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No sex in this story. May be archived on any not-for-pay site. Petticoated Boy by Princess Pervette When I was a boy my mother used to dress me up as a girl. It started one day when I was five. I had been visiting a pal in another apartment in our building, and we got to playing with his sister. It was one of those rainy days when you're at loose ends and bored, and we played with her because we couldn't think of anything better to do. Anyway, she wouldn't let us play with her unless we played with her dolls. Then my mom came to get me, for some reason or other, and she found the three of us with Beth's dolls. She was furious beyond all reason. "What kind of sissy are you?" she asked as she pulled me by my ear down the hall to the elevator. And when we got home she said that if I liked playing like a girl so much, she was going to dress me up as one. I kept telling her it was Beth's idea, that she had pushed us into it, that I didn't really like playing with dolls. I said I hated playing with dolls. Nothing I said made any difference. Looking back on this as an adult, I think she had some kind of kink in her nature. Her punishment was all out of proportion to my offense, and I suspect she liked the idea of petticoating me and simply seized on this incident as an excuse. I didn't know whether she was bluffing or not when she said she was going to make me wear girls' clothes. It seemed to me like the worst thing that could ever happen to a boy, and I told myself that she couldn't really mean it. But another part of me knew that Mom always meant what she said, and I had a terrible night that night, lying in bed and dreading the next day. I was in kindergarten then. And when I got home after school, Mom took me right into the bedroom. Hers and Dad's bedroom. She had been shopping that day, and she had gotten some panties, a little slip, and a couple of little girls' dresses. I started crying and begged her: "Please, please, please, don't! Don't make me wear those things! Nooooo!" She was implacable. "You put those things on right now," she said, "or when your father gets home I'm going to tell him you play with dolls, and then you'll really get it." I was crying all the time I took off my clothes. I cried as I pulled on the pair of pink little-girl panties she handed me. "Go on," she said, "put on those panties and wear them like the girl you are!" I cried as I put on the little pink slip. "There you are," she taunted me. "Dressed in your girly panties and in your girly little slip." I cried as I put on the dress. I remember it was a white dress with all kinds of little frills and ruffles on it. "Now you're my little girl. Look at yourself in the mirror and see what a girl you are!" She made me stand in front of the mirror. I was a fright: a little boy, very obviously a little boy, in a frilly white dress, sobbing, my face wet with tears. She sent me to my room. As I crept off, her voice followed me. "Don't you DARE take those things off, or you'll get the beating of your life!" I lay on my bed and whimpered. What would Dad say when he came home and saw me this way? That would be worse than if she told him about Beth's dolls. In fact, I'm sure she had no intention of letting Dad see me, but in my emotional state, I wasn't able to sit down and analyze the situation rationally. And indeed, about half an hour before Dad was due home, she came into my bedroom with my boy clothes and said I could put them back on. She took away the dress and things I had been wearing, and as I put my other clothes on, I hoped that would be the end of it. No such luck. The next afternoon, it was the same thing, and we had the same tearful scene, with me begging her not to dress me. But time has its own healing effect. You can't stay horrified for ever, and by the third afternoon, I had resigned myself. There were no tears, just a sullen silence as I changed. She noticed this. "My little sissy boy is getting to like his dress, isn't he?" I didn't dare shout at her, but I said "NO!!!" as emphatically as I could. But I refused to cry. Boys didn't cry; only girls did, and I made up my mind that I wasn't going to be a girl, no matter what she put me in. That was a Friday. Dad was home over the weekend, so I had two days in which I could wear my own clothes all day long. I spent Saturday afternoon playing ball with some older boys in the neighborhood. I had never been keen on sports, but playing ball was a boy thing to do, and I joined in with a will that day. I played very well, too, and coming home, I thought, with satisfaction, "There! I'm good at playing ball. I really am a boy!" But on Monday afternoon it started again. She had been shopping again, and she had gotten me little white shoes, some white socks, a little lacy petticoat, and two more dresses. My heart sank: this wasn't just going to be for a couple of days; this was going to go on for a long time. But, as I sat in my room looking at a picture book, I noticed how comfortable the dress and petticoat were. The satin of dress felt so smooth on my legs, and the fluffy petticoat.... No!! I thrust the thought from my