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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. What started as something like a prostitute - customer relation turned into a wonderful and life changing experience for me and my “customer”. I know I materialized his fantasies and he eventually moved to more serious relationships and got married to a nice girl. I freed myself from my past too and started a new and happy life. John deer Male · United States of America. This is the member profile for John deer W4M in Houston‚Deer Park‚ Pasadena‚ LaPorte‚ Webster‚ Clear Lake‚ League City‚ FriendsWood‚ Pearl and‚ Dickinson‚ Santa Fe Texas 281-910-2007 I would love to meet today if possible - W4M in Houston‚Deer Park‚ Pasadena‚ LaPorte‚ Webster‚ Clear Lake‚ League City‚ FriendsWood‚ Pearl and‚ Dickinson‚ Santa Fe Texas Hunting Hunting · Incest And Taboo · Hunting So, I had lived in this neighborhood for a few years now that backed up to a section of wooded land with about 300 acres. Being raised in the country I was raised hunting and fishing every chance I had, so I took this opportunity to get back to my roots and scout out the area. I was late August so I couldn’t actually bow hunt yet but I took some cameras and my climbing stand out and went scouting. I found a great looking area not too far in from my home that had a nice stand of oak trees filled with acorns and t big beech trees both with beech nuts, so I hooked my stand up to a nice elm tree beside the beech trees and climbed up about 25 feet. I had been there for about 40 minutes and was enjoying having all the birds and squirrels running around me but I had yet to see a deer when I hear something big crashing through the woods behind me. All the animals disappeared and for a second, I wished I had brought a weapon because what ever this was it was big and didn’t care about the noise it made. Well as soon as I had that thought out popped my next-door neighbors’ son, Bobby, walking up to the beech trees. My next emotion was shit – how am I going to be able to hunt with this kid running through the woods – so I thought I would scare him. Bobby started digging around the base of one of the beech trees that had a hollow trunk and pulled out an old backpack. Things were getting interesting so I decided to keep quiet and I watch Bobby pull out a large Ziplock bag from the backpack and toss the backpack on the ground and then sat on it. He opened the Ziplock and pulled out a couple of magazines, looked at the covers and put two of them on the ground next to him and opened the third and started reading. I couldn’t tell what the magazines were but I knew from the obvious hiding and subterfuge they were something he probably shouldn’t have. Bobby laid the magazine her was looking at down and got up on his knees and pulled his pants and underwear down, then sat back down and picked up the magazine. At this point I was frozen with excitement, even though I couldn’t actually see him jacking off because he was facing me and the magazine was in his lap, I could tell what he was doing and I almost popped my zipper with an instant hard on. Then about 3 minutes later he tossed the magazine down and cupped his left hand in front of his cock and emptied his balls into his hand. I thought that this was the hottest thing I had ever witnessed, combining 3 of my taboo fantasies -voyeurism, age difference, and cumshots all in one scene, until he took it over the top by bringing his hand up to his mouth and licking all of his seed off. I almost fell out of the tree and was consciously not breathing hard so he wouldn’t notice me. Bobby then stood up, pulled his pants back up and gathered all of the magazines and secured them back in the backpack inside the hollow tree, and started back toward his home. I sat there for about 15 minutes contemplating what I had just witnessed – and honestly if I should jerk off up here in my tree stand – until I decided I needed to get down and see what he was jerking off to. I climbed down and went over to his secret stashing place and pulled the backpack out to get to the magazines. If I thought I had experienced the most amazing occurrence in my life at that point I was wrong. The magazines were not traditional Playboy types but rather they were extremely explicit and were named: Blowjob Buddies, Uncle Teach Me, and Cum for Daddy. At this point is where I decided I had to jerk off before I came in my pants. I blew a load in less time than it took Bobby and then my mind started racing on how I could see more and possibly interact with his masturbatory sessions. I took the 2 game cameras I had brought to scout for deer and repurposed them to focus on the bottom of the beech tree where Bobby was sitting and then went