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This time I took the dress and top with me as well as the make-up kit. I arrived holding my backpack and went straight to the restroom. Several minutes later the new me was ready. I left my backpack at the bar and sat on a table enjoying a cocktail. I was feeling stunning, wearing my midi dress, black stockings and a sexy top skirt. I was looking feminine and I was feeling sexy, I understood that I was looking sexy as well by the guys as many were hitting on me. I spotted a nice one, mid 30s to 40s and decided to make a move. He was married, from another city visiting some relatives here and he decided to come at the bar “for fun”. We talked for a while and he proposed to go at some hotel together, I didn’t want to as I was not sure if they would request me some i.d. at the front desk. I was also afraid to ask him over at my place as I barely knew him, not to mention that someone from the neighborhood could see me. He suggested to go at some place with his car. We ended up in a. I thought,” Kerri started to say.“He told me to fuck off, and that he didn’t need my pity, and that I’ll get my money. That’s what he said, so…”“But I was…” Kerri’s husband started to say.“Well, whatever you were, that’s what you said. So either you win it all back tonight, or prepare your co-workers for an uncomfortable visit tomorrow from a debt collector. ...That would be Tiny, in case you’re bad with riddles.”“What do you mean, win it all back?” Kerri asked.“I like your idea about gambling with you,” I told Kerri. “Frankly, it makes my dick hard. And now I want to find out if my fantasies about you match up with the real thing,” I said. “I want you to suck my dick until I cum in your mouth.”“No,” Kerri said. “Not happening.” “It might not! That’s the gamble. Not if your husband wins. One game of blackjack. He wins, I forgive the debt. All ten grand. I win, you suck my dick and swallow.”They both remained quiet, which I took as a sign of victory. “I mean my God, it’s just a blow.
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