Chapter 1: Bet You Can't Do a 360 Treflip?

The summer heat beat down on the concrete as Taylor adjusted his oversized Frasher T-shirt. Sweat dampened the fur on his slender frame. His baggy jeans hung low on his narrow hips, the fabric worn in areas from countless hours spent at the skatepark. The white-mottled tabby cat was thin for his height. He was lean with messy fur.

The bet was simple. The latest in a string of dares the pair had made over the course of their friendship. The terms were: any trick Cole did, Taylor had to match. If the cat failed to land even a single one then he had to be Cole's slave for the rest of the day. If he succeeded then Cole had to do whatever he wanted. The stakes were high and the two had spent the entire day showing each other up at the skatepark. One whole day of back and forth, each one attempting to be the victor.

Cole had started off easy, the black lab landing a smooth well practiced kickflip. Taylor matched it on his first attempt. Grinning, Cole upped the ante with a heelflip, but Taylor landed it smoothly after only a couple of tries.

“That all ya got?" Taylor had boasted.

Cole's only response has been turning his hat around.

As they progressed, the tricks became more complex. Cole pulled off a varial flip, his board spinning and flipping simultaneously. Taylor, determined not to be outdone, attempted the same trick repeatedly until he stuck the landing, much to Cole's surprise.

The two friends fed off each other's energy, their skills, honed over their summers together being tested with each challenge. Cole landed a 360 flip on flat ground, and Taylor, after several tries and a few falls, managed to replicate it, albeit a bit wobbly.

Sensing he needed to do something truly impressive to win their impromptu contest, Cole eyed the stairs leading down to the parking lot. With a deep breath, he positioned himself at the top, his heart racing.

"Watch this," Cole called out, a mix of excitement and nervousness in his voice.

Taylor watched in awe as Cole kicked off, gaining speed and approached the edge of the stairs. Just as he reached the precipice, Cole popped his board, his feet moving in a complex pattern. The board spun beneath him, completing a full 360-degree rotation while also flipping - a treflip down the stairs.

Time seemed to slow as Cole and his board sailed through the air. Taylor held his breath, certain his friend was about to eat concrete. But somehow, against all odds, Cole's feet found the board just as it neared the ground. He landed with a heavy thud, his knees bending deeply to absorb the impact. For a heart-stopping moment, it looked like he might lose balance, but Cole threw his arms out and managed to ride away, disbelief written all over his face.

"Holy shit, dude!" Taylor exclaimed, rushing down to meet him. "That was insane!"

Cole, still processing what he'd just accomplished, broke into a wide grin.

"I can't believe I actually landed that," he said, breathless and exhilarated.

The black furred labrador kicked his board up and leaned against a wall, catching his breath.

"What the hell even was that!" Taylor said, still in disbelief at what he had just witnessed.

As Cole basked in his achievement, Taylor's competitive spirit flared. He knew he had to match Cole's trick to win their day-long contest. His ears flicked as he softly bit his tongue in concentration. He needed to land a 360 treflip down the small stairs. But he hesitated, Taylor had never attempted such a trick before.

Taylor took a moment to steady himself. As he did he looked over his best friend, still disbelieving what he had just witnessed.

Cole was almost Taylor's complete opposite. The dog was taller and more muscular, his fur neatly brushed. Cole's tail wagged slowly behind him as he smirked over at Taylor. The dog smugly leaned against a wall with his arms crossed.

A horn sounded over the skatepark's PA system. The sound being the 15-minute closing announcement. This was it, Taylor thought to himself. This was his last chance to wipe that stupid cocky look off of Cove's face. Yet still Taylor hesitated. Taylor dropped his board and skated back to the top of the stairs.

The cat had enough time for one last attempt before the skatepark closed. All that they had done already that day had been exhausting, but in a good way. They had pushed each other hard and both had the bruises to prove it. But this was going to be his moment. Then Cole was his slave for the rest of the day. And Taylor was already imagining the things he'd make Cole do.

