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Chapter 16
by Nicegent42
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Scene 16
With the changes to his chest and lips and the come fuck me pumps he was wearing Jackson wasn’t surprised that he garnered extra attention. Lilian had flagged him over, this time Lincoln joining him as he spoke to the girl. “Oh my god, you look incredible.” She said with a huge smile, standing at her desk, reaching over to give a hug. “And must be Lincoln, I have heard only good things about you and for your sake it needs to stay that way.”
Lincoln chuckled, rubbing the back of his neck, a nervous habit. “I can’t control what you hear, but I can promise my only goal is to keep Jacquline happy.” Lilian gave him a serious look for a second, it breaking away quickly after.
“A good goal. I’m Lilian, most people call me Lil.” She said, extending her hand to him.
“Happy to finally officially meet you, I have seen you almost every day coming to work and never worked up the nerve to come talk with you.” Lilian turned her head to her new friend, giving her a smile before looking back towards him.
“Everything worked out for a reason, ya know I always thought you were so cute and a bit of a rebel coming in here wearing sneakers. If you did come talk to me I might have seen if you wanted to go out for drinks, but look at you now. Dating Jacqueline and keeping her happy and by the looks of her today, she knows how to keep you happy too.” Both Lincoln and Jackson started to blush at her insinuation.
“I love the way she looks, but she looks this way because she wants to and I’m happy to support her.” Jackson eyed his friend, it wasn’t like he could say he was wrong, that no all of this was because his sister made him or had talked him into it and that only happened because he had tricked him into coming into the office in heels to begin with.
“Aww, the two of you are so cute together. Now list, Jackie knows I could talk both of your ears off all day and I don’t want to get started. So I’m going to let the two of you go and maybe see about updating my dating profile so I can find someone as good for me as what the two of you found.”
Walking away Lincoln looked back over his shoulder to the talkative girl. “Hear that? I have a shot with Lilian, how many times did you talk about how hot she was.” Jackson elbowed him in the ribs.
“You are dating me, we are in love and make each other very happy. Remember!?” He said through clenched teeth and a fake smile.
“Oof. I remember. So happy.” Lincoln rubbed his side. “So in love.” Note to self, Jacquleine gets jealous, Lincoln thought. While Jackson internally grimmanced at his friend’s slip up, hoping no one heard him. He had his beard, and had done something to keep it that way that he would never forget, the dick needed to remember that. Especially as he looked now and how many men’s eyes he could feel following him. It didn’t help that the high heels announced his presence and the jiggle of his breasts practically called out for their attention.
Jackson wasn’t so lucky for Dunn to be out of the office two days in a row, so off he went to get the man his coffee and just like everyday so far he ran into one of the office gossip, Tabitha. “Morning Tab.” The shorter woman stopped in her tracks looking directly at his enlarged chest and then up to his face. She tapped her bottom lip, not making eye contact but looking at his new lips.
“Something feels different about you, but I just can’t put my finger on it.” Tabitha squinted at her office friend, before pointing down at the girl's sexy shoes that looked much like her own nude pair she had on. “I know, you got a new pair of shoes.”
Grimacing, Jackson nodded, knowing she wasn't so brain dead that she didn’t see the obvious.”Just had a little work done, ya know wanting to look my best.” Jackson let out a practiced giggle, hoping she would let it go.
“The boob fairy pay you a surprise visit?” Jackson was surprised she actually pressed her finger into one of his fake breasts. He really didn’t have an excuse as to why he was suddenly larger and hadn’t even considered needing one, but he really wished he had to discuss options with his sister.
“They are umm fake, you know, trying things out to see how I would look.” He stepped closer to the coffee machine, wanting to get what he came for and get away. Already knowing the latest piece of gossip was now going to be about him.
“Oh, I get it. Using some forms before you go under the knife. Well I have to say you look incredible, I think you chose the right size. It suits you.”
“Awww, thank you!” He said with as much fake joy as he could imagine at the compliment that felt like she had punched his male ego right in the nuts. “You know I would love to stay and chat, but Dunn wants his coffee.”
“I’m sure he will want more than that from you, nothing you haven’t done for Abe or your man Lincoln.” Jackson was ready to leave the break room when he stopped to turn and look at the girl. She had known what he did with Lincoln or at least thought she did and was including Aberaham in the same category.
“Tab, I didn’t do anything and please you can’t go around telling anyone that.” Jackson spoke in a quick whisper as he stepped closer to the pretty woman, hoping and wishing she hadn’t spread that rumor or worse, someone had told it to her.
“Sweetheart, you have nothing to worry about, I’m not going to spread any nasty rumors about my friend.”
