Ash and his friends walked away from the Fortree Gym. The gym leader Winona was not there at this moment and was currently helping with the city's feather carnival. They group of four walked through the streets of the city, taking in the sights and sounds of the different stalls when they heard a loud screech. Looking up in the sky they saw a large silver bird gliding through the air.
"That's a Skarmory." said Max enthusiastically.
"And a pretty big one from the looks of it." added Ash.
"It looks like there is a person riding it" Brock pointed out.
The other three squinted and were able to see a figure on the back of the flying and steel type pokemon. "Wait what are they doing" May asked, as the figures swung their legs over the Skarmory's back and dangled them above the ground.
"Dear Arceus." Ash whispered, as the figure jumped from the flying type.
May screamed out in horror as the figure began falling (earning some weird looks from the natives), only to be silenced as the figure spread their arms to reveal a wingsuit. The figure began gliding back and forth across the sky at a slow pace until it was revealed that this figure was the city's gym leader Winona. "Why would she put herself at such a risk?" Max asked the group, as they approached where the girl was going to land.
"She's an adrenaline junky and loves the rush of flying through the air." a local answered as they all ended up circling the young lady as she landed.
"Interesting, she must love flying so much because of her pokemon." concluded Ash, while the rest of the group and citizens clapped for the landing.
"Thank you, thank you." the girl laughed, pulling the helmet she was wearing off of her head to reveal her lavender hair. "
I do have to admit she does have pretty hair" thought Ash, blushing slightly. The four of them waited for the city residents to start clearing out before they approached Winona. Ash stuck his hand out and introduced himself. "Hello, my name is Ash Ketchum and I am challenging the Fortree City Gym." he revealed to the young lady.
"I am pleased to make your acquaintance Ash. I will set a time to battle at 3 pm tomorrow if that is okay with you." she responded.
"That would be wonderful" he answered back.
"Speaking of which, since you guys are not from around here, would you like to try gliding?" she asked.
Ash looked at his friends who all had excited grins on their faces at the prospect of doing this activity. "We'd love to, but where would we do this?" questioned the trainer.
"Since I do this a lot, I installed a training facility inside of the gym to help newcomers learn." revealed Winona.
Winona walked back with the group to the gym before she began to teach them the basics of the sport. The four travelers absorbed the knowledge taught to them by the gym leader and after being tested, it was decided that they could be fitted into wingsuits. Brock was fitted into a brown one, May had red, Max had green, and Ash had a deep blue color.
Winona joined them for a training session inside of the gym where the floor would open up to reveal giant fans, allowing people to glide back and forth across the building. "Climb the ladder up to the platform so I can explain the safety regulations." ordered Winona, who was already up there.
While Ash's other friends climbed the ladder with relative ease, the boy trainer was having a harder time. The suit that he was given was a little different from the others. It seemed to be made thicker than the others and tugged tightly against his body. So much so that his crotch was almost visible from the shear tightness of the suit. This of course made it difficult to move on the ground and was the reason he was struggling with climbing the ladder.
"Ash are you ok?" asked Winona as she pulled him onto the platform from the ladder.
"Yeah I'm ok" he responded, getting a good look at Winona's suit and turning away to not reveal his blush to the others. Winona's suit really brought out the features that made people think the Fortree Native was attractive. The suit looked like it was made out of the same material as his own. This tugged tightly against her breasts, showing their outline clearly and defined. It also displayed how beautiful her ass was, with the suit wrapping around her cheeks gorgeously.
Winona began to reiterate what the group had learned about wingsuits before turning on the fans with a flick of a switch. "Why don't you let your flying pokemon out to enjoy this" suggested Winona, releasing all three of hers. Ash complied and sent his Swellow out of it's pokemon, who immediately began to enjoy the action. Ash took a deep breath before diving off of the platform and into the jetstream.
"This is incredible." he thought as he began zipping around the gym.
"Wow, he's a natural." thought Winona as she was helping the struggling Max and Brock in the air.
Ash was performing so well that he was able to do spins while moving forward. This caught Winona's attention even further and a small blush came to her face. Meanwhile, Ash could see that even though his suit was hard to move with on the ground, it was a completely different story in the air. The suit had several pocket patches that allow for less drag than his friend's suits. These were placed along the shoulders, chest, and ass for a full body reduction. While the humans were flying around, the two Swellow had got rather close to each other. Winona's bird was very interested in Ash's and they were doing a small mating dance that went unnoticed by the humans par Winona.
