Pokemon First Kiss Headcanons


Ash and Misty’s first kiss was anything but serious, basically underage drinking happened and a very intense game of truth or dare. Most of their friends were around and also tipsy, and for some reason May, Dawn, and Iris got it into their heads that they should dare Ash to kiss Misty. The two comply, but in the most comical way possible, sucking on each others faces in the most unromantic way. This gets a lot of laughs from their audience and they say no more about it. A few weeks later Ash and Misty are swimming in the Cerulean City Gym’s pool and Ash casually brings up the occasion. Misty is mortified as she had little to no memory of that night due to her alcohol intake, so Ash teases her relentlessly about it, splashing water in her face and taunting her. Once Misty’s face was redder than a beet Ash asked her if he should remind her. This confused Misty since Ash was not in tune to romance or anything akin to it, before she could reply he gave her a proper first kiss, one that both of them would remember. They each tasted like chlorine and it was a little weird, but that didn’t mean they didn’t enjoy it, or do it again.


Drew recognized the fact that May was not the perceptive type when it came to love. He had been pretty damn obvious about it with the roses and everything so he decided to go for an even more direct approach. As had become their tradition over the years, whenever they met up while traveling they would go out for coffee or lunch (not dinner because Drew knew of May’s insane eating habits and did not want an empty wallet). One day while they’re both in the same town for a contest, after getting coffee Drew asks if she wants to take a walk around with him. May, bring May, accepts and is blissfully ignorant of his intentions. They’re walking through a park and out of nowhere Drew lifts her up off the ground, causing her to shriek, half out of surprise and half out of confusion. He then proceeds to press his lips against hers, May remains wide eyed and completely in shock. When he pulls away she demands to be let down, Drew smirks at her embarrassment and she orders him to never do that again. He agrees with mock sincerity and May storms off angry but sort of turned on. Needless to say he breaks his promise very quickly the next time they meet up.


In a moment of what Paul calls insanity, he sleeps with Dawn. It was a spur of the moment and heated decision, definitely would not be described as ‘making love’. They proceed to do it every so often, no strings or feelings attached to their midnight rendezvous. The only rule Dawn puts in place is that she doesn’t want him to kiss her on her lips as she finds the act to intimate for a noncommittal, purely physical relationship; Paul doesn’t really care and goes along with it. Everything was going fine until they started running into each other when they weren’t planning on having sex, in situations where they would actually have to converse with one another. Dawn soon finds herself attached, much to her dismay, and Paul now finds it awkward to sleep with someone he would consider a frequent acquaintance. Basically they both agree to call it off. They continue to run into each other, and during one of these times Dawn plucks the courage to talk to Paul about their former arrangement. He isn’t very communicative but Dawn persists, apologizing for the trouble it caused and making a sad attempt at explaining her reasoning. When she finally stops babbling the two look at each other and neither of them are sure who leans in first, but their lips slowly meet each other. Neither of them had a clue what they were doing so their lips didn’t move and their hands stayed by their side. When Paul pulled away Dawn hadn’t realized she’d closed her eyes. This begins a very tentative and careful relationship between the two of them.


Cilan knew of Iris’s crush on him, and Iris knew he knew and was pissed he did nothing about it. Never addressed it in the years they’d been friends and she’d liked him, not once. It was actually quite infuriating. In Cilan’s defense when he’d noticed Iris’s crush on him she had been twelve and he fifteen, hardly appropriate ages to act on such matters. Now with her eighteen and him twenty one he had no real reason to not mention it. Over the years they’d become best friends, they weren’t sure how it happened, but after she’d become a gym leader they found themselves always meeting up at events and the like. They’d talk on the phone often and send photos to each other. Over that time period Cilan had grown to care for Iris as more than a friend. She’d noticed it and it annoyed her to no end that he wouldn’t do anything about it, he was supposed to be confidant and outgoing and elaborately ask her out, but it never happened. Deciding to take matters into her own hands and took a plane to Striaton City, marched into the gym, and searched for her target. Cilan saw her and began to smile before he saw the pissed off look on her face. Cilan started to protest he hadn’t done anything but Iris cut him off wrapping her arms around his neck and kissing him. When she pulled away she chastised him for being such a kid and not having to balls to ask her out himself. On the spot he grows a pair and asks her to dinner. She accepts triumphantly.


