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Chapter 12
by Nicegent42
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Scene 12
Leaving the break room Jackson paid little attention to the world around him as rushed off to the bathroom and knelt inside the first stall he could find. He **** himself to cough and when that wasn’t working his put one finger into the back of his throat to **** himself to be sick and expel the contents from his stomach. The burning sensation from the stomach acid filled his throat as what he had just swallowed splashed down into the porcelain bowl. He let out a groan as he looked down at what came up. Jackson couldn’t believe Linc had done that, that he had done that, that he even thought a hand job was okay. Yet there it was, cum along with other things in the toilet, he had swallowed cum, his best friends cum. If he hadn’t just emptied his stomach the thought might have made him sick once more.
“You okay there?” Jackson, down on his knees in the stall, turned to look at the man who had spoken. It was someone he had talked to on more than one occasion, Abraham or Abe the current top salesman on Dunn’s team. Right now he felt like crap so he shook his head, this throat feeling raw from his recent activities.
“Sorry to hear that, let me help you up and get you over to the woman’s bathroom.”
“Woman’s bathroom?”
“Yes ma’am, in your rush I’m guessing you didn’t pay too close attention to which bathroom you ran into. I can understand that, can I get you anything? Water, an aspirin or anything?” Jackson closed his eyes and rocked his head back for a second. ‘The mens room, I’m so stupid! I could have just outed myself.’ Jackson accepted the man’s hand as he got to his heeled feat, and unfortunately for him having to accept the hand that held his side when he almost tumbled. “Thank you, I will be okay.”
Abe nodded, taking in the young woman in front of him, trying not to leave his eyes near the plunging neckline of her blouse. “I’m sorry again you aren’t feeling well, but perhaps you might want to head into the other restroom to fix your makeup and I can get you a bottle of water. Jackson looked past the man at the large mirror on the wall seeing that his lipstick was smeared and trails of his mascara were on his face.
“Tell ya what, I will go get your purse for you if you can tell me where your desk is, no need for you to show yourself in front of everyone like this. This office is just one big rumor mill, you don’t need any of that. I’m Abraham by the way.” Jackson could understand why he was so good at selling with his friendly demeanor and easy smile.
“I’m Jacqueline and you can find my purse in the bottom drawer of my desk, right outside Mr. Dunn’s office.”
“Oh you are the new girl. Considering the time of day I doubt I will be the first to say this, but welcome to the team.”
“Is this where you offer to show me around or go out for drinks? Because I’m not single.” After what he had just done Linc better not be backing out now, Jackson thought as he stabbed his hand with his long nails when he made a fist.
“By that tone I’m guessing a few of the guys haven’t left you alone. I apolgize for my gender for being stupid and unable to take hints. I truly can’t blame them for wanting to get to know you, but I’m sure they handled it poorly. I have a little pull around here, I will try and make sure I mention you are happy with your boyfriend or…” Abe let the word drag out as he raised an eyebrow.
“I’m happy with my boyfriend, he works here too, Linc Hatch.” Abe closed one eye, the name tickling something in the back of his mind.
“One of the interns, nice enough fellow from the little I have seen of him, hard worker and apparently lucky in love.” Jackson let out a soft laugh at the idea of Linc having any real skills with women. After feeling like some of the men were undressing him with their eyes, having a conversation with Abe felt nice. Even in the men's room, talking to someone who he had multiple conversations with, still his secret wasn’t out. It took a bit to fix his makeup after Abe had brought over the purse. Jackson wasn’t exactly skilled with makeup, but eventually he was able to get back to his desk without more hassle and found a bottle of water waiting for him.
Sitting down in his chair Jackson crossed his legs like his sister had drilled into him and signed back into his computer and noticed more than a few missed calls. When he rushed off to take care of his last problem he hadn’t even considered sending the line back to the secretary pool. “Hope I didn’t miss anything important.” He said to himself knowing nothing in this job was important.
“I would think you did.” The voice from behind Jackson startled him. He swiveled in his chair to look at his boss standing in his office doorway, wishing the man had a bell around his neck. “How do I like my coffee?” Alexander asked, doing his best to not look down his secretary's blouse.
“Umm two sugars, no cream?” Jackson watched the man nod to the question and just stare at him for a few seconds not saying anything, but motioning with his hand like he wanted more. Jackson wasn’t sure what else to say, but started to feel smaller as Dunn’s eyebrows went up. It felt like he was being stared down for giving the right answer.
“And where is this coffee I asked for?”
“Oh shit.” With everything that had happened Jackson didn’t remember the coffee at all.
