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Username: freefall Password: ******* As always, I checked out the chat rooms after I logged on. I searched the list: sissy cross-dresser; cross-dresser for m; cross-dresser for f; but all my favorites were full. I even tried them, just to be sure. Access denied. Room is full. I hated when they were full. Also, none of my buddies were online yet. So, I scrolled down the list of rooms, trying to find one to enter. I never really chatted in them anyway. I liked to enter, check out people's profiles, halfway follow the dialogues, and hope someone would IM me. Or if someone looked interesting, or local, I'd IM them. Usually just to found out a little about them. If they were another cross-dresser, I'd find out what they liked, if they had advice, or just have some interesting conversation. A few months ago, before I decided it was better to be honest online, I might mess with them. One night I'd be a horny female, the next a pre- op TS or maybe just a young, hung stud looking for action. Now, I actually had a real profile and told the truth, except for exact name or location details. Tonight I was ready to go look elsewhere, when I saw the cuckold husband room. I used to go here, before I decided to concentrate on my sissy side and be honest in my conversations. Cuckolds were men whose wife would have sex with other guys. The other guys were known as bulls and often they liked to dominate the cuckold as well as have sex with the wife. I'd play the role of pussy-whipped husband, sent to find studs for his cheating wife. The horny bulls loved it. Of course it was all fantasy. Most knew it, I think, but it was still fun cyber. But once I decided to come clean with my real interests, I stopped visiting the room. I had nothing really to tell them. The room was only half full. It didn't take long to see who was there. There was just the usual mix of cucks and bulls. Little real room action, most talking took place by individual IM. I was getting ready to leave, when the IM window popped up. "Cuck or bull?" That was the standard entry from one male to another, especially when the profile wasn't clear as to your preference. Mine wasn't. I talked about my wife, state, and hobbies. Honest, but not specific enough to single me out. I could tell from the name, MTNBULL, what he was. I answered honestly. "Neither, I'm a married cross-dresser." "Does your wife know? Does she dress you?" "No, I've fantasized about it, but nothing more." "Too bad, I like fem husbands. I could get her to dress you, if you're interested." "I don't think so; she's pretty old fashioned." "I know, but I have my ways. I've helped many sissy husbands find their true place in their marriage." From then on, we chatted. I admit he had a way to him. He was very personable and friendly. Most of our chat was about my wife or me. He was a good chat listener. I told him I loved to cross-dress, was prone to be submissive, and my fem name was Missy. He gave me just enough background to find out he had been a bull for some time. He said his name was Clint and he lived in the mountains close by. Once we established how close we lived to each other, he began to ask how he might meet my wife. Did she chat online? Could we meet him at a bar or a restaurant? His interest and charisma made this much more exciting than other bulls I had talked with. Before I knew it we had talked for nearly two hours. Finally, I had to sign off. As a parting message he said to think about how we might get my wife involved. He said if I could get her to talk with him, he'd guarantee that she'd be more than willing to make me a fem husband. After I signed off, I chuckled. Knowing my wife Jennifer, she would not be easily talked into anything or most likely not even be interested in meeting or talking with him. During the next few days, this conversation kept coming back to me. I couldn't forget how assured he was. He knew he could convince my wife to participate in my cross-dressing. This had long been a prime fantasy of mine, and even though it seems remote, I couldn't forget it. As I thought of that chat, it always progressed to how I could introduce Jennifer and Clint. She rarely went online and never went to chat rooms. So giving him her online name wouldn't really work. She always deleted email from names she didn't recognize, so that wouldn't work. If we went to a bar or restaurant, she was not the type to start forming a friendship with someone we just met. We had only a few friends we socialized with, and we had known them for a long time. We occasionally did neighborhood activities, but again it only reached a certain level of friendship. None of these encounters ever reached a level of intimacy that would lead to sex or a cross-dressing episode. When I would logon, Clint would IM me to see what was happening. He always made a point of asking me about my cross-dressing. Real detailed questions about what I liked to wear, my sizes, whether I wore makeup, and if my hair was long or short. He seemed to enjoy my detailed descriptions and encouraged me to be more feminine. And I began to do that. For example, instead of getting my usual short haircut, I had the stylist not trim much, but shape it. I told her I was looking for a longer style for a change. Clint never pressed me, but was clear that if I wanted her to put me in skirts, he could deliver. Even then, he was casual about it. As if he was just doing a service for me. The one thing I knew that Jennifer was most passionate about was her love of the Old West. Stories of gunfighters, gold rush towns, and particularly the history of Tombstone, the OK corral, and the principals involved were her greatest hobby. She knew everything about them. Had researched, read, and bought all the books written on them. Then it came to me. She had once had a long-range exchange with an older, English professor who was studying the gunfight at the OK corral. She had answered a question he had posted on a message board about Tombstone. She had really enjoyed this and had often sent him books or clippings for his work. We even exchanged Christmas cards with him and his wife. This might be an avenue for Clint to make contact. The thing was he had to let her make the contact and promote it. Otherwise, she would likely stay remote. I thought about it for a couple more days. To make that route of contact work, I needed to know where the board was. Then I could give Clint the information and he could post a question. That would be the bait for Jennifer. It would then be fate if she answered and was drawn into more exchanges with him. I waited until I was sure she had gone to the board, and then checked the history summary. It gave me all the recent places she had visited when online. She had a Facebook page, a few favorite e-stores, auction sites, and yes, a couple of Old West message boards. I found the one that she looked at most often. Now I had the information, but what to do? Did I really want to play my wife that way? Did I really think Clint could deliver? Or was it just a fantasy? The latter seemed most likely. In fact, I used the scenario to my satisfaction to masturbate quite a few nights. But then, like all fantasies it began to get old. It wasn't enough just to imagine it. What I needed was that next step. If I gave Clint the board name, it would juice everything back up. I could go for weeks expanding my fantasy. And odds are, Jennifer wouldn't even see Clint's message or respond if she did. Finally, I decided to go for it. Good fantasies are hard to create and I wasn't ready to see this one die so soon. I logged on and went about my usual online business. Soon the IM window popped up - MTNBULL. "Hi Missy, you got any ideas for me tonight?" "Hi Clint, maybe so, I think I have a way that might work." "Go on, what do we have to do? I'm dying to see you in some panties." "She likes Western history. You know Wild West type stuff. Maybe if you posted a question about history on a western board, she might contact you. That way, it would look natural and she wouldn't be on guard. But it would be up to you to make more contact, if she responded to your post." "Missy, I think you've got it. That is a subtle but workable approach. And don't worry, once I get her to chat with me, you'll be wearing skirts in no time." "Well, we'll see. The board name is Tombstone_chat.org. You'll need to ask a question about some aspect of the town's history. Maybe ask a question about the famous gunfight or the main fighters. She knows it all, so you must make it realistic. Do you think you can find something?" "No problem little Missy, I'm a fan of the Wild West myself. Actually grew up on a horse farm. I'll check out a few sites, and see what kind of angle to take. What's her e-name?" "Not yet Clint, just let me know who responded to your post and then I'll let you know if she is one of them." "Great little Missy, I'll catch you later." Now that he was gone, I had the first regret. You know it was like lighting a fuse. Nothing had happened yet, but it was smoldering right in front of you. You knew you were safe now, but in a while a real explosion could take place. But it did give my fantasy the juice I needed. It was great imagining how it might go. But even in my imagination, it felt like a fantasy. Jennifer would never participate. The next few weeks slid by. I was busy at work and when I logged on at home, I never received an email or IM from MTNBULL. My fantasy gradually became routine and I had just about forgot about the incident. I thought of it as one of my riskier failures. Then at dinner one night, while we were exchanging chitchat about our day's activities, Jennifer gave me a jolt and re-awakened the idea. Casually, she mentioned that she had seen a question about Tombstone on one of her favorite chat boards. Turns out, it was a local guy who was real interested in what happened to the Earp's after their history making shoot-out. She had emailed him several times and he seemed real nice. She remarked that it was refreshing to have someone local to chat with about it. She often felt she was the only one in this area that liked the Wild West. Plus he was also so polite and friendly, almost like she had known him for years. Her tone gave me the chills, because I had gotten the same feeling when I chatted with Clint. He honestly had a way of making you feel both special and comfortable. I was real anxious about this and had a knot in my stomach. I had assumed that even if Jennifer and Clint interacted on the chat board, that she wouldn't be more than mildly interested. I could tell from her recollection of the interactions that she was more than mildly intrigued. Now, I wasn't sure what might happen next. Plus, it was out of my control. Jennifer and Clint were developing their own dialog and I was on the outside looking in. Of course it fueled my fantasy, but now these masturbatory events had a dark edge to them. Lurking in the background was the possibility that this might happen. Even more sinister was the idea that Clint was a sexual predator and he was longing to have sex with my wife. Not only that, but he wanted to make me seem like less than a man while he did it. Although this was great fantasy, I wasn't ready to take that radical a step in real life. I spent the next few days in both a sexual heat about the fantasy and a dreadful apprehension of where they might be going. I kept checking online, but I had not seen MTNBULL for some time, and I was afraid to email him. My one hope was that perhaps he didn't know that the person responding to his questions was my wife. My fears about Clint were well founded. When he had posted the notice on the Tombstone board, he had used another online name. He had a couple of people respond, but with a little checking he found only one was local. He figured this had to be her. Once he focused on her, he had emailed almost daily. First with questions about Tombstone, the Earp's, and the Wild West, then he gradually began to interject personal conversations. He mentioned fairly early in their exchanges that he had a steady girlfriend and talked about her often. This helped establish him as a regular person with Jennifer, and not some online stalker. Clint talked about how they did so many things together, but that his girlfriend wasn't as interested in the Wild West as he was. This was a further link with Jennifer. She had often complained to me that I showed little acceptance of her hobby. As they became regular email partners, Clint ratcheted up the action the next step. He noticed when she logged on, and observed that it was almost exclusively during the day, when I was at work. Finally he sent her an IM and began to chat real time with her. This allowed