Timmy's Confession free porn video

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Timmy's Confession by Pamela ([email protected]) Harriet regarded her lingerie drawer. Her husband, John, was nearby in the bathroom brushing his teeth getting ready for bed. They had been out that evening at a dinner party with friends down the block. When they had gotten home their 10 year old son Timmy was sleeping peacefully in his bedroom. Ever since he had been eight they had felt OK to leave him without a sitter if they were just a few doors away in the neighborhood. It was a very safe community they lived in. There had been nothing amiss in the house when they had come home, except now, when Harriet had taken off her slip and had folded it neatly and was about to put it back in the dresser drawer. She noticed that something didn't seem right. The problem wasn't necessarily with her bras and panties which looked pretty much like she had left them. No, it was her slips. She could see that the top slip on the pile was not folded as neatly as she always folded them. She picked the slip up and let it open up. It had definitely not been folded correctly. Timmy must have touched it, there was no one else who could have. Probably some adolescent curiosity was creeping into him now that he was approaching puberty. Hopefully this would be a one time event and she had better not get worked up about it - though she didn't like the thought of her son poking around in her lingerie drawer. *** Three weeks later the incident was out of her mind when she came home after a bridge night with other neighborhood friends, to discover that her dresser drawer was not fully shut. It was just a tiny bit ajar, but she was more than a little bit obsessive about shutting drawers so she didn't think she could have left it open. She looked inside the drawer and saw that her bras may have been touched and so too her panties and slips. "Damn," she thought, "that Timmy is getting out of hand." She then opened the closet to put away her dress and noticed that a pink, cotton sundress that she rarely wore was hanging a bit askew on its hanger. Harriet sat down on her bed in a state of shock. John walked into the bedroom and asked her what the matter was. Harriet shook her head and told him "nothing," it was just her stomach that felt a little bit flippy floppy. "I hope you aren't getting sick," he said. "Oh no, it's already passed," she said. She had decided that she had better not tell John. Surely he would wake up Timmy in a tirade of anger. It would be too ugly. She would have to handle this herself. *** That week Harriet went to an electronics store and bought a tiny wireless spy camera and had the salesman explain to her five times exactly how it was to be used; especially how to record and send the video to her computer. Later that week, while John was at work and Timmy was at school she set up the camera on the top of a picture frame in her bedroom so it had a sweeping view of her bed and dresser. It's not spying she said to herself, not like it would be if she put it in Timmy's room. She hoped against hope that the camera would not turn up anything of interest. The first opportunity she had to catch Timmy in the act of invading the privacy of her bedroom and clothes was that Tuesday. Every Tuesday and Thursday Harriet worked part time at the local school district in the central offices until five in the afternoon. On those days Timmy let himself in after school at three and was alone until either Harriet or her husband came home. Before she left for work that day, Harriet turned the camera on and set the timer to begin recording at three. When she came home from work that day, fearful of being caught either by her husband or Timmy, she made no attempt to look at the video. Instead, she waited until the next morning after Timmy left for school and John had gone to work and the house was empty. She turned on her computer and began playing back the video file. For 15 minutes she watched a fixed view of the room and then suddenly the bedroom door opened and Timmy, naked, tiptoed into the room. She heard him say "mom?" as if double checking that she wasn't somewhere lurking in the shadows. She hadn't seen him naked for a half dozen years and her heart tensed with affection for the thin little figure she saw. His penis was a tiny little thing and she watched as he walked to her dresser. He opened her bra and panty drawer and she watched in a state of disbelief as his body tensed and seemed to convey a degree of excitement equal to that if he were to have opened a long lost chest of pirate gold. He used one hand to lift up the top few bras and with the other took out a pink bra. It was her only pink bra - actually she hadn't worn it for years. It was a bra she had gotten when she was younger and worried about being sexy. Now she preferred more functional bras that were more comfortable to wear. The pink bra was a bit tight on her, her breasts had filled out a little with age. If she remembered correctly the bra probably had a B cup, not the C she wore now. She watched as her son almost comically put on the bra. He clearly had no clue how to do it correctly. Once he had it on she saw him take panties and very carefully stuff them into the cups. Next he took out a panty from the very bottom of the pile and put it on. It was a faded pink and almost a rag. His little penis pushed ever so slightly against the nylon fabric. Abruptly, Timmy closed the drawer and opened the one below. She wondered what he would do with her hosiery drawer, put on pantyhose? Instead, he took out an old girdle of hers. She had even forgotten she still owned it. It had a shiny satin front panel in a sort of diamond shape and an open leg style with a side zipper and a set of three garters on each leg. Timmy slipped into it, zipped up the side, and then lay down on the bed. He lay there quietly without moving and she watched his face as it softened and relaxed. He crossed his arms across his chest below the bra. He looked like a thin, gentle little girl wearing her mommy's clothes. Harriet felt herself tearing up and becoming deeply sad. She had expected to see Timmy masturbating but he didn't. He just lay there looking blissful and then also forlorn. The full impact of the scene slowly dawned on her. Timmy wasn't raiding her drawers for a sexual thrill. No, he was pretending to be a girl. After awhile Timmy got up and went to the closet. He put on the pink sundress and lay down again on the bed Harriet watched as Timmy began crying. Tears rolled down his cheeks. He suddenly got up and got a tissue and went back to lying on the bed. Even though he was crying a bit he looked blissful. It was heartbreaking to watch. After awhile Timmy seemed to be having a dialogue with an imaginary person. His arms moved in a delicate, graceful fashion. He had very pretty hands she thought. Girl hands. Harriet wondered what she ought to do. Clearly Timmy was getting very careless. Maybe he even wanted to be found out. But his father would become a force of nature if he knew what she was witnessing. He would never understand. God knows what he would do. Timmy got up and kneeled next to the bed and formed his hands in prayer. She had a view of his back in his dress and if she hadn't known better she could have mistaken him for a girl. In his tiny voice she heard him say, "please God make me a girl. Please, please, please. I'll do anything. Please God. Just this one little thing." Timmy dabbed at his eyes with the tissue and blew his nose. He got up and lay down again on the bed and Harriet heard him sobbing. In a few minutes he looked at the clock on the nightstand and got up again. He removed the dress and put it back in the closet and then did the same with the lingerie. She saw him double check that everything was back in its place and then he exited the bedroom. Harriet got a tissue herself and dabbed at her eyes and blew her nose. She thought back to how she had raised Timmy. It was true that she had felt a twinge of disappointment when she had given birth to a boy. She had been so convinced her baby was going to be a girl that it was a shock to find out she was wrong. However, when she had first held Timmy she couldn't have been happier that God had sent her a little boy. Perhaps she unintentionally raised Timmy to feel like a girl, but if she had done so she couldn't for the life of her see how she had done it. John was a fully engaged dad. He was good with Timmy, played with him often. They did occasional dad/son activities - things that mainly only guys did. Timmy was not a momma's boy though she had always felt that he was on the sensitive side of things. Sometimes it seemed like he cried too easily like some girls did, but it had never been a real problem. *** Over the next few days Harriet pretended in her dealing with her husband and Timmy that all was well. She bent over backwards to seem happy and relaxed while inside she felt a terrible, suffocating helplessness. She didn't do anything to prevent Timmy from invading her clothes. She worried that if she was to tip him off about knowing what he was doing, then she would be stuck with a problem she didn't know how to handle. The consequences of confronting him could unalterably change her relationship with him and she could not stand the thought of that happening. She also worried that getting caught in such an intimate misdeed by his mother could lead Timmy to a lifetime of trauma. A week went by and finally, in desperation, she arranged to have lunch with her sister, Ruth, who was a couple of years younger, childless and single. Ruth was a career woman in the fashion industry and she and Timmy had a special bond that was only possible because Ruth wasn't his parent. Ruth was very fond of Timmy and Timmy looked up to her. Over lunch at a chic restaurant in town, Harriet said, "I asked you here for a purpose. You see I have a problem." "You know I'll help any way I can. Is it with John?" "No, no, it's with Timmy." "Timmy!" Ruth's face which had formed into a frown in anticipation of hearing that John had been cheating on her sister now turned to one of genuine worry and concern. "What's the matter?" she asked, fearing for the worst. She couldn't imagine that Timmy would be a drug taker, or misbehave at school. She wondered if he had come down with a terrible illness. "You have to swear to not tell anyone anything I say here. Especially John and certainly not Timmy!" "Sure Harriet. You know I never would betray your trust." "Good. Well, you see, I've discovered that Timmy dresses up in my clothes. My bras, my slips, my panties and a dress. Even my old girdle." She went on to describe the initial evidence and then about the camera and Timmy's prayers. Ruth listened with her mouth agape, every so often saying, "oh my!" Harriet had fought back tears as she spoke and Ruth reached out across the table and held her sister's hand. "I haven't confronted him or even done anything like lock my bedroom door. I didn't want to get John involved or cause Timmy to freak out. So what can I do? What should I do?," Harriet said. "Oh my gosh," Ruth said, "I need to think, it's so surprising. I thought you were going to say he was sick or something. Well, I guess I agree that you don't want to tell John. Bless his heart, I doubt if he could be at all helpful in this situation." Ruth was thinking what advice she ought to give. She imagined Timmy in a bra and girdle and dress. Girdles were so uncomfortable, but if you wanted to be feminine she supposed it was right on up there with a bra. "I guess we have to believe that what he was praying to God about is true. He sees himself as a girl. From what I understand he'll probably always feel that way. It's indelible. I don't want to make you cry again but I think you have to accept this truth the same as if he grew a third arm. Denial or ignoring it will not help, but I agree that confronting him might not be the best thing to do. It's probably a good idea if he can be coaxed into taking control of his own situation." "How can we do that?" "That's a good question. He needs to tell you on his own free will that he's been sneaking around in your drawers and why. That's exactly it! We need a confession. It would take him from being just a naughty kid, that John would clobber if he found out, to a kid who is looking to his parents for help with a problem. I mean I don't think that John would kill him if Timmy confessed to him his desire to be a girl. Would he?" "You're right. Even if he did initially get mad, he'd soon see he was wrong and apologize. I give that much credit to John." Ruth scrunched up her face in thought