Brenna's Way

You decided to toss the ball into her court and let her lead. You weren't really sure what she had in mind, but she seemed pretty confident that she could fix this confidence issue of yours. To that end, the first thing she did was take you clothes shopping. It wasn't that you dressed poorly; it was mostly the opposite. As a lawyer, you were always dressed quite formally. But this town was far from formal.

A polo here, jeans there— maybe even a V-neck or two, "the goal is to get you comfortable in your own skin without the help of fancy suits." You'd stepped out of the changing booth in a simple shirt and pants, but you could have sworn you saw her bite her lip when you got out. "You look good."

"Just good?" You teased, playfully raising an eyebrow.

"Okay, fine: you look really fuckable. Happy?" She stuck out her tongue as she shot back.

Her comment caught you a bit off-guard. All you could do was respond with an awkward "you do, too."

"Don't get all bashful on me now. We haven't even gotten into the hard parts of this electoral race," she laid her hands on your chest and looked up at you. "Confidence is the bare minimum that you need to get. Lucky for you, I have a pretty good way of building confidence."

Whatever you were expecting, it wasn't a bar in the city. "Tonight," she said as she pulled off and pocketed your wedding ring, "you're not married. You're just a handsome guy looking to flirt with some pretty girls. Maybe get some numbers. Whatever. But it's about time you saw what everyone else saw." She gave you a wink and then walked back out. She'd said she'd come and get you in a few hours.

You felt really awkward about this whole thing. You knew it was really just to build your confidence, but you'd never actually done this before. "How about we start with her over there?" Brenna directed your glance to a young woman off by the bar. "Why don't you go talk to her? Just be yourself!"

For all of her confidence, Brenna was nervous. She needed you to be somewhat in-charge and dominant. Ultimately, she wanted to see just what she had to work with. There was definitely the potential for things to go south, but she could step in if she needed to... she hoped she could, anyways.

You walked over to the woman, though you were still a nervous wreck. "Hey, um..."