Bored and Blackmailed

A sister shares her favorite girly activities with her brother whether he wants to or not.

Author's Note: This story is one that, in a unique twist, was inspired by a TG caption series I did over on DeviantArt (https://www.deviantart.com/vthunder42/gallery/75400278/bored-and-blackmailed), which was itself inspired by a concept for a prose story that I've had in my head for just about as long as I've had Summering in Femininity (https://www.tgstorytime.com/viewstory.php?sid=5985) up there, I could just never work out how to develop it past the initial concept, and once I did the caption series, I had the urge to bring my original vision to life, which is what this story is. Enjoy!

It was shaping up to be a normal, run of the mill day for siblings Dennis and Kylie Stevens. As it was the middle of summer, they were spending their day lounging about their house while their parents were at work. As it was a rainy day, they were spending the day inside.

Kylie strolled up to her older brother’s room and poked her head inside. A loud boom of thunder rang throughout the house, causing Kylie to jump. Dennis didn’t seem to notice it, since he had a pair of headphones on his head as he played a loud shooter game on his TV. Dennis’ room was about what one would expect, relatively messy, with a pile of dirty clothes near the closet, some posters depicting sports stars, and sci-fi fantasy movies on the wall and a TV on one wall with the bed situated on the other, which is where Dennis was sitting.

“Yes, eat it!” Dennis exclaimed as he sat back and took his headphones off to scratch his ears.

“Hey!” Kylie knocked on the door frame.

“Hey, what’s up?” Dennis turned around.

“I was wondering, do you wanna maybe watch a movie together or something?” Kylie asked.

“Maybe another time, I’m in the middle of an important part of the game, I’ve been trying to get here for weeks!” Dennis put his headset back on, turning back to the video game.

“Oh, okay…” Kylie dejectedly walked back to her room.

Kylie sat on her bed, idly scrolling through her phone messages, with several messages explaining how several of her friends were unavailable to hang out due to a variety of circumstances. Kylie sighed and laid back onto her bed.

Just then, a loud crack of thunder boomed through the house, and the lights immediately turned off. Kylie sat up in bed just as the lights returned.

“Aw, dammit!” Dennis shouted from the other room.

Kylie rushed out of her room and ran toward Dennis’, where he was quickly emerging from the door.

“Is something wrong? What happened?” Kylie asked.

“The power went out right before I was about to finish the level… Figures…” Dennis replied.

“Maybe it’s a sign that the universe doesn’t want you to finish that level today…”

“Well then, the universe can shove it, because once everything reboots, I’m doing it!”

Kylie just rolled her eyes and walked downstairs towards the kitchen. Several minutes later, as she was pouring herself a glass of soda, she heard Dennis shouting from the top of the stairs.

“Kylie!”

“Yeah?” Kylie shouted back.

“Can you check the router for me? My game isn’t connecting to the internet!” Dennis shouted.

“Got it!” Kylie replied.

Kylie headed into the family room, where the router was situated and started to look at the router. While she was very adept with technology, when the router went out, it was usually Dennis’ department, so she didn’t know what to look for. She scrunched her face as she tried to figure out what was wrong with it.

“Dennis! How many lights is the router supposed to have?”

“Four! How many are there?”

“None!”

After exhausting every troubleshooting method he knew, all of which failed, Dennis gave up and called their internet service provider, and once the fifteen minute call was over, Dennis sighed and hung up the phone.

“So? What happened?” Kylie asked.

“Apparently the power surge from the storm fried the router, they have to send someone out to replace it.” Dennis replied.

“That doesn’t sound too bad.”

“They’re not able to get someone out here until the hours of one and three… tomorrow.”

“That still doesn’t sound so bad.”

“It’s just annoying… it means I can’t play my game until then.”

“You need the internet to play your game? I didn’t hear you talking to anyone...”

“It’s one of those games that, even though I’m playing alone, it requires an internet connection to run, it’s really dumb.”

“Oh no, you might actually have to do something other than sit in front of a TV, how dreadful!” Kylie put her forearm on her forehead in mock concern.