and then said, "but perhaps that's going too fast. Maybe just a confession to you would be a good start. I can't imagine Timmy standing in front of John telling him he was a girl, but with you I could see it." "But then what?" "We could see how this goes and then make up a new plan later. For the moment you want to stop him from raiding your clothes and you want to do it with the least trauma. That says that we need to leave John out of it for the time being with good justification. So the problem becomes how could we get Timmy to confess to you?" "Someone else would have to convince him to tell me what he was doing," Harriet said. "Exactly," Ruth said. "You could let me discover him cross dressing. It would be a bit traumatic for him, but much much safer, nothing as bad as having you find out." "But it could ruin your relationship with him." "I don't think so. It might even draw us in closer, particularly if he saw that I wasn't condemning him, just trying to set him on an honest path. It could help him to maintain his self-respect throughout this ordeal." "OK, but how could we do it? You can't barge in on him at my house." "Maybe you and John could take that little jaunt to Puerto Vallarta you always talk about to reenact your honeymoon and I'll watch Timmy at my place. It seems like a safe bet that he'll invade my lingerie drawer if I'm at work and I'll try and catch him in my bedroom by coming home early." "And then what?" "Then we can have the big conversation in which he tells me the whole story of his cross dressing and wanting to be a girl. I'll tell him he has two choices: if he intends to cross-dress again, then before he does so, he has to first confess to you his desire. If he doesn't ever cross- dress again, then he doesn't have to say anything and I'll promise to keep it a secret forever." "But we know he won't or can't stop." "So we can be pretty sure that he'll end up confessing his desire to you and then you can make sure that he doesn't go into your dresser drawer." The two ladies thought about the plan and discussed it further. "I think it's a great plan Harriet, because it will get you involved in a positive way, on his side. It gives you some control." "I agree," Harriet said. "So instead of me confronting him, he'll never know that I know what he's doing and he'll eventually come to me with his problem. That sounds great. I'll talk to John tonight and see if we can get away soon." *** A few weeks later with Harriet and John away on their second honeymoon, Timmy moved in with his Aunt Ruth. It was the spring break at school and Ruth planned to take a day or two off from her job to be with Timmy. He came on Saturday and over the weekend they did many fun things together like visit museums and shopping and even went to movies they could both enjoy at the Cineplex. To outward appearances Ruth could find nothing about Timmy out of the ordinary. In fact, their mutual fondness for each other made for a delightful easygoing time. Ruth stayed home from work on Monday morning and at lunch time said she had to go into the office for the afternoon to take care of some important business. She expected to be home at 5 in time to make dinner. Timmy assured her, a bit too eagerly she thought, that he would be fine being alone by himself. She had to laugh to herself thinking what kind of entertainment he probably had in mind. Ruth left the apartment and went to work. She knew she would feel better in the long run if she didn't have to lie about having been at work that day. At 3PM, two hours earlier than she had said, she headed back home to see what she might see. The reality of sneaking in on Timmy was much harder than her fantasy about what it would be like. The fact of the matter was that she was so fond of him, it was painful to contemplate the embarassment she would cause him by catching him in the act. But she had to do it since it would be better in the long run for Timmy than to do nothing. She quietly entered the apartment and looked around. Timmy was not in sight and everything looked pristine, just as she had left it. Her bedroom and the guest room where Timmy was staying were across a carpeted hallway from each other. Ruth tiptoed through the apartment toward the hallway. When she got to the door of her bedroom she saw that it was part way ajar even though she had made sure to close it before she had left. This was exactly what she imagined she was going to find. Her plan now was to call out to Timmy as if she expected to find him in his bedroom while simultaneously entering her own. That way she would look completely innocent of having snuck in to catch him. She braced herself for what she might find in her room. She counted to three and then pushed open her door, backing in and calling out "Timmy?" She heard a shriek behind her and as she rapidly swiveled around she was just in time to see Timmy spread out on the bed wearing her bra and panties. He leapt up, arms flailing in the air as if to block her view and ended up crouching on the floor next to the bed in a fetal position. He sobbed and wailed uncontrollably and struggled to get the bra off. She noticed that one of her prettiest slips was lying on the bed nearby. "My God Timmy, I wasn't feeling so good so I came home early. How could you do this? How could you sneak into my bedroom and open my drawers and wear my clothes?" Timmy managed to take off the clothes. He put them on the bed while hiding his nakedness. "I'm sorry, Aunt Ruth!" he wailed. She picked up the bra, it was one of her everyday bras. The panty was light blue with several rows of ruffles across the bottom. It had once been part of a Halloween costume. "I'm putting my clothes back in my dresser. I'll turn my back and you can run back to your room and get dressed. Then I want to meet with you in the living room!" She said this with as stern a voice as she could muster. Timmy hurriedly got up to do as she ordered and as he did so he said, "are you going to tell my mom and dad?" "Maybe," Ruth said, "but first I want to talk to you, so get dressed." *** A few minutes later Ruth and Timmy were sitting together in the living room. Timmy had a fistful of Kleenex in his hand. Ruth couldn't recall ever seeing the boy in such a miserable state. "Look, Timmy, if the truth be known, I'm more upset at catching you sneaking around in my personal property than I am about you wearing a bra and panties," she said, "not that I'm wildly happy about that either." Timmy seemed like he was trying to form some words but instead went into a new convulsion of crying and blew his nose. Some snot dangled between his tissue and nose and his eyes were bright red from crying. "I don't know why you want to wear my bra, you're a boy aren't you? But the thought of you sneaking around in my clothes is very disappointing to me. It doesn't seem like the Timmy I know and have always loved. What is that all about?" Timmy calmed down enough to say, "I know I'm gross and disgusting." "You're saying that to stop me from punishing you, aren't you?" "No!" he shrieked. "OK, Timmy, I really want to talk to you about this, not just punish you. So tell me why you did it." "I don't know why I did it." "You'll have to do a lot better than that," Ruth said sternly. She wasn't going to let him off the hook easily. "Start with why you snuck into my room." "I guess I thought that if I just borrowed your clothes for an hour and put them back that you wouldn't notice." "OK, I can figure that part out myself. But what made you think to do it in the first place. The first moment alone from me and all of a sudden, boom!, you're right into my clothes." "I just was curious," Timmy said. "Curious? Look, young man, I'm expecting a lot better answers than that," Ruth said. "We're not going to leave this room until you explain why. And if I'm not happy with your explanation, I'll definitely have to tell your parents. For all I know you sneak into your mom's bedroom also." She was being harsher than she really wanted, but couldn't let him do a Ronald Reagan on her. After sniffling quietly for several minutes, Timmy said hoarsely, "can I tell you something you'll never tell anyone else?" "I suppose so. Sure, I won't tell anyone." "Well, I remember once a few years ago seeing my mom wearing a bra. She was in her underwear." Timmy paused and seemed to be fighting back tears again. "Go on," Ruth said. "I don't know, later that night I was going to bed. I was lying there and I remembered what I had seen and I thought that I should probably have to wear a bra also. Just like my mom. But I know its gross and I will never do it anymore." "Wait, wait, back up, Timmy, and enough about it being gross! So what did you do?" "I thought about it." Timmy became silent. "So today was the first day you finally decided to wear a bra?" Timmy began crying in earnest again and Ruth said gently, "be honest Timmy and I promise you that everything will end up being all right." Timmy blew his nose and Ruth continued, "so, have you ever done what you did here anywhere else?" Ruth asked. "I've done this a few times with my mom's clothes." "With your mom's clothes?" "When she and my dad were out. I couldn't stop myself." "Sneaking around in your mom's personal clothes cannot be nice!" Ruth smiled inwardly. This had been so much easier than she had thought possible. A full confession and she was sure that one day Timmy would be admitting the same things to Harriet. "I know. I've felt badly about it, but I couldn't stop myself. Like today, I tried to stop myself, but then the thought that I could be so happy made me do it and I told myself that if you didn't know I was wearing your bra and panties it wouldn't really hurt you." "Like if, suppose somebody borrowed your bicycle without asking you and returned it before you knew it was gone. Would that bother you?" "Yeah." "Why?" "Because they might hurt it." "Yes. They put your things at risk without your permission to do so. In the case of my underwear, it's the most intimate part of a person and I feel like your violating my most private space." Timmy fought back more tears and grew silent. "Will you do it anymore?" "No, no, like I said, I won't." Timmy said and as he did so he felt a state of panic overtaking him. He loved his mom's clothes. He loved her panties and bras and especially her slips. And that wonderful pink sun dress. Lying in bed dressed like that was the happiest he had ever been and he couldn't imagine not allowing himself to be that happy again. "Won't do what?" "I won't wear your clothes or my mom's clothes anymore." "But what about wearing ladies clothes?" Ruth asked knowing that this was the far bigger issue to get into. "Oh, I mean I also won't wear girl's clothes anymore," Timmy said. Ruth regarded him tenderly. That was certainly a promise he would never be able to keep, but it provided the perfect opportunity to spring the trap she had worked out with Harriet. "I'm willing to not say anything to your mom and dad about what you did today so long as you promise me one thing." "What's that?" Timmy asked with some hope. "That if you ever find yourself not being able to stop yourself from wearing ladies clothes again, then you will first have a talk with your mom about it." "But I'm never going to do it again." "I know you said that Timmy, but I still want you to make this promise to me. Is it agreed?" "You don't believe me!" Timmy said. "I believe you Timmy, but how you feel today might not be how you feel tomorrow. So, let me ask you again: if you do want to dress up as a girl in the future do you promise to ask your mom first?" "Yes," Timmy said. "And you won't be sneaking into your mom's or my clothes or any other ladies clothes any more?" "No, I won't." "Good then my lips are sealed. I won't tell your mom anything that happened here today." Ruth smiled at Timmy who still looked utterly miserable. "Let's not let this incident get in the way of our having a good time this week," Ruth said, "in fact let's go out to dinner tonight!" Timmy looked depressed and still afraid to look her in the eye, but he attempted to make a slight smile and said, "OK." It had to have been a deeply traumatic experience for him, and now he had to go through his mother to get to wear girl's clothes. Perhaps it would prove to be a big enough obstacle to stop his behavior for a few weeks or even months, who knew. Thankfully at least Harriet would now have the chance to take control of the situation once it developed and that beat a blank as they say. *** Timmy and Ruth still had better part of a week to spend with each other, and though initially awkward, within a day or two they returned back to their usual relationship. At