him to work Jennifer with more of his charisma and charm. Soon she began to IM him back and they often would spend an hour or so chatting during the day. Although some of the time was spent talking about their hobby, often the conversation would drift to their partners, work, and everyday life. Clint was good about extracting information, and always inquired about our home life or me. This made him seem more like a close friend, almost like a girlfriend Jennifer could confide in than a male. As he promised, Clint was good at making himself liked. But he always maintained enough distance, that Jennifer wasn't threatened. He was obvious master at the art of conversation and relationships. The newly developed friendship prompted Jennifer to go the next step. She loved to shop and if given an opportunity loved to buy presents for friends and family. Because Clint had demonstrated such an interest in the Earp's, but seemed to be fairly uninformed about them, she decided that one of her favorite books, "Wyatt Earp, the Life behind the Legend", would be perfect for him. She spent several weeks shopping online, until she found the book at just the right price. Jennifer was feeling pretty good. She had found a great book, at a great price, and now would be helping a fellow 'cow poke' to learn more about their interests. This in turn, would spark more conversation and speculation about the various uncertainties associated with the legends. All she needed was his address, and when she logged on early that morning she immediately began typing an email to him requesting a shipping address. However, before she could complete the message an IM popped up from Clint - EASTCOWBOY. "Hi DESERT FLOWER (his nickname for her), how is everything going today? Anything special going on with you?" "Hi COWBOY, nothing special today, I just have a few errands to run later. But I was just getting ready to email you. I need to have an address for you that I can send something to. Would you let me know that?" "Sure I would, but I've got a better idea. I was just going to check with you to see what your plans were for today. I've got some meetings on the west side of Charlotte and thought maybe we could get together for lunch? You pick the restaurant, somewhere you like and I'll meet you there. How about it?" Jennifer was surprised. Even though they lived but 130 miles apart, she hadn't really expected to meet him in person. Not that she was worried; he had made her very comfortable with their friendship. So, it didn't take her a moment to respond. She could meet him at 12:30, if that was ok, at the local Chili's. As they worked out the details, she smiled. Clint had never asked for a picture and she was dying to see if he looked how she had imagined him to be, sort of a watered down version of Kirk Russell. Also, the chance to see his face as he saw the book would be real rewarding. So the date was set. Now she had to hurry. She had just planned on going to the grocery and pick up some dry cleaning, and was dressed fairly casually. But with a more interesting day planned, she began to choose her outfit. Nothing too fancy, but she wanted to make a good impression on her new friend and she figured he would be in a suit for business meetings. She finally picked her new pink and black tweed pantsuit and black turtleneck. She knew the outfit highlighted her bust and small waist while hiding her larger bottom. The right amount of makeup, featuring her lovely large brown eyes, and styling her hair efficiently with her curling iron and she was ready with time to spare. Although she wouldn't admit it, this was as close to a date as she had had in a long time. Walking into the restaurant, she scanned the bar looking for suitable candidates. Clint surprised her as he stepped out from a side area, and politely asked if she was expecting to meet a cowboy. Jennifer felt at ease right away, but what really took her back was how he looked. She had imagined an ordinary guy; about 5'10", appropriate in weight, and hoped he would be decent looking. When she saw him at first she was stunned. Clint was tall, probably 6'3"or more. He was thick across the chest, but not heavy. He wore tight blue jeans, a leather sport coat, cowboy boots of course and a white shirt. But what really caught her eye was his mustache and thick dark hair; he looked like a younger version of Sam Elliot. She was expecting to find a nice guy, but Clint was much more attractive. The lunch went really well. They had a great time. He loved the book and they spent a lot of time talking about their partners. He even showed Jennifer a picture of Vicky, his girlfriend. It was obvious that Jennifer and Clint enjoyed being together. Jennifer promised that they would do it again and Clint kissed her hand as they parted. All she could think was that he was a real gentleman. I nearly choked when she told me at dinner. Jennifer gave me the whole story, although she didn't provide many details on Clint's appearance. To her it was just an innocent lunch and a chance to firm up a new friendship. She beamed when she described how he had reacted to the book. All I could do was nod quietly. Was she telling me everything? Had Clint told her we had chatted? Did he broach the subject of my dressing? Had he tried to make sexual advances on her? A million questions ricocheted in my head, but I just sat meekly and let her finish her story. Finally, I softly replied that it sounded like you had a good time and he seemed nice. I didn't know what else to say, or do. I kept replaying the incident over and over in my head, each time reflecting back on my fateful IM that gave Clint the key to contact with Jennifer. Why? Why? It was just supposed to be a fantasy. Now I had made it far too real. I knew Clint would pursue this even more. Maybe if I could talk to him tonight, I could persuade him I no longer wanted to involve Jennifer in my cross-dressing. It was a long shot but all that I had. I logged on apprehensively that evening. I had tried to come up with the right approach to convince Clint to end this, but wasn't sure of it. Before I could search or bring up a chat room, an IM flashed on the screen. "Hi Missy. Thank you, thank you, and thank you. You sissy cucks never realize how grateful a bull is when you set us up with your lovely wives. All you're thinking of is your needs, but a bull appreciates what treasure you have." I couldn't help but blush when I read this. I knew he would not back off and his assessment of my motive was dead on. I tried to think of a reply, but nothing left my fingertips. "Your wife is stunningly attractive. She is going to be so much fun to fuck. I could tell right away that she will be hot in bed and she is so ready for it. You must have really been letting your husbandly duties slide. It's rare that a woman that beautiful is so in need of a good fuck. Thank you again." Again I sat there, doing nothing. I wanted to tell him to stop. Don't talk about my wife that way, but I knew he had seen that desire, because it was true. Jennifer and I hadn't made love in months. "Oh and don't think you can stop it now. I could've got her to a hotel this afternoon and you would be none the wiser. I may not be perfect, but I do know people and I can judge right away whether I can make the sale. She is as good as mine. But don't worry that I'll back out of our deal. After talking with her today, I can deliver my promise to you as well. I will have no problems getting her to help make you a full blown feminized husband. But it will be a cuckold sissy husband. That's the price of the deal. So you can plan on it." At this point, I finally replied. It was a meek response, with as much of a challenge as I could muster: "Don't be too sure this will happen. My wife is faithful, loves me, and wouldn't do anything to harm our marriage." "LOL. Who said anything about harming your marriage? She will be more committed to it than ever. She'll still have you to provide for her, and she'll probably start making you do the housework too. I will point that advantage of a sissy out to her, once I get you in panties for her. Plus she will finally get some real man sex. You never mentioned it, but I could tell that you are less than endowed if you know what I mean. The average male is about 6-7 inches erect, but I would bet that you are much smaller than that, probably less than 5 inches when hard. I don't normally brag, but I can give her much more than that. And I really know how to use it. I know you've heard guys boast online about size before or even show you one of those porn site cock pictures, but I'm for real. Check your email and see for yourself." I was shocked. He was so confident about her and being able to sissify me. It was totally scary. Plus, I had to admit he was right about my small size. When I was younger, I convinced myself that it was average in length. But a few years ago, in one of my real submissive moments, I had measured it. It was just over 4 ? inches hard and when soft it sat there barely visible. I knew from locker room situations, that it was much thinner and smaller than other guys. I had just put it out of my mind. "Missy, I've got to go. Be sure and check your email. Don't worry; I'll let you know when I decide to close the deal with my new fuck toy. You just be prepared to do as I say." With that he was gone. I sat there, staring at the screen, until my Mail icon popped up. Apprehensively, I opened Clint's email. My only hope was that it was just another copy of the large guys featured on porn sites. As the picture scrolled down my screen, all my hopes were dashed. The picture showed the cover of the Earp book Jennifer had eagerly bought for him. His cock lay across the cover with its head right at the upper edge of the book. The way it laid there, it looked huge. Not only long, but also thick as well, and a large bulging sack at the lower edge of the book, indicated his balls were proportionally matched in size to his penis. I quickly closed the email, and anxiously reached for the book that was on a shelf next to the computer. I fumbled through the desk drawers till I found a ruler. Hesitantly, I put the ruler next to the book, just where his cock had been. My heart sank as low as I could remember it. He was not lying; his cock was easily over 9 inches and it hadn't even looked completely hard. I knew Jennifer had never experienced anything like that with me. If Clint did fuck her, as he said, she would likely be really disappointed when I tried to follow that experience. I logged off and could do nothing but fret the rest of the evening, Clint's boastful words flashing through my mind. Clint knew the next few weeks were critical. He never contacted Missy and made a point to IM or email Jennifer every day. He was always getting to know her better, to have her see him as one of her close friends. Not that he didn't subtly begin to interject sex into some conversation; it was just that he did it smoothly. Electronic flirting. He was very good at it too. While Clint ingrained himself with Jennifer, Missy worried more each day. The lack of interaction with Clint was making him both nervous and a little more hopeful. Maybe Jennifer had said no to him. Maybe Jennifer had gotten bored with him. Maybe Clint had moved on to someone else. Clint was counting on this. He needed Missy to be totally vulnerable, and to follow every suggestion his new bull made. Not that Clint doubted that he could have sex with Jennifer. He knew he could score. But what he loved was how the husband looked when he took their wife. Especially, if Clint could fem them - that was the total power trip. The rush from watching the wife see her husband as a sissy and her realizing that she could still have explosive animal sex, with him, and have a sweet little plaything was something Clint never could get enough of. To be honest, Clint had never found the right couple to take it as far as he wanted. He thought with the right couple, he would aggressively feminize the man, while enjoying the woman. Eventually he might move on from the couple, but only after he had trained the husband and given control to the wife. But the first step, where the husband willingly followed his directions was critical. Missy had to take the initial steps himself; otherwise Jennifer wouldn't be open to all that would follow. Most women would not have sex with another man, in front of their husband, or watch him prance around in lingerie, or be comfortable with their husband blowing a man; Clint knew he had to make this transition just right or it would fail. However, Clint didn't need to worry, luck was on his side. I was busy at work, when the phone rang. It was Jennifer and she was so excited she was almost breathless. "Honey, do we