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Chapter 49
by
Nicegent42
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Scene 33
Let me know what you folks think of this chapter, I'm really not sure about it.
In the bathroom attached to the master bedroom Jackson leaned over the sink to be closer to the mirror as he slid the red creamy lipstick over his lips that promised a bold look as he hummed the beat to the song Uptown Girl. The feminized man felt like he was on top of the world, serotonin flowing thanks to his medication and what today was bringing he felt more than just a little happy. The accepting who he is, or who she was, advice that he had gotten was utter hogwash, but still he felt pleased with himself. Soon Linc would be home and that meant when they went into work together tomorrow it would not just be both of their first days back in the office, but it would also mean the first day that things could start getting back to normal. ‘Linc will take Dunn’s job and I can stop, or at least start the process of being me!’ Jackson thought.
Turning his head from left to right, double checking his makeup, Jackson watched the beautiful blonde in the mirror smile. The eye shadow, eyeliner and mascara made her soft brown eyes alluring while her bold red lipstick covered lips looked inviting. Jackson couldn’t help himself as he blew a kiss in the mirror before a bit of laughter bubbled up. “At least I make a pretty girl.” He said to himself as he turned around to get a look at his full body in the long mirror on the back of the bathroom door. The girl in the mirror still wasn’t wearing any jewelry or shoes, but the white linen dress with cap sleeves looked spectacular on Jacqueline. The sweetheart neckline came down just enough to see her cleavage, something he knew he could enhance with putting the right necklace on her. In the reflection he saw the girl’s smile grow as she looked herself over.
Despite his current happy mood Jackson hadn’t forgotten about his troubles, but there was nothing to be done at the moment. The surgeon said that he needed to wait three to five months to get rid of the breasts and he was just going to have to let the hormones run their course and imagined once Linc got him a job in the sales department that everyone would just see Jacqueline transitioning to being male. Not ideal, but that only mattered till he got the work experience and could get the heck away from the large corporation. For now though, he had to play his part and just let the sexy woman he saw in the mirror do what she needed to do in order to get through this.
After finishing the task of getting ready, adding a pendant necklace, earrings and a bracelet he slipped his feet into some five inch wedges and buckled them on. One last glance in the mirror before throwing open his bedroom door Jackson stepped out into the living room, ready to face the day. A day that for at least the first few hours meant sitting in the living room with his sister who was only wearing a t-shirt and a pair of panties, a shirt that didn’t do anything to cover her ass. Jackson watched her curiously for a second, as she sat on the couch with legs crisscrossed and work laptop in her lap as she worked. He didn’t like walking around in just boxers, but his sister, Maddy was so confident and comfortable with herself that she lounged around in practically nothing.
Looking up from her PC the corner of Madison’s lip tugged upwards as she took her sibling in. “Someone is looking nice. Wanting to make sure your boyfriend knows what he missed?”
Shifting his stance Jackson put both hands on his hips. “I will remind you dear sister of mine, that you are the one that picked out practically my entire wardrobe.”
Closing the lid on her laptop, what she was working on being discarded momentarily Madison looked her sister over once more, loving how they stood in such a feminine way and felt a bit of pride being able to help Jackson be the girl she saw standing there. “You are welcome, but it wasn’t me who decided to put on shoes, heeled shoes that make your legs and ass look amazing…” Madison drew out the word. “That was you, but I would remind you little sister about you saying how you loved Lincoln’s cock when we came back from the club the other week and it looks like you want to make sure you get its attention too when your brown eyed man comes home.”
Averting his eyes Jackson felt a blush come to his cheeks, he didn’t fully remember that night, but a foggy memory of saying something like that came to mind. He knew there was a circumstance for him to say the phrase, but he couldn’t recall and it mattered little considering he had said it. “Yeah well… I wasn’t going to walk around barefoot, I doubt you have vacuumed or mopped the floor while I was bedridden.
