Start the betting

I opened a beer and got comfortable on the couch on the side opposite Sandy still avoiding eye contact. "20 bucks a match sound good?" I asked quickly downing the beer afterward in hopes getting a little drunk would ease my embarrassment.

"Yeah, but stop hogging the beer," she leaned over and slowly grabbed a beer. Her cleavage peeked seductively out of the top of her shirt. I looked away not wanting to keep coming off as such a creep, but I noticed that as she was reaching for the beer with one hand she was discretely pulling at the bottom of her shirt letting more of her soft white bosom show. She was definitely trying to get my attention now.

I still needed to focus on the game I threw the first couple of matches to get her confident she couldn't loose to me, but after each match she awkwardly changed positions, showing off different parts of her body. And she'd permanently stretched out the neckline of her pajama shirt, but continued tugging it down every couple minutes until I could see the top of her plain black bra struggling to hold in her endowments which visibly rolled over the top. I thought she must have been convinced her little show was what making her go undefeated until she spoke up finishing off her 3rd beer, "I gotta tell you something, I've had this game a while so I already know how to play, but I feel bad taking all your money again."

This was my chance to hustle her back. "That's ok I think I'm getting the hang of it," I said nonchalantly, but noticeably drunk, "hell I just got my holiday bonus so let's make it 60 bucks a round."

"God you're dumb. Whatever, if you don't want your money I'll gladly take it," she said picking a character she wasn't very good at, at least willing to give me some kind of handicap, "but I wanna add a fun side bet. Looser has to do a truth or dare for the winner." It was an odd addition but seemed like a fun bonus to go with making my money back.