Winning the Bet Pt. 01

"Remind me again why I'm doing this?" she asked as she leaned against the doorframe to her bedroom.

"You lost the bet," I said, taking another swig of my drink. The cheap whiskey in the cola made me grimace as I finished speaking. I was sitting on the sofa in the living room of her apartment, with a nice buzz going.

"It just doesn't seem right that I have to parade around in my underwear while you sit there fully dressed." She stood up as she said this, swaying just a little bit.

"Hey, you lost the bet fair and square. If I had lost you would have made me run naked through the bar, now take your clothes off!"

"I'm not stripping for you!" she laughed, sounding insulted. "I agreed to model the contents of my underwear drawer, not do a striptease."

"Fine, have it your way. First thing, I want to see what you were wearing at work today. I've always wondered what kind of underwear you have on."

She raised an eyebrow at that and walked into her bedroom. I mentally kicked myself for coming on too strong. At the bar, we'd been flirting heavily, and she'd laughed when she agreed to my terms for the bet. Now that we were in her apartment, though, the mood had shifted. I was afraid she'd change her mind and decide I was a creep.

As I was thinking that, she walked back out of her room. The fitted white polo shirt was gone, as were her jeans. She was skinnier than I'd thought, with good-sized breasts. Her white cotton panties rode low on her narrow hips. She leaned against the wall with her arms folded beneath her bra — also white, with a simple floral texture. She seemed amused and uncertain what to do next.

"Come on, don't just stand over there, you said you'd model them for me. You've gotta at least walk over here and turn around so I can get a look at you," I said.

She rolled her eyes, and launched into an exaggerated runway walk. As she approached the couch, she stopped and turned a full circle in front of me, striking a pose like a model.

We made eye contact, and for a moment it was awkward, but then we both burst out laughing. Maybe it was the alcohol, but the whole situation was too strange to take seriously. I made a show of looking her over from head to toe. She turned around and shook her ass at me as she walked back into her room.

"What should I put on next?" she called from the bedroom.

"Well, I don't know what the options are... Why don't you put on something you'd wear on a day when you're feeling a little sexy?"

I heard her rustling around, and after a few minutes she came back out. She paused for a moment in her doorway, and then walked over to me. She had replaced the white cotton with black satin. The bra pushed her breasts together, giving her some nice cleavage. The matching panties were cut high and rose over her hip bones. As she turned around in front of me, I drank in the sight of her. From her stomach along her thighs, and up along the small of her back to her neck. Her hair was still tied in a simple ponytail. As she finished turning, she caught my eye.

"Is this what you were looking for?" she asked in an exaggerated sultry voice.

"Very nice," I agreed. "Now why don't you show me something you'd wear on a date?"

I watched as she walked back into her room, and quickly adjusted myself. I was starting to get hard, and I was hoping it wasn't completely obvious. I took another sip of my drink and fidgeted uncomfortably on the couch.

When she emerged a few minutes later, I forgot all about trying not to be obvious. She was wearing a white mesh thong and matching bra. As she walked slowly towards me, my eyes roamed over her body. The bra was mesh on top and satin on the bottom, and I could just see the edge of her areola. Through the mesh thong, I could see her neatly trimmed landing strip.

"What do you think?" she asked, with one eyebrow arched. She didn't seem to mind the way I was gawking at her.

"Um, it's very, uh, very attractive. I particularly like the mesh bits."

"I can tell," she said, with a quick glance at my crotch. I looked down and mentally cursed at the now obvious erection tenting my pants. I was terrified that at any minute, she would decide this game had gone too far and kick me out. Before I could say anything, she turned her back on me and was striding out of the room.

I shifted around on the couch, trying to find a way to sit that would make my hard-on less noticeable.

"So, what now?" she asked from the other room.

"Well, why don't you show me what you would wear for a guy you were going to bring back to your place?"

Silence. Some part of my brain was screaming at me for being too pushy. Any second now, I thought, she's going to say that's too much, and get rid of me.

Then suddenly she was walking towards me again. But this time she wasn't wearing anything at all.