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Chapter 14
by Nicegent42
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Scene 14
“I just can’t believe it.” Lincoln said, staring at his friend, who looked sexier than they did when he dropped them off at their desk that morning. He had been a bit annoyed that Jacquline had bailed on their afternoon activities, especially without mentioning it to him. It was the same type of thing Jackson often did, but seeing Jacqueline now all was forgiven.
“I keep saying the same thing.” Jackson was miserable as he stood just inside the door to his apartment, his white blouse had an extra button undone, not able to contain the life-like double D breast forms that had been glued to his chest with surgical glue. And at the same time his lips felt like a bee had stung them with how inflated they were after getting surgery… he had actually let his sister talk him into what she called minimal surgery. Sure it only took an hour and a half to get a lip lift and another half hour for the filler, but the change didn’t feel minimal at all. The way his lips looked now, specifically his upper lip, even with his mouth closed when he was not actively pressing his lips together the lip lift made it so they didn’t fully touch at the center, leaving people to see a hint of his white teeth. The way Linc was eyeing him, made Jackson feel like he was a lion's prey about to be pounced upon, all while his sister practically encouraged it.
“I’m not complaining, but…” Lincoln waved his left hand in the feminized Jackson’s direction. Causing Jackson to groan how he had allowed this… any of this to completely take over his life. Lincoln smiled, taking an **** step closer thinking he heard the down right sexy creature in front of him practically purr at his attention.
“Simple.” Madison stepped closer to her sibling, cupping one of the breasts, causing it to jiggle in her hand. Lincoln’s eyes almost bulged out of his eye sockets seeing what she was doing, while Jackson gave a lazy look to his sister, not able to put up the mental energy to fight her after the day he had had. He was sure he would be a mess if she wasn’t supplying him with some of her xanax, something he was going to need to see about getting for himself soon enough. “These are much better quality than what we were using before. They match my little sister's skin tone, feel real and while Jacquiline disagrees with me the size is perfect for her role. The more people looking at her chest the less will be wondering if they had seen her before.” Jackson mentally noted that he at least talked her out of making him use the triple D breast forms. The place had smaller forms, unfortunately nothing that would match his skin tone. Jackson mentally sighed trying to take solace in the battle he did win, though between the medication and internal thoughts he had lost track of what the two around him were saying.
“Well I’m liking the changes, and I’m glad they help you feel more like the real you Jacqueline.” Lincoln said, referring to when Madison said the lips and breasts fit much better with the aesthetic they were going for with Jacquline, not realizing it wasn’t something Jackson actually wanted.
The sound of his new name brought Jackson back to the present. “Yeah, all this happened today.” Jackson said not really knowing what they had been saying, waving at himself as he tried to do as he was taught to talk more with his hands. “And so much more…”
“Wait, you had more done?” Lincoln’s eyes had roamed over Jacqueline’s body a few times, but he hadn’t noticed anything else, but he had to admit the lips and chest were eye-catching.
“Oh no, she got some news before she left the office today. Go on Jacqueline, tell him what you told me.” All of this felt hilarious to Madison, she had told her brother how silly it was to dress up for some event, but she had been more than happy to cut him down to size after all the pranks and shit he had given her over the years and now it was fully blowing up in his face. She wasn’t going to leave him to suffer alone, no she was happy to help, but in her own way.
Jackson held up his hand before walking past his sister, thankful she hadn’t kept bouncing his chest and past his friend in order to sit down on the couch. Lincoln took note of how his girlfriend or pretend girlfriend’s chest moved as she walked and then to her backside when she passed him. Madison was just happy her brother no longer needed to be reminded how to walk property in the heels or make sure he smoothed his skirt out before sitting down. She had always known he was charismatic when he wanted to be, but she really never considered him to be the sharpest tool in the shed, but he had picked up her instructions rather quickly. He hadn’t even reverted to his normal voice once today when they were alone or complained about how talking in the sultry husky voice hurt his throat.
Sitting down Jackson let out a small sigh of contentment as he slipped off the incredibly high T-strap high heels. He only rubbed on his sore feet for a second before remembering the night before. Looking over at Linc he pointed to the other side of the couch, giving him a look or hoping he gave a look that would make him do what he wanted without an argument. Smiling felt odd with his lips, but still a large one came to his face seeing his friend do as commanded. Soon as Linc sat down, Jackson moved his feet up onto his lap and tried to get comfortable or the best he could with the corset still tight around his waist.