dinner one night, feeling a bit encouraged Ruth said, "I just wanted to say that I hope you know that I love you very much." "I love you too Aunt Ruth," Timmy said. "I'm glad. I want you to know that whatever happens in the future you should know that I'll be there for you. I'll provide a sympathetic ear." "You're not mad about my ..." "No, definitely. Please. It's not easy growing up, finding ones way, and I understand that. No one is free from errors of judgment or mistakes that they have to learn from. You're a wonderful boy Timmy. I couldn't imagine a nicer nephew to have." Both she and Timmy became a bit choked up. "As far as what happened here I won't say anything to your parents, but like we agreed to, you should talk to your mother about your feelings in case you get those desires again." "I don't think I'll ever have to but if I do I promise I'll talk to her. But don't you think she'll get mad or cry or something?" "Your mother loves you very much. It's as close to unconditional love as love can be. Whatever you say, as long as you're honest she'll be happy to know that you confide in her and she'll try her best to do what's right." There was a lull in the conversation while Ruth assumed that Timmy was thinking whether or not his mom would think that it was "right" for him to dress like a girl. "Do you believe in God, Aunt Ruth?" Timmy said, startling Ruth. "Why, I suppose so, sort of." In truth she said what she said so as not to prejudice whatever Timmy was about to say. "Why do you ask?" "Sometimes I wonder about God watching me do things, like what I did you know in your bedroom." "I think it's what is usually called your conscience. That's the idea that we try to do the right thing because we're watching ourselves and we don't feel good if we do bad things." Seeing that Timmy was perplexed she said, "it means that you have to think about what you do, not just let God do all the watching and thinking." She hoped that he would think about this the next time he wanted to dress up as a girl. "But sometimes it may be that I think it's OK and God doesn't. Or what if God wasn't watching what happened?" Ruth wondered what he was driving at. "I guess there are times when it's hard to figure out what is right and wrong." "And maybe God can make mistakes and then a person could do something that looked to be wrong but was really right?" Ruth wondered what powerful forces were bubbling up through Timmy's inner soul. She felt sorry for Timmy that he had to come to terms with who he was in a world where people had to be very much concerned with what others thought about them. At his age it was even more difficult to be one's self. On top of that her poor sister Harriet was going to have to end up with this entire problem in her lap one day. It was a question of when and not if. That, perhaps depressing news, was what she would have to report to her sister when she got back from her trip. *** The day after she returned from her marvelous vacation with John, Harriet met with Ruth and got a complete accounting of what had transpired. The two women were more convinced than ever that they had done the right thing thus far. Harriet was unhappy to hear that Timmy had invaded Ruth's private space, but glad that at least his predilection to wear girl's clothes was out in the open. The next big step in their plan was to await Timmy's confession if it should come. The two women discussed what options they had when the time came to respond to Timmy, and left a final decision as to what to do until such time as it might be needed. At first, Harriet expected Timmy to present himself to her with his confession at any moment and she felt tense and irritable awaiting it. Happily, the video camera showed that Timmy had definitely stopped going into her room when she was gone, except one time when he entered, stood in front of the dresser and then left. It saddened her to see the agitated expression on his face but she was also glad that he had enough courage to control his impulses. Another week went by and Harriet was thinking less often about Timmy and thinking that maybe he would never bring up the subject of his cross- dressing. She and John had gone out to play bridge and when she came home she had turned on her cell phone to see there was a text message from Ruth saying it was urgent that she call her. While John was getting ready for bed, she snuck down to the kitchen and did so. "Timmy called me this evening," Ruth said. "Really?" "Yes, he asked me if he really has to talk to you about wearing girls clothes." "What did you say?" "Well first I asked what happened, since the last time we talked he was so convinced he would never want to wear girl's clothes again." "What did he say?" "He said that he was going crazy. He was sure that he was really a girl. He couldn't see not dressing like a girl. I told him that it was good that he had reached a clear vision of himself but that he definitely had to live up to his end of the agreement. He sounded a bit depressed but also resigned to what he had to do. So I just wanted to give you a heads up. I think he might try and talk to you tomorrow." "Thanks dear. You've been a big help." *** Harriet passed a restless night worrying about what she would say to Timmy. The best idea she and Ruth had worked out was to give him some clothes and a restricted time when he could wear them. They definitely agreed that it was not a good idea to refuse him the opportunity. The next day when Timmy came home from school he was terribly distraught. He was on the verge of crying and Harriet braced herself for whatever it was that he was going to say. "What's the matter honey?" she said with some alarm. She had decided that without doubt she would never give Timmy any hint that she already knew about what it was he would want to confess to her. Besides making him lose trust in Ruth she wanted to give him every opportunity to find himself, to find for himself what he needed to do. It was a very tall order for a ten year old, but in her heart she felt this would create a foundation of strength in him that would enable him to weather whatever storms were to come to him later in his life. "Mom," he said with a tremulous voice. The misery, fear, hopelessness in his voice rent her heart into pieces. "What happened Timmy?" Harriet said trying to sound like she would normally sound in such an instance, "were you sent to the principal's office!" "No!" Timmy said. "Come sit with me," Harriet said as she sat down on the sofa and indicated the spot next to her. "Whatever has made you so upset!" Timmy sat down next to her, then got up and got a few tissues and came back. He blew his nose. "I have to say something. I guess its sort of a confession." "A confession?" Harriet said soothingly. She knew what was coming. It had to be very hard for Timmy and it was definitely going to be hard on herself. Timmy looked at his mom. His face was so distraught Harriet wondered if her leaving it up to him to broach this subject had been a good idea after all. "You won't tell anyone?" Timmy said. "Of course not Honey," Harriet said, "confessions are private." Timmy hesitated a moment and then said, "I went in your bedroom a couple of times when you weren't home." Timmy fell silent and Harriet wondered if that was going to be it, but just as she was about to ask him if that was the confession he said, "I opened your drawer." "Which drawer?" Harriet asked. "The one in the dresser, where you keep..." His voice had gotten husky and he began to cry. "Where I keep what?" Harriet said. She had decided to play as dumb as possible. "You know your lady stuff." "You mean my blouses?" She kept them in the bottom drawer of the dresser. "I mean where you keep your underwear." The last part of the sentence was barely audible. "You mean you looked in my underwear drawer where I keep my bras and panties?" Timmy shook his head up and down and through his tears said, "yeah, but I also touched your stuff." "Touched?" "Put some on." "You wore my bra and panties?" "Yeah," Timmy said and lapsed into a crying fit. "Why are you telling me this?" "Because, Aunt Ruth ..." "Aunt Ruth? What has she got to do with this?" "Mom! She caught me doing the same thing at her house and she said..." "Wait a minute!" Harriet said. "The same thing?" "Yeah I was wearing her bra and panties and she came home early and ..." "She told you to confess what you had done?" "Well, actually, I told her that I had worn your bra and panties too. And she said that I wouldn't have to confess if I promised I would never do it again." "So you did do it again?" "No, I didn't but mommy..." Timmy started to cry with large upheavals of air coming and going from his lungs. "Calm down," Harriet said and she put her hand on his slight shoulders and pulled him toward her so his head was in her lap. She looked down at him as he struggled to regain control of himself. It was so hard to find oneself she thought. What can a parent do, it was something everyone had to do for themselves. "You need to tell me why you wore my and your aunt's bras and panties." There was a long moment of silence and she felt Timmy's breathing becoming more regular. He was a very attractive child and maybe she had never noticed that he did have some feminine traits. His skin was soft and delicate like a girl and of course the silky smoothness of his straight blonde hair. His arms were also thin and undeveloped like that of a girl. Finally Timmy said, "Mommy?" "Yes?" "Do you think that God could make a mistake?" Harriet felt a wave of tears hit her own eyes. "What kind of mistake?" she asked. "Maybe there was a little girl that He was creating and then by accident she ended up being a boy?" With all her self-control not to breakdown Harriet said, "is that little girl you?" "Yes, mommy." Harriet stroked his head and she let some tears come down her own cheeks. "I guess God could make a mistake, but maybe it's just that God makes some people very very special. People that can be both girls and boys at the same time." She could sense that Timmy was thinking intensely about what she had said. "How can someone be both a girl and a boy?" he said. "When you put on my bra and panty did you feel like a girl?" "Yes. Mommy, I also wore your slip and your dress. Your pink dress and..." "and they made you feel like a girl." "They make me feel happy. They make me feel like I don't know, it's just that I know I want to feel that way all the time. I don't want to be a boy." "Is it you don't want to be a boy or is it that you want to be a girl?" "I think it's that I feel I am a girl and that's why I don't want to be a boy. I don't want to look like a boy since I don't think I am one." Harriet felt exhausted. Where should she go from here? It was not obvious to her. Can she condone this and even if she did how much must she be a part of Timmy's life? After awhile her mind cleared a bit and she said, "you've not yet told me why you're confessing. If you haven't done it again, why confess?" "I promised Aunt Ruth that if I wanted to wear a bra again that I should confess. I mean I promised that I'll never sneak into your clothes again but I want to wear a bra. So what can I do?" He turned on his back and was looking up at Harriet. She looked down at him. She had all the power right now. His fate hung on what she decided to do. She hadn't held him in this position since she last breast fed him. It had been a wonderful pregnancy and she had loved being a new mother. The connection she had felt as Timmy suckled her was some of the happiest times of her life. From time to time she wondered if maybe she would have preferred having a girl if just for the reason that they could have intimate talks about girl stuff. She had even thought sometimes that John would always have a slight advantage over her since there would be times when he and Timmy could have man to man talks that she could not be part of. But now Timmy had upended the cart. Should she force him to be a boy or should she help him to be a girl? Could she force him to be a boy even if she wanted to? "So the problem is that you won't sneak into my room any more but you still want to wear my bras and panties?" "It doesn't have to be yours." "You just want to wear bras and panties, it doesn't matter whose they are?" "I feel like a girl mommy and if I can dress like a girl then I'll feel better." She stroked his forehead. How tortured he must be inside that he risked everything by confessing. "I need time to think about this. You know your dad has to be involved in this." "Don't tell dad!" Timmy cried out with fear and sat up. "How can I not tell him?" "You promised that you wouldn't tell