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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.
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Milestone Milestone · General · That is what it is, a milestone of life that requires something put into the bucket list. My forty fourth birthday, the entrenching realization of middle age setting in with a building sense of urgency to experience something or anything that can check mark a life with enough excitement to carry oneself for that long steep decline of age. Maybe a long ways to go, but I was bound and determined not to go gently into that good night. So I forced the issue, demanded to my family I needed to do something…anything. Thought about a cruise…everything was booked on the major lines for a year or so. Looked into an all-inclusive…the choices were slim, none for the bigger names, but found an opening in one obscure resort that actually got my blood moving. My husband said that I should do my research and then book it if I wanted, just make sure it would fit within our schedules. I booked it. Only problem was it would be tight for my husband. He was scheduled for a business trip that at the earliest would put him there late on the first day of the ten day reservation. And unfortunately, he would have to leave before the ten days were up. He told me, just in case, to book both of us on the flights as if we both could make it and if not, he would take alternative transportation and we would just eat the added cost. The resort sounded idyllic…nestled on a secluded area of a small pristine island in the Caribbean. Even though it seemed to be small there was the option of using an adjoining resorts facilities and entertainment events. The one caveat, the other resort was described as pretty risque…promoted their beach as a “clothing optional” area and called their events as “excitement for swingers at heart”. This raised the hair on the back of my neck…in a good way. Thought that this just might be the thing to spice up our lackluster sex life. My memory raced back ten years and pulled out a chapter in my life I never really shared, to my knowledge, with my husband. I had a three-month affair with a co-worker, he was fresh out of college and the company had me as his mentor before shipping him off to a territory. In reality, he mentored me. He might have been eight years my junior, but his eight inches had decades more experience than me. Never fails, even after ten years, the thought still excites me. Still, there is always the lingering guilt. Not necessarily the infidelity part, but the fact a month after he left, I had an abortion. Did not take much of a jump to know it was his, my husband had a vasectomy when I was pregnant with our fourth child. So it was obvious that the fetus was not his. So the thought of a hedonist resort next door got my juices going. Maybe my husband could be persuaded into a little extracurricular activity…and I could use it as an excuse to pursue my own illicit desires. I visualized myself with all kinds of different guys, in quite a few different scenarios. The weeks leading up to our trip pretty much wore out my vibrator. Then the planning of the trip started to hit speed bumps. My sister was going to “baby sit” my sons and daughters, but then her mother in law had an accident. Thankfully, after a week of stress, I found refuge with one of my friends. But Mark was without a place, or should I say, someone to watch over him. Granted, Mark was just about to turn eighteen, just so happens two days after my own birthday. When I would be on the island. Still, there was no way I would leave my man-child alone in my house. Already knew he was not a virgin, and without a doubt he had a lot of girls to choose from. I did not want him knocking up some girl and suffering the rest of his life. Five days before I was to leave, a friend from work offered to take him in. I was kind of skeptical, because at times Julie seemed to be just a little bit oversexed. Even though she was married, I had caught her looking at Mark as if she was a wolf salivating over a large steak. Or as she kept telling me, she was a Cougar on prowl for the next cub. The next day, my husband called…he would not be able to make it to the island until the middle of next week at the earliest. At best he would have maybe two full days. Great…maybe I should cancel too, ran through my mind, the disappointment must have resonated thru the phone. My husband caught it, and then he hesitantly suggested that I go on the trip. The rebuttal never made it past my larynx…my mind already envisioned myself as a wild animal feasting on tender flesh. All that escaped my mouth was a sharp grunt. It was not a grunt of objection. Still, he sounded conciliatory and then asked if Mark was taken care of because maybe he could go with. I quickly tried to think of an excuse, since I did not tell my husband about my fantasies or the neighboring resorts enticing assets. Shit…hell…I really wanted to go. Told him that I would ask Mark, but he probably would not want to go with his Mom. I was wrong. That evening Mark gave an exuberant, resounding yes to going. He read the brochures…and Mark being Mark, could not wait to check out the place next door. Even though that was my same intention…I shook at the thought of my son