The group flew around the room for about an hour and a half before Winona decided that it was time to leave and offered to take them out to dinner at the festival. May immediately said yes and Ash had to accept the courteous offer the gym leader made. The restaurant Winona took them to was built into a tree and they had to climb a ladder to reach it.
Once inside Winona talked about how the city was built around the architecture of trees and even the stone buildings have a tree feel to them. "That's incredible, it must be nice to feel so connected with nature." said an appreciative Ash.
Winona took note of this "I wonder…" she thought and began telling the group about her life growing up and how she became interested in flying pokemon.
"Is that why you love using wingsuits?" Max asked.
"Yeah, I just love the feeling you get when the wind rushes past your body and the freedom you have in the air" explained Winona.
"That is an idea I can get behind" added Ash before ordering his food.
The rest of the dinner went rather smoothly with the group revealing more about themselves to Winona as the night went on. Once they were all finished, Ash and his friends thanked the gym leader for the meal and headed back to the Pokemon center so that the Pallet Town native could plan for his battle taking place the next day. Winona went back to her house and removed her wingsuit, placing it in the washer. While taking a shower, she began to have thoughts about the boy she would be battling tomorrow.
"I'm glad I gave him the V-suit. He looked extremely hot in it and he also seems to share similar beliefs about flying" she said to herself as she clean her body. "He is also a very caring and compassionate person. Maybe I should try being a bit more provocative to test his interest." she tried to reason. With her decision made, she began preparing for her battle with Ash in more ways then one. Eventually the young lady got tired and drifted off to sleep, hoping her effort in snagging Ash's heart would be successful.
The Next Morning
Winona woke up with the front of her nightgown soaked. During the night she had a really pleasurable dream involving a certain trainer and wet herself during her sleep. "This is really embarrassing" she said to herself and went to take a shower. It would be several hours before her battle with Ash so she decided to grab some breakfast before leaving for the gym.
Once there she participated in her daily training regimen in her suit before preparing for her battle with the boy she began to develop feelings for. "Am I really falling for him?" she asked herself "He's kind, compassionate, and really understands my passion for flying. If I miss this chance I will never forgive myself". She was broken from her musings by the object of her affection as he and his friends entered the gym.
"Winona are you ready for our battle?" Ash asked the gym leader.
"Of course I am Ash. It will be a three on three battle." She explained as her resident referee walked over to judge the contest.
"Alright Pikachu, let's go." yelled an excited Ash (The battle happened the same way as it did in the anime with Ash picking up the win). "Yes, we did it!" Ash cheered, running out onto the battlefield and giving his Swellow a hug.
"Congratulations Ash" said Winona offering her hand with the badge in it.
Ash thanked Winona, accepting the badge and putting it in his badge case. It was at this moment that the trainer asked her if he could come back later and use the wingsuit again. He explained that May was going to practice for the Lilycove contest so he figured he would get out of her hair. "That would be the perfect time to tell him." she thought, before saying that she would allow him to come back around 5:30 after the gym closes to the public. Ash accepted this and thanked the gym leader before heading out with his friends to grab some lunch. Winona sighed as she began to plan for the object of her affection to arrive later that day.
5:34pm Fortree Gym
"Hey Winona I'm here." Ash called, knocking on the front door to the gym. The door opened revealing Winona holding out the suit Ash wore the day prior.
"Wait where is your Pikachu?" she asked, handing him the wingsuit.
"Oh he is with Brock and May as they wanted his help with her contest moves" he replied, accepting the wingsuit and heading off to the locker room to get changed. A few minutes later Ash walked out dressed in the suit and released a now healed Swellow from it's pokeball. Winona followed suit and the two flying types bean zipping around the empty gym.
"Look at them go." laughed Ash.
"It is beautiful." Winona replied.
The two trainers climbed up the ladder and Winona pressed the control panel to turn on the fans. They both dived off the platform and into the airstream, catching up with their pokemon. During the hour of gliding Ash noticed that both Swellow were constantly doing flips and spins in the air next to each other. At the end of the session the two of them called in their Swellow and climbed down the ladder after turning off the fans. It was at this point that Ash finally decided to ask Winona if she knew what was going on.