mind. I wasn't going to admit that they were anything but horrible. I looked at the picture book; it was about how people lived in far-off lands. That wasn't masculine enough. I threw it down and found another picture book, full of locomotives. That's what boys read about. But that evening, when Mom let me change back, I noticed how rough my pants were. Nothing like as nice as... No!! I was a boy, and these were boy clothes, and these were for me. They were my kind of clothes. Nevertheless, although I wouldn't admit it to myself, I was beginning to like dresses--and after only four days of wearing them. Girls were yucky, I told myself, and girls' clothes were AWFUL! I hated them! Whenever I caught myself running my hands over the soft fabric of my dress, I jerked them away as if I had touched something red hot. The next afternoon, someone rang the bell. Mom answered the door; it was Pete, the boy from the other apartment, coming to see me. Oh, geez!...was he going to see me this way? As I cowered in my room, I heard Mom saying I had work to do at home and I couldn't play with him that day. She came into my room. "I should have let him see you this way," she said. "But to-morrow you tell him that you have chores at home from now on and that you won't be able to see him after school. You can see him on the weekend, but not after school." It was about that time that she started calling me her little girl. And instead of Don, she started calling me Donna. She would always have me change in their bedroom, and she would watch every move I made. And as I put on the panties and the slip, or the petticoat, and one of the dresses, she would taunt me: "Getting good at this, are you? You're a regular little girl, now." The first time she said this, I made a face and said "NO! I'm a BOY!" and she slapped me. "Don't contradict me! If I say you're a little girl, that's what you are." But my contradiction was addressed to myself more than to her. Her words had struck a nerve; I was beginning to like my dresses, and I couldn't admit this to myself. So when she said I was a little girl now, something deep inside me said Yes, that's what I was, and something else, closer to the surface and scared by this internal assent, repudiated it and made me answer NO!, not so much to Mom as to that inner voice. And I found I couldn't keep my hands off my clothes. I would find myself softly fingering the fabric, exploring the ruffles, or lifting my skirt up and feeling the silky smoothness of the slip. I would take my hand away, but then, when I was distracted, I would unconsciously put it back and start fondling my clothes again. Then, one day, after Mom had made me dress, I looked at myself in the mirror and started turning, left and right, and watching my dress swirl about me. That was neat. I liked it, the way it felt as the fabric wrapped billowed out while I was turning and the way it wrapped itself about me at the end of every turn. Then I caught myself and stopped. One afternoon, about a week after that, as I was coming home from school, I found myself wondering what Mom would have for me to wear that day. Would it be the pretty blue dress or that nice pinafore...? And I realized, with a shock, that I was *looking forward* to changing clothes. I was beginning to learn my letters, and the first thing I learned to write was my name. I would scrawl "DON" on the paper, or sometimes "DONALD." But one afternoon, in my dress--I remember, it was a pale blue dress trimmed with white lace--I wrote "DONA." I didn't know how to spell "Donna." Then, laboriously figuring out how the letters went, I wrote, "I AM DONA." My heart skipped a beat. I wrote it again: "I AM DONA." I went to the mirror and looked at myself. And I said, "I am Donna." And at last it came: I admitted to myself that I liked being Donna. Now, to this very day, as I sit here in a nice, comfortable, lacy peignoir writing this, I don't believe that wearing girls' clothes had made me like being Donna. You can't turn a boy into a girl just by putting him into girls' clothes. If there was a kink in my mother's nature, there was an answering kink in my own. These kinks just happened to be triggered by the incident with Beth's dolls. If that hadn't occurred, would something else have triggered it? I don't know. I'll never know. By that time Mom and I had started playing a game of tacit consent: I still pretended to her that I hated dresses, and she still pretended to me that she believed this and that she was only doing it to punish me. But the incident with the dolls was ancient history now. You don't keep punishing someone for something he did a year before. But she kept dressing me. Nothing was said--but she liked it and I knew she liked it. I liked it and she knew I liked it. Whether she had ever secretly wished for a daughter, I don't know. If she had, she never told me so. Now, when she had me dress every afternoon, she didn't act the angry mother. We were both calm. I would come home from school and go straight to my parents' bedroom, where she would be waiting for me with whatever I was to wear that day. And without a word I would undress and she would watch me as