chasing naked women in my presence. But…if I wanted to go, guess Mark would have to tag along. Started to repack my stuff, did not think that I would need to bring some of my more intimate items, but then pulled out the string bikini I had bought for just this occasion. I thought about how I looked when I had tried it on…this might be the last time I could get away wearing something like this…hell, I flat out looked dynamite in it. To heck with it, son or no son, I was not going to let him stop me. It was just a little amusing when we checked in at the airport, the travel itinerary said Mr. and Mrs. We both laughed, but then again he is a Mr. and I am a Mrs. Joked about it during our travels too. Kind of played it up also, when they called us to the flight desk by Mr. & Mrs., we walked up with our arms around each other just to get a response. I got a positive wink and nod from the attendant behind the counter…then she leaned over and whispered in my ear. “I’m jealous…have fun with your cub”. Don’t know why, my vanity or whatever, but as we turned I grabbed Mark’s ass and gave it a squeeze knowing full well the attendant was watching. Mark jerked from surprise and then mouthed “what the hell, Mom”. I just playfully smiled back. When we got to the resort and checked in, we were still listed as Mr. & Mrs. But when the gal asked for our room preference, I said two beds. She looked quizzically at me and then mentioned that the only room left with two beds is the special needs one. Great…put a cripple out or share a bed with my son. I asked, “King size?” Glad I did it, our room was awesome, the double doors opened up to the beach. The other resort fence was not more than a few feet from our porch. The iron gate that separated the properties was only twenty feet away, the open bars offered a tantalizing peek into the hedonic environment. Just on the other side of the gate, a muscular man standing totally unembarrassed…completely nude, his gorgeous penis swinging in front of him as he talked with buxom naked woman. I could not take my eyes off of them, I was mesmerized…so was my son. Then he talked, “Wow…nice tits…this room is fantastic”. I hit him in the arm and feigned anger, “Mark…that is not something you say in front of your Mother!” “Oh, I am sorry, “ he faked having any remorse; “you have nice ones too”. “Nice what?” I had thought for a second I might have heard him wrong. “Tits…you have nice tits too, Mom”. “Mark…I am your Mom…stop it. Anyway, how would you know?” I quickly scanned my memory banks just in case. “Just guessing”…then slipped in, “but I am sure I’ll find out”, as he tilted his head towards our neighbors. I was just a little flabbergasted, but to be honest, a little proud that my just about eighteen-year-old son thought of his mother being able to hold her own. I quickly took stock of the room. It was not laid out for those with even a smitten of humility. There was a large tub, big enough for multiple people, totally exposed in the corner of the room, right along side a glassed in shower stall. Thought that there had to be a bathroom somewhere. Sure enough there was one, but behind the door was just a toilet and sink. Suppose that I would be using the fresh water shower down at the beach…no way I would use these in front of my son. Mark must have correctly read my consternation, a goofy smile stretched across his face as he looked at the tub and then at me. “Not in a million years, bucko”, I intentionally spit out to make sure he did not get the wrong idea. His face contorted into a pout. “Jeez Mark…I am your Mother for Christ’s sake” but I was actually amused at his reaction. At this point of time, there was not a deviant consideration in any way or form regarding the possibility of even remotely contemplating something physical happening between my son and I. But…this short back and forth, his expressions and my verbal responses were in a playful mode. So my antenna never went up in defense so to speak. Ok…we were settled in and I wanted to go to the beach, have a cocktail, unwind a bit from ten hours of total travel time. “I do not know what you want to do, but I am going to relax on the beach” I said more to myself than Mark. I grabbed my suit, hesitated when the skimpiness of it hit me, then told myself what the hell and went into the bathroom to change. Putting on my, err...my suit if you can call it that, as was obvious in my reflection of the mirror that this attire would not be socially acceptable around children back home. Especially considering one of them could possibly be my almost adult son. Heck, the small triangles covering, barely covering enough of my breasts to hide most of my areola’s, did nothing to leave the size of each of tits to the imagination. My full “C” cup mounds were pretty much out there for display. I wondered for a second if the small strings had enough tensile strength to hold them up. Scanning down and making a slight twist…the string running between my legs and up my ass crack was nowhere in sight. Fortunately, for my age, my exposed ass cheeks still had enough firmness, so as not to look as though I had saddlebags dragging behind me. As I turned back… even though I had thought I had trimmed and shaved my lower part back home, the small tuft of hair on my pubic mound could be seen just above the couple