have any plans for the first weekend next month?" "Nothing really, what's got you so excited?" "You won't believe it. There is a western convention coming to Asheville, that weekend. They will have all kinds of memorabilia, displays, and some lectures about the Wild West, including a special session about the shootout at the OK Corral. I couldn't believe it. We have to go. Can you make it a long weekend? We would go up on Thursday." "I guess so; I have plenty of vacation left." "Great and now for the special surprise, we can stay at the Sheraton on the River for free! You remember my friend that I chat with about the west, Clint? He says his friend owns the hotel and he can get us a room. He wants to meet us there. He seemed as excited about it as I was. Can you believe it?" I don't remember what I said, all I could think about was he had done it. We were going to meet him. And we were going to his turf. There was no way he wasn't going to try to close the deal. I was confident of that. I was trying to think of way out, but knew it was hopeless. I hadn't heard Jennifer this excited in years. So now I would reap what I had sewn. Clint couldn't wait for Missy to log on that night. He knew it was time to seal the deal. Once he heard at the Clifton chamber meeting about the convention for western memorabilia, he knew the game was on. A quick call to Randal to line up the room and then he went for the kill. Jennifer was so excited he got a hard on just talking to her. He could see her already, naked, her breasts flushed and nipples hard, her cunt lips glistening and swollen, begging to be taken, begging to feel his hard cock, to feel the kind of fullness she had never had. And above all he would be sure to have Missy know about it, to have him in panties and submissive. That was the kind of image that made Clint hard. He wasn't sure why, but he knew he should log on that night. After talking to Jennifer, he had stumbled through the rest of the day, the events all a blur. After dinner, he sat down at the computer, and went online. He didn't have to wait long. "Hi Missy, you excited about the great news? The time for you to become a sissy cuck is here." "Hi Clint, yes I guess the time is here. I'm just not sure I still want to do this. I mean, do you need to do it this way?" "LOL. It's too late now little girl. I am going to fuck your pretty wife. Give her the big meat she's never had from you. If you don't want to play so be it. I'll just make her mine. But, understand, having her sneak off to meet me to fuck will be worse than if you just follow our plan. Not knowing when or how often she is meeting me will consume your waking hours. But, I'll give you the option. You wanted me to get Jennifer to dress you, put you into pretty things. I can do that but you must follow these instructions." "First, I want you smooth. You must shave everywhere. You can leave a little patch over your tiny dick, but I want you smooth everywhere else and I mean everywhere. Second, when we meet, I want you to follow my lead. If I ask you to do something, I want you to do it. And do it with enthusiasm. Finally, when I call you by your sissy name Missy, I want you to call me sir. To show me the respect I deserve. You do these three simple things and you'll get your dream. You've made the payment. I'm going to make your wife my little fuck toy. If you don't want to be the sissy you dreamed of then that is your choice, but I'm collecting my fee." With that, Clint signed off. I just sat and stared at the screen. Like most things you dread, at first they seem a long way off. But before you know it, the time is at hand. It was that way for me. I had scheduled my vacation and we had packed everything for our long weekend. The weeks of anticipation were over. Jennifer could hardly wait to go tomorrow. I felt trapped. Standing in the shower, I began to shave. Although I was not extremely hairy, it took longer than I had expected. I half expected Jennifer to ask what I was doing. When I stepped out to dry off, I could see how more feminine I looked without hair, Clint was right, it was an important step. I quickly slipped into my pajamas and got into bed. Luckily, Jennifer was already asleep. The drive to the mountains was uneventful. Jennifer was planning out her trip, talking about all the activities at the convention. All I could think of was her fucking that huge cock. How our life would never be the same again. Soon we were there. We checked into the hotel and it was very nice. More than just a room, Clint had arranged for a nice suite with a balcony and view of the mountains over the river. The bedroom was dominated by a very large bed, with silk sheets and there was a fireplace and Jacuzzi. It was wonderful, a perfect place for a wild weekend of sex. I was sure more than ever that Clint was a master at this. Jennifer took a lot of time getting dressed. She wore a nice sleeveless black shift, short and form fitting, with black lace underwear and black ankle strap heels. It was a bit dressier than what she would normally wear, but you could tell she wanted to look good. Finally we left for the restaurant. We were to meet Clint and his girlfriend there for drinks and dinner. As we walked into the restaurant, Jennifer saw Clint at the bar and smiling widely, waved at him. At the table, she introduced him to me and vice versa. He explained apologetically, that Vicky couldn't join us tonight. At the last moment she had to cover for another pharmacist. He was at a small cocktail table sitting on a wide leather booth. There was only one other chair, a small, high stool. So Jennifer slid in next to him, leaving the stool for me. Before I could sit down, Clint chimed up. "Mitch, how about you getting us some drinks? I'm buying. Get me a double Jack on the rocks, and you two can have glasses of white Zinfandel." "Sure Clint, I'd be glad to." It wasn't lost on me that white zin was Jennifer's favorite drink or that he had me drinking it as well. It was like I was too much of a light weight to drink real liquor. I quickly got the drinks and brought them back to the table. As I tried to give Clint back his change, he shook his head no. "Good job. You keep the change as a tip. You make a nice waitress. Have you done this before?" His laughter seemed genuine and Jennifer giggled along with him. Sitting on the little stool, I felt like I was perched there. We engaged in rapid small talk, mostly about the convention and Jennifer laid out her plans. I sat there almost like a spectator. Before long we had finished our drinks. Clint looked at me and peeled another twenty from his wallet and gave it to me. "How about another round of drinks for the table, waitress? You don't mind getting them for us, do you little Missy?" The name burned my ears, but I knew what he expected as a response. "I'd love to sir. I'll be right back." I said it in as playful a manner as I could. Like I was going along with his joke about me being a waitress, but it caught Jennifer's attention. I turned and left for the bar, before she could see my face flush. "You know Jennifer, I don't mean to be rude, but your husband is not what I expected at all. I thought you'd have a real masculine guy for a spouse. You know, a man's man. Given how attractive you are he really surprises me." "He's more of a man than you think. He's just being friendly is all." "Oh he's friendly enough, but it is more than that. I can't think of an easy way to say it. Jennifer, he is just a pantywaist. I know lots of guys like him. They are not comfortable being a real man. You know, taking charge, making decisions, being the boss. Not that there is anything wrong with pantywaists. They can be real helpful, like getting drinks." "Well I think you're wrong about him Clint. He is pretty strong at times. I would never call him a pantywaist. He just likes to go along and help out." Jennifer said this with as much conviction as possible, but she did wonder about Mitch some times. In the past, she had often wished he was more assertive, and not just when they had business dealings, but in the bedroom as well. Tonight, he had just met Clint, but called him sir and practically ran to get our drinks. Given how nice Clint had been, she was a bit surprised by his comments, which made her value his assessment of Mitch. Clint had been a straight shooter with her so far, why would he say something if he really didn't believe it? Maybe she just hadn't noticed Mitch's true nature. "Well I can prove it to you if you want. I bet I can get him in a pair of panties before we leave the restaurant. Earlier today I bought some lingerie for Vicky. It's in my truck. I'm sure I can get Mitch to put them on. If I win, we go out after dinner to a fun little cowboy bar I know about. If I lose, then dinner's on me. Do we have a bet?" Jennifer didn't know what to do. She really doubted Clint's claim, but Mitch was acting so submissive. Finally she agreed to the bet, just as Mitch returned to the table, partially because she felt sure Mitch wouldn't agree. But if he did, then well, she wanted to see where it went. I still felt like I was blushing when I got back with the drinks. I knew better than even to offer the change to Clint. I tried to sit down, but he quickly spoke up. "Good job, Missy. Just keep the change, because I have another favor to ask. I need you to go out to my truck and get a couple of things for me. On the front seat, there is a wrapped package and a small gift bag. Take these keys, it's the black club cab Ford parked by the entrance sign." I took the keys, and then knowing he expected it said, "Yes sir I'll be right back". Jennifer couldn't believe her ears. She looked at Clint and then back at Mitch. He certainly was acting like a, well at least not like a tough guy. Clint resumed his conversation with Jennifer and soon she was immersed in talk about their plans for the weekend. It almost caught her off guard when Mitch returned with two packages. "Thanks little Missy, you have any problems finding them?" I blushed deeply even before I answered, "no sir, no problems at all". I even gave up the pretense of trying to act like I was joking around. I sat down, and couldn't look Jennifer in the eyes. Clint took the packages and handed the larger one to Jennifer. She smiled and acted very excited as she opened the gift. It was a book about western gunfighters - she loved it and leaned over and gave him a quick peck on the check. It was just a gesture a friend would make, but the look Clint gave me, made me feel tight inside. "Glad you like it Jennifer. When I saw it I knew it was just what you needed." Although she had just reacted with the kiss, Jennifer was surprised after she did it. I mean it was just a friendly peck, but in front of her husband. But Mitch didn't seem to notice, or more accurately didn't seem to object. He just looked down at the table after a quick glance at Clint. Maybe Clint was right, and she thought it, maybe Mitch was a pantywaist. One thing she did know was that Clint was not. He was making her hot and so she decided to see what might happen and not worry about it. She looked at Clint and took his hand, as she answered him. "Oh yes, I've seen it in book listings, but since it was out of print I could never get a copy. How did you get it?" "Just perseverance, once I made up my mind I knew what you needed and I just worked to make it happen. That's how I am in everything." Clint grinned slyly at me, although it wasn't needed. I understood his message and knew now there would be no changes in plans. Just how it might happen would be the only surprise. "Ok Missy, now you open the gift bag." I didn't expect that. So I opened the bag and reached in with some trepidation. I felt the silky material before I even took out the item. I didn't know what to say or do when I pulled out the panties. They were a lacy v-string style in a light blue color. I just held them there, on the tips of my fingers, as we all looked at them. "Well what do you think Missy? Are they pretty?" "Yes sir, they are very pretty. But why give them to me? These are for women." "That's right those are women's panties, but I thought you might enjoy them. Sometimes pretty lingerie is enjoyed more by the man than the woman. Do you think they will fit?" "I guess they might, but I wouldn't know for sure unless I tried them on." "Oh you want to try them on for us? I was thinking they would be a nice gift for Jennifer, but thought it was too forward for me to give them to her directly. I love to see Vicky in sexy lingerie and thought you might feel the same way about Jennifer. But if you want to wear them, I guess I understand. Lots of waitresses wear sexy stuff under their uniforms." "No, no, if they were meant for Jennifer then that is