I put on that day's panties and slip and dress. Boys wore long hair in those days, and one afternoon when I had finished dressing, she put a pink ribbon in my hair and gave me a little kiss. "That's my pretty girl," she said, smiling. "Now run along and play." I swirled my dress before her mirror and ran off to my room. If my attitude was changing, hers was, too. Gradually the notion of punishment was fading and we were turning from stern disciplinarian and and rebellious child into a cooperative venture. And as I outgrew my dresses, she would buy more for me. She had a special place, in one corner of her closet, where she kept my things. Everything came out into the open between us one afternoon a couple of years after this had all started. "You're such a pretty girl, Donna," she remarked, smiling. "Yes, Mommy," I said, calling her Mommy instead of Mom. "I'm a pretty girl in a pretty dress." I paused a moment. "Are you going to keep getting nice dresses for me to wear? Please?" And she smiled and said, "For as long as you like, Dear." That afternoon, instead of going to my room, I sat in the living room in my dress, reading one of Mommy's magazines. It was a pink dress, as I recall, all covered with ruffles and lace. Underneath, I wore a pretty white slip, and, underneath that, pink little-girl panties. And every once in a while Mommy would look up from her reading and smile at me. Then, when she was beginning to cook dinner, she kept coming out of the kitchen to look at her little girl-boy in dresses. **** That marked a change in our relationship. Shortly after that, Mommy and I began exploring the wonderful world of femininity together. We went shopping one afternoon (I wore boy clothes; she never took me out dressed), and she took me into the girls' section of the department store. She showed me different dresses and all the different kinds of outfits that girls could wear. Some were for girls my age, but she also showed me what I would be able to wear as I got older. When we picked something out, Mom told the saleslady that she was getting a birthday present for my twin sister. And we went into the women's section, too. She showed me mannequins in nylon stockings and in tights. She showed me garter belts and bras. She could have modeled these things for me at home, I suppose, but she was always very modest at home and never let me see her otherwise than fully dressed. The mannequins had high heeled shoes, and as I looked at them, Mommy whispered to me, "Some day you'll be able to dress like that." And I smiled up at her and said, "Oh, yes, Mommy, I hope so!" I have a picture from about this time. It shows me wearing a dress full of ruffles. Underneath, you can just make out a pretty, lacy petticoat. I'm standing in our living room, with a beatific smile on my face, suffused with happiness, and you can tell that I've been twisting back and forth, making the petti flare out. It was about this time that Mommy started showing me how to move. How to sit (legs together and crossed at the feet), how to walk (little, mincing steps), how to pick things up (kneel, don't bend over), how to stand (hands behind my back, head tilted a little to one side), even how to use my voice. She was an observant woman, and she caught me on the minutest details. For example, when I waved to someone, I wasn't to wave my whole arm. The thing to do was hold up one hand and wiggle my fingers, instead. "I want my Donna to be a little lady," she said. "Don't you want to be a little lady, Donna?" I certainly did. I still played ball with the kids on weekends, and with them I was always all boy; but being a little lady was now an important part of my life. And I started wearing my panties underneath my boy clothes when I went to school. Once I even wore them underneath when I went out to play ball. I was too nervous wearing them, however, and my play was lousy that day, so I never tried that again. It's amazing that we were able to continue for so many years without my father finding out. We had a close call once. My father got sick at work and came home from the office early. I would have gotten caught in my dress if it hadn't been for the cat. The cat somehow knew the sounds my father made when he came down the hall to our apartment, and every evening when she heard him approaching, she would jump up and run to the door and start meowing. I was sitting in the living room, looking through one of Mom's fashion magazines, when she did this. I almost didn't notice. But then I saw him and thought, "She thinks Dad's coming home." And then I thought, "Oh, golly! Maybe he is!" I couldn't afford to take any chances; I ran to their bedroom at top speed, forgetting everything Mommy had taught me about how girls run, picked up my boy clothes, and dashed into my room. I got there just as my father was coming into the apartment. It was lucky that I was still too young to wear nylons, or makeup. As it was, I almost tore my dress getting it off. I pulled off the slip and put my shirt and trousers on over my panties. I stuffed the dress and slip into a dresser drawer. Then I remembered my little-girl shoes-- I remember, they were Mary Janes--I