Lincoln felt a little turned on when Jacqueline commanded him to come over, seeing her rub her own feet he knew what she wanted. At times she would act shy and demure, but almost always she was commanding when it came to wanting his attention. He had never been with a girl that acted dominante like that, but he was learning he liked it or at least so far he did. Taking one of her stocking covered feet between his hands, he started to knead out the stress that Jacqueline accumulated throughout the day, happy to see and feel her start to relax. “You were about to tell me about your day?”
Before Jackson could answer he heard his sister's voice from the kitchen. “Does anyone want a drink while I’m in here?”
“Heaven’s yes! Bring over the bottle of honey whiskey and a glass. After I say this, maybe we can just sit in silence while we watch the Dolphins game that was recorded.”
“What was that little sis? All I heard was you forgetting to say please.”
Lincoln looked over the couch to Madison, he absolutely still had a crush on the gorgeous woman, but it was hard for him to think about her like that when he was running his hands over the calf of Jacqueline's smooth nylon covered calf. He was sure she had to feel his growing arousal with her other foot on his crotch, but she hadn’t moved it except to flex her foot and wiggle her toes. The smile already present on his face grew a little more as he considered she was moving her other foot like that on purpose. “Maddy, could you make that two glasses please. I can’t have my girlfriend drinking alone when her Dolphins lose to the Seahawks.”
“Maddy? When did I become Maddy to you?” Lincoln looked away from the pretty gal back to his friend, she was touching her thick lips with one long nailed finger. A sight that encouraged what was happening in his pants, while his mind told him to be embarrassed for using the familiar name for Madison.
“I ahhh…” Madison started to laugh as she came over, putting two glasses on the coffee table in front of them. Pouring some of the honey whiskey into a glass of her own before sitting down in the recliner. “I’m just messing with you. If I can call you Linc, you can call me Maddy. WIth the two of you being madly in love it won't be long before you will be family.”
“Maddy… please.” Jackson whined.
“Please what? Help you plan your wedding? Accepted, no backsies!” Jackson closed his eyes, trying to ignore the maddening girl and just enjoy the feeling on his legs. After a second of no one saying anything he opened one eye, catching a look from Linc. After getting his attention, Jackson motioned over towards the glasses on the table. Happy to see the man doing what he wanted without him even having to utter a word. At least wearing a skirt came with a few perks he mused.
“Ignoring everything my sister says.” Jackson took a sip from his glass. “My dolphins are going to beat your Seahawks handily.”
“They won't, but also they aren’t my Seahawks, I only watch football with you and don’t have a team. I just know the Dolphins suck.” Jackson glared at the man as he continued to massage his other leg. “Traitor.” Jackson half whispered before taking another sip of the ****.
“Want to make a bet, traitor?” Honey whiskey didn’t burn on the way down as much as regular whiskey, the liquor was his favorite and the perfect thing after a day like today. While it had just hit his system and hadn’t had any real time to hit him, still Jackson felt feisty. It had felt like everything in his life had been taken out of his hands, he wanted to take control of something.
“Why am I a tractor exactly?”
“Because you are a Floridian.” Jackson pointed his index finger at Lincoln with the hand that held his glass.
“Okay… that doesn’t mean anything, but sure what would you like to bet?” Jackson tried to look smug, sliding his feet from his friend’s lap now that he was done rubbing on them. He had felt some warmth on his foot and something solid in his pants. The heat had felt good so he had pressed his feet into it when Linc was working on the other, figuring it was from his phone. Linc had always complained about his old phone getting too hot from use, but now that he was done helping relieve some of the pain from wearing the heels all day and into the evening Jackson didn’t want to leave them sitting there like he was really a girlfriend or anything. His sister taunted him enough, he didn’t need to give her more ammo.
“Good, then if I win you are going to be my own personal masseuse. I have never gone to one before and you do a…” Jackson let out a happy sigh at just the memory of his friend’s hands working all the pain and stress out of his feet and calves. “Wonderful job so far, you can consider it an unpaid promotion.” Lincoln raised an eyebrow at Jacqueline wanting for him to touch her more. He was going to say she could just ask and he would happily do that, but decided to hold his tongue. ‘If Jackson needs to use a bet as an excuse to show more of his real self, then I will let her.’
