Win A Lottery, Lose A Lottery free porn video

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Ever wonder what winning the lottery might be like? Not just the paltry $1million dollar stuff but a really big Powerball hundreds of millions of dollars one. Well, I did and this is my story. I led a fairly normal life. At least for a practicing cross dresser with a bent for some submissive play now and again. I had visited many Mistresses in several dungeons in five or six states. The first session with each was always the best because of the unknown. What would this dominant do and how would it end? Would she quit when I safe worded out? Which I always did, of course. First, there was the legal aspect of the whole thing. Unless consent was present, she could be charged with all kinds of assault crimes. Then there was the financial side of the transaction. As soon as I used the safe word the session was over and she could keep her fee and go on to whatever she had planned for the rest of the day. The ultimate result was a not very fulfilling experience. So I would move on to the next opportunity. Winning the big one though made it possible to change all that. I chose to use a dungeon and a Mistress in England as they seem to be more prevalent over there and more inclined to include sexual pleasure in their sessions. Also, they appeared to be more aggressive. I travelled to London and began to set up the great adventure as I called it to myself. First a visit to a banker where I made some arrangements. This banker was also a member of a B & D club I had met on the internet and was not surprised when I explained everything that I wanted to happen. I placed a large sum of English Pounds on deposit and signed a contract that instructed him to withdraw a set sum of $2,000 pounds once each day and place it in a safe deposit box. As a bank officer he could do that. The contract specified that under no circumstances was the process to vary. There was enough money in the account to do this every day for five days. One deposit each day, no more, no less. At the end, when the account went empty on the last day (and only if the terms of the contract had been faithfully fulfilled, a sum of $5,000 pounds would be wire transferred to the banker's personal account for a job well done. Any deviation and he would get nothing. Next I selected a Mistress from the on-line ads that are so prevalent in England. I offered her twice her usual fee if she would meet with me somewhere public and remain anonymous. She did and when we met I asked her to refer me to another Mistress who had a dungeon. I was not to know the name of this Mistress nor the location of her facility. She agreed to discuss the request with someone she knew, especially after I upped her fee and paid her in cash. Once the cutout made the referral, I met the second Mistress at a coffee shop and found her to be lovely. With her I made another, somewhat less legal and actually unenforceable (at least in court) contract. She was to take me as a slave for five days and use me as her slave slut for the whole time. To insure she kept her end of the deal, she would only be paid when she completed certain conditions. I was never to know who she was and the location of her dungeon was to remain a secret. Each morning of the slave term she would deliver a set of videos to the banker. After he verified they contained the material I had specified earlier, he would allow the woman to open the safe deposit box, put the disks in the box and take the package of money out. When she left, he would retrieve the disks and put them in the mail to a P. O. Box in the USA. Thus the only way they could both get paid was to follow the terms of the agreement. At the end of five days, if all went as agreed a separate bonus, a very large bonus would be wired into a different account for the Mistress. To earn all this largess, the Mistress was to keep me in good health and bondage for five full days. I had made a long list of suggested possible scenes that might be played out and given a copy to her and to the banker. Each day she was to drop off the videos of one scene. Also, she had to drop off another video that ran for at least an hour and showed someone masturbating me and keeping me in a state of unfilled desire for at least an hour. For the trouble of keeping me fed and my other bodily needs met and to hire whatever help she needed, she received an advance against expenses of $2,000 pounds. Finally, I destroyed all of my identification. My passport, credit cards, licenses, everything went up in smoke. I did not know anyone in the country and I had no way to prove who I was or to access any of my wealth. No matter what happened, I could not buy my way out of the experience just because I decided I wanted to quit. Promptly at the appointed hour I presented myself at the coffee house again. The Mistress was not there. After waiting for a while I got up to leave. A van pulled up in front of the shop and a door slid open. I was ordered to get in by someone I had never seen and who was wearing a full body catsuit and a mask. Once in the van the door closed. The whole pickup took only a few seconds and I knew no one had even noticed. I was handcuffed and quickly blindfolded and placed in a seat with a seatbelt to hold me in place. I was driven around for quite a while, obviously with many turns to confuse me and to make sure I was not being followed before I was taken to the location where I was to meet the Mistress. I did not know this until later, but it was a large warehouse style building, well insulated and in an area where manufacturing noise was fairly commonplace. What little noise might come from the building would never be noticed by anyone outside. Inside the building were several areas. One was a dungeon area with numerous subsections for specialized scenes. Another was a sumptuous living area for several people. A third was a large fairly open area that was designated as a group party and play area. The Mistress introduced herself only as Mistress S and she showed me around and then we went over the agreements I had drawn up. She studied them for a while and then observed that once this started it would not end until the five days were up. There was no way she could end the session without losing a great deal of money and there was no way for me to buy my way out early. This was to be an all or nothing adventure. I explained that was the way I wanted it. My only way out was to endure until the five days were up, no matter how much I wanted to quit. The only limitation was no physical damage. I had a certificate from a local doctor stating that I was in good health with no problems. If that changed, she would be liable for whatever she had done. Her smile was a little evil as she invited me back into the dungeon part of the building and turned me over to two lovely women in typical maid slave attire. Black short skirts, petticoats, impossible heels, exotic makeup. Both were well endowed but it was soon clear one was male and one was female. Husband and wife I eventually discovered. Habitu?s of what they called the London House of Pain and Pleasure Society with a grin. It was obvious they were making