Want to support CHYOA?
Disable your Ad Blocker! Thanks :)

Chapter 2 by gystex gystex

What do you tell her?

"Remember how we talked about Role-Playing?"

"Do you remember last week," you begin, "when we were talking about trying out some role-playing?"

Doe grins. "We were talking about a lot of stuff," she says. "What exactly was it that tickled your fancy?"

"Promise you won't get mad?"

"Oh, this should be interesting. Okay, John, I promise."

You take a deep breath. "I'd like you to dress like a prostitute and meet me on the corner of 15th and Lincoln."

Doe's eyes go wide for a moment, and you worry that perhaps you've gone too far despite her assurances. Then, much to your relief, she chuckles with amusement. "What the hell," she says. "It might be kind of kinky. And it's a hell of a lot better than you going out and finding a real whore. Okay, I'll do it."

"Cool!" you say enthusiastically. "What are you going to wear?"

"That's a surprise," she says coyly. "Don't worry, though, I'll get slutty enough for you. Tell you what, though, this is going to take some prep time. Why don't we agree to meet at the street corner at around ten o'clock tomorrow night. We'll agree to act like it's the real deal; I'll be a whore, you be a customer. If we're going to do this, I want to do it all the way."

You agree enthusiastically, and the two of you spend the rest of the evening making out and teasing each other, but holding out on actual sex so that the next night can be even better.


At quarter to ten the next evening, you're driving your car down 15th past the pawnshops and adult bookstores. For the sake of authenticity, you suggested the genuine Streetwalker Central of the city, and as you cruise down the street you see a number of real working girls standing around looking for customers. It suddenly occurs to you that you might have thought things through a little better, as it's entirely possible that Doe could get into some trouble. You hope that she's smart enough to stay inconspicuous until just before ten o'clock.

As you turn around a slight bend in the road, the corner of 15th and Lincoln comes into view. You stop at a red light and peer ahead to see if you can catch a glimpse of Doe on the corner. At first, you don't see her, and you wonder if she's bailed on you.

Then a figure in the shadow moves, and you see that it's a woman in an overcoat. She hesitates for a moment, and then pulls the coat off and drapes ot over the bus bench next to her. It's probably Doe, but if you hadn't known she would be there, you never in a million years would have recognized her!

She's wearing a tight leather jacket over what looks like a red PVC halter top, showing considerable cleavage. Her black skirt rides low on her waist and high on her thighs, and you're certain she couldn't bend over without showing everything. Fishnet stockings and knee-high leather boots with spike heels make her nicely-toned legs look hot and sexy. When her face turns in your direction, you see that she's done up her lips fire-engine red, and her blonde hair is teased and even spiked a bit into a wild style. She definitely looks a bit nervous and self-conscious.

The light turns green, and you approach the corner with much anticipation...

What happens now?

Want to support CHYOA?
Disable your Ad Blocker! Thanks :)