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Chapter 39 by Nicegent42
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Scene 23
The car pulled up in front of the Florida Mega Corp office, Lincoln moved his right arm so it rested on the back of the passenger seat as he looked at Jackson… Jacqueline who already looked to be having a bad day. They looked incredible or at least incredibly hot, but even with the changes to their face from makeup he had seen that look on his friend’s face many times before. Jacqueline wanted to go home, and the day hadn’t even started. “Drinking a bunch on a work night doesn’t seem like such a good idea now does it?” He asked, raising an eyebrow.
Letting out a long breath of air Jackson looked down at his feet, today he wore a pair of heels, as always, these were black hidden platform lace up six inch stiletto ankle booties. They were truly a pain to be in, let alone walk in, but Jacqueline was the type of girl that put beauty over comfort or some other horseshit. His suntan colored five denier pantyhose covered legs would help keep him from freezing in the office, though he imagined not by a lot considering he was sure hardly anyone could tell he was wearing them unless they were up close. His legs disappeared up into a white pencil skirt with a black striped line plaid style that had a small amount of blue in it and then he had on a tight black women's turtleneck shirt. No one could see the feminine underwear he wore underneath, the bra that pulled on his shoulders or the corset that pinched his body in. Jackson shook his head, not just at his friends' comments, those he actually agreed with.

The problem was that because of all these problems in his life right now he was having to get up an hour earlier than he normally would have and even back then he hated getting up early for work. He had to make sure he was clean shaven, not just his face… smooth legs on a woman were sexy, on him… just another burden. It took time to put on makeup, time to make sure the right jewelry was worn with an outfit. It was all a massive pain in the butt and nothing in his closet was really conservative, he had seen plenty of women wear frumpy outfits, but everything he had was designed to attract the eye. Jackson had chosen the turtleneck for the same reason he had chosen the skirt, they both covered more skin than his other options and still it looked… he looked… sexy. The night before he had been with Abe, the food had been a wonderful change from diet shakes and the wine just kept flowing. Before waking up in the morning on the couch the last thing he remembered clearly or semi-clearly was the glasses wearing man telling him about his family, about having two moms or something like that. “No… it wasn’t, not one bit.” Jackson admitted out loud while silently condemning himself from doing so when he was taking his pills. This morning he hadn’t taken any and wasn’t currently planning on taking them… or at least that had been his plan before he considered what Dunn was going to have him do.
“Well at least you admit it, knowing being part of the battle and all that.” Lincoln said, giving his friend a smirk.
Without turning his head Jackson gave Linc the side eye. “Recovering from a hangover or not, at least I’m not a nerd.”
“Guilty as charged, but considering the dating and future plans, I think the beautiful Ms. Hart likes that about me.”
At that comment Jackson did turn to look at his friend, while his hand moved to rest on the door handle, while he raised one of his perfectly arched eyebrows. “You don’t know Maddy at all if you think that. She may be a programmer or junior programmer but she thinks everyone else but her… in the field are dweebs.” At the word dweeb Jackson pointed one of his red painted nailed fingers in Linc’s direction, he wasn’t a programmer, but he made up for it with his interests.
“Haha, you know I’m talking about you Jacqueline.” Lincoln said, wishing she wouldn’t deflect like that when he was giving her a compliment. His friend turned girlfriend was more than a pretty face, but she did seem to have a problem admitting it. “Now I need to get off to the airport to start my real executive training, and you need to get to work.” With that Lincoln leaned closer pressing his own lips to her own. When his friend had first had his lips done, making them bigger and doing whatever lip flip thing she had complained about, but kissing her lipstick covered lips, they felt perfect. “You try to have a good day, I will text you when I land and call you when I get to the hotel.”
“Umm…” Jackson said, blinking a few times as he looked at Linc through the curtain that was his mascara covered lashes. It wasn’t close to the first time they had kissed and this one was pretty chaste, but he hadn’t expected it. He was just giving his friend shit and was expecting a verbal volley a lot more than a kiss. “Yeah, umm. Safe travels.”
With one hand hovering over his own jaw, one finger lightly touching his bottom lip, Jackson was mostly absorbed mentally in the fact that Linc had just so casually kissed him and he had returned the quick kiss on reflex he got out of the vehicle, though Jackson had to put his other hand out to catch his balance. Looking down he could see he had caught the heel of one of his uncomfortable shoes on a piece of uneven sidewalk. The sway of his body and feeling of almost falling didn’t play well with his headache, but neither did the morning sun.
So with a sheepish glance to Linc he waved him off, wishing that he was joining his friend on the trip instead of having to go upstairs and face their boss. Turning from the road Jackson started to head to the building, seeing his own reflection in the mirrored glass. He knew it was himself, but all he could see was someone he would have loved to chat up, or at the very least enjoy watching walk by. The blonde woman in the reflection walked with a sway to her hips, and a jiggle to her chest all accompanied by the click clack of her heels on the concrete. A sound that Jackson had been trained to hear so he could be on the lookout for a pretty gal, but now it came from him and was accompanied by too many other feelings to still be positive. Putting one hand on the door to the building he looked down at his long red fingernails that made his hand look so feminine and the pearl bracelet before closing his eyes for a second. ‘It is just another day, Linc is off and when he comes back things will be different. Only two more weeks of this, just two more weeks of being Jacqueline, two more weeks of pretending to be a girl, you can do this… I can do this. I have to do this.’ Jackson repeated to himself before opening his eyes and plastering on a smile to himself before pulling the door open.