square inch patch of cloth covering me down there. Shit…too late now. I pulled the bottoms off, lathered up a little and with only three of four passes with my razor…my vaginal area reverted back to pre puberty. Gathered myself up and opened the door. I do not know who was more surprised. Mark apparently had decided late that he could quickly change into his swimsuit and figured by standing in front of the bathroom door, he could block it just in case. That did not happen, I swung the door harder than anticipated, it hit him in the head just as he was bending over to pull up his swimsuit. He went down on his back…his swimsuit around his ankles. My son’s penis flopped in an arch to his belly; I could not stop my eyes from focusing on it. My God, my son’s dick is bigger than his father’s is all that came to mind. Then it started to grow. Mark’s mouth was gapping open…he…he was staring almost in a mesmerizing way. Yet his eyes coursed over my torso…then I realized my jaw was slack too…Holy Shit…my son’s cock was now rigid…it had to be close to my ex lover’s…I shook my head coming to my senses. This all happened in less than a minute. I gurgled out, “Ah…sorry, should not have opened the door so fast. Uhmm…let me get out of your way” as I stepped over him. In and effort to not step on him…had to look, my eyes automatically went back to his cock. My psyche tried in vain to supplant morality for the lustful vision of my own son’s penis floating in my brain. Damn…I needed a drink. Made it down to the beach, spread a towel on a beach chaise, adjusted my sunglasses, and got comfortable. The first daiquiri soothed the quandary of my conflicting thoughts and started me on the path to ignoring some of my inhabitations. I rationalized that maybe my multiple week build up of expectations might have triggered some psychosis, so to get my mind off of “that” penis started to recon my surroundings. From my vantage point, not fifty feet from the wall separating the two resorts, I had an almost unrestricted view away from the neighbors, but towards the neighbors the wall blocked the angle to seeing more than a few feet of their beach. I actually thought about moving the chaise closer to the shore in hopes of visually intruding on their privacy. With a warm humor coursing through at the deviant thought, could not help but smile. But, better check out the locals first. Most of the patrons, from my resort, seemed to be a hundred or so yards away, accept two couples that were maybe twenty yards away. Noticed the two guys as I was originally walking onto the beach when one of them elbowed the other and nodded in my direction. It fed my ego immensely and it was all I could do so as to not let on. Thankfully my large, dark sunglasses allowed me to check them out without them knowing. As I settled in with my second daiquiri I had assessed the couple to be beyond the honeymoon stage and before the children raising stage at most in their late twenty’s. The two women were so engrossed in their own conversation; they completely ignored their two male partners standing with drinks their hands a couple of feet into the turf. Did not take much of a leap of logic to know that from the two guys vantage point, they had a direct line of sight to the “clothing optional” beach next door. From my standpoint, they appeared to swivel their heads in my direction more often than down the beach. Could not help but to check them out, mid to late twenties and physically fit, there was much to see. Let my mind wander as to what they might look like without their hip hanging swimsuits…where they hung? You think they would be interested in a “older” woman? Wonder if they would be interested in a threesome? That thought came out of nowhere…had never contemplated having two guys at once. The thought tickled my senses right down my spine. My nipples tightened at the thought. A quick glance at the women, they were completely in oblivion, and with the help of liquid encouragement I stood up and walked towards the water. Could have just gone right in front of me as I could feel their eyes capturing my every move. But…what the hell, let’s see just how interested they really are up close. So I altered my path to within feet of them, making sure that my movements yielded more sway than necessary and not in anyway disguising my sexual intent. My nipples were in full erection and had their full attention as I approached. While walking by, in a very planned move, I turned my head towards them lifted my sunglasses and checked out the front of their swimsuits. Raising my head I gave each a smile and wink then broke into the surf. The water was extremely warm, but felt good and still cooled down my libido a tad. Could not help feel a little of accomplishment at seeing the tents rise in those complete strangers. Movement to my left caught my attention, it was a couple over at the other resort, and even though they were quite a distance away…there was no question as to what they were doing. His back was slightly turned towards me but I could see her, and one copious tit bouncing unencumbered to each thrust he made into her. My audience was distracted…do not know what made me think they were “my” audience or why I should even care, but like a little kid throwing a tantrum for attention, I had to do something. I pulled off my