Taylor kicked off and quickly picked up speed. The cat's feet felt steady on his board as the wind rustled his fur. Taylor steadied his stance and then popped his board up as he hit the top of the stairs. The cat took off and flew through the air, his board rotated around underneath him in a perfect 360. But as he went to land, his board slipped away at a crucial moment and the cat tumbled to the ground, rolling head over heels.

Taylor lay on his back and blinked up at the sky. A quick mental check confirmed that the only injury was to his pride. Cole walked into his field of vision and stood there grinning, his muscular frame casting a shadow over Taylor. Taylor sighed. The two of them had been inseparable since their freshman year of high school. They had spent countless afternoons perfecting tricks and sharing dreams. That had to count for something right? Maybe Cole would go easy on him for old times' sake. Taylor thought wistfully.

In truth, Taylor was taking the loss harder than he normally would. With college looming, this lost bet felt like more than just a silly dare. The bet felt like the end of their childhood. In a few weeks, maybe a little over a month, they would both have to deal with their futures. Then who knew if they would even see each other again? They would probably live in different cities, live vastly different lives.

Cole would be off attending some Ivy League college out of state, and Taylor — Well, Taylor didn't know what he was going to do. His dad was kicking him out at the end of summer, that much was clear. He had some money saved up from his previous part-time job at the skate shop, but it wouldn't be enough for an apartment. Maybe he could crash on someone's couch for a while, but that wasn't a long-term solution. He'd have to get a full-time job and find a place in town.

Cole reached down and grabbed Taylor's hand pulling the cat up onto his feet. The sudden motion snapped Taylor out of his thoughts. Taylor frowned as Cole easily lifted him up, his paw dwarfed by the labrador's. The cat's fur bristled slightly at the contact, a mixture of embarrassment from his fall and something else he couldn't quite name.

"A bet's a bet," Taylor sighed, his whiskers drooping as he brushed himself off and looked up at Cole. The labrador's cocky grin had softened into something more affectionate, his tail wagging slowly behind him.

"Don't look so glum Bro," Cole chuckled, slinging an arm around Taylor's shoulders. "I promise I won't make you do anything too terrible."

Taylor's ears flicked back as he rolled his eyes. "Yeah, yeah. Let's just get this over with. What's my punishment, oh mighty victor?"

Cole's eyes sparkled with mischief as he pretended to consider. "Oh, just wait. I have something special in mind ..."

As he and Cole started walking, Taylor found his mind continuing to wander. He couldn't help but marvel at how different they were - Cole, confident and assured of his future, and himself, uncertain and adrift. Cole was popular with everyone he met. He was handsome, muscular, and smart. The Labrador could literally be hanging out at any number of places besides here with him.

On the other paw, Taylor had always been a loner who barely talked with anyone. The cat wouldn't call himself butch or macho, but he had decent muscles. He wasn't gorgeous, but he didn't think he was ugly. That being said, Taylor had always been small for his age. It led him to be rather insecure at times. Those insecurities may also be the reason why he could be a bit of an asshole to the people around him. Yet somehow, he and Cole had been best friends for years.

"Earth to Taylor," Cole's voice broke through his reverie. "You still with me, buddy?"

Taylor blinked, focusing back on Cole's face. "Sorry, just... thinking." Taylor smirked, “how about we go hit up a movie or something?"

Cole's eyes narrowed as he scanned Taylors face. “You're not trying to get out of our bet are you?"

“Nooo…" Taylor said defensively as he tried to avoid eye contact with the lab.

Cole shook his head slowly, not believing the cat for a moment. “Uh-huh well good. You know the deal, a bet is a bet is a bet."

“Yeah. I know. I just think maybe we are getting kinda old for silly bets." Taylor smiled as he bumped his shoulder against Cove's side.

“Silly bets? Yeah silly now that you're the one that has to pay up." Cole said with a scoff," I'm still banned from S-mart! And aisle 5 still smells like olive oil last I heard."

Tayler laughed under his breath while cringing. That had been an epic bet, one for the ages. So— Cole did have a point. Plus a bet was a bet was a bet. It was a sacred bro code tenant.

