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Chapter 20
by
Nicegent42
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Chapter 20
Chapter 20
A little over an hour later Reagan was still sitting at his desk. Nose deep in both his office computer, and his laptop, his attention darted back and forth between them. On his desktop played a video, The Perfect Half UP, for his continued girly training. He didn’t think his hair was long enough for it, but Victorian rag curls seemed easier than any of the contraptions Eva had subjected him to, achieved by twisting hair around strips of fabric and sleeping with them in. It wasn’t the most captivating use of his time, but he had never been one to shy away from research, or at least hadn’t until said research was a makeup tutorial for hooded eyes.
On his laptop Reagan had his little sister’s Instagram account pulled up, and he was trying to catch a glimpse into her life. Clicking on one of the photos, the image was of Callie with a brunette girl around the same age. The pair stood on a pier overlooking the ocean while eating soft serve ice cream. Callie had strawberry, while the pretty young woman at her side had a twist of both vanilla and chocolate. In the image his sister wore a white bathing suit coverup that reminded him of a medieval tunic, accented with thread and wooden toggles. Her friend had a towel draped around her neck, her feminine assets prominently displayed in her deep blue bikini. Noticing the tags at the bottom of the screen, Reagan was finally able to grasp the scene. #Maddy, #DaytonaBeach, #DateDay.
“Well, at least my little sister has good taste.” Reagan said to himself, looking at who he believed was his sister's girlfriend. He couldn’t help but think it unfair that he had to date a man instead of the sexy little thing. Suddenly each of the three screens on his desk flickered. A cursory inspection showed him everything still plugged in, and better equipped to use the machine than fix it, Reagan threw his hands in the air.
They didn’t have an IT guy on staff. It just wasn’t needed every day, so they kept a small company on retainer for big issues when they cropped up. Other than that he would just ask Ryan and Eva to look into little things.
His old college friend had some sort of computer degree, or she minored in it - he wasn’t sure. Ryan was helpful and capable while also struggling to say no to things, making him the de facto tech support.
The flicker of the screens only grew worse after a few seconds, but just as suddenly as the distortion started, the images became clear once more, only now they displayed a light blue background with a cartoonish image at the center - one of a blue, sharp-tooth koala wearing an eyepatch with the outline of a skull depicted upon it.
“No!” Reagan shrieked, as the animated image giggled soundlessly.
The last time he had seen the mascot of the hacker group, his life had been turned upside down. They were the reason he was **** to keep spinning a lie that had grown to encompass every aspect of his life.
“No… fuck you… no, NO!”
While the logo stayed put on his monitors, the screen on Reagan’s laptop faded to blue, before scrolling text appeared.
His anger boiling his blood, Reagan read “Hello Reagan, you look much better now that you resemble your true self.”
Wordlessly, Reagan whipped his head from side to side, his muscles clenching.
‘This can’t be happening again! They… they…’
Anger could be useful, it could be a call to action, but when with no outlet, it was an anchor around Reagan’s neck. His mind stuttered as the trauma of the past few months came crashing down on him. His money had been stolen, made to look like he donated it all. His political base had fled, as he was transformed into something he looked down upon.
“I’m not…”
The text on the screen continued, “No? Then you have been lying to everybody. We can help
bring light to the darkness - truth to the masses. You have been bad Reagan… VERY bad.”
Reading that, Reagan’s eyes snapped up to the door as he took a few steps toward it. He needed to get Eva, but was stopped in his tracks at the sight of the next threat.
“Stay put or we’ll empty your bank account again.”
Swallowing hard, Reagan’s eyes searched the room, half expecting to see cameras, but he
found none. “You can see me?”
“Laptops have cameras, beautiful. We would say to use your brain, but it would be best if you
didn’t worry your pretty little head with thoughts right now.”
Pressing his hand to his chest, Reagan could feel his heart thumping rapidly, the jibe flying over his head as he tried to restrain his panic.
“Wh.. What do you want?”
They never asked for anything before, but he hoped they might be reasoned with, though it might have already been too late. They had the leverage and **** to do an incalculable amount of damage.
