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Sound Sissy By Karen Singer Written in 2003, this is the first story I ever wrote. In fact, I thought I hated writing until I decided to write this. Now I can't stop writing. I am submitting it here to serve as a marker to show how far I've come as a writer since then - now that I am actively trying to find an agent for my "legitimate" books. As such, I've done almost no editing so it is pretty much in its original state. I know I went horribly wrong with this story near the end, but that too remains for the same reason. And despite that, I think many of you may very well enjoy it. Part 1: And In Walked Chaos Hi, my name is Don. Well, most of the time my name is Don... Well, that's not quite right anymore, "most" of the time my name used to be Don... What I mean is, my name "used" to be Don "most" of the time... I mean "most" of the time now my name is Karen... Why don't I just start over. Hi, my name is Karen... well, "most" of the time my name is Karen... Let's not go there again! If you think that was confusing, you can imagine how I must feel. This is not the story of the beginning, nor is it really about where things stand now, it's simply about some things that happened over the last several months. Now that I think about it though, I guess I have to tell you at least a little bit about the beginning, so you can understand what I'm talking about. I should start by telling you that I am a transvestite "sissy." I'm a student at the University here and am now nearing the end of my Junior year. I'm majoring in Electronics Engineering and I actually credit my good grades to the fact that I'm a transvestite. I shared an apartment off-campus since my freshman year with a friend because the school here just didn't have enough dorm space. That's ok, my friend Tom actually got me started on this transvestite kick. He's not one himself, but one night when we got really drunk together, I told him about my lifelong desire to wear girl's clothes and he rather bluntly told me that if that's what I really wanted to do, then I should just do it! He wouldn't mind - just as long as I kept it quiet and didn't try to do anything "queer" with him. That conversation hit the target for me, and it wasn't too long before I was collecting a small wardrobe of "girly" things. My grades certainly improved, because I would come home from class everyday, change into something more feminine, and then stay hidden in my room with nothing to do but study. Tom didn't seem to mind too much the few times he saw me dressed, and he minded even less when I started to clean the place up while he was out somewhere. I guess I was starting to feel domestic. Besides, I really enjoyed any excuse to get out of my room and do something while dressed. I've had a career goal for many years to one day be a "sound man" for big time concert performances. In my freshman year, I met some friends who had started a band and it wasn't long before I had volunteered to run the audio for them. For the first couple of gigs, I rented a small sound system with the rental fees being provided on top of my pay cut. After that, I started buying some used stuff and over time have slowly built up a really nice little system that I'm pretty proud of. The fact that the band has become really popular at the local clubs hasn't hurt things a bit. We seem to work two or three weekends out of every month and sometimes we even take a gig during the week as well. The most significant person in my life right now is Cindy. Cindy is one of the vocalists in the band and is also the band's manager. She's a good choice for manager because she's naturally "bossy," always seems to cover all the details, and just plain likes making arrangements for everything. She's also a business major, which doesn't hurt either. Cindy is drop-dead gorgeous! Since I met her, I've always wanted to be with her. I've also wanted to be able to dress like her and have spent many hours wondering what it would be like wearing some of her clothes. I guess I've always been jealous that she can dress and look like that but I can't. When I met her though, I figured I could never interest someone like her. After all, she's "fantastic," and I'm pretty much a skinny little runt (only 5 feet 6 inches tall on a good day). Cindy is also the reason I can't hide in my room anymore. Back near the end of September last year, I was in my room studying after class as usual. I was also wearing a nice little short blue dress that I had along with panties, pantyhose, a bra (stuffed with some of my socks), a pair of mid-heel black pumps, and a little bit of makeup. I didn't own a wig yet. I didn't hear the knock at the front door, but I guess Tom was out there and answered it as he was leaving. Cindy had stopped by to tell me about another gig she had booked for us. Tom really wasn't thinking I guess, because he just told her I was back in my room studying. I didn't know she was there until she just opened my door and came in calling my name. What a shock! For both of us! I was so scared and panicked that I couldn't move or say anything. It felt like I just sat there with my mouth and eyes wide open for and eternity, not knowing what to say or do. It was several moments before either of us recovered and it was Cindy, naturally, who was able to speak first. "My God! What are you wearing?" she said. I couldn't find the words to answer her, but it really wasn't necessary, and I don't think she was ready to hear me say anything yet either. She just came all the way into the room and kept talking. "Look at you! You're wearing a dress, and heels, ... and a bra!... and makeup!" Trust a girl to notice the details. "Geeez!" she said. "What are you?" "Cindy," I started. But that's all I got out as she continued to carry on. "I never imagined you were a queer." "I'm not a queer!" I finally managed to say. "Well look at you!" she shot back. "What else am I supposed to think?" "If you're not a queer, then what are you?" At that point all I really wanted to do was to run away somewhere and hope the earth would swallow me up. But there was nowhere to go. I was stuck there, and Cindy was right there with me. It was a moment before I was finally able to answer. The panic of the moment was still on me, but that little bit of hopelessness was starting to sink in. My voice came out quiet and reserved. "I'm not a queer" was all I said as I hung my head. "Well then, what are you?" she asked a little more calmly than before. "I don't know," I said, "I'm just not a queer." She looked at me for a moment, then sat on my bed. "Maybe we better talk about this," she said. I must say, she recovered a lot faster than I did, but then it wasn't her life that was ending. Cindy has always been good at talking to people and getting the information she wants. I remember that she did her best to put me at ease even though all I really wanted to be was anywhere but where I was. I had some thoughts going through my head about being angry with her, and angry at Tom for putting me in this position, but what could I say? Besides, it was really me that was the problem, not her. I was a guy, sitting in front of her, wearing a dress. I was stuck, I was trapped, and there was no way out of it. I remember I was actually honest with her about what I did. Besides, I'm not a good liar, and knowing her, she would have gotten to the truth anyway. I also remember two other things about that conversation. The first is that I vowed to myself that I would never dress up again and that I was going to throw all my "girls" clothes away immediately. But as soon as I mentioned it, Cindy squashed that thought quickly. She told me that since I really liked doing it that much, then I would eventually just start doing it again anyway, so why throw away all my things. She also wouldn't let me take off anything that I was wearing while we were talking; I know because I tried... her voice can be rather forceful when she wants, and can carry a lot of authority! The other thing I remember about that conversation was that at some point, near the end, I pleaded with her, very politely, to please not tell anyone. I remember very plainly her just looking straight at me, and saying, "You must be kidding! I couldn't keep quiet about this if I tried... or if I wanted to for that matter!" My feeling of helplessness increased a thousand fold, and another bout of absolute panic set in. "But Cindy," I said, "What am I going to do? Everyone will know!" She looked at me with a slightly surprised look on her face and said, "That's right Don, everyone will know. But you're going to have to face them and just keep living as you have been. You have your schoolwork to do and you have your job with our band to take care of. The only difference now is that everyone will know about you. You like to wear dresses and I'm not going to let you hide it, and you're just going to have to learn to live with that!" And with that, she walked out and