chapter 7

Chapter 7

“Eva, would you hand me a cotton swab?” Reagan asked, his eyes glued to the little purple compact mirror that he’d been keeping on his person every day since his foray into femininity one month prior.

“Of course, Reah,” the campaign manager replied, digging through her purse and retrieving the little white disposable tool. As she watched her boss take the q-tip and then, with a little dab of makeup remover, perfectly carve away the tiniest imperfection from his lip-liner on his plump lips, one that even she didn’t notice. The candidate’s notorious reputation as a perfectionist was well earned. Here was Reagan Demir displaying the same attention to detail that he’d have used to polish his wingtips.

‘Damn,’ Reagan thought. He hated being seen as a woman, and even worse having to play the role. Even more still, he hated the idea that every imperfection would, or at least could feed a narrative that the whole act was for show. It was, but the rest of the world couldn’t know that. If they did, his chances of success would come crashing down once more. He didn’t want to care about his makeup, but anything worth doing was worth doing right.

It was then that Eva’s thoughts drifted back to their first lesson in cosmetics. The morning after meeting the staff, she knocked on his door around eight in the morning. When Reagan awoke, he thought it all a dream - that is until he felt the wisps of lace at the hem of his white nightgown, dancing on his thighs in the morning air. He attempted to sleep without it, but there was an absence of masculine attire in his closet, so his birthday suit was his first choice.

Under the covers was too hot in the Florida summer air, and going without too cold. A thought of Goldilocks crossed the freshly feminized man’s mind, and his stomach turned. Looking down at his body, without the underwear and breast plate, his slender frame somehow still appeared more feminine than masculine. Be it the red polish adorning his toenails or the silky smooth legs as they rubbed together, whatever the case it somehow seemed inappropriate to go uncovered. Reluctantly, Reagan selected the virginal garment and crawled back into bed, enjoying the sensation of the cool fabric far more than its girlish appearance.

The knocking continued, and as much as he wished it was work of the Sandman, it wasn't. So, after a brief moment to steel his resolve, Reagan managed to pull himself up from the mattress to face the day. As he frantically searched the room for a garment he could easily understand how to don, the best option was a matching white peignoir, a companion piece to the short nightgown, decorated with soft marabou feathers around the hemline. He might not have been a fan of the ensemble, at least on his own body rather than that of one of the pretty little creatures he’d bring home after a night out, but to Eva, it was a sight to see. Even without an ounce of makeup, Reagan still somehow appeared as though he'd always been the disheveled woman who was answering her door.

"I do love those little pearl studs, Reah. Glad you put them in before bed like I suggested," Eva gushed, barging through the door and emptying the contents of her day-bag onto Reagan's kitchen table. Glancinging at Reagan, she took in his feminine appearance once more - his thinly arched eyebrows that were now much darker than his blonde hair thanks to the microblading, the pearl earrings in his ears, his plump lips, and his current attire. With a smile, she turned and started walking back to his bedroom, knowing he would want to change. She needed to handle him carefully or risk the wheels coming off this campaign.

Reagan wiped more sleep from his eyes, careful not to slip up, and removed one with the brand new scalpels now affixed to each finger. "That's because you said they'll just stay sore if I don't stretch them back out. I've accepted that this is the way I have to dress, at least until after the election, but that doesn't mean every single part of me has to be completely uncomfortable until then." Even as the words escaped his lips, he didn't quite believe them himself. The idea of comfort seemed like something he might never actually experience again. "Let me go get dressed, and then we can discuss the day. Do you happen to know if there are any pants somewhere? I haven't been able to find a single scrap of my own clothing since I got back."

"Don't be silly, girl, those are your clothes now," Eva said, giggling. "You need to start thinking of yourself as a woman if you want to be able to keep this up without getting caught, so we decided that for the time being, at least, it's just skirts and dresses. The interns donated all your old things to charity."

“Are you kidding me, Eva?” Reagan shouted, gripping his disheveled hair, as he collapsed back onto the white downy comforter atop his bed. “That stuff was worth at least fifteen-thousand dollars. What about my father’s watch?”

