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I have been given a company credit card to pay. We didn’t really speak in the cab but when we got to the restaurant he said “no more of this Mr Walter my dear. You may call me Roscoe”. We sat down and he and I ordered entre, then main meal and then dessert. We also had some wine. I was getting a bit nervous as I assumed I was the next course. Actually Roscoe was really nice and perhaps I wasn’t going to mind.“Where would you like to go next” I asked, expecting him to say back to the hotel. Instead he said “how about the casino”. I was surprised as he didn’t seem like the type. We grabbed a cab and headed down town. He was very particular. “I will sit at the roulette table. You stand behind me”. I nodded. It didn’t sound that exciting really. We entered and I bought $500 worth of chips. I liked having a credit card that I wouldn’t get a bill for. I gave the chips to Roscoe and did as he asked. He lost, then he won, then he lost again. Frankly I was getting bored. Then he had a big win. At which point he grabbed his cock and started to guide it in me. It was huge in comparison to my first and only other cock that fucked me. He applied gentle pressure, I could feel it pushing at my very tight hole. I looked up at him as he pursed his lips and applied more pressure. Suddenly there was a shock of pain. Like fire almost. I wanted him to stop but knew I also wanted him to continue. I needed his cock in me, I needed his cum in me. I clinched my teeth and let out a whimper. The head of his giant black cock was in me. He let it stay for a second, he let my muscles relax. Then he began to apply more pressure. He added more lubrication and continued to insert his black cock into me. I could feel him filling me. I could feel the weight of his dick inside me, I could feel him stretching my ass open. Then he began to slowly pull out only to reinsert. Now he was fucking me. His cock wasn't even all the way in at this point but with each powerful thrust he plunged.
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