anyone about this." "Yes, I won't, but it's a separate issue as to whether or not you can wear girl's clothes here. You're asking me to approve that without your father knowing about it. Is that fair to your father?" "Then I won't do it mom, so you won't have to ask him." Of course she wasn't really planning on telling John and that was one of the biggest parts of her dilemma. It was easier to go along with Timmy and give him a bra than to let John in on the secret, even though she hated the idea of having a marriage where she kept secrets from her husband. Either way she figured John would get hurt. Perhaps there was less pain involved in the long run if she kept him in the dark. Timmy was her son, her own flesh and blood and why should he suffer needlessly for something as silly as a bra. It seemed wrong to her. "I'm not planning to talk to your dad, but I need some time to think about this little talk. You'll have to wait for an answer. I'm sorry." Timmy looked confused, it wasn't what he was expecting. He lived in a world of instant gratification. He felt tears coming on again. Harriet said, "the good news is that I haven't said no, so you might as well not be sad." "OK, mommy, thank you," Timmy said. "You don't have to thank me," Harriet said. *** A few days later Harriet met Ruth for lunch and related to her what had happened. "What should I do?" she asked Ruth. "Whether or not you should aid and abet the enemy?" "Exactly, as well as risk John's eternal anger at me and maybe Timmy." "I've done some reading about this," Ruth said, "and I think its true that Timmy will for the rest of his life long to be a girl. It's never going to go away. So that's a reality that I think helps ease the problem." "How so? It seems like it means that there is no way out." "What I mean is that it doesn't matter if you give Timmy access to bras or not. He's going to always want them. He won't want them more or less because you gave him one. It's like worrying about whether or not morphine can turn the terminally ill into addicts." "That's a ghastly analogy Ruth but I see your point. If I help make Timmy happier that's the only effect of my helping him. I haven't really corrupted him." "Exactly my way of thinking. And it provides some cover against John if he ever finds out about it." "But John will believe that it's just a matter of self-control for Timmy." "You can tell John that you couldn't stand the thought that he would think less of his son, so you kept it from him knowing that it was futile to prevent it." "John will still get mad." "Your fall back position is that you love them both very much and you did the one thing that was sure to keep them both loving you. If you told John, his reaction to Timmy would cause you to think less of him besides causing Timmy to think less of both of you. So its win-win vs. lose-lose. Take your pick." "John will be mad because he'll think that he could have changed Timmy." "But you'll be able to point out how happy Timmy has been with the freedom to dress like a girl, besides the fact that John hadn't even been suspicious it was going on." "What would I do without you Ruth?" "That's what sisters are for. I love Timmy also and I love you and I sincerely think that it's also best for John." "OK. What kind of clothes should I get for Timmy?" "It's probably best if you work that out with Timmy," Ruth said. "I'm sure you're right." *** The next opportunity to be alone with Timmy, Harriet gave him her answer. "I've had some time to think about your confession and I've decided that I'm not going to stop you from pretending to be a girl if that's what you want." Timmy, who had looked terribly nervous broke out into a big smile and hugged his mother. "There are some important rules however. First and foremost is that you must never ever dress as a girl with your father in the house, or about to come home or any other circumstance where he could catch you." Timmy nodded his head up and down excitedly. "The second condition is that you can only dress like a girl in the house. Never outside." "Thank you mom!" "Do you agree to the conditions?" "Yes mommy, I'll never dress as a girl when daddy is home or about to come home and I'll never dress as a girl outside the house." "Good. So this is how it's going to be. We'll sit down at the computer and we'll do some shopping on line and have the clothes sent here. When they arrive you'll keep them hidden in your room." Timmy started to cry with joy and buried his face in his mom's neck and held her as tightly as he could. "We'll keep your girl clothes in the old trunk in the back of your closet and pretend, if anybody else should open it and ask why there are girl's clothes inside, that the clothes were left there for us to hold by Mrs. Milbauer your nursery school teacher - but she never came to get them." Timmy looked so blissful Harriet felt increasingly confident that she was doing the right thing. "When can we pick out some clothes?" Timmy asked. "How about right now?" Harriet said, and she fetched her laptop computer and brought it to where they were sitting. "I wonder what a good site is for girl's clothes," Timmy asked. "How about we look around at J.C. Penny, they have a good selection, and we've bought you jeans there before." Timmy put his thin arms around his mom and hugged her. Harriet felt a joy in her heart as powerful as the day Timmy was born. In some ways, this afternoon marked a second birth for Timmy. He could be counted upon to ever more deeply enter into his girl self and as he did so, Harriet would acquire a daughter. As they waited for the machine to power up and make the wireless connection, she also felt a sudden sense of foreboding. Perhaps she was crazy for not remembering first and foremost that this plan was terribly fraught with danger. Timmy might get caught by his dad wearing girl's clothes, or he might accidentally act the part of a girl in front of his dad. She would have to be ever vigilant, a thought that made her question the folly of what she was about to do. When the J. C. Penny website came up, Harriet said, "let's see where we should look." On the top they saw "Women" "Lingerie" "Juniors" and to the right "kids + baby". Harriet said, "I'm looking for girls. You're too young for "Juniors" so I suppose it must be in "kids + baby". Timmy looked on with complete absorption. Harriet clicked on "kids + baby" and saw on the left "girls clothing" and clicked on that. Some pictures of different categories of clothes came up that gave them a choice of directions to go. Timmy saw that one of them said "dresses" and had a picture of a bright pink dress. He couldn't wait to see if his mom would buy that dress for him. "Let's start with "underwear"," his mother said and she clicked on an icon of some gaily colored panties. Icons of bras, panties and socks came up . "We might as well first start with bras," she said and she clicked on "bras." Timmy was in a state of ecstasy when he saw the selection that appeared. The first was called "Maidenform 2 Pack Beginner Bras" for $12.00. They were pink and white and Timmy reflexively squeezed his mothers arm when she said, "oh, these are very pretty! Would you like a package of these bras?" "Yes mom!" he said. "We need to decide on a size." "How do you do that mom?" "I'll get a tape measure and see how big you are around the chest," Harriet said and got up and went to get one from her sewing kit. Timmy looked at the other choices for bras. One of them looked to be for older girls, anyway, it looked like the bra he had worn at Aunt Ruth's house. It was called "Maidenform One Fab Fit Bra." When Harriet came back she had Timmy take off his shirt. She then encircled his chest with the tape measure and read off "29, 29 and a half inches." That means that your bra strap size would be 30. "30?" Timmy said. "You always round up to the next even number. Like I'm a 36 but if you measured me I'd be a 35 or so." Harriet was enjoying herself and she made a mental note to tell Ruth about this experience when she got the chance. Talking to Timmy about bras reminded her of the kind of conversation she would have wished to have had with a daughter, if she had had one. Harriet clicked on size and selected 30. Below that was a button to select a color that revealed there was a choice between white and white, or pink and white. "How about the pink and white bra, it's a little bit prettier," she said. "OK," Timmy said. "It's so funny, they don't even ask for a cup size. It's just 30, since they know girls wearing a beginner bra don't really have a cup size." Timmy looked confused and Harriet explained, "it's not just the distance around the chest, it's also the size of the you know whats that go inside the bra. The cup size reflects how big they are. A is the smallest cup usually, then there is B and C and even larger ones for the really big girls. Like here, you see this other bra," she said indicating the Maidenform One Fab Fit bra, and she clicked on that. "See, if we click on 30 for the size then it asks us to enter a cup size. Here, it shows only the one cup size A since this bra is really just for young girls. They don't even make it in larger cup sizes." Timmy was looking at it with such intensity that Harriet said, "would you like one of these too?" "Can I?" Timmy said. "Sure, dear, but we have to choose a color for it, black, nude, pink or white?" "What do you think I should get?" Timmy asked. "How about we just get you a white one and a pink one?" "Great, mom," Timmy said appreciatively. "So we'll have four bras altogether, and now we'll look at panties." Harriet's mind raced along imagining what her relationship with Timmy would be like once his girl clothes arrived. She would definitely have to make sure to teach Timmy how to put on a bra and whatever other basic girl knowledge he ought to know. Harriet sent the browser back to the screen listing bras, panties and socks and clicked on panties this time. Several different styles appeared. Each of these came as packages of 5 panties and without asking Timmy clicked on the one that said it was bikini style. A picture of 5 gaily colored panties appeared. "These seem nice, don't they?" Harriet asked. "They're very pretty," Timmy said, "and isn't it so cool that they come in so many colors." "I guess that's true. Your boy underwear has been white, but girls often like to have lots of different colored panties. Anyway, the bikini cut is probably the nicest for you and we'll stick to that." Timmy looked at the other pictures and said, "what about hipsters?" "I find them to be cut too low and kind of uncomfortable. I don't know, maybe later on we'll branch out." "OK mom," Timmy said. "Now we journey over to the socks department." They proceeded to weave a path through the web site buying socks, some skirts and tops and sandals. There were some nice dresses but Harriet didn't sense they were exactly what Timmy had in mind so she suggested they try a different website for them. They went to the J.C. Penny checkout and ordered the clothing. Everything was in stock and in a week they could expect it to show up at the door. "Had enough for today?" Harriet asked. "No!" Timmy exclaimed, "I'm happy to look at more dresses." "OK, we might as well spend a bit more time, then you had better start your homework." They cruised around on the internet searching under the key words "girls dresses" and came up with a nice website where they decided on buying a pretty light pink organza over tulle, tea length dress with a full skirt and cap sleeves. In the back there was a satin bow, streamers and appliqu?d trim. Half the fun for Harriet was watching Timmy's eyes, the size of saucers as he carefully examined each dress that they saw. She was sure that she heard him gulp with excitement when he first saw the one that they finally picked. The last thing they searched for and ordered was some tights that he could wear with his dress and skirts. Harriet had to admit to herself that she had thoroughly enjoyed the experience. She truly was gaining the daughter she had never had. How many moms out there had the fun of shopping with their daughters - discussing which bra or skirt to buy - an experience she had never had, and so completely unlike buying clothes for a son. Of course, facing the reality of seeing her son dressed as a girl was another huge hurdle that she would have to leap over in a matter of a week or two. For the moment, however, she treasured the memory of sitting side by side with Timmy peering at the girl's clothes and she would get to relive it in detail when she told Ruth about it the next day. *** The day the packages of clothes arrived, Harriet was at home