“Calm down, missy.”

She knew the watch meant a great deal to Reagan. He wore it for luck, with a level of superstition typically reserved for professional athletes, and problem gamblers. “I know you’re upset, but that’s no reason to talk to me like that. I’m on your side. It was supposed to be a surprise, but the watch is off, being refurbished.” Eva looked Reagan in his deep blue eyes, and offered a lopsided grin.

“I wanted to give you a gift. I know all this is a big change, but you’re tough, you’ll get used to it. Anyway, traditionally feminine ensembles usually test better in conservative focus groups. Speaking of femininity,” Eva motioned towards her boss’ crotch.

"Yeah," Reagan said, exasperated. "I know what I'm wearing, and I don't want to wear it."

"No," Eva shook her head. "That's not what I mean. You're wearing exactly what you should be, but you have a rather masculine bulge that needs addrEseng."

Reagan nearly let a snide comment slip, after hearing what he thought sounded like a pick-up line, but then he glanced down to the offending area. The garment was smoother than anything he'd worn to bed before, and its cool material had given him a slight bulge. It wasn't a raging erection, subsiding immediately at the overwhelming shame now flowing through him like a raging river.

"What do you mean?"

"I mean..." Eva sighed, holding up a finger as she pulled out her phone. She had no intention of helping Reagan manually, so he'd need to read some instructions. "You need to look feminine down there… even when you're alone." When he just stared at her, blank-faced, she held out her phone, displaying a tutorial. "You have to tuck your dick away, Reagan."

Snatching the device, Reagan looked at the screen in horror. "Please no..."

Eva grew up with a literal drill sergeant for a father, and he regularly preached about the need to break someone down before rebuilding them. For the first time since they'd met, Reagan Esen Demir seemed utterly defeated.

"Don't worry about changing clothes yet. Today we're focusing on the fundamentals, so you might as well keep that pretty little number on while we spend some time at your new vanity. It's absolutely adorable on you, and you need anything that can help you start to feel more like a proper lady. We have a decade of lessons to catch up on, lessons most women learn in middle school. You need to be an expert by next month at the latest. Not a single hair should be out of place, literally or metaphorically, by the time of your next fundraising banquet."

Reagan flushed with embarrassment as Eva continued her commentary, each remark a stark reminder of his past and the feminine persona he was now expected to embody. He knew she was enjoying this, perhaps a little too much, but Eva was a political powerhouse. If this was her approach, he trusted her judgment. He remained silent, refusing to give her the satisfaction of hearing his protests.

'This is for the future, Reagan.' he reminded himself, a mantra he'd used throughout his life to push through challenges and achieve his goals.

For the next four hours, Eva rigorously trained Reagan in the basics. He'd apply a layer of foundation, only to be told to remove it and try again. His skin was flawless, but Eva knew that wouldn't always be the case. She'd place a mark on his face and then guide him through concealing and blending until the imperfection was subtly masked. Finally, half-satisfied with his efforts, she allowed him to move on to the intricacies of eye makeup.

Twenty attempts later, and Reagan was emotionally depleted. “Isn't this good enough yet?” he whined, glaring at his reflection.

"Well, we have to go grocery shopping after this," Eva said, "to get some things for your new diet. If you think your face is good enough for that, then we can go." Manipulation came easy when she knew her old friend would do anything to avoid shame and ridicule.

Without another word, he removed the makeup and began his efforts in earnest once more. Images of an old lady shouting, "That's a man!" in the supermarket flooded his mind.

Back in the present, in the car, Eva marveled at the transformation. The pathetic mess in the diaphanous sleepwear, complaining about the most basic of cosmetic techniques, was now preening in the mirror with the obsession and competency of a Hollywood makeup artist. "You look beautiful, Reagan. Stop fussing. Are you ready for this? They're probably going to be the toughest crowd you've ever faced."

The arrogance she'd worried was gone had returned in full ****. Reagan scoffed, "Eva, I was born ready," and then opened the limousine door with practiced feminine grace, stepping out into the parking lot of Burnt Poplar Elementary School.

