He smirked as she entered the bedroom, enjoying seeing her struggling to keep the buttons firmly fastened as she breathed as shallowly as she could. He did not feel guilty at taking sadistic pleasure out of her endeavours as it had been her choice entirely and there was a pricey wager riding on whether she could do it successfully or not. As she made it over to his location, with a smile she (quite literally) whispered breathlessly that she had won the bet and he had to pay up. Before he could offer her any form of reply that wasn't staring at the material defying her to stay shut, she straddled his lap and brushed her lips against his teasingly. Sadly for her, the button that strained the most sprang off and hit him in the eye. Rubbing it gingerly, he grinned again and she sighed, knowing that she'd spoken far too soon.

"Told you you'd never fit into it again, pay up!"

Muttering angrily at thinking her chest hadn't grown all that much since her days at Pokémon Tech, she took her frustration out by ripping her shirt open across the middle, thus sending all the other buttons to a similar fate. She took the rest of the uniform off but let the suspenders remain, and sighed as she put a very expensive under-bust corset on. She wished he'd just agree to wear things like this instead of her having to gamble with him on every occasion, and she could have sworn she'd win this time. She didn't realise James had deliberately bought a new shirt, identical to her proper one except for the fact it was three sizes smaller. She also wished he hadn't been so cruel with what she had to do if she lost. Sticking a coin to her forehead, she purred seductively and said:

"Have I been a good kitty, Mr Boss?"

As soon as he burst out laughing, all went to black. Her anger management classes weren't finished yet.

When he came to, he noticed a few things almost immediately. He was completely naked on the four poster bed and nursed a sizeable lump on the side of the head where she'd struck him. His hands were tied with incredible force to the corners of said bed with her suspenders. Jessie, the obvious culprit, was nowhere in sight. But most insulting of the scenario was his stomach being daubed in her lipstick that read "I LIKE LITTLE KITTENS FOR SEX TOYS" It when he craned his neck forward he read the subtext with a sardonic smile. With a big arrow pointing to his nether regions, there was an unmistakable sentence that would make him lose that part of his anatomy should anyone else read it. Beside the arrow, was a simple "THIS IS THE BOSS". She had also taken the time to draw a crude stick figure with a mass of pokéballs where the arrow pointed. Surprisingly, he mused over whether she could actually afford to buy a new lipstick or not. With a few blatantly unsuccessful attempts to free himself from his unwilling captivity, he decided that requesting help was his only available option.

"Oh MEEEEEEOOOOOWTH?"

"What do you want this time?"

"She's done it again…"

"I can't reach the handle, you're gonna have to wait until she comes back."

"Where's she gone? And can't you break in an air vent or the window or something?"

"You're on your own Jimmy; I am NOT going through all of this again just to see you helpless. I do NOT like doing it despite what you think with the amount of times you've asked me this week! And she said something about returning the stupid leather…?"

James sweat-dropped and cringed as best he could in that position. She would definitely not be happy when she came back. Maybe next time he'd just dress in drag to shut her up, it meant he usually got further with her before being knocked out. He could not wait until she passed that anger management course, maybe then their sex life would be somewhat more normal.

What seemed like days but was in fact little over half an hour later, Jessie finally returned to the stranded male. Out of curiosity, Meowth wandered in too to see what her handiwork was like this time, and grimaced when he saw the depiction of their boss who was so dear to his feline heart. He scratched through the flimsy hosiery which earned him a wallop to the back of the head by his female co-worker for ruining the items. He left sourly, muttering about how they'd have been riddled with ladders anyway with knots that tight. James tried to prop himself, which he did rather clumsily due to his arms having no power in them from a distinct lack of circulation. Jessie pulled him towards her with the remnants of the suspenders on his wrist and kissed him fervently. He mentally panicked at this, knowing somehow it wasn't going to end well for him one way or another.

"When I took it back I saw this fantastic little…"

"No."

"You don't even know what it is yet!"

"I don't need to, I'm not wearing it."

"You don't have a choice in the matter MY dear James."

"Everyone's entitled to an opinion, and since when do you call me that?!"

