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Although we continued to write back and forth about what we would do, if we were to meet, I felt sure that it would never happen.With that said, when the news came that my company was going to send me to Chicago, I immediately thought of Tom and secretly, of his request to me. I contacted Tom and told him that I was being put up in a hotel and asked if he would like to meet for dinner. Deep down, I knew I was getting myself into more than just a dinner bill.After the convention, I planned a few. She was intoxicating. I could feel her cock beating through her skirt. I slid my hand down and slowly stroked her cock. Her friends ran up to watch. I started kissing her neck. I could feel a little pre-cum on my fingertips. She pulled away slowly and straightened up her dress. I wanted more. " How much you got daddy?" I showed her a $50 and it got her attention. I waived it and she took it. We then got into my car. I was nervous. I couldn't believed I stroked a cock. I was thinking about it. I have a bag in the trunk if that is your choice. Also, I would like to help you relax after your flight if that is acceptable.” She peered at me, awaiting an answer.“How long is the trip to the hotel?” I asked.“At this time of day, we will be in traffic for at least another forty-five minutes, Sir.” She looked down again, her hands slightly fidgeting in her lap.“Then, by all means, my dear, you may amuse yourself however you choose.” I settled back to enjoy what I was sure would be a wonderful. Diana started to subtly flirt with Tex to see if she could read any of his "tells" better.When he had a weak hand, he'd try to throw her off by leering at her intently and making some overtly sexual remarks to try to intimidate her, but she didn't back down. On this current hand, Diana was dealt pocket Kings. When Tex opened with a mediocre bet, she decided to go all in since she held the chip lead.Tex looked at her intently. Damn it, woman ... Are you bluffin' or not? He ogled her breasts..
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