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The day I pretended to be a prostitute The day I pretended to be a prostitute · Mature · This story happened about 7 years ago, when I was still married. I was at a bar waiting for a friend. She texted me and apologized because she couldn’t come. So, I just stayed there, alone and sad. I watched all the young and happy people. They were enjoying their lives, while I was stuck in an unhappy marriage. As you probably know from my other stories, I have a thing for much younger men. I kept looking and imagining myself with some of them. I had a few drinks, which perhaps made me a little inattentive of how I was acting. I kept starring and smiling at young men without realizing I was doing it too obvious. I was a fat woman in my late 30s, so that was awkward. Suddenly a young African American man approached me: “So, you are available?” “Huh?” “50 Dollars?” “What?!” “I have a place nearby.” “What are you talking about?!” “Sorry. Never mind.” He went away. I was so distracted that it took me a few seconds to realize what had happened. He had mistaken me for a prostitute! I felt ashamed and noticed that I was acting suggestively without realizing it. All that starring and smiling at much younger men had given him that idea. I was a little ashamed and starred at the table. But I realized there was one good thing about the situation: A young man had found me attractive enough to pay for me. He wasn’t bad looking and reminded me of a good relationship I had with my first boyfriend, who was a nice young African American, in my twenties. I thought about the situation for a few minutes and it became less and less awkward. I was willing to be with him, but not as a prostitute. But I was too shy to simply tell him that. I also had a fantasy about being a sex slave for a strong dominant African American man. I thought perhaps pretending to be a prostitute could create a situation like that. I came to a conclusion: The only way to overcome my shyness and make him act like the man in my fantasy was pretending to be a prostitute! I stood up and went to him: “Okay, let’s go.” “So, you are available?” “Of course.” I was afraid that people may notice what was going on, so I went out of the bar and he followed shortly. “Why did you reject me the first time?” “I was afraid you might be a cop.” He was muscular and had a serious face, so that made sense. We went to his place, which was nearby. I think he realized that I was acting a little strange. I was happy, with a big stupid smile on my face. I haven’t met many prostitutes, but I don’t think they have such a big stupid smile on their faces when they are with their customers. He took me to his bedroom and began undressing. I couldn’t believe what I was about to do. Despite not being happy in my marriage, I had never cheated on my husband, but now I was with a young stranger (perhaps 15 years younger than me) and ready to surrender myself to him. I was lost in my thoughts when he brought me back to senses: “What are you waiting for? Undress!” “Yes sir!” I began to take off my clothes. I revealed my body to him little by little. I was fat, and my face was average looking at best. Therefore, his interest in me excited me and made me feel better about myself. We both striped down to our underwear. He waited for me to continue. I opened my bra. I knew men were interested in my breasts more than anything since I was a teenager. I noticed his erection after seeing my breasts. It was comforting to know that my old breasts could still attract young men. I was a little ashamed to take off my panties, but I just forced myself to do it. He took off his underwear as well. His cock was big and fully erected. I really missed the sight of such a cock which I had fantasized about for years. He asked: “Are you okay with kissing? I’ll pay extra.” I was thrilled to hear that. I remembered what a good kisser my first boyfriend was. I was eager to repeat that experience, so I responded positively. We hugged together and started kissing. I locked my arms around his head and he locked his arms around my waist. It wasn’t purely artificial. We kissed like a boyfriend and girlfriend. He moved his hands down and grabbed my butt cheeks hard. It lasted a minute. After that he asked me to sit on the floor. I sat in front of his big erected cock. He grabbed and bundled my hair. It was a little painful, but as I said, I liked him to dominate me. I opened my mouth and he pushed his cock in it. That was the biggest cock I ever had in my mouth, which scared me a little. I think my eyes widened which probably made my face looked scared and funny. He laughed at me as a result. I started sucking. It was good – both the taste and the feeling. I had not done something like this for so long that I had forgotten how it’s like. In my thoughts, I looked back at my life for a second and regretted that I had deprived myself and the others from such a pleasure. Such a regret gave me even more motivation for making the most out of this situation. I raised my hands and grabbed his butt cheeks, showing my eagerness in sucking his cock. He noticed my eagerness and encouraged me with his words: “That’s it bitch! You should be paying me, not the other way around! Suck that