this up as they went along. Later it also became obvious they were devoted to Mistress S. They were instructed to prepare me for an afternoon prefunction and then for the evening's mainstage show at 9:00PM. I was taken to a large bathroom and told to remove my clothes. I had to place them (along with the hidden ID I had sewed into them) in an incinerator with my own hands, turn on the burner and watch my only safety valve go up in smoke. What followed was a series of sensual massages, baths, rubs, hair removal treatments and a lot pampering. I was feeling very luxuriously relaxed when things changed. The two maids covered my entire body with a coating of powder and then left. They were replaced by two leather clad domes each wielding whips and canes and no shortage of various bondage equipment. The experience was about to start for real. I was told to put on a red latex bondage suit that one of them tossed at me. It was tight and only possible to don because of all the powder that covered my now hairless body. I stepped into the feet and began to draw the suit up my hairless, smooth body. When I got to my crotch I discovered that part of it was open and my private parts stuck out uncovered. The suit also left my rear cheeks open and uncovered. It then went up my chest where my arms went into coverings that reached all the way to my fingers. Two openings over my nipples left them peeking through. One of the dommes fastened up the rear of the suit. It was just a long Velcro fastener but it went from waist to neck. It held firm as the suit was stretched tightly to surround my body like a second skin. A head piece hung down in front at the neck and this was soon pulled up over my head and smoothed into place. This too had Velcro down the back that pulled it skin tight. It had openings in the front for eyes, ears, nose and mouth. Matching leather cuffs were fastened to each wrist and then hooked together. A steel cable was lowered from the ceiling and a hook locked onto rings on the cuffs. I heard Mistress S as she told them to "take her up and we'll get started." The cable started to wind up back on the overhead winch. As it wound, my arms were pulled up above my head until my heels just began to lift from the floor. I was shown the leather arm binder that was then wrapped around my arms. It reached from wrists to shoulders and my head was pulled forward so when my arms were cinched they would be behind my head. Together the two dommes worked to lace the binder closed until my arms were locked together from elbow to wrist. When I started to complain that it was too tight, a pair of clamps were thrust into my mouth and forced open. This stretched my jaw until I thought it might snap. Then a rubber covered ring was inserted behind my teeth. When the clamp was removed, the pressure of my jaws held the ring tightly in place. A moderate sized hollow dildo slid through the ring and into my mouth reaching back until it just tickled my throat. It had a padded base that passed over my mouth and a strap that went behind my head and fastened it into place. I could breath and make grunting noises or even screams but words were impossible. The corset came next. They seemed to take unusual delight in showing it off to me. It was a bustier style with large cups. It was covered in satin but was obviously of some kind of strong material with many steel curved stays that made it hour glass shaped even before it was laced closed. It went around my body and the clasps in the front were fastened to hold it in place. "Take your last deep breath," I was ordered. "For the next few days you are going to be gasping for each shallow breath and probably fainting at every major exertion. Most slaves learn to hate this particular corset after just a few minutes. It will part of you continuously for five days." I heard the two dommes talking as they started on the laces in the back. They were going to lace me down six inches, two more than the normal even for punishment. Since I would be losing weight during the coming ordeal, they would tighten it each day. They figured I would be down to between eighteen and twenty inches by the time I was finally released. They were right. By the time they tied off the laces I could only take very shallow breaths and I already wanted the thing off. But it wasn't coming off. Not for five very long days. They seemed to enjoy showing me the things they were using on me before they applied them. Explaining how they worked and how much I would come to hate them and why. They held a pair of what looked like silicon breasts up in front of me. They were perfectly shaped but seemed to be pretty heavy. I soon found out they weighted about five pounds each. The dommes sprayed one with surgical glue and then a clip on the end of a spring was pulled out of the center at the back. The clip was fastened to one of my nipples and the breast was placed in the cup of the bustier and pulled back against my chest. The spring pulled the clip tight and the weight of the whole thing seemed to hang from my nipple. I gagged and groaned from the pain but to no avail. They simply laughed and then attached the second breast. I could only endure as the unaccustomed weight pulled on my nipples. The breasts moved every time I moved and that only made the pain worse. "Nice tits," I heard Mistress S observe. "Nice curves too. I'll bet the club members will just love this tender little morsel. Besides what she is paying us, we'll make a fortune off of her. Too bad she can't just disappear completely. I'll be we could sell her for a pretty penny." Now I was really scared. This was all just part of the scene, surely. Wasn't it? It had to be. A sawhorse was placed in front of me and one leg was lifted up and brought to rest on the top of the horse. Again, I had to watch as a patent leather ballet boot was forced on my foot, bending my foot into an impossible arch. As I watched the laces being tightened and then tied off I knew I could never remove that thing myself. By the time the second boot had joined the first I had a new agony to worry about. Now I was balanced on my tip toes, trying to stand and take the strain off my arms and to stay conscious as I gasped for each meager breath of air. But they were not yet finished. One of them grabbed my balls and stretched them as far from my body as she could. The other then began wrapping them tightly with a thin rubber strip. She started at the base of my cock and wrapped all the way to the taught end of the ball sack, over and over, tighter and tighter until it looked like a giant red lollypop on a black stick. Small white pills were dropped into my hollow gag followed by a liberal glass of water. I soon discovered that Viagra was to become a part of my daily diet. Enough to keep me hard at the slightest touch. Enough to keep me hard even through the pain I was experiencing. Especially since I was reminded about the second part of the contract and then told that they would enforce it in spades except that I would not be allowed to cum. Not once. Not ever. The photographs being taken told me all. This was scene one, the first day and I already wanted out. What happened next was a taste of the hell he had let