“Thank god.” Jackson felt a bit of relief come over him.
“Well so long as you tell me the details, how do the two compare?”
“Tab I told you, nothing happened…” Tabitha shook her head, knowing for a fact she saw Jacqueline drag her boyfriend over to the supply room and then later her and Abe coming out of the men’s room together.
“No, none of that denial. I know what I know girl, so later today we can discuss it over lunch. Maybe we can take it early and still get some mimosas, we can’t take advantage of them being endless, but we can’t have it all.” He felt like he was painted into a corner, he wasn’t sure if she was threatening him with spreading the rumor if he didn’t tell her the details of his encounter with Lincoln and Abe even though nothing happened or if she was just trying to be nosey but he really couldn’t afford a rumor like he has been sleeping around the office. Feeling stuck he decided he would just have to make things up and hope she bought it.
“Well okay, but you know I can’t tell you everything. At least not unless you tell me about your own experiences.” Jackson thought if he had to tell her a story, maybe he could at least get the hot woman to tell him about her own escapades, give him something to think about the next time he jerked off. It would have to do, it wasn't like he could actually sleep with her.
Leaving her with his pyrrhic victory, Jackson went into his boss's office with a hot beverage in hand. “Shut the door, dear.” Jackson did as he was told, coming over to put the mug on his desk, expecting him to react to the way he looked and then maybe be told off for screwing up the day before on something or even for taking a long lunch.
Alexander looked over his secretary, whatever she was using to fake having breasts was impressive, the way they moved made them seem real and made him want to hold her from behind and squeeze them between his fingers. The way she looked now was a far cry from the lazy intern he had seen from time to time. Today Jacqueline looked like sex on legs to him and there was one of his problems. He was able to push past his prejudices, mostly because she didn’t look like a man in a dress, but she also said she had a boyfriend and was loyal to him. When he saw his schedule today he noticed she had put her boyfriend Lincoln Hatch on calendar to discuss his future. That man could be the answer to a few of his problems. “Come here we need to talk.” He said pushing his seat back from his desk, patting his leg.
“Sir…”
“I won't bite, come sit. I’m not asking.” Jackson swallowed hard, mincing carefully around the desk, stopping just short of him.
“Mr Dunn, I don’t think…”
“Girl, I told you to sit. I’m not paying you to try and think. I pay you to look pretty out front for me and do what you're told. Now, do what you're told.” Fuck, fuck, fuck, fuck, Jackson though as he sat down across the older man’s leg. Immediately he felt his rough hand land on his thigh.
“See that isn’t so bad, now.” Alexander gently gripped the girl's chin between his thumb and index finger, turning her face to look him in the eye. “I wanted to say you look lovely today.”
“Th… thank you.” Jackson felt so nervous, starting to think about what Tab had said about his boss wanting things. Any thoughts of what he would normally do didn’t even try to make it into his mind, he just sat there feeling small and ****.
“I see that I have a meeting with your boyfriend today and I wanted to hear what your opinion was about him.” Feeling one hand wrap around his waist and the one that grip his chin fall back down to his leg Jackson’s nerves were going crazy telling him of the danger of letting a man touch him like this, no man should touch him like this.
“I love him.” The first thought that came to his mind for an answer was the story, they were in love, he needed to remind Dunn that they were in love and that meant nothing could happen between them. It shouldn’t even need an excuse to not want to be touched, but even this one felt like a sheet of paper trying to stop a bullet at the second as he sat in the man’s lap.
Rolling his eyes Alexander let out a sigh at the bimbo’s reply. “Yes, I know, but how is his work ethic? Does he fuck around here in the office and then stress himself out to meet a deadline? Does he let people push him around or is he reliable and sturdy?” The questions seemed earnest to Jackson, like the man wanted his opinion on if Lincoln should be hired on, but he also thought he should already know these answers.
“He is a good employee sir, doesn’t mess around and umm….” Jackson hesitated for a second, but the man already knew this so continued. “You have told him to focus on some reports and work on nothing else and then Linc… Lincoln told people he couldn’t do the work they wanted to assign him and you yelled at him for not listening to them and talking back.”
“Did I do that? Sounds unfair. I try to be fair, do you think I’m fair Jacqueline?” Jackson again swallowed hard, the man always intimidated him a little. More than once he had told Lincoln that he was going to march into his office and talk him into hiring them, but he just never could work up the nerve.
“You are very fair sir.”
“Well I have a problem. I want to be fair to him, but I don’t really have any positions open that he would be a good fit for and if I put him in something he wasn’t a good fit for it could impact the department or even a whole division and now that HR knows he has been kept as an intern for so long he can’t stay there.”
