Fly with Me One Last Time

"U-Urgh..."

Hilbert retched as he ran to the nearest corner of the Unova Region's Mistralton Gym, before emptying his stomach out, the boy's body obviously not agreeing with the ridiculous amount of air travel required to traverse through the harrowing facility. Taking a napkin from his pocket, he wiped his mouth, before angrily balling it up in his hand and tossing it at the mess he made. Muttering to himself, Hilbert took a deep breath and readied himself to be loaded into the next cannon. He had come here to win the Jet Badge from Skyla, not be tossed around like a circus performer while being shot through hoops! Who thought it would be a wonderful and completely safe idea to have cannons in a gym?

"Dumb bitch, we'll see if she's still "Highflying" when I kick her ass..."

BOOM! went the cannon as it sent him on its course, the trainer landing in front of yet another one as he hit the platform upon descent. Grumbling, Hilbert looked around the gym, horror in his eyes as he realized he'd used every cannon but this one.

"Oh, you can't be serious... This one's gonna shoot me all the way over THERE?"

A nearby Pilot trainer chimed in, a cheery smile over his face as he saluted Hilbert.

"Yep! You'll have to beat me first though!"

One minute later, Hilbert returned his Samurott to his Pokeball, the Pilot's blue uniform ruffled as he comically laid in a heap with his bottom in the air, easily swept aside with little effort. Hilbert only gave a condescending snort as he turned away from them and stared at the cannon, then upwards at the platform where Skyla stood. He shrugged his shoulders at the fear swirling inside of him, the trainer confident that nothing could make things any worse than they already were. Crawling into the cannon slot, he felt his knees shake as he waited for the launch.

"Well, I've already thrown up, so what do I have to worry abo-"

As the cannon lowered and fired the trainer, Hilbert's eyes grew wide as he realized he was being shot straight at a wall, and before he could do anything to prevent a head-on collision, his face met the cold steel of the gym. Slowly sliding down the wall, moans of agony and rage could be heard from the trainer, until his body suddenly detached itself, sending Hilbert falling onto his back on the hard gym floor.

It was a while before he rose from his location, but when Hilbert finally pulled himself up, the pure rage in his eyes would stun even a Zebstrika. Dusting his clothes off, he walked to the final cannon, and loaded himself up. The BOOM! of the cannon would be heard, and Hilbert whizzed through the red ring that hung next to the Flying-type Gym Leader. The ginger-haired girl would smile and wave as she saw her challenger land in front of her, giving her introductory speech with a giggle, but would be rudely cut off by an irritated Hilbert.

"Hee-hee! I've been wait-"

"Can it you bitch."

Skyla gave a confused look as Hilbert pulled the cap over his head, the barely visible slits of his eyes giving off an unnerving glare. She'd wave her gloved arms in front of her, trying to get his attention as he stepped forward closer and closer.

"W-Wait, what are you-"

Skyla screamed as Hilbert grabbed her by the shoulders and pinned her body against the wall, the Gym Leader struggling to breathe as her face was pressed tightly into the metal. Hilbert would then use one of his hands to drag the shorts off of Skyla, the girl protesting and struggling futilely against his hold. Her Pokeballs would fall from her pockets and scatter on the floor, the Pokemon inside giving worried cries as they were separated from their trainer. He'd give a smile at her vain efforts to try and break free, pushing a finger into the front of her panties where her vagina lay. As Hilbert basked in the resulting moaning, he'd rub the erection in his pants against her ass, giving it a slap. Skyla managed to move her head away from the wall momentarily to give Hilbert a pleading look.

"S-Stop, w-what do you think you're doing to me!?!?"

His reply was a slap to her face, the sting of the blow leaving a red mark on Skyla's cheek. Tears began to well up in her eyes as Hilbert pulled down the panties covering her cunt, the Gym Leader's folds having a visible line of wetness from Hilbert's earlier fingering. Hilbert undid his own pants with a sneer, the perverted trainer ready to make her his bitch. Prodding Skyla's inviting hole with his dry cock, she cried out as he chafed her insides, the Highflying girl internally wishing he would at least leak pre as quickly as possible to ease her suffering. She did her best to cope with the pain by clenching her plump cheeks on Hilbert's girth, but his wild bucking still caused her agony as he pounded her backside without remorse. Skyla's breasts bounced into her face as he suddenly pulled her down onto her knees, hounding her with thrust after thrust as she was now forced to kneel for his doggy-style desires. Try as she might to break free and run, his arms were grasping her shoulders, preventing her from so much as moving her arms. Skyla's tears began to fall as he continued to tear into her walls, the excruciating misery making her feel light-headed.

Miraculously, Skyla would begin to feel his pre begin to enter her, and now she could at least bear the vicious fucking Hilbert was giving her. His cock would now smoothly slide into Skyla's deeper areas as she relaxed her hold on him, the Gym Leader's abdomen now sporting a bulge from the girth pushing into her. Hilbert gave several grunts as he gave her another spurt of pre, the trainer edging closer to his orgasm, but wanting to drag it out for as long as he could just to further humiliate her. Giving her thick ass another spank, he pulled Skyla towards him, before using her like a toy, pushing her back and forth onto his penis until it finally gave in to the teasing as Hilbert planted his seed into the Gym Leader. She gave a shriek of horror as she felt the semen shoot inside her, the warm fluid making her feel disgusted and shocked that this trainer had actually fucked her in her own gym. Hysteric, she began to stand up for herself, wild fury in her blue eyes as Skyla shook in Hilbert's hands.