left me to my own thoughts. It's a good thing I didn't have any major tests that week, schoolwork was the last thing on my mind for quite some time. All I wondered about was who knew, what would they say, and what would happen. Over time though, the only real difference in anything that I saw was that a few people, mostly the members of the band, looked at me a little strangely for a while, but in the end I guess, they just got over it and accepted me for what I was - for the most part. I did get a few teasing comments from some girls once in a while, such as asking why I wasn't wearing a dress that day. All I could do in those cases was to smile and keep walking. The funny thing was though, that Cindy became more and more interested in me. My cross dressing seemed to fascinate her and she started spending more and more time at my apartment getting me to dress up for her. She didn't let me stay just in my room though. She insisted that I at least move freely about the entire apartment, day or night, no hiding. During the day, I wasn't allowed to lower the shades on the windows and if someone came to the door, I was supposed to answer it dressed just as I was. "After all," as she told me, "everyone knows anyway." She also often invited other friends over without my having any say in the matter. Let me tell you, it's an interesting situation to try to have a group study session with several friends while you're dressed completely as a girl. There's no way you can concentrate on what you're trying to learn. At least she respected my wishes and never forced me to leave the apartment while dressed - even though she did keep trying. I loved it. I hated it (sort of). I spent a lot of time with major butterflies in my stomach. And that's pretty much how things went for the rest of the year. Cindy was always trying to get me to do more and more and I kept dragging my heels (so to speak). There were a few areas that I guess she did make some progress in. Early on she insisted that I start removing all the hair on my body, regularly. She even got me some of that stuff you've seen on TV that you spread over the hair, apply the cloth strip and then "rip" the strip off again along with the hair. I must say, it does work and it keeps the hair away for weeks. In fact, I find myself having to do it less and less as time goes on. Another area that had improved, or worsened, depending on your point of view, was that I agreed to not wear men's underwear anymore. After all, no one can see your underwear anyway. So with her watching, I threw out every pair of masculine underpants that I owned. She kept trying to get me to wear more and more feminine stuff outside the apartment, but for the most part, I refused. I did spend a few days at the mall wearing dark colored pantyhose instead of socks, but that's about it. My wardrobe certainly grew, and gradually included a wig, weighted breast forms, and lots of other pretty things. Cindy never seemed to tire of taking me shopping. Unfortunately, she also loved to look for ways to make it as embarrassing for me as possible. I'm not sure if I just got more used to her little humiliating comments, or if I just really started to love them. True to her word, she had no problem with letting it be known that I liked to wear women's clothing and I usually had no choice but to stand there and admit it. But that's just all the ancient history. Let's finally move on to the real reason I'm telling you this story. Part 2: Gullible's Travels It happened back near the end of this past September. Cindy had booked the band into a new club that was about three hours away from here for Friday and Saturday nights. The pay for this one was going to be really good, and the club's manager was going to spring for 2 nights at a local hotel for us. The plan was to leave here on Friday afternoon about 1 o'clock and come back on Sunday. Our drummer, Tim, owned a small trailer that we used to carry most of our gear in, and we packed that on Thursday evening. I did one other thing on Thursday evening too, I purchased a package of men's underwear. I figured that since I would be rooming for two nights with one of the guys, that they really wouldn't want to see me in panties. Big mistake! All of us tried every semester to arrange our class schedule so that we had Friday afternoons off in case we needed to set up for a job somewhere. This semester was no exception for me and the only class I had was a two hour Literature class that ended by 10:00 a.m. Both Cindy, and Elaine, were in the same class with me, and neither of them had anything after that either. Elaine is the other female vocalist in the band and she also plays guitar. Cindy and Elaine both have great voices, but when they sing together, there's a kind of magic that happens. It's really great! Elaine was also Cindy's roommate and, of course, also knew about my cross-dressing. In fact, she often came over with Cindy - I think just to tease me. After class on Friday, Cindy asked me if I was packed and ready to go yet. I told her that I was definitely packed and couldn't wait to get under way. I think it was Elaine who said they were also ready to go and suggested that they should get their things and come over to my apartment to wait. "We can have lunch together" she said, "and since we're all riding in Tim's van, he won't have to go out of his way to pick us up." I told them that it sounded like a good idea to me - or so I thought! Cindy and Elaine got to my apartment surprisingly fast. They were there by 10:30 and Cindy came in carrying a small backpack that she used to carry her books in. "Hey Don," Elaine said as soon as they were there. "Why don't you show me the new outfit you got this week?" Cindy and I had been shopping earlier this week and I had purchased (at Cindy's insistence) a skirt and blouse along with a new pair of shoes. "Ok, I guess so," I said as we walked back toward my room. I pulled the skirt and blouse out of the closet to show her but she said, "Put them on. I want to see what they look like on you!" Now Elaine and Cindy had both been partner to seeing me get dressed many times so while I was embarrassed about changing in front of them, I just shrugged my shoulders and said, "Sure, we've got lots of time," and I started to get undressed. As soon as I got my pants off and Cindy saw the underwear I was wearing, she cried out, "What have you got on? You agreed that you weren't going to wear men's underwear any more!" "I bought them last night," I said. "I figured that whoever I roomed with wouldn't want to see me in panties all weekend." "Well you figured wrong Buster! We'll discuss this later! Besides, Elaine is going to room with Stan on this trip so you and I will be sharing a room. Now get those things off!" Stan is the bass player in the band and he and Elaine had been going together for quite some time. It was only a matter of time, I new, before they would be moving in together. I stripped down to nothing and got a pair of panties out of my dresser. Having both girls watching me, along with just dressing up in something feminine, had its usual affect on me and as I pulled up my panties I noticed the first familiar stirrings of arousal. It may be a long trip I thought to myself. How little did I know! Elaine insisted that I get dressed up completely, "So I can see the whole effect," as she put it. So I went the whole nine yards and got out a bra and the falsies, put some pantyhose on, and finally put on the blouse and skirt. The blouse was a very feminine white blouse with lace at the collar, the cuffs, and down the front button line. The skirt was a simple, tight black skirt that came down to about 2 inches from the top of my knees. The shoes I had bought were sort of like black loafers with squared off toes, a silver decoration across the top, and had wide heels about 2 inches high. The whole look was very conservative, very feminine. As I modeled it for them, Elaine finally said, "Oh, you were right Cindy, it looks very good on him. The only problem I can see, is that ugly looking bulge in the front of his skirt. Not very feminine looking is it!" "No it's not," answered Cindy. "It looks downright awful." She paused for just a second, looking at me, then turned to Elaine, "What do you think Elaine, just this once, maybe we could 'take care of it' for him. I'm sure he would probably like that, don't you think?" "I'll just bet he would!" Elaine answered sarcastically. "Well Don," Cindy asked, "since we have some extra time here, would you like us to take care of that nasty bulge for you?" I just looked at them in amazement. Cindy and I had done some heavy petting on occasion, but she never had allowed me to have any kind of actual sex with her. She had this unmovable rule that she was "saving herself" for her wedding night. "Absolutely!" I said. "Now I'm not talking about having intercourse with you," she said, "we're just offering to get rid of that bulge for you, that's all." "Fine with me!" I said only