and Timmy was at school. She had been unsure of how she would feel when she first looked upon the girls clothes she had bought for Timmy, but she found herself pleasantly surprised, even happy that she had managed to get him such a pretty collection of things. Some lingering doubts about the wisdom of what she had done began creeping into her mind the closer it got to the time when Timmy would be coming home from school. The reality of having her son wearing girl's clothes and behaving like she had seen from her spy camera was sinking in and she began worrying herself sick. She would have to take the blame for having allowed him to pursue his obsession and she could imagine John yelling at her: "How could you not have known better? Turning our son into a girl? What terrible judgment you have. I'll never forgive you for that!" Suddenly nervous, Harriet thought that she should hide the clothes from Timmy. In fact, it was not too late to call the whole thing off. She had merely to tell John about Timmy's confession and then all would be over for better or worse. She called Ruth at work and told her that the clothes had arrived. The pretty dress with the organza and tulle was just totally precious. There was a cute built in starched crinoline that puffed out the skirt. It would be incredibly darling. "But every time I think of Timmy wearing that, I get cold feet. Do you think I'm doing the right thing Ruth?" "Just keep focusing on the alternative," Ruth said. "Sometimes a person has to pick between two tough choices and I think we've made the right one. You know, in time, I hope that that becomes clearer and clearer, even if now the reality of what you're doing seems scary." "I hope you're right. I guess I'll give him the clothes and we'll hope for the best." "Call me tonight if you can and let me know how it went." "I'll try." *** As he had done every day since he and his mom had ordered the clothes, Timmy ran home from school to see if they had arrived. Harriet greeted him at the door and by the smile on her face he knew that they were there. "Oh mom, I'm so happy" he exclaimed panting for breath. Harriet had spread the clothes out on his bed and when he came up to his room he looked at each and every package one by one. He held up the organza dress and said, "it's so much prettier than I imagined! Can I try it on?" "Well you know the rules. You've got a couple of hours now until your dad comes home, so go ahead and wear the clothes. That's why we bought them." "Thanks mom." "If you have any questions I'll be in the living room. You can also come down and give me a fashion show if you want." Timmy laughed and then said, "there is just one thing I don't understand too well." "What's that?" "I'm not so sure I know about how to put on an um..." He pointed to the package of bras. "Bras? Yes, I suppose you wouldn't know how to do it. Shall I help you?" "Would you mommy?" "Sure, take off your top," Harriet said and waited while Timmy took it off. She opened the package of beginner bras and took one out and handed it to Timmy. "It's best if I just tell you how to do it while you put it on yourself," and Harriet proceeded to lead him through the technique she used herself. "Look for the little ribbon on the front of the bra and then hold up the bra in your right hand by its left end." Timmy was so confused as to which was the left and right ends that Harriet finally had to stand behind him and guide his hands. "If all mothers have to go through such an effort with their daughters it's a miracle any girls wear bras at all!" she laughed. Timmy smiled seeing that she was just playing with him. Harriet continued, "now reach behind your back with your left hand and catch the right end of the bra." Timmy twirled around three times until he finally caught the end and Harriet roared with laughter. She could barely control herself enough to say, "bring your two hands together in front of your belly and clip them together. Very good. Now you can swivel the cups around to the front and lift up the bra putting your hands inside the straps on the left and right sides. Excellent." Timmy now seemed to be getting the idea of what he was doing. "The last thing is to make sure that your breasts are caught comfortably in the cups." She was tempted to show Timmy what that looked like in her own case, since his cups lay flat on his small chest. However, on second thought she wasn't sure it was such a good idea to undress in front of her son and discuss with him how she filled out her bra. She remembered that Ruth had told her how Timmy had said that his original inspiration for cross dressing came from seeing her in her underwear. The last thing she wanted to do was give him any more ideas. Despite the absence of breasts, Timmy made a serious attempt at capturing his own non-existent breasts. This time the effect was perhaps a bit more sad than comical and Harriet said, "very very good Timmy. I think you'll have no trouble putting on your bras from now on." With the pretty bra on correctly Timmy ran to a mirror to look at himself. "It's so pretty mommy, I love it." "It'll be easier to get on with practice," she said. A first big milestone in the life of her new daughter she thought: wearing her very first bra. She thought back to when she got her own first bra and tried to remember if her mother, Timmy's grandmother, had been excited about it. She couldn't remember one way or the other, she had been so focused on her own happiness of having passed through that transition into adolescence. "I'm going to first try on my dress," Timmy said. "First put on some panties," Harriet said. "I know mom," Timmy said blushing and indicating that she should leave the room so he could change. "OK dear, but I'm going to have to help you with the dress. It's got a back zip," Harriet said and she picked up the dress, unzipped the zipper and showed it to Timmy. "You'll have to put it on over your head and then I'll zip it up for you. Come to me when you're ready." Harriet left Timmy to himself and she went downstairs. So far so good, she thought. It seemed like such innocent play for Timmy and he was so happy. She smiled again at the remembrance of him struggling with the bra. She would make a point of describing that to Ruth. A few minutes later Timmy came down to the living room wearing his organza over tulle party dress. "I put on some panties and the tights," Timmy said. "I see," Harriet said trying to sound positive. The little stiff skirt stood out around him and Harriet saw that he had also put on his low heeled shoes. She got up and zipped him fully into the dress and said, "why just look at you Timmy, it fits like a charm. One would think it was just made for you." "I love it mom," Timmy said and he walked slowly about the living room with a dainty gentleness. Things inside him were opening up, some inner need that came out into the open once he looked the part of a young, pretty girl. Harriet felt a twinge of worry. Would it be hard for Timmy to transition back to his usual self when his dad came home? Or in school the next day? "I hope you'll be able to be yourself when your dad gets home," Harriet said and then realized that "yourself" could be interpreted either way. "I mean your boy self," she corrected herself. "Sure mommy, I promised you I would and I will. I don't want daddy to know about this." Harriet smiled. It was a relief: Timmy and she were on the same page. *** That night she called up Ruth. "You can't believe how precious our little princess of organza and tulle looks," Harriet gushed. "He's like a little doll. More delicate and girly than you or I ever were." Ruth laughed, "and everything fits?" "Yes pretty well really. It's remarkable. He showed me a few outfits, the shorts, skirts and tops all are lovely." "What about the bras?" "I was going to tell you. He asked me to help him on with it and I tried to teach him. It was so cute and funny. We both were laughing." "I can't wait to see him." "John will be travelling on business in three weeks. He'll be gone a week and you'll have to come over, that is, assuming that Timmy has no objection." *** The days went by one by one with Timmy spending a couple of hours each afternoon after school dressed in his pretty clothes. At first he favored the party dress but as time went on he branched out to experiment dressing in a skirt and matching top. He became an expert at putting on bras and stockings. A couple of times Harriet surprised him with little gifts. One time it was pantyhose and another it was a slip. One day she came home with a pink leotard, stockings, ballet slippers and a cute little tutu. "I saw it in the shop window, and I couldn't resist buying it for you, it's so darling," she told him. For the next few days Timmy flitted around the house as a little ballerina. After the excitement of the first week, Harriet noticed that Timmy would come home from school, choose an outfit and then get absorbed in his homework. It was as if he was defining normalcy in his life as being a girl. During the two hours that he was dressed up, if Harriet talked to him, Timmy seemed like a girl to her. It was a remarkable if subtle transformation and it was not what Harriet had expected. She thought she would always be looking at a boy play acting the part of a girl, but it did not seem that way at all. Harriet kept Ruth in the loop as much as possible about how Timmy was progressing in the role of her daughter. She purposefully didn't tell Timmy about his father's upcoming trip since she suspected that it would be hard for him to contain his excitement and he would act strange in front of his dad. A few days before the trip, however, John talked about it at dinner and Harriet could see Timmy's excitement and she signaled to him with her eyes that he had better be careful not to make his dad think that he was anxious for him to leave on his trip. Finally, on a Saturday morning, Harriet drove John to the airport with Timmy coming along for the ride. The moment his dad said his goodbyes and was gone, Timmy and his mom exchanged glances. They both understood that this presented new opportunities for Timmy. Harriet felt like she ought to try and rein him in somehow but she knew deep inside that it would be hopeless. The horse was out of the barn and not likely to willingly go back in again. "Your Aunt Ruth will be coming this afternoon for a visit," Harriet said. "Oh, does that mean I have to be a boy?" Timmy said sounding a bit deflated. "Actually, it's up to you. Your Aunt did see you wearing her underwear so I guess she wouldn't be too surprised if she saw you dressed as a girl today." "I won't mind," Timmy said and Harriet thought to herself "mark me surprised." "Can I mention it to her before she comes over so she won't be shocked?" "Sure," Timmy said, "but..." "But what?" "But I wanted to wear my pretty white and pink dress today. Maybe she won't like that." If only Timmy knew how much Ruth wanted to see him like that! "Don't worry. You look darling in that dress and I think Ruth will agree with me." Harriet glanced over at Timmy. He was smiling and happy. This was going to be an enchanted week. *** When they got back home from the airport Timmy made a beeline to his room and took out the clothes he had been planning to wear for this special day: his 30A cup bra, panties, pantyhose, his slip and his organza over tulle dress. Now that he knew that Aunt Ruth was coming he was more anxious than ever that he look his prettiest. It would be his way of trying to explain to her why his claim that he would never wear girl's clothes again had been wrong. He wanted to convince her that it didn't make sense for someone who felt as entirely feminine as he did should not dress as a girl. When he was fully dressed he stood looking at himself in the large mirror over his dresser. He still couldn't get over how much he loved the organza dress. He turned sideways and looked at his profile. Though it was nice to have a bra on that made a slight outward thrust over his chest, it would be a lot nicer to have a more definite figure. Also the time had come when he ought to wear some makeup. He went to his mom who was busy in the kitchen and said, "can I put some panties in my bra to fill out the cups?" His mother looked at him and stopped herself from saying any of the obvious objections: that it was silly and unnecessary. Clearly Timmy would want breasts like any young girl would. She hadn't thought about it before, but perhaps she would have to order him a couple of padded bras. "Sure, I guess it's OK!" "Thanks mom," Timmy said. Instead of rushing off he stood where he was and finally said, "since it's a special occasion