“Today doesn’t have to hurt. In fact you might even enjoy it. All you have to do is follow directions. Step one: Only speak when we tell you to. Say this: Please don’t tell everyone the truth about me. I promise to be a good girl.”
Reagan considered shouting for Eva, he considered running out of the room screaming, and he even considered falling back down into his seat and crying. He was reliving his worst trauma, when only that day he’d begun coming to grips with how normal his life seemed.
“I will be good… please don’t tell…” he began before the scrolling text changed.
“Say it as we tell you, this is your first warning and only warning.”
Letting out a breath, Reagan repeated the phrase verbatim, “Please don’t tell everyone the truth about me. I… promise to be a good girl.” his own practiced feminine voice accompanied by a whimper.
“She can learn! I now know you can speak, but can that pretty little head follow more complicated directions? Remove your bra, but leave your pretty blouse on. Hold it up to the camera and smile.”
The switch in personal pronouns went unnoticed by Reagan’s overloaded brain, as he rushed to comply. Untucking the blouse he reached under to unclasp the ivory bra, before struggling to slide his arms through his sleeves, and straps. It took a few tries before he was able to perform the task. He had seen girls perform the feat, but never imagined it would be a skill he’d be **** to master at proverbial gunpoint, though he never had expected to have breasts of his own either.
“There, happy now?!” he spat, holding the bra up in front of him with a **** smile that betrayed his sour mood.
“We have so few rules, and yet you already violated them, but we knew you were a bad girl. It looks like one Elias Arnoult is scheduled to meet you for lunch. How about we make a video for him?”
Driving in his car, Elias tapped his thumb on his steering wheel, as he listened to Darknet Diaries, a podcast on real life stories of the internet that took a dark turn. The host was speaking about ransomware, and how it was the cause of some companies to crumble. It was cut short by a notification from a message from his girlfriend.
A smile formed on his lips, as he reached down to take his phone to see what she sent. The man was certainly entitled enough to text while driving. What he found was a video, its still image being that of Reah’s bra, the one she left in that morning.
Pressing play, he saw the still image come to life, the hand tossing her bra to her desk, though the toss failed. As the article of clothing fell to the ground it still made Elias’ smile grow wider. Pulling to the side of the road, enthralled by what was unfolding, he continued to watch as the camera shifted so he could see the beautiful face of the woman he loved. While she wore a bright smile, he felt something was off, considering how out of character the performance was. His best guess was that she might be a little nervous.
“I can’t wait to see you.” Elias heard the woman coo, as she began to pout, her blue eyes gaining his full attention as she batted hermlashes. “I need you… I need you because I have been naughty.”
The phrasing caught the man’s attention. She’d never spoken to him like this before, and it had him intrigued.
“I need to be punished. Can you come punish me? Mmmm, I will see you soon!”
Taking a deep breath, Elias watched as his girl bit her bottom lip and purred into the camera. He didn’t know what she meant exactly, but she was obviously horny, and now he was too. Shifting the car back into drive, he made an effort to make up the time lost watching the video.
Slowing his pace after jogging through the parking lot, Elias attempted to remain calm, as he stepped into the frantic campaign office. With a nod and wave to some intern, he walked past without a word, not checking in like most visitors. He made his way to the closed office, only to find Reagan sitting at her desk with a none-too-happy expression on her face.
“Got here as fast as I could.” Elias said, pausing, afraid he might have missed his window, but was pleased when her face lit up the moment she noticed him.
Reagan had been sitting at his desk, legs crossed, foot bouncing, as he stared daggers at his laptop. The hacker hadn’t yet relinquished control of the system, insisting he not only stay in place, but also notify his assistant he was not to be disturbed by anybody, save one man. It cut off any hope of escape. He couldn’t argue, the words on the screen laid out exactly what was expected.
The fear from before gave way to a burning anger raging beneath the surface. He dreamed of things he would do to the people of this group if he ever got his hands on them, but they had him not only by the balls, but even worse, by the pocketbook.
All he could do was sit there and stew while he waited for his literal male lover to arrive, a man who could no longer rationalize away as just a fake boyfriend.
When Elias made his way into his office wearing the same dark suit, white button-up, and dark burgundy tie Reagan had seen him in that morning, unconsciously Reagan’s painted lips formed a smile. It only grew from there as he began the demanded performance.