slightly disappointed. This was still something new in our relationship. Before, I had always masturbated by myself when no one was around. Now here was not only Cindy, but Elaine as well, offering to do it for me. An absolute dream come true and a major step in the right direction, or so I thought. "Just take off your skirt, pantyhose, and panties," she told me. When I was naked from the waist down, she told me to sit on the foot of my bed. "Wait a minute," Elaine said. "Let me get a towel to put down under you, we don't want to make a mess now, do we." She went to the bathroom and got one of my towels and laid it out on the end of the bed. "Now just lay back here," Cindy said. "You know," said Elaine, "I've really got to be careful with how we go about this. I'm willing to help you out with this, but I don't want there to be any chance that he'll get over excited and try to touch me in any way that he shouldn't. I'm Stan's girlfriend, not his. I know it's an inconvenience, but is there any way we can tie his hands to the bed so they'll out of the way?" "Fine with me," said Cindy. "Do you mind, Don?" "No," I said. "I guess that's OK." By this time I was definitely very horny and even though they wanted to tie me to the bed, any chance of having them masturbate me was a chance worth taking. Cindy went to her backpack and pulled out two new packages of rope. "I bought these just in case we needed to tie down the equipment for the trip," she said, "but it looks like we can use them right now. Stretch your arms out to the side, and we'll tie them to the sides of the bed frame." Elaine and Cindy each grabbed one of my arms as I stretched them out. Elaine started to twist my arm just a little and then stopped and said, "Wait a minute. This isn't going to work very well." I didn't see what her problem was so I just laid there. After a second she said, "Cross your arms across your body." So I did. "That will work much better," said Elaine and they proceeded to tie my crossed arms securely to the bed frame, pulling the ropes very tight. When they were finished I tested my bonds slightly, there was no way I was going anywhere. All I could do was to lay there and let them have their way with me, and that's just what I really wanted - then. Cindy walked around to the foot of the bed and said, "We might as well tie his legs apart too, so we can have total access to him. We wouldn't want him to accidentally kick us while we're working on him." So they each used the remainder of the rope and stretched my knees apart as wide as they could, tying them and my ankles to the bed frame along with my arms. I was spread wide and open for them. There was no way I could move, and I was definitely ready for them to get on with it. "Look how big he is now," Cindy said. I was definitely very horny by this time, and could feel my member straining. "Don't worry, she continued, "We'll take care of that for you. Elaine, why don't you get started on his hands, while I get something for our 'friend' here from the kitchen." "Good idea," said Elaine. "Get started on my hands?" I asked. "Don't worry about it," she said. With that, she got a nail file and some bright red polish out of her purse, sat down on the floor, and started to shape and polish on my fingernails. Now I knew why she wanted my arms crossed over my body. If they had been just stretched out to the side, my hands would have been turned the wrong way and she wouldn't have been able to get to my nails. "Why are you polishing my nails?" I asked. "Because I want to!" she said. "Now just shut up and let me do this!" Cindy was certainly taking her time in the kitchen. At one point, I thought I heard the blender, but I wasn't sure. When she finally came back, she was carrying a large bowl of crushed ice in her hands. "I crushed some of this so we can pack it around better" she said. This was definitely not what I had in mind for them to do to me when they told me they were going to get rid of my bulge! "No!" I screamed. "Don't!...Don't!" "Quiet!" was all she said and with that, she upended the bowl right over top of my hard-on. "This should shrink it down to size, don't you think so Elaine?" Then she proceeded to make sure that the ice was firmly packed around every part of my suddenly shocked cock and balls. "Take it off!" I screamed. "Take it off! It's cold!" "No," Cindy said. "That ice is going to stay on there until we're ready to take it off." "What are you doing to me?" I asked with tears starting to form in my eyes from the stinging cold of the ice. "We're getting rid of your bulge... and we're doing your nails for you." Elaine said calmly. "Now shut up and hold still, that ice isn't coming off until we're done with your nails, and if you keep squirming, it's just going to take that much longer." "You didn't really think we were going to both sit here and masturbate you did you?" Cindy said. "You know perfectly well that I wouldn't do anything like that." What could I do? I couldn't move, I wanted the ice off me just as soon as possible, so I kept taking some deep breaths to calm myself, and just laid there trying to be as still as possible. When Elaine finished with one hand, she gave the nail polish to Cindy and Cindy did my other hand. Occasionally, one of them would check on the ice to make sure it was still firmly touching every inch of my cock and balls. "Look how small he's getting." I heard Cindy say at one point just before she repacked the ice tighter than before. One thing was for sure. I wasn't hard any more. The ice was so cold, that I had tears in my eyes. Occasionally, I would plead for them to take it off, but they both just said "No!" When they finished with both of my hands, they started on my toenails. By this time, the ice wasn't hurting as much anymore, my cock and balls were becoming thoroughly numb from the cold and thoughts of frostbite were running through my mind. Finally, they were finished with my toenails and Cindy said, "OK, I think it's time to get rid of the ice." I can't tell you how happy I was to hear that! When the ice was finally gone, Cindy said, "look Elaine, it looks like the ice did most of the work for us." "It sure is small now," said Elaine, "it's hard to believe what it looked like just a little while ago." "Please, can I get up now," I said. "You've done what you wanted to me, and it's real small now, so please untie me and let me up." "Oh, we're not quite done with you yet," said Cindy. "What are you going to do?" I asked, becoming more concerned again. "We've got something in mind that will keep it from showing under your skirt for quite some time," she said. "Remember that trip Elaine and I took to New Orleans this summer? Well, while we were there, we had a long talk with some of the professional female impersonators there and one of them showed us a really good way to keep that little thing hidden. We've been just aching to try it out on you and finally decided that this would be the perfect time." "What are you going to do?" I asked. "You'll see," she said, and with that she started poking and pulling on my balls and penis. I couldn't really see what they were doing very well and I couldn't feel a whole lot down there either since the ice had numbed everything pretty well. At one point I saw Elaine hand Cindy something, but I couldn't see what it was. "Oh!" I heard Elaine say at one point, "This is working great! I think this will work out much better than the way that impersonator told us he did it." "I think you're absolutely right," Cindy said. "This is going to be perfect!" A few seconds later Cindy finally said, "All done!" All I could feel down there was that it felt "different." I certainly didn't hurt anywhere, but all I can say is that it didn't feel normal. "I think we can untie him now and let him up," Cindy said. Welcome sounds to my ears! They untied my feet and knees first, and let me tell you, it felt so good to be able to move and close my legs together. When I did though, I noticed that it felt different to close my legs together. Something was missing. My balls were no longer in the way. Whatever they had done to me, my balls were no longer between my legs. As they were untying my hands, Elaine said, "You know, I think we should keep his hands tied so he can't undo what we did to him yet. I don't think it will come apart, but maybe we better not take the chance." "You're right," Cindy said. "Good thinking!" She looked at my bound crossed arms for a second and said, "I think I have an idea." She took some of the rope that had been around my legs and tied my arms together right where they crossed. "Ok," she said, "untie the rope from the bed frame, but leave it tied to his wrists." As soon as the ropes were free she said "Sit up," which I did gladly. The instant I was in a sitting position, Cindy grabbed the ropes that were still attached to my wrists and wrapped them all the way around me pulling them tight, so that I was essentially hugging myself. She brought the ends in front of