skimpy top, stood up, and rubbed my tits as if they were covered in sand and I was cleaning them. It got their attention; I slowed the rubbing, their eyes glued to my chest. Brought a devious smile to my face…then to theirs. Did not last long, one of their women saw what was going on. She barked in a not so pleasant manner…like puppy dogs both the guys turned and shuffled back towards them, their heads down as if in guilt. Even from this distance, I could feel the daggers of anger coming from the eyes of the women. Oh well…so much for that. Returned my attention to the couple obviously fucking in the surf. Like a bug to a light, my feet moved me closer to them, my curiosity greater than my caution. As their details came into focus, my feet froze. The female was the one that Mark and I saw by the gate, she had to be at least my age or greater…the guy…it was Mark! I did not know how to handle this…was I jealous? Not because of my son necessarily, but more from me being extremely horny from teasing a couple of guys. All of which I knew deep down, due to the condition of having their female partners right there, nothing would have come from it. And here my son was, getting what in my mind was the real reason I wanted this trip. God damn, this woman…she was living my fantasy, not of my son but a young cock plying its hard youthful strength deep into her vagina…and not mine! Like stuck in a state of suspended animation, I just watched. She was driving down more and more violently as my son reciprocated, her head thrown back to the sky. Mark was peppering her neck, upper chest, with nibbling pecks. Then he closed around her nipple…pulling it between his teeth. I shivered at the thought of someone doing the same to me… Her breathing, even noticeable from my distance, had changed to gulping…then she arched hard against my son. My God…she just climaxed. Mark just froze and held her…did he cum too? A few minutes passed, they were still enjoined, her head now resting on his shoulder catching her breath. I could see Mark’s lower torso start almost imperceptibly to oscillate. The woman made a small whimpering sound. His oscillating movement was now interjected with an occasional thrust. She coughed up a grunt. On the second thrust, she raised her head, her arms around Mark’s neck. Their lips connected and by the third thrust they were locked into a full embrace. I watched as the crescendo built, first it was a few oscillations to every thrust, but as minutes passed, it was down to one each. My one hand was now between my legs, rubbing my fully swollen clit. I was not thinking from the stand point that that was my son fucking, it was just a cock that should be in here…as I stabbed as deep into my cunt as I could while rubbing my clit with my thumb. Any pretense of him oscillating his hips were now gone…he was just pounding, hard and long strokes as deep as he could into her. She was back to gulping air, her fingers digging into Mark’s shoulder. He definitely did not care. Just a few strokes later, could have been more but my own orgasm washed over me, a unfiltered screech came from her mouth as she arched her back at the same time my son arched his and growled grunts in conjunction with each spasm of his tightening ass cheeks. I came with the thought of each jettison of that man gunk spraying the inside of my womanhood. Their uncoupling was as if in slow motion, the woman dropping her suspended legs back into the surf. My son’s, still swollen, but semi flaccid, cock plopping out from between her thighs…a glistening string of goo reflecting in the bright sun. The woman saw me; a smile broke across her face. She reached down and held my son’s still ample cock as if offering it to me. Mark turned his head in the direction her attention, a moment of confusion on his face, a split second of guilt, then a slight smirk as his eyes cascaded down the front of me. My hand was still between my legs…the bottom of my swimsuit nowhere near me. An immediate flush of embarrassment came over me. I turned and made quick movements to the shore…my bottoms had washed up to the waters edge, I just grabbed them and a towel to wrap around me as I hurriedly made my way to our room. An hour later, my composure somewhat recovered, I was sitting on a chair when Mark came back in. The previous hour had started with dealing with my embarrassment to finishing with how I was going to deal with Mark’s apparent voyeurism. Any thought of using the emotion of embarrassment on Mark was immediately dispelled when Mark walked in. He was completely naked. His relatively large cock just swinging in front of him. He made absolutely no attempt to cover up; in fact he was making it a point to give me total views of it. I tried to look away, but he stood directly in front of me, his hunk of meat in my peripheral vision. “Mark…is it necessary to hang that thing out in front of your Mother?” There was just a little of an edge to my tone. “Why do you say that, is there something wrong with it?” He was being sarcastically immature. I was about to get defensive and lay the Mom thing on him. “Seriously Mom…I know that back home this would be considered all wrong, but next door, they say we are too hung up on nudity…that it is natural and we should not be ashamed of it. Don’t you agree? I mean…well, I saw you at the