pulled at the straps and got them off. Then...oh, shit!...my shoes and socks were still in my parents' bedroom. I put on a fresh pair of socks, and just then Mommy came in. I explained about the shoes and socks, and she went and got them while my father was in the bathroom. That had been too close for comfort. Dressing made me much closer to Mommy. She had always been loving and affectionate, except when I made her angry, and I had always been fond of her. But now we two were girls together, and I loved her as never before. And my behavior was better, too; I rarely made her angry any more. My mother continued dressing me right up until I reached puberty. Then I think she must have felt it was soon going to be time to stop, because she changed the way she dressed me. Up until that time, I always wore clothes appropriate to a girl my own age, but now she started dressing me in older girls' clothes. If my dressing was going to have to come to an end, she wanted to squeeze in all the things we wouldn't be able to do later. Or maybe she wanted to keep the promise she made when we went shopping: "Some day you'll be able to dress like that." She bought me nylons and garter belts and showed me how to put them on. She bought me a bra and made breast forms out of little plastic bags filled with rice. And one day when I came home from school she was waiting for me and cried, "Surprise!" She held up a black thing all in satin and ruffled lace: it was a teddy! I rushed to put it on, hastily stuffing the breast forms into the cups, and looked at myself in the mirror. It was lovely! I liked it so much that I didn't bother to put on a dress. I just sat in the living room, reading in my teddy and occasionally looking down and marveling at how sweet my body looked, encased in that gorgeous black satin and lace. She taught me how to use makeup, too. She did that very well; as an adult, I've seen so many crossdressers who have applied makeup and haven't known when to stop. Mommy's first rule was, "The less, the better." This was frustrating for me, because naturally I wanted to slather everything on without restraint. She let me do that once, to show me, and when I looked at myself in the mirror, I saw how wrong it was. When I did it her way, I looked like a real lady. In fact, when I saw myself, I thought that, for the first time, I really looked like a girl. I liked that. It made me want to go outdoors dressed, but Mommy never let me do that. But I remember how sweet those afternoons were, sitting and reading in a pretty, full dress, sometimes with a frilly petticoat on underneath, lightly made up, with heels on my feet and a pair of earrings clipped on my ears. (She never let me get my ears pierced, because Dad would notice.) One month she gave me dancing lessons, and we whirled about the living room floor, I in my dress and Mommy in a pair of slacks. **** But all good things come to an end, and the first time she found a dry, crusty stain in my pajamas, she decided the time had come for me to quit. When she told me this, I believe I cried and begged more heartbrokenly than ever before, even more than I had that afternoon when she made me wear girls' clothes for the very first time. I wept bitterly as she took all my pretty dresses and bundled them up to take off to Goodwill. "Don," she said, calling me by my boy name for the first afternoon in as long as I could remember, "you can't go on like this for the rest of your life." "Why can't I? Why can't I go on being a girl?" "Because you're growing up. You're going to grow up to be a man. You'll grow a beard, and your...thing...is going to get bigger, and you'll be interested in girls yourself. And girls aren't going to want to date a boy who dresses up like a girl." "But why can't I change? Wendy Carlos changed." I had read about Carlos in a magazine, and I had wondered at the time whether I might some day do what she had done. But this was the wrong thing to say. She turned pale. "Don, don't ever, EVER say a thing like that again! Don't even *think* a thing like that!" She was seriously alarmed now. She must have wondered, for the first time, whether our childhood dressing games had gotten out of hand--whether they were going to turn out to be a prelude to a sex change operation. "No. If you're going to think of things like that, then this has to stop right now." I begged her to let me at least keep my panties. At least two pairs. At least one pair. But no: everything had do go. I was in the eighth grade now, too old to cry; but I cried myself to sleep that night. For the next two weeks I wore my boy clothes after school. And hated it. It was almost the mirror image of the time when Mommy had started dressing me: I hated my rough, heavy clothes. And sometimes, out of habit, I would run my hands over my trousers or my shirt and, feeling the coarse fabric, would jerk my hands away, just as I had once jerked them away from my girls' things. I shoplifted for the first time in my life the week after that. I was browsing in a variety store, saw, in a pile on a table, a pair of panties I couldn't resist, and quickly stuffed them in my pocket. I was lucky: I got away