me, and tied them off there. My arms were useless! "OK," she said when she was done. "Lets get you dressed again." "What did you do to me?" I asked. "We'll show you in a few minutes." Cindy answered. "I want to see how it looks with your clothes on now." I stood up, finally, and Cindy helped me into my panties pulling them up tight. She suddenly let out a little scream of delight and said, "This is fantastic! You can't tell that he has anything there at all!" "I can't believe it," said Elaine "it worked great!" "What did you do," I asked again. "Here, let me show you," said Cindy finally. They led me over to my full-length mirror and let me look. I could see no sign of my cock and balls at all, just a totally smooth front in the crotch of my panties. "What did you do?" I asked again for the umpteenth time. Cindy pulled my panties down to my ankles and I spread my legs to try to get some kind of view of their handy-work. All I could see was a little mound where my penis should have been. I could see no sign of my penis at all. "How am I going to pee?" I asked. "Don't worry," said Elaine "the very tip of your penis is still sticking out, it's just stuck backwards where you can't see it right now." Cindy finally started to explain what they had done to me. "That female impersonator told us how to 'tuck,' as he called it, your cock and balls away so they're hidden. The only difference is that he used tape to hold everything together. Elaine came up with the brilliant idea to use superglue to hold everything together instead. And as you can see, it's working really well." "Superglue!" I cried. "How am I going to get it apart?" "You'll just have to wait till it comes apart by itself." She answered. "How long will that take?" I asked. "I have no idea," she answered, "we'll just have to see. In the meantime, you're certainly 'not' going to have to worry about any hard- on showing through your clothes. In fact, I guess you're not going to have to worry about having any hard-on, period!" Cindy and Elaine both started laughing at that. I was still in too much of a state of shock. The two girls finished getting me dressed helping me on with my pantyhose, skirt, and shoes. Then Cindy sat me down and got out her makeup. "Cindy," I said, "do we have to do makeup too right now?" I asked. "Of course," she answered. "We can't have you going on out today dressed like you are with no makeup on." "Going out!" I exclaimed. "Cindy, I can't go out dressed like this! You know that. What would everyone say?" "Don't worry," she said, "I already warned everyone that you would probably be dressed up today, so they're expecting it." "But Cindy, I can't do that! I just can't!" I cried. "Hush!" she said. "I'm not interested in what you think you can or can't do," she said. "You 'can' do it, you 'will' do it, and you are 'going to' do it! Now shut up, and hold still while I do your makeup up for you. Elaine, I think that maybe we should leave his arms tied up until we get under way later. That way, he'll realize that he has no choice in this matter!" "Good idea," said Elaine. "While you're doing that, why don't I rustle us up something for lunch." I just sat there while Cindy put the makeup on me. My mind was racing, but not with any coherent thoughts. I was panicked. I was excited. I was still in a state of shock from everything that I had been through so far. This was not shaping up to be your typical day! I flat out didn't know what to do, so I did the only thing I could do, I sat there and let Cindy do my makeup. Besides, with my arms still tied like they were, I didn't really have much choice. After the makeup, Cindy put some clip-on earrings on my ears, a pretty heart-shaped necklace around my neck, and fastened a tennis bracelet around my right wrist. When she finished, she led me back over to the mirror to show me what she had done. She had gone lightly with my makeup. It was tasteful, but not overdone at all. When I looked at myself, I saw just what I really looked like. For the most part, I looked like a girl, but without my wig, you could tell immediately that I was a guy. "Can you put my wig on me?" I asked. "I still look like a guy without it." "Maybe later," she said. "Right now, let's go get some lunch." "Can I go to the bathroom first?" I asked. "With all this excitement, I really have to go." "Ok," she said. "It will probably be a good thing to make sure you don't have any problems with that. There shouldn't be, but we should make sure anyway." Just what we were going to do if there were problems, I didn't know. Cindy led me into the bathroom and stood me in front of the toilet. I waited for her to untie my arms, but instead she quickly pulled up my skirt, pulled my pantyhose and panties down to my ankles, and sat me down on the toilet. I was surprised and when I looked at her she said, "Well how else are you going to be able to pee now? You can't very well stand up like you usually do anymore, can you?" She certainly had a point. Peeing, fortunately, turned out to be no problem. I just sat there, relaxed, and it all just came out. I was embarrassed at having Cindy right there in front of me watching, but there wasn't much I could do about it. When I was through, she took some toilet paper, wiped what little of me that was still exposed, and pulled my clothes back up. "Well, at least it's good to know that there won't be any problems with that," she said. "And it looks like you're going to have no choice but to pee like a girl for a while too. This is certainly going to make things a little more interesting for you for a while." During lunch, they took turns feeding me little bites of a sandwich and holding a glass of coke up to my lips so I could drink. "Don't bother cleaning this up," Elaine said to me afterwards. Very funny, I thought, with my arms tied there wasn't anything I could pick up anyway. After lunch, they took me back into my bedroom. Cindy sat me down in my desk chair and went over to my luggage that I had packed the night before. She opened my suitcase and then just dumped everything into a pile in the corner. She went through my stuff and pulled out my toiletries and all the men's underwear I had bought. The underwear she put in her backpack along with the pair I had on earlier. Then she and Elaine went through my closet and all of my drawers pulling out every item of female clothing that I owned and together, they decided what to pack for me. It suddenly dawned on me, that they were only packing girls clothes, none of my male clothes at all. When I asked them about that Cindy said, "That's right. You're going to make this whole trip with 'only' girl's clothes to wear - the entire weekend!" I thought I was scared before, but this was worse. How could I spend an entire weekend dressed like a girl? "Cindy, I can't do that!" I said again. Cindy didn't even look at me, but just said, "I told you, I'm not interested in what you 'think' you can or can't do. You 'are' going to do it, whether you like it or not." When they finished packing, Cindy said, "Just one other thing." She went to her backpack and pulled out a purse. "You're going to need one of these on this trip and since you don't own one yet, I'm letting you borrow one of mine." She then pulled everything out of the pants pockets that I had had on earlier and put everything in the purse. "There, all done," she said. "I think we're finally ready." "How about his wig?" Elaine asked. "I've been thinking about that," Cindy said. "I kind of like the idea that you can tell he's a guy as soon as you see him. This way, there's no chance of anyone mistaking him for what he really is." "Cindy," I said, "please, don't do this!" "We 'are' doing it, so stop complaining and get used to it." It wasn't too much longer before the rest of the band drove up in Tim's full-size van with the trailer attached. Cindy grabbed the front of my ropes, pulled me to my feet and propelled me toward the door that Elaine opened in front of us. "Noooo! Pleeease! Stop!" I cried. But Cindy just kept pushing. And suddenly, I was through the door and out in the open air. My safe cocoon was behind me and there was nowhere to hide. For some reason, I quit screaming as soon as I went through the door. Cindy kept pushing me right down the short sidewalk and all the way out to the van. I was scared and even though everyone there had seen me in my apartment while I was dressed before, I was very embarrassed. Tim, Stan, and Rog (Roger), our keyboard player, had all gotten out and were standing next to the van. "I can't believe you're really doing this," Tim said. I started to say something but Cindy got there first and said, "He's doing it!" Rog said, "You've got him tied up!" "We didn't want him to be able to back out and change his clothes again," said Cindy. "We can untie him as soon as we get out of town. Stan, you and Tim help Elaine with our bags so we can get going." "Sissy!" I heard Stan say as he walked past us. You have to understand that Stan is everything