himself in for. He was left alone. On the wall in front of him was a full length mirror. Next to it was a large clock. For two hours he stared at himself in his feminized regalia. He watched as the clock slowly ticked off the minutes. His pain from standing in the bizarre boots and hanging from his bound wrists just kept growing. His jaw ached from being forced to remain open. His waist felt as if he was being cut in half by the corset. The only sounds he heard were those he made as he groaned and gagged and slowly moved the little his body was allowed by the tight bondage. He also saw his crotch where his tightly wrapped balls were screaming in agony and his cock grew to the longest and hardest he had ever seen it. For two hours the torment went on. Then they came for him. Two of the most gorgeous women he had ever seen. Both minimally dressed in scanties that had to come from Victoria's secret. They lowered the cable that held him up and together they placed him on a padded table. Straps went across his body in several places and fastened him tightly to the table. That was when he realized there was also a mirror on the ceiling. He could clearly see himself and the two women as they moved about the room. He watched as they poured something from a bottle onto their hands. Hands that soon wrapped themselves around his raging cock and began to masturbate him. They actually giggled as they worked him into a frenzy. His hips strained to move up and down but it was hopeless. Each time he neared a climax one of them would squeeze or strike his balls and bring him back down. Also, the effort to move and to get himself off would send his respiration up and he would be gasping for breath he could not get. As his blood oxygen was depleted his body tried harder and harder to force air into his lungs but the corset did not give. It was not long before he felt things going black and he passed out. The torment went on and on. They would stop and awaken him with smelling salts and then begin again. Finally an alarm went off. The two women simply got up and walked out of the room. He heard them talking about how much they had been paid for just an hour's work and how they could hardly wait until tomorrow for a repeat performance. The lights went out and he was left alone. After a while he did manage to blank out the pain and doze off. He woke up when the lights snapped back on. He did not know how long he had been lying on the table but once his eyes adjusted he could see Mistress S staring down at him. "Well, it all worked out nicely," she said. "That was just a test run of course but it will count as one scene and one pleasure session. Our pleasure, of course, not yours. The computer disks were delivered, approved and the money changed hands, just like we agreed. My friends will prepare you now for your second day and second session. I have decided that we will add a few of my favorite sessions to your play list and then we will just choose a total of five. You won't know which five but, of course, once a session starts you will recognize it and know how it is going to end. That should add to the drama of it all." She left and the two maids returned to the room. I felt them attaching various tubes to me. They slipped a catheter into my penis and soon I felt my bladder filling up with a cool liquid. Once full it was allowed to drain, then refilled and drained again. A hard nozzle was greased and inserted up my anus and I was given an enema. Again, it was a cool, soothing liquid and again it was done twice. Finally, some kind of tasteless stuff was pumped into my wide open mouth and down my throat. At the end, I realized I had been fed, cleaned out inside and was now ready for whatever was about to happen. The maids left and two nurses came into the room. They unstrapped me from the table and allowed the winch to pull me back up to a standing position. The first thing they did was tighten the laces on my corset until I was once again gasping for each breath. I could watch in the mirror on the wall as they hung rubber bags from stands next to me and ran tubes down to my catheter and to a very large dildo which was soon lodged far up my ass and strapped into place. The last tube ran from my gag opening to a bowl placed in front of me about waist high. I was left to stand there for a couple of hours while the corset and boots worked to cause my muscles to tighten up and begin to cramp. Several people came into the room and began to examine me. They also seemed to be in a party mood and were soon drinking and snacking. Mistress S approached and told me what was about to happen. The bowl in front of me was actually for the guests to use. When it contained a liquid it would be heavier and it would hang slightly lower. That would trip a switch which would open the valves on the two bags next to me. The would also slowly rise until they were far above my head. The bags contained a total of three quarts of hot, soapy, highly spiced liquid which would soon be inside of me. The longer it stayed, the hotter it would seem to get and I would soon be suffering unendurable cramps. The only way to relieve the pain would be to suck on the tube in my mouth and drain the bowl. When it was empty it would rise up and that would lower the two bags and allow me to drain. The party was to last well into the evening and I stared in shock as the first guest stepped up to the bowl, took out his penis and began to relieve himself into the bowl. I watched in silent horror as the bowl began to fill and then I heard the audible click as it tripped a switch. Slowly the two liquid filled bags began to rise. As they went higher and higher the flow up into my bladder and bowel came faster and faster. Soon I was full of hot, soapy water that was burning my insides from the spices. I stood the pain as long as I could but finally the cramps started and it was too much. I had to have relief. In disgust, I sucked on the tube in my mouth and managed to drain the bowl of piss and swallow all of it. I stood in painful relief for a few minutes but then another guest stepped up to relieve himself. Between the hot, spicy fluids and the terrible cramps I experienced, I soon became very good at sucking up piss which I, of course, had to swallow. Of course, it was all voluntary. After all, nobody was actually forcing me to drink the urine. It was a very long night. When the party finally ended, I was drained for the last time, lowered to the padded bed and again strapped down. The two beautiful women returned, this time in exquisite evening gowns, complete with long white gloves and went to work on my Viagra stiffened member again. Once more I was brought over and over to the edge of completion until my hour of denial was completed. As much as I wanted and needed to ejaculate I was actually listening frantically for the alarm to go off. Before they left, they gave me a sleeping pill and I was soon oblivious to the passage of time. Two scenes down and three to go. My body ached from the enforced mummy style bondage and my cock was now constantly erect. My stretched balls ached with the need to ejaculate. How would I survive the next three days? Well, I did. Obviously or you would not be