"Except you when it conflicts with mine! Now, sit forward so I can put it on you easily…"

James was sorely tempted to marry his psycho ex-fiancée. At least she drew the line at whips. His eyes widened in a level of horror he did not think was possible as she produced the purchased items from the bag on her lap. Why did she never willingly want to wear this stuff herself?! In her hands lay a set of lavishly decorated nipple tassels, with what appeared to be very expensive jewels studded around them. Because of his heritage, just looking at them told him they had not come cheaply, and sighed knowing this was payback for all the times he'd blown their funds on self-detonating contraptions. Giovanni's punishment had been humiliating enough in his eyes, but all it had succeeded in doing was grind down his self-esteem and made Jessie more demonic. She preferred the term creative. He blurted out that she knew the rules if she wanted him to wear it, causing her to grudgingly cease her peeling of the back adhesives.

"What do you want this time?"

James grinned a wicked grin. He knew a foolproof plan that would no doubt end his victory, whilst abiding by the rules that it had to be something she had to successfully complete for it to be a true victory. But there was no way she could EVER pull this one off, of that he was certain.

"You get to convince Meowth to dress up in shackles with a glittery tiara and call the Boss. Whilst singing 'Look at meeee.' And it must involve a manacled version of the hula somehow."

He was not prepared for her equally self-certain smile, or her sickly sweet reply.

"Oh that's fine. You know just how much he always goes on about 'wanting to please the Boss'. He'll do it for nothing."

His face fell, knowing with horror what she said was true. He needed to get to Meowth before she did, and fast. Jessie read his thoughts correctly and stuck the tassel in her hand on his…nose…before he could leave swiftly enough. He found the cat-type with great ease, but within moments the pokémon was a hissing fluffed out pincushion for all he could tell. James naturally resembled something that no living creature should ever witness, with the tassel swinging merrily to contrast the lipstick graffiti and the ragged remnants of the suspenders that were still tied tightly around his wrists. Before he could utter a word to the scarred-for-life pokémon, however, Jessie knocked him out again as she appeared silently behind him. He had no idea there was a love heart with another crude depiction, but this time of Ash, inside it tattooed in lipstick on his ass, which she was viewing admiringly. She tried not to think about how she'd applied some AFTER scrawling it on him.

Consciousness returned all too soon with a kick to his stomach. He recognised that feeling all too well now, but what frightened him most was this time he felt his hands bound together extremely tightly. He could not see it though, or breathe that well because something was over his head, and he prayed it wasn't the gimp mask she'd purchased a few months ago but he'd also refused to wear. His fears were confirmed when he heard a zip slide back and brightness—and torturous images—filled his vision. It was too late to shut his eyes; he couldn't undo the ghastly sight of Meowth's hula in front of the videophone. This, for some reason, now also included a hideous set of glittery eyelashes to coordinate accordingly with the tiara. He could not think up any logical reason for the garish shade of blue eye shadow, or what appeared to be a mirrored disco ball hanging from the dark bit of Meowth's tail. He wished he still had tears left to cry.

He decided to make a break for it while he still could, only to find his feet were also tightly bound. As he lay on his back, cursing the pain this action delivered, he noticed Jessie was looking at him particularly smugly, with leashes in her hands attached to both his wrists and ankles. He couldn't work out where the third one led too…then he felt tightness around his neck which could only be a collar of some description. She resembled the dog-type walker from hell.

He whimpered as she pulled him back to his feet and he knew instantly that he was going to die by her hands. Most likely it would probably happen in the next five minutes. All her months of plotting to get him in drag had now come to light, and with her evident love of bondage he knew it didn't add up well. Help came from an unlikely source; Giovanni bellowed out what the hell did James think he was doing. The scenario clearly hadn't bothered him (he assumed the Boss either liked Meowth's hideous hula or Jessie's dominatrix outfit too much to notice him until now), but he could now clearly see Jessie's lipstick message with the arrow. The only luck in the whole traumatic incident was his hands were strategically hiding the crude stick figure from view.

A/N:

Yeah this is random garbled crud...blame insomnia for it. I've decided to make it into a multishot to see what reaction I get for it rather than slaving over a longish piece and getting nothing back. If you want more, review. If you don't, well might not update. Which is probably a good thing for my sanity's sake!