Head back to shopping

With your bellies full and a pleasant champagne buzz lingering, Alice pays the bill with a casual swipe of her card, not even bothering to read the total and selecting a tip at random. You're still not used to money being no object. Alice leads you back out to the waiting Escalade. Geoffrey is there, holding the door with that professional smile, but Alice addresses him rather than slide into her seat.

"Hey Geoffrey, we're hitting a few more spots on Michigan Avenue. Mind helping with the bags? Penny here could use some extra hands."

He nods politely, his eyes flicking to you for a split second longer than necessary. "Of course, ma'am. Happy to assist."

The first stop is a boutique called Elara Designs, specializing in dresses that scream "rich girl about town." Alice leads aggressively, pulling sundresses, cocktail numbers, and even a slinky evening gown off the racks. You try on a few, marveling at how the fabrics hug your new curves. The soft silks and cottons feel electric against your sensitive skin. Geoffrey, or Geoff, as Alice starts calling him waits outside the fitting room, taking bags as they're handed over. When you emerge in a flowy blue midi dress that accentuates your hips, Alice nudges you with a whisper.

"Go on, ask Geoff what he thinks. Practice time."

Your cheeks heat up, but you manage a shy smile as you twirl awkwardly. "Uh, does this look okay?"

He pauses, appraising you with a genuine grin. "It looks great on you, the same color as your eyes."

The compliment sends a little spark through you, he knew your eye color? Probably better than you did come to think of it. Alice winks approvingly as she has a sales associate ring up half a dozen dresses.

Next up is a shoe store a block down, where the hours start to blur. It's pushing 3 PM now, and the avenue is bustling. Alice insists you buy some heels to practice on later but lets you wear a set of flat strappy sandals out. Geoff carries the growing pile of boxes to the car, chatting more freely as the afternoon wears on. He mentions he's from the suburbs, drives for high-end clients to pay for night classes for an undergrad in business.

"So, Geoff... mind if I call you that? what's the weirdest client you've had?"

He chuckles, leaning against the car while you wait for Alice to finalize a purchase.

"Jeff is probably easier to pronounce. And plenty of stories. But you two are the most fun so far. No drama, just... good vibes."

The flirtation creeps in naturally. Well, there was also Alice pushing you onto him any chance she got, but it felt natural to you. By the time you hit a casual wear spot around 4:30 where you grab jeans that actually fit your ass, comfy tees, and athleisure sets, the conversation flows easier. Geoff shares a laugh over your struggle with a zipper, offering a hand to steady you without overstepping. "Steady there, Penny."

His touch on your arm is brief, but it lingers in your mind, stirring that warmth again. Alice notices, smirking as she piles on more bags. It's nearing 6 PM, the sun dipping low, and your feet ache.