with it. That night I wore my panties to bed. The next time, I wasn't so lucky. Same store, same pile of panties. But as I was walking away from the table, I suddenly felt someone taking hold of me by my collar. It was the manager; he spoke to me roughly and made me empty my pockets. Then they called my mom. There was hell to pay, of course. Mommy threatened everything but telling my father, which she didn't dare do if she didn't want the whole story to come out. But I suppose that, in the long run, it was good that I got caught, because she realized that this was a thing she couldn't stop. She had tried to turn off my crossdressing as abruptly as she had turned it on, and she couldn't. So we reached a compromise: panties, but nothing else. Then there came an afternoon, the following Summer, when I was visiting my friend, Pete. He was working on a model car and was having trouble getting it right. At one point, one of the wheels fell off, and I dived under his worktable to retrieve it. "Hey, Don," Pete said, "what's that funny looking underwear you've got on?" I froze. My pants must have ridden down while I was squatting. I tried to evade the question. "Just my regular underwear." "But...pink? I never saw a guy wear pink underwear." I was caught. Damage control? I didn't know how. "Er...well, it's a special kind my mom makes me wear." "She makes you wear pink underwear? And it's, well, shiny, too." "Well, that's what she makes me wear." "Is it something...er, did the doctor make you wear it?" If I had thought faster, I would have said Yes. But I said, "No... it's just...what she has me wear." "Lemme see." Now what? Pete was bigger than I was; if it came to a tussle, he would surely be able to de-pants me. So I unbuckled my belt and dropped my pants, expecting the worst. "Hey, they're *panties!* Regular girls' panties!" "Look, Pete, this is something I gotta do. Don't tell everybody, okay?" "I'm not going to tell anybody. They look kinda neat." His non-judgemental tone encouraged me. "Well, they can't be the first pair you ever saw. Don't you ever see your sister's?" "Well, yes, but..." He hesitated. "What do they feel like?" "Well...nice. Really nice. It was nicer when Mom let me wear dresses and not just panties." "She let you wear dresses...?" "Yeah. From that time...you remember? We were little kids playing over at your place, and Beth made us play with her dolls. Remember?" "Nope. Don't remember that at all. Why did we do it?" "It was a rainy day and we were bored. And Beth said we could play with her, but we had to play with her dolls. You sure you don't remember?" "Nope." "Anyway, my mom came and saw us and hit the ceiling. She dragged me home and said I was a little sissy and that she was going to make me wear dresses. And she did." I hoped that would be enough. But Pete wouldn't let the subject drop. "What did they feel like?" "Well...nice. I didn't like them at first. I screamed bloody murder. But then I got used to them and decided I liked them. Why?" "Well...I'm...er, just...well, curious." He hesitated again. "Er... Don...do you have any other underwear like that? I mean...if they feel that good..." I thought I could see what he was driving at. I concealed my astonishment. "Yeah, I've got lots. Half a dozen pairs, I guess." "D'you suppose I...?" He couldn't finish the question. "...could try them on? Sure, why not?" This would be great! My worst fear was that he would blab my secret all over school; if he put on a pair of panties himself, he would never be able to do that. We left his model car half assembled on the table and went over to my place. Mom was out. We went to my room and I opened my dresser drawer. "Holy cow! That's more than just half a dozen." "So which ones do you want to wear?" "Er..." He was embarrassed, now. "...how about...those?" He pointed to a pair in pale blue. "Okay." I handed them to him. His hands were trembling as he took them. He took off his pants and his jockey shorts and stepped into the panties. I noticed something. "Pete, you're getting a woody!" He was flustered. "Well...don't you get one?" You know, I never had. There had been nothing sexy about being punished by Mom, and I had been too young then anyway. By the time I was older, the clothes had just felt good. It had never occurred to me to think of them as sexy. I explained this, as well as I could, to Pete. He looked down at the panties, smooth, shiny, and tented with his erection. "Gee...I never knew..." He paused. "Hey, look, Beth is at Summer camp. And her clothes..." I knew immediately what he had in mind. Beth was two years older than we were, and her clothes should fit us pretty well. Back to Pete's place. His mom wasn't at home, either; we were both latchkey kids. We went to his sister's room and Pete opened the closet. It was just full of lovely things. I was incredulous. "You mean you've been living in the same apartment with ALL THIS and you've never thought of trying any of it on?" "Well...not until now." We raided her dresser and closet and had a fashion show. I had to show him how to put on a bra and how to stuff it with socks to give him boobs. I had to show him how to put on nylons