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Confession He looked over the pictures in the envelope one more time and smiled, that ulta conservative little girl was having sex with one of the nuns up the convent.? He knew what her father would do, he would disown her, throw her out on the street.? He has heard him rail enough times about homosexuals and how they are the vilest things that live on this earth.? He puts the photos back into the envelope and slipped them into his draw.? As he teacher, he felt, he should bring this to her...

2 years ago
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The Sex Rehab Diaries Staceys Confession

Author's Note: The Sex Rehab Diaries is an ongoing series, featuring the intimate confessions of the patients of Dr Clark's group therapy class for sexual addictions at The Belleview Retreat for Sexual Health "I'm Stacey, and I'm a sex addict." I knew I wasn't the only person in the room that was in denial over that statement even as it left my mouth. ‘Admit that you need help and recovery will come quicker and last longer'. I had to hold back my initial laughter as I'd read the...

4 years ago
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My Confession

Hi. My name is Erin. This story is excerpted from the June 19, 2011, entry in my blog about my round-trip road trip from Reno, Nevada, to Mount Rushmore, South Dakota. You can read the full blog here http://xhamster.com/user/teengirerin/posts/44615.html When the Priest calls me a "c***d", he means a "c***d of God". I am 18 years old, so this story is not about sex with an u******e c***d.*******I started my morning by going to a Catholic Mass in Douglas, Wyoming. I was raised Catholic. I used...

2 years ago
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The Unfaithful Wifes Confession

The Abbot Bendictus donned his long brown habit and tied the white cord around his waist.It was 6am and he was getting ready for the day. His day would be spent in quiet contemplation and hearing the confessions of those who came to the monastery chapel to repent their sins. It had been two days since the Abbot had used the cane on Dean and Lorraine and the memory of that day was still to the fore in his mind. He sat at his desk in his study and allowed the thoughts to waft through his mind...

4 years ago
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Letters to Abigail Janes Confession

Hello Abigail,Sorry for not writing sooner but things have been a bit hectic the last few weeks, what with Matty and Teresa's wedding. It was lovely to see you and the kids. Mom and dad were looking well, so moving out to the farm with you and Bob obviously agrees. Certainly better than an old folk's home.The house feels empty with Matty and Teresa on their honeymoon. Mind you; I don't think he or any of the other hotel’s guests will be getting much rest if what I saw at the bachelorette...

Cheating
3 years ago
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The Confession

Choking on my own tears, moaning through blood smeared panties, unable to swallow, both hands bound with rope far apart on the same brass bed where we conceived our first child, our only child—Milena, who is dead now—I am at last at peace. Karajan, my lover, finishes what is needed to my legs, binding them together like a mermaid’s fin. "Now you have some time to think," he...

2 years ago
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Hot Fuck After Confession

This story is just a fiction.I am May, 20 years old. I am horny and naughty especially for hot daddies. I do horny things everywhere, in the office, in a club, as in everywhere. I offer sex and blowjob for free and let daddies fuck the way they want. Im a dirty slut, really dirty.I wanna be fucked by daddies who can shoot a blast of hot, thick, milky cum. And the older the daddy is, the hornier I become.One day, I decided to go to a church to confess about my horny deeds. I approached the...

3 years ago
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Untrue confession

He had returned to his quarters and tried to dismiss his thoughts but they would not leave him and the harder he tried, the more they remained on his mind. Unable to gain relief from them he had masturbated for the first time in years and he was greatly distressed when he accepted that he had enjoyed it. He had still been unable to get the thoughts of Sister Beatrice from his head and she had now become something of an obsession with him so that finally he had given way and sent word for her...

2 years ago
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Her Confession

She walked into the confessional. Her raincoat and head scarf dripping wet. "Bless me Father for I have sinned." "How long has it been since your last confession my child?" asked the priest. "Oh my God, so many years father. "She answered. "Is there a reason for this? "He asked her. "I've just been lapsed for many years although I attend Mass occasionally." "Then proceed my child." "I'm very troubled tonight Father about something I've done." she replied...

3 years ago
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Confession

Miriam Hartley was a seventeen-year-old ugly duckling that only recently had begun to blossom. Her flat chest was only now having small but perceptible bumps with tiny yet very sensitive nipples.Miriam had discovered masturbation. She had also discovered porn on the internet and would masturbate incessantly while watching porn. While not having actually seen big cocks, the cocks she viewed while watching porn, simply mesmerized her.Having been raised Catholic, Miriam was conflicted with her...

Seduction
4 years ago
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The Confession

"Honey, I have a confession to make."I looked into Mat's eyes as he made this statement, and I could see he was quite serious. Needless to say, I was curious and quite intrigued. I looked back at him, my eyes indicating he should continue."We both know that I'm not able to meet your needs sexually," Mat began. "I wish I was more well-endowed, and I know you need more than I have to offer."I covered my mouth with my hand so that he wouldn't see me smiling. His four-inch cock has always been a...

Fetish
3 years ago
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A Confession

I'm sorry to my friends who've missed my diary. I'm really flattered that you seem to like reading about the rather ordinary events in my simple little life. I hope you'll understand that I've been trying to study for my final examinations, and simultaneously trying to stifle (usually unsuccessfully) these awful desires inside me. I guess I've missed writing the diary. You see, it acts as a kind of confessional for me. I don't go to confession any more, and writing my diary acts as a way of...