"They are doing a mating dance." Winona revealed in a soft voice.
"Wait what?" Ash stuttered, drifting back a bit as the gym leader began to circle him.
"When Swellow find the bird they want to be with they go through a courtship involving skydancing." she added, approaching him slowly. "Once the dance is performed the Swellow will get really depressed if they are separated from one another and possibly even die" she revealed, now only inches away from Ash's face.
"But I can't leave Swellow here, we have a league to win." Ash gulped.
"Well, you could stay here as well." Winona whispered and kissed the young trainer on the lips. Ash's eyes widened at this unexpected reveal but his mind was going haywire.
"Dear Arceus she likes me too." he said to himself, accepting the kiss and allowing her tongue to enter his mouth. The two trainers moaned loudly as their oral fleshes battled with each other.
Winona took the upper hand and guided the two of them through a door that lead to her bedroom. They fell onto her bed and separated with Winona now straddling the boy's abdomen. "Do you see now Ash" Winona gasped, trying to catch her breath, "Like are Swellow, we are made for one another".
"Winona, you're beautiful and I do have feelings for you, but I still want to at least compete in the Hoenn League before we take these feelings further" He explained trying to move but was unable to due to the gym leader's weight and the suit restricting his movements.
"You will still be able to use Swellow. You they just can't be separated for more then 2 months." she revealed, kiss him again.
"That's a relief." Ash breathed a sigh of relief.
"Now what do you say we get more personal dear?" asked Winona.
"Will it be ok? Also, shouldn't we get out of these suits first?" wondered Ash.
"Don't worry, the suits just enhance the experience." Winona proclaimed, reaching over to her nightstand and pulling over four air-pump cables.
"What do you mean?" he asked as she connected two of the cables to a couple of the pocket patches of Ash's suit.
"Shush" she whispered, placing a finger on his lips and rubbing the outline of his manhood underneath the suit.
Ash groaned as his member increased in sized and the outline of his cock and balls could clearly been seen against the skin of the suit. There was a small zipper located right above this area and Winona reached her left hand to it while her right hovered over to the night stand and grabbed a bag. With a tug she pulled the zipper down to reveal the entirety of Ash's cock and balls covered by blue latex. The only piece of his skin untouched was the opening of his penis, which she then gave a small lick.
"Ash you may have noticed that our wingsuits were different than the ones I gave your friends to wear." Winona began. "They also double as vacuum suits when hit with the right amount of air pressure." she explained, hooking two of the cables into the patches on Ash's shoulders.
"What's a vacuum suit?" asked Ash as Winona pulled out a remote and a hood from the bag.
"Why don't you find out." she laughed, placing the skin-tight hood over his head so that only his mouth was exposed. Winona hit a button on her remote causing air to rush into Ash's suit and tighten the fabric even more against his skin.
Ash whined as Winona began to trace his body with her hands and began to make out with him, causing excessive stimulation due to his enhanced suit. "Does that feel good my dear." she asked as they broke from this kiss.
"Wonderful, I've never felt anything like it." replied the blind boy. Winona laughed and unzipped the small zipper on her groin to reveal her moist pussy lips. "I will join you soon my dear." she informed her partner before taking Ash's hands and sliding them into the pockets of his suit. Once they were inside, the air from the vacuum sucked his hands into place, binding them to the suit.
"What's going on" Ash panicked, trying to remove his hands.
"Shush dear, I'll make it better" Winona laughed, pulling the rest of Ash's hood down so his mouth was now covered. "Breathe through your nose." she informed the boy, who was gasping through the material for breath.
She took a deep breath and connected the other two cables to her shoulder patches before hitting another button on the remote. Winona let out a squeal as air rushed into her suit and increased her sense of touch. She spun around and marveled at her lover's hardened cock just begging to be touched. She bent her head down and took hold of the hardened member with her mouth and hands. She slowly pushed the latex covered phallus deeper into her mouth as she dragged her teeth across the material. Ash came right then due to the increase in sensitivity and flooded Winona's mouth with his white liquid. Winona could hear Ash's muffled breaths as she swallowed his essence and placed a kiss on his covered mouth.