“Suuuure.” Madison watched Jacqueline shift, the healthy blush coming to their cheeks as she teased her sister. There was truth in what Jackie had said, she hadn’t cleaned the floors, they weren’t filthy or anything, but still she let the weak excuse for wearing the shoes inside slide. “I guess I should get dressed too, maybe I should put on something sexy for Lincoln, I mean we did talk about getting married once and a girl could do a lot worse than an up and coming executive.”
“Madison Nicole Hart, you have a girlfriend!” Jackson chided his sister. Jackson knew she was teasing, or at least he thought she was and he didn’t need her ruining his plans before Linc took over for Dunn.
The browned haired young woman laughed. “Don’t you fret little sister, I’m not going to steal your man.”
“He isn’t…” Jackson clenched his jaw for a second before huffing. “Don’t you have work to do or something?”
Getting up from the couch Madison stretched a little to pop her back. “God yes, we pushed an update that broke all the pointers to a location's print server and…” Madison pressed her lips together as she looked at her sibling. “It broke things, but that can wait till I have a shower and get changed. What are you going to get up to while you wait for your true love to come home?”
Ignoring what he perceived to be a barb, Jackson was about to answer when he realized he didn’t actually know what to do. Looking down at the floor he thought about what he had said to his sister before as an excuse for putting on his current footwear. Jackson wasn’t one for cleaning when he could avoid it, but he was in a good mood and had been mostly stationary since the surgery. “Maybe I will clean up a bit, don’t want to have Linc think my sister is okay living in a pigsty.”
Like her sibling Madison wasn’t the neatest person, while she hadn’t cleaned, she also hadn’t left a mess. “Well look at you wanting to show how much of a good little housewife you can be.” She teased, already making her way to her bedroom that once belonged to Jackson.
Jackson pinched his face in as he stuck her tongue out at Maddy, knowing that if he responded verbally she would then respond in kind, she always had to get the last word in from his experience. Watching her close the door to his old bedroom he thought on her comment about being a good housewife. The thought felt distasteful and yet a soft laugh escaped Jackson’s lips. ‘I am about to be engaged for this ruse to come to a close.’ Moving over to the closet where the washer and dry lived the feminized man pulled out the vacuum cleaning. “Mrs. Jacqueline Hatch. Can you even imagine?” Jackson laughed again as he spoke to himself.
Busying himself, Jackson went about the late morning cleaning the apartment, still in a great mood and easily lost in thought thanks to the chemical concoction running through his system. His sister after actually getting ready for the day had taken her laptop back into her room to avoid the noise, leaving the feminized man to himself as he went from vacuuming then to other chores, zoning out and losing track of what he was doing more than once. The small living space didn’t look much different, but Jackson knew it was cleaner and a small sense of accomplishment filled him. It wasn’t until then that he checked his phone for messages. All the built up text messages and voicemails from when he was wallowing had been answered, or at least answered enough far as he was concerned. So the awaiting message from Linc waiting for Jackson, made him smile.
Lincoln: Getting on my connecting flight now, can’t wait to see that gorgeous smile of yours!
Lincoln: Make sure you are wearing something nice because when I get home we are going out for a memorable date.
Biting the long nail on his index finger gently, the corners of Jackson’s lips rose in a soft smile as he read the message. Lincoln coming home was absolutely a reason to celebrate, that meant all of this… uncontrolled life was coming to a close or at least moving to its last chapter. “Now what would Jacqueline wear for a date when her boyfriend had been out of town?” Jackson asked himself before moving off to the bedroom, a few ideas coming to mind.
Stripping off the outfit he had put on for the day, Jackson clapped his hands, his plump lips pressed together as he looked himself over in the mirror, enjoying the view. Getting dressed up to look sexy for his friend wasn’t ideal, but Jackson didn’t know what was planned. Lincoln could be having them go somewhere that coworkers would see them and Linc hadn’t seen him since the surgery. The pressed lips changed into a sly smile as Jackson imagined teasing his friend as he played up the part of the devoted girlfriend for what he hoped was one of the last times. “Linc has no idea what I have done for him.”