Suddenly Jackson felt afraid for his friend and guilty. Sure, him coming to the office dressed as a girl was started by him as a prank, but he of all people couldn’t hold a prank against someone. Lincoln still being an intern and that coming to light was his fault though. He didn’t have to push Dunn to do something, he just wanted to help and it was blowing up in his face. “Please don’t fire him! He loves numbers and things like that, I’m sure you could find something in accounting for him.”
Pretending to think about it, Dunn tapped his hand on the girl's leg, sliding it down to feel the nylons on her leg. “Can I be honest with you?” Jackson nodded his head nervously.
“I have been angling to move up the chain and hiring someone like you ended up putting a feather in my cap so it could actually happen. You see my boss, Tripp Salizar… who names their kid Tripp? Well he is retiring soon, nothing announced yet and suddenly I’m the front runner for his position.” That sounded like great news to Jackson, but the way he brought it up sounded odd and he wasn’t sure how this connected with Lincoln.
“That is good news, congratulations!” He made sure to sound upbeat and perky, doing his best to imitate the inflections Lil often used.
“It is, and it isn’t, but that doesn’t concern you. I might and I mean I might have a place for Mr. Hitch.”
“Umm Hatch sir.” Jackson corrected as he tried to push the man’s hand away from feeling up his leg.
“Yes, well honestly it would be easier for me to just let him go, but I also don’t wish to upset you my dear. So I have something I would like you to do, to help me stay in a charitable mood.” Jackson swallowed hard again, shaking his head from left to right in tiny movements. His fears not just coming true, but being worse. The man wanted him sexually and was going to use his friend’s job as leverage. Jackson’s brain went into overdrive trying to think what to do. Should he give another blow job to save his friend’s job? He was dressed like some bimbo secretary, but he was still a man and men don’t do that sort of thing, but could he live with himself knowing his friend was fired because of him?
“What if I went to HR and told them, they wouldn’t be okay with this.” Dunn shook his head, holding the girl tighter to him.
“I would imagine they would think you were making up stories to save your boyfriend.”
“Sir… I can’t give you a blow job, please!” Dunn tilted his head to the side, letting go of the girl in his lap.
Miss Hart, I wasn’t going to ask you to do that or to have sex with you.” Jackson blinked his long mascara-covered lashes a few times, not moving from the man’s lap even though the hand around his waist no longer held him in place.
“You don’t want me to give you a blow job?” The relief he felt was almost palpable, but at the same time Jackson felt a small bit of anger along with confusion. The way he looked now and how Dunn had him on his lap and the comments he had made before and slapping his ass, how could he not want that? It felt like an insult, and that feeling only caused Jackson to feel more confused.
“If you want to blow me, I won't be turning that down, but you have made it clear how loyal you are to your man. So instead you will do everything but… sexual please me. Teasing me will definitely turn me on, but it will also make me feel good that you want me if you were free.”
“What? Umm so I tease you and you don’t fire Lincoln?”
“Exactly or at least, I will do my best and you will do your best to make sure I keep a smile on my face. Sit down in my lap when you come into my office, drop things in front of me and then turn around, bend at the waist as you slowly pick it up. Flash me your stocking tops and things like that.” Alexander wasn’t sure where the idea came from, but he did have a reputation in the office. He had seen some of the guys get hassled when they were in the locker room after playing racket ball about not being able to close the deal. Few people knew Jacqueline was transgendered, so they would just know the girl was openly flirting with him and spending time in his office often. It would be enough to not lose any credibility and who knows, down the line her acting like towards him all the time might make her want to act on her desires more.
Jackson didn’t move for a bit, but when the hand holding him in his boss’s lap didn’t return, he slowly got up, waiting for an objection that didn’t come. “I just flirt with you and that is it?” Seeing Dunn nod he held out his hand to shake and seal the deal. “You do your best to keep Lincoln employed and… gainfully employed and I flirt with you.” The left side of Jackson’s pursed lips tugged up as he fought back the smile. Just flirting meant that he no longer had to worry about his boss insisting upon physical gratification like he had been fearing and doing his best to avoid. The best part was he was actually going to help his friend and in doing so help himself.
“You have a deal, Miss Hart.” After shaking his boss’s hand, Jackson turned to leave, proud of himself when he felt a slap to his ass. “Ohh!” He looked over his shoulder surprised, remembering the deal he just struck. Still looking at the disgusting man Jackson tried his best to give him a sultry smile, bending forward a little and sticking his ass out for the man to see. He pivoted his hips slightly to shake his rear in the older man’s direction. “I’m glad you like what you see.” He added a tittering giggle at the end before mincing out of the office. Slightly horrified at how easy that was, but still proud that the meeting went from this man wanting me to get on my knees and blow him, to I have to act flirty.