“If you win I have to be your physical therapist huh?” Linc rubbed his jaw watching as some liquid failed to make it into Jacqueline’s mouth, sliding down her chin and onto her cleavage. Jackson wiped his chin, looking down at his chest, not able to feel the liquid there, but knowing exactly where it had gone.
“Stupid lips…” Taking a cloth from the coffee table he dabbed his already annoying tits. “Yeah, and umm you have to do it whenever I want. If I came up to you at the office and tell you to rub my shoulders you have to. If I wake you up in the middle of the night and say I have a charlie horse you will have to take care of that. I call you come.” Jackson wondered if he was going to try and negotiate with him or make it up on his end of the bet. “Now what do you want in the off chance your stupid bird team wins?”
“Again, not my team.” Lincoln was about to go on when Madison interjected.
“I like this, I want in. The trouble is, do I want to put my bet on the fish…” Madison made eye contact with her brother when she called the sea mammal a fish to annoy him. “So I can have a personal masseuse, or do I go with the birds so I can make my precious sibling do something for me. Oh.. I could make her give me massages.” Madison scrunched her face before shaking her head. “No, that won’t do. Weak hands and no stamina.”
“I do not have…” Jackson started to rebuttal, but didn’t get far before his sister talked right over him. “Sure you do, so I will bet on the Sea Hawks and if they win. Then you, my little sister will be going out to a chippendales bar with myself and Callie. She still thinks she has a shot with you with how you openly flirted with her. I keep telling her how you are madly in love, but that girl knows what she wants.”
“Didn’t the two of you spend the night together the other night?” Asked Lincoln, confused with her talking about the bartender like the two of them didn’t just bang.
“Sure we did, and we will again, but it isn’t serious.” Finishing off his glass, Jackson thought about sitting next to Callie at a bar. His mind slipped into imagining the two of them and they could do together after a few drinks. “Yeah… I like Callie, she is pretty.”
“Looks like she agrees with my side, what about you Linc, what do you want?” Lincoln scratched the back of his head for a second before moving to refill Jacqueline’s glass when she held it out, adding a little more to his own.
“I’m still thinking, maybe for a week she has to wear her heels around the house or… no never mind.” Madison scooted forward in her seat, leaning forward as she focused on the man.
“First off, a week? My sister wants you at her beck and call, didn’t put a time limit on it and you want her to what? Wear a pair of shoes you like for a week? Come on, you can do better than that. What was it you were going to say?” Jackson really wished his sister would stop referring to him as a female, my sister this, my little sister that, but he knew if he brought it up again she would only remind him how he had to stay in character or risk being found out.
“I was ahh.” Lincoln was sure Madison could see the blush on his cheeks. He was a red blooded man and Jacqueline just came home and suddenly had a massive chest. Any size tits on a girl was enough to get his blood flowing, but he couldn’t help his attention being drawn to them.
“Come on, spill it.” Madison said with an eager voice.
“Yeah… spill it!” Jackson pointed his finger at his friend with the hand that held the glass, moving it violently enough that some of the contents splashed over the rim of the glass onto the couch. “Oops!” Jackson started to giggle at both the act of spilling some of his drink and how unintentionally it lined up so perfectly with what he had said. Madison glanced over at her sibling, the two of them shared a flatbread appetizer while they were out and knew that wasn’t nearly enough to soak up the **** he was drinking so quickly. She had already warned him previously not to drink while on the xanax, and he didn't listen then, so she made no attempt to stop him now.
“Oh.” Lincoln pressed his lips together for half a second before continuing. “I was going to mention umm touching her chest, but it was silly. I skipped dinner and maybe the **** is going to my head.” Lincoln felt embarrassed to just say that out loud, he needed an excuse. There was no way half a glass was going to ever hit him this fast and he did have dinner, it just wasn’t a proper one. No one ever called the poor man’s meal of butter noodles a proper meal, but after going out earlier this week and paying he was strapped for cash to go to the grocery store.
“Aww, your boyfriend wants to play with your tits!” Madison stomped her feet on the floor as she laughed.
“Breasts! You told me I can’t call them tits.” That only made Madison laugh harder. Sitting up more Jackson looked over at Lincoln, squinting at him. “Sure, if you win you can touch or play with them or whatever. Like I care, it isn’t like I can feel it. My boy Tua is going to lead the Dolphins to victory.” Looking down at his new rack glued to his chest Jackson blew some air out from his lungs, admiring the view. “They do look good right!?”