Walking into the building Jackson gave a small wave of his hand to Lilian, the pretty and overly friendly girl behind the reception desk. He was ready to just walk past her, but his head was still pounding and girls tended to keep things like aspirin in their purses. ‘Guess I could start carrying some with me too.’ He thought to himself as he corrected his course.
“Well good morning and hello to you. Lilian said, smiling at her work friend as she continued to type on the keyboard while looking away from the screen.
“Yep, a good morning. I mean… a good morning to you too Lil.” Jackson said, trying to brighten his smile to match the one being given to him. He knew she wasn’t flirting or even interested in him, but still having Lilian’s full attention on him while she smiled still caused his pulse to pick up. “Listen Lil, I was hoping you…”
“I just love your tartan skirt, you look so good in it. I hate that you are a skinny bitch sometimes. I had a donut for breakfast and seeing you makes me feel like a cow.” Lilian said, putting one hand on her stomach. “Not your fault, but… I’m sorry, what were you saying?
Mouth still slightly open Jackson stopped talking for a second after the girl spoke over him. “I was…” He stopped again to really process what she had said, it was nonsense. Lilian was a tiny thing, never would he call her fat or ever hint at it. Sure she wasn’t the type of girl he would want to tell them that they should go eat a sandwich like a model who ate ice for a meal, but they weren’t healthy. Lilian looked like she took good care of herself, better than him… if he had hit the gym like Linc had been recently then no way could he look like this. “Lil you are not fat, by any definition. Honestly, you're hot.”
“You are just saying that.” Lilian said with a wave of her hand. “But, feel free to continue or mention it to any successful good looking bachelors.” She added with a tittering laugh.
Mirroring the sitting girl, Jackson put one hand to his stomach feeling the corset under the blouse. “Besides, I thought I already told you that I have a little help here.” Jackson said pushing forward and not dwelling on the fact the pretty girl wanted him to introduce her to other men.
“Hmmm, guess we all have our issues.” Lilian said with a shrug of her shoulders. Glancing over at her screen her eyes opened wide as they darted back to Jacqueline. “I’m sorry you were saying something.”
Doing his best to hold back his displeasure Jackson gave the attractive woman a partial smile. ‘Just keep smiling, she thinks your female, she isn’t trying to make you feel bad. I’m Jacqueline Hart… I’m Jacqueline Hart. Of course she isn’t interested in me… god I wish she was though.’ Thoughts walking past Lilian the receptionist every day completely invisible to her back before he had been tricked and then **** into wearing high heels to the office came to mind. ‘When this is all over I wont be just some little intern, I will be able to afford to take Lil out on a date.’ Jackson nodded his head slightly to himself, making a promise that he would ask the girl out the second he back to wearing boxers instead of the lacy panties. “I… I had a rough night, I was wondering if you had any aspirin?”
“Awww, I’m sorry to hear that.” Lilian took note of Jackie holding her stomach and her friend wearing the corset made more sense. Figuring the compression was helping with her cramps. “I got just the thing.” She said pulling her purse out from a desk drawer before going through it to take out a few pills from a Midol bottle.
While the perky girl was busy Jackson watched the different people coming into the building to start their day. Most people were too self absorbed and in a hurry to get to work to notice someone watching them all and Jackson wasn’t above taking the opportunity to check out any visually appealing female, but this morning his eyes tracked the men. They all wore pants, while he wore a plaid… or tartan skirt as Lil had put it. None of them had to wear heels, he loved hearing and seeing women in them, many of his own porno searches had used heels as a key word, but now he had a new appreciation for the footwear.
“Here you go, hope this helps you feel better.” Lilian said, taking note of how Jackie was eyeing up some of the men that came into the building, her eyes not moving up past waist level. At times when she was on her period she had felt more horny than normal, so she had an appreciation for what Jackie was going through.
Taking the pills and dry swallowing them without bothering to look at the aspirin she handed him, Jackson gave her another **** smile. “I hope so too, talk to you later Lil, I have to get upstairs.”
Moving past the reception desk, badging in and heading upstairs by the elevator Jackson once again looked at his reflection, thinking how odd his life was. It wasn’t even eight in the morning and he had been kissed by his best friend, and called a skinny bitch by a woman he very much wanted to ask out on a date, while she wanted him to introduce her to eligible bachelors. It was a truly odd day and things seemed to just be getting started. The end was in sight, Linc going away for management training put a real clock on everything, soon, but not soon enough all of this will just be something he talked about to a shrink or drank to forget. Jackson could see his own nose crinkle at the day of ****. The pounding in his head was no where near as bad as when he woke up, but it was still present enough to remind him that cutting back was a good idea. He just had to get through today… one day at a time, one day at a time. ‘I’m a man in a dress… well a skirt, I have a boyfriend and soon to be fiance and everyone I want to bed only sees me as a friend or competitor. I really need to see a therapist.’ He thought, adding ‘Shit… I should have had Linc stop off to get a travel size mouthwash.’ When he saw a bearded man checking him out in the reflection, his beard reminded Jackson of Dunn.
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Diversity Hire
Mega Corp Florida
Two interns at Mega Corp got to know one another becoming good friends and roommate and after a year as interns, they had all but given up on being hired. When one of them pranks the other about a turnabout day to be dressed as the opposite gender things go out of control. Jackson gets up getting hired on full time as Jacqueline as the company's newest diversity hire.
Updated on Dec 23, 2023
by Nicegent42
Created on Aug 21, 2022
by Nicegent42
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