beach…uh, before and after you saw me.” I could feel my face flush, where was he going with this? “What do you mean…before?” I consciously wanted to avoid the incident involving my involuntary masturbation…and then getting caught. “Come on Ma, it was obvious to anyone you were trying to get those two guys attention. I mean really, you made sure they got an eyeful every time you moved”. “What are you talking about?” I was feigning ignorance. “Mom, you parked yourself right under the security cameras”. Oh shit…that is why the portion of the beach is almost empty. Mark continued, “tell you what, you have nothing to be ashamed about…you are one hot looking chick”. I could feel myself blush…apparently compliments work. “By the way, told you that you have nice tits!” Ugh…mental conflict spun in my head. All for compliments…but it is one thing to have my kid say I am a hot looking chick, but to actually point out sexual assets…never mind, stroked ego over decency every time. A “uhm…thanks” slipped out of my mouth. Not realizing I was staring directly at his penis dangling in front of me. He knew it, “Most of the people around here seem to keep themselves bare down there, like you,” so much for keeping the after out of this conversation “do you think I should shave it off?” God…what the hell does a Mother say? “It is up to you…” “Then why did you do it?” Am I really having this conversation with my son…who is standing just a couple of feet in front of me with a cock at least half again as big as his Father? “It is cleaner this way…and for appearances” Should have said something about appearance in my swimsuit or underwear…didn’t have a chance though. “Oh...you were planning on being nude…I must get it from you. Can I see?” I was just slightly flustered…not only from the audacity of his question, but the implication apparently was causing blood to rush to his extremity. I actually think he might be as large as my ex-lover… “Err…NO…for Christ’s sake, Get that thing away from your Mother”. Tried to sound authoritative with a hint of disgust…he saw right through it. “I’m going into the whirlpool…you can join me if you want” he said with slight laugh. “Don’t really think that would be right…but thanks for the offer.” I said in a very dilatory way. Took him twenty minutes to get the whirlpool up to temp before he climbed in…it did look relaxing and the swirling, bubbling water did cover him pretty much. Ah…what the heck, we don’t have one at home…I’ll wear my swimsuit…he is under the water. A glass of wine and relax. Mark had a shit eating grin when he saw me place my full wine glass in the cup holder. “Don’t get your hopes up kiddo…I am wearing my suit” I said jovially. Then I remembered that my Suit was sent down with the laundry and I would not get it back until the morning. Ah shit…”Mark…turn your head and do not look” I said with authority and meant it. I dropped my robe and started to climb in…Mark was looking the other way. At my totally nude reflection on the window! I slid into the water. “Damn Mom…you are even better up close!” “Don’t get any ideas, kid” even though a warm flush coursed through my body. Caught him checking our my tits every once in awhile but it did not bother me too much, could have been the wine taking affect or maybe I just did not care as our conversation went from banal to the event of the day. “You didn’t waste anytime meeting the neighbors did you?” this was precipitated by my curiosity and knew it would lead to where I wanted to go. “Nope, right after you left to sit on the beach, George from next door came over. Just to let you know…he was looking for you. Since you were already gone, he invited me over” Mark emphasized the “he was looking for you” part. “So I took him up on it” Mark was in story telling mood, as if he was discussing a camping trip, “When I told him I was only seventeen, but would be eighteen in a few days, he said that in this country sixteen is the magic number”. “What do you mean?” Was that the age of majority or just as far as sex goes? “Girls can get married at twelve with court permission, fifteen without. Guys at fourteen with court permission and at sixteen anything goes”. “So… was that woman?” my curiosity was pegged. A big smirk came across his face, “You mean Mary Anne?” “What do you mean? There was more than one?” had trouble controlling my emotion, my son is a frick’n slut? Not even contemplating the fact I was sitting with my naked kid with my naked body inches from his oversize dick. Ok…maybe I was aware of it. “Uh…yeah…but Mary Anne was the one I was with when you saw me”. “Who is she? Thought she looked a little old for you.” “Not really…she is only four or five years older than you”. If this was a compliment…it worked. Mark continued unfazed as to the shot of adrenaline that weaved from my glands to my bottom, “She is a school teacher from our state believe it or not…always dreamed about doing a teacher,” I think everyone has had that fantasy at one time or another; personally had a crush on my English teacher in High School…but our ages were much closer. Let’s see eighteen and forty-four or forty-five…I could feel my pores open up in my vagina at the thought. “Mary Anne had her boobs done awhile back and wanted an adventure before she got too old…guess I was or am part of it”. Damn…did that hit a spot of