cock! Suck it hard!” He began pumping his cock in my mount as he was talking. He also forced me to move my head back and forward by dragging the bundle of my hair he had in his hand. Sucking turned into throat fucking. This was the first time I was doing it. It was hard but I managed to last. He cummed in my mouth. There was so much cum. I swallowed all of it. I was so distracted that I had even forgot to ask him to wear a condom. But I didn’t care anymore. He asked: “Did you like it?” “Yes.” “Such a horny bitch! I bet you would have followed me without needing any money.” “I would, probably!” “Come here!” He stood me up, turned me around and grabbed me hard from behind. He held me firmly, his left hand grabbed my breast and his right hand went for my pussy. He began fondling my pussy and squeezing my breasts as he kept kissing my neck from behind. He knew exactly how to play with my pussy, even better than myself! I moaned, and my moaning became louder as he increased the speed of his fingers. It had been years since I had such a pleasure. After a few minutes, I reached an orgasm, which came with a scream-like moan. He turned me around and we kissed again, this time it lasted much longer. If someone could see us like that, he probably would have thought that we were a happy couple, and certainly not a prostitute and her customer! He asked me to lay on the bed and began playing with my breasts. He kept squeezing them and sucked my nipples. After a few minutes of playing like that, he put his cock between my breasts and pushed them together, locking his cock in the middle. He started pumping. For me this was more funny than sexual. I laughed a little. He noticed it and said: “Is that funny bitch? Wait till my cock is up again. We’ll see who will be laughing then!” His cock wasn’t fully erected after his first orgasm, but it was getting there, little by little. He sat me on the ground again, threw a condom at me and said: “Hurry up! That’s your job, unless you want me to fuck you bare!” I opened the condom, sucked his cock a little until it was fully erected again, and put the condom on it. He asked me to lay down on the bed while he was standing next to it. He put a pillow behind me, so I could be positioned right. After that, he put my legs on his shoulders and tried to penetrate me. That was certainly the biggest cock I had until then. It was painful. He was probably expecting the widened vagina of an old prostitute, but I was too tight. “Damn! You are too tight. Don’t get many customers?” “Ahhh! I can’t take it!” To his surprise, he noticed that I really couldn’t take it like that. He went to his kitchen, soaked a paper towel with cooking oil and rubbed his cock with it in order to lubricate it. We tried for the second time. This time I was determined to do it. He put the tip of his huge cock on the entrance of my pussy, then slowly pushed it inside. It was still painful, but pleasing for me. He moved it back and forward slowly in order to familiarize himself with my insides and prepare me for pumping. My legs were up on his shoulders and he was squeezing my breasts with his hands. That excited me and I felt my pussy leaking juice, which could have eased things further by lubricating the way for his cock. He slowly increased the speed of his pumping. It was still a little painful but the pleasure was so great that I could hardly feel it. “Yeah! You like my black cock in that tight pussy bitch? I bet you never had anything like it!” “Oooh! It’s great! Fuck me!” “I’m gonna fuck your brains out! I’ll tear that pussy apart!” He was now doing it so fast and powerful that it felt like I’m being fucked by a fuck machine! I started to moan loudly. This was the kind of sex I wanted and had fantasized about it for years. He kept fucking me until I reached my second orgasm and he cummed shortly after. We were both very tired and sweating bad. We fell next to each other. He told me that I was the best whore he had in his life. I asked him why he picked me when he could have picked a young and prettier girl, and more importantly, he was handsome and didn’t need prostitutes for sex at all. He responded that he had a thing for fat white MILFs and I fit perfectly in that category! I admitted that I’m not a prostitute and explained why I had to act like one. We both laughed at the situation. He regretted that he had no energy left for my ass. I told him that I was anally virgin. He insisted on taking that virginity, and I was eager to complete my experiences that night, so I suggested doing it with a cucumber. He soaked a cucumber in cooking oil and fucked my ass with it. I was never a big fan of anal sex, but I enjoyed letting him take my virginity and at least got a general idea of how it’s like. He also spanked me a little before penetrating me with the cucumber. I slept with him that night. We made an arrangement to see each other again. We kept seeing each other for some time and had sex pretty much the same way we had the first time. The sex was great and made me realize what I had missed in my life sexually (not to mention the other and more important aspects of life) and encouraged me to free myself from my miserable marriage, which I did eventually. 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