Standing up from his chair, Reagan pushed it away with one foot while hooking a finger to beckon him closer. “I’ve been naughty. Can you please help me learn to be better?”

Doing as instructed, Elias felt a little uneasy, remembering the first time his love had done something similar, that time she demanded that he let her give him a blow job while someone else watched. “Punish you?”
Reagan **** a coy smile, nodding before bending forward, as he reached back to hike his calf-length skirt up to his waist. “When I’m naughty, I need a spanking.” he said, cringing at the elementary school theater performance.
The words on the screen in front of him changed once more. “DO IT…”
Apprehensively entering uncharted territory, Elias pressed his hand to Reah’s exposed rear, the raised skirt exposing her purple lacy panties. “Yeah? How naughty have you been?”
‘For fucks sake, just do it.’
Reagan's thoughts mirrored the words on the screen, though their intent was different. His tormentor wished him to suffer - to shatter what was little was left of his crumbling masculinity. Reagan just wanted to get it over with. He didn’t know what else to do, other than to comply. What he wasn’t going to do was cry out like some wimp. He knew that under all the makeup, and feminine finery beat the heart of a proud man.
“Very.” That was when the first slap came down. It wasn’t hard, but jarring enough without any actual pain. “Haard-er.”
Reagan tried to remain calm and in control, but the single word came out staggered. Across the room, sat in that black shadow box, was the memento from his father, something he had kept on his person almost every day, and now it was imprisoned behind that thin piece of glass. The words engraved on it made him feel like the deceased man could not only see his skirt-wearing son beg to be spanked, but his corpse was turning over in his grave because of it. As he read the inscription, Reagan clenched his jaw, while he waited for Elias, the man he was intimate with, to spank him again like a disobedient housewife from the nineteen-forties.
Raising an eyebrow, hearing his woman’s arousal, Elias did as she commanded. His queen knew what she wanted and he loved that she didn’t play games. She wanted it - she demanded it, and he was going to give her exactly what she desired. Hand in the air, he brought it down hard, a sting spreading across the palm of his hand. He wasn’t trying to bruise her, but if his love wanted a little pain, he was happy to provide it.
“Such a naughty girl.” he said, before connecting for a third and then a fourth.
“Fuck…!” The word slipped out of Reagan’s mouth, the pain reminding him of Elias’ pelvis doing the very same thing the night before. He endured the ****, but by the eighth slap he had to make an effort to not pull away. Still, he needed seven more to meet the demands placed upon him. “More!”
Tugging at his tie, Elias removed it before giving Reah another slap. “You like that don’t you?”
The way she cursed signaled how much the act was turning her on, and to his own surprise, it was doing the same for him. When she didn’t respond, Elias took off his jacket, tossing it to the side, as he started to unbutton his shirt.
“Naughty girl, you were asked a question.”
When the next few slaps came, Reagan couldn’t help but yelp. He had been told specific things he was allowed to say, but couldn’t help pleading for it to end despite his promise to himself. “Please…”
“Yeah?” Elias responded.
The love of his life had moved from demanding to begging, causing his member to twitch. He found it interesting that a new experience could excite him so much. Elias pulled down the hiked up skirt, letting it drop to the floor with the purple panties along with it.
Resting one hand on Reah’s ass, he let his touch linger along the red welts rising up. Feeling as turned on as he was, Elias forgot the fact that they were in a building full of people, busily going about their day. As he finished disrobing, he laid down another slap, and then another.
“AH!” Reagan gasped, biting his bottom lip, as he shook his head. “One more, just one more.”
“Mm, mm, mmm.” Elias ran his fingers over his growing member as he gave the final spanking.
As he tried to stand up straight, Reagan found himself pushed back down. It wasn’t an incredibly powerful gesture, but it caught him completely by surprise.
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Political Hack
Chapter 1
Reagan Esen Demir is running to get elected for a Senate seat, unfortunately for him a hacker has not only hacked his campaign website, but practically his entire life. They made it look like he was coming out as trans as punishment for his anti LGBTQ agenda.
Updated on Mar 11, 2025
by Nicegent42
Created on Mar 1, 2025
by Nicegent42
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