Even though Taylor had no real intention of backing out of their deal, he could tell Cole was getting a little exasperated. The cat slowly shook his head.

“Relax dude, I was just kidding. Just thinking of stuff we could do to kill time tonight. Ya know— if you want to hang out late."

Cole's expression softened, his paw reaching over and squeezed Taylor's shoulder gently. "Hey, I know things have been tough with your dad and everything. If you need a place to crash..."

Taylor's throat tightened. This was one of Cole's superpowers, the ability to see right through him and cut straight to the point. Sometimes Taylor wondered if Cole knew him better than he even knew himself.

"Thanks, Cole. I... I might take you up on that."

For a moment, they stood there, an unspoken weight hanging between them.

Then Cole cleared his throat, his usual bravado returning.

"Alright, enough moping. Time for you to pay up, loser," Cole grinned, tugging Taylor forward towards his car.

As they resumed walking, their boards tucked under their arms, Taylor couldn't shake the feeling that things between them were changing. Their usual banter felt different somehow, each moment and interaction felt numbered. Was this the last time they would hang out at the skatepark? Was it the last time they would make silly bets? Those thoughts followed him as the two made their way towards the parking lot.

Cole's car was an old beater, held together more by hope than mechanics. As they climbed in, the familiar scent of fast food and skateboard wax enveloped them. How many afternoons had they spent in this car, driving aimlessly and dreaming about the future? Now that that future was right around the corner, Taylor wasn't sure he wanted to be a part of it anymore.

"So, where are we going, and what do I have to do?" Taylor asked, trying to keep his voice light despite his inner turmoil. He wanted to think of anything else besides the questions that kept lurking in his mind.

Cole started the engine, that mischievous glint back in his eyes.

"You'll see," was all Cole said in a teasing voice.

“Mmmmm…" was Taylors only response. The cat could only roll his eyes so many times in one day. It was obvious that Cole was going to draw out the suspense as long as he could. So he'd just have to ignore the lab and not give him the satisfaction of a reaction.

As they pulled out of the skatepark, Taylor gazed out the window, watching their small town roll by. He thought about all the summers they'd spent here, all the memories they'd made. The car hummed beneath them as Cole drove, his paw occasionally brushing Taylor's leg as he shifted gears. Each touch innocent and comforting, a reminder of how comfortable the two were with one another.

"You know," Cole said softly, his eyes fixed on the road ahead, "I'm really gonna miss this. Miss being here with you. Kinda seems like the end of an era- ya know?"

Taylor's heart skipped a beat at Cole's words.

"Yeah," he managed to reply, his voice barely above a whisper. "I know what ya mean..."

As they drove the tension in the car grew thicker. The space between the two was filled with unspoken words. Taylor found himself stealing glances over at Cole. Occasionally he would catch glimpses of the lab looking back over at him. In an effort to break the silence, Taylor turned on the car stereo and hit play on the tape deck. Their favorite band, Mouse Rat, started playing from a cassette he had given Cole for his birthday months ago. They must have both listened to it a hundred times.

The music filled the space and put both of them at ease. Taylor nodded his head to the punk rock songs while Cole started singing along to the lyrics. Cole would purposely get the words wrong and Taylor just knew it was to mess with him. Every purposefully missed word would cause Taylor to glare over at his friend. The lab would then just stick his tongue out and sing louder. This only made Taylor smile and roll his eyes despite himself.

The truth was Taylor loved these moments with Cole. Their time together in these moments was safe and comforting. As Taylor looked over at his friend as he sang, he noticed the way Cole's fur caught the sunlight, the strong line of his jaw, the gentle curve of his smile. He was going to miss these moments even though Cole couldn't sing for shit.

As Cole pulled into the driveway of his house, the familiar sight of his childhood friend's home brought a strange mix of comfort and nervous energy to Taylor. The two of them had spent countless afternoons here, hanging out in Cole's room, playing video games, or just talking about life. Cole led the way inside, tossing his keys onto the kitchen counter before heading up the stairs to his room. Taylor followed, his skateboard tucked under one arm.