3 years ago
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Priestly PromiscuityChapter 3 Sister Susans Sapphic Confession

God had a purpose in mind. Father Murphy was sure of that. He was punishing him for his transgressions, his weakness, and his surrender to the sins of the flesh. The young priest sat at his desk in the dimly lighted room and reflected guiltily on the terrible things he had done since coming here to this school. He wanted to fall to his knees and pray for forgiveness. He hadn't even confessed his sins. He couldn't bring himself to admit them to another, not even the kindly Father...

3 years ago
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Helenas Confession

The priest sighed to himself and reluctantly got up from the chair. Time to hear confessions, he despondently thought to himself. His was no longer a religion of love and forgiveness - at least not from his point of view. Why should these disgusting sinners be forgiven and accepted into the Kingdom of God. Why should they ultimately be treated the same as he? Hadn't he always struggled to remain good and pure - while these sinners had let their lust have its way in disgusting, sinful...

4 years ago
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My Confession

On a cold February day, I went to visit a friend. I went with a letter in my hand, words I wanted her to read. What follows is that letter. The words in italics are the words I spoke to her as she read. I read my copy of the letter at the same time. I am a dreamer. And a writer. This combination can either work, or it can be incredibly volatile. Why am I telling you this? I need to clear my mind of thoughts, and I need to do this in order to move on. Again you are asking why I am writing to...

4 years ago
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My Confession

On a cold February day, I went to visit a friend. I went with a letter in my hand, words I wanted her to read. What follows is that letter. The words in italics are the words I spoke to her as she read. I read my copy of the letter at the same time. I am a dreamer. And a writer. This combination can either work, or it can be incredibly volatile. Why am I telling you this? I need to clear my mind of thoughts, and I need to do this in order to move on. Again you are asking why I am writing to...

Wife Lovers
4 years ago
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A widows erotic confession

As the springtime was turning into summer I’d just about completed the changes to my life that I felt were necessary at this juncture. I’d found a new home in a different location where nobody knows me, and I was now between jobs as I contemplated my future. As a confident and gregarious person I had no qualms about seeking fresh opportunities or making new friends, which as it turned out, happened much sooner than I expected.It was only a matter of days after I’d moved in to my cosy new...

Taboo
3 years ago
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Thanksgiving Confession

Now don’t get me wrong, I’m anything but innocent most of the time but this was not something I had planned. This happened without any planning or the knowledge of my husband at the time, thus me writing this so as my confession to him about what happened this fateful Thanksgiving.I enjoy cooking and having company so we hosted another Thanksgiving here at our home with lots of good friends, good food, and good booze.I am a happily married and very promiscuous 46 year old ginger. I take good...

2 years ago
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Mom After Mom 8211 Part 5 The Confession

Me – “What are you talking Di. Why would I act? And for what?” Di – “Why were you running away now?” Me – “Why would I run away? From whom?” Di – “I know you. Don’t try to fool me” Me – “I am not able to understand. What are you talking about?” Di – “Why were you hiding away from me now?” Me – “No Di. I didn’t notice you. I just got a big project. So I was checking the details of it” Di – “I saw you walking in sometime back, checking me at times. But you were occupied with your clients. So I...

Incest
3 years ago
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Confession

(C) 2005 Rachel Gumm. I glanced up at Mark as he finished wiring two leads to a small box of electronics. The other ends of the leads were connected to a cold, metal dildo, which was strapped firmly inside me. This was my punishment for last night.I shuffled slightly on the bed, the bonds allowing me very little movement, but the device stayed firmly inside me. My ankles were tied to the front corners of the bed, and my wrists were tied to a table that was fixed in place over the top of the...

BDSM
3 years ago
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Confession

CONFESSION CONFESSION Sept 4th 2003, Received a call from an old school girlfriend,she had split from an unfaithful partner & was looking for a stop overto sort her life out. She had not called me for around 3 years, but we were very close as schoolfriends, and had some mutual friends in adult life. Feeling apprehensive ofher staying with me, I still agreed she could come. But how would I hide thelife I lead. The dungeon below my home & the frequent phone calls I received & thelavish style I...

4 years ago
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The Confession

THE CONFESSION "Shit," I said as I almost tripped. It was morning when I got out of bed to go to the loo and almost tripped up over the panties that were lying on the floor. I bent down and picked them up and looked at them and thought when do panties stop being panties and become big knickers. I continued out to the toilet still holding the panties and sat down to pee. I held them up and thought, wow, these are big. They were black with a decorative panel in the front with a...

3 years ago
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TNWS01 The Girl With The Voice of an AngelChapter 39 Bjorns Confession

Bjorn Erikson looked at Jessie Harper just as he was about to strip himself naked in front of the other six people in the Communal Dormitory of Camp Starkers. He started pulling at the bottom hem of his t-shirt then said to Jessie, “Well, I guess I was wrong about nobody wanting to get naked in the six days we were here at Camp Starkers. But don’t get me wrong, because I am kind of glad that this is happening ... and I do have a little bit of a confession to make before I take my clothes off...

1 year ago
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Raw Confessions

RawConfessions! If you think I only ever review websites that have smut on them, you’re dead wrong. You might be disappointed to see me reviewing Raw Confessions, but I’m playing the long game here. I’ve already covered thousands of high-quality porn sites and branched out into gaming and VR shit, so I figured I should cast a wide net across forums as well, especially if there’s potential for smut down the line. Currently, Raw Confessions is an adult confessions forum. That much should be clear...

Sex Stories Sites
4 years ago
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A Sissies Humiliating Confession

This is a real life situation that happened this past weekend. I am sissy slave jennifer and i am owned by my beautiful Mistress Rita. Mistress Rita loves nothing more than putting this pathetic lil sissy through the most humiliating situations She can get away with. I once confessed to Mistress that when i was 16 i wore my very 1st pair of panties. Mistress insisted that i tell her who's they were, where i got them, and how i got them. i was embarassed to confess that i actually stole them...

2 years ago
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Father Leary Hears More Private Confessions

Father Lester finished his last confession early. There were no more high school kids waiting except for two who always waited for Father Leary. Lester went to the rectory meaning to stop by Father Leary's office to pick up some papers that Leary had asked him to look at for him. When the thirty year old priest entered the outer office he noticed a pretty young girl sitting patiently on a bench. "Good afternoon Father Lester." Young Jill Ebber said with a sweet smile on her face. "Good...

2 years ago
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E088 Emmas confession

After a glass of wine together and some cheese and crackers, Emma and Donald go back into the water one more time.  They swim and play together, but Donald can tell Emma is distracted. When they get back on the shore, he has her lay on her stomach as he rubs the aloe vera over her shoulders, back, and thighs where she is the reddest. Emma sighs with contentment as he does.But then she rolls over and looks him in the eyes and tells him, “Donald, I did something horrible.  I feel so bad.  When I...

Love Stories
4 years ago
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Friends Mom True Confession

When I was younger I was always really into my friends mom; she was your perfect milf, she was probably in her mid 40s, very short petite woman with C sized breast with a slight sag. One night when I was sleeping over we started going through a bunch of old photos at there house. After about three quarters through my pile of photos I was looking through I came across a exciting surprise. It was a photo of my friends mom on top of a ski mountain topless with her small dark nipples visible...

4 years ago
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fantasy sex confession

For those that are used to my usual style and have offered such lovely words in their feedback, you may not like what follows. It is somewhat different in style and a departure from what I usually do. But hey, I personally need to write this, I just have to get it off my chest, it is a sort of confession if you will. If you really don’t like it, just stop reading, click away and I will return to my normal style soon enough.I have been asked what made me start writing what are essentially short...

3 years ago
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I Have a Small Confession

I have a small confession. Well, not really a small one, a fairly large one, and I'm not so much worried about confessing as I am professing. I want to shout this out to the world for some reason, for all that's wrong with it, and how much I've relished in the thought of it since the act has occurred. Let me start the night before, and lead up to now. My sister Michelle has three wonderful kids. Lee, who is a stunning eighteen year old, Kay, who is a cute five year old, and Michael, a boy...

2 years ago
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HannahChapter 3 Confession

I woke up the next morning cuddled in the arms of my very first lover, an exchange student from Armenia. There was no love as love is usually defined, but there had been a need fulfilled by each of us, a kind of mutual affection. I didn't feel bad at all. I slipped out of the bag and found my pajamas, put them on and walked to the bathroom. It was cool but not cold, and when I returned to the large room I found everyone still sleeping. There was some daylight coming in through the windows,...

1 year ago
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Crack Whore Confessions

Heard any good Crack Whore Confessions lately? I guess that might depend on if you’re the kind of guy who gets his rocks off safely to the sexy girls of the Internet or if you’re the kind of guy who risks infections and robberies getting a piece over on the sketchy part of town. Hey, I’ve been there before. Sometimes when you’re hard up, the girls who hang out around the hourly motels start looking a hell of a lot more attractive. I’ll tell you this much: they’re even sexier when it’s your...

Premium Extreme Porn Sites
4 years ago
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Father Learys Private Confessions

Normally Thursday afternoon confessions were something Father Leary disliked. All those high school teenagers confessing the same sins every week, but this Thursday the priest was in a splendid mood and was more lenient than usual when doling out penance. He was in a good mood because he expected young Jill Ebber this Thursday to give penance in the good Father's private office as she had done last week. The fifteen year old had allowed the priest to spank her on her cute rounded bare bottom...