so they wouldn't run. I had to show him pretty much everything. Once we were both dressed, we stood in front of the mirror. Pete was unhappy. "I don't look like a girl at all." He was right. Facing us in the mirror were a pretty girl and a boy in a dress. "Pete, it isn't just what you wear. It's how you feel." I tried to explain, to teach him. I tried to remember all of Mom's lessons from years back. But it was hard to do, because by this time what she had taught me had become second nature. When I was dressed, I moved and held myself like a girl without thinking. "It's not just what you wear. It's how you stand. It's the look on your face. That's not a girly look." "But how...?" "Well, look at me." "I know. You look like a girl. How do you do it?" "I don't know. I just think of myself as a girl. When I'm Donna, I look like Donna. Act like Donna." He was perplexed. So our dressup session was a little less nice than it might have been. I was ecstatic, with all these lovely dresses to wear. I had never thought I'd be able to do this again. But Pete kept looking at me and at his reflection, and he was unhappy with the way he looked. So what happened then? Did one of us get on his knees and give the other a blow job? Nope. That never occurred to either of us. Society, if it had known what we were doing, would have called us a couple of perverts, but actually we were strangely innocent. Pete may have gotten aroused, but we never messed around, not this time and never in any of our subsequent dressup sessions. And we had lots of those, all Summer long. It was a terrific Summer. It took me back to the days before Mom had made me stop. Pete turned out to be surprisingly enthusiastic about dressing up. I wondered why, if he took to it with so much gusto, he had never thought to wear his sister's clothes before. But he sure was making up for lost time now. He observed me carefully--and he told me he was observing the girls in the neighborhood as well--and he began to look and act more feminine. We would go over to his place, select outfits to wear, get made up, and then dance around or practice girly gestures by the hour. By the end of the Summer, Pete was actually better at being a girl than I was. We had always been best buddies, but our shared secret brought us closer than ever. It was so much fun being able to do this with someone else for a change, instead of just by myself. Sometimes I'd see a girl make a particularly feminine gesture, and I would draw Pete's attention to it. "See how she brushes her hair back with her hand," or "Look at the way she runs." We had our secret jokes, too. At school that Fall, we would see a pretty girl in a pretty dress, and Pete would nudge me and say, "Wow! Howdja like to get into that?" All the other boys would laugh, thinking we meant getting into the girl, but Pete and I knew we meant getting into the dress. Maybe the girl, too, but definitely the dress. But I'm getting ahead of my story. The high point of that Summer, for both of us, was the day we got caught. We were at Pete's place. His mom was out, but we had just gotten into panties and bras when his mom came back. We heard the apartment door open; we were petrified. We heard her calling, "Peter? Peter?" and the next moment she was in the room, looking at us. I thought I was going to die right then and there. But she started laughing. Just pointing at us and laughing. Well, that was better than getting mad, which was what we both expected. She said, "Girly boys!", started laughing again, and left the room. Pete and I looked at each other. What was going to happen? Then we heard her talking, apparently on the phone. Bits and pieces of the conversation reached us: "Yes, both of them!" "Sissy boys..." "Teach them a lesson..." And then something about "fun." When she came back, Pete and I had gotten the bras off and were taking off the panties. "Oh, don't take them off!" she said. "We're going to have a little party for you girls!" We froze. Then the buzzer sounded. She went to the door, and then Mom was there in the room with us. "You see? Pretty sissy boys in panties. I think we should have them put on a show for us, don't you?" My mom said Yes. Then Pete's mom continued: "You've been very naughty boys. And for your punishment you're going to have to wear Beth's dresses all afternoon." My eyes met Mom's; she *winked* at me! Then Pete and I looked at each other. Each of us was telegraphing the same message to the other: "Don't let on!" And we didn't. We protested and pretended to be embarrassed as our moms dressed us and worked on us. It was hard for me to keep from breaking into giggles, and I guess it was for Pete, too. So what had threatened to be the worst day in our lives turned out to be the best. Pete's mom had us put the bras back on and then got garter belts and stockings for both of us. We pretended we didn't know how to wear them, and Mom showed us. Meanwhile, Pete's mom was getting things out of the closet. She bypassed the smart, conservative dresses and picked out the frilliest, most feminine outfits she could find. "Now, Petey, honey, this is for you," she said as she handed him a pinafore. Then, handing