“I’m glad you find this all so amusing…” Dennis walked away, heading for his room.

Half an hour later, Dennis was bored out of his skull. His limited connection to the internet on his phone was useless because of their data cap, and the only video game he wanted to play was non-functioning. He considered his options and came to only one conclusion, he should go check in on Kylie, surely she was just as bored as he was.

“Hey…” Dennis knocked on Kylie’s doorframe, poking his head into her room.

Kylie’s room was similarly predictable, Kylie was a very girly girl, and so her room was very girly. Pink walls, a vanity with cosmetics and jewelry strewn about it, a closet overflowing with skirts and dresses and various different types of shoes. At this particular moment, Kylie was sitting on her bed, flipping through a magazine.

“Hey!” Kylie closed the magazine and sat up. “What’s up?”

“You said earlier that you wanted to watch a movie? I guess I’m free now.” Dennis said.

“You’re finally bored enough to want to hang out with me?” Kylie smirked.

“No… Well… Yeah, there’s nothing to do!”

Kylie knew Dennis was right, as the rain continued to beat down on every window of the house, the siblings only had each other for entertainment.

“Let’s watch it down in the living room, the TV is bigger.” Kylie got up off her bed. “Here, go set it up, I’ll be right down.”

Kylie handed Dennis a DVD case, for a film Dennis had heard of, an adaptation for a book that Dennis had never read, since it was geared towards girls, so it was never on his radar. Still, it beat doing nothing.

Dennis headed downstairs to set the movie up, while Kylie grabbed some items off of her vanity, stuffing them into the pockets of her pink-striped pajama bottoms. She quickly went downstairs and sat down on the couch, sitting on one armrest as Dennis took the other. Dennis started the movie, and the two began watching.

For the most part, the movie was entertaining, certainly entertaining enough to warrant the awards that it had garnered. Halfway through the film, Kylie began to empty her pockets of a nail file, some cotton balls, and a bottle of bright pink nail polish.

“What’s all that?” Dennis asked as the noise took his attention away from the movie.

“Just some nail stuff, I was gonna give myself a pedicure.”

“Neat…” Dennis turned back to the movie.

Soon, the movie was getting close to the denouement, and Dennis was invested in all the characters, so much so that he hadn’t noticed that not only had Kylie finished her pedicure, but had moved from her seat on the couch to the floor, at least until Kylie grabbed his foot.

“Hey!” Dennis pulled his foot back. “What are you doing?”

“Just looking… you know your nails are terrible.” Kylie grabbed the foot back. “Look how dirty these are…”

“So what? I’m a guy, we don’t worry about that.” Dennis said.

“Maybe you should…” Kylie sniffed, then made a disgusted face. “How about I give you a pedicure? Just like mine!”

“I think I’ll pass.” Dennis said.

“Come on, I’m bored, you’re bored, besides, no one has to know! Who knows, you might even like it.” Kylie insisted. “The movie’s almost over, unless you’ve got a better idea of what to do?”

Dennis frowned, he didn’t have any better ideas, but doing such a girly activity was an affront to his masculinity! As he looked down at his sister giving him her best puppy dog eyes, he sighed and relaxed his foot.

“Why not? As long as nobody knows, right?” Dennis mused.

“Right!” Kylie smiled as she got to work.

After several minutes of shaping and buffing, Kylie was satisfied and put down the nail file, only to pick up the bottle of pink polish that she’d used on her own toenails. She started to place cotton balls in between Dennis’ toes, but Dennis once again pulled his foot back.

“No way!” Dennis exclaimed. “I don’t mind the shaping, but I draw the line at nail polish!”

“But it’s part of the experience!” Kylie insisted.

“Well, does it have to be pink?” Dennis asked.

“Please? I don’t wanna go all the way back upstairs to find my clear coat, besides, nobody’ll see it, and I’ll remove it later.” Kylie started her puppy dog eyes once more.

