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purplelescent · 16 days

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A Pair of Jokers

Pokemon Fan-Fiction: Grimsley/Reader

Summary: Now that you’ve lost a game of cards to your childhood best friend, Grimsley, you owe him a favor. Although you don’t know if you can survive the onslaught of his flirtatious teasing while spending the day with him. You’ve had sincere, secret feelings for him for years. Perhaps, it’s time to clear the air and let him know how you really feel.

Why do I always agree to play cards with him? The man's a world-class gambler and-

Ugh.

Look how pleased he is with himself. Dinner's always so nice until we get to playing cards. Sporadically, we get together to catch up every few weeks. This used to be a friend group thing, but lately, it's just been us.

Secretly, it felt kinda' romantic. It's not like I've had a crush on him or anything. For like… years…

…

I'd never admit it.

Drawing my next card, excitement hummed through my body. I had it! Victory! When we reveal our hands, I'd beat him. We bet something special tonight, a favor. We also wagered that the loser pays for dinner too, but that's clearly not as important.

When I played my hand, four of a kind, the odds were in my favor. His shock looked so genuine.

Then he revealed his hand, a straight flush of hearts.

My body’s hum of excitement turned sour and fizzled away. He flashed a coy smile, propping his chin on the back of his hand.

"How perfect." Grimsley purred.

"Yeah. Yeah…" I grumbled, trying not to blush at the tone of his voice.

"I apologize. I promise I'm not gloating. Just musing over the cards you dealt me. I’d almost think you rigged the deck. Are you trying to tell me something?”

Taking a deep breath to calm myself, I caught a faint trace of his cologne from across the table. The scent held a soft, but powerful vibe, reminding me of a summer sunset on the ocean. My heart began pounding fast as I looked into his bright blue eyes.

“We should have played voltorb flip.” I grumble.

“That’s only a one-player game.”

“Exactly.”

“You wound me.” He chuckled as he leaned forward.

Leaning away, I rested my head against the back of the chair. The ceiling was the perfect blank slate to calm my emotions down. Sure. I'm acting like a sore loser, but better than letting him find out how he's making my heart race. Now that I've lost, I realized how screwed I am. That's what I get for being confident.

If he wanted his prize he'd have to bring it up. I started to wish I hadn't agreed to our little wager. He'd choose something embarrassing for me. Now that was a safe bet.

Grimsley and I have known each other since elementary school before we even got our pokémon. I remember when his family moved into the apartments we lived in. Everyone thought they were reclusive freaks at first.

"Getta' load of those snobs." My brother mumbled in my ear.

"I heard they was rich. They pissed it away and now they're like everybody else." Jackson said, or was it Mike? One of my brother's douchebag friends said it. That much I remember.

They introduced themselves to the boys and invited them to come play. Not out of a sense of goodwill though. The new kids were the entertainment. Grimsley and his older brother slowly joined the neighborhood pack of boys, but it was always clear they were the odd ones out.

I remember the day when he fully became one of the guys though. The boys were playing truth or dare, which means they were doing stupid things to one-up each other. I didn't think much of it even when they started betting money and candy. One of the neighbor girls, I can’t remember who she was either, and I were playing catch with a stolen dodgeball from school.

"Um… excuse me."

I squealed and fumbled to catch the ball. It made a harsh “poink” as it hit me in the chest. Turing to look at him, Grimsley cheeks glowed rosy red. I must have thought he was sunburned at the time.

"Du-de! What the heck!"

He smiled a little. His blue eyes betrayed his nervousness though. In a flash, he pecked my lips with his and ran back to the group of boys who were laughing and jeering.

"Told you he'd do it! Here's the one-fifty!" One of them sneered dropping the coins on the ground.

My heart was going to burst out of my chest. I felt like I was burning up. My heart fluttered and broke in an instant. That was my first kiss- stolen and sold for less than a bottle of potion. At that age, I don't think I was even thinking about romance yet.

I whipped around seething.

"Grimsley!" I screeched.

When I remember this part, it's always in slow motion. I knew I'd get in trouble, but in my nine-year-old mind, I had no choice! This was what he deserved.

He turned to look at me as he stood up. I threw the dodgeball. It slammed him square in the face. It bounced off with the same “poink” noise it made when it hit me. Coins scattered and clinked on the ground. I stormed off before he could pull himself off the ground.

So apparently, taking a dodgeball to the face made you “one of the boys”. I had inadvertently improved his social status in the neighborhood.

Lucky little bastard.

He's been toying with me ever since. I can’t even begin to tell you when or why my feelings started for him. Yet, after that, he never left me alone.

Grimsley made it his hobby to embarrass me any chance he got. He always tries to fluster me with pickup lines and innuendos. I learned to block it out by the time we became adults. Each time he'd flash a big, cat-like grin before pulling the "Joking!" card and have a good chuckle. Then I’d chastise him with a little slap.

To him, it was just friendly banter. To me it was torture.

