It was the start of a new day, and Ash's first official step in becoming a licensed Pokémon trainer. Grabbing his schoolbag, as well as the hypnotic pen his step brother, Clemont gave him, Ash walked out the door to his first class. Seeing all the other students make the way out of their dorms and to the field they were scheduled to be at, Ash took notice of Serena, who strutted alongside her girl friends.

Joining his friends himself, Ash and his group were on a collision course with another.

"Hello, boys." Astrid said, waving to the group. "Ready to receive our first partner Pokémon?

"Bout as ready as I'll ever be, anyways." Trevor replied.

"Well, I know I'm gonna be the best!" Serena sneered, her confident personality once again raising questions among everyone but Ash.

"What's gotten into you lately?" Shauna asked. "You've been acting weird lately."

"Yeah, you're usual more...docile? Is that the word?" Clemont asked.

"It's something I want to prove to someone." Serena blustered, turning to Ash before she got in his face, surprising everyone, Ash included. "I wanna challenge the strongest guy I see among our group, and put down a bet."

"A bet?" Ash asked.

"What you don't remember?" She said, making Ash realize she was making a ploy to deceive the others. "When we met after PE the other evening. You said you'd do whatever I wanted if I beat you in the practical exam of our Pokémon training that's about to happen, remember?"

Realizing what she was getting at, Ash played along.

"Yeah, and if I beat you, you have to go on a date with me." He replied, shocking everyone.

"Huh?!" Shauna gasped, utterly perplexed. "Is that why you're acting weird, Serena? Is this some tough girl act?"

"Maybe it is..." Serena replied, being vague in her wording.

"But I thought you would want that?" Astrid asked. "I mean, going on a da-"

"Let's leave that for later!" Serena said, hastily elbowing her blonde friend from speaking. "See you in the ring, Ash!"

"Y-yeah..!" He replied, waving the girls goodbye as they went on ahead.

"What the hell was that about?!" Alain asked his friend. "Serena's never been so bold before."

"Guess my talk with her really fired her up." Ash replied.

"I always thought she had the hots for you." Trevor noted. "I suppose if this bet is set up this way, it's a win win for her. No wonder why she's brimming with confidence."

"I'll say!" Shauna said, reacting to Astrid's words describing Serena's attitude very much like Trevor did. "So, is it true then? You'll make him do whatever you say if you win? What devious scheme do you have cooked up."

"Well, you know I'm into him, I just can't find the way to express that." Serena replied, lying further to ensure her cover isn't blown. "At least this way, I can spend time with him either way!"

"I could only imagine what slutty acts you have in mind for him to do for you!" Astrid joked.

"Oh yeah, I have a few things in mind..!" Serena said under her breath, biting her lips for a moment, only to retreat back to a more meek personality. "O-oh, I mean, I'll probably just have him do things with me to spend time with me, and stuff! Like carry my books and stuff!"

"Oh, and stuff!" Shauna joked, taking note of the honey blonde's red cheeks. "You're blushing."

"Oh!" Serena replied, continuing to go back to her normal personality.

As the group of guys continued to the field, Ash began thinking to himself. He knew he told Serena that he needed her to make herself less conspicuous, but he had no idea that her mind was still free enough to adapt to the situation. Clearly, Ash needed more test subjects to understand the true abilities of his special pen. If he could make his subjects have enough free will and act beyond just his most literal commands, then surely such a feature in the device possessed far greater power than he realized.

Finally making it to the field, Ash and his classmates were met with Professor Sycamore, as well as Ash' first slave pet, Cynthia. Ensuring her cover, Cynthia simply acted as the class home room teacher, instructing the students on what they would do for the day.

"Ok class! Today, we issue you your first partner Pokémon!" Cynthia stated. "As you all surely know, it is a trainer's responsibility to control their Pokémon. Make sure it obeys your every command. Remind it that you are in control, not them. Doing this ensures the Pokémon more servile and open to suggestion."

Noticing her words reflected much of their own current relationship, Ash had a small grin on his face. His appetite for sex, between his two current slaves alone was immense. He could only fathom how much greater it would be if he got more beautiful girls to submit to him.

"Sycamore here will now provide you the option of your first partner Pokémon! With limited supply however, we will hand out Pokémon based off of trios. Three of you will step forth and decided who shall go first in picking their starter. After that, you will introduce yourself to your new partner. Grow accustomed to each other, learn about each other. After that, we will begin the practical exam by having two trainers engage in a duel which will be used as an education method, so don't worry about losing if you do, you won't be scored on your first performance."