Cole's room was exactly as it had always been. The walls were plastered with skate posters, a stack of magazines sat in the corner, and a faint smell of incense lingered in the air. An old TV set on an old dresser with an even older K.E.S. game system sat against the far wall and a few bean bags were in the middle of the floor. It was a space that felt more like home than his actual home.

Taylor flopped onto Cole's bed, sprawling out dramatically. “Alright," he said with a sigh. “Enough suspense, let's get this over with. What do I have to do for losing the bet?"

Cole smirked, leaning against his desk with his arms crossed. “Oh, don't worry. I'll think of something."

Taylor rolled his eyes. “Come on, dude. Just tell me already."

Cole tapped his chin thoughtfully before pointing at Taylor. “Alright, first thing—go get me some water."

Taylor groaned but got up anyway, trudging down to the kitchen to grab a glass of water. When he returned and handed it to Cole, the dog took a long sip before grinning mischievously.

“Good job. Now take off my shoes."

Taylor blinked. “Seriously?"

“A bet's a bet," Cole said with a shrug.

Muttering under his breath, Taylor knelt down and untied Cole's sneakers, tugging them off and tossing them aside. He stood up, brushing off his hands. “Ugh- man, your feet stink. There. Happy?"

Cole's grin widened. “Not yet. Stand on one leg and pat your head."

Taylor stared at him incredulously. “You've got to be kidding me."

“Nope," Cole said cheerfully. “Do it."

With an exaggerated sigh, Taylor complied, balancing on one leg and patting his head while glaring at Cole. The dog burst out laughing, nearly spilling his water.

As Taylor finished patting his head while balancing on one leg, he dropped back onto both feet with an exaggerated sigh. "You're such an idiot," he muttered, shaking his head at Cole's antics.

Cole feigned offense, placing a hand dramatically over his heart. "An idiot? I prefer to think of myself as a benevolent king lording over my subject."

Taylor snorted, crossing his arms. "Oh, please. You wish you were a king. Besides, what kind of king makes his subjects do ridiculous things like this?"

Cole leaned back against his desk, a smug grin on his face. "The kind of king who can make you do whatever he wants because you lost the bet."

Taylor rolled his eyes, trying to suppress a smile. "Well, if this is the worst you've got, then I've got nothing to worry about."

Cole's eyes narrowed playfully. "Oh really? In that case, why don't you put my skateboard up on the shelf for me?"

Taylor gave an exaggerated bow. "Yes, Your Majesty," he said with mock seriousness, picking up his skateboard and placing it on the shelf.

As Taylor turned back around, he noticed that Cole looked slightly flustered, as if he was nervous about something. Taylor laughed, pointing it out. "What's up with you? You look like you're about to give a speech or something."

Cole's ears flushed slightly, but then he composed himself and shot Taylor a mischievous grin. "Fine," Cole said, stepping closer. "If I'm your king, then that makes you my princess. And princesses need to look the part."

Before Taylor could react, Cole marched over to his closet and began rummaging through it with determination.

"What are you doing?" Taylor asked warily, watching as clothes began to fly out of the closet.

After a few moments, Cole turned around holding a bundle of clothing that made Taylor's cheeks flush red—a pair of tube socks, black lace panties, a pink mini skirt, and a choker necklace. Where had Cole even gotten these things? Taylor wondered.

"A bet's a bet," Cole said smugly, holding out the clothes to Taylor.

Taylor stared at him in disbelief. "You can't be serious."

"Oh, I'm dead serious," Cole replied, his smirk widening. "You lost the bet, dude. You gotta wear this for the rest of the day."

Taylor spluttered, searching for an excuse to back out of wearing the outfit. "This is ridiculous! I'm not wearing that!"

"You're the one who lost dude,'" Cole reminded him with mock innocence. "What's wrong? Afraid?"

Taylor's ears flattened against his head as he snatched the clothes from Cole's hands and spun around on his heels.

"Fine! But you're gonna regret this!" he called over his shoulder as he stormed off to the bathroom in the hallway.