“Okay, fine!” Dennis threw up his hands in surrender. He’d lived with Kylie long enough to know it’s better to placate her than to get into an argument. “But no one will know, right?”

“You have my word.” Kylie said.

As she painted her older brother’s toes, Kylie grabbed her phone a few times, making it look like she was texting, but in reality, she was taking photos of Dennis and his shiny pink toes as he watched the end of the movie. With the movie finished, she moved onto his other foot, and as she finished the final brush stroke, she sat back and admired her work on her brother’s newly groomed and polished toes.

“And there... we... go! Honestly, I gotta say, pink looks good on you, bro.” Kylie giggled.

“Are you finally done? I know I agreed to let you paint my toenails but what if Mom and Dad come home and see it?” Dennis made nervous glances towards the front door.

“Relax, they’re not due home for hours and by the time they get home it’ll be dry enough for you to wear socks.” Kylie said, screwing the cap back on the bottle.

“Socks? You said you’d take it off when you were done!” Dennis exclaimed.

“And ruin all my hard work right away? Come on! They’re not going to be getting the truck out to fix the internet for at least a day. We’ll be just as bored tomorrow, so I thought we could do something else. Ooh, maybe I could do your hair!” Kylie started imagining other activities.

“Nuh uh, I'm drawing the line there. I’m still not sure how you convinced me to do this.” Dennis crossed his arms.

“Because it feels nice! Besides, it’d be a shame if these photos I took ended up online once the Wi-Fi comes back…” Kylie turned her phone around, showing Dennis various photos that clearly showed him allowing Kylie to paint his toenails. “I bet both my friends and yours would be very interested in seeing these…”

“You wouldn’t dare!” Dennis attempted to reach for the phone.

“Are you willing to find out?” Kylie stepped back.

“Gimme that!” Dennis started to stand up, but Kylie pushed him back down.

“Bup, bup, bup! You don’t want to smudge them, otherwise I have to start all over again! Now, I’m thinking that I probably won’t send them to anyone… if you do a few things for me.” Kylie grinned evilly.

Dennis didn’t think that Kylie would actively do anything to hurt him, but then again, he couldn’t really be sure, they were siblings, and he cared about her, but they weren’t particularly close enough for Dennis to know how she’d act in this situation. He only had one option.

“...Fine, you can do my hair. Tomorrow.” Dennis said, firmly.

Kylie smiled and started swiping through her camera roll.

“Of course I could probably send one or two pictures out with data if I really wanted to…”

“Okay, you can do my hair now! Just keep those pictures to yourself!” Dennis pleaded. “Please!”

“Yay! And don’t worry, tomorrow won’t be that much worse… Oh, I wonder if we have a pair of heels in the house that’ll fit you!” Kylie started to skip towards the stairs. “Coming, dear sister?”

Dennis held his head low with shame as he stood up and followed Kylie upstairs. As he entered Kylie’s room, she motioned towards the chair in front of her vanity. Dennis complied and Kylie began to play with his hair.

“You’ve always had such great hair, I’ve always wanted to do something to it.” Kylie said.

Dennis’ hair was, like Kylie’s, long and blonde, but while Kylie had their mother’s straight hair, Dennis had gotten their father’s curly hair, so the longer it got, the more unruly it got, so he tended to keep it in a low ponytail. Kylie eagerly removed the hair tie and reached over to the vanity for her already plugged in hair straightener, but Dennis quickly grabbed her wrist.

“Hold on, this is a lot more permanent than nail polish.” Dennis said.

“Not really, if you wash your hair a few times it’ll pretty much go back to normal.” Kylie said. “Besides, you don’t really have a choice here.”

Dennis began to speak, but closed his mouth and scowled instead, releasing Kylie’s wrist. Before grabbing the straightener, she popped over to her bed and picked up the magazine she’d been reading before, handing it to Dennis.

“Here, read this, it’ll help keep your mind off it, and maybe you won’t interrupt me as much. Remember, the faster I’m done, the faster this is all over.” Kylie said.