“Jacqueline, you are pretty enough eye candy, but if you can’t remember a simple order for coffee then you and I will have to have a long talk about what else you can do. No one expects you to be smart, your job is to look pretty, answer the phones, handle my schedule, do some filing and make sure I have my coffee.” Jackson opened his mouth to reply to the completely sexist remark, but with the hard look he was getting and the fact Mr. Dunn was pointing off in the direction of the break room he thought it best to just do as he said.
Both him and Linc had to make sure conference rooms had coffee and water more than once over their time as interns, but being ordered to go fetch coffee while being told part of his job was to just look pretty was both demeaning and humiliating, but at least this time the older man hadn’t touched him as he walked away. Jackson looked up to the ceiling thanking the heavens for the small miracle as he made his way back to the break room in the uncomfortable attire.
For Jackson the rest of the day went back to the boredom he encountered earlier and without being allowed on his phone he started to understand why he had seen some of the other office girls working on their nails or reading a magazine, but soon enough it was over and he couldn’t wait to get home and get some real food in him after only having two canned diet shakes today… and something that he really didn’t want to think about ever again. Shutting off his monitor and putting the purse in the crook of his elbow Jackson made his way back to his old cubical.
“Still good to give me a lift home handsome?” Jackson said with lilt in his voice and a smile on his lips for those nearby that might be listening. What he really wanted to do was pop Linc in the mouth with his fist and take his keys after what he had done.
“Hey there beautiful! Lincoln turned in his chair to see his dolled up friend smiling at him. He had gotten almost no work done at all after what happened in the supply closet. The encounter confused him, but in the end he decided Jackson liked this and wanted it and everything else was an excuse to make it easier. If someone was forcing him to dress as a woman then it wouldn’t be his decision and he wouldn’t have to say he was coming out. Course, it was absolutely Jackson… Jacqueline that pulled him into that supply room for some office fun. “Yeah, let's get out of here.” Standing up from his computer Lincoln put one hand on his friends hip as he leaned in for a kiss, but his lips landed on her cheek, but she did accept his hand as they made their way to the elevator, down and out of the building.
When they arrived home both were surprised to find a few things had changed about their two bedroom apartment. All the furniture was the same, but a few small things had been added. A knitted afghan blanket hung over the couch, a small potted plants were place around the apartment along with scented candles and coral colored drapes now on the window that looked out to the street below. “What is going on here?” Lincoln asked as he stepped more into his apartment.
“MADDY!” Jackson yelled, he just wanted to come home, take the bloody heels of his feet and have dinner. He did not want to deal with his sister changing more of the apartment then they agreed. The door to his bedroom soon opened and out came his sister wearing a wool cream colored sweater, a jean skirt with buttons going down the front that stopped just below her knees and tan panyhose, but her feet left bare of shoes.
“Hey sis, hi Linc! I hope the two of you had a good day at work, I finished moving in about twenty minutes ago. You guys just missed the movers.”
“You moved in!?” Lincoln would have jumped at the chance to have Madison be his roommate over Jackson, but he didn’t remember having a conversation about it let alone agreeing to it.
Jackson turned to face his friend, feeling sheepish that he had forgotten to discuss this with him. He had thought he would of course agree to the girl he had the hots for moving in, but didn’t actually bring it up. This felt like a much bigger thing to slip his mind than Mr. Dunn’s coffee order. “I was supposed to talk to you about that… Maddy is going to sleep in my room and I forgot to bring it up.”
“Yeah Jacqueline, that is definitely something I should have known about. If she is moving into your room, where are you going to sleep?” Jackson winced at the use of the feminine name, but before he could speak up his sister answered the question.
“In your room, the two of you are supposed to be in love and knocking boots and all that.” Lincoln whirled to look his friend in the eye, unable to believe news of Madison moving in never made it to him, but news of the blow job had made it to her.
“You can’t just go and tell your sister about what we do behind closed doors. We absolutely need to have a talk about communication and boundaries.” Jackson’s eyes grew large as he looked between his friend and his sister. “No, no, no, no! He is just kiddy Maddy.”
“Oh my god! Did the two of you hook up? I thought I saw some chemistry the other night.” It was a surprise to her that her little brother decided to try being with a man, she didn’t think he was like her and happy to be with either sex. Madison bit her bottom lip as she appraised her brother still in the work outfit she had sent him off in. If there was a time to experiment it was when he looked the part of a woman.
“Maddy, it isn’t like that!”
“No worries little sis, I do not need the details. But for you Linc, here is the four one one. My rent was going up by more than I could really afford. I had a boyfriend I was going to move in with, but that ship has sailed and your girlfriend said I could move in and we could split the rent three ways. I have already moved her clothes and makeup into your room and as a thank you present you will find new sheets on your bed. Cream colored silk sheets along with a white and coral comforter with matching pillow cases.” She loved the bedset, but was happy to part with them considering it was a gift from her last boyfriend and they would give that pop of femininity to the bedroom.
“I am not sleeping in the same bed as him!”
