Use the rest of her clothes as betting chips

"Wait! I DO have more clothes, I'm just not wearing them!" I remind my sister.

Ashley looks at me, confused.

"What are you going on about? Of course you have more clothes, I can see them in your closet. Girl, I think you need some sleep." Ashley responds as she starts to leave my room.

"Duh! What I mean is, how about I use those in lieu of pennies. Like, each item is a penny." I suggest. I'm starting to think I might have a gambling problem.

"Em, are you serious? Do you even know what you're suggesting here?" Ashley inquires, though it's clear I have her attention.

"Yeah, of course!" I say matter-of-factly.

"So you, Emily, are totally fine with the prospect of me taking any of your clothes that you bet in the event that I win? Like, I'll own the clothes, after that point they belong to me and not you?" Ashley questions further.

"Sure, why not?" I answer. I hadn't thought much about what happens after, but that's for another time. If I win I won't have to deal with it at all! Too bad Lady Luck has been with everyone except me tonight...

"You're on, Em" Ashley says with an evil grin. "I have to admit, I didn't think you had a daring bone in your body, but even I wouldn't do something this crazy!"

I smile at Ashley. If there's on thing I'm glad about tonight, it's that my sister doesn't think I'm some boring wallflower anymore.

With that, I run to my closet and start taking my shirts, dresses, pants, and shorts off the hangers, my still naked boobs jiggling as I reached upwards for some items. I also grab my three pairs of shoes.

I've always had a modest sized wardrobe; I've never obsessed with the latest styles and fashions like other girls so I tend to have just the basics. After a few minutes, my closet was devoid of all outer garments.

In total, there were just over 30 items. This should be enough to bet with. I set the clothes next to me and Ashley, as we prepare to continue our hours long game of blackjack.

I don't know why I'm confident right now, recent history tells me my wardrobe is about to become even more modest. Still, that competitive drive keeps me from quitting this game I should have quit hours ago.

I win the first hand, meaning I now have pennies to bet instead of clothes, but after a few less fortunate hands later those are returned back to Ashley. I gulp as I proceed to bet a dress of mine and two shirts against Ashley's... pennies. This suddenly didn't seem like such a fair game, but I'm still locked in on it.

And of course, I bust, transferring ownership of that dress and those shirts over to my sister.

It doesn't get any better. Anytime I win a hand, I would lose the next few, along with several articles of clothing. Hand after hand, I watched Ashley's wardrobe size increase, and mine dwindle. Shirts, pants, dresses, shorts, and all three of my shoes were lost until I was down to only a single dress. That's it. Besides my underwear, I now own exactly one item of clothing.

How am I this bad at this fucking game? Maybe I should call it quits...