A Challenge

"I think I need to see a little demonstration of your skills," she continued. "To prove you are the ladies man you claim to be."

"I would love to have you by the manor," you reply. "You could see first hand the devotion my harem has for me."

"Oh, no no no," she chuckles. "I'm not talking about in that controlled environment of yours. I mean in an unexpected situation with someone you haven't spent hours researching. Perhaps... right now?"

Well, this was not what you had been expecting. Usually, the girls were so taken aback by your offer that they went along with the path you had laid out. Never before had someone actually challenged you so directly. While a risk to the plan, it did give you confidence that you had selected the right manager.

"Do you have someone in mind?" Is all you say.

"I do actually!" Looking quite proud of herself, Madeline jerks her thumb towards the bar. "Pink hair. Fishnets. Can't miss her."

Looking over the brunette's shoulder, you do in fact spot the girl in question, sitting her bubble butt on one of the bar stools. She is currently twirling that bright pink hair of hers as she chatted with some friends. She was cute enough, with perky tits hidden behind a band shirt. With pale skin and long legs, you could see why you weren't the only man at the bar with their eyes on her.

"Her name is Jane," Madeline continued. "She's twenty-two and a complete tease! I've been trying for like two months to get with her and nothing. She just flirts for a bit before moving on to the next suitor."

You raise an eyebrow. "If she was entertaining your advances, do I even have a chance?"

"Oh, come on, I'm not that mean!" She laughs. "Don't worry, she's bisexual. I think. So, y'know, even playing field. If you can take her home tonight, I'll consider your skills satisfactory and we can move forward."

"And if I fail?" You ask.

She just shrugs. "Let's just say I wouldn't recommend it!"

Seemingly stuck in this situation, you take a moment to size up your prey. Paying attention to her movements and mannerisms. Studying her outfit. Everything down to the drink she ordered. It had been a while since you had operated without prior research. You hoped your skills were just as sharp as they had used to be.

Mimicking Madeline, you also down the rest of your beer. Then, after straightening your shirt and fixing your hair, you head over to the bar.

And here you were thinking this was going to be difficult.

You had played Jane like a fiddle. It quickly became obvious that she was an attention whore with daddy issues. Behind a bubbly, bratty facade was a needy girl **** for approval. Honestly, she might even fit in well back at the manor... but that was a thought for a different time.

All you had to do was appear unaffected by her attempts to tease and flirt with you. Her interest in you only grew from your apathy, an interest that quickly grew into desperation. When you finally did turn on the charm, she was putty in your hands. You were done in less than an hour, with Jane agreeing to everything you suggested. While she said goodbye to her friends, you walked back over to the booth victorious.

"Well, I must say I'm impressed," Madeline admitted, sipping a fresh Guinness. "You certainly know what you are doing."

"Like I said, talent and determination."

"Yeah, yeah," she chuckled. "Well, I guess have fun and call me in the morning. We can talk about some more details then."

"Oh no, that's not how this is going down," you reply, a knowing grin creeping into your face. "I just closed out your tab. Get your purse, we're going to your place."

Madeline nearly choked on her drink. "W-wait, what? My place... you don't mean?"

"Like I said... I'm very good at what I do!"