“You need to keep up appearances and it kind of sounds like you have already moved past that. So… I’m gonna run out and pick up some dinner for all of us to celebrate my first night here.” Madison pointed to Lincoln. “You, sit on the couch and rub your girl’s feet and ask her about her day.” She then pointed at her feminized brother, thinking the two of them really did need to sit and talk about his new open mindedness. “You let him pamper you, trust me on this.”
“We aren’t done talking about this!” Jackson called after his sister. Lincoln looked his friend over, those long legs perched in those heels made them and her ass look incredible. He knew she was interested with what happened earlier, but her refusal to sleep in the same bed as him was probably coming from the same place that made his friend feel the need to lean on the excuse of being **** into this. When Madison went back into her new room he watched Jacqueline move after her sister, him watching the shift of her hips and movement of her rear with each step. Unaware of the rope and belt training Jackson went to walk the way Madison wanted he could only think no man would walk like that.
Jackson’s eyes darted around his room as he stepped in after his sister, literally nothing in the room was his. She had a picture or two hung on a wall, her dress up manikin in one corner, the closet packed with clothes and shoes, even his bed and dresser had been replaced. His heart started to beat faster as his eyes slowly moved to his sister as she was putting on some calf high brown leather heeled boots. “Where are all my things!? This isn’t what we talked about!”
Rolling her eyes Madison pulled one foot into a boot, zipping it up before looking to her sibling. “Sure it is. You have everything you need in the master bedroom and bathroom, though we still need to expand your wardrobe some more and the rest are in storage, along with what I couldn’t bring here. Just like we talked about.”
“That isn’t…!” Jackson stopped talking when he felt a tap on his shoulder.
“Hey how about we leave her for now so we get dinner sooner, rather than later. For now I think I owe you some TLC.”
“TLC? Whoooaaa!” The world shifted for Jackson as Linc bent down, putting his arm under his knees and the other his back as he picked him up. He smiled at Madison as he started to step out of the door. “Don’t know what you are getting, but I don’t like onions unless they are sauteed till they are soft.”
“Let me down!” Jackson complained, but did not dare move other than to wrap one arm around his friend’s shoulder so he didn’t fall and hurt himself. “In a second my princess.” Lincoln figured if Jackson needed to feel compelled or pulled into the things he wanted then he was okay helping him do it so he could explore who he really wanted to be. Jackson had always been this outgoing and at many times annoying guy, but he guessed deep down he wanted to be more submissive, than domineering and hadn’t wanted to admit it. When Lincoln put him down on the couch he sat down on the other side and put the heel in cased feet on his lap.
“Linc, don’t…” Jackson said pleadingly, being carried like a girl just added to the stress and anxiety of the day. It wasn’t a warning light alert bad, like when Dunn had him in his lap, but he didn’t want him running his hands on him. That thought and the concerns halted their advance in his mind shortly after Linc had slipped one of his heels off his feet and started to kneed his hands into his stocking covered foot. The soreness from wearing the stilts started to subside. The muscles in his foot started to relax and as they did a sense of calmness came over him. Being touched by another man had no right to feel this good, and while a second ago he was telling him to stop, feeling it Jackson didn’t want him to ever stop. Closing his eyes he left Linc to the massage, while he smiled now knowing for the first time why people pay to go get a massage.
Lincoln held the nylon covered foot in both hands, he started to rub the top of the foot using a firm motion with his thumbs, touching the base of each toe. Then moved his thumbs in a parallel motion down the foot to the heels and up to the ankle. Then went back up the foot with a lighter touch, repeating the motion four times before his hands moved up to the calf where he used his other fingers together till he felt the tension left the smooth leg. With that done he pulled Jacqueline's other heel off to start on it, only taking his hand off the leg to wave goodbye to Madison. He smiled the whole time as the beautiful creature he was massaging went limp, all protests gone, all words gone other than a few mews of pleasure. He was considering going back to the first foot when the sounds coming from her had changed to a light snore.
Taking a few minutes to just smile and look at the sleeping form of his girlfriend he reflected on the situation. It was odd, more than that really, but he was happy. He still didn’t know how he really felt about dating someone that had a dick, but there were reasons why Jackson and him were friends and he couldn't deny he was attracted to Jacqueline. This was new territory for him, for both of them. He pulled out his phone slowly in order to not wake her up, he wanted to research things like being transgender and what it meant, and to see about his friend’s need to feel ****. One of the first things he found was a blog about the desire to be feminized. He clicked on the link, then looked over at the rising chest with the fake, but realistic breasts. Deciding that must have been an expensive investment, way more than someone would pay for a single day. The only thing that really didn’t fit the mold was those moments of true boldness where Jacqueline demanded, commanded him to be her boyfriend and when she dragged him off to the supply room.
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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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