Chapter 3: What to Wear?

New Year’s was only a few days away so I hoped Kristen would get back to me with more details. What was I supposed to wear - something formal or casual? Conservative or slutty? I’d love to have known how many guys (and girls?) there would be. Not that it would determine whether I would go or not, it’s just I would feel better not walking in totally in the dark. Fortunately she called me back the next day with more information.

“OK, here’s the scoop ... it’s just you and me in the van. Figure on maybe three or four guys with us at most. They said the party would be a lot of people - lots of girls too, so don’t worry about that as odds are they’ll be so drunk it won’t last for long anyway.”

Sounded OK to me so far. “So what do I wear?” I asked.

“Does it matter, you won’t be wearing it for long anyway!” she teased, well maybe half-teased because there was probably quite a bit of truth in what she said.

“Yeah, but we should go the same, don’t you think?”

“Well, I was planning on a short skirt and blouse, something accessible and easy to take off and get back on again,” she answered.

“Panties?”

“Kelly! You know the drill so why even ask such a stupid question,” she sighed, “We’re not going out to the mall flirting you know.”

She was right - it WAS a silly question when I thought about it. Sometimes we would go out minus the underwear when the goal was just to tease and flirt the poor guys at either the mall or somewhere else we might be hanging out at, even a restaurant. The difference was in those cases, they only got to SEE, not touch. Wednesday night would be quite different in that the idea was NOT to let them see at first but eventually they would get what they wanted, including the touching part. Sort of strange when you think about it - the better the odds of getting laid, the more clothes I wear!

The skirt idea sounded good. Shorts are always nice but after all, it WAS January and the weather wasn’t forecasted to be all the warm either. I had a number of skirts that would work so the question was, which one to wear? Sorting through my closet, I pulled out several and laid them out on my bed. It seems every time I go out on something like this it’s the same routine - debating what to wear. Sometimes I think it must be nice to be a guy - just grab a pair of jeans and a shirt and go for it, who cares if it’s been washed or worn before!

In the end, I didn’t choose any of them. Instead, I decided to go with one of my newer outfits - a skintight white dress that looked like it had been painted on me. It came down just a couple of inches or so below the bottom of my ass but it stretched so much that when I sat down, it still covered my butt while exposing my entire leg and upper thigh. One definitely had to sit with your legs crossed when you wore this one - or safer yet, don’t sit at all! It came up top behind my head like a halter with a deep plunging bust, almost like a halter bikini top except in this case, the opening continued down about six inches below my cleavage, held together with a thin webbing that revealed everything behind it.

The back of the dress was largely exposed, with it coming together just high enough to cover the crack of my ass. Actually, the back reminded me of many of the dresses worn on Dancing With the Stars where it almost looked like the girl was wearing nothing as her entire back is exposed except for the top behind her head and then nothing until you got down to her ass. It was pure white and while not exactly sheer, being so tight it showed EVERYTHING underneath like someone stretched a piece of opaque plastic wrap over me. It was easily the sluttiest dress I’d ever bought. Well, actually my dad bought it for me so that should help explain why it was so revealing.

I then picked out one of my skimpier white thongs. It barely covered my pussy but then that was why I was wearing it - to ALMOST let them see my pussy but not quite. Other than the dress and thong, the only other thing I would be wearing were some white heels. They were nothing outrageous, just three inches, but it WAS winter and it was hard enough to walk in a dress like this one without worrying about falling on your face.