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Her name was Tiffany, it was clear she was an escort but I didn't care because I wanted her and I had the money.I bought another bottle of champagne and we went upstairs we ended up fucking until daylight and it cost me a $1000 but it was worth every penny.In the morning we talked about sexual fantasies and things we'd done in the past as she stroked my cock. She told me about how she'd once gone down on one of her friends at the request of a client. She then asked if I'd ever been with another man. At first I said no but she could tell I was lying. By squeezing my cock she managed to get it out of me about my cross-dressing days and how I'd pleasured men. To my surprise she was turned on and pumped my cock harder until I covered my stomach in cum. Tiffany swirled her finger in my cum and put it to my lips."Maybe you'd like to have this experience again again yes? Tiffany said with a big smile on her face.I told her maybe but I had no clothes or make-up and it was nearly 10 years. He stuck his tongue in my pussy as far as it could go. He licked my clit and fingered me as my orgasm began to rise. "Chase I'm cumming, I'm cumming." He started finger fucking me as fast as he could and I screamed in pleasure as my orgasm took over my body. Chase kissed his way back up my body and removed my bra. I took off his shirt and pants. He stood up and took off his shorts and boxers. He kissed me passionately. I felt how hard he was and I tensed up. "Bri, are you a virgin?" He looked a little surprised. "Yeah." "Don't worry. I'll be gentle." He kissed me placed his cock at my wet entrance and he pushed the tip inside me. I gasped at how big he was. He was about 9 and 1/2 inches. He pushed a little further until he reached my hymen. He stopped. "Do you really want me to do this?" I shook my head and he with one thrust he ripped through my hymen. I screamed as pain took over my body and I dug my nails into his back. He paused just to let pussy stretch far enough. He fucked.
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