Keen to distance itself from the rural parts of the area, this particular school was eager to showcase a welcoming and accepting Florida. They were proud to host the first openly transgender individual seeking federal office from their great state. When Reagan first heard of the invitation, he scoffed, wondering how a bunch of children, well below voting age, could possibly help his campaign. Eva, however, saw an opportunity. She reminded the candidate that the position was determined by popular vote, free from the district gerrymandering of the House. Suddenly, the densely populated urban areas became far more valuable from the calculating blonde's perspective. Liberals loved treating their kids like royalty, a practice Reagan believed weakened children. Eva assured him a meet-and-greet with the children could solidify the progressive vote in St. Petersburg, where the school was located. Similar stops in Orlando, West Palm Beach, and even purple Tampa could have a similar effect, especially with the lackluster candidate they were running against that year.

In reality, Eva wasn't sure visiting the kids would significantly impact the election. However, the visual of this proud, soft, caring, Christian woman teaching children about common sense morals and values would be a perfect addition to the new campaign commercial they planned to shoot that day. She quickly booked more appearances in the area, ensuring a camera crew would follow them throughout. All that remained was to choose the perfect outfit.

The brilliant strategist knew that, despite the evidence of numerous pornography scandals at the state capitol, even the most staunch conservative was more likely to accept a transgender woman if she presented as feminine and attractive. Drawing inspiration from a Sunday school teacher from her childhood, Eva kept a specific image in mind. Like that woman, she would project an image of a devout, tasteful, and attractive woman whose modest dress revealed nothing inappropriate, yet still exuded an alluring femininity.

For undergarments, a simple white cotton bra and panty set was selected, and though comfortable, they did little to assuage the agony in Reagan's rib cage from the boning of the tight black corset. Over that, a simple sleeveless blue silk top draped flatteringly over his false curves, tucked into a simple white A-line skirt that fell just below his knee, flowing with each twist and step. For shoes, a pair of two-toned pumps were chosen, white at the pointed toe and taupe on the heel. Gold earrings consisting of two interlocking hoops perfectly complemented the most important piece in the entire ensemble - a simple gold cross around his neck, hanging low enough to subtly suggest the cleavage it concealed.

In his apartment that morning, as Reagan was about to leave, he checked his reflection one last time. Eva was right, the clothes helped create the desired image, but it only fueled the screaming voice of his crumbling masculinity, constantly reminding him of how far he had fallen. Then, a small gold bangle, shaped like a nail or spike, caught his eye on his dresser. "At least one thing I wear today will be masculine," he thought, slipping it on before heading out. It was a small act of defiance, a flimsy attempt to cling to a fading sense of self.

"Cute!" Eva squealed as he slid into the back of the vehicle. "That bracelet is perfect, Reah. Now you're getting the idea. Keep picking pretty things like that, and I won't have to lay out your clothes anymore. Way to think like a woman." That comment extinguished the last embers of his resistance.

As Eva watched Reagan stroll to the school across the potholed minefield of a parking lot, her thoughts drifted back to another lesson they'd had weeks before. She wanted to hire a governess to teach her boss proper comportment and the intricacies of formal etiquette for women, including ballroom dancing. However, Eva knew her feminized friend might explode at the thought of being instructed by a matronly woman, given his upbringing, so she decided to tackle the challenge herself.

While Eva had no personal interest in salad forks or the foxtrot, she dedicated the next month to educating herself on these topics and then teaching Reagan what she learned the following day, right after morning makeup practice. One thing she didn't need to learn was how to live in high heels. A fervent feminist, the seasoned political strategist believed flat shoes were for quitters, as she often said, and had spent her twenties perched at least three inches above the ground. When it came time for Reagan to practice his gait, Eva was relentless.

She'd **** him into the tallest pair in his apartment - six-inch strappy mules with absolutely no ankle support. When Reagan first saw them, he complained about the feathers decorating the toes, but after a few steps he was far more concerned with the searing pain in his calves as he struggled to maintain his balance. Eva couldn't help but take a perverse pleasure in watching her old friend, a man who excelled at almost everything, struggle and whine like a little girl **** to wear a dress to church.