me a white dress covered with ruffles, "Here, Donnie, this would look pretty on you." It struck me that it resembled the very first dress Mommy had ever put on me. And so it went, through most of Beth's wardrobe. Finally we ended up with a pale blue dress for me and a pink one for Pete. We made a good show of crying out and complaining, but the only complaint we really had was that she had just happened, perversely, to pick out my favorite dress for Pete and Pete's favorite for me. When we were dressed, and our moms had put makeup on both of us, the teasing started. Mom participated in the teasing with a twinkle in her eye, but Mrs Klein's teasing was malicious. First, she started calling him Betsy. I never figured that out; you would have thought she would have called him something that went with Pete, like Patricia. Then she said, "Let's see you curtsey like the pretty little girls you are!" Curtseying! That was lovely. Pete and I had never thought of that. But I made a face and said, "Aww, Mrs Klein, do we have to?" "Yes, all little girls curtsey. You're little girls now, and you have to curtsey." I did my best to put a whine into my voice. "But I don't know how!" So they had to show us about putting one leg a little behind the other, bending both, and picking up our skirts. They had us curtsey to them, and then to each other, and then to them again. Mom said, "I'd like to see them dance," and Mrs Klein said, "Oh yes! Pretty girly dances!" Mom had taught me, of course, but Pete didn't know the first thing about it. So Pete's mom showed him how to stand, and how we should have our arms about each other. They had us curtsey to each other again and then, as the two of them sang, we danced. I loved that. I wanted to let go of Pete and twirl around in a dainty little pirouette, but I didn't dare let Pete's mom realize how much I knew, or how good a time I was having. The only real problem was when Pete's mom wanted us to kiss. 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And I explained how all this had gotten started: Pete catching sight of my panties and wanting to try them on. And how it had continued from then on: our Summer of dressing up. I had never before really gone over the whole history, even in my own mind, and now it struck me for the first time how unlikely a coincidence it was that there should be two crossdressing boys in the same apartment house. Mom had only one concern. With worried look, she asked me, "Did you ...like...kissing Pete?" "Naw, Mom. We don't do things like that." She relaxed and smiled. "Well, I can see I'm going to have a harder time than I thought keeping you out of skirts." And that blessed afternoon of delight marked another turning point. From then on, Mom kept a small cache of girls' clothes for me to wear. She let Pete come over about once a week, too, and share them with me. That was lucky, because once Beth was back from camp, we wouldn't have had any more dressup sessions, if it hadn't been for Mom. **** When I went away to college, that was the end of dressing for me. I lived in a dorm and had a roommate, and wearing anything but boy clothes was unthinkable. And by the time I came back home the following Summer, the clothes Mom had gotten for me were too small. Pete wasn't around, either; he had a Summer job at his college, so what with one thing and another, we eventually lost touch altogether. I never wore women's clothes again until I was out of college and living on my own. Then I joined a support group and gradually started building up a wardrobe. What a pleasure it was to come home from a hard day at the office and put on a dress to relax. I never went out en femme, except to our support group, or at Hallowe'en and then only if I had been invited to a party; my features had become too masculine for that, and I didn't think it was safe to run around town in drag. When my folks visited me, or when I visited them, Mom and I usually managed to find some time to get together for a little private girl talk, and occasionally I was able to model a new acquisition for her. So that's the end of my story, except for one funny circumstance. I was in another city on business once a few years ago, and on an impulse went to a support group there. I was struck by one particularly beautiful woman. Probably the wife of one of the crossdressers, I thought, and I envied whoever was the husband of such a stunning woman. Nothing would have come of it, except that we happened to get into a conversation later that evening, and to my astonishment this marvellous woman turned out to be a guy. Well, not really a guy. 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I was having a quiet drink on a Saturday night in a favorite bar of mine. My table was at the rear of the main part of the bar. I say the main part because there is another part where you go through a special door to get to and not too many people know of it outside the regular patrons of the bar. In that special part is a low bar where a lot of business transactions are carried out. A guy I sort of knew came in with his wife and her sister. I knew that both women lived and slept with the guy,...