reading this. Maybe someday I'll tell you all about what happened but for now, let's just say that for the next three scenes, I learned how to suck a huge, black cock and to give very good deep throat. I also learned what cum tastes like when you suck it out of a hot pussy after watching some guy deposit it in there. I also learned just how women must have felt having to be corseted all the time. Over and over the laces were tightened and my waist continued to shrink. Finally, I learned how bad it could get when the one thing you want most in the world, to cum, is denied to you, time and time again. Yes, I certainly got my money's worth. And then the last scene played out. The two maids had come and gone. They had completed his ablutions and he was once again fed, watered and cleaned out. This time they had raised his arms up again until he was standing vertical on his tip toes but then they had placed a large wooden wall like structure behind him. It was well braced and fastened to the floor. He stood against it. Two obvious dommes came in and began to strap him to the wall. Heavy leather straps went across his upraised arms at various places. Two went around his chest above and below his protruding false bosom. One went around his head pulling it back and tight against his arms so he could only look straight ahead. Once again he could see himself in the wall mirror. Cuffs were fastened around each leg just above the knee. Together they raised his legs up and used chains to fasten his legs back to the wall on either side of his head. He could move his lower legs but that was the only part of his body that would move. The position caused him to feel like the corset was cutting him in half. "Don't you just love the way the lights make those pretty patent leather boots shimmer and sparkle when he moves them?" one dome asked the other. "I sure do," the other replied. "It's so exciting and stimulating. I'll bet our clients will find them that way too." Mistress S entered the room and walked up to him. She stood between his legs smiling at him. "Scene five," she said. "This is where you really earn your keep. You see, I have been running special ads ever since you arrived. I have sold your pretty ass to quite a list of people who are all anxious to meet you. Very anxious. You might say they can hardly wait become intimately acquainted with you. You on the other hand will just have to hang there and watch as they do you. Of course, wrapping your legs around them and gasping in pleasure will probably encourage them to finish their engagement with you more quickly. And the flashing of your heels will only help excite the next client in line." She turned away and walked to the door, taking the two dommes with her. "Have fun my little, helpless, sexy sissy. We'll be back in the morning to release you, after we collect our final payments from the bank plus our bonuses. " He tried to plead for release but he was ignored of course. His struggles were only minimal and consisted of waving his legs around as a line of men came through the door and formed up in front of him. The first one stepped up, leaned close and began to kiss him. As he was forced to accept the thrusting tongue into his wide open mouth he felt the hard tip of an erection pressing against his other opening. He fought it for three men. After that he found himself thrusting back with his own tongue and wrapping his legs around the hard body pressed up against his crotch. He would do anything to increase the guy's pleasure and to reach the moment of relief when the cock exploded and shot yet another load of cum up into his insides. He knew the video would look like he was in ecstasy, enjoying every thrust as he was taken. Nothing could be more humiliating he thought as the next man stepped up. And the next. And the next. How wrong he was. Mistress S returned for her last visit. He was lying on his back, strapped to the padded table. She told him the videos had all been delivered and all the payments had been made. His fantasy five days as a slave was finally over. He was about to be freed. Well, at least sort of. It seems there was to be a process. As a special bonus he would be treated to a two hour session as two vixens would lavish their talents upon him. They would soon have him begging for release. The only thing different was that this was not going to take place here in her dungeon. She then placed a rag over his mouth and nose and he was soon unconscious. When I awoke I was still strapped to a table but now it was in a large party room and there were lots of people around. Some were watching and some were involved in various bondage scenes. I realized I was at a place I had seen before, The London Power Exchange. It was a consensual bondage and swap club. Two lovely ladies I had never seen before stood beside me, one on each side. They were each dressed in sexy lingerie and were apparently bondage slaves. Someone gave them orders to get started and they did. For two hours I writhed and moaned and begged and pleaded as they did just about everything one could do to a hardened cock except let it cum. Then a very large, gross dirty woman was helped to straddle me. I could see her fat bounce up and down as she rode my stiffened pole. Her breasts bobbed around like a couple of bags of loose laundry and she drove herself to orgasm after orgasm. Surely I would never react to this disgusting sight, but in the end, I came, screaming every second as each painful spurt made its way down my tightly wrapped cock and balls. I was then turned over and used orally and anally by several of the members before I was finally unbound and released. I soon found myself alone on a dark London street, looking and smelling like a well used lady of the night. I finally staggered up the steps of a local police station and managed to convince the night duty officer that I really was an American off on a fling that had gotten out of hand. Most of a day later, after a fingerprint and DNA check at the US consulate, I had my identity back. I never told anyone the entire story since none of them would believe it anyway. They left me in my hotel room, alone, as I took a few days to recover. As I was getting ready to check out and catch a plane for home, the phone rang. At the same time there was a knock at the door. I answered the phone and I recognized the voice immediately. "Get the door," it ordered. I did and was handed a large shopping bag. Chills went up and down my spine as the contents spilled out of the bag onto the floor. Black stiletto platform heels, fishnet stockings, a steel braced corset, low cut peasant blouse and leather mini-skirt along with a blonde wig and lots of garish makeup. She wished me a happy trip home and said that we would have to do this again sometime, maybe in Wichita. She said she would have someone at the airport and if I showed up in anything other than the outfit she had sent over, copies of the tapes she had made would be on Facebook before my plane landed. I hung up the phone, frightened and denying everything. How did she know who I was and where I lived. And why was my cock hard as an iron bar? And why was I lacing a corset tightly around my still tiny waist?