In a pleasant way, but since none of it is real then it all circles around to make me feel worse afterwards. If he knew I really did have a massive one-sided crush, he’d probably be weirded out. So, whenever he starts up, I just go along with it. Then I move on as if I wasn't still entertaining the romantic ideas he provoked within me. I’ll get over him, someday.

Grimsley softly called my name, "Are you falling asleep?"

"No. I'm waiting."

"For?" he asked, his voice litling playfully.

I finally ended my staring contest with the ceiling to glare at him.

Arceus.

Look at his shit-eating grin.

If I wasn’t on the hook, I’d think it was cute. When gambling, he becomes unreadable, like a perfectly still pond. He has a few tells I try to look for; a slight twitch of the left eye, sweat around the side of his cheeks, his grin tugging slightly to left when he's sure victory will be his... But he's practiced to perfection at hiding them. Yet outside of the game, when he has nothing to hide, he's quite animated.

Dramatic is a better description, in my opinion.

He wanted me to bring it up. He'd leave me dangling on this hook all night if he had to. Just like a purrloin toying with his prey.

Steeling myself for the inevitable, I asked, "What do you want?”

The winner could ask the loser to do anything within reason. The second he presented the idea, I could only visualize one thing. I was going to make him clean my apartment.

Could you imagine?

Grimsley, member of the elite four and professional gambler, scrubbing a toilet, taking out the trash, and folding socks. It was too good to pass up. It’d make a great post for my socials. I wasn't even going to make him wear an embarrassing costume! I wasn't a total savage when it came to dares. Even if a cat-eared maid dress would suit him.

I mean, it's not like I would have had him clean a dump either. Work ramped up with a new project leaving me precious little personal time for the past three weeks. It was sleep and eat only! I couldn’t even bear to look at the vacuum, I was so tired.

That being said, what could he even want to make me do? I had been waaaay too blinded by my fantasy. How could I think I’d win? Like, how could I forget I haven't beaten him since… How long has it been? Was it since I was in college?

I must have had too much to drink.

I needed to mentally prepare for the worst. So, maybe… he'd make me wear a really stupid outfit and post pictures of it? Make me participate in a Pokémon Musical? Take a bite right into an extra ripe tamato berry?

Oh no!

What if he made me hug an extra mucus-y cubchoo? Ew! No! He wouldn't!

I drank from my water glass to clear my nerves.

"Tomorrow, I want to take you-" Grimsley paused.

I nearly choke on my water. He wants to take me, like what?! On a date?! My cheeks were alight with heat.

No way!

He's about to pull his signature bait and switch. I feel it. He always tries to get a rise out of me. And damn if he didn't succeed every time. Scraping the last bit of courage inside me, I looked him in the eye. Grimsley wore a smug, satisfied grin.

Ugh. Damn it.

His eyes narrowed like a cat Pokémon ready for the kill-

"-To watch my match tomorrow at the league!"

Bingo! Just as I suspected! No way was he ever going to ask me on a date. I know him a little too well.

Although… How surprisingly tame of all the things he could ask for. I must’ve missed missing something. He's never gone out of his way to invite me to a match before. If he'd ask, I'd gladly say yes. I'm sure he knows it. As the prize for a bet… it's kind of a non-prize.

How un-Grimsley of him.

I shouldn't complain. It's nowhere near as bad as the stuff I thought up. Before and after his comment.

“O-okay.”

He stood from the table abruptly; clearly riding the high of his victory.

"Fantastic! Do you still have that blue dress you wore to my brother's wedding?"

"Uh. Why?"

Now that sounds fishy.

"Because… we like to put on a grand presentation for our challenger. I don't want you to feel underdressed. Although! If you're uncomfortable, then you don't need to!"

Oh. I suppose I’m being paranoid.

"I mean, okay. I have it."

I reached for the bill on the table to pay for tonight's dinner. I was not looking forward to this. He always gets the pricey stuff. My consolation was the bill would still cost less than if I had bet our usual prize money on our card game. My fingers barely grazed the paper when he swiped it off the table.

"Hey. I'm supp-"

"Oh, and make sure to wear comfortable shoes. I remember how much you complained about those heels you wore with the dress last time. Or? Do you want me to carry you again?" He grinned as he recalled an embarrassing moment for me.

“Oh, stop it. You only helped me to my hotel room.” I grumbled.

I threw away the offending heels after the wedding. Even if they gave me the chance to be carried like a princess. That night was a bit of a blur, but I do remember being embarrassingly obnoxious when he carried me. I couldn’t bear to look him in the eye the next morning.

He started to walk to the front of the restaurant while he talked.

"After I trounce the little upstart we can go for lunch!"

I scrambled to grab my purse. Fumbling for some cash to leave as a tip, I noticed a neatly set of folded bills tucked under the salt and pepper shakers.

Man, when he's ready to go, he's got it all covered.

I chased after him, politely saying goodnight to the staff as I passed.