home with grand schemes bouncing in my head. I wasn’t able to get back out to the cameras for about 8 days, but had thought about the scene I had witnessed on a daily basis while rubbing my cock. I bought 2 new sim cards for the cameras and told my wife I was headed back to the woods for a minute and swapped them out. I wasn’t able to plug them up to my computer until the next morning after my wife had gone to work and I was excited to see that the first card was full with 140 video clips! I started watching the 15 second clips and immediately noticed that Bobby’s routine was the same and that he would come to the tree almost every day between 3:45 and 4:30. The clips weren’t the best quality but the angle was better for me to watch him jack off and it looked like each time he would cum in his hand and then lick it clean. I would jerk off twice that morning watching him clean his hand and imagining it was me doing that for him. I had to find a way to make this happen! I was obsessed with the thought of Bobby jerking off and eating his cum, so I hatched a crazy plan for me to confront him. I went to the woods early that day, around 3:00 and pulled out his backpack, sat down against the beech tree and opened all of the magazines on my lap. I was casually flipping through the one titled Cum for Daddy when I heard the sounds of Bobby coming through the woods. My heart was about the beat out of my chest as he approached, but it was too late for me to chicken out now and I had to follow through and appear to be calm for this to happen. As Bobby came around the side of the tree I said “Hello Bobby. What are you doing out in the woods today?” Bobby froze in place and turned beet red as he looked down and saw his hidden stash in my lap. He stammered a few words that I couldn’t understand then said he was just out exploring. I pulled my phone out and asked him to come over here and look at something – I had downloaded a couple of the video clips of him jacking off. He hesitantly shuffled over and I closed the magazine on my lap and told him to sit down next to me and watch a video I had. He sat down and I hit play, then Bobby began to cry. I put my arm around him and laid the phone down and told him that he wasn’t in trouble and I was sorry if he though I was going to expose what he had been doing here, I wasn’t, I just wanted him to know that I knew. He wiped his nose and quite crying but was still very upset and embarrassed. I told him how I had discovered his secret and how much I had enjoyed the show, and that I jacked off after he left thinking about it. That confession made Bobby look up at me with a bewilderment in his eyes that almost made me laugh. I explained to him that all guys jerk off, and do it a lot, and I found it very exciting to have watched him do it. Then I asked him about the magazines since I had never even seen any like that and he told me he took them from his dad’s closet. I had known Tim for 5 years now and had never sensed that he would be into any of this – but good to know for later! So, I just casually starting talking to Bobby about the magazine I had been looking at and picked it back up so we could both see it. Not wanting to make Bobby any more embossed or self-conscience of what was happening I started flipping through the magazine and commenting on what I liked. There was a full-page picture of an older man on his knees with the younger boys cock all the way in his mouth and a load of cum all over the older mans face. I stopped at this pic and said I really liked this one, it made my cock hard. Bobby nodded his head but didn’t say a word so I continued flipping pages until I got to the end and picked up the next magazine, Blowjob Buddies. This publication had all teen boys sucking and cumming on each other and was very hot. I got to a page where one guy was sitting on the side of a bed and the other was on his knees licking the head of his enormous cock. We hadn’t said a word to each other since my last comment on how my cock was getting hard so I looked at Bobby and asked him if he liked this picture. He nodded again and mumbled yes so, I asked him which guy in the picture would he rather be - the one licking the cock or the one getting licked? He turned red again – I thought we were past that but obviously not – and didn’t answer. So, I flipped the page and asked him another question: “Bobby have you ever had a blowjob?” He shook his head no still staring at the open magazine. I then asked him which of these magazines was his favorite? He just pointed to the one we were currently looking at so I continued flipping pages. We got to a page that had one guy licking up a cumshot off the others stomach and I told Bobby that I thought that was so hot. He