fine. She can try them later. I was just confused by your question." "Come on Missy, it is obvious you want them. Some guys like wearing panties. It fits their nature to be in women's lingerie. I get the impression you're one of those guys. It will be okay if you go to the restroom and put them on. Isn't that what you really want to do Missy?" I felt trapped. Like the night Jennifer told me about chatting with Clint. I knew he expected an answer and wouldn't take no. So I agreed. "I guess I can try them on sir." "Good girl, and while you're at it try the matching bra in the bag as well. It's got a bit of padding and shaped cups that I think will fit your body type. They should enhance your look quite well. But don't be shy, I expect you to wear them if they fit." As Mitch left, I couldn't believe it. Clint had been dead on right about him. I mean he was going to put on panties and a bra in a restaurant. I had to smile though. It was hot to see Clint manipulate him like that. I always wanted Mitch to be more forceful, as that is so sexy. So, if he wouldn't do it maybe Clint could. "What I tell you Desert Flower? He is a natural panty boy, so it looks like we go out for a drink and a little dancing after dinner?" "You were right Cowboy. I would have gone anyway, it sounds like fun. Mitch would never want to do that." She gave him a big smile and squeezed his hand. Maybe this weekend would be better than even she had hoped. "Well I'm glad to hear that, but I want you to do me a favor. I think you need to find out more about Mitch and his sissy side. So if I suggest something for him, will you back me up?" Jennifer was intrigued by his request, so she smiled and nodded her head yes. His forceful squeeze of her hand sealed the deal. I knew I was blushing when I got to the table. I was carrying the bag with my underwear, and could feel the straps and tight band of the bra. I didn't even want to look up, but did so as I sat down. "How did they fit Missy? I guess ok, because I can see your bra. It's very pretty. You can show us the panties later." With that he laughed loudly and Jennifer joined in. This was worse than I even imagined. We then ordered dinner and I got through it somehow. Every time I looked at Jennifer, she just smiled and continued to chat with Clint. I sat there silently the whole time. Finally, after Clint paid the bill, naturally, we got up to go. They had told me about the cowboy bar and I just nodded my head. By this time, I had no resistance to anything Clint suggested. Clint offered to drive and indicated that I should crawl in the back seat. Once we were in the cab of his truck, Clint turned to me. "It's time to show us how your panties fit, little Missy. Why don't you slip off your pants and let Jennifer see if you look sexy?" "Yeah honey, I want to see if they looked as pretty on your little butt as they did in your hands." Jennifer giggled as she spoke, and Clint looked at her. He knew this was a very good sign that his plan was working. I took off my shoes and slid my jeans down to my knees. I wanted to only pull them far enough down my legs so they could see the panty. Clint would have none of that and grabbed the bottom of one leg and pulled. I slid off the bench seat, with my legs in the air, and he grabbed the other pant leg as well. With a strong pull, he finished removing the jeans. As he held my pants, I got off the floor of the truck and sat back down on the bench seat. My face was starting to burn with embarrassment as I realized my bare legs were on display. In the humiliation at the restaurant I had forgotten about my smooth hairless skin, but he pointed it out right away. "Do you keep your legs shaved Missy? That's a nice touch. I like the way your panties look against your bare skin. You must be a natural for them. I guess not being very big down there is a big plus for you. But with your legs being so smooth, you should wear skirts and not hide them under those rough jeans. I think I have just the thing." Reaching under the front seat, he pulled out a small carry-on bag and showed it to Jennifer. He opened it, reached in, and took out a pair of lace-top stay-up stockings in a dark brown color. "Vicky keeps this bag in my truck in case we get caught out in the rain or she needs a change of clothes. Given how well those panties fit, these clothes should do just as well. Here put these stockings on those pretty legs, they will look better on your bare legs than the jeans. I think she keeps a skirt, top, and some shoes in here too." Jennifer looked at my shaved legs, glanced over at Clint and back to me. I could see a puzzled expression on her face. She reached out to feel how smooth my leg was as if to convince herself she was seeing correctly. Then, with a smirk she took one of the stockings and rolled it up. Looking me in the eye, she grabbed my foot. Putting the hose over my toes, she worked it up my leg. "That is how you put on a stocking. Clint seems to be right about you again, hose always make shaved legs look sexier. Go ahead and try the other one, Missy." "That's the spirit Jennifer. I couldn't have said it better." I could hear the gloating in his voice as we both realized his plan was succeeding. I reluctantly took the other stocking from Clint and put it on the same way Jennifer had. I glanced quickly at her face and could see the mix of confusion, anger, and pleasure in her eyes. I could tell she didn't understand why my legs were shaved or I was acting this way, but had decided to follow Clint's lead to see where it went. He continued to direct the action. "Take off your shirt and let's see if your new bra looks as pretty your panties." I unbuttoned my shirt and slid it off my arms. As I did so, I knew Jennifer would notice my bare chest under the blue bra as well as the lack of hair elsewhere. With my shirt off, I felt vulnerable and somewhat instinctively crossed my arms as if to hide my breasts. "It's okay Missy you can show it to us." I reluctantly moved my arms to my side. Clint laughed and Jennifer joined in as I followed his order. I sat there feeling as embarrassed as I ever had in front of my wife. She was obviously enjoying the show. He continued and told me he wanted to see me in the whole outfit. As he spoke, Jennifer reached in the bag and handed me the skirt, a short mini in light blue with dark blue flowers and white lace trim around the hem. After I took the skirt from her, I slipped my legs in it, pulled it up to my waist, and zipped it closed. She next pulled out the matching blouse, a sleeveless V-neck with lace around the neck. Although embarrassed, I dutifully put it on too. I was sure that she noticed my smooth underarms as I slid the top over my head and down my body. With the clothes on, Jennifer handed me the shoes. The 3-inch heels were navy slides with a double band and they fit easily over my stocking feet. Jennifer looked me over and decided I needed to be bigger on top, so she took some tissues from a box on the seat and stuffed my bra. The whole time they were smiling and laughing as if they were watching a comedy. Finally I finished dressing. Jennifer looked at me intently, and took her hand to play with my hair. "All we need now is a little makeup and something for you hair and you'll look real cute. There's a scarf attached to a hair band in Vicky's bag and I have lipstick and eye makeup in my purse." At this point, Jennifer was obviously enjoying this. I thought I would too when I had imagined her dressing me. But now that it was real, it was a much scarier and embarrassing situation. Using her hair brush, she combed my hair backwards, and worked the hair band in to keep it in place. The scarf covered most of it, giving the impression that my hair was longer. Jennifer teased out some bangs so that it looked more feminine and applied her makeup. She was grinning widely the whole time, making little comments about how the mascara really opened up my eyes, the shadow was perfect for my eye color, and the lipstick made me look kissable. I couldn't believe how easily Clint had convinced her to help feminize me. When she had finished my makeup, Clint started driving while she fiddled a little more with my hair making me more fem looking. I didn't even know where we were or how far we had gone, when Clint pulled into a parking lot. "Well little Missy, let's go, step out and we'll see how you look." They both slid out of the front seat and he opened the rear door for me. Not knowing what else to do, or what to expect, I got out. Straightening my skirt and adjusting the blouse, I finally looked up to see them standing there holding hands. We were just outside a log cabin structure and I heard some upbeat music playing inside. I had never felt as vulnerable as I did standing there and certainly wanted to leave, so I spoke up. "Can we leave now? I want to go to the hotel and get out of these clothes." "Come on Missy, let's go have some fun. You look very cute and after all the trouble we did to get you dressed, you ought to at least show some appreciation to your wife and let her check out this fun place." "Of course, he will go. I mean you don't want to just stay out here in the parking lot do you Missy?" Not knowing, what else to do, I nodded my head and followed their lead into the bar. I was petrified. I mean, I had never been cross-dressed in front of anyone before, and now I was going into a dance place. It was a typical layout, with a big bar in the middle, a lot of tables and chairs next to a dance floor, and some secluded booths at the back. There wasn't much of a crowd with lots of open tables. Clint headed for a booth and pulled Jennifer in next to him. Peeling off another twenty, he told me to get another round for them. I noticed he hadn't included me in this drink order. Not knowing what else to do, I shyly approached the bartender and spoke in a soft, hopefully feminine voice. "Can I order a couple of drinks?" "Sorry miss, but we don't take orders at the bar. Go back to your table and I'll have a waitress come over." Relieved that I passed this first test as female, I turned and headed back to Clint and Jennifer. "Where are our drinks, little Missy? Did you forget what you were supposed to do?" "Sorry Sir. The bartender wouldn't let me get them and said he would send someone over to take our order." "Well that's not going to cut it. Go back and get the drinks." Not knowing, what else to do I went back to the bartender. "Can't you let me order something to drink? My friends don't want to wait and I really want to keep them happy." "Like I said, only waitresses can serve drinks here, so unless you're willing to volunteer to be one, I can't help you." "Ok I'll do it, if I can take them a drink." Smiling and shaking his head as if he had seen everything now, he reached under the bar, feeling around to find what he needed. He finally put a tray, a small metal cash cup, and a white eyelet apron on the bar top. "If you really want to do this, just put the apron on, and I'll mix your drinks. What do they want?" I told him the order as I tied the apron around my waist. It was a half apron, with a scalloped lace edge. I noticed it didn't look too bad against the lace trim on my skirt and blouse. After he poured the drinks, I paid him, put the change in the cash cup, drinks on the tray, and headed back to Clint and my wife. As I approached them Clint had a big grin and Jennifer was openly giggling. "Well, well, well. Looks like you have a real liking to be a waitress. I must say that little apron looks good on you and pretty natural too." Jennifer continued to giggle, but I spoke up, trying to explain everything. I already knew the situation was out of control, but I wanted to try to defend myself. "I had to do this. The only way he'd let me bring you a drink, was if I agreed to dress like a waitress." I put the drinks down on the table, but didn't know what to do next. Neither Jennifer nor Clint made a move to let me in the booth. As I stood there, Clint reached in his pocket and brought out another twenty. "Since you seem to like your new role, why don't you go over and buy a drink for those two cowboys sitting at the back table. That way you can continue to be a pretty little waitress. Jennifer and I would like a little time to ourselves." I stood there a second and looked at Jennifer. She just smiled and glanced over at Clint. Again, not knowing what else to do, I took his money and went to the table. I told the men they had a couple of free beers coming. They look real suspicious, but eventually smiled. They told me what they wanted and I took their empties. At the bar, the bartender seemed a little surprised, but he gave me the beers and change. I took the drinks to the guys and was embarrassed when they gave me a small tip. I