13th October 2012


Warning; contains much weirdness including crossdressing and humiliation. This is an Ash/Elesa pairing.

'This' means someone is thinking.

Italics alone means the name of something or someone, i.e. pokedex, hover bike.

Horizontal ruler (line across the page) means a page break or timeskip, may be a few minutes, may be a few hours...

-X- means a scene or viewpoint change, i.e. We start off in a Pokemon Centre then go to a Pokemon Gym, or we see Ash watching something, then we go to Elesa in the same room watching the same thing.

Disclaimer; I do not own Pokemon or any of the characters or ideas involved. This is non profit-I am making no money from this.


Flashes from a hundred cameras illuminated the dimly lit room. Screams of a hundred people shook the building as the star of the show made her appearance; Elesa, the electric Pokemon specialist, leader of the Nimbasa Gym, world renowned fashion model (some would say fashion Goddess) stepped onto the catwalk, a dazzling vision of style, class and cool, a tall, beautiful, radiant young woman who had the room under her control with a smile.


For a split second Elesa was frozen in disbelief at the sound. 'Who dares to yawn at me?! I'll dim their lights- permanently!' The second passed and she continued her runway routine, her ice blue eyes searching the room for the fool who dared to yawn at the peerless Shining Beauty. Her eyes fell on a teenaged male; black hair, brown eyes, tan skin wearing a red, white and blue baseball cap, a blue and white shirt, grey fingerless gloves and grey baggy trousers.


Ash Ketchum was bored, maybe even depressed. He was at this fashion show for the same reason he did anything these days- he was just going through the motions- he didn't know what else to do.

'It's just not the same anymore...' This rut Ash had fallen into recently wasn't just because he had left his oldest friend Pikachu back at Professor Oak's lab to mate with a cute FemPikachu Gary's grandfather had found injured in the nearby forest. It was like his quest had lost its spirit, its wonder and adventure he had felt for the first few years travelling the world battling to prove he was the best.

'Go to gym's, win at straight fights at Gyms, go to stadium of 'Insert name here' league, win first few rounds then lose, usually to a guy I had recently befriended...' It was a pattern of falling at the last hurdle that was clearly wearing on the recently turned 18 trainer and now caused him to consider taking a break from battling.

'Thing is, I have no idea what to do with myself without Pokemon...'


As she carried on dazzling the hundreds of people in attendance, Elesa looked on the surface to be as much the shining beauty as ever- the sharp, complex and often ruthless mind behind the glamour however had burned the face of that philistine teenager into her memory and intended at some point, at some time to exact a terrible revenge...

Only an hour later Elesa was face to face with the object of her previous vengeance fantasy.

The fool had identified himself as Ash Ketchum and demanded a battle with her. He didn't seem to have his heart in it though- she could always tell when people were faking emotions around her.

'Some badly dressed, badly groomed, badly colour coordinated punk showing up at my Gym, being in my presence and not wanting to be there? Insulting. Unforgiveable in fact.'

Her eyes were as cold as ice as Elesa looked down at him, she was taller than him, five foot, nine inches to his five, seven. With the high heels she wore, she towered over him at well over six feet. The gold and black coloured tailored pantsuit she currently wore added to the image of power she generated.


Ash was surprised, the first genuine emotion she had seen in him other than boredom at the fashion show earlier.

"Why?" He blurted out.

Elesa turned her head away and stuck her nose up, something she did to signify to insignificance of whoever was in her presence.

"You don't know the stresses of being a model as well as a Gym leader. As a Gym leader you need to present professionalism and power, as a model you need to project beauty, grace and sophistication. Confidence of course is needed in both roles." When she finished she still wasn't looking at him, but was preening as though there were still cameras present.

Ash snorted. "You dress up in weird clothes and strut around. How hard can that be, girls do that anyway." A phantom pain in his head made him glad Misty and her various implements of pain wasn't around to hear him say that.

