Ash Ketchum Crossdressing One-Shots
Cynthia Chapter 21
Co-Writer GreyKing46
We do not own Pokémon. All rights and credit go to Nintendo and Game Freak
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The Pokémon League. The pinnacle of all trainers' aspirations. To rise to the top of the mountain and conquer the peak.
The battle was hard, taxing on mental strength and strategy.
The Champion of Sinnoh, Cynthia. A being as strong as a team of Legendary Pokémon with her own team. The woman who stands above all on Mt. Coronet.
Was currently sitting with her opponent. Ashley, enjoying a coffee with her.
Taking a sip of her coffee, she placed her cup onto its saucer and then onto the table. "I'm still amazed by you, Ashley. You're one fantastic trainer."
"Awe~, shucks. Thanks." Ashley blushed, rubbing the back of her head.
"Still, it has been a long time since anyone has defeated me." Cynthia answered
Ashley nodded, blushing a bit as Cynthia was seen as one of the most attractive women in the world
"You've not said a lot since the match." Cynthia added, leaning down and looking into Ashley's eyes, Cynthia's head in her hand in a sensual pose with the woman's large breasts just... Hanging there
Ashley's face was flushed and red as a Tamato berry.
"Tell me, are you seeing anyone?" Cynthia asked
"I... Yeah." She gulped
"Really? Is she cute like you?" Cynthia asked
"Y-Yes she is. Why?" Ashley responded nervously... "What's with the look in your eye?"
"I've heard MANY things about you." Cynthia answered. "Sabrina, Professor Ivy, Anabel." She listed off some of the names of people that Ashley had been with. "You've had QUITE the journey."
She reached up, grasping her chin softly
"Hmm!" Ashley blushed. "I-well, I-" Mumbling before being kissed by Cynthia.
The blonde held her gently, kissing her lovingly
'Oh my, Arceus!' Ashley thought as she was being kissed by Sinnoh's champion.
"Ah~, Ashley. Can you bring your girlfriend here?" Cynthia asked
"Okay." She squeaked
"I'll be waiting at the Cressilia Hotel." Cynthia whispered and walked off
Ashley panted as she felt her heart thump in her ears...was this REALLY happening?
*Time Skip*
Ashley whimpered happily, dragging Dawn behind her
"So, run this by me again. We're going to one of the most expensive hotels in the region...as GUESTS?!" Dawn asked in shock.
"Yeah." Ashley nodded
"Oh boy." Dawn blushed as she used her hand like a fan.
The two entered the Cresselia Hotel and were instructed to go to the 'Champion's Lounge'.
Dawn gulped and followed
"Okay, here we are." Ashley whispered as she and Dawn reached the top.
CREAK.
"Enter." Cynthia's voice ordered gently and playfully.
"Cynthia?" Dawn blinked as she was dragged in
"Yeah." Ashley nodded as the two saw the Champion of Sinnoh.
"Oh. My god." Dawn and Ashley gasped as they saw a near-nude Cynthia. Who was wearing black lingerie.
"A-Ashley. What's going on?" Dawn blushed as she saw her.
"Dawn. You know how I have had multiple-?" Ashley asked
"I know." Dawn nodded, flitting between Cynthia and Ashley.
"Well... She wants us."
"Y-You do?" Dawn gulped, feeling small in the body department compared to Cynthia's DD-Cup breasts
"I do. And don't worry, you're quite beautiful." Cynthia answered reassuringly seeing how shy she was getting.
She kissed the bluenette carefully, her lips the epitome of gentle and soft
"Hmm~?" Dawn's eyes moaned as she felt Cynthia's lips.
"Hot." Ashley whispered, before feeling Cynthia's hand stroking her crotch area.
She let the older woman lead, she and Dawn were hers tonight
"Ah~, now...Who first?" Cynthia asked lovingly
"I think, Dawn first. Treat her well." Ashley asked with a wink
"M-Me?" Dawn blushed.
"I will." Cynthia nodded and kissed her, slowly guiding and stripping Dawn to the bed.
Dawn was soon naked, lying on the bed
"Such a beautiful girl." Cynthia smiled kissing and teasing Dawn's body.
"A-Ah~. Ash. Ley." Dawn panted, seeing her girlfriend stand there and biting her lower lip.
"Eyes on me, Dawn." Cynthia ordered gently and kissed her on the lips.
'She's so adorable.' Ashley thought, rubbing her cocklet as she saw the two kiss.
"Ashley, I'm feeling a little lonely." Cynthia spoke, wiggling her hips.
"H.. huh?" Ashley blinked, looking at the sexy black thing clad ass
"Do you want to taste my pussy?" Cynthia teased her.