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This is a long story and it is also my first, please be gentle!! I originally wanted to do this with images, but it proved too hard (anyone with help or images they feel suitable please email) normal stuff applies if you are under 18, of a nervous disposition or don't like bondage/tg etc (why are you here!) don't read. Please give feedback (except spelling, grammar mistakes - life's too short!!!) Denver I love your stories please write more soon. On with the...

2 years ago
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Lottery winner part 1

20-5-69-3-2-32-14-17 I had used these numbers every week to play the local lottery for the last three years. Sunday afternoon I was in my usual place, curled up on the couch with a book. The TV droning on in the background. Casually I looked at my toes and noticed that I had smudged the freshly applied polish, damn. Then I saw that the numbers were being pulled...20, 5, 69, 3, holy cow I have never gotten four numbers before..2, 32, my heart began to race, 14 oh my, 150 million dollars...

2 years ago
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Lottery WinnerChapter 5

“Okay.” We left in my car. I took her to a nice steak house. Tuesday was a quiet night for them and we were early enough to be in front of any rush. I told our server that we were in no hurry and would appreciate time between our courses since we had much to talk about. We ordered glasses of Merlot and salads finding that we both liked blue cheese dressing. When that was served, we were talking about Beth’s day. She said, “You are all the buzz. People already miss you. I know Cindy does.”...

4 years ago
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Win or Lose PT 2 Creampie Eating

It had been over a year since Janice made her bet with me that I couldn't last long enough to make her cum before I blew my load in her pussy. I lost twice the first night, and I lost every time since then, but I still held out hope that I could win. My prize? If I win my wife will, for the first time ever in our relationship, willingly suck me to completion and swallow my cum. My penalty? If I cum first, I have to go down on her and get her off with my tongue. In the process I end up eating...

3 years ago
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The Lottery

At South Bay University tuition is free. It is a haven for low income students and families who otherwise might not be able to send their children to a 4 year school. The reason they can afford this is their lottery. The lottery is a drawing where one student’s name is picked and for the remainder of their schooling they are to remain completely naked even when on weekends or break. The university thoroughly documents the naked student’s life and studies through both picture and video and...

4 years ago
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The Lottery

Frank Albert, the man with two first names, stared at his lottery ticket with disbelief. Naturally he was overjoyed, but part of him was also disappointed he didn’t win the money earlier. $700 million dollars. He could have used that when he was a young man, but he was still a virile 70 year old man and had some time to spend it well. There were lots of things he’d like to do, and now was finally his chance. There was a list of vacations to run through. One week later, he’s on the news having...

BDSM
4 years ago
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Company Lottery

I work at an office in the mail room. I'm so much more than the mail person; if someone has a problem, they call me. I help people get their car started or give them a ride home. If they need something opened or need office supplies but do not have time to get them, I’m the man for the job. You work as an executive in the office. No one would care if you showed up at work or not. You work alone and are very antisocial. You even tell me to drop off the mail and get out. Even after you treated...

Office Sex
4 years ago
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The Lottery

The lottery Earth is an a petri dish for hyper intelligent beings, one day they send down a machine, we call it the lottery, it transforms nearly every person on the planet, swapping characteristics, both physical and psychological. What are the odds you get something... normal? Alex walked along the path through Eastwick Park, the dirt line, cut into the patchy grass by thousands of other people looking to shave a little time from their commute, joined Front street west and Harris...

2 years ago
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The Lottery

“If you won the lottery, would you still want me, Sylvia?” She was leaning against me, after just coming back out of the house. She went in to go to the bathroom and grab us some water. Both of us were tired after mowing and cleaning up the yard. It was really hot out. “Of course, sweetie. I saved an angel, and an angel saved me. I wouldn’t trade my angel for all the money in the world. I might buy her a ring and ask her to marry me, but I doubt she would say yes. She’s so young and pretty and...

2 years ago
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I Won the Lottery but

It all started when I won the lottery. A 350-million-dollar- jackpot. After taxes, and with a lump sum payout, I had 210 million dollars. It should have been the happiest moment of my life. Instead, I curse that day, every single miserable day of my existence. The first thing out the gate, my loving wife of nearly 20 years, immediately files for divorce. Between the shyster lawyers, on both sides and her, they hit me for 125 million dollars, plus she kept the house in the suburbs. Next, my...

2 years ago
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Lottery WinnerChapter 3

Helen was there as were five or six guys and Mark. Helen was sucking a cock and her cunt and ass were both leaking cum. She had been thoroughly gang banged. I shook my head and went up the stairs to my bed. I closed the door. It was very late when the sounds of fucking quit and didn’t start again. In the morning, I rose and went into the kitchen. The living room had been cleaned up and no one was to be seen. Mark came down shortly looking tired. He said, “It got a little out of hand last...

