Ash was currently helping Roxanne with her beginner's class at the Pokemon Trainer's School. It was the day before his gym battle with the rock type trainer and he wanted to get to know her better before that. They were currently sitting inside while the children were out at recess. "So Roxanne, how did you end up becoming a teacher?" Ash asked the Rustboro native. "I've always believed that young kids are important to the future of our world." She began, "If we educate them well enough they will do great things in the future". Ash laughed softly as Roxanne took some books off the shelf and walked over to him. "What's so funny?" she asked, a bit annoyed that he would laugh at her dream. "It's just that is something I have found to be true over the course of my travels." he responded, thinking about all the young kids he met and how eager they were to learn about pokemon. "He doesn't think its weird" Roxanne said to herself "Here start laying a book on each desk." she ordered, handing him a stack of textbooks. "Sure thing" he responded, starting to lay them down on the desks. It was at this moment they heard a loud explosion coming from outside. "What was that" asked Roxanne, looking out the window only to see smoke covering it. "I don't know, but we better make sure the kids are ok." said Ash. Roxanne nodded and the two of them dashed down a flight of stairs and out into the smoke. "Tailow gust" Ash ordered releasing the hoenn flying type from it's pokeball. The small bird immediately released the attack and cleared the playground of any particulates in the air. Roxanne gasped as she saw two strangers and a Meowth holding several of the school's pokemon hostage, along with Ash's Pikachu.
"Get back here you three." shouted Ash, as he ordered Tailow to go after the balloon. "Nosepass use gravity" yelled Roxanne (I know it can't learn gravity naturally but I need it for the story), releasing the compass pokemon. The rock type used the move to launch the gym leader at the balloon, shocking everyone in the vicinity. "How dare you steal pokemon from this school" she growled, landing in the basket of the hot air balloon. With a quick flick of her wrist, she sent out Geodude who broke the captured pokemon out of their containment. "No the boss's pokemon." Squealed Jessie, who back handed Roxanne out of the basket. The gym leader began plummeting towards the ground at a fast rate but was caught right before contact by a sliding Ash. "Are you ok?" he asked the gym leader, whose face was inches away from his own. "Yes I am" she stuttered in response, "he's so handsome" she said to herself as Ash placed her on the ground. "Alright, Pikachu thunderbolt" he yelled, "Nosepass Zap Cannon" Roxanne added. The two pokemon nodded before firing the electric attacks straight into the hot air balloon causing it to burst and send Team Rocket flying away. "Looks like Team Rockets blasting off again" the trio yelled in synchronization, disappearing into the sky with a twinkle. "Wow that was amazing Ms. Roxanne." one of the students exclaimed, "You were awesome too Ash" another cheered. It was at this moment that May and Brock came barreling around the corner having just finished lunch. "Did we miss anything?" the Petalburg native asked. "Just the standard Team Rocket attack" her brother responded at his position with the other students. "Yes well I think that is enough recess for today. Everyone back inside, its time to learn some more" Roxanne shooed the children back inside. Their lesson continued as normal and the school day ended with Roxanne, Ash, and Co bidding the students farewell. The gang was bout to leave but Roxanne called them back and invited them to dinner for seven o'clock. "Thank you for the invitation" said Ash, "Where is the restaurant"? Roxanne scribbled down something on a piece of paper and handed it to him "It's a nice place so try and wear nicer clothes ok" she laughed, patting him on the shoulder and taking an apple from her desk before heading out the door. May was ecstatic that they wouldn't have to pay for a meal in the city and began jumping up and down with excitement.