"That was delicious dear." she laughed and positioned herself over his aching member. With a bit of force she impaled herself with his cock, tearing right through her hymen. She hissed in pain as a small amount of blood dripped onto Ash's suit. Said boy made a few noises of concern, but was silenced as Winona placed another kiss upon his latex-covered mouth. "I'm ok." she whispered and began to ride the man beneath her with renewed vigor.
Winona let out loud moans as Ash's cock penetrated deeper and deeper into her maidenhood. The latex fabric stuck and slid along her sensitive walls, driving the girl to near insanity from pleasure and had experienced her first orgasm of the session. She began to claw and bite at the boy beneath her in hopes it would alleviate the pure ecstasy she was feeling at the moment.
Ash was currently experiencing a new world as his cock was being sandwiched by his lover's velvety walls, with the latex merely amplifying his pleasure. The small nibbles and scratches were enhanced by the suit causing the poor boy to whimper in pain. However his sounds were quashed by both the suit and Winona smashing her lips to his mouth. Ash started thrusting upward to match Winona's movements and a pressure began to build in his groin. He made warning grunts as his dick began to twitch rapidly due to the gym leader's pussy clamping down with excessive force but his warning was taken in stride.
With a muffled scream he released his fluids into Winona's awaiting womb. Winona felt her stomach being filled up to the brim with her lover's cum. With a soft pop she removed herself from his groin and collapsed against his chest breathing heavily. She placed the other hood from the bag over her head stopping so that she could still speak. "Now it is your turn my dear" she explained, before pulling the rest of the hood over her face. In her blind state she slipped her hands into her suit's pockets, locking them into place like she had Ash's. She then inched her way along the bed like a Wurmple and pressed a button near Ash's pockets with her head. This action caused the boy's suit to release his hands from their confinement, allowing him to pull his hood off and get a good look at his lover.
"You look so innocent and helpless" he breathed out, rubbing the back of his hands over Winona's breasts, teasing the women. "Let's try something different." he whispered, nibbling on her rubber covered ear.
It was at that moment he picked up the helpless gym leader and pushed her against the wall. As he began to make out with her covered mouth as any excess cum from before fell out of her pussy. The gym leader made pleading sounds, pretty much begging for Ash to fuck her. However the young man would not give in and instead nibbled along her neck and breasts to tease the woman. Winonoa let out muffled screams of pleasure as she drenched her partners stomach and groin with her fluids in shear ecstasy.
"Well aren't you a naughty girl" said Ash, "Maybe I should punish the little bird".
With a squeeze of her ass cheeks he buried himself deep within Winona's snatch. If he had the ability to see the girl's eyes he would have observed them widening in surprise as he lifted her legs off the ground and wrapped them around his torso. He then began to pound away at her pussy, relishing the fact that he was finally in control. He resumed his nibbles along her chest and neck driving the girl insane as he drove deeper and deeper into her core. Muffled cries could be heard as Ash continued his rampage for 10 minutes before carrying the girl back to the bed. He had made his lover cum many times but he had been unable to achieve release. It was at this point he finally felt the familiar pressure building in his groin just begging to be released. With one final thrust his semen burst out of his cock and into his lover's awaiting womb. With this deed done Ash finally collapsed against Winona's body and turned off the suits with the remote. Lifting Winona's hood off of her head, he gave her a passionate kiss.
"That was even better than flying" she laughed. Ash chuckled at this remark and responded
"I need to get back before the others get worried". Winona nodded and gave him a kiss before helping him get changed. She didn't worry as he left the gym, knowing that he would be back because birds of a feather flock together.
3 Years Later
Ash was currently holding his young son Zephyr as his wife battled a challenger. After finishing top 4 at the Hoenn league Ash separated from his friends and came back to Fortree to meet up with Winona. The young lady was ecstatic for his return and immediately engaged in a passionate session, which resulted in the birth of their son. The Fortree City Gym was now thriving as not only a gym but also a wingsuit center. Ash was in charge of this part of the gym so his wife could focus on the challengers.
High above the gym floor, in the rafters of the roof was a giant nest for the couples Swellow. The two bird pokemon finally got to complete their mating ritual when Ash returned. Every year they would have two children, one shiny and one not to love and care for before they would be sent out on their own. Ash's flock was going to gain another member as it was revealed that his wife was again pregnant. He could only laugh at the great turn of events that happened in his life to lead him here.