understanding! Not the boob part, but the last dance concept. Maybe I have a few years. “Is that it?” “Pretty much…unless you want the details” Apparently he wanted to go that route because he just continued not waiting for my response. He explained how as soon as he went next door, Mary Anne came and introduced herself as the one we both saw at the gate and asked about what the relationship was between him and me. Turned out that she also was on a similar vacation, she was there with her daughter, Crystal. Mark explained that he and I did not have that type of relationship. Apparently Mary Anne responded with a “too bad”. I wondered for a second if Mark was really repeating her or was expressing wishful thinking. After an initial flush feeling…I internally admonished myself for thinking that way. Mark continued as to how Mary Anne convinced him to “bare all”, which wasn’t too hard as once he looked around he knew he would not be embarrassed. But when he took his swimsuit off, she got all google eyed and after swiping his suit away from him she kind of embarrassed him by calling attention to his private parts in front of everyone. It dawned on Mary Anne at that point she had to make him comfortable. She took Mark to a slightly more private area, the area where the privacy cameras could be seen. He recognized me at the beach and pointed me out to her. Mary Anne told him that I was hot and if he had ever thought about he and I having sex. Unconsciously I leaned forward in anticipation of what his response was…don’t think he noticed, I didn’t myself. I wondered if my daughter and I would be this candid about this stuff…had to be a first for a Mom and son. He said that he mumbled an answer, whereas Mary Anne took that as a yes and instead of giving him a chance to refute her, she animatedly pointed to my actions as being in need of a good fucking. Based on the video. The whole time, Mary Anne was fondling his penis. “Mom, to be honest…watching you, listening to Mary Anne, her doing what she was doing to me…well, when Mary Anne stood up and sat on me…I could only hold out so long.” I wondered if he was implying that I had anything to do with his reaction. He continued. It had happened so quickly, Mary Anne did not have enough so she asked him if he had ever-felt fake boobs before and let him investigate with his hands, his mouth, and one thing led to another…they ended up out in the surf where I saw them. “Who were the other ones?” Not only my libido was stoked, so was my nefarious curiosity. “Only one…it was Denise”. He sounded like that was going to be it, but I was not going let it stop now. “So…explain Denise” I was adamant in getting a response. Mark hesitantly began; Mary Anne and he had gone back to festivities at the resort after their extracurricular activity in the water when Mary Anne was summoned to the office for a phone call. Mary Anne handed him off to Denise to complete the tour…Denise was interesting in that it was the first time he had actually been around a pregnant naked female. He said that even though she was showing pretty good, she told him that she was in her seventh month; she also had a very sexy aurora around her. Mark wondered out loud whether or not Denise not being much older than him, she was maybe in her mid-twenties and had a gorgeous face. Anyway, Denise told him that she was on her delayed honeymoon, patting her belly as if that was the condition needed for the honeymoon. Then she just flat told him she was going to have sex with him. He worried that he might hurt the baby…but Denise did something no other one had done to him. She went down on him. “Holy shit!” escaped from my mouth, the thought of almost eight inches of cock in my throat stunned me. No way she could take the whole thing. “Really Mom…took a few times…but she actually got the whole thing in her mouth. I…I could actually feel my…my cock in her throat. She put my hands on her neck so I could feel it going in and out!” Mark said excitedly…I moved my leg over one of his and accidentally rubbed his cock…I wanted to hesitate…shit, I wanted to feel it, see it…but, I did not. I wondered what it would feel like in my throat…and I have only given maybe ten or so blow jobs in my life. “Did you?” “Yep… could not hold back…right down her throat!” he was really excited about this. He said that Mary Anne never came back and Denise needed to do something so he started back here. Where he ran into Crystal, Mary Anne’s daughter. Even though he was naked…his suit disappeared, Crystal was fully clothed and just coming back from a sight seeing trip. This did not bother her at all. Mark’s tone changed…I surmised that Crystal made a different impression. He told me that Crystal was roughly his age and just had a fantastic personality. So why didn’t he pursue her I thought…was he worn out? In the next statement the reason became apparent, Crystal was at her time of the month and the resort does not allow the “Clothing optional” thing during that time. Then he announced that he told Crystal he would like to sight see too. Tomorrow they are going to the caves on the other side of the island. Good I thought, maybe I can take advantage of that…my vagina moistened at the thought, my brain switching back to horny mode. “So Mark, does a fake boob feel any different from a real one…of the same size?” It was a spontaneous question coming from the flash in my head of Mark talking about Mary Anne’s. Subconsciously I might have had an ulterior motive, but it was not dawning on me. “Uh?