"Grim, the tab-" Did he forget I'm supposed to pay?

"Relax! Don't worry about bringing any cash. I'm not going to wring you for a meal."

"But right now-"

He had already handed over the receipt and his card to the cashier by the time I caught up to him.

I gave up.

When he remembers he'll send me a text at, like, three in the morning asking me to send it via Poképay.

*****

Waiting by the front steps of the league made me feel a little bittersweet. The faint breeze brought a refreshing cool to the morning. Every kid dreamed of coming here, standing before the Elite Four, and battling your way to the top. I dreamed that too. But I'm not here by my own strength.

I couldn't cut it. I told everyone I lost interest in battling, but the truth of it is my best isn't good enough to be the best.

The guard asked me regarding my badges, assuming I was the challenger.

"Oh no. I'm here to watch Grimsley's match today." I muttered, focusing more on some imaginary spot on my dress rather than looking him in the eye.

"I see. In that case, we have a visitor's waiting room where the matches are live broadcast. If you go back toward the PMC, you'll turn-"

My name was called out from the other side of the entrance.

Oh. Grim wasn't kidding about dressing up.

I hadn't seen this outfit before. He's truly a classy card shark. He wore a white shirt and tie, but the whole ensemble was ornate. His suspenders connected with a dark navy blue high collar that had a long scarf flowing from the back.

Despite the ornate golden decorations glittering in the sun and black straps on his forearms, Grimsley made it look so casual.

He smirked when we made eye contact.

Aw… come on man! He knows he’s cool!

And I couldn’t help, but smile in return.

"This is my guest. She has special permission to watch from ringside." He said, almost purring.

The guard gave a curt nod. He stepped back and gestured to invite me in. It was only one step forward, but I faltered at the threshold. I didn't belong on the other side. I wasn't powerful. My pokémon weren't fighters. They were, to put it delicately, fat, little, spoiled couch gremlins.

A strong arm, wrapped around my shoulders. Grimsley pulled me along and up the stairs with impatient energy.

"Come along! I want to show you my new arena before the challenger arrives!" He gushed with enthusiasm. "We recently completed remodeling everything."

Our hurried steps echoed across the ancient stones as we approached his arena. He gently directed me to the entrance, holding his hand out to gesture me forward.

"Ladies first." He said with a polite gentleman's tone.

The whole room drowned in darkness, which was to be expected of Grimsley's type specialty. A loud swoosh of igniting flames caught me off guard. I spun to ask Grimsley a question, but the door had closed and he wasn't with me.

"Grim?" My voice felt small in the dark room only lit by torch light.

Only the hammering thud of my heart responded.

The moment passed and nothing happened. Turning, I decided I would go ahead and wait for him. The red carpet led me to the stairs. Imposing, curved red claws barred my path. With a flourishing snap, the claws released the pathway. My body instinctively jerked back.

I reminded myself this is only a very elaborate set. The mechanism should let me pass and not impale me. Ideally. I decided I should go ahead, I took a confident step forward, but my gut was in control of my legs. So, that step was about as confident as a wimpod.

Still, I pressed forward. My gut twisted and the hairs on the back of my neck bristled. I dashed up the stairs two at a time, mentally thanking Grim for telling me to wear comfortable shoes. My cheeks burned with embarrassment.

It's all for show. Why am I scared? No! How stupid!

I'm not scared of the dark!

I… I just…

Shut up!

The claws snapped shut at the top of the stairs. I jumped squealing forward only to be caught in an embrace in the darkness. A second later the lights from a chandelier above flickered to life.

Grimsley held me flush to himself. Violent ping-ponging beats of my heart hammered in my chest. Surely, he could feel it too given how close we were. His hand felt like it belonged on the small of my back. Once again, he looks so terribly pleased with himself. He clicked his tongue playfully. His cologne flooded my senses again. I had to catch my breath, but his damn cologne made me pleasantly light-headed.

"Aw, were you frightened?" His blue eyes glowed with mischief. He dipped his face closer to mine. "Nothing's going to hurt you, but I'll protect you anyway if you want.”

Warm tingles and shivers trailed from the top of my head and chased down the length of my spine.

Then it clicked.

This was a setup. He didn't want a ringside audience. He wanted an excuse to toy with me today! I pushed free from his grasp.

Come on brain time to get a grip!

"Oh so brave of you! How'd you even get here before me?" The beating of my heart refused to slow down. But I was satisfied I pulled out a little sass.

"A magician never reveals his secrets."

"Warp pad then?"

"So, what do you think of my domain?" He said, ignoring my obviously correct guess. He swept his hand in a grand flourish.

To an extent, it was a bizarre blend between gaudy and elegant. The green floor reminded me of the felt covers on a poker table. Golden chains suspended the platform in the air. Grimsley sauntered to a luxurious black sofa sitting on the edge of the battlefield. I followed him over while admiring the glittering chandelier.

"It's very you," I said.