2 years ago
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Win or LoseChapter 2

It had been over a year since Janice made her bet with me that I couldn't last long enough to make her cum before I blew my load in her pussy. I lost twice the first night, and I lost every time since then, but I still held out hope that I could win. My prize? If I win my wife will, for the first time ever in our relationship, willingly suck me to completion and swallow my cum. My penalty? If I cum first, I have to go down on her and get her off with my tongue. In the process I end up eating...

2 years ago
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I Won the Lottery

Foreword Normally, I write it, read it, fix the obvious screw ups, and then post it. This time was a little different. Ok, a lot different. I had an offer to edit my story and I’d like to thank a great lady for taking the time to do that for me. She is a writer here at Lit and her name is Alexis Haines. She did her best to correct my punctuation and grammar, which is a full time job. I took most of her advice, so any screw-ups should still be attributed to me. She also took interest enough to...

3 years ago
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I Won The Lottery Ch 01

My name is Jim, James Hoggard, actually. I drive by the local university every morning on my way to work. Often there is heavy traffic and I catch many of the stoplights. I spent my time watching the female coeds. All shapes and sizes, some pretty, some not. Listening to the news on the economy I knew that many of those students were going into debt up to their eyeballs to have a chance at a good life. Being an intense lover of the opposite sex, and having a vivid imagination, I have always...

4 years ago
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Gender Lottery

It has been close to a hundred years since the last female was born. Nearly fifty years since they started being made. The Gender Lottery has been in place for the last thirty five years. Its still a mystery as to why girls stopped being born. One day the world was as it was before, the next day only baby boys were being born from the female womb. This was a hard thing for many to accept, and many at first believed this would be the end of humanity since males couldnt reproduce with one...

2 years ago
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Like Winning A Lottery

Like Winning A Lottery By: Londebaaz ChohanThere was absolutely, positively no doubt that I was bisexual with strong sexual urges for both sexes. By the age of 23, I had lived with two women but both times; the relationship could not evolve into a flaring long term love because the need for gay sex took over me and the hetero relation had to end. All this aside; I also realized that it was not any easier to be known as gay or bisexual and I only had all gay episodes as one-night stand’s sexual...

3 years ago
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A Mothers Lottery Win

A Mother's Lottery Win By Julia Thomas Chapter 1 My mother and father had got divorced and we were living in a small village just south of Birmingham in the UK. I am 10 years old and my name is Andrew Carter. Since the divorce I had not seen my father because he had run off with another woman and had taken everything and left my mother totally penniless. My mother had continually tried to get a job to no avail. We both have lived in the house for some twelve months. I...

3 years ago
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I won the lottery

Life Goes On Introduction: So the girl's a little older than I might have otherwise had in, but one has to observe the house preferences' As always, comments and a vote are always appreciated. So after 35 years of marriage, my wife decided she’d had enough (of what, she never did say) and one sunny day announced she’s going to go live with her sister. She wanted a divorce and half of my retirement. We went through several months of this and that legal crap and a few arguments over some...

1 year ago
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The Lottery

The Lottery By: Melody Anne, aka Malissa Madison Sitting on the large wooden deck overlooking the Lake in the early Spring morning, a cup of Hazelnut Coffee on the glass top patio table she thought back over her past. She'd always been a troubled child. Always in trouble for one reason or another. Not because she was bad, but because she liked Dolls, and dresses and high heels, and anything else that society felt were reserved for little girls. Yes, she always knew in her...

3 years ago
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Lottery winning toilet

A few nights ago Greg’s life had ch anged forever. His numbers had come up on the lottery and he’d won ?56 million. Needless to say that’s the kind of money that can change lives and allow people to experience their wildest fantasies. After telling his boss what to do with his job Greg set his mind to a fantasy that had been growing within him. It had started when he was much younger. Something about guy’s arses thrilled him like nothing else. Before long arranging meets through websites for...

2 years ago
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Lottery winner part 2 homecoming

As the Laura Ashley prairie dress settled over my pantyhose covered thighs, falling to mid-calf I caught myself loving the feel of it. It was periwinkle with an adorable lace scalloped collar and empire waist, I had always loved the way a full skirt on such a dress would flow around my legs and now I was wearing a beautiful one. I slid my feet into the little white flats luxuriating in the feeling of my nylon covered toes wiggling in the feminine shoes. Looking in the closet again I...

3 years ago
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Lottery Winner part 3 new feelings

Go have your privacy. Don't worry tonight we only sleep." While ominous I understood the implication and stood up, then bent over put my hands on his face "Thank you for this adventure," I said and kissed him on the lips. A few months ago I won a significant lottery that was now giving me the chance to live out my fantasy of becoming a woman and a wife overnight. As I woke up I became aware of his body pressed up against mine in the bed. Reflecting on the night prior I was amazed at...

3 years ago
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Lottery winner 4 love and trials

Johnson smirked and said to Jeffery "if he had put the towel on like a woman I would not have been forced to do this but as you can see he didn't and now he will have no choice or be forced to be indecent. Remember he asked for his feminization. He truly is a strange man." He never saw it coming. Standing over Johnson, after slapping him so hard he fell to the floor, my wonderful man told him "She is a woman. One day she may have opted for implants, but this way was wrong. She is...

2 years ago
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A lucky day playing the lottery

I stopped at the local deli this morning to get an egg sandwich and a coffee. When I walked into the store the first thing that caught my eye was the fiftysh blond BBW going over scratch off tickets in the corner. I quickly checked her out, trying to be discrete,  I could tell that she was curvy and had big tits. I went and placed my order and went to pay at the register. While waiting for my order, the BBW came up to the lottery station (next to the register) and handed over a couple of...