"The first group to pick their Pokémon will be drawn from this bowl." Sycamore chimed in. "When you hear your name, come forth to chose your new partner!"

As the professor's handed fished into the opaque obsidian bowl, Ash and his friends were anxious and excited alike. Pulling his hand from the bowl with three slips in hand, Sycamore called out the three names.

"Clemont, Serena, and Ash! Come on up and chose who amongst you shall go first." He said, the three chosen stepping forth from the crowd.

"So, who wants their Pokémon first?" Clemont asked. "You may lose out if you don't wanna go."

"Nah, I'll let you go first, bro!" Ash replied, giving his brother a thumbs up.

"I don't really care who goes first." Serena replied.

"Then by all means, I chose this one!" Clemont said, pulling the pokeball on the right.

Suddenly, light emerged from the sphere, a Chespin coming forth.

"Ah, the grass type, Chespin!" Cynthia said enthusiastically. "A great choice for beginners."

"I guess I'll go next then." Serena said, grabbing the middle most ball.

Upon picking it up, a Fennekin jumped out of the ball, the Fire Fox Pokémon sneezing a burst of embers.

"The Fire Type, Fennekin! A Fire type is always a tough one to master, but I've seen your level of patience, Serena. I know you got this!" Cynthia cheered the honey blonde up, oblivious to the fact she was a fellow slave girl to her Master.

"I guess that leaves you." Ash spoke to the pokeball, the orb opening to reveal a Froakie, and a rather serious one at that.

"Ah, Froakie!" Sycamore spoke up this time. "That one is rather special. He's rejected several other trainers in the past before. He'll be a tough one to wrangle, but I'm sure you can do it, Ash!"

"Nice to meet you, Froakie!" Ash said kindly, reaching his hand out to the Water Type. "My name's Ash! I hope we get along well!"

"Froa..!" Froakie croaked, evidently not expecting such a friendly greeting considering the selfish and greedy trainers it turned down in the past.

Breaking away from the rest to continue their assignment, Ash, Clemont and Serena went on their own to meet their new Pokémon. Clemont and Chespin grew fast as friends, the tiny grass type proving how much of a clown and klutz it was, much like his new trainer. Serena and Fennekin proved easy going as well, with Serena grooming the Fire Type, much to her content.

Ash's new Froakie, however, seemed distant. He didn't show outright disgust or distrust, but proved to be simply apathetic, as if he was judging Ash. Sensing what his partner was seeking, Ash spoke to the Pokémon.

"You want to be strong, don't you?" He asked his Pokémon, the Water type taking note of his words. "You know the immense potential you carry, but you don't think any old trainer can awaken that in you, is that right?"

Froakie croaked in a way Ash could only perceive as him affirming his words. Sensing he was making some ground, Ash continued.

"I want to be strong too, but I know I can't do it alone. Provide me your strength, and I can prove to you just how together, we'll be unstoppable. Just let me show you what I can do."

After everyone else had their shot at getting a Pokémon, as well as taking time to meet and greet each other, Cynthia called everyone back to the battle ring. With the class now all in one group, the lesson continued.

"We will now move on to the practical exhibition match. We will pick two of you based on the Pokémon you received and you will do battle." Cynthia explained, looking at each class member, though her eyes lingered on Ash for a moment. "Remember, this won't be scored, so don't feel pressured. Our first duelists will be...Ash and Serena!"

The whole glass gasped in awe, for the social circles Ash and Serena had spread the word fast on their bet. With both of them taking a side of the ring each, Cynthia served as proctor, readying a whistle. At her shrill blow, the match started.

"Froakie, use Water Pulse!" Ash commanded his Pokémon.

"Water Pulse! That's a pretty advanced move for a starting Pokémon to use!" Clemont noted for, the sidelines.

And yet despite that, Froakie did execute the move flawlessly, forming an orb of condensed water in his hands. Throwing the sphere, it began barreling toward Fennekin at a rather fast pace.

"Dodge, then get in close!" Serena commanded, her Fire type jumping to the side before using its natural agility to flank Froakie.

With the water type caught off guard by the sudden advance, Serena followed up.

"Now, Scratch!"

With its rather sharp claws, Fennekin struck Froakie's shoulder, getting a decent blow on the Pokémon.

"Don't let up! Hit it again!"