"Then what do you think of me?" He said.

"Fishing for compliments?" I teased as I sat down next to him. "Well then, it's pretty cool. Quite bright for a dark-type specialist. Kinda’ unexpected."

He slid over on the sofa. I could sense another round of teasing coming. Before he could lean in to say only Arceus knows what, I pulled out my phone with the Poképay app at the ready. He tilted his head. Distraction technique successful!

"You were so wound up last night you paid for dinner." I deflected.

"Well… yeah. That's how restaurants work." He chuckled.

"Doofus. I'm talking about the bet. I was supposed to pay, remember? How much was the tab?"

Grimsley froze as if someone hit pause. His charming smile seemed thinner than usual.

"I'm… afraid I don't recall."

"You?" I scoff. "You can't remember how much money you spent? Mister "when on his Pokémon journey two years late to earn extra money before leaving home"? Mister "mental math who could do my calculus homework for me without a calculator"? You don't know how much dinner was?"

The second I saw it, a faint bead of sweat on his forehead, the lights extinguished. We plunged into darkness again. I couldn’t suppress my surprised gasp. I never was good with surprises. Only the faint light of my cell phone illuminated the couch.

A loud click resonated to indicate someone had arrived. The challenger no doubt. Grimsley's hand brushed my cheek and I gasped. My phone’s screen timed out, extinguishing the last faint light we had as Grimsley leaned forward. His lips were so close to my ear that it tickled.

"Looks like I'm first. Just sit and look pretty for me for now." He whispered in a low voice. Another rush of tingles burst inside me.

Sir.

Are you trying to kill me?

The sound of the torches at the entrance flared to life giving a dim glow to the room. He stood from the sofa, his scarf swirling dramatically as he walked to his place on the field. My heart felt like it was going to burst out of my chest. If this keeps up I'm going to have a heart attack. I only could hope the challenger wouldn’t notice how much I must be blushing when all the lights came on. My face, ears, and neck are burning. He was going hard today. It was different. Grimsley turned to look at me over his shoulder.

Even in the dim light, I could see his cat-like grin. He really just wanted an excuse to toy with me today.

How bored are you?!

The claws on the stairs unfolded and shortly after a girl with double buns came bounding up the steps. The claws snapped shut behind her. The torches and chandelier came to life. The girl didn't so much as flinch. Damn. How embarrassing that a ten-year-old has more stones than a grown adult… I wanted to curl up behind the couch.

“What will be determined here is which of us can absorb the opponent's light and shine... But who will decide that? It shall be I, Grimsley of the Elite Four, and I will fulfill my duty to be your opponent." He said,” But first, I have a special visitor today. You don’t mind having a ring-side audience do you?”

The girl leans to the side a little to get a better look at me. She must not have realized I was sitting here. I waved trying to appear casual. She cupped her chin, pointing her finger in a thumb like a checkmark and humming to herself.

“Oh, yeah! That's totes fine. I don’t mind your girlfriend watching!”

Grimsley shot a coy grin over his shoulder at me.

“Th-thank you! We're… actually friends. Not dating.”

“Ooooh! Sorry! ‘Bout that!” she laughed. The girl rubbed the back of her neck sheepishly.

His expression flattened in an instant as he turned to face his challenge. No doubt ready to get to business.

*****

Another fierce explosion shook the arena. The hot gust of rushing air flipped the hem of my dress a little more than I anticipated. I yelped, snatching it back to keep from revealing too much. When I looked up, I caught Grimsley's look over his shoulder. His eyes flitted over me from top to bottom. Then he sharply turned away back to the match.

As the debris settled, his bisharp, Philomina, lay defeated.

His shoulders slumped slightly. He slapped his forehead and dragged his hand down his face.

Thanks, kid! That's the expression I wanted to see last night. Even seeing it from behind was delightful.

It's a little mean to smile at the expense of your friend, but he's such a sore loser. Watching him squirm with frustration while trying to be a self-controlled gentleman was always funny.

Grimsley returned his pokémon. A loud joyful cry rang out. The challenger jump-hugged her huge darmanitan, celebrating their victory. He took their joyful moment to recenter himself. With polite applause, he began to speak to them with his usual grace and charm.

"See, victory shines like a bright light. And right now, you and your Pokémon are shining brilliantly." Grimsley gestured to the warp pad.

With a wave goodbye, she ran on ahead to her next fight. Grimsley stood still watching patiently until the last light of the warp pad vanished. A soft quiet calm fell over the room. I didn't know if I should compliment how well he did or console him on the loss. Grim flopped on the couch, drained of any of his usual grace.

"Maaaan…." He groaned. He was squeezing the bridge of his nose.

"It was very close," I finally said.

"A loss is a loss." He sighed and he started to rub his neck. "But what the heck are they feeding kids these days? If she defeats everyone else, she'll be the third champion under the age of fourteen in a row. Crazy, man."