tried to turn it down, but they just grinned and told me to keep it cutie. Blushing I headed back to the bar. Not knowing where else to go, I sat on a stool near the bartender. There weren't any other customers near Clint and Jennifer or the cowboys, so I just looked around. There was just one waitress, some people were dancing, and a few couples sat at tables near the action. Clint and Jennifer got up once and did a slow dance, holding each other closely. I could see he was leaning in close, whispering in her ear. After the dance they went back to the booth where they continued to sit close and Clint talked to Jennifer. He had his left hand on her thigh and she was holding his right one. She had a half smile on her face and whispered back occasionally as they spoke. Getting closer to each other as they talked, he leaned in and gave her a small kiss. I saw her eyes close and she kissed him back, opening her mouth. It was just a brief kiss, but it seemed like forever. I felt my insides twirling around. Not knowing what they were saying or thinking was killing me. The only thing worse was when they finally glanced my way. Then her smile broadened and I could see his hand sliding further up her thigh. It was excruciatingly painful. Clint looked toward me and motioned me over. I nearly ran to the table, going as fast as I could in the heels. "Talk about great service, Missy you busted your cute little buns to get here. Are you having fun being a sexy little waitress?" "It's ok." "Well, that's what I wanted to talk with you about. Jennifer and I can see you like swishing around, serving drinks, and being all cute in your little skirt and heels. So we really don't want to take you away before closing. But Jennifer is ready for me to take her back to the hotel. She wants to be sure that would be ok with you. I told her you would be fine with it. You don't mind if I take her back to the room, let you stay here to be Missy the waitress, and then I'll come back to get you when the bar is closing? You are okay with that plan, aren't you?" They both looked at me as he said this. I could see Jennifer's eyes gazing at me; I had seen that look before. It was mix of anticipation and desire. There was also a little bit of concern that she might be doing the wrong thing. She was looking at me for approval. I noticed as they looked up at me, that Clint's hand had gone further up her thigh and now was totally up her skirt. He had also placed her hand on his crotch, where her fingers were tracing over the outline of his cock. The look in her eyes took on more lust, as her touch revealed what she had imagined before. His size was becoming apparent to her, and she had even more willingness to go with him. I knew before I answered that she wanted to fuck him. I also knew that seeing me in panties, bra, heels and stockings, trying to be as fem as possible, made her see me as less of a man too. That perhaps she really could go have sex with a masculine guy like Clint, because she knew I certainly couldn't supply the kind of sex he would give her. That maybe I didn't even want to be a man any more. Her reservations were gone. Clint had worked his magic like he said he would. So I knew there was really no options now, it was time to pay the piper for making my fantasy come true. "I guess it would be ok for you to take her back." I wanted to say no, that I didn't want you to take my wife. That I wanted my life back like it was before, but I knew it was too late. Clint didn't wait for me to change my answer or put conditions on it. He knew time was critical now. Jennifer was hot. She had enough liquor to lower her inhibitions, and seeing her husband as a pantywaist compared to him had pushed her to ignore any reservations she might have about having sex with another man as a married woman. Missy's permission was the icing on the cake. "Well since you approve of me taking care of her, then let's check with the bartender to be sure you can work here till I can get back. Ask him to come to the table and talk with me." I went back to the bar and spoke with the bartender. He just looked at Clint and Jennifer a little questioningly, but since he wasn't busy, he stepped out from behind the bar and followed me back to their table. As we approached, Clint stood up and shook his hand. "Hi, nice place, I've always liked it here and you make a good drink. I have a favor to ask. My friend Missy is having fun being a waitress and isn't ready to leave. But he wants me to take his wife back to her hotel. So I was wondering if you would mind if Missy stayed here. She'd be willing to work, and do what you want. I'll be at the hotel for a while, but will back to get her at closing." The bartender got a sheepish look on his face, and looked back and forth between me and Clint. He looked me up and down several times, and it appeared that he was trying to figure this all out. He obviously realized now I was a male, but I must have been convincing enough as a female to pass earlier. He also concluded that Clint here was going to have sex with my wife. Finally, he just shrugged his shoulders and said, "Guess it's fine with me, I could use some help, as long as she doesn't want any more than tips. We close at 2 AM, so be here by then." It was not even midnight yet, so the fact that Clint and Jennifer would be gone that long, pretty much indicated what they would be doing. "Oh that will be fine. Just be sure to do as the man says Missy, you understand? Stay here and I'll be back by closing." Without waiting for an answer, he turned to Jennifer, helped her up and started to the door. She glanced over her shoulder briefly, looking at me with a small smile, and she mouthed have fun. Then they were gone. I followed the bartender back to the bar and he told me to start clearing bottles and glasses from the empty tables. Clint and Jennifer walked quickly to his truck, he holding her hand tightly. Inside she was full of butterflies, not knowing if this was the right thing to do or not. She definitely wanted to have sex with Clint, she had been thinking about it the last hour. But she also didn't want to hurt her husband. She just reassured herself, that he had agreed to this, and had to know what they were going to do. She kept going back to the image of him, walking around the bar in the heels and skirt outfit, and how he seemed to be natural at it. She had noticed right away that he didn't stumble in his heels, and that he actually smoothed his skirt as he sat down. It must be something he really enjoyed. Now it was time for her to do something she really enjoyed. The trip to the hotel went quickly, surprisingly so, because Jennifer had felt that they had gone a long way to get to the bar. She was starting to have some second thoughts, but when Clint came around to open the door, he swept her up in his arms. Carrying her to the room, her reservations disappeared. He was obviously much more masculine than anyone she had been with before. She opened the door and they entered the room. As he closed the door, they embraced with a deep kiss. Their tongues probing each other, as were their hands, gliding over each other's body. She had never felt so eager for sex. Stepping back and breaking the embrace, she reached and undid the zip to her dress. It fell softly to the floor and she stepped out of it and her shoes and went to the bed. This was what she wanted, but even so, her own insecurities came out. She wanted to get under the sheets so in case she wasn't as attractive as Clint had expected, that he wouldn't deny her the sex she so desperately wanted. She slipped off her panties and bra and pulled back the cover. Her breasts bobbed softly as she got in bed, their nipples jutting out. As she lay down, she could feel her pussy was wet and ready for sex. From Clint's view she looked very sexy. Her body was attractive, well- shaped, but what made her look so hot to him, was the knowledge that she was a married woman. Not only married, but her husband knew of this and had willingly submitted to his orders. He peeled off his jacket and shirt, and reached down to pull off his cowboy boots. Straightening up, he began to unbuckle his pants. From past experiences he knew this was another important milestone. As others had before, Jennifer lay on the bed and eagerly eyed him as he unzipped and stepped out of his jeans. The bulge in his underwear was obvious; he had hardened significantly since the bar, and now was close to his erect size. As he pulled off his briefs, Jennifer looked at him, almost in wonder. He was definitely the biggest man she had ever seen. Although a few woman balked once they say how really big he was, she was even more eager. His long, thick cock pointed straight at her and she reached out to grab it and pulled him close to her. Pushing her back, Clint spread her legs with his and lay down on top of her. He reached to caress her left breast and leaned in to kiss her again. She could feel the large cock nestled just outside of her pussy, the heat from its touch radiating through her skin. She lost herself in his kiss, and fell back opening her legs wider. She shyly reached down and grabbed the large cock again, and positioned it at the opening of her slit. Clint took the sign and slowly began to enter her. She was very wet, but even so he pressed in slowly, giving her vagina time to expand to his girth. He was amazingly thick as well as long, and he knew that if he jammed in too fast it would be painful, but this was going in perfectly. Jennifer couldn't believe the feeling of him entering her. Before when other men had penetrated her, she could feel the contact, but this was so different. Not only could she feel his cock sliding against her, but it was actively stretching her, multiplying the erotic stimulus she got. The emotions and sensations were coming so fast and so strongly, like nothing she had ever experienced. And it seemed like it wasn't ever going to end, he kept sliding deeper and deeper into her, opening her up to new feelings. She almost felt like he was touching parts of her sex that had been dormant and unused before. All the while, they kissed and felt each other. Her hands grasped his muscles along his shoulders and back, as he caressed her breasts and face. The sensual feelings were building for both of them. Finally he was fully into her and began to slowly, rhythmically fuck her. He pulled back about half of his length, and then plunged in till his balls gently slapped against her ass. All this was so new to Jennifer, feeling so stretched and full, being totally aware of his penis and balls. It was as if they were separated from him. It only took a few strokes before she was overwhelmed by her first orgasm. It happened so quickly, building rapidly to her climax, unlike any she had ever had before. She shuddered, griped him tightly, and let out a moan, soft at first but building in volume as she came. This was what Clint lived for. The first climax he gave a new woman was always special to him, but he had much more to do. He knew it was important that she cum multiple times her first time with him. She must see sex with him as so special that she will continue to want, even need it. Generally, that was not a problem for him and he could tell tonight would not be any different. As her first climax ran its course, he slowed briefly, and then began once again to piston his penis in and out of her. As he fucked her, he slowly reached down and repositioned her legs, pulling them up and back against her stomach, fully exposing her pussy to him. This position allowed him the deepest penetration and he wanted her to feel totally overwhelmed by his cock. He established a steady rhythm and reached up and caressed her breasts with his hands and leaned forward to kiss her hungrily. Jennifer could not believe what she was feeling. He was now even deeper in her and she felt tiny orgasms electrify her body every time he plunged into her. The feelings continued to build and once again she succumbed to another paralyzing orgasm. Only this time, she felt it cycle through her again and again. She had never cum more than once with Mitch, but this was so much more. It seemed like she would climax forever. She could also tell that Clint was building to a climax, as he increased his rhythm and force as they coupled together. Finally, she felt him tense up and it triggered the most explosive climax for her that night. They shuddered, groaned and clasped each other until the emotions had been drained from them. As they lay still next to each other, Clint gradually and gently repositioned her again, so that she was spooned into him. His cock was still buried in her, and it gradually softened but even so still filled her up. His strong arms wrapped arou