It took a month, but soon Reagan was strutting around the residence as if born in the ridiculous slippers. Ascending and descending the stairs posed no challenge, and his excessive confidence returned. One morning, when she placed the shoes in front of him, he laughed and said, "I thought you were going to make this difficult." That was all it took. She made him wear them all day, every day. He cooked in them, cleaned in them, and even napped in them occasionally. He'd complain that no one would ever endure such footwear in real life, but she'd remind him how easy he claimed they were, a subtle jab at his masculine pride. "It's bad enough you have me baking pies," he'd grumble, "but why do I have to do it in these torturous things?"

"You might think it's awful now, but one day you'll thank me for it," Eva said, her words echoing his mother's frequent admonishments during his childhood. He would have thanked her that day in the elementary school parking lot, as he navigated the crumbling blacktop with surprising grace, that is if he were capable of sincere gratitude.

For the next several hours, cameras rolling, Reagan charmed the children. They asked questions about elections, his previous government roles, and one boy, the obvious class clown, even asked if Reagan had "the surgery”. The team had anticipated this question. Reagan responded with care and compassion, explaining that it was a rude and inappropriate question but praising the child's curiosity. Internally, however, Reagan was ready to strangle the boy. He was suddenly empathizing with the transgender individuals he was now **** to emulate. He even found himself agreeing that the idea of inspecting children's genitals before they could use the bathroom was probably a terrible idea.

The next stop was a speech at the VA. Veterans were traditionally a Republican stronghold, but recent years had seen a shift. Older veterans often complained about DEI initiatives, while younger veterans were the very beneficiaries of those initiatives. With the younger generation now up for grabs, Reagan's campaign strategy focused on winning over veterans from the Middle East, Vietnam, and the dwindling Korean War era. Most of them didn't understand transgender issues, they just simply disliked the concept, especially after many evenings spent listening to Sean Hannity. Their ignorance was a blessing, at least in Eva's view. She believed that most of the older veterans, upon seeing his blond hair and curves, would be won over without much effort. As long as Reagan focused on lowering taxes and eliminating "free rides," the rest would fall into place. The only concern was his speaking voice. If he spoke from the chest, booming across the room as he used to, it would be a disaster. But Eva was confident that wouldn't be an issue.

A skilled public speaker since his high school debate team days, Reagan had no trouble with stage fright, eloquence, or even manipulating facts. From the stage, he could make anyone feel like he was their best friend, looking out for their interests. That's why watching him struggle through his vocal training was so amusing to Eva.

Eva, despite her years of experience in the political arena, was not a vocal coach. She hired a professional to work with Reagan once a week. The feminized blonde had to endure hours of vocal exercises, reading pages of material designed to strengthen the specific muscles he needed to use.

To Reagan, initially forcing such a drastic change felt unnatural, especially when his heart wasn't in it. Eventually, his resonance shifted upward, and his tone softened. However, something still felt off. The vocal coach thought he sounded like a child asking for seconds, not the born leader she’d observed when reviewing recordings of his previous speeches.

"See," the elderly woman said, her reading glasses perched on the tip of her nose, "this is what needs to change. Miss Demir, you've made significant progress. If you were anyone else, I'd say excellent work, but you'll be addressing thousands soon, and you're just not there yet. I hope watching yourself will rekindle that spark and motivate you to learn how to project. Before, it seemed effortless, almost instinctive. You need to reach a point where it feels natural again. Speaking like a lady is easy, ma'am. Shouting like one is the challenge."

This marked a turning point for the candidate, not because of the instructor's intended inspiration, but because it triggered a memory. He recalled his first meeting with his new staff and imagined how he must have sounded to them. An image surfaced, a hulking football player in a tutu reciting the Declaration of Independence. It was the kind of trans joke he'd made countless times. Now, as the punchline, it wasn't so funny. He thought of an older transgender woman he'd often seen at the local grocery store, someone who'd transitioned too late in life to quickly adapt new mannerisms or speech patterns. He imagined the toll the transition, both physically and emotionally, might have taken on her. He recalled sneering at her every time he passed, disgusted by her presence in public. One thing was certain: he didn't want anyone looking at him with that same disgust.