instantly nodded his head yes so, I asked him – already knowing the answer – if he ever tasted his own cum and if he liked it. This time he nodded and spoke: “Yes, I really like the way it tastes”. I agreed with him and told him I liked the taste too. We flipped a few more pages and we got to a picture of cum dripping down from a cock onto the guys tongue and Bobby says: “That guy must like the taste too”. Good – Bobby was relaxing some. I laughed and said absolutely that it looked good to me too. I flipped a couple more pages and decided it was time to go for broke so I lair the magazine down and looked at Bobby. “Bobby, I know you came out here today to look at these and jerk off, but since I am here too, would you like a blowjob instead? I would really like to suck your dick and taste your cum.” Bashful Bobby showed back up and he just looked down and didn’t say a word, so I waited just a minute and reached over and placed my hand on his rock hard cock and told him that even if her wasn’t sure, his cock was, and I started rubbing him through his pants. Since he didn’t try to move my had or object, I told him to stand up, and he did. I pulled his pants and underwear down to his knees and his hard cock was eye level to me. The object of many a good jerk off sessions was inches from my mouth! I just stared for a minute taking in his cock and balls. His cock was about 6 inches long and not very thick, and there was just a wisp of fine hair on him, and his balls looked completely hairless. I grabbed his balls and gently pulled downward so his cock wasn’t pointing straight up then gently licked the head of his cock. Bobby whimpered and that made me even more excited, so I swirled my tongue around his head and then wrapped my lips completely on his cock. I was so caught up in the fact I was actually living out a fantasy I didn’t notice the signs of Bobby about to cum and about the third time I swallowed his cock completely I felt Bobby jerk, grunt, and shoot 3 spurts of sweet, sweet, cum in my mouth. I don’t think I had ever tasted anything as good and didn’t want to stop trying to suck the last little bit out of his balls, but Bobby was too sensitive and pulled away. He just stood there for a minute with a silly grin on his face, so I asked him if he enjoyed that as much as I did? He smiled and nodded his head yes. I told Bobby that as long as we could keep this a secret between us, I would like to do that every day we could and if he wanted it too, we could meet here again whenever time allowed. Bobby and I did meet there again, and on the 5th time I had his cock in my mouth I knew his routine and stamina level pretty well, so right before he shot his load into my eager mouth, I stopped and looked up at him and asked him if he wanted to suck me too? I usually would jerk off while sucking him and would try to time my orgasm with his, but Bobby was a fast cummer and I wasn’t, and since Bobby hadn’t answered me yet I stood up and pulled out my hard cock, and put my hand on Bobby’s shoulders gently urging him to kneel down. Bobby did as I wanted and got on his knees and took hold of my cock and stared in amazement, slowly rubbing it and feeling my full balls as my precum flowed onto his hand and arm. Bobby was amazed with my precum because he didn’t produce much if any at all, so I explained it to him and told him to taste, it was sweet. He did and the next thing I knew he had his lips wrapped around my cock and sucking like he was starving. I coached a little about teeth and tightness of his hand, but Bobby was a natural and before I knew it I was approaching the point of no return. I was telling Bobby how good he was and how wonderful it felt, and then I asked him if he was ready to taste my cum. With his mouth full of my cock he hummed a “um huh” which I too as a yes and let loose a huge blast from my cock. Even though he was expecting that it still surprised Bobby to the point he pulled off and gaged a little, while my next shot found its way across his chin. He regained his mission composure and put my cock back in his mouth and I didn’t think I would ever quit cumming it felt so good and so taboo. When I pulled out of his mouth Bobby looked up at me and wiped his finger across his chin to gather the string of cum stuck there and stuck his finger in his mouth cleaning it completely. If I hadn’t just cum, the sight of him doing that would have made me shoot a load in itself. I got back in my knees in front of him and wiped a little cum off of his ear and stuck my finger in his mouth and told him to stand up so I could finish him. He stood up and the minute I took hold of his cock the first shot of cum flew out of his cock and hit me square in the chest. I quickly dropped my head down the coax