Oral Sex
4 years ago
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Zak and Lanny The Lottery Part 3

“Good morning. You two look pretty together.”“Hello, Olga. I love your skirt, and I see more of your beautiful legs,” said Lanny.“Zak, I want to share a fantasy of mine. I want to see the two of you sucking another guy off. I have a fixation of seeing cum squirting out the tip of a hard dick and into an eager awaiting mouth.”“Well, it sounds interesting, and I think Lanny and I are up to the job. We both love the taste of cum, especially when it is warm. There is one problem, where will we find...

Gay Male
3 years ago
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Lottery WinnerChapter 2

I took Beth to a Mexican restaurant that was good for business lunches. Both of us had iced tea and no alcohol. We ordered and the server left. Beth reached over the table and took my hand... “X, I was a bit forward in your cubical earlier. I just had to get your attention. Doing that both embarrassed and aroused me. I wasn’t going to let this opportunity get away. Thanks for inviting me to lunch.” She smiled at me. She was a very pretty girl or woman. I figured she was about my age and a...

2 years ago
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Lottery WinnerChapter 38

In the morning, we woke up and had coffee and a light breakfast. After cleaning up, we were ready for our limo. Our tour guide this morning was a young man just, seemingly, younger than I while our driver was a young woman who looked to me n her mid twenties. Both were wearing dark blue jump suits. Hers was unzipped enough to show cleavage while his showed a reasonable chest with a light coating of hair. His hair was light while her hair was dark brown. Both were taller than average. With...

1 year ago
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The LotteryChapter 17

Sally woke up to the music that came from her clock radio. She sat up and pushed the button that silenced the alarm. "I'm fifteen today!" She thought to herself. Sally got out of bed and walked into her bathroom, pulling her tee shirt over her head. She stood in front of the mirror and stared at her reflection. She studied her firm breasts, still tan from the days spent topless in the sun. She smiled to herself, remembering the fun she and her cousins' had being naughty. The young girl...

3 years ago
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The LotteryChapter 41

Thursday arrived and Tom woke up excited about going to the photography workshop with Lisa for the weekend. He had packed his things the night before and had his suitcase ready to go, along with his camera equipment. He went to his sister's room and woke her up. "Good morning Sally, time to get up for school." Sally rolled onto her side and looked up at her brother. He was standing next to her bed in his boxers and a tee shirt. Slowly, she swung her legs over the side of the bed and sat...

3 years ago
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LotteryChapter 3

Again I went to my apartment and watched television for the rest of the night. And I slept a restless sleep while having images of my cock growing so large that it overwhelmed me. The business trip was boring, the days long with meetings and lectures. I did learn a few tricks about ways to handle my money but I had to shift through the shit to do it. Karen looked and acted very professional, I kept her busy being my personal assistant. She sat through all the meetings with me, and also...

1 year ago
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The Lottery

I won the lottery. Really big....over 300 million dollars paid out over the next 25 years. In my late twenties and now filthy rich. What to do? What to do? After I won, I did all the things that you are supposed to do: traveled, bought a nice house, not too big but certainly big enough, and pampered myself with all the gadgets and everything else to fill out my home. One of the things I pampered myself with was Sarah. She, I hired away from a local massage parlor as a live in maid/house girl,...

Erotic
2 years ago
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Win or Lose Creampie Eating

I guess it’s a case of “be careful what you wish for” but I’m not really complaining, since what I wished for, ultimately, was a better sex life. I certainly got that, but it wasn’t exactly what I thought it would be when I was wishing for it. My wife, Lily, and I have been married for a long time and during all our years together she’s never, willingly swallowed my cum. I’ve gotten lots of blowjobs, but she’s always pulled away at the last instant and finished me off by hand. At one point,...

2 years ago
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Win or Lose

[Authors note: This story has a dual ending. You can read through the whole story, pick your preference or if you’re feeling adventurous, grab a quarter and play along. Each outcome starts at either “*** I Won!” or “*** I Lost!”. Enjoy.] My wife has the most incredible ass. Firm, round, with just enough padding to make it wiggle when she walks but splays open enough to show me her tight little pucker when she’s bent over. I’ve been trying to slip my cock in that entrance since our honeymoon....

2 years ago
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Win or Lose

[Authors note: This story has a dual ending. You can read through the whole story, pick your preference or if you’re feeling adventurous, grab a quarter and play along. Each outcome starts at either “*** I Won!” or “*** I Lost!”. Enjoy.] My wife has the most incredible ass. Firm, round, with just enough padding to make it wiggle when she walks but splays open enough to show me her tight little pucker when she’s bent over. I’ve been trying to slip my cock in that entrance since our honeymoon....

1 year ago
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Win or Lose

[Authors note: This story has a dual ending. You can read through the whole story, pick your preference or if you’re feeling adventurous, grab a quarter and play along. Each outcome starts at either “*** I Won!” or “*** I Lost!”. Enjoy.]My wife has the most incredible ass. Firm, round, with just enough padding to make it wiggle when she walks but splays open enough to show me her tight little pucker when she’s bent over. I’ve been trying to slip my cock in that entrance since our honeymoon. She...

2 years ago
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Win Some Lose Some

It never fails to make me angry. Men from the US come over here and think just because they have money, they can take what they want from our culture and go away happy. Well I have a surprise for them My family has been in the slave trade for years now and I have not wanted any part of it. Our women here in the Orient are undervalued and sometimes sold off by their families to our family to do with them as we please. Many go into factories where they produce products for Americans and...