After that Reagan's practice intensified. Three weeks later, the teacher declared him proficient, but emphasized the need for ongoing practice to maintain his new vocal range. Fueled by the terror of another public humiliation, Reagan rehearsed his speech to the Veterans at least a dozen times daily, until every inflection was ingrained in his memory. Later that week, while shopping for his nightly cooking lessons in heels, Reagan encountered the older transgender woman. Instead of his usual disdainful gaze, he kept his eyes fixed on the front of his cart, and minded his own business while Eva sorted through apples.

Eva watched with a sense of maternal pride as her candidate addressed a hundred angry old men, passionately advocating for American values and support for the troops. The room, filled with registered Republicans, erupted in a standing ovation as he left the stage. To top it off, the entire event had been captured on camera.

The final stop for the shoot was the campaign ad’s stinger. In keeping with recent GOP trends, an effigy of "woke-ism" had been erected at the end of the field, with cameras capturing the scene from multiple angles. For the first time, Reagan didn't need to be "on." Eva was amused. Through rigorous practice, he'd regained his ability to project his voice and command a room with ease. However, a side effect of the vocal training was the disappearance of the meek voice he'd initially adopted. His casual speech now had a different, more assertive quality. The anxiety and shame associated with his feminine persona had largely subsided, replaced by a familiar arrogance and entitlement. The quiet little girl begging for acceptance had transformed into a formidable presence, a true "Karen" who would make short work of any cashier or waiter unfortunate enough to cross her path. On stage, Reagan sounded like Scarlett Johansson rallying her team against a supervillain. Off stage, he resembled Leah Michele berating a stagehand over a lukewarm latte.

The location was set. Reagan was handed ear protectors and a bolt-action rifle. The director barked instructions, "Okay, Reagan Sweetheart, face the camera, say the line, and then turn and take the shot. Easy enough?"

Reagan nodded, mentally vowing to never hire the director again for using such a juvenile term. His smile remained unwavering. When the slate dropped and action was called, he proudly declared, "My name is Reagan Esen Demir, and I approve this message," before turning and squeezing the trigger.

The bullet missed the target by a wide margin, exploding a few branches in the distance.

"Cut!" the director shouted. "Let's try that again. She made a weird face. She's holding the gun like it's made of snails, or she's about to break a nail or something. Reset, please."

Reagan repeated the line, delivering it flawlessly. But again, the target remained unscathed. Apparently, no one had considered firearms training. It became painfully obvious that despite his machismo he'd never held a firearm before.

The next three hours were a comedy of errors. Reagan faltered, his confidence crumbling. At one point, he hesitated before firing, raising the rifle towards the onlookers. The on-set expert, a man in a comically large cowboy hat, gently lowered the barrel and removed the rifle from his grasp, saying, "Woah, little lady, easy does it."

Exhausted, the director finally declared, "Fuck it, we'll do it in post," dismissing everyone and leaving the effigy untouched.

"Good god, that was a long day," Reagan complained as he slid into the limousine beside Eva, too embarrassed to mention his dismal performance.

Fortunately, his campaign manager had other matters on her mind. As she buckled her seatbelt, she reminded him, "We have one more stop to make. Don't forget, the doctor is staying open late for you. That procedure is tonight. That's why you took the week off, remember?"

“Oh right!” Reagan exclaimed, looking forward to a few days out of heels. “I completely forgot to be honest. There’s just been a lot going on, as you know.” He exhaled his stress, the restricting corset that aided his feminine shape no longer feeling like it was cutting in half after a month of wearing it. “You took care of all that. The surgeon knows all this is just for show, right?”

“Absolutely. You go in there, sign some forms, sit in a room for a little while, and you’re all done. The doctor is paid off, the paperwork will make it appear that you are actually getting surgery and the rest is up to everyone else.”