Serena was susceptible to crushes, it was just the way she was. It never defined her existence or purpose but there was always someone that would come around and cause her heart to beat fast and her cheeks to flush. So once she had moved on from her infatuation with Ash, she was slightly surprised to find herself crushless. This went on for years as she furthered her career as a Pokemon Performer, it was strange but nice to not worry about impressing someone all the time. When she’s fifteen she has a performance in Luminose City, and simply has to meet up with Bonnie and Clemont before she leaves since they hadn’t seen each other in person for a few years. When she arrives at the gym a familiar feeling pierces her chest when she sees Clemont working on what she suspected was another one of his inventions, completely covered in grease, with messy hair, and his glasses falling of his face. She shakes it off quickly and greets the two siblings. After a few hours of hanging around in the gym and goofing off her’s suspicions are true, she has broken her streak of not having crushes. She eventually has to leave but before she does she makes a spur of the moment choice to have confidence in herself act on her infatuation instead of being silent like she had on every other occasion. Serena delivers her goodbyes to Bonnie and before Clemont can get a word out, she kisses him quickly and asks him to call her more often. He’s embarrassed and so is she. Neither of them know where it will go, but they take it slow and eventually one kiss leads to many more. Bonnie is thrilled.


Both of them are around six. Ash is sick in bed with a cold so they both are left to their own devices and one short one playmate. Gary and Leaf decide to explore Professor Oak’s backyard, aka the best playground ever for children who love Pokemon. As usual they get into an argument and without Ash to mediate their squabbles it makes it harder for the two to agree on things. When they reach the mutual understanding that wading in the river would be much more exciting than climbing trees for the umpteenth time, they finally have a mission. When they reach the calm river, sit on the side, and dip their toes in the cool water they notice the water Pokemon swimming about. The two spot a pair of Luvdisks kissing, and Leaf remarks on how she doesn’t understand why mommies and daddies do that sort of thing. Gary agrees with the sentiment, calling it gross but asks if she’d try with him as an experiment. Being the son of a scientist, naturally he’d want to test it to see if a reason could be found out. Leaf shrugs, not really caring either way, so they kiss each other, holding it for about five seconds before breaking apart in confusion. Leaf still doesn’t understand why mommies and daddies kiss and Gary has come to no conclusion other than kissing is overrated. Ten years later, that is not the case.

Pokemon Games - Evil Team Plots Breakdown

- Mt. Moon
- Cerulean City
- Route 24 (Nugget Bridge)
- Celadon City  (Game Corner)
- Lavender Town (Pokemon Tower)
- Saffron City (Silph Co.)
- Viridian City (Viridian Gym)

- Azalea Town (Slowpoke Well)
- Route 43 (Lake of Rage)
- Mahogany Town (Rocket Hideout)
- Goldenrod City (Radio Tower)

- Petalburg Woods
- Rusturf Tunnel
- Slateport City (Oceaninc Museum)
- Meteor Falls
- Mt. Chimney
- Weather Institute
- Mt. Pyre
- Team’s Secret Base
- Mossdeep City  (Space Center) *
- Seafloor Cavern

- Jubilife City
- Valley Windworks
- Eterna City (Galactic Building)
- Mt. Coronet
- Veilstone City
- Route 214
- Celestic Town
- Lake Valor
- Lake Verity
- Lake Acuity
- Veilstone City (Galactic HQ)
- Mt. Coronet (Spear Pillar)
- Distortion World *

- Accumula Town
- Striaton City (Dreamyard)
- Wellspring Cave
- Nacrene City
- Pinwheel Forest
- Castelia City
- Nimbasa City
- Driftveil City (Cold Storage)
- Chargestone Cave
- Mistratlon City
- Twist Mountain
- Iccirus City (Dragonspiral Tower)
- Desert Resort (Relic Castle)
- Tubeline Bridge
- Opelucid City
- Pokemon League (N’s Castle)

- Flocessy Ranch
- Virbank City
- Castelia City (Castelia Sewers)
- Nimbasa City
- Driftveil City
- World Tournament (Plasma Frigate)
- Lancousa Town
- Opelucid City
- Route 21 (Plasma Frigate)
- Giant Chasm (Plasma Frigate)

- Glittering Cave
- Route 10
- Kalos Power Plant
- Poke Ball Factory
- Frost Cavern
- Lysandre Labs
- Geosenge Town (Flare HQ)

- Hau'oli City
- Berry Fields
- Verdant Cave
- Route 5
- Route 6
- Diglett’s Tunnel
- Memorial Hill
- Akala Outskirts
- Route 10
- Malie City
- Route 15
- Route 17
- Po Town (Shady House)
- Aether Paradise
- Exeggutor Island
- Ultra Space

* = Third version only.

My opinion on the quality of these plots are as follows:

Plasma = Skull > Galactic > Rocket > Neo-Plasma > Aqua/Magma > Neo-Rocket > Flare.

In Retrospect

“So how long have you two been together anyway?” May asked, leaning earnestly toward the couple sitting across from herself and Drew. The couple–Cilan and Iris–had only just met the two Hoenish trainers through Ash, who had run off with Pikachu to pick up some food for their get-together–leaving his four companions alone to converse.

Cilan pressed a hand to his chin, thinking.

“Certainly more than a year now–almost a year and a half, I think,” he soon answered.

“Pretty short time to be dating before getting engaged,” Drew remarked, a little dryly.

