A hands on kind of leader...

Friday October 11, 2024

Lilly watched the last mourner walk through the front door and she waved her silk clove clad hand towards them with a half smile on her face.

Henry was dead, and inside she was crying out in joy, but on the outside she had to maintain appearances.

There were still his children that would fight the will, even though they were all rich on their own terms already, just to spite her, and then there was Charles.

None of them had been happy when she’d “upgraded” from Charles to his father, but when the opportunity appeared, she’d jumped at it.

She couldn’t imagine having to put up with Charles for decades when Henry was just years away from his final night on earth. It had been easy enough to pretend to be in interested when Henry had made an advance on her, she didn’t even feel bad about betraying Charles, both father and son were terrible people.


“What do you mean I have to attend a financial management retreat?” Lilly asked with distain her her voice.

“I’m afraid that Henry made it a requirement before you would inherit his fortune.” Reginald replied, he was Henry’s long time lawyer and was the executor of his will as well.

Lilly frowned and shook her head, “That’s ridiculous Reggie. I won’t do it, I’m a grown woman and known how to handle money.” she replied.

“Well you could fight it if you want to, but if you do and lose then Henry stipulated that all of his money goes to his other heirs.”

“Shit! Is that legal?”

“Yes, I’m afraid it is.”

Lilly thought about it for a few minutes, then sighed and let her shoulders slump, “Fine, whatever, how bad can it be?”

“Oh not bad at all really, it’s just a week in the Swiss Alps. A very high end resort and spa where the retreat takes place. You don’t even have to go to the sessions if you don’t want to, they don’t track attendance other than that you are at the resort for the entire week.”

A smile crossed Lilly’s lips and she nodded in agreement.


Lilly walked into the front entranceway of Charles mansion with a smile on her lips and a bounce in her step.

The financial retreat had been so enlightening and the resort so amazing that she’d extended her stay a few more weeks and take the opportunity to completely make herself over.

She deserved it after all, she was a widow but wasn’t dead!

She walked up to Charles front door and pushed the doorbell, the chimes sounded and she clasped her hands behind her back and pushed her tits out, wiggling in place a little as she waited.

It wasn’t long before Charles opened the door and a broad smile crossed his lips.

“Hi Charles!” she said enthusiastically as she bounced a little in place.

“Well hello Lilly.” Charles replied and moved to the side a little, gesturing her to enter his home.

She blushed a little and slipped through the door, giving her ass a wiggle as she passed him.

God she’d been so dumb to ever dump him for Henry, but then again, she as just a dumb little slut so that kinda fit her MO anyway.

She let out a giggle at her own internal monologue, which was quickly followed by a little moan as Charles step up beside her and slipped his arm around her waist, his hand landing on her ass.

“So how was the financial retreat?” Charles asked and Lilly snapped back to the moment and they arrived in his living room.

“Oh, like it was great! I learned so much about finances that I had no idea about before.”

Charles nodded and smiled, “Oh, like what?”

“Like how silly little girls like me shouldn’t worry their pretty little heads about such matters. We should just like the big, strong, smart men take care of all that stuff for us!”

Charles nodded as they sat down on his couch, “That sounds like a good lesson to have learned.”

Lilly nodded and then got nervous all of a sudden, “It’s… it’s why I wanted to drop by and talk to you today in fact…”

“Oh?”

“Uh huh, like, your the smartest man I know and… and… I was hoping… you might, you know, handle all my finances for me…”

“Did you now? Hmmmm, well I might be convinced to, but there would have to be some ground rules…”

“Oh my gosh of course! I’ll follow whatever rules you want!” she quickly said before he could even finish his thought.

“I’ll have you on a tight leash, no more spending money on those boy toys of yours…”

Lilly blushed again, and then nodded, “Like, absolutely, no problem.”

“And when I give you a budget, I expect you to stick to it, not a penny more, not a penny less.”

She nodded and put a wicked little grin on her face, “Of course Charles, anything you say… I just have one question…”

“And what’s that?” he asked.

“Can I suck your cock now? I know I totally refused to when we were dating, but like, I’ve had such a burning need to have your cock in my mouth since the moment you opened the door…” she said and didn’t wait for his reply, her fingers going to his pants and unzipping them before she leaned over onto his lap.


“Pew! Pew! Do you like my guns baby? giggle” Lilly said as she stepped out of the pool and towards Charles.

Charles had been true to his word and put her on a short leash immediately. So short in fact that it had just been easier for her to move into his mansion.

Which worked out well because it meant she got to suck his dick a lot more!

She had also been true to her word that she’d follow the budget to the penny that he made, though there was one item in he budget that was getting harder to adhere to… the plastic surgery budget.

She was constantly getting her lips filled, and she’d done her tits and ass already, but he just kept increasing the budget every few months!

Lilly was already talking to the surgeon about her next set of tits and he assured her they’d be bigger than her head for sure this time.

She tossed the water guns into the pool and walked over to Charles in his chair, she pushed his legs apart and snuggled down between them, pushing her tits into his crotch.

He looked down and smiled at her, “Good news Lilly, it’s time for the financial retreat again this year and I’ve booked you a ticket.”

“Oh my gawd, like thanks baby! I can’t wait! giggle

Charles gave a little chuckle and nodded, “I know, and I’ve selected a special session for you too. It’s title ‘How to be the dumbest slut you can be’, I expect you to come back without a single thought in that silly little head of yours!”

Lilly squealed in you as she struggled to get his cock out of his swimsuit and into her mouth. She was sure that, just like last year, she’d learn all kinds of new things and couldn’t wait to tell Charles all about it.

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