The Costume Contest: A Halloween Tale! (Patreon)

The Costume Contest

“I’m sick of Rick making me dress up as a slut every Halloween,” Darla said, tottering on her stiletto heels in the women’s room at Excelucorps. This year, he’d made her dress as a sexy witch.

“Tell me about it,” Kelly said, joining Darla at the mirror, mussing her hair. “At least you didn’t have to dress up as a prostitute, and, of course, Jose dresses up as a pimp. I wonder what message that sends to everyone.”

“And all the guys think since I’m dressed like this, they can make all kinds of lewd comments. How am I supposed to have people respect me when they see me dressed up like Elphaba’s slutty cousin?”

“And you can’t complain to HR,” Kelly said.

“Like Frank would do anything.”

Just then, they were interrupted by a hoarse, scratchy laugh coming from one of the stalls. “Ha.Ha. Hee. Hee. Ho. Ho.” It sounded more like someone pretending to laugh than a real laugh. Purple smoke began to pour out from beneath the stall door, and they heard the latch turn.

“What the hell?”

The door to the stall swung open and Kristava, the creepy tech girl, stood there, vape pipe in hand, and she blew a cloud of purple smoke into the air. She had a rat’s nest of wiry black hair, and thick mascara giving her racoon eyes. This was not a costume, but her everyday look.

“You fucking scared me!” Darla said.

“Creep,” Kelly said. Everyone hated Kristava. “And, uh, by the way, vaping in the ladies’ room is a major violation of company policy.”

“Well, you call me the rude names, but I helps you anyways.” She walked up to the mirror and shoved her way between Kelly and Darla. “How about we make them dress as sexy sluts next year?”

“Yeah, right.” Kelly said.

“We can do this together. I will prove it to you.”

“How?”

Kristava pulled them closer and began to whisper.

Chapter 2

The next Monday, Kelly found herself busily editing a report Jose had written– full of errors, as usual– when the man himself walked in the door to the office– late, as usual. Having mostly forgotten about the weird conversation with Kristava, she glanced up, meaning to say her usual good morning, and froze as she stared at Jose’s eyebrows.

He’d clearly had them done. They were not too thin, but they had been plucked into a classic arch, the edges neatly defined, and dyed a darker shade. They looked more like a woman’s sculpted brows than a man’s. “Good morning?” She said.

“You got that report ready?” Jose said.

“Working on it.” Kelly couldn’t resist asking. “Did you get your brows done?”

“What? Oh, yeah,” Jose said, running a finger along the line of his sleek, sculpted brows. “What’ya think? I wasn’t really sure, but I just had this impulse.”

“I think they look great,” Kelly said.

Jose smiled. “Thanks!” He seemed genuinely pleased.

Kelly texted Darla. “He got his brows done.”

Darla texted right back. “Rick, too. Looks cute.”

Kelly: Let’s do this.

Darla: Yup.

Later that day, as planned, Darla knocked on Rick’s door and peeked into his office.

“What’s up?” He said. He had his putter in his hands, had been working on his golf game, as usual.

“I have some big news,” Darla said, sneaking into the office, pulling the door closed. “It’s about the partnership.”

Rick’s eyes lit up. Jankowski, one of the founding partners, was set to retire in the next year, and the competition to replace him was fierce. He’d learned long ago that secretaries knew things a lot sooner than other people, and Darla, good little worker that she was, had buddied up to Jankowski’s secretary. “Hit me,” he said, gesturing Darla toward the couch.

The two sat down. “You know how Jankowski likes to ask offbeat questions when interviewing potential new hires?”

“Yeah,” Rick said, chuckling. “Catch ‘em off guard. Get them away from their pre-planned answers to obvious questions.”

“Test their character,” Darla added.

“Yeah? So?”

“I heard from his secretary he plans to do the same thing with the new partner, only it’s going to be based on who has the best costume for next year’s Halloween party.” As she spoke, Darla used the ring Kristava had given her to catch the light from the windows and flash it back into Rick’s eyes. She could see them growing glassy, distant. “He wants to see who will go all in, commit, get out of his comfort zone.”

“That sounds like him.”