It was later that morning when Lincoln came up to his desk. Jackson held up one finger to keep his friend from talking and interrupt his train of thought as he finished typing up the memo Dunn had asked him to send. Finishing quickly, Jackson knew he would need to go back and proofread it, his typing skills weren’t exactly perfect with the nails, but he was getting better and faster. “Hey there handsome.”
“Hey there yourself gorgeous.” Lincoln couldn’t help smiling back when Jacqueline smiled up at him, he was sure just seeing it was causing his heart to beat a little faster. “I believe someone got me an appointment with the boss man. Any advice before I go in?”
Jackson thought how soul crushing it would be with how happy his friend was at that second if he walked in there and was told that today would be his last day. Instead, he would get to continue on, continue on in this soulless company, but still continue on to earn a paycheck. “Just be yourself.”
“Difficult, I was planning on being two other people.” Lincoln nodded to himself pretending to be serious. It was just Monday that he was telling Jackson to be more serious and focus on work and now here she was actively stopping him from interrupting her while she finished something. This week had seen a lot of changes, confusing changes for his mind, how he thought of himself. All of that being brought into question by his attraction to his friend, he was happy with where things ended up and the path they were taking together. “Just be myself, just so simple. You're a genius.” Stepping around the desk Lincoln kissed her on the cheek before walking up to the door and knocking.
Going inside when he heard the deep baritone voice of Mr. Dunn, Lincoln shut the door behind him. He had never actually been in the man’s office before, when the internship started someone else was in charge of the interns, but when the program ended, they were no longer around, leaving himself and Jackson in the limbo of working under Dunn as interns even though the program was over. “Good to see you, please have a seat.” Alexander stood from his seat, motioning with his hand to one of the chairs in front of his dark wood desk.
“I don’t want to beat around the bush too much Mr. Hatch. You have worked here for a while, I don’t hear much about you, good or bad. Though Miss Hart speaks very highly of you. One of the issues I’m having is I can’t keep you as an intern any longer, it was an oversight on my part that it has gone on as long as it has.”
“Oh.” The good mood Lincoln was feeling faded, in its place was dread. He could get by with unemployment, it helped that now Jacqueline made more money and they had an extra roommate, but he wasn’t sure where to go when you are fired from an internship.
“I have a few other problems and I was thinking that perhaps you could help me get rid of one, while I solve this employment issue for you.” Lincoln nodded along, hoping that this was all a preamble to him actually being hired on in one of the departments. You see, I wont be in this position much longer, or at least that is the plan on paper at the moment. Things might change, but if that goes through, you have an opportunity.” Dunn paused to see if the young man across from him would ask any questions, but when he didn’t, he continued on.
“Everyone, and I mean everyone that would come in behind me to fill my spot are either a shark that I will have to spend a lot of time managing to keep them from stabbing me in the back or they are a sycophant for someone who will. I could push for an outside hire, but I might not get control over who the company actually hires. That leads me to you, Lincoln Hatch.”
“Me sir?” Lincoln could feel a bead of sweat coming down his forehead. What the man was saying made it sound like he wanted him to take over for him and that was insane, he was ready to be a junior in some department, not even a middle manager and yet this man wanted him to skip all that, skip even being a department head, to take over his spot as a division president? Heck, he didn’t even want to go into management at all.
“I’m prepared to offer you this job, the one I hold now under a few conditions. I’m told I put you through the ringer when you told people you wouldn’t do their work when you were just following my instructions.” Lincoln opened his mouth to confirm that happened, but Dunn didn’t pause long enough for him to say anything. “What I want is my own sycophant, do you think you could be a yes man for me Hatch?”
“You want me to just agree with you and do what you say?” It was really something everyone already did, or at least openly.
“I want to put you in this seat and for you to report what happens and for me to give you marching orders and then report back to me anyone that comes knocking with plans of their own and they will come knocking. Does that sound like something you could do son? Get paid enough to have a bank account and a secret bank account that your girl doesn’t know about and all you have to do is do what I say?”
“I’m umm I just wanted to go into accounting sir.”
“There will be plenty of accounting Hatch, adding up all the people who will not speak negatively about me where I can hear it. You see I don’t want to move up the ladder to find out the snakes come out to play where I can no longer watch them. So how about it son, would you want to be in charge here?”
Wiping his palms on his pants with how sweaty they were, Lincoln felt out of sorts. “If the offer is real, then yes. Where do I sign?”