that I imagine I'm not. He is well over six feet tall and works out religiously so he's covered in muscle. He could easily enter a body building competition, something he says he's not really interested in. Of all the members in the band, he was the only one who seemed to resent my cross-dressing. I think it made him uncomfortable. When all of our luggage had been stuffed in the back of the van, Elaine walked over to me and said, "Don't forget this," as she took the purse Cindy had 'loaned' me and placed the strap over my shoulder and my head so it wouldn't fall off. Cindy said, "Ok, into the van," and pushed me toward the side door. Truth be told, I was ready to get into the van so I wouldn't be quite so visible. That's when I came across my first minor little problem. As I lifted my leg to step up into the van, my tight skirt stopped me. I tried three times to lift my leg that high to get in, but there was no way that skirt was going to let me. I felt everybody staring at me. With my arms tied around my body, there was no way I could lift my skirt to get in either. Finally Cindy came up behind me and lifted my skirt just enough to allow me to step up into the van. "Now you're finding out some of the things we girls have to go through all the time," she said. I scooted all the way over in the middle seat and sat down as best I could. Stan and Elaine got in the back seat, Tim and Rog in the front, and Cindy sat next to me. And we were off, leaving my nice comfortable, secure world behind. A few minutes later Cindy finally said "I think we can untie him now. Rog, will you help me out?" Rog turned around and he and Cindy finally untied me. While I was very happy to get my arms free at last. I also realized that I couldn't hide behind the ropes as an excuse for why I was out in public dressed the way I was. I really wondered how I was going to get through this. As soon as the ropes were gone, Rog asked me "Are you really going to spend the whole weekend dressed like a girl?" "I don't seem to have much choice in the matter," I said. "Cindy and Elaine made quite sure that the only clothes I have with me are girl's clothes." "I just felt it was finally time to get him out of the apartment and show him off to the world," Cindy added. And then she and Elaine spent quite some time describing, in detail, just what they did to me that morning. They even described just what they did to my penis and balls, how they tucked my balls inside my body and superglued everything so that it would all stay right where they wanted it to. "Superglue!" Rog said. "Geez! How long will it stay like that, and how's he going to pee?" "I don't know how long it will last," answered Cindy "quite a while I hope, or imagine. And as to how he's going to pee, well, he has to pee like a girl now, that's all." "Sissy!" I heard Stan say again from the back. A few minutes later Rog had another thought. "If he's going to be dressed like a girl all weekend, I think we should call him Donna instead of Don." "That's a great idea." "Good idea." "I like it." It seemed that the whole van was in favor of a new name for me. "I agree!" said Cindy after a minute. "But, you know, I'm not sure that Donna is the right name for him. I kind of think he should have a girls name, but one that's totally different than his boy's name." "What did you have in mind?" Tim asked. "I honestly haven't thought of it before," Cindy said. "Anybody have any suggestions?" There were a few suggestions thrown out by various people in the van and all were considered. Some were liked better than others. Fortunately, no one asked me, and I just kept quiet during the whole thing. It was bad enough what they had done to me already, I didn't really want to be an active partner in making my life worse. That was when Rog added another thought (I was really beginning to hate him). "You know," he said most parents pick out a boys name and a girls name before their baby is born. I wonder if Don's mother ever told him what girls name she had picked out for him." "Well Don," said Cindy, "did your mother ever tell you if she had a girls name picked out?" This caught me by surprise and I had to think for a minute. "Actually," I finally said, "I do remember her telling me once that if I had been born a girl, I would have been named Karen, after her Grandmother." "I like it," said Elaine. "Me too," said Rog. "It's perfect," said Cindy. And so I was dubbed Karen. "Say hi to everyone Karen," said Elaine. "Hi," I said unenthusiastically. "No," Elaine responded, "I want you to say 'hi' and tell everyone your name." I didn't say anything and just kind of hung my head too embarrassed to know what to do. "Do it!" she egged, "do it!" "Do it!" echoed Cindy. So I plucked up my courage and said softly "Hi, my name is Karen." "Do it again!" said Cindy, "louder!" "Hi, my name is Karen," I said again so that everyone could hear me better. "Again!" commanded Cindy. "Hi, my name is Karen," I said for the third time. "Hi Karen, it's nice to meet you," said Cindy finally. And immediately I was greeted with a chorus of "Hi Karens" from around the van - and one quiet "Sissy!" from Stan. From that point on, the only name they called me was Karen. Part 3: "Oh Promise Me" It took a little longer to get to the club than we expected and we didn't arrive until almost 4:30. As we drove into the parking lot, Cindy reached into her purse and pulled out her lipstick and a small mirror. She looked over at me and said, "You too, Karen," "we want to look our best now, don't we. I'll lend you my mirror when I'm through." So I reached into my purse and pulled out the lipstick that Cindy had put in there earlier. Cindy handed me the mirror and I went about touching up my lips. It was the first time I had ever tried to do this with a small compact mirror. It didn't show my whole face like I'm used to and I think I was going cross-eyed trying to see. Cindy had us drive around back and park near the loading doors. Then she got out and went looking for the club's manager. When she came back, she said, "the doors are open, lets get set up." This was it. I was out in public. There was no place to hide. People were going to see me, and I was going to have to talk to people. I was very nervous, but what could I do, there was nowhere to go. As we walked into the club to look at the layout, Cindy came up to me and said, "I told the manager about you, so you don't have to worry, he knows. Now, there's a little sound booth area against the wall over there for your stuff. The manager said he'd find you there and show you the rest of what they have available." I walked over to the area she indicated and took a good look. The sound booth had a low wall around two sides of it about waist high. There was a table in it for my equipment and I could see a patch panel built into the wall. A few seconds later, the manager came over to see me. He looked me over carefully as he approached, but when he arrived, he was very professional. Something that forever made me like him. "Hi, he said, "I'm Tom Murphy. You must be Karen." Being called Karen like that for the first time sent a jolt of electricity through my system, but I didn't let it show. I was resolved to try to be the best, most professional sound "person" that I could, no matter how I was dressed. That was the only lifeline I could think of to help me get through it all. Mr. Murphy showed me all they had to offer, which was really pretty good, and we discussed what equipment I had and the best way to set everything up. Despite being dressed the way I was, it was nice to talk to a real professional who knew his stuff. Never once, did he mention how I was dressed. He just accepted me as I was and we got down to work. When we finished talking, I went looking for the men's room before I went to help unload the equipment from the trailer. As I was going in, Tim and Stan were just coming out. "Maybe you should be using the ladies room," said Stan. "Very funny!" I said, and pushed on past them. After that, I went out to help get my stuff. Tim was in the trailer and handing everything out to Rog who just put everything on the ground behind him. Everybody else just picked up a box and carried it inside. Every single piece of equipment that I owned was heavy, and I immediately found out that a skirt was not the best thing to wear for that kind of work. The tight skirt made me keep my knees together every time I stooped down to pick up something, and even though my shoes had wide heels, they were high enough to make carrying something heavy a little more difficult. I was very aware that my movements were, of necessity, more feminine than they usually would. We managed to get set up pretty quickly and for once, everything worked the first time. The band went through their usual sound check pieces and I walked around the club while they played, listening for any sound problems that I could fix. The club had pretty good acoustics and when we were finished, the manager called over, "Sounds