Dennis nodded and idly flipped through the magazine, there wasn’t much of interest to him in it, pages advertising perfumes, clothing and shoes, a few articles, but even the pages with models on them didn’t really hold his attention. Kylie continued to straighten and brush her brother’s hair, making sure not to miss a single strand. Eventually, Dennis looked up at the mirror and gasped, seeing his curly locks were much longer when straightened, and his short ponytail had given way to hair that was far more similar to Kylie’s than he’d have liked.

“Looks great, right?” Kylie asked.

“I…” Dennis was surprised at how big a change occurred from just straightening his hair.

Truthfully, Dennis hadn’t been endowed with much in the way of facial hair, a quirk of genetics, since their father’s facial hair was perennially patchy as well. Before Kylie could do anything else however, the siblings heard a car outside, and moments later, the front door opened.

“Kids! We’re home!” their mother shouted from downstairs.

“We picked up dinner on the way, I hope you’re in the mood for pizza!” their father shouted.

“Be right down!” Kylie exclaimed, before handing Dennis back his hair tie. “Here you go.”

“Thanks…” Dennis muttered as he pulled his hair back into its familiar ponytail.

“Meet you downstairs, don’t forget socks.” Kylie joked as she headed out of the room.

Dennis headed back to his room and picked up a pair of socks that wouldn’t reveal his painted toenails, and headed downstairs for dinner. As they ate, they discussed their days, with Dennis and Kylie omitting particular details of their day.

“The internet’s out, a power surge fried the router, so the company is sending a truck out tomorrow to fix it.” Dennis said, in between bites.

“Oh dear, how did you kids get along without the internet?” their mother joked.

“It wasn’t easy, it was pretty boring. But Dennis and I watched a movie together.” Kylie said.

“That’s nice, I’m glad you’re doing things together.” their mother replied.

“Yeah, I figured without the internet you’d be at each other’s throats.” their father chuckled.

“Come on, Dad, we’re mature enough to handle ourselves, right, Dennis?” Kylie asked, winking at Dennis.

“R-right!” Dennis replied quickly.

Satisfied with that answer, the conversation soon turned to the rough day at the office that their father had, before dinner concluded and everyone went their separate ways for the night. If either of their parents had noticed Dennis’ hair, neither let on.

Before turning in for the night, Dennis passed Kylie’s room, spotting her digging through her closet. For what, Dennis didn’t stick around to find out, but it didn’t inspire him with confidence about what would happen the next morning. Dennis did make an attempt to find a bottle of nail polish remover, to at least remove the potential for further blackmail material, but it seemed that Kylie had already taken care of that, having anticipated Dennis’ idea.

As such, it took Dennis a long time to fall asleep as his mind raced, wondering just what Kylie had in store for him and just how he managed to get blackmailed by his younger sister.

The next morning, Dennis stirred awake as he felt something touching his foot. He sat up and pulled his foot back, allowing Kylie to pull off one of his socks.

“Wakey wakey, sleepyhead! It’s time to get ready for the day!” Kylie sang. “Mom just left, so it’s time to play!”

“Go away!” Dennis, squinting his eyes, kicked his foot towards Kylie, but she artfully dodged him.

“Well, if that’s how you want to be, I bet I can find a good use for these photos…” Kylie giggled.

Dennis’ eyes shot open and he attempted to make a grab for Kylie’s phone, but failed.

“No, don’t!” Dennis shouted, before sighing. “What do you want me to do?”

“I want you to take a shower. Use my shampoo and body wash. And my Nair, unless you want to try your luck with a razor.” Kylie said.

“Hold on, nail polish and hair straightening is one thing, but shaving my body? That’s too far!” Dennis said.

“Oh relax, hair grows back! Besides, it’s not like you’ve got that much leg hair anyway.”

Dennis rolled his eyes at that comment, much like his face, the combination of poor genetics and blonde coloring made it patchy at best.

“All right, fine. But can you promise you won’t do anything else drastic?” Dennis begged.

“I think that can be arranged.” Kylie smiled. “Now, ‘Denise’, it’s time for your shower. I’ve left my robe in there, once you’re finished, meet me back in my room and I’ll help you get dressed.”