“That sounds amazing.” He was already dreaming of the foot massager sitting beneath his arm chair. His old dress shoes fit him perfectly and that meant once they were broken in they didn’t bother him at all. Since he started wearing high heels, whether they were broken in or not he had found the device to be a worthy investment.

A few hours later the two were back in Orlando, Reagan was in the private surgery center the doctor Eva had been meeting with worked from. The little room was actually quite nice, especially in comparison to public facilities, with a free selection of movies, and what basically amounted to room service equivalent to that of a five-star hotel. It almost seemed like a waste to the man, given his stay shouldn’t have been very long.

After signing the forms, a nurse came in with a paper gown, and said, “You’ve got to change before we can get started. Just put your things in this bag, and we’ll store them for you. No jewelry, no makeup. Wash your face too please, and the doctor should be in to see you in just a little bit. Go ahead and take this before I leave though, please.”

“What is it?” he asked, eyeballing the little blue pill.

“Just something to help with nerves.” she answered.

“Nerves.” He repeated the word with a smile. Something for his nerves would have been extremely helpful over the previous month, but he didn’t dare risk being impaired in public, should he say something the young lady he was presenting himself as shouldn’t.

Thinking of the pill as a bit of a treat, Reagan accepted. His mind drifted back to a past time, old escapades with Xanax in college. Eva must have been giving him permission to cut loose one last time before the campaign season really took off, and they’d be on the road most every week. The nurse left, and he leaned back into the bed, and after a little bit of time wasted playing on his phone, he found himself lost, staring up at the popcorn ceiling, as the background noise of the world slowly melted away. He’d lost so much weight that the **** were hitting him far harder than they used to.

A few minutes later the nurse reentered the room, and began chastising him for not changing, or washing his face, but quickly realized her patient was already long gone. She sighed, this clearly not being her first time dealing with such nonsense, and helped the slightly larger mess of a human strip, even removing Reagan’s corset for the first time in a few days, when he audibly moaned. After a lot of limp body, weird mumbling, and one very clear, “You’re pretty” she had her patient disrobed, and laid back in bed, her clothes bagged up.

“You’re very pretty too, Miss Demir.” The nurse said, while she helped remove his makeup.

One hand holding Reagan’s head in place, his eyes drifted across the nurse's jaw line, lingering on her lips. “Hmmm.” He let out the sound of contentment before a thought bubbled up. “Where’s Doctor Baker?” Reagan managed to ask, somehow in a complete, understandable sentence, realizing he had yet to see the bribed physician.

“He’s out sick,” the nurse explained, “but Doctor Humphrey is here, and he’s been helping girls like you for over twenty years. I promise, you’re in good hands.”

‘Trannies have been around for twenty years’” Reagan thought briefly before suddenly realizing just what was going on, but before he could give his voice to his thoughts, he felt a little pin prick in his arm. “Hey!” Reagan squealed, projecting his practiced feminine voice.

“Hello yourself.” A slightly overweight man in his mid-sixties stepped into the room, assuming his patient was addressing him. Seeing the nurse recapping a needle, he moved to the bedside. "I'd normally like to sit and speak with you, but my colleague left detailed notes, and with your schedule, we need to proceed quickly." Judging by his patient's appearance, he guessed she was in her late twenties, perhaps even younger.

"Noooo." Reagan shook his head, his mind feeling clouded. "We paid… Baker." Between the pill and the injection, it was a struggle to keep his eyes open, let alone form coherent sentences. He needed to get up and leave. This wasn't supposed to happen.

Gently pushing his patient back onto the bed, Dr. Humphrey said, "Nothing to worry about, Miss Demir. Just count backward from ten for me." He noticed Reagan’s anxiety rising and understood the unexpected change of doctors could be unsettling.

"Noo..." Reagan mumbled, struggling to resist.

"That's right," Dr. Humphrey soothed, patting her hand. "Nothing to worry about."

When Reagan closed his eyes, Dr. Humphrey nodded to the nurse. It was time to move the patient to the operating room.