“The catch is, next year, the theme is crossdressing.”

“Crossdressing?” Rick said, his speech becoming thick, slightly slurred. There was a hint of alarm in his voice.

“Men dress as women, women as men,” Darla said, smirking.

“I won’t dress up as a woman,” Rick said, shaking his head.

“You told me before you would love to,” Darla said, moving her ring, flashing the light in his eyes.

“I did?”

“Of course. Because you’re so secure in your manhood.”

“I did say that,” Rick said. “Yes.”

“And you want to be partner, right? You told me you would do anything to make partner.”

“I did say that,” Rick agreed, now totally under Darla’s spell.

“You even told me you had the perfect idea for a costume. Jankowski has all those pictures of angels in his office, so you always thought you would be a sexy angel.”

“I’m going to be a sexy angel,” Rick mumbled.

****

Kelly, meanwhile, was working the same spell on Jose, but he was fighting her. “A slutty nurse?” He mumbled, shaking his head. “No. I can’t. I’d… no one would respect me after that.”

Very true, Kelly thought, but she kept flashing her ring in Jose’s dull, drooping eyes. “They will respect you even more,” Kelly said. “You’ll be a partner.”

Jose kept shaking his head, fighting with all his will against an idea every instinct told him was a huge mistake. “I can’t.”

“Well, then I guess Rick will win.”

“Rick?” Jose said, anger now flashing in his eyes. The two hated each other.

“He’s going all in, and that will show Jankowski he has more courage,” Kelly said, then waited.

Jose sat there for a time, blank, staring, then said, “I’m gonna be a slutty nurse.”

Chapter Three

“Tell me about your goals,” Anna said. One of the top personal trainers in the city, she wore a candy-colored pair of yoga pants and sports bra that showed off her tone, fit body. She was hot as hell, and Rick struggled to keep the slight boner forming in his pants from getting bigger and embarrassing him. It was totally humiliating for him to have to tell this beautiful woman his goals, but he wanted that partnership, and there was no way he was letting Jose win.

‘I, um.. Well, this may sound a little weird, but for a variety of reasons, I need to go to next year’s Halloween party as a… er…”

“There’s no judgment here,” Anna said, giggling and tossing her hair.

“I need to go as an angel,” Rich blurted out, dropping his eyes in shame as his boner vanished. “A– girl– angel.”

“I love it,” Anna said. “Okay, so you need an angel’s body.” She looked Rick over. “I’m gonna help you achieve your goals, and the first thing you need to be is skinny.”

“Skinny?”

“Let’s get started!”

Kelly and Darla made a point to schedule their bosses at the gym at the same time. Rick and Jose found themselves running on treadmills next to each other, each one trying to outdo the other. When it started, they were both lumpy, muscular men. Rick climbed onto his treadmill as Jose did the same. “Hoping to shed some muscle?” Jose said.

“Not hoping,” Rick answered, starting up his machine. “When I set my mind to something, I do it.”

“We’ll see,” Jose said. “I bet a year from now I’m waaaay skinnier than you. I’m more of a man than you, Rick.”

“Please. I’m going to work harder in my dreams to earn the curves I need to win this contest. Besides, Darla tells me I have great bone structure, and she is sure I’ll be super pretty.”

“I’m going to be so much prettier than you,” Jose said. “It won’t even be close.”

Committed to massive amounts of cardio and crash diets, they grew thinner and thinner. The hormones their secretaries were slipping into their drinks along with Kristava’s magic brought about other changes, and it was only a few months later that the now lean, leggy men approached their treadmills, slitting their eyes at each other as they checked out the other’s body. They each now wore nylon short shorts that showed off their smooth, round, coltish legs. Both men now shaved their legs daily. Their tank tops showed off their slender arms and small, round shoulders, while also drawing tight against the firm round swell of their budding, pre-teen breasts.

Thanks to their diets and regular facials, they had bright, glowing skin.

Skinny bitch, Rick though, checking Jose out, feeling jealous and threatened. He thinks he’s so cute.

Jose was suffering similar feminine rage at the sight of Rick and his tight, ever more curvy body. Tossing their noses in the air, the men climbed onto their treadmills and, tightening their ponytails, started to run, their ponytails swaying and bouncing.