Ashley nodded quickly, licking her lips at the thought
"Then come here." Cynthia pulled her lingerie down and showed her pussy
Ashley nodded, kneeling behind her. She grabbed the perfect ass and dove in, her tongue running along the soaked slit
"Hmm~, that's it. Tongue my slit." Cynthia smiled as she ate out Dawn.
"Cynthia!" Dawn moaned
'Cum, cum for me, Dawn.' Cynthia thought as she smiled internally. 'Squirt you little girl.'
"A-AH~!" Dawn moaned and squirted into Cynthia's mouth
She fell to the bed, shaking
Cynthia smiled, licking her lips as she held Ashley close, getting the fem-boy to make her cum. "I know you can do it, come on!" She urged
Ashley hummed gently, doing her best and then thought...to play with Cynthia's asshole.
She smiled cheekily, using her hand to begin to rub that hole
"AH~! Oh, yes! Cheeky girl. Yes, tease me!" Cynthia moaned "Fuck! Gonna cum!"
"HMM~!" Ashley smiled as she was now hard for her...and pulled back, wanting to fuck Cynthia, this woman was too much.
"Why'd you stop?" Cynthia asked...before she felt Ashley rub something against her slit. "What a naughty girl."
"I-I want to try." Ashley begged. "Please?"
"Go ahead. Nothing but my fingers and your tongue has been in there since my baby was born." Cynthia smirked
"Y-You're a mum?" Ashley asked in awe, not realising she was going to fuck a MILF. Prodding her cocklet into her pussy
"Yes, I'm a hot, horny MILF...and I want some fem-boy cock inside me." Cynthia teased, slowly prodding her pussy on Ashley's cocklet.
'F-Fem-boy?' Dawn thought tiredly as she heard her.
Ashley drooled with ecstasy, before shoving her cocklet within her. "HMM~! Eager aren't you?" Cynthia panted as she felt Ashley's member thrust within her.
"Yes!" She moaned lustfully
Ashley continued to fuck Cynthia, Dawn looking up at Cynthia's swinging breasts. And, on instinct, grabbed them and began to suckle on her teats like a horny baby.
Cynthia gasped and moaned
Ashley looked at Dawn, lusting after her as she was fucking Cynthia, feeling her warm wet slit hug her cocklet, wanting her cum inside her. "C-Cynthia. So good!"
"Good girl." Cynthia moaned
Dawn continued to suckle on Cynthia's breasts, teasing and rubbing the nipple; while also teasing her own clit, feeling hot and moist.
She masturbated to this whole event, finding it hot
"I-I'm cumming. I want to cum!" Ashley moaned, going to climax inside Cynthia.
"Do it. Fill my MILF pussy with your cum." Cynthia ordered lustfully
Ashley panted and squirted inside Cynthia.
Ashley moaned, her eyes fluttering closed
Cynthia hummed happily, feeling Ashley's cum inside her as the Fem-boy fell out of her pussy and landed softly on the bed. "Such a good girl. And good girls need rewards."
"Re... Ward?"
"Yes. Dawn, give her some love. I need to get something." Cynthia nodded
"Yes~!" Dawn smiled, going to Ashley and kissed her girlfriend, stroking her body against hers.
Ashley moaned, her tongue battling Dawn's
Cynthia smiled as she saw the two as she got herself a dildo from a bag she had prepared. She wanted to give the Sinnoh League victor a good present.
She licked it, getting it wet as she watched the show
Breaking the kiss, Dawn lifted up Ashley's cocklet and wanted to be one with her girlfriend.
"Here we go." She said shyly
"Dawn." Ashley looked up at the girl, slowly entering her with as much energy as she could muster, but due to her training with her fiancé and others, she could keep it up for hours.
Not that she normally used this, she preferred taking than receiving
"So cute. Like a vanilla couple." Cynthia smiled
"Hmm!" Dawn blushed as she WAS a virgin. Saving herself for Ashley.
"Oh~, so beautiful." Cynthia smiled, walking over and using the dildo, prodded Ashley's pucker-hole before she pushed it in
Ashley's eyes widened happily, feeling the dildo inside of her; making her cocklet harden inside of Dawn and thrust happily within her.
The two moaned, holding one another close
"A-Ashley~!" Dawn kissed her lover and girlfriend, feeling her hard cocklet inside of her.
It was different than her fingers
'Cum, cum for me. Please.' Ashley thought lovingly as she held and kissed Dawn.
The two moaned, their minds going white as they came together
Cynthia continued to smile as she saw the two. She knew that this was the best thing she had done in a while.
To Be Continued
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