Leaning forward on his desk Alexander looked at the man in front of him with a hard look. “It is not that simple, first Tripp Salizar has to announce his retirement and then we have to have internal and external interviews for his position. Really all of that will be done quickly once he announces, but as I’m vetted for the position, I will have to offer up a suggestion and work on the process for my open seat. I can tell you the powers that be like to see stability, you know stability.” Dunn held up his left hand, tapping the gold band around his ring finger. “Me putting you forward for the position isn’t a guarantee you will get it. So you will need to make yourself look like a good option for them.”
“You... you… want me to get married!?” Getting married, he had thought about that in concept, yeah he wanted to get married he wanted kids, but no real consideration for it beyond telling his parents and grandparents he will settle down when he finds the right person.
“At least engaged son, that will show people you are serious. I can also enroll you in a few management training courses. Two of them can be done here, one is just online and the other is honestly a waste of time, but you get a nice Mega Corp management training certification. Then we can fly you out to a bigger office for a week to finalize you are on that track.”
“Sir…” Lincoln was not often the assertive type, he wasn’t really a leader, he never was, but right now an opportunity like no other was just presented to him. “Even with all of that, I’m still not qualified.”
“Please, mostly in this life it is who you know, not what you know and right now you know me.” Dunn waved his rebuttal away, leaning back in his seat.
“I can’t just umm, I can’t just go and ask Jacqueline to marry me out of the blue like this.” In his mind he saw tons of scenarios of her laughing at him, turning him and just flat out saying he was insane. They weren’t really in love, that was just some story. Sure they liked being with one another and the sexual chemistry was suprisingly good, but it had only been a few days!
“Hatch, I don’t care if you get engaged to her or someone else, no one is going to look too close at all of that. Unless you bring her along to a work function where she talks to other wives. You just have to tell me now if this is something I should go forward with. If so, you will start training on Monday and I have to give you a bump in pay, I can’t let someone see someone that is supposed to be my protege with an intern's salary. Then you have a few weeks to get you and Miss Hart or whoever settled in wearing a little ring around her finger saying you plan to get married. Though, keep in mind you will have to get married, the engagement will just buy you more time.”
“Yeah, yeah more time. Umm, how much are we talking about for salary?”
“In training? Say eighty, but once you take my position more and more over time assuming you can play the role I need you for.” The amount of money he was talking about felt staggering to Lincoln, he was only making twenty three thousand a year as an intern and after being out of college for over a year now the loans were going to start coming due.
“Eighty thousand a year?!” Lincoln’s voice felt shaky to him.
“To start.” Dunn said firmly.
“Yeah, yeah I will do it!” Lincoln stood from his seat, leaning over to shake the man’s hand. Remembering Jackson always said no deal is real unless it is on paper or one shook on it.
“Good deal son, starting Monday you will have two different courses that will run you two weeks and then I will send you off to the New York branch or California branch to finish things up for another two weeks. By then you will either be coming back to sit in my chair or being let go with some severance and a real chance of having a real job somewhere else. Well I suppose there could be another managerial role open here at are branch, but I’m not really sure about open positions in other areas.”
“Thank you sir, thank you so much! When you started this meeting I thought you were going to let me go and, and… thank you.”
“I’m still not making you any promises Hatch. You have things you have to take care of, and things still have to work out on end. Now why don’t you take the rest of the day off, I can’t see a reason you should be hanging around here doing intern work.”
With a skip in his step Lincoln left the office, thinking about calling his mother and father about the amazing news, his heart was soaring till he saw Jacquline turn around in her seat. She uncrossed her sexy stocking covered legs and then re-crossed him as she smiled at him. On reflex he returned her smile with his own. His sourcing heart plummeting toward the ground, thinking about one of the requirements of the job. “So tell me handsome, how did it go?”
“Umm good, but I umm I need to go. Things to do and umm” Lincoln found himself laughing at nothing from nervousness. “I will see you later tonight, love you! Bye!”
“Wait!” Jackson called after him, the man was acting really strange and he wanted answers, but when he told him to wait he found Lincoln turning around giving him a kiss the lips that wasn’t long, but was much longer then the normal quick peck. “Sorry, I almost forgot that, we will talk later, but I have to go.” Lincoln walked away from the beautiful creature as quickly as he could, pulling out his phone wondering who he should call to talk about all of this. Moving to the elevator he was impatient to get to the ground floor so that he could make the call. She picked up on the second ring.
“Hey, Madison. A lot just happened at work and I really need to speak with you.”
The end, for now.
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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.
- Tags
- crossdress, crossdressing, feminization, m2f, transformation
Updated on Dec 23, 2023
by Nicegent42
Created on Aug 21, 2022
by Nicegent42
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