Jose came into the office, his long hair tied back in a tight bun. On Kelly’s suggestion, he’d begun wearing women’s suits, since they fit his developing body better. She’d assured him no one would notice. In truth, everyone had noticed. He and Rick were the talk of the office as they grew both skinner and more curvy, wearing clothes that were obviously tailored for women.

“Any important messages?” Jose asked, planting one hand on his rounding hips while examining the nails on the other. He’d been growing them out for weeks. Kelly had noticed he was speaking in a higher voice.

“There’s an inquiry from Power Corps you should probably look at, sweetie.”

Jose rolled his eyes. “I am so tired of mothering them,” he said, dramatically, turning on his office flats and walking into his office, his laptop bag, which looked a lot like a purse, slung over his shoulder. Kelly smirked. His walk was coming along nicely: heel to toe, with a precious, feminine swing to his widening hips.

At the gym, Anna watched as Rick, sweating, did squats. Now that she’d gotten him nice and skinny, she was helping him develop a plump, tight ass. Each time he rose from a squat, his b cups bounced. Anna saw him wince and put a hand gingerly to his chest.

“Breasts hurt?” Anna said.

“My chest aches when I work out,” Rick said, still in denial about the fetching swell of his budding breasts.

“You need a bra,” Anna said.

“A bra?” Rick said, stopping his squats and staring at her in horror.

“Your girls need support. Come on. We have them in the shop.”

“I don’t–”

“Come on, Angel. You’ll thank me later.”

A blushing and humiliated Rick followed Anna to the sports shop. Fawn, who worked the desk, smiled brightly as the two approached. “Hey, Angel,” she said. Everyone had just started calling Rick Angel. “What’s up?”

Anna put her arm around Rick’s small shoulders. “Angel is here to get her first bra!” Anna announced.

Fawn clapped. “Congratulations!”

Rick thought he would die. ‘It’s just for support,” he mumbled.

“No kidding,” Fawn said. “That’s why all us girls wear them.”

“That and they get men hard,” Anna added, giving Rick’s shoulder a squeeze.

Moments later, Rick followed Anna back to the gym floor, the bright pink straps of his sports bra obvious beneath the slender straps of his racerback tank top. “Let’s do some squat jumps,” Anna said.

Rick did, though his legs and glutes were burning. He needed an Angel body if he wanted to be partner. As he leapt in the air and landed, his breasts jiggled, but much less. The bra really did hold them. It felt like it was hugging them, protecting them.

“Well?” Anna said.

Rick smiled. “You were right,” he said, jumping, his long ponytail bouncing as he strained to get the firm, lifted ass he needed.

“You should really wear a bra all the time to avoid your boobs getting saggy, stretch marks,” Anna said as Rick jumped.

“Stretch marks”?

“I’ll help you pick some out after your workout.”

Chapter Four

Rick and Jose approached their treadmills. Halloween was only a couple months away. Rick’s eyes dropped from Jose’s pretty face to his tits. While Rick had found himself fitted with a pretty pair of perky b cups, Jose had kept blossoming, and his own sports bra now lifted and displayed the swell of his full, womanly D cups. Seeing Rick checking him out, he pretended to fuss with the tie on his ponytail, but it was really just an excuse to arch his back and push his breasts forward.

“Angel,” Jose sassed, voice oozing with feminine contempt.

“Josie,” Rick sassed back, using the name Jose had begun to us at the gym as he’d become utterly unconvincing as a man.

“You’re cute,” Jose said as he got on his treadmill. “But you’re not pretty.”

“Really?” Rick shot back. “Then how come all the guys here are always checking me out?”

“Humph!”

Humph!”

Rick and Jose’s evenings became mirror images of each other as they say at newly purchased makeup tables, practicing their makeup for Halloween, wiping it off and putting it on again. They filed their long nails, and painted them with Barely There nail polish, let down their hair and brushed it until it shone. After practicing their makeup and doing their nails, it was time to practice walking and sitting in heels. Jose stepped into the high heeled boots he would be wearing as a slutty nurse, while Rick strapped on the angel heeled stilettos Darla had chosen for his costume. Then it was walking back and forth, back and forth, heel to toe, heel to toe. Sitting gracefully, knees together, standing, knees together… heel to toe… heel to toe…

One night as Halloween approached, Rick, wearing just a bra and panties, finished painting his lips, smiled at himself from different angles, then sighed. He was sure Jose was sexier than him, hotter. Had he done all this for nothing?