good!" Before we left, Cindy told everyone that she was going to get the motel information from the manager and asked us to meet her at one of the tables. When she got back, we were all standing around the closest table to the stage. "Ok," she said. We've got three rooms set up at the Holiday Inn just a couple of blocks from here. Mr. Murphy says it's a real nice one. Before we go, however, we have a little piece of business to take care of, so please bear with me for a minute. You all know that Karen here has been a cross dresser for quite some time and you've all been to his house and seen him dressed. Last year, I got him to promise me that he would always wear panties and would never wear men's underpants again. When we were dressing him this morning we found him wearing these," and she reached into her purse and pulled out all three pairs of the men's underpants I had bought. "Karen, come over here!" she commanded. I didn't know what to expect, but knowing Cindy, it wasn't going to be good. She reached into her purse again and handed me a pair of scissors she had taken from my desk drawer. "We are all going to stand here until you cut up every pair of these underpants into little pieces and while you're doing it, I want you to continuously promise all of us that you'll never try to buy or wear men's underpants again!" My mouth just hung open. I couldn't believe she was asking me to do this in front of everyone. Elaine said, "You broke your promise Karen, now take your punishment and get on with it so we can get out of here." "Yeah," said a few other people. "Hurry up." I could see they were all impatient to leave, so I picked up the scissors and the first pair of underpants and started cutting. I cut through the waistband, the crotch, and the waistband again while I recited, "I promise to never buy or wear men's underpants again." Then I repeated the whole procedure with the second and third pair. I was thoroughly embarrassed and humiliated. Now they all knew that I didn't wear men's underpants, and never would again. Finally I finished, and Cindy just said, "Ok, we can go now." The only other comment I heard was a small "Sissy!" from Stan. When we got to the hotel, Cindy went in to the front desk and came out a few minutes later with our keys. All the rooms were in the back on the second floor. We drove around and parked as close as we could to the nearest stairway. As we grabbed our bags, we decided to meet again in 15 minutes to go find something for dinner. After Cindy and I got to our room, and had a chance to talk for a minute I said, "Cindy, I don't think I want to go out to dinner. Can I stay here and have one of you just bring me a hamburger?" "Absolutely not!" Cindy answered me. Then she softened her tone and gave me a big hug. "I know that this is hard on you and that you're doing all this against your will. But you know that this is also something that you've always dreamed about doing, haven't you. So please, why don't you try to take the best advantage of this opportunity and get into the spirit of it all. Enjoy yourself and have some fun. You're going to be dressed like a girl for the whole weekend, and I'm not going to let you hide anywhere, so you might as well pretend to be just one of the girls and enjoy yourself." I could see she was right. I really didn't have much of a choice. It was going to be very humiliating, but since I was going to be humiliated anyway, I might as well make the best of it and try to enjoy it as much as I could. "Ok," I said finally, "I'll try." "That's the spirit," she said, "now let's get something to eat." So I put a smile on my face, grabbed my purse, and we headed out the door. I resolved that no matter what, I was going to try to enjoy this as much as possible. It was the only decent attitude I could take. Tim had found out that there was a mall not too far away and we eventually wound up at a Denny's restaurant just outside of it. I walked into the restaurant acting like there was nothing wrong with me and that everything was totally normal. I know I was getting lots of looks and stares but I just ignored them all, kept smiling, and pressed on. When the waitress came over to our table, she just looked at me and said "Don't you look cute!" and then just took our order. During dinner, Elaine brought up the fact that she really wanted to spend the next day shopping at the mall. Tim and Rog said they wanted to visit some of the music stores around town. In the end it was decided that the three boys would go poking around whatever music stores they could find but they would drop "us girls" off at the mall first. They would pick us up later in the afternoon. Cindy and Elaine were certainly making sure that I was going to get as much public exposure as possible. Just before we left the restaurant, I decided to exert my new found feminine attitude and without being told, reached into my purse and pulled out my lipstick. "Can I borrow your mirror again?" I asked Cindy. As I refreshed my lips, Elaine finally said, "You've been smiling and acting like you're enjoying this since we left the hotel. What gives?" "Cindy just convinced me that since I really don't have a choice in the matter, that I might as well try to enjoy myself as best I can," I replied. "So I'm trying to do just that." "Good!" said Elaine. "I think we'll all enjoy this weekend so much more." When we got back to the hotel room, Cindy told me to get undressed and to shave so that when she redid my makeup, my face would be nice and smooth. While I did that, she was busy unpacking and laying out what we each would be wearing for the evening. Cindy always made it a point to look as sexy on stage as possible. She never had a problem doing it! When I got out of the bathroom, she said, "I laid out some things for you to wear tonight." On my bed were some shiny pantyhose, my black bra and matching panties, and one of her dresses that I had seen her wear on stage several times. "Why can't I just wear what I had on earlier?" I asked. "For heaven's sake!" she said, "a girl always wants to look her sexiest whenever she goes into a club like this. Besides, I think that dress will look really good on you." The dress was all black and very fitted with a zipper up the back. It had short sleeves, a small mandarin neck with a teardrop shape cutout between the neck and the bust, and had a very, very short skirt. "Since you obviously can't go braless, I tried to pick out something you could wear a bra with," she said. "Oh, thanks," I said. Actually, I couldn't wait to try on the dress. Cindy always looked great in it. I hoped it would look good on me too. I started dressing while Cindy put her hair up in some hot rollers she had plugged in. "Don't put the dress on yet," she told me, "wait till after I do your makeup." So I put on my matching bra and panties and filled the cups with my breast forms. The pantyhose were really different than any I had ever worn. They were very shiny and glistened all over. I knew that they would really focus attention on my legs, especially in that short skirt. The shoes Cindy had picked out for me were mine. They were something I had indulged in for myself last year from a catalog sale, but had only worn just a couple of times and only for short periods in my room. They were patent black sandals with thin soles and very thin straps. They also had very high, very narrow heels and were not easy to walk in. As I buckled them onto my feet, I knew that walking in them was going to be tough - all night. "Aren't you glad you finally have a chance to wear them?" Cindy asked. "Actually, I am," I said as I realized she was right. By the time I got my shoes on and had taken a few steps in them to try them out, Cindy was ready to do my makeup. With her hair full of large rollers, she sat me down in a chair and proceeded to do my face completely. I could tell she was using a lot more makeup than she had earlier. When she finished, she said, "There, what do you think?" I turned and looked in the mirror and saw that she had gone very dramatic with it all. My eyes looked huge with big, long lashes, my cheeks were heavily accented, and my lips were full and very red. I realized that this time, the lipstick she used matched the color on my nails. "Wow," I said, "I look great! Thanks!" "You're welcome," she said. "Now finish getting dressed and put this in your purse" and she handed me the lipstick she had just used on me. I put the dress on and managed to get the zipper zipped up with only a moderate amount of difficulty. I had done that before. As I looked myself over in the mirror, I realized that it was a shame Cindy wasn't allowing me to wear a wig. Despite the clothes and Cindy's expert makeup job, with my boy's haircut, there was still no way you could ever mistake me for anything other than a boy dressed up like a girl. It was going to be a long night. Cindy's dress was a shiny silver mini-dress that I had seen her wear before. She certainly wasn't wearing a bra with