Once inside the bathroom, Taylor locked the door and leaned against it, clutching the bundle of clothes to his chest. His heart was racing, and not just from frustration at Cole's antics. He set down the clothes on the counter and looked at himself in the mirror. His fur was still damp with sweat from skating earlier, and he could feel a bruise forming on his elbow from where he'd fallen trying to land that stupid trick. The cat took a moment to turn on the sink faucet and splash some cool water onto his face. Then he grabbed a washcloth, wet it, and wiped himself down.

With a deep breath, Taylor began to undress, peeling off his T-shirt and baggy jeans until he was standing in just his boxers. He hesitated for a moment before he slipped those off as well. Then he picked up the tube socks and pulled them on. They felt tight against his legs, the fabric conforming to his muscular thighs and calves.

Next came the black lace panties. They felt strange against his fur—soft and delicate in a way that made him blush. Taylor felt exposed even though no one else could see him as he grabbed the mini skirt next. It barely reached mid-thigh and felt scandalously short as he pulled in up and zipped it at the side. Then he reached over for the tube top and slid it over his head. As he worked it down over his arms and around his chest, he smoothed out his fur as best he could. Finally, he picked up the choker necklace and fastened it around his neck, its snug fit making him feel both vulnerable and oddly excited.

Taylor turned back to the mirror and stared at his reflection. His tail flicked nervously behind him as he took in the sight. He was every bit the reluctant princess. Taylor's first reaction was that of embarrassment. He reached down for the tube top, intending to take it back off. This was pushing things too far, no bet was worth this. But the cat stopped as he looked himself over in the mirror again. He looked, cute? Did he like this? The feel of the fabric sent a thrill through Taylor's body as he shivered from more than just nerves.

"What am I doing?" he muttered under his breath.

A knock at the door startled him out of his thoughts.

"Hey!" Cole called from outside. "You done yet? Don't make me come in there!"

Taylor scowled at the door before taking one last look at himself in the mirror. With another deep breath to steel himself, he unlocked the door and stepped out into the hallway.

The look on Cole's face when he saw Taylor was priceless—his jaw dropped slightly before morphing into a wide grin.

"Well?" Taylor demanded, crossing his arms over his chest in an attempt to hide how flustered he felt. "Happy now?"

Cole didn't answer right away; instead, he circled Taylor slowly like he was inspecting him from every angle.

"You look…" Cole began before trailing off with a low whistle. "Damn."

Taylor's ears burned as he tried to glare at Cole without meeting his eyes directly. "Shut up."

But instead of teasing him further, Cole stepped closer until they were standing just inches apart.

"You're beautiful," Cole said softly.

Taylor blinked up at him in surprise, caught off guard by both the words and tone. Before either of them could say anything else—or process what was happening—Cole reached out and gently adjusted the choker around Taylor's neck.

Taylor shoved Cole away and stepped back, his back pressing up against the hallway wall. “Dude, gay."

"A bet's a bet," Cole murmured again—but this time there was no smugness in his voice; only something deeper.

“Alright you had your fun," Taylor said with a slight panicked edge to his voice that he tried to cover with frustration," I'm getting out of this stupid outfit."

Taylor went to push past Cole, to retreat back into the privacy of the bathroom, but Cole caught the cat's wrist. The lab spun Taylor around and pinned him back against the wall. Taylor's breath caught in his throat.

“Dude, what the fuck are you doing?" he said hesitantly as his heart began to pound more rapidly in his chest.

“You're beautiful," Cole said again as his intense gaze hungerly looked over Taylor's scantily clad body.

Taylor's face burned as he squirmed in his mini skirt, the hem barely covering the tops of the thigh-highs.

“You really do look like a princess…," Cole murmured—but this time there was no smugness in his voice; only something deeper.

"Bro - get off …" Taylor started to say, his voice a mix of defiance and uncertainty as Cole stepped forward and kissed him. The kiss caught Taylor by surprise. Cole's tongue darted into Taylor's mouth as the lab's paws grabbed ahold of the cat's hips and squeezed.