Dennis did as he was told, going into the bathroom, where indeed, Kylie’s pink terrycloth robe was hanging prominently on the back of the door. He turned on the shower and stripped out of his clothes, his shiny pink toenails taunting him as a reminder of the fact that, at least until the internet came back, he was at Kylie’s mercy.

“Well, let’s get this over with…” Dennis stepped into the shower.

For the most part, the shower was fairly normal, just a different scent than his usual “Clean”, “Fresh” or “Sport” soaps, in this case it was a flowery lilac scent. Using the depilatory was a new experience, but once he read the instructions, Dennis knew how to use it. What really concerned Dennis was Kylie’s behavior. Sure, they were siblings and siblings do stuff to embarrass each other or mess with them, but he hadn’t known Kylie to be as devious as she currently was. A prank is one thing, blackmail is out of character…

Unfortunately, his ruminations were interrupted by a knock on the bathroom door.

“Hurry up, dear ‘sister’! I’ve got a big day planned!” Kylie shouted.

“I’ll be right out!” Dennis shouted back.

Dennis quickly finished up the shower and toweled off, shivering due to the lack of body hair combined with the cold linoleum floor of the bathroom. After drying off as best he could, Dennis put on the fluffy pink robe and opened the bathroom door, where Kylie was eagerly waiting.

“Don’t worry, you’re going to look great by the time I’m done!” Kylie grabbed her brother’s hand and dragged him into her room.

Kylie started digging around in her drawers, purely for show, Dennis knew that she’d have already chosen what he’d be wearing by now. As Dennis waited, he shivered again, reminding him of his shaved body.

“Can you hurry it up?” Dennis demanded.

“Ooh, someone’s excited to wear my clothes…” Kylie giggled. “Here, put these on, I’ll turn around.”

Kylie handed Dennis a matching bra and panty set, both pink, much to his chagrin. He turned them over in his hands.

“Is a bra really necessary?” Dennis asked.

“I dunno, is keeping those pictures a secret really necessary?” Kylie retorted.

“Touche…” Dennis sighed. “Turn around.”

Kylie complied and Dennis let the robe fall to the floor, before quickly putting on the unfamiliar undergarments. He fumbled with the bra, but soon figured out how to fasten it. The tricky part was getting himself stuffed into the panties, but with some effort, he figured out how to keep himself contained within them.

“All right, are you happy?” Dennis asked.

“Immensely!” Kylie replied. “Now, let’s see, I like this dress, but this skirt is cute and…”

After a few more minutes of hemming and hawing as Dennis stood in the center of Kylie’s room, with the padded bra providing the illusion of cleavage, which Dennis noted as he glanced in the mirror.

“Okay, okay, I’ve got your outfit right here.” Kylie presented Dennis with a bundle of clothing.

Dennis looked through the bundle, which consisted of a white tank top and a skirt adorned with multi-colored flowers. Dennis grumbled a bit, but only to hide his relief that she hadn’t chosen one of the formal dresses that he’d seen her wear in the past. Once he had gotten the high-waisted skirt and tank top on, he squirmed uncomfortably.

“Almost done…” Kylie grabbed some socks and stuffed them into the cups of the bra. “Perfect. Now, take a seat.”

Kylie motioned to the chair in front of the vanity, and Dennis sat down, sighing. With a blow dryer and brush in hand, Kylie made quick work of getting her brother’s hair into a similar style as it had been the previous day. Dennis watched, slightly in awe, as his wet stringy hair, which he usually didn’t do much with, transformed into soft, shiny locks that reached past his shoulders.

“You know, you’ve got really nice hair, it’s a shame you keep it tied up all the time…” Kylie muttered.

“I guess…” Dennis replied, but couldn’t help but silently agree with what his sister had said.

“Okay, and now for the fun part. Makeover time!” Kylie grabbed her makeup bag and started going to work before Dennis could object.