Elesa turned to him in cold fury, a nasty idea came to her- more constructive and amusing than her original thought of dismembering him; "Fine. I know I can battle as good as you, but can you put on a show as good as me? If you want a battle, take part in a show."

Ash was stunned. "What! I'm not putting on frilly clothing and swaggering around like a peacock!"

"Because you can't do it, boys are so insecure, afraid of being labelled girly, a loser or gay by total strangers that they just go with the flow... copying what everyone else does... afraid of doing their own thing..."

"I'm not afraid of anything! And I always do my own thing!" Ash shouted, finally angry.

'Boys are so easy...' Amongst her many talents Elesa was also a master manipulator and shrewd negotiator, the trick was to begin with an outrageous offer (not so outrageous that the other guy walks away) and then change so it appears that you're compromising.

After a bit of shouting, weaselling and whining from Ash, some insults and doubts about his manhood and sexuality from Elesa and the Pallet town trainer had agreed to a "Private show" with Elesa as the soul viewer- although only if Ash lost his battle to the slender young woman first- a compromise the Nimbasa Gym leader had no problem with since she had full confidence in her ability to dominate her opponent.

"And you give your word as a man that you'll follow through?" She asked, knowing that was the clincher.


Ash Ketchum stepped into the Nimbasa battle arena. He looked around in bewilderment- the bizarre looking shapes and lights on the walls reminded him of 80's disco.

His opponent appeared, illuminated by not one, or two but three spotlights. Tall and striking as ever, she wore a strange outfit consisting of a sleeveless shirt (or possibly a short dress) of yellow and black with stripes showing bare flesh beneath at strategic locations, a black choker around her neck and skintight black pants that complemented her long legs. Again she wore high heels. On her head she wore decorations shaped and positioned like earmuffs or headphones, trailing from them were tassels- or cables- Ash couldn't tell.

She assumed a confident pose that had that weird sparkle some girls got. The crowd went wild and Ash watched mildly annoyed as she ignored him and played to the fans. Their screaming was deafening and their enthusiasm angered him for some reason.

"Are you ready? You're looking quite dull." Ash blinked and realized that the Gym leader was talking to him.

"Yeah, I'm ready and who's dull?" Ash shouted back.

A few minutes later and it was obvious the battle was not going well for Ash; his strategy was good, his Pokemon were strong, but his heart wasn't in it- or as Elesa had observed; "You are dim." "So not dazzling." "Ohhh, the gloom is draining my radiance..."

"Stop it with the light jokes! It's not funny!" Ash shouted after his Palpitoad was taken out by her "radiant" Emolga.

"Oh, you have some spark after all, but can you get it up to a blinding shine?"

"Seriously, that's not funny..." Ash groused as the crowd went wild at Elesa's trademark brightness based banter.

Ash was unable to mount a comeback with his Snivy swiftly taken out with superior speed and an Aerial Ace and his Tranquil falling after a lengthy battle of quickness and stamina.

While Elesa preened and posed in victory to her adoring supporters, her attention was actually on Ash as she pounded his Pokemon and punished him with her puns. She was interested to see that while the hurt caused to his Pokemon bothered him, losing the battle itself, did not.

'I guess I'll have to impress on him the consequences of not giving it your all and losing to me...'


Elesa greeted Ash with a warm, even cute smile. Like the day before she was dressed in her battle outfit. She then led him to the same establishment that had held the fashion show the previous day. The crowds were gone and Elesa assured Ash no one would bother them and that there were no security cameras watching them.

She led him to the dressing room to put on his outfit. Ash trembled, his heart pounding madly. 'What the hell am I thinking letting this crazy bitch make me her dress up doll... then again I've crossdressed three times, one time in a freaking cafe...'

"Feeling nervous?" She asked.

"No." He replied too quickly.