Darla could tell right away that Rick was upset. He’d become more emotional over the last year, his head swimming in estrogen, and less skillful at hiding his emotions. He looked really cute in his women’s clothes, and it was obvious he’d taken to wearing push up bras that lifted and thrust his breasts forward. He’d taken to braiding his hair, and thick, lustrous candy braid hung over his right shoulder.

“Something wrong, honey?” Darla asked in the empathetic voice she used whenever inviting one of her besties to spill.

“Let’s talk in my office,” Rick said.

Rick got them each a bottle of Perrier, and they sat on the couch. On Darla’s suggestion, he’d started to have fresh flowers delivered every day, and his office decor had been shifted so his walls now displayed painting of flowers and sunsets and all sorts of girly things to help him “internalize his angel.”

Rick sat, knees together. “I’m worried I’m going to lose the contest,” Rick said. “Jose is– well, he’s hotter than me!”

“Why would you say that?” Darla asked, trying not to laugh at the fact her once manly boss was now worried about being pretty.

“His boobs!” Rick said. “He’s like— womp– out to here!” He said, holding his hands way out in front of his chest. Then, he opened his coat to show his firm, pretty B cups. “Look?”

Once more, it was all Darla could do to keep from laughing. Rick was actually jealous of Jose’s bust? Too perfect. “You have great tits,” Darla said, patting Rick’s knee.

“Really?”

“Bigger isn’t always better.”

“Hmmmn. I know guys always say that, or some do, but…”

“You always liked girls with big tits.”

“I did,” Rick admitted. Then, he got to the point. “Should I get a boob job?”

It was so, so tempting for Darla to say yes, to fit her boss with a bouncy pair of D cups and let him deal with the backaches for the rest of his life. But that wasn’t the plan she’d made for him. In fact, she’d wanted him to be a petite woman and to spend the rest of his life feeling inadequate because he didn’t have bigger tits. No, she had another fate in store for her little angel.

“I know what you can do to put yourself over the edge,” she said, taking Rick’s braid in her hands and toying with it.

“What?” Rick asked.

“Well, I happen to know, Jankowski has a thing for blondes.”

“Make an appointment,” Rick said. “As soon as possible.”

It was a very different Rick who came strutting confidently into the office the next day, blonde hair sparkling, a bright, pretty smile on his face.

Chapter Five

It was the day before Halloween when Rick and Jose met at the treadmills for the final time. They sized each other up, each impressed with the other man’s skin, hair, body. Each man had had his ears pierced, little studs sparkling each time he moved his head.

“I didn’t think you’d be man enough to go through with this,” Jose said, adjusting his bra straps.

Rick tossed his braids. “I thought you’d be too big of a pussy to stick with it,” he said. “I guess all the other guys in the office didn’t have the guts They’re going to look so ugly dressed as women.”

“It’s just you or me for the big promotion.”

“May the best man win,” Rick said.

“May the best man win.” With that, they shared a hug, their soft breasts pressing into each other, the smell of their shampoo and perfume swirling in the air around them.

A guy stopped. “You girls gonna kiss?” He asked.

Rick and Jose turned on him. “Pig!” They squeaked, their voices shrill and full of feminine rage. Men!

***

The night of the Halloween party, Darla and Kelly convinced their victims to come to the office and change into their costumes at work, so as to avoid the risk of spilling anything on them. Each showed up wearing a woman’s casual tracksuit, and soon Darla and Kelly watched as the totally feminized men sat carefully putting on their makeup, doing their hair, and then stepped into their dresses. They were both super nervous, worrying about every little thing from their hair down to their toes.

The sound of music started in the main room, and the buzzing of voices. “You need to make a big entrance,” Kelly told Jose as she straightened the little, old-fashioned nurse’s hat pinned into his hair. “Darla and I will announce you, then you come strutting out of the office like a Victoria’s Secret supermodel. Jankowski will be so impressed.”