…uhm, don’t know…never really compared them”, but Mark’s eyes betrayed him, he focused on the top of my tits. I obliged and raised my chest out of the water. Knew full well this was wrong, but slid forward pulling Mark’s bent left leg between my spreading thighs while at the same time putting his hands on my tits. His jaw dropped and for a moment thought he was going to pull back. “They’re just tits Mark…what do you think…are they the same?” Can’t believe I was doing this, trying to even sound clinical. I wanted him to fondle, squeeze, twist,…hell I was ready to fucking rape him! He tentatively squeezed…then a bit more, the apprehensive look on his face turned to a more serious look…he was getting into it. My nipples yearned to be pulled…he did. I slid a little closer, Mark’s chin touched my cunt…a shock ran through my body making me jerk suddenly. My leg mashed against his balls and cock…sonofabitch…me being the bitch…in heat on top of that. I started reaching for that cock…completely ambivalent as to what I was about to do to my own son. Then the phone rang…the loud ring breaking through the fog of desire, the moment broken. Still I jumped out of the tub without a thought of humility…my naked body totally exposed to my son…I did not care. Until I picked up the phone and morality slammed me in the head. It was my husband, Mark’s father. I covered up with a towel as if there were eyes in the phone. The thought of getting caught by my husband with our son sent shivers through me. Mark on the other hand, had no vestige of humility, he climbed out, dried off, and throwing the towel in a corner then sat spread eagle in a chair facing me. That wondrous cock was in full display. My husband inquired into how our trip was going, if we had settled in. It dawned on me that Mark and I had only been here one day…seemed a lifetime ago, no that we had two different lives. Then he asked if Mark and I had anything exciting planned together. I lied and told him nothing yet instead of saying, “I was minutes away from fucking our son’s eyes out”. Then he asked to talk to Mark. When I handed the phone to Mark…he kind of blocked me in between the wall and the bed. I could not get around him unless I touched him. He saw that I was a little nervous about being that close…especially him being naked, me being naked under a towel, and his dad on the phone inches away. He was also expressing that smart-ass smirk as he listened to what ever his dad was saying. Knowing that I could not move without disrupting the conversation, I relaxed slightly. Mark caught that immediately and his had thrust under the towel grasping my left tit. To resist would have been futile and my surprised body jerk caused the towel to fall to the floor. He kneaded, then squeezed, slowly pulling towards my nipple. He turned to his right…his cock was right there…it was rigid. I fought the urge to grab it…did I want to push it away…or was I going to return the favor. I returned the favor…his body jerked in response to my mouth encapsulating the end of his dick. A head so big, it stretched my mouth. How in the hell did Denise get this monster all the way in? The thought that this was my son’s dick…coupled with the knowledge he was on the phone with his dad…the taboo of the whole situation overcame any thought of physical limitation. The end of his cock was now at the back of my mouth, my thorax slowly spreading as I pulled him further in. The body of his wonderful cock entered my larynx…moving down my throat. I had to breath, released just enough to let the air from my nostrils pass into my lungs, and then plunged that whole sausage deep into my throat. My lips buried into his pubic hairs. Ah ha! Had that fucking huge cock of my son entirely in my body! Morality be damned…it was mine. My senses were all encompassing around that huge dick in my mouth, but as if in a different room a I could hear one side of a conversation. “Yea dad…yea I know Mom is a hot looking woman” “Don’t worry…uh (he humped my throat), I’ll take care of her”. Mark held my head with one hand and thrust three or four times, his cock reaching the end of my throat on the pull back and then pushing deep into my throat. I have never deep throat ed anyone, at least not like this…but my hunger for his cock, over came any resistance. “Dad…I will give her what she needs…yea, yea…uhm” Mark froze and a hot string ejected from his cock almost straight into my stomach. I caught my breath in each stroke…more strings, all but one deep within me. The last emptied in my mouth, salty, thick, and yet creamy…only the second time in my life that I tasted semen after the first time when I told myself never again. Now I wanted more. That minute delay in the phone conversation apparently did not register to my husband as Mark finally broke his silence, “Yea sure dad…I’ll put her back on…she just had some cream, give a sec to swallow”. Then handed me the phone. It was short…he would not be able to make it at all and take care of Mark just like he asked Mark to take care of me. The first day of my vacation was almost over.
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