"Yeah, it's all over the place like Kanto and Hoenn too. They’re calling it a generation of child champions."

We sat in a lull of silence while Grim shook off his defeat. He looked at the green floors where the remnants of debris and scars from attacks littered the arena floor. His hand paused on the back of his neck.

“Okay,” he breathed out in a whisper.

“Hm?”

Grimsley stood up from the couch. We locked eyes briefly. Whatever words he had locked and loaded didn’t come. He just smiled before turning on his heel and pacing in front of the couch.

“Grim? What’s up?”

This behavior was new to me. He finally stopped in front of me. A scarlet blush covered his face from ear to ear. I recalled that little boy he used to be from years ago, cheeks burning red right before stealing my first kiss. Was he still embarrassed about losing? I should have consoled him after all.

“Hey, it’s okay. You and your team were amazing. I certainly couldn’t handle such an intense battle like that. I’m very impressed.” I said.

Grimsley tilted his head as though he didn’t hear me. Before I could say anything else, he laughed. His charming laugh echoed around the hall.

“That’s not-” he sighed. “You’re so sweet. That’s not what I’m thinking about.”

“Then what’s wrong?” I asked, ripping the bandage off.

“At the end of the battle, when you cried out, I thought you had gotten hurt. That some debris had hit you. I could never forgive myself if you were hurt on my account.”

So, that's it. He was worried about me! I hopped off the couch to hug him. This time our embrace lacked the sensual nature of the first one we had shared before the match. Grimsley kept his arms wrapped around my shoulders. He sighed relieved. I still felt warm bubbles in my chest.

Shh! Stupid crush. Can you see we are having a very healthy platonic moment between friends?

“I love you,” Grimsley whispered.

I sharply inhaled. Platonically, right?

“Love like?”

“I love you. I want to be with you.”

I like Grimsley. I do. Really. Really. Really do. But if he dares to tease me now when we were having an honest moment... I can’t let him wind up my feelings like this again. I’ve had way too much for one day. If I hear him say he's only joking again I’ll lose it.

“Hey. I… I can’t do this right now.” I said, pulling from the hug.

Grimsley immediately took his hand off of me, wide eyes.

“I’m sorry!” He said. His blue eyes were piercing, but soft. “I didn’t mean-”

Of course, he didn’t mean it. That’s how this goes.

We stood frozen staring into each other’s eyes. I don’t think I have ever seen this expression of his. Gone was his devilish smile, and the cat-like glint of his eyes. To me, he looked like he was going to be sick. I took his hand and focused my attention on it. I couldn’t say what I needed to say if I kept looking at this- worrying expression on his face.

“Listen, you always do this flirting thing, and I get you find it funny, but-” I paused. “I don’t.”

Do I admit how I feel? We are friends. Surely, he’d understand. It might upset him to know my feelings aren’t the same, but if he knew how much I liked him, then he’d stop. Then I could finally get over this one-sided crush already.

“Like, it’s fine now and again, but all at once like this is… I… feel so overwhelmed and I know you don’t mean any of it. I know you’re not trying to overwhelm me and you don’t like me this way. You’re just… playing.”

My voice began to pitch up. This is the worst. I didn’t want to cry.

“I get that it’s a joke, always just a joke, but- Arceus. I actually- do. I mean, I love-”

The rest of the words were crushed by the tightening of my throat. I shut my mouth. This was a stupid thing to say. I should have brushed it off and played along like always.

Grimsley swore under his breath as he fumbled in his pocket before pulling out a handkerchief. He dabbed the fountain of tears in the corners of my eyes, careful to press too hard. He called my name in such a soft tone as if he feared he’d startle me.

“It’s not a joke! It’s never been a joke!” Grimsley said. “I thought you didn’t have feelings for me. So, I… pretended I was joking because I didn’t want to upset you. But I kept trying because… I couldn’t let my feelings go. I hoped you’d take it seriously one day.”

He squeezed my hand. I couldn’t process it all. This… this is real?

“You’re hurt because of me after all.” He muttered.

“That’s a terrible approach to courting a lady, you know,” I said, taking the handkerchief from his hand to wipe away more of my tears myself.

“I’m so sorry.”

“This whole time… you really liked me?”

Grimsley nodded, “And you liked me?”

I nodded in return. The tears still wouldn’t turn off, yet I couldn’t stop from smiling. The whole time we could have enjoyed being together! Instead, we wasted years dancing around each other's feelings. I couldn’t stop the laughter from bubbling up. We're grown adults now! And we could even have an honest conversation? It was so absurd! Grimsley couldn’t keep the smile from growing on his face, perhaps having the same thoughts I was. The tears finally stopped.

“I always thought I’d be the king to your queen, but it seems the truth of it is we’re the pair of jokers.”

“That fits,” I said. “We’re so stupid.”

“Well, now that we’re on the same page, may I, at long last, take you on a date?” He said.