As the Fire type went in for another hit, Ash smirked, noting from the first scratch a plan to counterattack.

"Use your frubbles, Froakie!" He commanded.

"Fro!" Froakie obeyed, taking a chucked of foaming bubbles from its backside, throwing it as Fennekin's paws.

Suddenly, the bubbles began acting as an adhesive, holding the Fire Fox down to the ground.

"What?!" Serena gasped.

"Those are Frubbles, a rather sticky substance that you see coming off my Pokemon's back." Ash explained, his knowledge on Froakie's biology surprising even Cynthia. "Quite a useful trapping tool, wouldn't you say? Now Froakie, use Water Pulse point blank!"

Froakie then charged its attack, its target helpless and immobilized.

"Use Ember!" Serena said desperately, trying to fight until the very end.

But it was no use, for by the time Fennekin mustered the embers it needed, Froakie already slammed the Water Pulse in its face, knocking it out. With a clear winner decided, the guys of the classroom cheered while the girls comforted Serena for giving a good try.

"Looks like I lose!" Serena sighed, though everyone knew that her bet made her a winner in another way.

However, Serena had much more in mind for Ash than a mere date. After time passed by, and class ended, everyone started making their way back to their dorms. All except for Serena. By the time curfew hit and everyone else went to sleep, Serena made a discreet dash across the school grounds, making sure the patrolling security staff did not see her out.

Finally making her way to her Master's door, she knocked quietly, with the door immediately being answered. With not but a word, Ash grabbed Serena by the waist, dragging her inside his abode. Shutting the door behind him, Ash exhaled.

"You weren't spotted?"

"Oh, baby, after what I did for you today, I think I'm more than able to be discreet." Serena mewed seductively.

"That whole bet thing was an interesting idea." Ash remarked, impressed by her quick thinking. "Even I was surprised by your little trick."

"When a girl's living a secret double life as a sex slave to such a stud of a man, I gotta do my best to please him." Serena hummed with a wink before doing a little twirl to show off her clothes. "How do I look, baby?"

Taking a closer look at her, Ash noticed just how fetching she looked. Donning a pair of tight, black leggings, Ash could almost see her skin underneath, her pussy pressed up against the fabric proving she wore no panties at all. Her top was an even more tight yellow yoga tank top, her erect nipples poking out inside the cloth.

"I'm liking the clothes, doll!" Ash hummed before bringing her in, cupping her ass cheeks as he planted a kiss on her puffed out lips. "But I'd bet you'd look better without them!"

"Oh just you wait, baby! I'm about to show you just how great I am!" She replied, playfully pushing him onto the couch.

As the two began making out, rubbing their hands up and down each other's bodies, the mood continued to build and build. Right as Serena straddled her owner, ready to remove her top, a quick knock on the door could be heard. Serena's heart skipped a beat, frozen in place on top of Ash. Her face full of panic, sweat starting to form near instantly, she spoke under hushed voice to an unconcerned Ash.

"Shit! We're in trouble! I gotta hide!" She gasped getting off Ash, only to see him heading to the door. "Wait! What are you-?!"

Opening the door to let his second guest in, Serena gasped to see Cynthia had come as well.

"Ms. Cynthia?! What are you doing here?!" The honey blonde asked the more mature woman.

"She's my sex slave as well, doll." Ash explained. "In fact, I made her mine before you came along. Don't worry though, it was only by an hour. I still haven't 'broken her in'."

"Ash, when you told me after class that we'd be throwing a party, I most certainly didn't expect this kind." Cynthia remarked, hardly upset, but yet feeling she needed some explanation.

"Well, you two are my sex slaves. What better way to use you for the first time then at the same time?" Ash smirked, bringing Cynthia to sit down on the couch besides Serena.

"While I certainly don't mind having fun with another girl, I do hope she was careful in coming here." Serena remarked. "Considering her 'position', she could be in even greater trouble than I would be if she was seen with you, or students in general."

"Yes, I know that." Cynthia replied. "I made absolutely sure no one saw me leave the teacher's living quarters. Nobody knows I'm here.

"If it helps any, it doesn't matter how Cynthia's older than us. I'm in control, so I'm making you do this, isn't that right, Cynthia?" Ash asked, letting his slave have some peace of mind when considering the rather taboo relationship they would soon share together.

"Don't worry about me, Ash." Cynthia responded. "I always found you rather attractive. You making me your slave has given me the confidence be true to myself and pass that boundary. But, yes, you are in control. And I couldn't be happier with that!"