"I've got to get clothes" she laughed, as they walked back to the pokemon center. "Luckily the center will rent out fancy clothes for contests so we can use some for the restaurant" Brock added. Ash was in deep thought, Roxanne had invited them out to dinner free of charge and no questions asked. He was trying to figure out her possible motive was when they arrived at the center. Going their separate ways, the four travelers showered and rented clothes for the evening. Ash had chosen a deep purple jacket with matching pants and a yellow belt. The four of them met up and unfortunately had to leave Pikachu behind at the pokemon center due to the restaurant's rules. They followed the address given to them by Roxanne to an ocean front restaurant near the lighthouse. "Ash, Brock, May over here" they heard Roxanne call from the far side of the building. They walked over and Ash's jaw nearly dropped. Roxanne was wearing a loose red dress that fell down to her ankles and showed off a bit of her cleavage where a gold chain was. "She looks really hot" Ash thought as they approached the waving gym leader. "This place seems expensive Roxanne, how did you get a reservation here?" he asked as they entered the restaurant. "Being the gym leader of a town does have some perks but teaching the children of Rustboro has more benefits." she started as they approached the podium. "Ah Ms. Roxanne, your reservation for five is this way." The waiter said, grabbing a few menus and leading them to their table. "I will give you some time to peruse the menu before you order" he said, leaving the five of them to sit and discuss their lives. Roxanne revealed that the Trainer School's influence has brought success to many of the families in the city and so the school's workers usually get things such as discounted rates at stores and high class dinning priorities. While this was going on Ash could not get the fact at how beautiful Roxanne was out of his head but was shaken from his thoughts when the waiter arrived. "Your order sir?" waiter asked. "Oh uh, can I get the Caesar salad and Pasta combo." Ash answered quickly as it was the first thing he saw on the menu. "An excellent choice, Ms. Roxanne usually gets this as well." the waiter revealed, as he began to ask the others for their orders. After he left, Roxanne began to speak with Ash. "So Ash does Pallet Town have a trainer's school?" she asked. "We don't have a trainer's school but Professor Oak runs a camp for would be trainers during the summer months." he revealed. "I learned an awful lot there and you are teaching your students the same things I learned when I was young". Roxanne paused for a minute to marvel at how Ash had loved his time in school "Well seeing your success as a trainer has given me high hopes for my students". Ash slightly blushed at this as the others joined in on the conversation. The food eventually arrived much to Ash's dismay, as he wanted to continue learning more about Roxanne. It turns out she indeed liked the salad pasta combo and had ordered it for her dinner. He dug into his own meal and found it to be absolutely delicious and considered it to be one of the best dinners he's ever had. His friends thought likewise and they thanked Roxanne, as she paid for the meal and turned in for the night as Ash was preparing for his gym fight the next day.
Ash woke up the next day and worked out the last few kinks in Pikachu's iron tail before the group of four headed to the gym at 4:30 pm for Ash's showdown. However during the actual match he could hardly concentrate at all, as he was too busy star-struck at Roxanne's beauty. Fortunately, he was able to snap out of it and barely clutch out the victory in dynamic fashion. "Well done Ash" Roxanne congratulated the trainer, handing him his badge. "You almost had me there. Thanks for the great battle" he answered back, taking the symbol of his victory. "Say Ash do you want to help me with classes tomorrow?" she asked hopefully. "I don't know. I mean May's contest is in two days and I was going to help her prepare." he debated. "Go on Ash, I'll be alright." assured May from the stands. "Alright count me in." Ash smiled, shaking the gym leader's hand. As he walked back to his friends Roxanne turned around and headed back to her house "Tomorrows my chance to tell him my feelings." she said to herself. The gym leader began to start planning for the next day in order to impress the Pallet Town Native. Ash woke up the next day and was eating breakfast with his friends when they struck up a small conversation. "So where are you going to be training today?" he asked May who was currently digging into some cereal. "I was hoping to stay around here to train and hopefully pick up some pointers from the other coordinators." she revealed. Ash could understand where May was coming from with this decision. Pikachu also was interested in watching May train so Ash decided to leave him with her. It was May's first contest after all and she would need all the help she could get to be presentable. He then split from his friends and headed to the trainer school to meet with Roxanne. When he saw her he was once again speechless at her looks. She had forgone her normal pink stockings and wore high heals with her skirt. Her bare legs looked stunning in the sunlight and Ash was wondering why she kept hiding them with stockings in the first place. "Ash have you had breakfast yet" she asked, holding an apple out to him. "Yeah I was able to pick some up at the pokemon center before I came. Besides I don't really like apples that much" he assured the teacher, who looked aghast at his reveal. "Do you always bring an apple with you to the school" questioned Ash. "Yeah I eat it after classes are finished as a quick snack before I have to go to the gym" she laughed as they walked up the stairs to her classroom. Ash was rummaging through the closet when he pulled out what appeared to be a wooden paddle. "What's this?" he asked Roxanne. "That was used as discipline for students a long time ago" revealed the gym leader, taking it from Ash and setting it besides her desk "Although I keep it out for intimidation once in a while". The day went by the same as the previous time Ash was in the school. However something was off about the way Roxanne was acting. During the course of the day she kept angling her ass towards him a random times. It was almost as if she was teasing him but Ash couldn't figure out why.
