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Chapter 27 by outa outa

As you all pile back into the car, what happens next?

A game of numbers

The Escalade hums along the evening streets, Chicago’s skyline fading into dusk as Jeff navigates toward your modest rental home. The backseat is a sea of shopping bags—dresses, shoes, lingerie—all proof of your new life as Penny. Your feet throb from the day’s marathon, but the ache feels strangely satisfying, grounding you in your new curves. Alice, next to you, scrolls through her phone, her fingers brushing yours as she leans over to show you a club listing.

“Penny, we’re just getting started. Imagine you in that evening gown, turning heads at a club tonight,” she says, eyes gleaming.

Your stomach flips, a mix of thrill and nerves. Before you can respond, she shifts gears. “Speaking of turning heads, Jeff’s been stealing glances. You should give him your number.”

Your face burns, the memory of his compliment still tingling. “I, I don’t know, Alice. It’s a lot, you know? I’m barely used to this dress.”

She smirks, undeterred. “Come on, you said you’d try flirting. He’s cute, polite, and clearly into you. What’s the harm?”

You fidget with the hem of your dress, the lace of your new panties shifting against your sensitive skin. Part of you, long suppressed and now free, wants to say yes. Jeff’s warm grin, his steady hand on your arm earlier, sparked something new. But the old Trevor in you hesitates, his influence waning but still very much a part of you. you don't know if you'll ever full be rid of him or if you'd want to be, it's like part of you dying and he wasn't all bad. “I don’t even know how...” you mumble indecisively, a compromise.

Alice rolls her eyes playfully. “Fine, I’ll handle it.” Before you can protest, she leans forward to Jeff. “Hey, Jeff, Penny’s shy, but she thinks you’re cute. Here's her number? You know, for when we need a ride... or whatever.”

Your heart races, mortified yet thrilled. Jeff glances at you through the rearview mirror, his smile softening. “I’d like that, Penny. If you’re okay with it.”

You nod, words stuck in your throat, as Alice jots down your number on a sticky note with a big hear. subtle. You feel a rush, like you’re crossing another line into this new life. You're not committed.

The car pulls into your driveway, bags piled high. Jeff helps unload, his arm brushing yours as he hands you a box of heels. “Careful with these,” he teases, and you blush again, hyper-aware of your new body’s reactions.

Inside, what’s Alice’s next move?

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