeling panic, but then he had been happy. “The medication…”

“No, the medication? I’m not following you.” Madison said, happy to hear the panic that had been in Jacqueline’s voice was fading.

Pressing the palm of his hand to his forehead Jackson let out a long sigh. “I don’t know, maybe we talked about it, but I wouldn’t have…” His voice trailed off wondering what he actually had said. ‘What if I said yes thinking this was something far off I could just not do? Wait… I don’t have to do anything!’ Pressing his plumped lips together for half a heartbeat Jackson shook his head as it turned into a small smile. “Oh my god, I’m being silly.”

Blinking a few times before squinting he tried to inspect himself. ‘Silly? Where did that come from?’ He asked himself before continuing. “I don’t know why I’m panicking, I can just tell them no thanks, it isn’t like they can **** me to go under the knife.”

Hearing Jackie say how she was going to throw away the opportunity caused Madison to sit up on her bed. “Didn’t you tell me before the company helping you with the transition was all covered, as in this would be free for you?”

Feeling much better Jackson stepped away from the wall and looked once again over the rail and down to the first floor. “Yeah, and my boss was even going to donate extra paid days off for me to recover. Think I could use those days off even though I’m not getting the surgery?” He asked, chuckling to himself.

“Your boss did what?” Tilting her head back Madison tightly closed her eyes as she held the phone away from her ear, not paying attention to the reply as she did her best not to get angry that Jackie was going to throw all this away. She had seen a therapist and a doctor and she didn’t believe this would have been scheduled without both their and Jackie’s consent and now her foolish sibling was backing out because of nerves. She tried to tell herself it wasn’t Jackie’s fault and knew it was her job to once again push her brother, now sister, to where they needed to go. “I need you to think for a second, think what could happen, like worst case scenario if you turn this down.”

Madison figured the corporate assistance could be canceled, funding pulled and despite Jacqueline’s improved salary from being an intern losing thousands of dollars of free money would still be a massive impact. While on the other end of the phone Jackson said little. “Umm.” The feminized man looking down over the distance to the ground as his mind went to a further place than his sister. ‘They could fire me, finding out I’m not what they think and… oh geez that would also mean Linc. God he is off training for a job he never would get and that other girl… fuck I forgot about what Dunn had said about boyfriends.’ His thoughts went on all jumbled together, jumping from one subject to another, connecting things together that had nothing to do with one another. ‘How can not wanting tits be selfish? Fuck!’

Taking a deep breath Jackson could feel the restriction of the corset he wore, the pull of the bra straps and the movement of the large prosthetic breasts glued to his chest. “You know Maddy… sometimes I hate you.”

“Yeah well, sometimes I have to be the big sister or the bitch as I have heard you call me more than once.” She said with a big smile on her face, happy she had gotten through her sister's thick skull so they could get out of their own way. “If you are really upset I have a way to blow off some steam tonight, Callie ended up having to cover a shift at the bar and we were planning on going to a place that is doing jello wrestling. Jello, bikinis, little kiddy pool. Don’t you think doing that would be a way to have a little fun and forget about everything?”

The corset kept Jackson mostly straight backed, but standing there he stood up a little straighter, his eyes a light at the idea of going to watch some hot girls rolling around and fighting in jello. “Yeah, yeah… that sounds like a good time.” He agreed quickly before the corner of his mouth quirked up in a smirk. “But only if you're buying tonight.” He said wanting to get more out of his sister even though he had no real intention of imbibing any **** after the massive hangover he had to fight through today.

“I can promise to get the first round, you're pretty and all but not my type. I only liquor up people I plan to take home, or for them to take me home.” She said teasing.

A small laugh escaped Jackon’s lips. “I mean we will already be going home together.” The second the retort left his lips Jackson regretted it, he was trying to be playful not incestrous.

Madison was about to stand up, feeling the conversation coming to a close and get back to work, but found herself having to hold in a laugh of her own. “Can you imagine, Lincoln’s eyes would just bug out of his head if he was home.”

“Maddy… I was joking.” Jackson said in a somber tone, his smirk having fallen into a frown at the disgusting thought of benign with his own sister, he was aware she was a good looking woman, but the very idea was repulsive. At the same time he also knew she was right about Linc. ‘What guy wouldn’t want to have a threesome with two hot…’ He shook his head refusing to complete the thought of including himself in the category of girls, no matter what he looked like.

Yeah! I know, I’m not as ditzy as you. Remember I’m the smart sister, programmer while you are a secretary.”

She couldn’t see it, but Jackson still stuck his tongue out at his sister. “Administrative assistant and I think you mean junior programmer.” He corrected her.

While the Hart siblings spoke on the phone, back in the office Alexander Dunn came out of his office and found his assistant’s desk vacant. He glared at the phone that had blinking lights, indicating incoming calls. “Didn’t even log off the phone…” His voice trailed off as he looked about the area to see if he saw her about. Walking closer to the desk to do what she should have done when she left her desk he took notice that once again she had walked away from her desk without locking her computer, a habit he would have to break her of. Sitting down he clicked a few buttons on the phone and was about to get up when he noticed what was open on her screen.

“Oh!” He said happily seeing the email. Mary had spoken to him about it and he was happy for the sexy little thing to get a real chest for him to look at and play with, but that had been before the conversation with Downings in the parking garage. “Still though…” he pictured the fun he could potentially have. Imagining the bottle blonde throwing herself at him for getting her a nice pair of beautiful tits. With that in mind he checked her sent folder to see if she had replied and confirmed yet, seeing it not done, moved his hand to the mouse, sliding the cursor over to the reply all field. ‘Abandoned her desk after getting the good news, didn’t bother to log off or close a thing, girl must be off gossiping, giddy about her good fortune.’ Alexander thought to himself.