4 years ago
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Hypnotized Confession

Patty opened her eyes, they were slightly glazed and unfocused as she looked at Doctor Marks, the drug had taken effect. ‘How do you feel, Patty?’ he asked the pretty twenty-six year old, and she blinked long lashes at him. ‘Ok…’ she said, her tone was rather vague and her eyes seemed to have trouble focusing on him. Smiling he sat back, she’d asked him to hypnotize her for this particular counseling session… they were going to explore some of her basest instincts and she felt rather...

3 years ago
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Best friend has a deep secret fantasy Chapter 2 The Reluctant Confession

and kissed her. Our tongues working together like they were meant too. She was an unbelievable kisser and my cock started to harden as a result. As we kissed I opened the door. We broke the kiss, "God you're an amazing kisser." She said as she walked out the door. I then got dressed in clean cloths as I thought of what had just happened. My cock grew so hard that it was difficult to get my boxer briefs on. Once we dressed we went to the living room. "Sorry, we ran to the store earlier,...

4 years ago
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A Pregnant Bride8217s Confession

Can you imagine how it feels 2 months after your wedding to discover that you’ve married one of the big- gest sluts in town? I didn’t find out until she let me know that we were expecting our first child. “Darling, I have a confession to make and it’s going to test if you really love me as much as you say you do.” My wife said to me after dinner one night. “Cindy dear, you know I do love you very much. What do you have to tell me?” I asked...

2 years ago
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The Confession

‘Honey, I have a confession to make.’ I looked into Mat’s eyes as he made this statement, and I could see he was quite serious. Needless to say, I was curious and quite intrigued. I looked back at him, my eyes indicating he should continue. ‘We both know that I’m not able to meet your needs sexually,’ Mat began. ‘I wish I was more well-endowed, and I know you need more than I have to offer.’ I covered my mouth with my hand so that he wouldn’t see me smiling. His four-inch cock has always been a...

3 years ago
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CONFESSION

Confession By Blueheatt __I hooked up with new girlfriend Ava. She was a professional licensed sex therapist. As time went by she told me how these women just need to get things off their mind and then she can get to any problems after that. I said: I bet you have a lot of stories you could tell. She said she couldnt tell any of them because of legal confidentiality rules, like a priest will never reveal anything said in a confessional. No law can force him to. I like to write porn stories,...

4 years ago
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My cheating wifes confession

I had just spent a night with Marg and had concocted a story to stop my wife Sue from being suspicious.After Marg returned home a couple of days later I had a lot on my mind. Sue had accepted my explanation for not coming home although Mike told me later that she had checked my story with him the next day. Sex with Sue was becoming routine like washing the dishes or mowing the lawn. I’m not saying it was not enjoyable, much better than wanking off in the shower but it in no way compared with...

Cheating
3 years ago
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Naked Confession

I like to get naked.I especially like to get naked outdoors.Just typing these words gives me a warm, wet, tingly feelingI have had this naked outdoor addiction since I was very young girl. Our family lived at the base of a small mountain. My brother and I and the neighborhood k**s loved to play in the woods above our house. We devised all sorts of imaginary games, although none involved taking our clothes off.I was ten the first time I climbed the hill by myself. My favorite spot was a little...

3 years ago
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Gloryhole confession

Glory Hole ConfessionIt all started about three years ago. I have a good marriage, and my wife is a sweet woman but is a little selfish in the sex department. When we would have sex I would start by kissing and licking her up and down then give her multiple orgasms where by she would usually squirt. I would use my mouth and hands as well as toys. She would be so hot all she wanted was to get fucked. Well, in the 45 min to 90 minutes I spent on foreplay for her I had usually gone soft and needed...

1 year ago
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Leannersquos Confession

I’m writing this, less as a confession, but more so you know what happened. I know that I stood you up the day of our wedding, ran away from everything we had, and you haven’t heard from me since then, but I still care for you enough that I want you to know the truth. First I need to tell you that I really was a virgin, I know that was important to you, I had been saving myself for marriage. Things changed though on the night before our wedding, the night of my bachelorette party. As...

4 years ago
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My First Confession

You asked for it so here it is:This is my first confession of many more to comeFrom finishing school I’ve always liked being bough expensive items bags, shoes and jewellery. So when I did my work experience in a charity shop and I had many old charming men come in and try chatting me up! Now I like older men (not that old but older than myself) so I enjoyed it I never acted on it but it opened my eyes to the more vintage experienced richer men! When I turned 16 I went through a few...

3 years ago
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A Brides Confession

Can you imagine how it feels 2 months after your wedding to discover that you've married one of the biggest sluts in town?I didn't find out until she let me know that we were expecting our first c***d."Darling, I have a confession to make and it's going to test if you really love me as much as you say you do." My wife said to me after dinner one night."Cindy dear, you know I do love you very much. What do you have to tell me?" I asked inquisitively as I held her hand."Honey. I do love you very...

1 year ago
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A Wickedly True Confession

I will never forget that dreadful day, when Charlie, Bruce and Daniel, lured me to that basement. The three of them attacked me and viciously took my anal virginity. Until that day I had no thought of two males having sex, or that more than one male could sexual attack another. On that day all my innocence was stolen from me. When Charlie slammed his fist into my unprotected stomach and Bruce held my ankles, Daniel removing my pants and underwear, my life changed for ever. The three of them...

2 years ago
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A Brides Confession

Can you imagine how it feels 2 months after your wedding to discover that you've married one of the biggest sluts in town?I didn't find out until she let me know that we were expecting our first c***d."Darling, I have a confession to make and it's going to test if you really love me as much as you say you do." My wife said to me after dinner one night."Cindy dear, you know I do love you very much. What do you have to tell me?" I asked inquisitively as I held her hand."Honey. I do love you...

3 years ago
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B5 Chapter 22 Dee Dees Confession

Chapter 22: Dee Dee's Confession The incredible sexual encounters continued for both Jeanne and Jordan. Each girl was pushed to her limits on a daily basis, with a variety of partners, and constantly varying sexual acts. By the time the contest was near, each girl felt as though she could fuck the living daylights out of anything that lived. When she wasn't helping the other girls putting Jordan through the sexual wringer, Dee Dee continued to go through all the files and programs on...

2 years ago
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The Unfaithful Wife My Confession

This is Nikita, a 26-year-old married pretty woman. I got married last year just 5 days before I turned 26. Mine was an arranged marriage. We met, chatted, spoke and liked. The initial 6 months flew by like a honeymoon period with lots of love and yes lots of sex. But then got the monotony and work. My husband loves me a lot and is superb in bed but I was always lot kinky and needed attention from my college days. (6 months back) This was when my best friend from college, Akriti who had now...

2 years ago
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CONFESSION

THE CONFESSION If I had to describe myself or the life that I have lived up until this point I would say that I have known the pleasure of the flesh to be the greatest part of my life. Some might say that I have been damaged by my up bring, but how can having the complete love and devotion of two loving parents be wrong? Yes the title of my story is correct, I am an i****t whore; having fucked nearly forty members of my family, watch includes my mother and father, my two brothers and four...

3 years ago
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Alexa Chapter 5 The Saturday Night Confession

Alexa Chapter 5: The Saturday Night Confession I don't know what was worse, the sudden blast of sunlight that seemed to hit me or Katie's saccharine voice telling me to get up. "Leave me alone Katie." I can't believe how bad I feel. My head is pounding from the worst hangover I have ever had in my entire life. I'm blaming Jenny for the condition I find myself in. I'm sure I had no hand in how bad I feel. "Get up Alexa," Katie says to me. "You are the one who thought...

2 years ago
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Portias Confession

Portia's Confession I have for years struggled to repress the desire in me to put on women's clothes. It's always been part of me, this desire, a part of me and of even my earliest memories. Ever since I swapped clothes with my girlfriend and best friend at around the age of three. Why has this desire been a struggle? Why don't I just put on the clothes and have done with it? Part of me asks these questions. Why can't I? Am I afraid of society's disapproval? No, I have...

3 years ago
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Savita Bhabhi 8211 Episode 21 A Wife8217s Confession

Our sexy bhabhi Savita and her new friend Shobha were shopping for clothes in the mall. “Doesn’t this dress look adorable, Shobha?” Savita had found a particularly sexy dress and asked Shobha for her opinion while trying on a pink salwar. “It’s good bhabhi, but why don’t you try this one instead?” Shobha handed Savita another dress. “How does this one look?” asked Savita after considering it. “It looks great, much better than the last one!” Meanwhile the salesman at the shop was looking at...

4 years ago
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Bell Whistles SecretsChapter 2 Irmas Confession

Audra had decided to make Irma and I breakfast and had let both of us know quite clearly that our help was not needed. As I sat down across from Irma shaking my head, Irma asked, "What are we going to do with her?" The question surprised me. Irma looked over at me and said, "I suppose you think I like being waited on." I shrugged, not knowing what to say. Irma responded, "I love Audra. I suppose I was much closer to her than her parents but I cared for them as well. I never wanted to...

1 year ago
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Dirty Confession

What can you expect from dirty little sluts other than dirty little confessions? I feel like checking out the hot babes on Reddit is one of the best ways to experience some of the hottest confessions ever, but you just need to know where to look. If you want to look in the right place for confessions of sexual nature on the Reddit.com platform, then there’s only one sub that you should check out and it goes by the name of /r/DirtyConfession. Now, as The Porn Dude, I went ahead and tried the...

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