The $1000 Genderswap Prank: How I Became the Office Bombshell… for Nothing

A Tempting Offer

Company Spirit Week starts next week with the much-appreciated Genderswap Day! Come in dressed in the outfit of the opposite sex. Each day, the company employees would vote with the winner getting 1000$. Something about showcasing the company spirit.

Jim smirked as he looked over the email from the company. Company Spirit weeks always felt like such a silly event. Jim was tempted to blow this off like he had all the ones before until he saw the mention of 1000$.

That would be a nice little chunk of change to add to his savings for a computer. 1000$ a day could go into some much-needed car repairs, not that he thought he would win every day.

The Easy Win

Still, there was the temptation to skip this one ‘Genderswap Day.’ There would be heckling over this for a while from the ones who skipped it. Heck, if Martin showed up dressed, Jim knew he would rub it in Martina’s face all day long.

In reality, most guys would skip it, and most girls probably wouldn’t bother either. There was not much they could do. Why not throw on some pants? Most of them wore pants to work every day already.

Which meant there wouldn’t be much competition.

The number 1000 seemed to grow larger on the page. This would be the easiest day to win. He could pull off some heels or a dress. His hand went up to his hair and felt its length. It was getting longer. He had been saving up for the computer for a while, which meant skipping a haircut once or twice.

Enter Chelsea

“I wonder if Chelsea would have any clothes that fit me,” he mused. He grabbed his phone and scrolled to his sister’s phone number. She lived close by and they had a monthly get-together to stay in touch.

Things had gotten rough between them. Stemming from when he had dated and broken up with her best friend. They had patched it back up. Besides, it was Mindy who broke it off with him.

Finally with a shrug, he figured to shoot his shot and called her up. She answered on the third ring with a bright and chipper, “What’s up, bro?”

Despite the short notice—only a day—Chelsea seemed to almost take some delight in the offer. If he won, she was going to take a cut of the winnings, but even to Jim, that seemed fair. If he lost, she would shrug her shoulders and enjoy having a sister for the day, as she said.

Crossing the Threshold

On Sunday, he showed up at her doorstep. Nerves and second thoughts fill his head. But the 1000-dollar incentive kept him motivated. Besides, Chelsea’s genuine excitement at the prospect seemed to have wormed its way into him as well.

Maybe being a girl for a day wouldn’t be too bad.

The plan was for him to come over today. They would do a lot of the heavy lifting today. He would spend the night so they could get an early start tomorrow morning. If there was one thing women loved doing, it was telling men how long it takes to get ready.

“Shave, Missy!”

“What’s up, little sis!?” Chelsea greeted me enthusiastically as she swung open the door. Jim cringed slightly at her volume. She still lived in an apartment, and he was still a guy she was greeting.

“Save the enthusiasm for when I am not sporting a five o’clock shadow,” he stated, rubbing his incoming beard.

“You’re shaving that off first.”

“Can’t I go as a bearded lady?” he said in jest.

“That’s a cruel stereotype, and no, you’re going as a blonde bombshell. We’re in this to win it!”

“Heck, if you can make me hotter than Jennifer in accounting, I’m in.”

“Ooh, trying to impress somebody?”

“Yeah, Jennifer in accounting. I hear she’s a lesbian.”

“Pig.”

It was the light-hearted banter that could only come from brother and sister. They got along well and knew nothing was off-limits, but there was plenty of time to have fun and catch up. They had business to get done.

“Seriously, though,” Chelsea stated, flicking a hand out and pointing down the hall, “Shave.” She paused and added, “And I mean everywhere. I got a fresh pack of razors for you to use.”

Pretending to be agonized, Jim overreacted dramatically as he made his way to the bathroom. “I’m pretty sure I can just get away with my face. Just give me a sweater and some girly pants or something.” He began his usual face-shaving ritual.

“Nope, not pants, which means no leg hair!”

“Why not?” he moaned. Nonetheless, he began to shave away what little hair he had, “Shouldn’t I be a boss babe or whatever and pick my fit.”

“First off, I’m the boss, babe, and I vote dress. Second of all, you have made more than one comment that the women in your office could be more womanly. Show off more legs, right?”

“When I’m drunk or hanging with the guys, sure.”

“So, you are going to be the most womanly woman ever woman.”

“I don’t think that’s a real sentence,” Jim commented. He had finished up his face and looked down at the rest of his body, hoping to be given a chance to talk his way out of this.

“And this isn’t a vote. Dress, heels, make-up,” Chelsea said, counting it off on her fingers. Then she grabbed the bathroom door and closed it shut, “and shaved legs. So strip and shave, missy.”