"You shouldn't be, you have so much amateur experience in modelling;" She pulled out a palm sized device with a screen, it showed a clip show (with a spunky techno soundtrack) consisting of images Ash in various guises in various Pokemon coordinator contests, and several in female attire, Elesa paused on an image of Ash wearing a maid's outfit. Ash blushed in embarrassment as his blood froze. "How did you get that?" He spluttered.

"Trade secret. Don't be embarrassed. You do pull off women's clothing quite well..." Ash got a very bad feeling as he saw a sinister look in Elesa's blue eyes.

They entered the dressing room and Ash stopped dead as he saw the clothing he was to put on. He remained frozen in horror for several moments before spluttering out. "No... no way! There is no way I'm putting... that on!"

"I looked you up... I think your problem is that failure doesn't bother you anymore... given that battling me, or being in my presence-" She preened again, which was really annoying. "-is a reward in itself It's not unreasonable to expect the harshest punishment for losing is it?" She smiled wider than usual looking downright evil.


"Are you ready yet?" Elesa yelled from her seat in front of the deserted Aurora Centre's catwalk, she had a bottle of her favourite White Forest wine on a table next to her.

"I'M NOT COMING OUT IN THIS!" Yelled a voice from behind the curtain at the other side of the catwalk.


Elesa watched the curtain in anticipation confident she had him.

The curtain opened revealing... Ash Ketchum wearing nothing but women's lingerie; a patterned silk bra, negligee, matching panties, a garter belt connecting to stockings and high heels- all white in floral pattern.

Elesa took a discerning look from toe to head. Ash wasn't very tall, but he was quite athletic in build, the silky undergarments gave no cover for his body from her eyes he had his hands covering his crotch almost childishly. His face was as red as a cherry, and she could see his body trembling through fear, but his face had a look of determination on it- of fire that wasn't present even when they argued earlier.

She gestured for him to walk the catwalk towards her. He obeyed and staggered forward awkwardly in the high heels. He stopped in front of her, scowling menacingly. She thought it was cute and struggled to suppress a giggle.

He fidgeted under her gaze. She made a finger gesture that confused Ash.

"Turn around." She supplied. Ash's eyes widened, but he obeyed, turning as his heart pounded madly, his stomach lurched and his sweating became very noticeable. Staring ahead at a wall he was unaware of Elesa studying his toned ass in appreciation.

"Hmm... try the next one." Ash turned to complain- to rage, but stopped himself and nodded in defeat. 'The Unova League... becoming a Pokemon Master... that's why I'm doing this...' He stomped off angrily nearly falling over in the now painful heels. Elesa barely contained laughter as she watched him go revelling in the power she had over him.


The curtain opened a second time revealing Ash in similar humiliating attire, except even more skimpy, his briefs were now a thong that felt weird- not quite uncomfortable between his ass cheeks- his cock and balls were not fully covered by the garment which made Ash glad the perverse bitch had given him an almost skirt sized garter belt which hid his private parts from view. His outfit was a (in very different circumstances) relaxing ocean blue colour.

He saw his tormentor sipping wine from a glass in full aristocratic style. He stumbled towards Elesa angrily hoping this humiliating getup would be the final disgrace.

It wasn't; over the next hour Ash was ogled and judged as he walked back and forth in bustiers, see-through blouses, corsets, thongs, bikinis and other articles of female clothing he didn't know the names of and was too humiliated to ask.

Elesa was actually astonished Ash didn't break his word and run off. Certainly an ordinary male wouldn't do this for their partner- let alone a complete stranger.

Ash's sadistic judge stood up. "Not bad. No grace, no style. But I respect your follow through and you will be rewarded." She beamed at him and Ash felt conflicted feelings of joy and anger.

"Can I get out of these... things now?" He asked. He currently wore an underwire Basque (not that Ash knew what that was); an almost transparent corset (the section to cover breasts looked the same as a normal bra) connected to long stockings via a cotton straps, the briefs were impractical underwear- a thong that felt downright uncomfortable and humiliating as it bulged at the front with Ash's rather significant manhood and gave him a minor wedgie at the back. Like his first emasculating garb it was a spotless white colour.