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she: Hey sweetie :) thanks for adding me. You're really gorgeous :)i: you too *kisses* time to chat dirty? ;>she: Always ready for dirty chat babe :Pi: *hugging you* and kissing you....feeling your hard nipples poke into mine ^^she: Mmmmmm nuce beginning babe I feel your hard nipples on mine while my hand slipped under your skirt :Pi: our tongues roll around each other while we rub our naked boobs against each. soft moans of pleasure escape our mouthsi: our pussies becoming moist with...

2 years ago
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Chatroulette

I had an affair. Thats how it all started, the wife and I had split up just before xmas. I went on the works do, got pissed and went with the office bike. The wife found out and all hell broke loose. I came clean and the wife said she didn't want to lose me could we try again.I said we had to be honest with each other if we were going to try again. she said ok what do you want to tell me? I just thought fuck it nothing to lose, so I told her I loved the idea of her showing herself to other...

2 years ago
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Magichat

Magichat By: CheshireKitten23 Today was my day off, ever since I graduated highschool I had had plenty of those. Today I was exceptionally bored, all of my friends were busy and video games didn't seem to be as fun. And with that came the ideas of an idle mind, so I went on the internet and trolled. I tried to log onto my usual site but found I was banned "No big deal" I thought to myself. So I searched for new sites to torment the innocent, and on the front page( first suggestion...

2 years ago
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Chatwhore

Chatwhore I was being blackmailed. It didn't start that way of course. It all started about six weeks ago. I was in a chatroom and I started talking to a girl named Rachel. We chatted for a while and then I asked her about makeup. She was amused and asked me if I wanted to put on makeup. If I was a sissy. I meekly told her I was and asked her to help me learn how to do my makeup. Over the next few days she trained me step by step how to apply my makeup. Sometimes when she...

3 years ago
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Gruppenchat

Zugegeben, manchmal habe ich Ideen, die andere schräg nennen würden. Max, meinen Freund, überrascht das nicht mehr, dazu sind wir schon lange genug zusammen, und oft genug animiert er mich auch und kitzelt es aus mir heraus. Seit wir uns kennen - oder zumindest schon kurze Zeit darauf - haben wir unser gemeinsames Interesse an Ungewöhnlichem entdeckt, zumindest würden es Andere wahrscheinlich so nennen, die auf Sex nur im Schlafzimmer stehen, und dabei am besten noch bei: Licht aus, unter der...

1 year ago
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ChatRoulette

Classic Chat Roulette! Even though sites that offered live video sexting existed even before Chatroulette.com, this one really kicked it off since it brought everything together to a much more personal level. I mean sure, the site wasn’t meant to be what it is today, but it was quite obvious to anyone watching the site develop, exactly what would happen to it. The site was bound to become this battleground of random dudes looking for hot chicks that they can masturbate to. And you know, most of...

Sex Chat Sites
1 year ago
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iSexyChat

i Sexy Chat is a straightforward chat site that markets itself as a place to have fun sexy chats with women (or men) around the world. The site asks you your gender and what you are interested in, and from there directs you to one of several chatrooms so you can start your journey of meeting someone to bust a nut with.However, the reality is not quite as fun. Many of the chatrooms are filled with spammers, with hardly any girls and no proper understanding of the people you’re talking with. It...

Sex Chat Sites
1 year ago
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3DXChat

3DX Chat! An (MMO) multiplayer 3D sex game in a virtual world! I’m not usually one to fuck with porn games. When it comes to porn, I am generally not trying to play around. I like to go to my favorite sites, find the sexiest videos I can and get down to business (fap, fap, fap). I have never really seen the appeal of jumping through all kinds of hoops, completing missions and leveling up in order to get to the main event. Why should I have to earn my pleasure? I already do that every day at...

Best Porn Games
1 year ago
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StripChat

Strip Chat! Anyone who has been following my reviews knows I love a good live sex cam site with hot models. There is just nothing like being able to see live, sexy girls doing whatever you ask them to, fulfilling your every command. Plus, the fact that on sex cams, you can interact with them makes camming an online experience on a different level than watching a more traditional, pre-recorded porn video.That brings me to Stripchat—yet another online option for the pervert who likes something a...

Live Sex Cam Sites
1 year ago
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ChatRandom

Chat Random! Are you a bit of an exhibitionist or maybe a voyeur? Do you like chatting with people anonymously online? Or how about a little sexual roleplay? If you answered yes to any of my questions, then you should try out some camming with people online. You don’t need to give your real name, email, or any identifying information if you don’t want to.All you need is a webcam, some time, and be horny enough to get down with some random people on the internet. And a lot of people talk shit...

Sex Chat Sites
1 year ago
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321SexChat

321 Sex Chat! If you're looking for a proper good time where you get to interact with other people and talk about sex, boy, oh boy, do I have to tell you something. While most of us would prefer for these things to happen in real life, why not go for the next best thing.There are many ups and downs when it comes to sexting on the internet. I mean, as long as it is with someone you know in real life, it should all be fine, right? However, when you RP on the internet and whatever, you're very...

Sex Chat Sites
1 year ago
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Chatropolis

Young perverts today have it so good. You’ve got easy access to live WebCam shows, pornographic video games and crazy VR movies that stream the porno straight to your eyeballs. In the old days, your best bet for interactive masturbation was a phone sex line. In the early days of the Internet, sex chat rooms started picking up some of the slack. Chatropolis is one of the old school adult chat sites, operating since 1994.Most of the websites from the mid-nineties are long gone, lost to the ether....

Sex Chat Sites
1 year ago
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FreeChatNow

Free Chat Now! Imagine chatting with sexy bitches at a bar. Not only do you have to come up with some ‘out of this world’ lines they’ve never heard (highly unlikely), you’d also have to keep them interested and entertained long enough before you can get between their legs. You’ll be lucky to fuck an old slut that has knocked a couple of beers, but looking for pussy in this manner may as well be looking for a needle in a haystack.What if I told you that you can chat with sexy people and get your...