Dennis, already exhausted from his previous attempts to get Kylie to let up, decided to just let it happen, the sooner it did, the sooner it would be over, so while he wasn’t happy about it, he let Kylie apply a generous coating of gloss to his lips, a bit of blush to his cheeks, and some mascara to his eyelashes. Again, Dennis was thankful, since much like with the outfit, he’d expected a lot worse. While it wasn’t that dramatic, Dennis did realize that he had a lot more resemblance to Kylie than he’d thought previously, enhancing features they’d both inherited from their parents.

“One last thing…” Kylie approached Dennis with a pair of tweezers in hand, but Dennis quickly ducked out of the way. “Come on!”

“You said nothing permanent!” Dennis stood up and backed away from Kylie.

“I’m just going to clean them up a bit, or are you growing a unibrow on purpose?” Kylie motioned to the mirror.

Dennis got closer and looked at his face in the mirror, noticing a lot of stray hairs in between his eyebrows. It wasn’t something he’d ever noticed before, but now that he saw it, it was very noticeable.

“Okay, fine, but just the stray hairs.” Dennis sat down once more.

“Don’t worry, I know what I’m doing…” Kylie moved the tweezers back towards her brother’s face.

Unfortunately, Kylie was a tad overconfident in her abilities, so after plucking a few too many hairs from one eyebrow, she had to repeat the same on the other. Keeping Dennis from seeing the mirror, Kylie assured her brother.

“Don’t worry, it looks fine… mostly.” Kylie said.

“Mostly?” Dennis pushed Kylie out of the way to look in the mirror.

Dennis’ jaw dropped open as he saw that his eyebrows had been shaped into a very feminine style, something that could take weeks to grow back to normal.

“What the hell, Kylie?” Dennis demanded.

“I’m sorry, it was a mistake, but it’s fine, if they notice, I’ll tell Mom and Dad I did it as a prank while you were asleep and if you need to go out, you can just use an eyebrow pencil to fill it in!” Kylie responded, pulling out her phone. “Besides, even if it wasn’t a mistake, you’re in no position to argue…”

Dennis slumped back in the chair and sighed. He desperately wanted to take charge and demand the phone, after all, he was the older brother, but now that he’d let her take it this far… there wasn’t any turning back. He just had to let things happen from here.

“And now for accessories!” Kylie grabbed a few pieces of jewelry off her vanity and handed them to Dennis.

Dennis looked them over, a ring, a few bracelets, and a necklace with a pink crystal heart. Girly, but by far the least of his worries at this point. The ring and bracelets were simple, but the necklace took some work. As he fastened the necklace onto his neck, he spotted Kylie taking another photo.

“Lookin’ good, ‘sis’! I really like how your hair came out after I straightened it.” Kylie grinned.

“Yeah, sure, get your jokes in now, because once the internet is back, this is over! I don’t know how we managed to hide my hair from Mom and Dad, but you’ve gone way too far now!” Dennis whined.

“Looks like you know something I don’t, because I never said it’d be over when the internet was back, just that I can’t really post any photos until it’s back.”

“You said you wanted to do this because you were bored and we had nothing better to do!”

“And I didn’t realize how much fun it’d be, I might want to keep this up… that is if you don’t do exactly what I want without complaining.”

“...What do you want from me?”

“At the moment, I need some better photos, the lighting in here is terrible, I think the next step is to take the photoshoot outside.”

“Outside? But someone might see me!” Dennis’ heart started to race.

Dressing up like a girl and letting Kylie do what she wanted was one thing in the privacy of their home where no neighbors or passerbys might see. But out in the open? That was another matter entirely!

“And as long as you’re cooperative, no one will ever know who that mystery girl on the lawn is. If you don’t, I think my ‘sister’ might start having a burgeoning social media presence…”

Dennis opened his mouth to speak, but again, was completely speechless. After sputtering and stuttering for a minute, he just threw his arms up in frustration.

“Oh, and before we go, make sure to put on your shoes.” Kylie handed Dennis a pair of pink, open-toed pumps.

“Heels?” Dennis asked.