"H-How could you do this to me?! I'm a virgin! I was saving myself for someone who'd be a lot better than yo-"

Skyla was cut off as Hilbert suddenly grasped her sides and turned her body over, a crazed look in his eyes as his tongue came out of his mouth to lick his lips. She'd be frightened of his gaze, lying still on the ground as he grabbed the panties that were around her boots and pulled them off with a grin. Hilbert gave them a sniff, inhaling her scent with a perverted shudder, before he lowered them to his crotch and began to wipe the wet cum off of his cock.

"Well, if you're a virgin, the least I should get for having to go through this hellhole is your sweet, sweet virginity."

Skyla's eyes went wide as he gave his member one more wipe before tossing her panties aside and pinned her once more, his arms and legs holding her down as he touched the tip of his cock onto her cunt. Skyla gave a cry as she felt him penetrate her mound, the hymen covering her folds popping and making a mess on both of their genitals. That didn't slow down Hilbert in the slightest however, as the trainer kept pushing inward, giving an excited laugh. Once he was satisfied at how deep he was in her vagina, Hilbert moved one of his arms to fondle Skyla's breasts, the Gym Leader crying as her mammaries gave off a few drops of lactation.

"Stop this! STOP IT! You're not gonna get away with this!"

Hilbert ignored her screams, chuckling to himself at her distress. He put his hand to her chin and squeezed her face, silencing Skyla as he glared at her.

"You seem to have forgotten that I've beaten every trainer in your Gym. Face it, there's no one that'll save you. So shut up and let me enjoy myself in this place for once."

With that, he gave her cheek another slap, the red mark from earlier growing darker as he began to hump the now lifeless Gym Leader. The Flying-type user was fazed at his statement, knowing it was true. Someone would've come to her aid by now if they could. After all, she had bonded with with each and every one of them. And now, this monster had taken out all her friends, and taken her virginity. There was no hope left for her.

Compared to how she was before, Skyla was a shell of her former vibrant self. She didn't fight back. She didn't yell at him to cease his actions. All she did was lay there with a blank expression. Hilbert obviously enjoyed this version of her more, as he thrust into her with more enthusiasm, drool running down the side of his mouth as he panted. He slapped her face again as he taunted her, demanding an answer for her sudden lull.

"What's wrong? Have you finally come to your senses and given up?"

Skyla just laid there, and Hilbert growled as he humped into her cunt, his balls begging for a release as they slapped against her. Using each hand to grab one of her breasts, Hilbert moaned as he burst into her womb, the enormous amount of cum overflowing out onto himself. Skyla remained emotionless as he pulled out of her, and Hilbert gave a triumphant snort.

"Like they say, an eye for an eye. You fuck with me, and I'll fuck with you."

Hilbert pulled his pants up, giving Skyla one last glare before he turned around and exited the Gym, leaving the Flying-type user to lay there in a pool of his own body fluids. He walked to the nearby Pokemon Center and called the Pokemon Association from the payphone next to the counter. He filed a report on Skyla's gym being too dangerous for trainers to earn Gym Badges from, and demanded an investigation into who allowed Skyla the potential to harm her challengers with life-threatening injuries.

Some time later, the Association sent agents to the Gym, and they discovered the Gym Leader still laying there where Hilbert had left her. The Gym Trainers surrounded her in a ring, trying their best to comfort her and snap her out of her trance, but there was nothing they could do. The agents forcibly made the trainers step aside, knocking away food trays and memorabilia shrines set up for her. Skyla's Pokemon stepped in front of her unmoving body, but the agents simply called out their own Pokemon and knocked them unconscious, each of the Leader's Pokemon then being recaptured one by one until the agents finally stood next to her. The agent in charge read Skyla the charges Hilbert had filed against her and her Gym for negligence and reckless endangerment, and that as a result, everything she owned would be repossessed, from her status as a Gym Leader to the clothes she wore. Skyla said nothing as they stripped her of her partners and her outfit, the now naked trainer being carried out of the gym amid protests and cries from the Mistralton trainers.

Left on a bench outside the city's airport with nothing but a blanket a passing Samaritan had generously given her, Skyla looked up at the white clouds dotting the blue sky, before sobbing and putting her head in her hands. Internally broken, and having nothing left, she was all alone. Until she realized, she wasn't. There was still something she had. A way out of this nightmare. A smile growing on her face, she giggled and set off for her last journey as a trainer.

---

Skyla marveled as she stood on one side of the Driftveil Drawbridge, seeing the flocks of Ducklett and Swanna flying through the air before they flapped their wings and landed in the water below. The soles of her feet were callused and she hadn't eaten in days, the former Gym Leader's body worn out from her long journey. Her current state didn't bother her however, for here she was, at her final destination. Clenching her fists, she threw the ragged blanket off of her body and jumped off the lofty edge, a smile on her face as she screamed, "I want to fly away with you!"

The local police soon discovered her body hours later after receiving multiple calls from people who had witnessed her plunge. The Driftveil newspaper ran a story the next day about the incident, the title being "Mistralton's Ex-Gym Leader Dies Wanting to Fly with Pokemon One Last Time".