Elesa smiled at him. "Not quite yet." Before Ash could respond she had grabbed his hand and was leading him off the catwalk to a nearby chair.

She shoved him down in it. Ash blinked in bewilderment as Elesa began moving oddly in front of him. It took him several seconds to realize she was dancing. Ash adjusted uncomfortably in his seat watching wide eyed as Elesa swayed gracefully, her slender body hypnotic.

"W-what are you going?" Ash asked, his voice breaking with fright.

"You were... dazzling... I can't allow myself to be upstaged..."

Ash mouth opened wider, the teen then looked away in embarrassment as Elesa pulled up her dress/shirt combo showing a teasing hint of flat belly beneath, she carried on regardless swaying her hips in a hypnotic rhythm. Elesa tossed her shirt at Ash and he turned back astonished to see the slender woman's cleavage- small but perfectly shaped and barely contained by a black cotton bra. Ash felt a throbbing in his groin- half Elesa, half manhood stretching in the uncomfortably tight women's thong he was wearing. His hands covered it as he watched the shining beauty helplessly.

Ash gawked as he watched Elesa go from slow, hypnotic movements to performing a series of astonishingly flexible movements. He gulped as the blond smirked evilly at him while agonizingly slowly pulling her skin tight black pants down her drool inducing long legs, bending over and nearly touching the floor with her head as the garment was removed. Now clad only in her underwear, Elesa dropped to her knees and crawled over to the nearly hyperventilating Ash. He nearly jumped in shock as she put her hands on his legs. He felt her touch and warmth through the silky fishnets he currently wore as she rubbed his legs up and down in velvet smooth strokes. With his attention focused on her cleavage, he was caught off guard when Elesa lunged forward, putting her arms on the chair on either side of his head and began moving her body only centimetres away from him.

Ash stared into the distance convinced if he looked at her he'd lose control, the pulsing feeling in his lower regions were painful now. He felt her breath on his shoulder. Finally after an eternity of teasing she straddled him, her slender thighs resting on the male hands trying vainly to conceal Ash's huge erection. She watched in satisfaction as the red faced Ash stared stupidly into the cleavage practically in his nose.

Sitting atop Ash, Elesa put her hands gently on his face and leaned over and kissed him, Ash eagerly leaned into it.


Thirty minutes later they both lay exhausted on the runway.

For the past half hour Ash had experienced things beyond his young imagination.

Elesa had touched him in ways he had never imagined; she had already bent him to her will, humiliating him, and from there she entranced him, playing his body like an instrument as she took him sexually on the chair, then the runway.

She guided him, controlled him, owned him as she took his body and used it to pleasure herself and Ash loved it all. He was helpless, a moth staring into a flame.

Elesa lay atop Ash completely naked, the male beneath her was still dressed in lingerie- now stained with sweat and sexual juices- the domineering blond had refused to let him remove it. She held her face in her hands. Her elbows were propping her up and pressing into Ash's chest.

She asked him something as she looked down on him.

"Feel the spark and tingle? Different from at the match huh?"

"I don't suppose you'd be interested in a rematch?" She asked him.

He stared at her confused. Then it hit him.

"And... what would happen if I lost?" He asked eagerly.

"I'm sure I could think of something... you know I once had an offer to model for a BDSM catalogue..."



This started out as a joke on how many times Ash has crossdressed in canon.

My original idea for an Ash/Elesa fic was for Elesa to defeat Ash in a battle, render him unconscious, tie him to a bed them torment him with BDSM using bits of fashion; i.e. tying him down with scarves or leather clothing, using a thong as a makeshift flogger, etc. I couldn't make the story make any sense so I dropped in favour of a story that was more about role reversal and humiliation than straight forward BDSM.

This is an edited version of the story. The unedited version is on a link on my Authors Page.