“Not only do they show off your pretty toenails, but they match, too!” Kylie smiled.

After putting on the unfamiliar heels and taking a few cursory steps, Dennis managed to get the hang of it, at least well enough to descend the stairs, while gripping the bannister tightly, and made his way towards the backyard.

While the previous day had been dark and stormy, the sun had finally emerged and there wasn’t a cloud in the sky. Dennis squinted as he emerged from the house.

“You should consider yourself lucky, I was going to make you pose on the lawn, but the grass is too wet and your heels would just sink, so we’ll have to stay closer to the house.” Kylie said.

“Small mercies…” Dennis muttered as he glanced around, ensuring nobody was in a position to see into the yard.

“All right, now stand there and I’ll tell you how to pose!” Kylie said.

For several minutes, as he stood against the wall of the house, Dennis was forced into a variety of poses and expressions by Kylie, including one where he was to hold the hem of the skirt with his fingertips.

“Yes! Just like that, hold the skirt like that, although it wouldn’t kill you to smile, you know.” Kylie instructed.

“Maybe I’d be more inclined to smile if I wasn’t being blackmailed! How much longer is this going to go on for anyway?” Dennis spat.

“I dunno, I guess until we get internet back, but we’ll see.” Kylie shrugged as she snapped another photo.

“Come on, you’ve had your fun, you made me shave my whole body, you plucked my eyebrows, I’m wearing a stuffed bra and a skirt, and you put makeup and jewelry on me. I think the game’s gotten old.”

“Old? I’m just getting started! It’s fun to have a sister around to do stuff with, way better than some boring brother who spends all his time in his room playing video games…” Kylie trailed off, a hint of sadness in her voice.

Dennis’ jaw dropped. The blackmail, her gleeful remarks as she forced him into the most embarrassing situation that he’d ever been in before, the threats, it was all because she felt he played video games too much? Dennis was confused, angry, and a whole bunch of other emotions that he couldn’t even process at the moment.

“Is that what this is about? You didn’t need to blackmail me if you wanted to just hang out!” Dennis exclaimed, louder than he intended.

“No, but you don’t like the same stuff as me, certainly not any of the girly stuff I like, face masks and pedicures and all that. Besides, you’d have said no when I asked.” Kylie pouted and crossed her arms.

“You don’t know that! You’ve never asked!” Dennis shouted.

“I do! All the time, and you’re always too busy in a raid or something like that!” Kylie shouted back.

“So you force me to dress like a girl by blackmailing me?” Dennis motioned towards himself. “That’s your idea of doing stuff together? You think this is what siblings do to each other? Embarrassing them in sadistic ways? Threatening to release photos that could ruin my reputation at school?”

“Sadistic? I’m sorry… I just wanted to have some fun…” Kylie frowned. “I wasn’t really going to post any of the pictures. I’d never do that...”

“Really?” Dennis’ anger evaporated in an instant as he saw tears starting to well in Kylie’s eyes.

“You can go ahead and get undressed, I’ll delete all the photos…” Kylie sniffed as she held back tears and ran into the house.

“Wait, Kylie!” Dennis shouted, trying to grab Kylie as she ran away. “Stop!”

Dennis, unused to the heels he was wearing, attempted to give chase, but was forced to take small, mincing steps to avoid face planting on the hard concrete. Once he got into the house, he took a few steps before clicking his tongue in annoyance, and sat down on the couch, reaching down to remove the inconvenient high heels from his feet. He massaged his foot for a moment before rushing upstairs to Kylie’s room.

Dennis took a moment to catch his breath and really thought back, trying to remember the last time he spent any time with Kylie that wasn’t just idle conversation at dinner or passing in the kitchen as they each made a snack. Dennis sighed as he realized that it had been a very long time… too long a time. Steeling himself up as much as he could in his feminine get-up, he knocked lightly on the door.

“Hey, Kylie?” Dennis called.

“Go away! That’s what you wanted right, for me to leave you alone?” Kylie shouted.