“They, really, really, do!” Madison had to break the sentence up, saying each ward between gasps of air as she laughed harder and harder.
“Great, that is settled… maybe we can now move on to what happened today before we turn on the game or we can talk while I start it up.” Lincoln felt incredibly uncomfortable talking like this, so openly sexual, it wasn’t something he was used to at all. It reminded him of the prank Jackson pulled about welcoming him and his date home saying they were welcome to the orgy. Knowing what he knew now about his friend, he wondered how much of it was a prank and how much of it was wishful thinking.
“I’m not going over my entire day, phone calls, some office gossip.” Jackson moved his hand limply, indicating his body. “All this… and stupid HR being all helpful.” Turning the tv on Lincoln raised an eyebrow, wondering what human resources messed up, he hoped it wasn’t about the rate of pay that was negotiated.
“They said I agreed to things in my paperwork and I don’t know what I signed, but my medical benefits are going to start right away now.”
“Okay, so far so good.”
“Let her finish, this is soooo good.” Madison said, putting down her now empty glass and opting not to have another.
“As I was saying!” Jackson looked between the two, accusing them both with his eyes of interrupting, even though he had paused. They give me a list of three therapists to pick from so I can talk about my transition and a list of two doctors for the same. Saying I have to see them both soon and regularly as a condition of my employment or some other bullshitttt!” Jackson kept making the T sound at the end of the word, smirking at the mouthfeel of the word.
“Okay I can see where you would…”
“I'm not done! You shush! Linc shush!” Jackson glowered at the man for a second before taking another drink from his glass, sad to see it was already half gone. “They also submit… submit… They gave my new information to the state to update my social security number. Letting me know it should be done within a week and then they would give me time off to go update my driver's license. They want me to just turn my whole life into being a woman!”
Lincoln nodded along, it was obvious his friend had gotten drunk rather quickly and that they were upset, but by how overly dramatic they were being he figured it to be more of an act. “If they are making you do it, then isn’t it better that they are handling it for you?”
“I suppose…” Jackson pouted, wishing Linc would commiserate with him instead of trying to point out the good side of the crazy situation he was stuck in.
“I told you.” Madison said in a sing song voice. She liked it when he reacted and right now he seemed to be in a mood so she left him alone as the recorded football game came on the tv. At one point she tried to get the two to switch to water, but the best she could get is that they drank a glass while they continued to drain the half bottle of honey whiskey she had brought over to them.
“Looks like you lost the bet little sis.” Madison felt incredibly upbeat about winning, but her words came out as she fought back a yawn.
“Yeah… lost. I’m going to bed.” Jackson’s eyes were already half closed, standing up he had to catch himself on the side of the couch, his weight distribution much different than before. He was halfway to his bedroom when he felt his sister turn him around and help him move a few steps in the direction of Lincoln’s room. He considered arguing, but didn’t have the energy for it. Going into the room he didn’t even wait for the door to be closed before he unbuttoned the blouse, it was a slow act between the long nails, his exhaustion, the mental fog of medication and **** and the buttons just being on the wrong side. Jackson didn’t even take the time to consider the fact that he had walked in the room, walking closer to Lincoln who was sitting on the bed taking off his socks as he slowly removed the blouse that was much tighter on him now than that morning.
With the blouse off, Jackson rolled his shoulders and turned around. Seeing the door was still open he closed it to have privacy as he got out of his clothes for bed. He reached behind his back, unclasping and unzipping the tight pencil skirt, just letting it fall to the floor. He wished he could take off the corset, but it was stuck on till his shower in the morning according to his sister. Jackson arched his back, stepping over to the dresser that had a large mirror across it. Seeing himself, Jackson put his hands on top of the dresser, leaning forward to take a good look at both his swollen lips and large chest, unaware of the show he was putting on.
Lincoln licked his lips watching Jacqueline slowly, sexually undress in front of him. He said nothing, just watched her and continued to disrobe himself, not wanting to ruin this moment. The two of them didn’t get their alone time this afternoon like they had agreed and she seemed all about having his hands on her for the bet… that and she seemed almost eager to have him play with her new chest. The way she leaned forward like that, her ass thrust backwards compelled him to stand and move to her. Lincoln normally slept in just his boxers, but right now he was fully nude as he approached the girl giving him a siren song. Before he got to her, Lincoln watched her pull the cups down from her overbust corset, letting the beautiful breasts hang free. He knew intellectually they weren’t real, but his eyes couldn’t see the difference. “Oh yes.” Lincoln said almost closing in from behind, his erection at full mast.