it. Most of her breasts were exposed. Very sexy! The band was supposed to start playing at 8:00 and we left the hotel around 7:30. As I walked out of the room, I realized that the shoes I was wearing were forcing me to walk with a really feminine sway to my hips. If I wanted to get anywhere in those shoes, there was no way around it. Oh well, I thought, I'm wearing a dress anyway. Going down the hotel steps was another unique experience for me, believe me, I took them very slow and carefully. "We'll have to get you a little more practice with stairs," Cindy said teasingly. When we got to the van, I got the usual "look-overs" from everyone, only maybe a little more so this time. Elaine said, "You look very nice tonight." What could I say except, "Thank you." When we got to the club we went in the back door again. "This is it," I thought to my self. "Here we go," and I mustered up my courage and foraged across the room to the sound booth. The club was starting to fill with people and the music system was playing one of the latest top 40 tunes. As I walked across the room, I was very aware of everything. I could feel how short my dress was and how my legs were completely on display. I could feel my heels hitting the floor with every step and even though I couldn't hear it over the sound system, I knew they were making a very distinctive clicking sound. I could feel everyone in the room watching me. When I got to the booth, I stowed my purse under the table and busied myself with turning on and checking out my equipment. I saw Mr. Murphy over by the bar and he nodded to me and smiled. I smiled back and then sat back on a bar stool that had been placed in the booth for me. A few minutes later, a waitress came up to me with a strawberry daiquiri on her tray. "Hi," she said, "You must be Karen." I just nodded. "Mr. Murphy sent this over for you. He said you would probably need it." "Thank you," I said as she set the drink on the top of the wall. "He may be right." "I can't believe you came here dressed like that," she said. "Do you do that a lot?" "Actually," I explained, "this is my first time out in public. I do dress up at home a lot, but this time, my friends thought I should get out of the house, so to speak." "Well, good luck tonight. If you need anything, just ask me." "Thanks," I said again as she left. The band was scheduled to play from 8:00 to 1:00. They usually played for about 45 minutes and then took a 20-minute break between sets. The crowd loved them from the moment they started. I never had any doubts about that - they were good. As the night wore on, the room got more and more crowded, and as usual, I started pushing up the volume more and more. Every time I run sound for them, I always seemed to have my own group of "sound-groupies" around me, and that night, there seemed to be more than usual. I spent a lot of time talking to people and explaining that while I liked to dress like a girl, I didn't dress that way all the time. I wound up being completely honest about myself with everyone and actually managed to relax and enjoy myself. Cindy was right, this was a dream come true experience for me, and letting myself enjoy it was the best thing I could ever have done. About half way through the evening, Cindy came back to my booth to see how I was doing. The band had started a three-tune set that featured only Elaine, and Cindy had some time to leave the stage. "It looks like you're doing pretty well," she said. "I am," I replied. "I took your advice and I'm actually enjoying this." It was at that point that one of the guys I had seen drinking back at the bar came up to me and said, "I want you to dance with me." I was stunned. "I'm sorry," I replied, I don't do that. Besides, I'm working." "I said, I want you to dance with me!" he said again more forcefully. He was certainly rude. "Oh, go ahead and dance with him," said Cindy. "I'll watch the board for you and this will be a new experience for you. Every girl likes to dance." "But Cindy," I started. I didn't get to say anymore because the guy grabbed my arm and pulled me out of the booth onto the dance floor. It was easy to see that he was more than a little bit drunk. We had just started dancing to the very upbeat tune when it ended. Good! I thought to myself, I can get out of this now. But the band went right into the next song, a slow one, and he grabbed me and pulled me close up against him. He put both his arms around my back like he was hugging me and I had nowhere else to put my arms except around his neck. I was very aware that even in my high heels, he was taller than I was. He "led" me around the floor in a clumsy fashion. Of course I wasn't helping matters any with my inexperience at dancing in high heels. Having someone else in control and going backwards all the time is a unique experience, let me tell you. He also kept trying to grind his pelvis into mine and I could definitely feel he had a hard on. When the song finally ended, he said "Thanks," and then just left me. I walked back to Cindy at the booth. "Did you enjoy it?" she asked. "He was rude!" I said. "I don't think I ever want to do that again." "You win some, you lose some," she said. "I have to get back. Glad to see that you're enjoying it." Around midnight, I had to pee pretty badly. I had been holding it for quite a while since I was a little bit concerned about going into the men's room dressed like I was and I wasn't sure how I would be accepted in the ladies room. As soon as the band started their last break, I couldn't wait anymore and headed for the men's room. There were a few guys in there who all just looked at me as I went into one of the stalls to sit down and relieve myself. When I came out, and started to wash my hands, the guy who had danced with me was standing right there. "Are you a boy or a girl?" he asked. "I can see you're a boy, but I danced that whole tune with you and tried my best to get some kind of a rise out of your cock, but I couldn't even feel a cock on you. Maybe you should show me what you have under that dress honey, and then maybe you should suck my cock for being so nice and dancing with you." I was suddenly real scared. "No! Go away!" I said. Suddenly he just grabbed me and started trying to pull up my dress. Trying to fight him off was not easy since he was bigger than I was and those heels were keeping me off balance. It was then that I suddenly saw Stan coming around the corner of the stalls where he must have just finished peeing. "Stan," I called. "Help me!" I don't even think my attacker heard me because he was just intent on trying to get my dress up. Two seconds later, Stan pulled the guy off me, and I had the pleasure of seeing Stan literally throw him across the room, an awesome display of Stan's strength. "Get out of here!" he yelled at the guy. And a moment later, my attacker was running out the door. "Thanks Stan," is said, "I really appreciate it." "What the hell are you doing in here anyway!" he said. "You don't belong in here. That would never have happened if you had stayed out. Now get out!" For some reason, he was very angry at me. So I walked out with him practically pushing me all the way. We went out back, behind the club where there was a small "break" area with a picnic table. The rest of the band was already out there enjoying the cool night air. "What happened to you?" Elaine asked as soon as she saw me. "You're all messed up!" So I related the entire incident in the men's room to them. "If it wasn't for Stan," I concluded, "I would have been in deep trouble." "He should never have been in there in the first place!" said Stan angrily. And then something in Stan just snapped! "And I'm going to make sure it never happens again!" And with that, he suddenly reached out and grabbed the hair on the very top of my head in his big fist. "Ow! Stop!" I cried, grabbing his big arm with both my hands trying to fight him off. Suddenly, I was tripping and stumbling backwards as he propelled me by my hair, until I bumped up against the cement wall. Then he banged my head against the wall. "Do I have your attention now?" he asked. I could hear everybody else shouting at him to stop. "Stay out of this!" he commanded them. "What happened tonight should never have happened, and I'm going to make sure it never happens again! Now sissy," he said, "lets get some things straight. Do you wear panties?" he asked. "Yes," was all I could say. I was scared, his grip on my hair was hurting me terribly, and all I could do was to hang on to his big arm and hope he wouldn't hurt me more. "Do men wear panties?" he asked next. "No," I answered. "Do sissies wear panties?" "Yes," I said. "Do men wear dresses?" "No," I answered again. "Do you wear dresses?" he asked. "Yes," I answered. "Do sissies wear dresses?" "Yes," I said again. "Do men stand up to pee?" he asked next. "Yes," I said. "Do you stand up to pee?" "I can't," I said. "Do sissies sit down to pee like a girl?" "Yes," I said. "Now let's be perfectly clear ab