“Come on, Kylie, I just want to talk for a minute.” Dennis insisted.

“Fine…” Kylie opened her bedroom door slightly.

“Listen, I’m sorry I yelled at you. I was angry, but I get it now. I wasn’t being a particularly good brother, it’s no wonder that you felt you had to blackmail me to do anything with you…” Dennis said. “Besides, I didn’t hate everything you did as much as I said I did…”

“You’re just saying that to make me feel better!” Kylie began to slam the door, but Dennis pushed it back open.

“Wait! You were right yesterday, the pedicure did feel really good, I wouldn’t mind doing that again, minus the pink nail polish. You know, if you wanted to hang out together once I’m back in my regular clothes. But while I’m still dressed up like this… what else did you have planned for today?”

“Well, now that you ask…” Kylie grinned, not an evil grin, but a genuinely happy grin.

Once the burden of blackmail had been lifted, Dennis was far more receptive to Kylie’s activities, and they enjoyed a few hours of activities, some sisterly bonding like Kylie teaching Dennis how to paint nails, leaving the siblings with matching pink manicures, with Kylie using press-on nails for Dennis’ for easy removal later, and some just general hanging out, like cooking breakfast together. Dennis was far more comfortable in his new outfit, ditching the tight tank top and skirt for a pair of black shorts and a green collared button down sleeveless blouse. Even the uncomfortable heels had been replaced by a pair of Kylie’s sneakers that fit Dennis.

As Dennis munched on a piece of bacon and Kylie chattered on with her other plans for the day, they were both interrupted by the sound of the doorbell ringing. Dennis froze, and Kylie, noticing her brother’s discomfort, immediately shot up.

“I’ll get it!” Kylie ran to the front door and peeked out the window.

An older man in a uniform was standing there, carrying a box. Satisfied that it wasn’t one of either her or Dennis’ friends making an unannounced visit, Kylie reached for the doorknob.

“...Yes?” Kylie asked as she cracked open the door.

“I’m from ISP, we got a call that your router is broken? We’re here to replace it.” the man said, pointing to the logo on his breast pocket.

“Oh, of course! Come on in! ‘Denise’, show him where the router is!” Kylie shouted.

Dennis sheepishly nodded as he motioned for the worker to follow him. After checking the router and doing some routine checks of the system to ensure nothing else had failed, the worker installed the new router, and the internet light blinked on, like a beacon of hope.

“That should fix it, but feel free to call back if you have any further problems. Have a good day, young ladies.” the worker said as he wrote down something on his clipboard, before heading out of the house.

Kylie shut the door behind him, giggling at how her brother had been referred to as a ‘young lady’ by the worker. When she returned, she found Dennis had left the room. Kylie quickly realized the first place her brother would have gone. She bounded up the stairs and sure enough, Dennis was turning on his game console up in his room. Kylie gently knocked on his door frame.

“What are you smiling about, dear ‘sister’?” Kylie asked.

“The internet’s back! I can finally play my game again!” Dennis exclaimed. “I’m gonna kick that level’s ass!”

“Oh… I guess you’ll want to change back into your own clothes, right?” Kylie said sadly, looking at her feet.

“I could… although this outfit is pretty comfortable. Way better than that skirt and heels. I wouldn’t mind wearing it a little bit longer.” Dennis shrugged. “And you said something earlier about face masks? That might be fun to do, since Mom and Dad aren’t gonna be home for a while yet.”

“I’ll go get them! Ooh, and there’s this rom-com I’ve been meaning to watch… And-” Kylie excitedly started to turn around.

“Or, or, or…” Dennis exclaimed. “You could be my player 2!”

“Huh?” Kylie scrunched her face in confusion.

“I mean, you’ve spent the last two days sharing all of your favorite stuff with me, I think it’s about time I return the favor.” Dennis smiled, holding out a controller.

“Nothing would make me happier, bro.” Kylie smiled and took the controller from Dennis’ manicured hand.

“Same here, sis.” Dennis motioned for Kylie to sit down. “Now, the secret to this level is…”

The End