Without his consent Jackson’s mouth started to water as the memory of Dunn’s member slid in and out of his mouth and a phantom taste of cum came forth. ‘Do I have to do something with Linc now that he is home?’ Jackson asked himself. “I hope not, but if I have learned anything… it is disgusting but at least I know it won’t kill me.” Just thinking about that made Jackson feel uneasy and knew he shouldn’t be feeling so happy, but even dower thoughts had no hold on his current mood, but it did feel much more like Jacqueline’s world than his own.
“Lincoln’s home, this is not good, it is great news! I just have to be Jacqueline for…” Jackson shook his head, knowing damn well it wasn’t going to be like turning on and off a light bulb. “Don’t think about that, think about tonight. Think about what Jacqueline would do, what would she do?” Asking himself the question Jackson looked back into the mirror before unclasping the bra that held his new breasts. “What would she do? Look her best, flirt and tease… okay, okay. Jacqueline, Jacqueline Hart. I am Jacqueline and I know exactly what I’m going to do!” Even with all the medication running through his system Jackson could feel the stress start to build, it couldn’t get to panic levels, but as he said the name of the air headed secretary that he had been pretending to be something felt like it slid into place and the stress she was feeling practically melted away before it was forgotten.
Feeling excited Jacqueline changed her panties, sliding up a satin black thong, its very caress on her privates sending a shiver up her spine. She would get to tucking her little secret between her legs in a bit and she had a lot to do and wasn’t exactly how long she had to get ready. Wanting to look that little bit extra feminine she got out a simple black corset, the shareware hadn’t been comfortable at first when she first started to wear things like it, but it had grown on her. The compression and support felt comforting, and what it did for her waist felt like a bit like witchcraft. She combined that with a dark red floral patterned balconette push up bra over black transparent fabric.
She felt something much more masculine stir in her, but ignored it. Biting her bottom lip she thought about what to do with her hair, but with a cloudy mind she found herself distracted and had moved on to thinking about other things for the night. Like how Lincoln loved playing with her fake breasts and wondered how it would feel to have his warm hands on her chest. The thought felt a little wrong, but she had done so much more in the office to protect Lincoln. Wouldn’t it be wrong to deny him the same pleasures she gave their boss in his name?
Soon enough she had herself tucked away, her hair in place with a nighttime look to her makeup. Jacqueline’s eyelashes were feathered out with mascara, she had eyeliner on and a deep blue sparkly eyeshadow that made her wonder if that would be enough to keep their friend’s focus away from her chest. With hair and makeup done and the rest of the outfit laid out what stress had driven the mental deviation slowly subsided. Jackson looked himself over in the mirror and liked what he saw and knew his friend would too. It was wrong, but also a bit fun.
The mental hand off wasn’t something the feminized man took note of, it wasn’t like he wasn’t in control of his body, it just felt like being a girl was okay, Jacqueline had a purpose and it was like a costume. Something an actor might do, but even as it made some tasks easier to digest it wasn’t something that could last. Right now he saw himself in a little black dress that stopped shy of mid-thigh, that showed a good deal of cleavage without being what he considered trashy. The dress had a semi top that went with it, it left the breast area of the dress open, but covered his arms with both opaque and translucent black striped material that buttoned at his neck. In his ears were gold and sapphire, or sapphire like costume gems that hung down in three tiers of teardrops. Around his right wrist he slipped on a gold bangle that alternated with square cut diamond and sapphires, it like the earrings looked expensive, but were far from it.
The last thing Jackson needed was to slip his feet into the six-inch, sling back, peep toe heels that had a small platform to make the height of the heel easier to manage. They were higher heels than he ever wanted to wear and wasn’t sure exactly why he had picked them out. Slipping them on he couldn’t deny the effect they had on Jacqueline. The girl, the woman, the very sexy woman he saw in the mirror looked incredible. Giving himself a wink and blowing a little kiss he watched Jacqueline do the same back and felt his heart flutter. “Mr. Hatch isn’t going to know what hit him.” The idea of a small prank coming to his clouded mind, about wondering how uncomfortable he could make Linc by just doing what would come naturally to Jacqueline.

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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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