“You’re sure the collar isn’t too much?” Jose asked, glancing in the mirror at his dog collar, which read, “Anal Costs Extra.”

“It’s perfect,” Kelly assured him.

“Thanks for all you’ve done,” Jose said, giving Kelly a hug. “You’re such a good friend.”

Snickering, Kelly and Darla went out into the main room. Everyone was there– the guys were dressed as MMA fighters, pirates, cops and vampires. The only ones not dressed up were the partners, who considered it undignified. They sat together in the corner, drinking, watching, trying to decide if they wanted to try and take any of the girls home. The girls were all slutty somethings, and they were enticing.

“Attention! Attention!” Kelly shouted.

“Attention!” Darla shouted, even louder. The buzz died down, and all eyes turned to the secretaries. “This year, our bosses, Rick and Jose, decided to do something really special for their Halloween costumes,” Darla said.

“We think you are all going to be very impressed! Maestro?”

On cue, the DJ fired up an old school stripper vamp.

“Come on out, girls!” Darla and Kelly shouted in unison.

The doors to their offices flew open, and Rick and Jose came strutting out of their offices, smiling brightly, tossing their hair… they were each about ten steps into the room when their steps faltered, and their smiles melted away.

“What the hell?” Rick said in his little girl voice as he noticed no one else was cross-dressed.

“I don’t understand,” Jose gasped in his own high-pitched, breathy voice.

Even as they started to realize they’d been fooled, the spells that had made them expect and accept their changes faded away, and suddenly the same old Rick and the same old Jose found himself propped on heels, wearing a dress and sporting dangerous curves. They looked down in horror at the swell of their breasts.

Everyone stared, and the two men wilted, blushed. Everyone had seen the ways they were changing, but no one had seen them or expected to see them dressed like– this.

And then Garmen, the office clown, shouted, “Them’s two fine ass bitches!”

Everyone laughed. Then, Kelly and Darla started clapping, and then everyone was clapping. The DJ went back to playing dance pop. Darla and Kelly grabbed their bosses’ hands and dragged them to the center of the dance floor. “What the hell have you done to me?” Jose hissed to Kelly, annoyed at the tacky, sticky feel of his lipstick.

“Improved you,” Kelly said, giggling as she patted him on his smooth, soft cheek. “You better just pretend like you did all this on purpose, or you’ll look even dumber.”

Rick, dancing with his angel wings, was equally furious. “I look like a fool in front of everyone,” he whispered, though he kept a smile on his face. “What am I supposed to do now?”

“Brazen it out unless you want the bosses to know your secretary made you look like a dumbass.”

Rick and Jose decided they had no choice. They were men, and they weren’t going to run away in tears. They’d gotten played, but they would just act like it was their idea all along.

The night was hell. Guys kept hitting on them, grabbing their asses. One guy pushed Rick against a copier and tried to kiss him. Another came up behind Jose and grabbed his tits.

The women, most of whom they had harassed over the years, teased them mercilessly, telling them how sexy they looked, assuring them they had great tits and fine asses.

When the party finally started to break up, both Rick and Jose declined numerous requests from men to “come over to my place for a nightcap” and then, fighting their way past the pestering handsy men, finally retreated to their offices, collapsing and at long last allowing the tears to roll down their cheeks as they wept. They were both destroyed, had no future at the company.

And they were both now trapped in the bodies of women.

Kristava, who’d come to the party dressed as a French Mime, approached Kelly and Darla. “Do you find satisfaction?” She asked.

“Um, yeah,” Darla said.

“So much satisfaction.”

“Well, tomorrow when they wake up,” she said and then made an oval shape with her hands. “Vaginas.”

Darla, Kristeva and Kelly went out on the deck and passed the vape pipe around. “Did they really deserve this? Was it too much?” Kelly asked, looking up at the full moon.

Darla shrugged. “Who cares?” she said. ‘It was fun.”

‘You make them hot bitches,” Kristava said. “They never have to buy drink again. They should thank you.”

At that, all three women began to laugh.