"Glad you see it my way, girl!" Ash smiled. "Now, let's get this party started! Did you bring the stuff?"

"You bet I brought it, baby!" Cynthia smiled back, pulling out some beer she had in a shopping bag she brought with her.

"Alcohol, huh? Should we be drinking this?" Serena asked, grabbing a bottle anyways.

"Hey, if we're about to fuck our sexy ass teacher, we clearly can handle some beer." Ash replied. "But don't go too overboard, ladies. I still need your wits about you so you can head to your dorms."

"Yes, Master!" The two slaves obeyed as they popped the caps on their bottles.

As the trio started drinking, they began making small talk. Ash and Serena told Cynthia of when the duo first met as kids back in Kanto, before Ash found he had to move to Kalos. Cynthia elaborated on why she found Ash attractive, yet felt compelled to keep it under wraps due to such things being problematic. Continuing past that, Cynthia began to congratulate the duo on their entrance into the classes.

"You two really are very good trainers." She spoke up. "Im so glad you made it past the entrance exam! In fact, I think I need to reward both of you for being such good students..!"

"Mmm, I think I know just what kinda of treat we can get from you..!" Serena snickered, pounding down the rest of her beer before getting up close to Cynthia, pinning her down on couch. "What do you say, Cynthia? Wanna fool around a little so our Master can get ready to claim us?"

"You took the words right out of my mouth, baby!" Cynthia joked, letting Serena come in for a kiss.

Dropping their empty bottles on the floor, the two buzzed babes began making out on the couch, their hands playing with each other's hair before going down lower. As their tongues fought for dominance, their fingers found themselves on their tits. Feeling Cynthia's massive E cup sized tits beneath her office attire, Serena was in equal parts aroused, amazed, and jealous.

"You've got such big boobies, Ms. Cynthia!" She gasped, her hands juggling the bulbous tits as her mouth continued to smash against her teacher's. "I'm so jealous..!"

"You're not bad for a girl your age, darling!" Cynthia admitted, feeling Serena's own d cup sized breasts through her yoga tank top. "I'm sure you'll get even bigger."

"Speaking of big..."Serena spoke, her words trailing off as she looked to her right. "Holy fuck!"

Cynthia, turning to see what her playmate spoke of went completely jaw slack. Ash, who was watching the two babes make out for his amusement, was completely erect. His mast at full seen clear as day in his cargo pants, Cynthia could tell easily he was at least 8 inches in length. Seeing such a splendid cock that would surely be used inside her, Cynthia licked her lips then swallowed, her anticipation evidently palpable. Seeing how thirsty Cynthia looked, Serena came up with an idea.

"Why don't we let our Master get in on the action?" She asked, getting up to take Ash by the hand. "Come on! Sit down and enjoy yourself, Ash! We know we will!"

Making her Master sit on the couch, Serena and Cynthia got on their knees, their hands frisking Ash's pants, desperate to take them off. Removing his clothes, leaving only his erect penis, the two ladies looked at it, then to each other. The two then began taking turns sucking him off, with one girl inserting the entire phallus into her mouth while the other played with his ball sack, gently licking it.

"Oh fuck!" Ash grunted, grabbing both girl's by their hair gently.

Realizing just how aroused their Master was drove his slaves wild. Pausing for a minute, the two women stripped themselves of their own clothing, leaving them crumpled on the floor. Changing Ash's position on the couch, ensuring he could lay down, Cynthia decided to mount Ash's face, letting him grab her by the thighs as he proceeded to eat out her pussy.

"Wow, you're really good at this, Ash!" Cynthia moaned, gasping each time his tongue touched her clit walls. "Is this really your first time?"

"Mmm!" Ash replied, confirming her assumption as her thick, sexy thighs kept his head in a vice.

It wasn't much longer after that till Serena mounted Ash's cock, riding him cowgirl style. As the two slaves rode their Master, the two girls decided to get frisky with each other, with Serena putting her mouth around Cynthia's tit as the older woman began running circles around Serena's own nipples with her fingers.

"My my, I have such seductive students..!" She moaned, the blonde teacher's senses kicked into overload as the two teenagers assaulted her from both sides.

Sensing Ash wanted more, the two girls removed themselves from him. His cock still hungering for more, Ash grabbed Cynthia by her thighs, picking her up with his impressive strength to put her in a standing Nelson position. With his cock slamming into her pussy while Cynthia herself was suspended by Ash's brawn, Cynthia could only belt out excited moans.