A date. This felt too good to be true. I felt a surge of confidence knowing Grimsley’s true feelings. And I knew then I had to do something to make up for all these years of cowardice.

“Yes, but-” I said in a lilting voice.

“But?” His eyebrows shot up in surprise.

“I remember you took something from me. I need it back.”

Grimsley’s lips parted ready to answer, but it was clear he was racking his brain to figure out what I meant. My heart started up a ping-pong rematch as I took a step closer.

“I… don’t know what I’ve tak-” Before the poor man could finish his sentence, I grabbed him by the collar to pull him down to meet my lips.

It was quick. Just like it was this first time, a feathery, peak on the lips. When we pulled back, his face was once again rosy red. I’m sure my face was too.

“You stole my first kiss. I had to take it back, you know.”

Moving past the surprise, once again I saw that well-known cat-like grin appear. His piercing blue eyes sparked alight with mischief. Grimsley slipped his hand onto the small of my back. He pulled me in close and pressed his forehead to my own.

“Well, such a kiss can’t be returned,” he said, his voice low and sultry. “But allow me to repay you with interest. I insist.”

Grimsley pressed his lips to mine with softness. I let my hands slip away from his collar to instead rest on his shoulders. His thumb rubbed small, gentle circles on my lower back, as his other hand came up to cup my cheek. Once more, a pleasant lightheadedness overtook me from the calming scent of his cologne.

As we pulled apart, Grimsley sighed with happiness. I couldn’t help chuckling once more.

“My, look how pleased you are with yourself.” I tease as I stand on my tip toes inviting another kiss of many more to come.

*****

Bonus: Grimsley's POV - Just before you arrive

"Grimsley!" Shauntel gasped, scandalized.

"Please. It's too early in the morning for this." I stretched with a yawn.

Curse the trainer that scheduled to come in first thing. It's not unusual for me to be so tired in the morning like this, but today it's not because I was up all night at the poker tables. No. I couldn't sleep at all thinking about my date… or well almost date.

"Yes, Shauntel. I have to agree. It's much too early." Caitlin said, shuffling into our break room.

"You remember the girl- his childhood sweetheart? The one he was finally going to ask out."

Caitlin gave a sleepy nod. Her tea cup and the kettle floated around her as she used her telekinetic ability to pour the water.

"Now hold on- we were never sweethearts before-"

"He still didn't ask her on a date! Look at him! All dressed up and nowhere to go!"

Caitlin mumbled a sad oh noise before she mentally picked up a spoon to stir her drink. She doesn't care. Despite her girlishness, she doesn't give two cents about romance or relationship gossip.

"I'm going out with her for lunch after the challenger battle." I huff. Shauntel glared at me like gum on the bottom of her shoe. "Aaaaand we were alone for dinner last night."

"He beat her at poker and forced her to come sit around as his cheerleader."

"Slander!" Of all the indecent ways to describe it! She was too creative sometimes. But it certainly shone a spotlight on my failed plans. No matter how she or I put it, it wasn’t the romantic afternoon I intended to have.

"How inelegant." Caitlin shook her head, disapproving as always.

"I was going to ask her, but I-"

"Was too afraid she'd shoot you down if you bore your sincere desires and you'd lose your dear friend to awkward, unrequited love."

The psychic girl's words cut me to the quick. I glared at Caitlin. She took a seat at her favorite spot and sipped her tea, refusing to look at me.

"I thought we all agreed you wouldn't read our minds without consent," I said.

"I didn't have to read your mind. It's all over your face."

Liar.

But Shauntel nodded in firm agreement with her. I'm outnumbered. I know when to fold.

"If she doesn't have feelings for you then why even continue to pursue her? You'd think having dinner alone together for, oh, 6 months? You’d think it would have resulted in more romantic feelings by now."

And the brutal death blow.

Caitlin may talk about grace and elegance, but the girl was savage.

Before I could respond, the doors thankfully burst open with our much too energetic Champion and Marshal. The poor guy looked like he was going to collapse. Sweat dripped off his forehead in rivers. And yet, Iris looked barely misted. I wondered how many miles they ran today. Not that I would ask for fear Iris would interpret this to mean I want to join them.

Since Adler's defeat as champion, he took to traveling. Marshal ended up latching on to Iris as his new mentor. A grown man calling a fourteen-year-old his master would be funny if she wasn't so ridiculously powerful.

"Oookay! I'm going to get cleaned up and ready to face our new challenger!" She declared. "Are you all ready?"

We all mumbled an affirmative response. Except Marshal who gave a hearty, headache-inducing, "Yes ma'am!"

"Wake up sleepy heads! It's time to rumble!!" She yelled with a growl as she ran past us to her personal locker room.

"Iris, ah, a moment." She skidded to a halt and jogged back to me. "I have a friend coming. I know it's usually only the combatants, but you wouldn't mind if she watched my battle today?"