The Makeover Begins

With a sigh, Jim stripped off his pants and spread a generous amount of shaving cream up and down his legs. This was still within his expectations. Chelsea was a bit of a perfectionist, after all.

This was also why Jim wasn’t surprised when Chelsea stood in front of the door. She was already prepped, with her makeup at the ready. “I need to find your style!”

Various chit-chats flowed between them as Chelsea worked, although Chelsea still carried most of the conversation. Whenever Jim tried to talk for too long, she shushed him, insisting she needed him to stay still while she applied another concoction.

Finally, she felt confident and stepped back. “Yup, that’s it. You’re definitely autumn.”

Jim could feel a layer of makeup on his face and could taste some kind of raspberry lip balm on his lips. Every slight flutter of his eyelids made him aware of the thick black mascara coating them.

Dressing the Part

“I laid out some possible outfits for you in the guest room,” Chelsea stated, pointing in its direction. “Go and try them on.”

Without missing a beat, Jim wandered into the room, where they saw several outfits laid out on the bed. Yet his eyes remained transfixed instead on two other items. Two large skin-colored blobs lay resting on top ofa lacy black bra.

Chelsea was a perfectionist, after all.

After struggling with the bra for a few seconds, Jim finally realized another way. He could close the band in the front and then spin it around. Slipping his arms through the straps was the last step.

Well, the last step was settling the two jiggling silicone orbs into their place on his chest. They were a bit cold as they came to rest against his skin, but they were also heavy. He could feel their weight through the straps on his shoulder. Idly, he wondered if this is what it always felt like for women. No wonder they hated bras.

A pair of matching panties were slipped on next. They glided up his bare legs, and he could feel the satin sensation of them trace their form along his body. These were so much more comfortable, even if there wasn’t a whole lot of room for him in them.

Then came the outfits; Chelsea wasn’t lying about not allowing him any pants or shorts. There were dresses and skirts. A few of them, Jim was certain, weren’t workplace appropriate. He had to wonder if Chelsea really intended on him wearing the wedding dress.

Jim tried on dozens of outfits ranging from sporty to casual to a little too girly. Even the wedding dress was chosen with some more prodding from Chelsea. Jim finally settled on what he was pretty confident would be his outfit of choice for tomorrow.

One Last Tweak

“Looks like I’m all ready,” Jim stated, checking himself in the mirror that evening. “The boobs are a bit big. Did you have to get them this big?”

With a shrug and a mischievous smirk, Chelsea stated, “I got a smaller set. But I wanted to see if you would just use the big ones without questioning it, and you did, ya big-breasted bimbo!”

Jim reached over and threw the towel at his sister, “Give me the smaller ones.”

“You made your choice!” Chelsea sang as the towel slapped against her face.

Showtime

The next day, Jim found himself riding shotgun in Chelsea’s car. While it was unlikely, he’d have car troubles and have to flash his ID. Chelsea had talked him into letting her drive him. Although not without another quip about how Jim could flash other assets to get out of a ticket.

He had gone in on the stereotypical office lady look: a tight pencil skirt and white blouse with frills down the center. His hair was just long enough to be tied up into a neat bun. Tight satin and sheer pantyhose encased his legs. He found them to be as comfortable and delightful as the panties from yesterday.

The small black pumps were hard to walk in, but he would be sitting behind a computer for most of his day, so a few minutes of discomfort were well worth the bonus to his femininity they provided.

His sister had also won out on the bigger breast size. Jim could swear she was hitting every bump on the way in on purpose so that they would bounce and jiggle.

“I’ll be back to pick you up when I’m done with work,” Chelsea stated as Jim got out of the car and onto uneasy feet. “Best of luck; I am sure Jennifer in accounting will be jealous.”

The Elevator Ride of Shame

Jim steeled himself with a deep breath, blushing as he realized doing so made him puff out his considerable chest. His hunch had turned out correct, as none of the greeters were dressed, nor was anyone else in the lobby unless they were more of a perfectionist than his sister.

Hitting the going-up elevator button was a bit of a task with the extra-inch-long fake nails Chelsea had glued on his fingers. Thankfully, someone else needed the elevator, so Jim was able to take that ride up, too.

The Twist

The sight upon arriving on his office floor shocked Jim. He wasn’t expecting everyone to take part, only a few. Yet it looked like no one was. The first person he saw was actually Martin, who stood there with a big dopey smile on his face as he locked eyes with Jim.

Childhood friends are constant pranksters, and they always take it a little bit too far. Jim could feel a pit in his stomach before Martin even said the words.

“April Fools!”