There's still the underwear

Fuck. I'm such an idiot. How do I manage to give away all my clothes, save for my underwear? I can't go to school in just my underwear! I mean, technically I can as there's no real dress code, but I absolutely will not if I could help it!

Wait, my underwear! I still have my underwear! I have about ten pairs of bras and panties, that should be enough to win at least one hand. I'll just ask Ashley to lead her bet with an item of clothing, she's nice enough to do that for me. All I need is just one or two pieces of clothing and I'm golden, and I can just go clothes shopping after school.

"Ashley wait!" I exclaim. "I still have something to bet!"

"You do? Pretty sure I just cleaned out your wardrobe, what else could you have?"

"My underwear! I still have like ten pairs!"

"... you can't be serious, Em."

"I am! I just want to play enough to win an item of clothing back. You'd at least do that for me, wouldn't you Ash?"

"Oh alright. But same rules apply. If you lose I'm taking your underwear, and it's up to you to get clothed. You really need to learn to control your gambling habits." Ashley says sternly.

I run to my dresser and take all of my underwear out. 10 pairs equals 2o pieces of underwear, probability says there's no way I don't win at least one hand!

Ashley and I play the last round of blackjack for the night, this time with the last of my clothes on the line. I shudder thinking about what would happen if I manage to lose every hand.

What happens next?