"As long as the challenger doesn't mind, it's fine by me." She said, Iris tilted her head and narrowed her eyes. She straightened up in an instant, "Oh! Is it your girlfriend the girls told me about? That's so-"

"Exaggerated." I huffed. Shauntel and Caitlyn turned away from my firey glare.

Cowards! Look at me when you heckle!

"But he's pining with desperate hope." Caitlin chimes in, looking me in the eye as she speaks.

Not reading our minds my ass.

She just smirks.

Taking the opportunity, I excused myself to get ready. I hoped I'd go first, honestly. I wanted to get this over as quick as possible so I could spend time with her.

I only fell in love with her by chance. Right time and place as they say.

I hated other people. I hate this town, this apartment, this group of "friends". All of it.

When the pack of neighborhood boys approached us, I knew they had been talking about us behind our backs. Clarence, my older brother who was too soft and naive, appreciated the "friendship". He couldn't figure out they were making fun of us at every turn.

I tolerated it with a smile. After all, if others know your true feelings, they can use it to their advantage. They'll have power over you. My childhood "friends" must have thought I was some plucky kid, a simple sucker. It was better that way.

We made stupid bets and dares. They must have thought it was funny what I was willing to do for money, but I had a plan for my pokémon journey, I was going to be prepared. I would never come back, just like my sister, Marinette.

I hate thinking back on the stupid things we used to bet. That kiss I stole is a bittersweet memory. In my young mind, I foolishly believed she was overreacting to such a nothing act. I only chose her over her friend because everyone knew how timid she was- or so I thought.

I hated her. Even if her assault had the unintended consequence of making me look tough to the other kids. I hated her so much.

And I cringe remembering how selfish I was. That should have been the end of any friendship. Forget love or romance.

Occasionally, when I felt spiteful, I'd tease her with some veiled romantic comment to watch her squirm. I always made sure I was out of her range before she realized I was joking at her expense. Seeing her range of emotion was amusing. She's incredibly expressive. I told myself it was funny. I couldn't find any reason I would keep doing it otherwise.

My twelfth birthday approached and the guys wanted to play poker to celebrate. They congratulated me for finally getting the balls to go on my Pokémon journey. Truth was, I had only waited so long to pull together a little more cash. As the night drew on, I was becoming more and more of an unwanted guest at my own party.

“You’re a cheating little shit!”

I was beating Jackson even though he was the one cheating. I had caught his scraggy slipping him cards out of its loose skin. I didn’t say anything. It made the game more interesting.

“I’m not. It’s only luck. I can quit.” I folded my hand together, returning it to the bottom of the deck.

My accuser looked like he was going to crack his teeth from how hard he was clenching his jaw. I ignored him as I tucked my cards back into the deck. I was content to just watch at this point.

After tomorrow, I wouldn't have to deal with any of these losers again. The night dragged on and we were all asleep only when the sky began to pale with the coming of the morning sun.

This was my mistake.

I didn't wake until two in the afternoon, still groggy from last night. No one was there. A soft clattering from my nightstand was the only sound in my room. Purrloin's pokeball was missing. Hopping out of bed, I knelt on the floor. The pokeball clattered and wiggled wildly under the nightstand. Poor Purry must have been so confused being unable to let herself out. I supposed I knocked her ball off the table and didn't notice. The tight space must have triggered the emergency locks that prevent pokémon from coming out in spaces too small to fit them.

The ball burst open the second I had it free from the confined space. She hissed and spit in a wild tantrum. Her tail lashed with violent abandon It was best to leave her be, unless I wanted to end up her scratching post.

I shuffled out to greet my mother who let me know my "friends" all went home. She asked if I was sure I still wanted to head out today since it was so late. She recommended I start here with the Castelia gym, but Purry and I would be severely disadvantaged. And Nimbasa is only an afternoon's walk. I'd arrive just as the city started to light up for the night.

Purry latched onto my leg. She waved one little arm with distress and led me back to my backpack. Nothing seemed out of place. I rummaged through my supplies yet nothing caught my attention.

My wallet slapped me in the face as she threw it at me, "Purry!"

It struck me. They all left before I woke up. Tearing the wallet open, it was empty.

Even though I had a savings account with more, I wanted to save it for emergencies. And as my anger boiled over, the indignity of being robbed couldn't go unchecked!

"Bye Mother! I love you! I'll call later. I'll tell Clarence to call too if I see him. Bye!" I cried out as I dashed out the door. I don't think I had ever gotten dressed so fast before.

Purry and I split up, I knew she'd find them faster. I began checking all the usual hangouts; the lousy bodega, the arcade, Casteliacone…

A sharp chirp caught my attention over a crowd from an alley. Purry led me through a corridor of trash cans and back doors until I could hear the voices of my "friends".

Before I could turn the corner, I could hear her. She blocked their way.

"What kind of friend steals! Take it back!"

"Piss off runt. No one asked you."

I glanced around the corner to see them. She stood on the other side, blocking their path. Her brother pushed through the group yelling at her to move.