“Yeah…” Iris trailed off. “I’d normally agree, but we’ve been friends for so long that I guess it didn’t matter. We traveled with Ash… eight years ago?”

“Eight years,” Cilan confirmed.

“Ohh, that’s sweet!” May cooed. “I love it when people are close friends, and then they fall in love! When did you know?”

“Know what?” Cilan inquired.

“That you were in love!” May exclaimed, as if it were obvious.

Iris and Cilan exchanged a quick, wondering glance, and Iris lazily flicked her wrist toward him, giving him the go-ahead.

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anonymous asked:

"wait who's Misty?" Pokeshipping fic w/ one sided amour only on Serena's end. :)

The Kalos group were currently enjoying the start of a nice lunch break beside a local river on the way to their next destination and, at the same time, had decided to take advantage of the opportunity to learn of more adventures and things from Ash’s past.

“Oh, well, I can always show you some of the pictures my friends and I took!” the raven-haired trainer had exclaimed with a guffaw, already plopping his backpack on their compact table to pull them out. “C’mon Pikachu!”

“Pikaaa!” the electric mouse cried in glee as he pounced after his trainer.

“Sounds like fun!” Clemont agreed with a nod as he started setting up the campfire with all of his necessities. “You’ve been traveling around the world a lot longer than the rest of us. It would be nice to get to know some of the people and Pokemon you’ve met outside of Kalos, wouldn’t it?” he asked openly towards Bonnie and Serena.

“Mm, sure!” the Pokemon performer nodded affirmatively as she started setting up the table, carefully moving Ash’s abandoned backpack out of the way while he ran over to the Lumiose City natives and sat down beside them.

“Hehe, feel free to come join us whenever you’re finished, okay Serena?” he asked with the same charming smile he always did, leaving her chest fluttering and burning in its wake.

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Cilan, Chili, and Cress

The triplets who run possibly the most unique Gym seen in the series since Tate and Liza. The Striaton Trio are known for their distinct culinary talents as well as their battling skills. Trainers in the anime must battle all three in order to recieve a badge while in game the player only battles one of the brothers, decided by the starter Pokemon they picked. The hot headed Chili specializes in Fire Types, while Cilan’s specialty is Grass and the graceful Cress uses Water Types. It is worth noting that the brothers stepped down from their titles of Gym Leaders during the two year gap between Black/White and Black2/White2, converting the gym into a regular diner. However, battles are still welcome and common.

*Gif not mine*

A breathtaking piece of imagery, the conceptual illustration for Striaton city evokes a sense of wonder, beauty, and the thrill of open adventure, look at that archway, it’s as if it’s inviting you into the open, verdant arms of that open fields, waiting for you to challenge the wilds and continue onward toward your Pokemon journey in Unova. This is so far one of my favorite pieces, very gorgeous imagery, a far cry from the map layout for the actual city ingame, isn’t it?

007: Butts

A note for all you knuckle-dragging, perverted little thunder-cunts. Stop staring at my butt.

Yes, I have a nice ass. Yes, my jean shorts comfortably hug it in a noticeable way. And yes, when I throw a Poké Ball my rear end thrusts out ever so slightly as if to suggest an invitation to a very sexy and exclusive butt party.

But you are not ready for this jelly. This baby’s back is not for you. I wear shorts because I like shorts. And it’s hot. TEMPERATURE HOT. I throw my pokémon out like an enthusiastic stripper because it achieves the greatest velocity for the minimum effort - and it looks badass. And most importantly, I’m like 14 years old. Probably. Maybe. Do you know what they do to paedophiles in Unova? No, me neither. I bet they put them in some sort of prison made of robot pokémon. Anyway, something bad. With robotic penises. Yeah.

Striaton City Gym is weird.

The whole thing looks like one of those terrible family restaurants. And all the trainers are waiters. Everyone keeps coming at me like they’re serving the pokémon as side dishes. Do you want me to EAT your fucking pokémon? Do you? Ugh.

It has three gym leaders, but you only fight one of them. They decide who you have to fight based on the best way to dick you around. Because I chose a Tepig I  got to battle some dandy assbite called Cress, who has hair made of disgusting blue worms.

Cress went on about being super awesome at water pokémon like a wanker, then sent out… a Lillipup. I set it on fire.

Then he sent out a Panpour. Panpour look like blue monkeys with giant puckered sphincters sprouting from their heads. And they are water types, so Pigface was shit out of luck. I sent in Broccoli like a champ, and he promptly fainted. Devil was no help at all, and Citizen K barked.

So Pigface was recalled, and used his “being a pig who don’t take no shit” attack. Victory! But it was a close one. Brute force told strategy to go and sit in the fucking corner. Pigface also learned Flame Charge, which I hope involves sending an army of fire towards the enemy, while playing a bugle.

And I got the Trio Badge, which makes a great impromptu shiv if I ever get in a bar fight.