Salem in New Donk City

Salem finally arrived at his newest score: New Donk City. Sure, the rumors absolutely described this place as crawling with pretty powerful Midara who seemed to be in cahoots, but they also told of a seemingly endless bounty of unique golden coins, as well as other artifacts of unknowable value. The perfect target for a Thief like Salem. He'd need only slip in, find the loot, and slip out. And slipping in would be the easy part, because it looked like the front gates just let anyone through!

A big city, the perfect environment for someone like him...first things first, just had to slip in without drawing any eyes, no need to try and be stealthy when walking through something public, he'd just...well, move to step through the gates!

And, stepping through the gates was easy-peasy. There was a decent crowd just beyond them, a nice open square, a bunch of very strange plants and architecture like blocks and pipes, and a bunch of doors that led into what looked more like a complex that a city's streets.

"...hm." okay...the place was nice but it also seemed a little...weird...ah well! He'd start looking around for someone who'd be good to pickpocket, an easy start.
[Aka, searching for either an encounter or an event]

Search (92) Crit Success

Salem barely had to scan the scene for two seconds before spotting the perfect mark. A rich-looking lady in a purple dress that was browsing a few of the snack stalls in the square. All he'd need to do was pick her pockets and he'd have some coin to get himself started.

He smirked slightly, perfect, distracted too, an easy target...slowly, he'd sneak his way over to her, and...well, do what he did best, start picking her pockets for some easy money...
[Roll to pickpocket?]

Pickpocket (87) Crit Fail

Salem tried to reach for her pockets... but at the very last moment, she backed up and shifted her hips, leaving Salem to instead get a good handle on her ass through her dress. "Uwaa?! What do you think you're doing?!" The rich lady shouted as she pulled herself away from Salem and glared at him.

"!" Well, that's not good...but, he can make this work.
"H-heh, sorry about that...hands have a mind of their own sometimes, especially when something so good is so close..." He smirked faintly, hoping to defuse the situation with a little bit of flirting...
(Hopefully this roll goes a bit better )

Flirt (56) Success

The woman blushed lightly and stubbornly turned her head away. "Absolutely shameless. If you're so incorrigible, you should find an establishment to suit you before you grope a woman less forgiving than me." She scolded him.

...welp, might as well have a little fun with this... "Sorry, sorry...buuuut...you seem to be getting a little red in the face there, miss...wonder why that could be?"
[Flirting agaaaain]

Flirt (36) Success

The rich lady sputtered as Salem teased her, her face getting even more red as she faces him again. "B-because I can't believe you're wasting your time on me when there's any number of ways for a pervert like you to find a woman to take you. It's as if you'd prefer that I punished you instead."

He offered a sly, sorta charming smile as she turned to look at him, humming faintly as he leaned in just a little closer to push this a bit further. "And I think...perhaps you like the attention, just a bit...and now you have me curious...what would you do as punishment?"

Flirt (11) Crit Fail... ?

The rich lady then suddenly broke into a devious grin as she came closer and leaned her curvy body and smooth dress into Salem. "Whatever it took to satisfy a pervert like you. I'd leave you so delightfully broken, you'd wish I'd find you again and again."

...and like that...this had gotten far more interesting. A grin of his own forming as he shifted to loop an arm around her waist. "Well...maybe that's something I'd like to see you try and do~ Attention like that from someone so beautiful would only be fun~"

The noblewoman backed her ass into Salem's touch and filled his hand with her surprisingly curvy and voluptuous ass. An ass-lover like him couldn't ignore just how... soft it was. "In that case, simply follow Lady Cordella to her home, and I'll make sure a slut like you is properly punished. Ah... but you can call me mistress." She insisted, giving him one last chance to excuse himself.... or incriminate himself further.

Salem: 27 Willpower

And his enjoyment of her curves clouded...any other judgement, his body tensing for a moment as he gave her ass a firm squeeze as it backed into his grip. "...heh...very well, mistress..."

He figured...it could be a good time, plus, perhaps getting someone to like him here would be helpful...

"Right this way. You're in need of punishment, pervert~." Lady Cordella replied, shifting her hips to rub her ass into his hands, and then turning to press her booty right into his crotch. After an unsubtle taste of her assjob, she started strolling down the street, her rear perfectly highlighted by her tight dress as it waved to and from with each step.

Salem: 24 Willpower

He let out a small gasp at the feeling of her big round ass press against his crotch, shuddering faintly before starting to follow her, eyes focused on her rear as it waved around with each step from her.

The Lady had a smug grin on her lips as she marched towards her home, knowing that she'd have work to do once they arrived. In the meantime, Salem got to admire her nearly perfect ass shift and shake in her dress, none of its luscious curves left to his imagination. Especially when he'd occasionally get to glimpse her fair, supple skin through a gap in her dress.

Salem: 21 Willpower, Fascinated

Salem...well, Salem had no shame in what he was getting into, happily following behind The Lady and...admittedly enjoying every bit of this, he couldn't deny it, this whole thing was...really hot, and something he couldn't help but be into...

Before the lust-addled Salem realized it, they were in Lady Cordella's home. Her high heels clicked against her hardwood floor as her ass kept beckoning him to follow her right into her bedroom. "Ahhhh~ Good to be home~ I'd love to take a load off and read at my desk.... ahh... but, I seem to have misplaced my chair, wherever will I sit?" She asked coyly, sticking her ass out so Salem would finally get a full view of her thick booty.

Salem: 18 Willpower, Fascinated

He couldn't deny the small smirk on his face when he heard her talk, trying not to think about the forming tent in his pants.
"You're not exactly subtle are you, mistress?...I'll be your seat if you really want that...if you don't mind pulling up the dress first? More enjoyable that way, don't you think~?"

"Very well, I can do that much for a horny chair like you." Cordella replied before she shifted her dress and fully unveiled her beautiful bubble butt and gave it a wiggle side to side. Waiting for Salem to get ready to serve as her seat for the time being.

In a slightly bold move, he leaned down and placed a quick affectionate kiss on one of those big plush cheeks before shifting to get ready, waiting for this face to be made her seat...

The noblewoman backed her ass into Salem's face as he offered her a quick kiss, burying him between her cheeks before she leaned back and got herself seated. Leaving the thief's face entombed beneath her booty as she idly shifted and shook her hips back and forth on him.

Salem: 7 Willpower, Fascinated