"No! This isn't okay!" She cried.

"You're just mad about it because he is your booooooyfriend~'' One of the boys mocked. Another one made sloppy kissing noises.

"Sh-shut up. He is not! Don't be gross!" She squeaked.

"We didn't go out with a wad of cash. That spoiled brat can figure it out!"

"That’s his money! He should get to use it! It's not his fault you went unprepared and couldn't cut it!"

He threw her against a trash can. He threw his own sister.

I don't remember what I said. A strange, aching fire sparked through me. My arms and legs hurt from shaking. I moved and spoke on autopilot. I challenged them all to a fight.

Purry wasn't as high-level as the other pokémon they used. However, she weaved around them like a graceful dancer, letting their clumsy partners beat each other. She only struck when a critical hit could be certain. I was lucky to have such a battle genius of a pokémon for a first partner. Despite the abysmal odds, victory was certain.

A heavy thud of the last pokémon Timburr signaled the end of my first battle.

"Give me my money." I snarled.

They threw the cash on the ground before running off. Turning, I looked at her. She flinched and shrunk back into the trash. Of all the emotions I had provoked in this girl, I finally felt guilt. I hated that look. That fear in her eyes.

"You…" I fumbled with what to say. The adrenaline was wearing off. I didn't understand why she did that. Of all the rare times she was brave and she chose to stand up for me. I offered my hand to help her.

"Thank you." I finally managed to say. I gently beckoned her. Her expression melted as she took my hand.

Money secured and one trip to the Pokémon Center later. I was ready to leave. But I waited while Nurse Joy patched her up. She had scratched her arm when she fell in the trash. Thinking about it made my blood boil. I'd never hurt Marinette or Clarence like that! I offered to walk her home, but she walked with me until we reached the gates to Route 4. She seemed nervous.

"Are you sure you want to go now? It's almost dark." She said.

"Yeah. There are more interesting pokémon at night." I grinned.

She smiled at me. Suddenly, another warmth took hold of me. I couldn’t contain the smile spreading on my face. I liked her smile.

"I know we aren't, like, actual friends. But be safe, okay?"

And that's how it started.

How I found myself coming home to see her as often as possible. I know my mother was relieved another child hadn’t left forever. It took a while for me to realize that I had developed a crush. It was only when Mother asked me in my teens if we were dating that it hit me how I felt about her. Over the past years, I keep going back trying to coax her into loving me.

Caitlin was right.

We've known each other for so long. Never once has she expressed romantic interest. Oh sure, I could fluster her to no end with flirtatious teasing. Her teasing never held return any flirty vibes. In fact, as soon as she realizes what I'm doing she begins to give me the blankest stare. I always backpedaled or played it off as a joke, anything to keep it within "Just friends" territory. Then she sighs relieved, answering my suspicions. I know I should have given up, but when a little time passed, I'd get greedy. Then I'd try again to test the waters and see if her heart had changed. I've never wanted to push for a romance if she wasn't interested.

For all the heart-pounding gambles I'm willing to take, I’m unable to bring myself to risk what I have with her. Some of my gambling buddies would laugh at me if they ever knew. The stakes were too high and I say that having risked life and limb, literally.

But today is the day. I'll sweep her off her feet.

Her friendship warmed me like the sun all these years. She was my one safe spot. She’s where I felt at peace without feeling as though I was missing out on some worthwhile thrill. But I know now I need her and if there's any hope of having her by my side, then I'll have to risk everything we have. And if she turns me down, well...

Perhaps then I'd be able to move past this unrequited love.

But she's worth it.

I stopped by the front, guarded by a league staff member who kept all, but elite trainers out. She was waiting for me.

I took a deep breath to calm my nerves. She wore that cute dress like I asked. It wasn't extravagant or too formal. However, the flutter of the delicate fabric made her look like an angel.

I recalled the night of my brother's wedding when we danced together.

Her eyes sparkled under the fairy lights and her face was a beautiful blushed color. When the night was over, she cursed wearing those awful heels. They left nasty cuts on the back of her heels. She teetered unsteadily from indulging in a little too much alcohol, wincing from pain. Before I could stop myself, I had scooped her up in my arms to carry her. She giggled the entire way.

At the threshold of her hotel room, she leaned against the door frame with a wide, unabashed smile.

"Thank you my darling prince charming," she whispered, still giggly.

Oh. That had been so unfair and painful! In the most pleasant of ways. If she were sober, if she had meant it, those words would have sent me over the moon.

"Go to bed silly," was all I could respond with at the time.

I called her name as a breeze picked up, the wisps of wind playing with her hair like a lover. They flowed around framing her face like a painting. Her beautiful eyes focused on me. Is she blushing?

Man! How am I supposed to stay cool when she looks at me like that?

Then she smiled that smile I loved.

#pokemon fanfiction #ao3 #fanfic #Grimsley #self insert #self insert fanfiction #pokemon #pokemon bw #one shot

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