“Yeah…” Jackson said in reply, not thinking about who said that, only agreeing that the large tits looked wonderful as did the image of the dark haired girl running her long sexy fingers over them, playing with herself. “MMMmmm yeah, just like that.” Jackson said talking to the girl as if she was a different person. Jackson felt Lincoln before he saw him in the mirror, being way too focused on himself. The man was pushing himself, his hardon against his ass. The feeling caused him to ask and straighten up, but as he did Lincoln’s hands touched his hips, running up across his corseted stomach and cupped the large breasts, helping take the weight off.
Feeling his dick press against him was jarring even to his addled mind, but the image in the mirror was still sexy, it was like a porn video was playing out in front of him. The movie was his friend Linc playing with a girls large tits, and by the bulge in her panties he knew exactly what type of movie it was going to be. “What are you… oh, oh, ahhh!” The question, while he couldn’t really feel his fake breasts being kneaded other then the pressure, he could easily feel the tingling feeling of being kissed on his neck. Lincoln’s soft lips a contrast to the scratchy feeling of his five o’ clock shadow across his **** neck.
“Just getting my reward from the bet.” Lincoln said, moving both hands from the large fake breasts that felt so real, even the nipples were hard. He wasn’t sure if they were originally, but right now it added that extra level of realism as he kissed her exposed neck. Moving his hands down to her hips he pulled her ass back into him, sliding one forward to her stomach to hold her there as he went back to touching her chest, not just feeling her, but watching her squirm in the mirror.
“The bet… yeah… but you're naked.” The scene playing out before him had him more than aroused, but his mind was so muddled he wasn’t really sure what was happening other than it looked sexy, the kissing on his neck felt good but what he felt on his ass was wrong. Seeing Linc kiss the girl on her collarbone, the kisses trailing up her neck while he felt it happening caused him to bite his lower lip. “Mmmmm” Slowly he closed his eyes wanting to enjoy the feeling, but as he did he became more aware of his friends pressing into him. Putting his hands on the dresser Jackson pushed back, causing Linc to do the same. With the space Jackson turned around, not wanting to be so close he stepped back till his rear pressed against the dresser. His eyes were heavy, he blinked them a few times, fluttering his mascara covered lashes. “Lincoln…”
Lincoln let out a small growl, watching Jacqueline pivot away from him, her breasts fully on display as she seemed to beg for something or maybe commanding him to do something as she said his name in that husky voice. Moving forward he wrapped his arms around her, one hand on her back, the other moving up to hold the back of her head. Lincoln’s fingers sliding into her updo as he pressed his mouth to hers, his tongue sliding into her mouth as she opened it welcoming him.
Jackson’s eyes went wide as his friend practically charged him, pulling him into an embrace. He opened his mouth to protest, only to feel something slip into his own mouth, tasting much like his favorite drink. As their lips pressed together a feeling of pain ran through his still swollen lips, mixed with pleasure. Slowly his eyelids lowered, his legs felt weak, but pressed up against the dresser and held in Lincoln’s arms he didn’t fall. With a last bit of resistance Jackson moved his own arms up to push him away, but when Lincoln’s lips came from his own and went back to his neck his legs went from weak to rubbery, causing him to wrap his arms around his neck to keep from falling instead of pushing him away.
His mind was so foggy, Jackson wasn’t sure how he ended up in bed, when he was sure just a moment ago Lincoln had wrapped his arms around his thighs and had lifted him up to sit on the dresser. Lincoln was next to him in bed, but the lights were off, he wasn’t even sure when that happened. He knew his best friend had been making out with him while he was naked with a hard on… and that he had kissed him back. They were still embracing, Jackson having one hand in Lincoln’s hair as the man rubbed his warm hands over his cool body in the dark room when he started to drift off to sleep, hearing his friend say something that made him smile, he had lost the bet, but was still getting what he wanted. “For you Jacqueline I will give you a massage any time.” Jackson drifted off before hearing the rest of the sentence. “Just like I know you will use your sexy body to turn me on, and then demand you get to pleasure me. Baby you have no idea how sexy it was when you demanded I let you give me a blow job.”
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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.
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- crossdress, crossdressing, feminization, m2f, transformation
Updated on Dec 23, 2023
by Nicegent42
Created on Aug 21, 2022
by Nicegent42
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