Eventually the final bell rang, signaling the end of the school day and the children filed out of the room. Ash began to get up to leave but was called back by the gym leader. "Just wait one moment Ash" she called, walking over to him. Well she more like backed over towards him, once again showing her large and sexy buttocks. "Roxanne, you have been acting rather strange today. Are you feeling ok?" he asked the woman, while trying to stave off an erection that was slowly forming. "I'm just fine Ash but you look a little red. Are you sick?" she prodded, placing her hand on the blushing teen's forehead. It was at this moment Ash smelled something akin to apple coming from Roxanne's face. " No I'm feeling alright, but what's that apple smell?" he asked. "My lipstick, would you like a taste?" she revealed. "Wha, what?" stuttered Ash before he was enveloped in a kiss by the teacher. Ash was taken back by this as Roxanne released the kiss a stared into his eyes. "So how did it taste?" she asked the stunned trainer, "Why would you do this to me?" he quivered. "Because your passion for learning has gotten me to love…" She was interrupted as Ash grabbed her face and pulled her in to a searing kiss. The couple stayed this for several minutes only to break apart when they felt the need to breathe. "Wow" Roxanne breathed out, breathing heavy breathes to get air. "I feel the same way about you" Ash whispered before the couple resumed making out. The pair of the fell against the door, shutting it closed. Ash also sneaked a hand around and locked it to make sure prying eyes wouldn't disturb them. They duo made their way over to Roxanne's desk where Ash pushed her against it and continued to make out with her. What he failed to notice was the large wet spot forming on the front of Roxanne's skirt. Eventually the two of them broke the kiss and started panting. "I think I'm in love with you Roxanne" Ash whispered, placing a hand on her cheek. "And I as well Ash, but you need to prove it to me." She responded. "What more could I possibly do to show my love for you" came the reply. "Simple, I need you to eat this apple." answered Roxanne holding the red fruit that was on her desk. "I can do that for you my love." Ash laughed, reaching his hand out to grab it only to have his hand smacked away by the gym leader.
"Na ah, no hands. And you have to get it from here." Roxanne order, lifting up the front of her skirt to reveal that she wasn't wearing any panties underneath. Ash's eyes nearly bugged out of their sockets as the Rustboro native slowly inserted the apple into her glistening pussy. It took a minute before half the fruit was fit snugly into her snatch awaiting removal from Roxanne's lover. "Go ahead Ash, eat the apple." she teased, rubbing her crotch over the slowly forming tent in Ash's pants. "If that is what you wish my teacher." he responded, getting down on his knees and putting his mouth to the apple. He found it unable to budge as he sunk his teeth into the fruit. "You'll have to try harder than that" Roxanne teased. Ash thought of a new strategy and started to nibble at the ends of the apple where it touched the teacher's silky flesh. "Ugh that's good, just like that my student" she whispered in pleasure and began to involuntarily thrust her pelvis forward into Ash's face. Roxanne began to cum as the stem of the apple would flick her clitoris with every thrust. The fruit absorbed some of the fluid causing Ash to taste it on his tongue as he was finally able to bite into the apple. "This tastes so much better now than it did before." Ash thought, as he continued to struggle against her inner muscles contracting around the fruit. He placed his hands on Roxanne's thighs and pushed outward, hoping to have the help of some extra force. With this action the apple popped free from it's prison and was caught by the trainer. "That was tremendous Mr. Ketchum" spoke a quivering Roxanne, "Now why don't you finish eating it while I get to work on removing your pants". The Rustoboro native bent down on the floor and began to remove Ash's jeans, which were holding his now hard cock. Ash took a few more bites of the cum-covered apple as Roxanne removed his jeans and boxers to reveal his thick member. "Dear Arceus its so big." she thought, standing up to look him in the eyes and perhaps enjoying her role a bit too much. "Now I want you to lay down on the floor and…" she was cut off as Ash spun her around and slammed her chest-first over the desk, pinning her hands behind her back. "Now the student has become the teacher." he growled huskily into her ear and pinched her clitoris. Roxanne let out a loud moan of pleasure, which was quickly stifled by Ash, who shoved the half eaten apple into her mouth.