"It's a good thing these walls of ours are soundproofed." Ash said, toying with his teacher. "A crazy slut like you screaming for his Master is something we'll be doing a lot in here!"

"She's so fucking horny!" Serena gasped, noticing her teacher's pussy juice squirting out from the gap between her Master's cock and her pussy.

Wasting not a single drop, Serena got on her knees, lapping up the teacher's orgasm as it trailed down her legs as well as Ash's.

"Oh my God! Fuck me harder, daddy!" Cynthia could only scream, her mind and body numb from the immense pleasure she received, helplessly fucked in her Master's hold.

Realizing his teacher hit her limit, Ash set Cynthia down on the ground face up, ensuring her orgasm continued upon witnessing Serena get fucked silly. Setting his sex pet in a doggy style position on top of the lewd teacher, Ash held tight to Serena's waist, pounding away at her virgin cunt as the older vixen Cynthia made out with her teenage student.

"This is amazing!" Serena gasped. "We have got to do this all the time, Ms. Cynthia!"

"Mmm, you two are so hot!" She replied, her arms wrapped around Serena's torso as Ash continued fucking the honey blonde's moist clit.

"Mmm, I'm coming!" Serena gasped.

"Don't worry, baby! You're gonna feel amazing!" Cynthia replied softly, ensuring her virgin sex partner relaxed and enjoyed the experience.

Realizing his limit was hit, Ash had to act quickly. Ensuring that the risk of his slaves getting pregnant didn't happen, Ash removed Serena from his beating cock, turning her face up and beside Cynthia. As soon as he did this, his penis erupted with sperm, the white substance shooting out onto his two pets' stomachs.

As soon as his climax settled down, Ash sat on the floor across from his two mates, breathing heavily.

"My first time..." he began to say. "That was my first time... and with my teacher and crush, no less..!"

"That was amazing, Ash!" Serena could only gasp, letting Cynthia lick her body clean of the sperm.

"I'm so glad I finally got to do that!" Cynthia gasped, letting Serena take her turn swallowing the sticky cum off her body. "That was so exciting! But we have to be careful now, my sexy students! We've crossed a line we can't come back from! We will need to keep our dirty little secret safe, or else people will judge us."

"Your absolutely right, my pet." Ash agreed. "Don't fret. I've got a plan for everything!"

"I knew I could count on you!" Cynthia smiled, her favorite student always finding ways to satisfy her. "We can also help with problems as well. It's what good girlfriends do, after all!"

"Just what I want to hear!" Ash smiled, making his way to the shower. "Let's get cleaned up and get you home, ladies! We can't have anyone finding out about this!"

"Yes!" The two girls agreed, following their owner to his shower.

After cleaning up at the same time, sharing one last three way kiss between each other, setting in stone how committed the three were to breaking the illicit taboo that barred teacher and student from loving each other, Ash looked out the window, checking for security guards. After seeing it was all clear, Ash sent his girls on their way, giving each a spank on the ass as the walked out the door.

After closing the door, Ash looked to the mess the three had made. Spilled droplets of beer, speckles of cum stains in the carpets, and sweaty ass prints on the couch. Realizing he would need to clean it up later, Ash went to him bedroom, his dick sore from such a thrilling experience. Before going to bed, he looked at his hypnotic device, wondering who he could make his next sex puppet.

Author's note: hello again, dear readers, I'm back with a new episode to the high school hypno harem. In this chapter, Ash finally gets to fucking his lewd sex toys. As I'm sure you all know, this is a high school fanfic, making Ash and his peers teenagers. With Cynthia being an older character, you could see how this would cause some problems regarding age.

To navigate this little problem, I came to the conclusion it does no harm, since Ash holds all the agency in their relationship. If any of you have problems with such relations, even if it's fictional, I suggest you stop reading, because Ash is gonna be banging a lot more teachers than just Cynthia. If you are upset by this kind of thing, then I can only say this: you knew what you signed up for in a high school fanfic when the first person Ash made his sex slave was his hot teacher.

I'm sure most of us had that one hot teacher we wanted to bang anyways, so if anything, this is cashing in on such fantasies. Little rant aside from the author's perspective, I hope you all enjoyed the chapter, and I hope you stay tuned, for I will be making the next chapter soon! Enjoy reading!