the rest out of him into my mouth and savored the flavor. This began a new era of both of us getting sucked off many times over the next 2 months, until winter set in. Not being able to conjure up a good reason to go into the woods anymore Bobby was stuck at home and I was missing our outdoor ritual, but I didn’t know a safe way to meet up anywhere else until one weekend my wife went out of town to visit her parents. I have a utility garage attached to the basement that leads into my man cave that is in the back of the house and not very visible to the neighbors, so I patiently waited on my back deck on afternoon until Bobby got home from school and called him over to the fence to talk. I had in the past paid Bobby to do odd jobs around my home, raking leaves, picking up sticks, etc... so my plan was for him to come over Saturday and pretend to pull weeds in my back beds while in reality we would go inside to my man cave and catch up on lost time. Bobby thought that he could tell his parents he was going to pull weeds and be gone for about an hour without raising any suspicions, and I asked him not to jack off that day rt the day before because I wanted a big load to make up for waiting so long. Bobby just smiled and said I should do the same! Saturday morning rolls around and I have the place to myself and it is all I can do to keep from jerking off in anticipation, but instead I ready the room for our meeting. I hooked my computer to the TV and found a clip with 40 minutes of endless cumshots and facials and queued it up for Bobby’s arrival. I opened the garage door and waited impatiently until Bobby stuck his head around the corner with a big smile on his face. I told him to come on in and shut the door and led him into my man cave. He saw the TV with the frozen screen of a cock with cum shooting out the end and he plopped down in the recliner right in front of it staring intently at the screen. I hit play and Bobby’s eyes got huge. He said there was a filter on his computer at home and he had never seen a movie before, just the magazines he found in his dad’s close so I told him to sit back and enjoy for a minute and brought him a soda. I handed him the soda and got down between his legs and pulled his pants down until his cock sprung up. It had been weeks since I had seen or tasted his beautiful cock and I couldn’t wait another minute as I licked him from the base to the tip and swallowed his cock whole. Bobby had built up a little more tolerance than the first time I sucked him and the last time in the woods he lasted almost 10 glorious minutes of me teasing and sucking him, but this time the combination of the movie, not jerking off, and not having a warm mouth on his cock for weeks was just too much and he came almost immediately. The sweet cum filled my mouth as I milked his cock for the last drop and I savored the fresh clean flavor as I rolled his cum around in my mouth. I stood up and pulled my cock out and Bobby slid to the edge of the chair and started sucking on my balls. He had become fascinated lately with my balls since they were much larger than his, and I had no complaints as I love to have my balls worshiped. I was enjoying the sensation very much and was pouring precum out of my hard cock all over his hand and Bobby used that as lube and slowly started sliding his hand up and down my slick cock while my balls were in his mouth. The visual and stimulation were too much for me and I shot a load all over the top of his head and onto the recliner without him ever stopping the tongue bath on my sack. Feeling all of the tension leaving and still tasting his cum in my mouth was a great combination as I pulled up my pants and gave him $10 for “pulling the weeds” and told him we would figure out a way to do this again real soon. I let Bobby out the back garage and came back to my room and started watching the video again while still savoring the memory of Bobby’s cock exploding in my mouth and slowly rubbing my once again hardening cock, when Bobby’s dad, Tim, poked his head in the open door and said “Bruce…we should talk”. To be continued…. lori Female · Isle of Arran, United Kingdom. Hi‚ Im visiting Isle of Arran for the next 2 weeks. Im a classic girl next door....until you see me behind closed doors. Blonde hair‚ blue eyes‚ 5 foot seven and size 8 with 34B breast. You wont want me to leave when I am through with you! I can host :) Call or text for more info. 07597819569 Looking for nsa meetups with girls that are dtf Orange County, CA (USA) · Casual Sex · Hi, I am a white male residing in Fullerton, CA and am looking for no strings attached meetups. Pleas no prostitutes. If your horny and dtf then hit me up. P.S. 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