"We can't have any of the other teachers hearing us now can we" he laughed, continuing to rub her sensitive nub. Roxanne let out a stifled squeal, squirting more of her sexual fluids onto the floor. "You've been a bad girl Roxanne. Walking around without any panties on." He teased the gym leader, rubbing circles around the outside of her pussy with his dick. Roxanne whimpered softly as pleasure shot through her body, turning the proud teacher into a quivering mess. "As your teacher, I will have to punish you" growled Ash, reaching over the woman and grabbing hold of the wooden paddle. The Rustoro native's eyes widened a felt a sharp sting as her exposed ass was struck with the paddle. She let out a scream, which was muffled by the apple as pain wracked through her body. It was at this moment that Ash drove forward with his cock and into her pussy bust right through her hymen. A small amount of blood dripped onto the floor as Ash sheathed himself into her snatch causing Roxanne to once again let out a soft moan. Ash began to slowly thrust in and out of her to set a pace. Sounds of wood meeting flesh could be heard in the room as every thrust came with a strike from the wooden paddle. He made sure to alternate which ass cheek he was striking so that it would only add to the experience and not injure the gym leader. After several minutes Roxanne got used to the pain and began to enjoy the feeling of being dominated by the male trainer. Ash sensed this and began to increase the pace of his thrusts and strikes causing the teacher below him to experience more orgasms as he drove deeper and deeper into her body causing her sensitive walls to clamp harder on his penis. "That's right, you're a bad girl who needs to be punished" he laughed and continued to strike Roxanne's crimson red cheeks. It seem liked an eternity before Ash felt a pressure build up in his core, signaling that is was time to release. "Alright my disobedient student here comes your final punishment." he roared. With one final thrust he drove deep into her cavern, touching the back of her cervix. Letting out a loud grunt he unloaded his life-giving liquid deep into her womb. He continued to cum as he pulled out, spraying the white liquid all over Roxanne's crimson ass. The two of them collapsed onto the floor as the apple fell from the gym leader's mouth. Roxanne let out soft mews as Ash began to kiss her abused ass. "That was wonderful." She whispered, "I never thought I would like being dominated like that". Ash let out a small chuckle "It goes to show you that even though we teach others, we are still students". Roxanne smiled and turned over to place a kiss on her lover's lips "Let's get cleaned up in the school showers before anyone notices". "Alright fine with me, my friends might start worrying if I don't get back there soon" Ash responded, pulling her off the ground and putting on his clothes.
Eight Years Later
It had been a rather easy eight years for Ash Ketchum. After his punishment of Roxanne he continued on his Hoenn journey with his friends, eventually finishing in the top 8 of the Hoenn League. After parting ways with his friends he returned to Rustboro City to find a moderately pregnant Roxanne waiting for him. The two reunited and she revealed that the child she was carrying was his. Ash could not have been more overjoyed at this revelation and the two of them shortly married with Ash taking a job at the trainer school. Two months later Roxanne gave birth to twins, shocking the couple. A boy with his mother's hair named Rusty after the city in which they lived and a girl with her father's hair named Delia after Ash's mother. Over the past eight years the teaching duo turned the Rustboro Trainer School into the highest rated educational facility in the pokemon world. They ran classes ranging from begging trainers to graduate professors and did so together. This success brought them great riches and happiness to their family of four. Speaking of which, it was time to get the little ones ready for school. Rusty whined at his mother, asking why they had to go to class. She responded with a paraphrasing of her husband's words "Because dear even if your parents teach the class, we are all still students".