Sex Chat Sites
1 year ago
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Chatzy

Porn can be a lonely experience. No, really. After you bust that nut you sometimes realize that you’re just sitting there by yourself covered in cum with Riley Reids horny moans blasting from the headphones on your desk. Not me. I mean, I’ve always got some pussy on standby, but I know it can suck for some of you beta fucks out there. And it doesn’t have to be that way. Everybody gets horny. It’s a fact of life. And there are a fuck ton of people out there who will chat, roleplay, share...

Sex Chat Sites
1 year ago
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JackinChat

Jackin Chat! Bashing the bishop, spanking the monkey, jerking off - whatever you like to call it, masturbation is a normal part of life. Most men masturbate and contrary to popular opinion, so do the women. I mean, everyone gets horny and rubbing one out as you think about the next pussy to hit can’t possibly do you any harm. Trust me, you don’t want a bunch of losers in your sperm bank. In any case, genitals are an important part of your body, and it would be surprising if you were not more...

Porn Forums
1 year ago
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ChatPig

I bet you’ve never heard of a site with a more intriguing name than Chat Pig, because I surely haven’t. Usually, the site’s name should make sense, or give us an idea of what the site has to offer, right? Well, that crap does not really apply here if you ask me. Well, while the targeted audience here are mostly Germans, or so my sources say, when I visited the site, I found a lot of English-speaking individuals so I was confused.Maybe the fact that their name has a Pig in it, comes from the...

Sex Chat Sites
1 year ago
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SuperChatLive

Super Chat Live! Any time you hear a dumb fucker bitch about how the Internet has ruined their life, you need to take your dick out and slap them in the face. They’re ignorant assholes that probably shit out of their mouth and piss out of their assholes, so don’t fucking listen to them. The Internet has given us amazing things! Free porn for life, on-demand lubricant delivered to our home, and camgirls that will spread their assholes for the right amount of tokens.Try going into a time machine...

Live Sex Cam Sites
1 year ago
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LewdChat

Lewd Chat! Who the fuck still uses a chatroom to chat with other horny adults in this goddamn decade? Well, it turns out, plenty of fucking people! This is because so many people want to hop onto a chatroom anonymously and get off with other horny like-minded adults just like them. If you don’t believe me, visit LewdChat and see for yourself!You will discover that there are all kinds of people just waiting to meet you! I was actually surprised by how busy all of the rooms truly were. Every time...

Sex Chat Sites
1 year ago
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ChatPic

Chat Pic! To most of you, chatrooms are a thing of the past. But guess what, they are alive and fucking well in certain corners of the Internet. The concept is still striving strong. From custom XXX chatrooms communities have created on platforms like Discord to IRC chatrooms that are alive and kicking, plenty of sites offer an opportunity to chat with other horny people like yourself.Chatpic is different, though. It takes the concept of chatrooms and transforms it into a picture-sharing...

Porn Pictures Sites
1 year ago
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AdultPhoneChat

Adult Phone Chat! Are you lonely tonight? Don’t want to get on a cam site and show your tiny penis to everyone? Prefer not to meet someone in real life and disappoint them, even if you’re compensating them for their time? Well, I have a low-tech solution for you: phone sex!If you think phone sex belongs in the last century, get the fuck out of here! Phone sex is actually alive and well. It’s always in style. Now, if you live in the UK, you might as well consider the self-proclaimed best phone...

Sex Chat Sites
1 year ago
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ChatMeHard

I like a babe to Chat Me Hard from time to time, because I really do believe the brain is among the most sensual and sexual of organs. Sure, a lady can show you her titties or her hoo-ha and your brain goes straight into horny reproductive mode, but a few well-strung words can have the exact same effect. I know a lot of modern masturbators have gotten used to the futuristic magic of instant 4K porno videos, forgetting all about the older masturbatory formats like text-based cybersex and erotic...

Sex Stories Sites
1 year ago
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ChaturFlix

Chatur Flix doesn’t exactly roll off the tongue the same way some brands do, like the effortless way you can say Brazzers or TikTok. At the same time, I’d argue it’s a pretty effective title for a porn site because it tells you what you’re in for even before you click the link. Of course, that assumes you’ve got some familiarity with the source of their flicks, Chaturbate, but it’s hard to imagine there are perverts online who haven’t rubbed out at least one or two while watching live webcam...

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1 year ago
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iFreeChat

The “I” in i Free Chat ain’t an uncommon prefix when it comes to modern branding. Hell, Apple started tacking it onto their products before the dawn of the 21st century, so a lot of you have literally grown up seeing iStuff all over the place. I initially suspected iFreeChat was just another copycat adding the letter for no other reason than making their site sound hip, modern and technological, but the front page of their site set me straight. “Welcome to Free India Sex Chat,” reads the little...

Sex Chat Sites
2 years ago
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chatroom

Kim logged into the chat room. What did she feel like tonight. A soak in "The Hot Tub"? To plunge into the "Dungeon"? To role play? Then she saw a room she had never ventured into before. "The Fantasy Room". She clicked on the icon and entered. " Hello Kimuk. Do you have a fantasy to share?". Kim laughed at the screen. " Not here " she typed. Immediately she revived 4 private messages . The one which caught her eye was from Dark stranger. " Hello Kimuk. Tell me? Your secret is safe with me"...

3 years ago
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Chatroom

hi there///how r u good so what brings u here tonight im just really horny...got the apartment all to myself....decided to dress up oh nice...so what r u wearing black panties and a tank top very nice...just in some boxers here...r those nipples hard and poking through that tank top? mmm yeah a little bit i think thats so...

2 years ago
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Chat

Me: Hawaii was a good time, remember? We fucked the shit out of each other.Thu: yup, that was greati am glad we didMe: in front of the mirror. doggy-style.you were facing the mirrorThu: while you were talking to Leecan't believe you talked to him for so longMe: haha.Thu: would think you want to get off the phonesince I was sucking your dickhe asked why you were breathing so hardMe: haha. I remember pulling you up when I was about to come and was about to give you a facial but you refusedThu:...

1 year ago
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The taking of Julie

A story about a young couple where she is taken by older and he yields. Comments appreciated.Julie and I moved into a two-flat rental at age 22. We were two young people in love, sill maturing and just starting out. We were both lean and physically developing. I had no facial hair and a young penis with a small tight ball sack below. Julie had 32B breasts and long blond hair. She had a small pubic mound above her sweet tasting, young, tight pussy. For us, sex was always tender and...

1 year ago
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A visit to the VCT

Note : This story is completely fictional! Since I did my form four back in the year 2005, my Aunt has always insisted that I go for a V.C.T. She counsels and tests people for H.I.V in Nairobi while I have been staying in mombasa with my family. When we close college (first semister) I decided to go to visit her at Nairobi where she stays. That is may this year 2008. She is single and lives alone. When I arrived, she took issues with me for not going for V.C.T despite her continued insistence....

Incest
4 years ago
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Milwaukee Cuckolds and Their Trip to Vegas

Milwaukee Cuckold and Their Trip to VegasWe had decided to go to Vegas again but Judy had said I couldn’t gamble 24/7 and she would get to do some sightseeing. We got there on a Wednesday and were staying until Sunday. We were staying at the TI which was a short walk to the fashion mall which was one of our first visits. Judy said she needed some nice outfits for when we went out.She picked out a couple of very sexy outfits that made her BBW body look extremely cum worthy. She then saw a...

3 years ago
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Surprise

Carol and I have been living together for over a year when she told me of her fantasy. She wanted a menage a trois. Being liberal minded and kind of turned on by the idea of having two girls in the sack at the same time, I agreed. I said "Carol, if it's a menage a trois that you want, then by all means lets fulfill your fantasy." In my mind I was wondering which of her girl friends she was going to bring for me. My dick was proceeding to the hard-on phase just thinking about the...

1 year ago
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FamilySinners Dania Vega Step Daddy8217s Girl

Kurt’s (Dereck Pierce) step-daughter goes out for the day, which he takes as an opportunity to sneak around her bedroom. She comes home early so he hides in the closet, when she catches him, she has an unexpected reaction. Lisa (Dania Vega) is going out with friends and is upset because she feels like her stepfather is teasing her about not being able to get a boyfriend. After she leaves the house, he sneaks around her room. She returns home unexpectedly and catches him masturbating in...

xmoviesforyou
1 year ago
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WildOnCam Kit Mercer Some Hot Loving

Wild and bubbly Kit Mercer is ready for some sex and can not get enough of Quinton James hard cock! He knows how to use his tongue as he goes down giving that clit of hers just what it wants as he flicks his tongue rapidly all over it! Kit squirms going wild lusting for that cock to penetrate and fuck her deep! They 69 and Quinton fingers her ass while his tongue is buried deep in that sweet pussy! Kit puts her face to the camera when Quinton gets behind her fucking that tight pussy hard in...

xmoviesforyou
3 years ago
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A family gathering at a rented house leads to a mixup and mistaken bed partners

This story was written as an fantasy. The writer does not condone the described behavior in real life. My parents had rented a house for the week. My brother (the second oldest of four) was graduating from the academy and his wedding was planned to coincide. There was going to be a gathering of family, most staying at the rented house and just a few deciding to opt out for motels. We arrived at the house in the afternoon and were greeted by some of the celebrants who had arrived before us....

1 year ago
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LadyLifeRide30 continues

Lady-Life-Ride-3.0 continues... The weekend before school had been most educational for young Sean Masters. He'd spent the bulk of it familiarizing himself with the controls and abilities of he strange device he had found on the last day of work. Fortunately for him, his parents had relented a little bit and allowed him to have the last weekend of the summer to do with as he pleased. He'd gone out and played with his new toy. After a bit of trial and error he was feeling...