3 years ago
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Ashwini Aunty Ki Chudai

My sexy married Ashwini aunty age 35 Gori Sexy thi uski size 34 30 36 thi…Dikhne mai hot hone k karan mai us ko har roj dekhta tha us ko dekh k mera lund khada ho jata tha kyu ki us ki matak ti chaal aur uski sexy figure dekh k mujhse control nahi hota tha. Roj sochta tha ek baar ise chodne ka mouka mile to maja aayega lekin mujhe nahi pata tha wo din itni jaldi aayega Us din Saturday tha mai aur mere dost bahar khel rahe the tabhi maine dekha k ashwini ka pati AMIT aur Beti POOJA kisi kaam se...

2 years ago
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Ashwini 8211 My New Office Manager 8211 Part 2

Hi friends I am back with the next part of my story “Ashwini – my new office manager – Part1!!!”. Just to brief you, I have done my MBA and I have my own training institute. I train corporate people for various personal grooming and as well as professional etiquette. Ashwini became my office manager cum business development tool (to seduce clients). And of course satisfy my sexual desires also. So we reached the airport at 6:30 am and collected our boarding pass. I was getting noticed as I was...

1 year ago
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Win Or Lose It Is Just A Game Part 1

You first have to understand that the five of us have been friends for years. Troy and Austin and been in my platoon on the police department for more years than I care to count. It use to be the six of us but my wife had decided, last year, that she wanted to go "find herself". sad thing was I did not know she was lost! Now Troy is married to Alice and Austin is married to Linda. Let me tell you about them. Alice is short, maybe 5'-0" tall if that. She has black hair and brown eyes that remind...

Bisexual
4 years ago
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Winona Rider Strips

Sloane sat at his desk and smild happily. He led the good life. He kicked back in his black leather chair and propped his feet up on the expensive oak desk. He owned a successful production company in Los Angeles and he made movies. His office was big and decorted with the finest furnishings money could buy. Sloane was very wealthy and owned property all over the world. He was a rich and powerful individual. Sloane was a confirmed bachelor and he had countless women at his beck and call. In...

3 years ago
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Winifred Arrives Rose Cums

This tale starts immediately after "Office Mating Ch. 3" where I got reinstated to my Director position by my boss's boss and met Clara's latest visiting niece Rose, a runner with strong legs who had a lesbian incident with her coach and was vehemently against letting me probe her pussy with my prick. I mean, what's with young women these days, anyway? The next morning I awoke with thoughts of Rose, my neighbor Clara's niece, who got some great oral attention but rejected the thought...

3 years ago
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Winners And Losers

WINNERS AND LOSERS by Throne I'm a man in his early 30s, with an attractive wife and enough money that I'll never have to worry about anything as mundane as a paycheck. My bride Laurie is several years younger than me and quite a beauty. I have the time and money to indulge my hobbies, which include collecting antique art prints, fine dining, and the occasional concert of light classical music. But I also have another avocation, which is a longstanding and deeply ingrained interest...

3 years ago
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Ashwini8217s Erotic Massage

Hey folks, it took a while to pen down my experience. Busy office schedule, appointments, travel had kept me busy. Check the author page for my other experiences submitted on ISS. This experience is penned by both Ashwini and myself. Happy reading. Feedbacks, appreciations, depreciations welcome at It was a cold day during the winter season, I wanted something hot. Not hot food or hot drinks. I was all alone at home. On such days when your partner is not around, it is very tough. I called my...

2 years ago
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Ashwini Subjugated

Im a married guy travelling in a crowded bus… A middle aged woman, a stranger, is standing in front of me…She is a luscious woman wearing a sari… Her blouse is drenched in sweat and shes perspiring profusely in the heat…Im standing Very close behind her… My stomach is pressing against her back which is bare since shes wearing a low cut blouse…My cock is pressed against her ass… I try to control my erection, but in vain…She apparently senses my hard-on but doesnt make a move… Besides, thrs no...

3 years ago
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Ashwini My New Office Manager 8211 Part 1

I am Kailash from Mumbai. 26 years old single. Any women wanting to have sex chat with me just drop in a mail on I have done my MBA and I have my own training institute. I train corporate people for various personal grooming and as well as professional etiquette. Initially I used to manage things from my home and single handed. But with Gods grace my client list started to increase and was difficult to manage things myself. I bought an office in posh mall of Malad and appointed 2 staff member...

3 years ago
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Win or Lose

After an interminable wait, my wife called for me to come down the hallway to the door of the master bedroom. Hanging from the door knob was something black with a bright post it note attached. I pulled off the note and read it, my excitement reaching a peak. ‘Put on the hood and come into the bedroom. Speak only when spoken to.’ The black object was a leather hood with a zipper in the back and holes for the eyes, nostrils and mouth. I pulled it on and zipped it into place before opening...

3 years ago
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Periwinkle Pink Part 2

Periwinkle Pink Part 2 By Cheryl Lynn This is a force feminization fiction story. Part 1 should be read first for this to make sense. Any similarity to real life is purely accidental. It is not for the sweet/sentimental reader. All standard disclaimers apply and may be downloaded for personal use only. Any other use by author's permission. Comments are most welcome at [email protected]. Periwinkle Pink Part 2 As Perry stepped out of the bathroom, he was blushing as...

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