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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

2 years ago
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Saturday Morning Sissy

Saturday Morning SissyI woke late on Saturday morning and immediately knew that something waswrong. Sure, I'd been out drinking Friday night, so the hangover wasn'tunexpected. But I was surprised to wake and find that there was aleather band snapped tightly around my balls and that this was tetheredsecurely to the foot of my bed with a short chain.Further exploration revealed that my entire body had been shaved and mynipples had been marked with some type of semi-permanent red dye. Ifthat...

3 years ago
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Saturday Morning Sissy

Saturday Morning Sissy I woke late on Saturday morning and immediately knew that something was wrong. Sure, I'd been out drinking Friday night, so the hangover wasn't unexpected. But I was surprised to wake and find that there was a leather band snapped tightly around my balls and that this was tethered securely to the foot of my bed with a short chain. Further exploration revealed that my entire body had been shaved and my nipples had been marked with some type of semi-permanent red...

2 years ago
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Revenge of The Sissy

Revenge of The SissyA big fat dirty pig dad abuses his sissy too much. I come home from work in my uniform from the garbage company, work shoes, and Hat. I head towards my recliner. I say you fucking sissy get over here. Get me a beer. Where's my remote? Where's my god damn dinner?I take my belt off and set it beside my recliner. I take my pants and uniform top off. I take my cigars out of my shirt pocket and set them beside me. I hang my pants and shirt over the back of my recliner. I set my...

3 years ago
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I Sissy

I, Sissy By Cassandra Morgan The late-night glow of the computer screen was the only sign of life in the house. Molly had long since gone to bed, alone. It was 3 a.m. Casey Matthews knew he should get to sleep. But he wanted to read one more fiction, get to one more situation, feel the stirrings from one more author. This was story time for Casey. His hand dropped and rubbed himself, just for a minute. He wasn't going to masturbate, not with Molly in the next room. But shifting...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

1 year ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

1 year ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

2 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

1 year ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

3 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

2 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

1 year ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Three - Birth of a...

2 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

1 year ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

1 year ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

3 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

3 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

1 year ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

3 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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