1 year ago
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The motel

Craig couldn't believe his luck! Buying the Sunny Day Motel had been the best decision of his life! He had gotten the idea to install hidden cameras in each room from one of those "Candid Camera" shows on television. Right from the beginning Craig knew that this little ten room motel could be a gold mine if it was run "properly"! After taking possession of the motel, Craig got down to the business of installing his hidden cameras and microphones in every unit, until by the time he was finished...

Voyeur
2 years ago
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The real man

Today i went to my best friends house and she did not answer the door so I went in to deliver the package for her. As i sat it on the table her husband came around the corner surprising me as I did not know he was home. the big surprise was he was naked and had the biggest cock I had ever seen. Jan had said he was hung but I had no idea it was this huge. He was double the size of any men I had been with. I could not take my eyes off it. He had no problem being naked with me. He told me Jan was...

2 years ago
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The Honey Dew ListChapter 15

Damien and Amos both found things to occupy their time, mostly in terms of Amos going over the details in a careful review of what information he gathered, especially in light of the bomb threat. He did his best to put anything romantic or sexual on the back burner for now, wanting to focus on work during his typical workday hours. He wasn’t honestly sure what to say or do about the bomb squad chief and his apparent interest in him. The guy was cute, not to mention brave and smart, but did...

3 years ago
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To Love and to Cherish

TO LOVE AND TO CHERISH ====================== Copyright C 1996, Daedalus This story contains what is known as "transgender material". It does *NOT* contain any elements of m/m, s/m, b/d, humiliation, pain, or anatomically detailed descriptions of sexual acts. If this lack offends you, do yourself a favour and read no further. All characters and situations described herein are fictional and any resemblance to any real or fictional persons or events is purely ...

2 years ago
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I Impregnate The Lactating Latina Wife of My Subordinate

My name is Matt and I work as a managing engineer for a large oil company in Houston. My wife Sandra and I are in our late-forties. Sandra works for a woman’s retail clothing store. We have become close family friends with one of my field engineers and his family. We provide a lot of emotional support for them since their real families live in the Boston area. Sandra and I live only ten minutes away in an adjacent suburb. The engineer’s name is Tommy and he is twenty-seven years old. His wife...

1 year ago
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No Visiting Hour Required

A crazy night at the hospital, no mor After doing chores that morning, Elsie was glad that she finally had her alone time. That day was unlike every ordinary day because it was Masturbation Saturday so she locked her room, unzipped her shorts and stripped her clothes off naked. She grabbed her laptop and went straight to her favorite porn site. When Elsie found the video that caught her eye, she plugged in her earphones and started to play the video. Feeling caressed, she gently started to...

Affair
4 years ago
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Deputy PorterChapter 139

"You really going to do it," Phil asked when I explain what Jim wanted. "Consider it my sacrifice for art," I said. There was no need to tell Phil and Jeff what all I had done for a lot worse reasons. My proclivity for sexual deviancy was admitted by me to me and me only. Phil and Jeff didn't need to know that I was more than just willing. To me the idea of it all was a huge turn on. "Since there was no time agreed to, stay around your place. If you go out anywhere, carry your cell...

4 years ago
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Husbands Humiliation

Husbands HumiliationLosing my job devastated me. All my life I'd learned that the man must support his family. Any man who can't be the breadwinner is not a man; he's a loser - beneath contempt. Being a stock broker only made this worse. I was used to pushing around lots of money, of being in total control over people's lives. Now I'd lost control of my own. I could push anyone around: a multi-national company, a millionaire client, my wife. For weeks, I woke up every morning wishing I could...

4 years ago
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Love At SDCC 2014

So I had recently got tickets to San Diego Comic-Con 2014, I got tickets for the Avengers:Age Of Ultron Panel in Hall H which was exciting because all the cast was going to be there as well newcomers Josh Brolin,James Spader,Aaron Taylor-Johnson and Elizabeth Olsen who was in skin tight gray dress also I was staying at the Adjacent Hotel the San Diego Hilton which was right next door to the Convention Center . The Panel was great we got insight and a teaser trailer on The next Blockbuster which...

2 years ago
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The Eighth Warden Book 3Chapter 9

Peregrine may not have been as large as the massive cargo carracks that formed the bulk of the Senshall fleet, but at over a hundred and fifty feet long, and thirty feet across at her widest point, she was still a big ship. And a busy ship. Corec had to wait his turn to ascend the ramp from the pier to the main deck, while the sailors ahead of him rolled a heavy barrel up the incline. When he made it to the deck, he greeted Boktar, who was crossing items off a checklist. “There was nothing...

2 years ago
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My First Gay BDSM encounter

Hi, I am Tejas. I am here to tell you about my first gay encounter with my best friend. Let’s begin with how I got I started watching porn when I was 18. Then after a couple of years later, I came to know about BDSM porn. I started loving it. I always liked the role of Master in BDSM the way the Master dominates. We all friends shared porn. But there was one friend. Let’s call him A, who also watched BDSM porn. As we had a similarity, we both became best friends. Whenever his mom and dad were...

Gay Male
4 years ago
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Wie ich mit der Intimrasur anfing meine Zeigegei

Schon seit ich Jugendlicher bin, hatte ich ein besonderes Verhältnis zur Nacktheit. Mit der Pubertät wurde ich mir bewusst, dass ich mit meiner Nacktheit auch meine Geschlechtsteile anderen Leuten zeige, und diese sich daran sexuell erregen. Ich selbst war ja auch begierig darauf, andere Leute nackt zu sehen und mir bei Frauen deren Brüste und Fötzchen, bei Männern ihr Glied und Hoden anzuschauen. Dass sich andere an meiner eigenen Nacktheit ergötzen und sich damit aufgeilen, wurde mir damit...

1 year ago
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An Encounter With Aunty

Hello readers, This is Rahul a new writer. coming to story this incident happened when I was in my 11 class we used to live in a shared apartment with another family there were 2 rooms one for our family and one for other and one common room connecting both room and here is this aunty named Sunita (name changed) she used to live with us in that apartment. she have very attractive athletic like body, round fleshy boobs and good round of ass she was like a athletic person , slim and perfect she...

3 years ago
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Lizzie Moving InChapter 8

Thursday Aug 11. The Rents woke me up this morning and not wanting to get on their bad side and have our plans disrupted I hurried to get ready and go down stairs for breakfast. I still can't believe that they're letting my friends sleep over Friday. I'm so excited! Emily and Tim wish they could too but they're parents have plans. They're hoping they can visit next weekend though. I hope they can. As we ate breakfast Grandpa pulled up in Henry. We went out to greet him and I gave him...

1 year ago
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Inviting a PickupChapter 4

Jake sat with his sisters and Kimmy at lunch on Friday, telling Kimmy he would be by to pick her up at 10:00 AM. She wondered what they were going to be doing all day but he just smiled. Jake had a day planned that he hoped she would enjoy. It would require a little travel, but he was looking forward to it. Saturday dawned bright and sunny, with temperatures expected to be in the upper 80's. It was a last gasp of summer before fall set in and perfect for Jake's plans. Jake picked Kimmy up...

3 years ago
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My Spanish teacher

It all began two years ago as I was 18yo. while attending high school.  Not too many people went to this private school in this town, so you would think it was not so much of high-quality,  but to tell you  the truth, it wasn’t to much popular,  not a well known school. The motive I had to attend to this school or institute was simple: I wasn’t a good apprentice at all, and needed some support, so I was forced to register at “Studying and Understanding Techniques,” a subject intended to back...

2 years ago
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Losing It AllChapter 3

Ressler stood on the river bank, seeing, but not really taking much notice of the river flowing by. It was cold, and the breeze tugged at his coat and ruffled his hair. He'd stood in this very spot twice just a few days ago. Both times he'd met with Reddington. And in between those two meetings with Red, his world had fallen apart as Audrey took a bullet meant for him. In the five days since he'd lost her – and perhaps his child - his emotions had run the full spectrum. The sheer panic...

2 years ago
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The GovernorChapter 10 The Pink Pussy

"Are you a jealous woman, Lucy?" Albert inquired. "I'm sorry, sir. I don't understand." Albert took a leisurely sip of his tea and he beckoned that Lucy move closer. Then he smiled; that oily, smarmy smile of a man that begs to be mistrusted, of a man dishonourable in matters of sex. He placed the cup on a waiting table, careful not to spill it. "There are many types of women, Lucy," he smiled broadly. "There are those who accept that men are licentious and filthy lechers, and...

2 years ago
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family FUCK

It was 1 A.M. and I was about to go to sleep but first I decided I was going to jack-off. I was home from college for summer break and it seemed in the only time I had to myself was in the middle of the night. My 19 year old sister and my parents seemed to constantly be knocking on my door asking various things. I pulled off my pants and boxers and sat at my computer. I turned on some porn and started stroking my cock as it stiffened to its 8 inch length. Normally, I close and lock my door...

2 years ago
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White wife cheating with BBC again in the woods

BBC Again!I was at the same gas station a couple of weeks after my encounter with Joseph and his buddy’s, when I saw him pulling in. I waved at him and he waved back and walked over to my pump. We said hi and began talking. He asked me if I enjoyed our last meeting and I said I did very much. Joseph reached into his pocket and pulled out a phone and handed it to me. I asked what it was and he said he had bought a pay per phone for me to get in touch with him when I wanted to, so hubby would not...

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