Bisexual
3 years ago
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Bellboy

When Mrs Estelle B. came into the lobby a month ago I wanted to pitch her myself. Stacked, classy, blonde with the pouty full lips I love. Course I didn't have a chance. No luggage except a purse, I caught the look from the manager, she paid with a credit card to a phoney gardening shop the Royale owned, so this wasn't her first time. Meant she had a buck lined up already, which she did. An hour after I showed her the room, a huge black buck picked up the key in the lobby. Couple hours after I...

2 years ago
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Bellboy

When Mrs Estelle B. came into the lobby a month ago I wanted to pitch her myself. Stacked, classy, blonde with the pouty full lips I love. Course I didn't have a chance. No luggage except a purse, I caught the look from the manager, she paid with a credit card to a phoney gardening shop the Royale owned, so this wasn't her first time. Meant she had a buck lined up already, which she did. An hour after I showed her the room, a huge black buck picked up the key in the lobby. Couple hours after I...

2 years ago
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Tomboy

"You're the new girl, huh?" The boy was bigger than me, and probably a year or two older. "What's your name?" "Ashley," I replied, sitting on my motorcycle and drinking a Mountain Dew. We were in the old suburbs. There wasn't much else around except the school, a couple churches maybe, and a Seven-Eleven, so that's where I'd gone. It sucks moving to a new city when you're sixteen, but it could be kind of fun too, depending on what you're looking for. "You look like a guy,"...

4 years ago
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Sexy Femina Ladyboy

OMG! I wore the most ADORABLE outfit to the arcade on Friday! Picture this: After bathing and powdering, I put on my little black silk shorty robe and a pair of poofy 2 inch heeled black slippers, and did my nails in a platinum shade. Then I did my hair and makeup. Doing the hair was easy as I simply chose a platinum blond bob. Then came my eyes and lips - a frosted pink lipstick. Then I put on my black string bikini. After some sexy posing in the full-length mirror, I put on my new outfit -...

3 years ago
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Used by a gorgeous ladyboy

(Yeah it's been a while but i'v been busy … doing the thing in real life with a new guy i met and there is not much need for xhamster at the moment :) . The story below is based on a true experience and i just changed a few details to spice it up a bit)This story is based on a true experience and happened a few years ago, on a great night out in Amsterdam. It was before i had sex with guys on a regular base and i entered a complete new and exciting world...During that period of my life i was...

3 years ago
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MY MAN AND I SHARE A LADYBOY

My man Roger and I have had sexual adventures that many people would be envious of: some incredulous of even. Around once a month I love having a second man to pleasure me and before I pleasure him while my man watches, and often he will pleasure my man: oral sex only – no intercourse is the rule. In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock. “Some of your...

4 years ago
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The Tomboy

This story is dedicated to my great friend BobbyLynn.I met Bobby when I was 18 and she was 9. I had just moved to Ohio from North Carolina. I was living with my older brother in his little two bedroom house. I had just graduated high school and was planning on going to the local Tech school to take auto mechanics. I already knew quite a bit about cars and spent most of my free time working on them. My brother, Todd owned his own auto shop and was letting me work for him doing what I did best. I...

First Time
1 year ago
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Schoolgirl and schoolboy

This story is a two part. We did it my way, then her way. Enjoy The first part is about how a schoolgirl fantasy, that I wanted to do with my girlfriend. The second part is how my girlfriend did the same kind of fantasy, but she had a twist of her own to do it. It all started, when we looking up costume on what to be for her Halloween company party. She wanted to be something sexy because everyone in her office think it's kind of boring, and she wants to change that. We were looking online and...

Straight
4 years ago
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Teaching the Tomboy

Based on the short story: SARA'S PUNISHMENT By Mr. Stefens The three buxom matrons marched Sara into the punishment room, one on either arm, the third trailing behind with a scowl on her face. "Get offa me!" Sara protested stridently as the two large women marched her toward the discipline horse. How delightful it was to encounter Sara again--and so soon. "Strap her down," I ordered with a sigh. While Sara twisted and struggled and mouthed indecipherable words at her tormentors, I sat...

1 year ago
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Tommie the Tomboy

After about ten minutes or so, I really lose track of time, Tommie is gasping. "Oh, Dave... Please... Whatever you're doing... Please... Don't stop... Make me... Oh, God... I'm close... Oh... Oh... I'm gonna..." As her vagina clamps down on my finger, I sucked her clitoris into my mouth and rolled it between my lips. She's gone completely silent, her back arched up off of the grass and all of her muscles are taut. Finally, she drops her back down in the grass and screams, "GOD!" so loud that it...

Mature
2 years ago
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Moms Joy Boy

Chapter 1 Meeting over lunch to discuss Aunt Elsa’s mind-boggling suspicion that her sister – their mother – was having it off with someone, the Black siblings watched their mom walk by their restaurant window table arm-in-arm with a guy. Not only was Janis outrageously making an exhibition of herself like that in the main street but the guy looked almost their age and to their horror the guy’s hand was cupped over one of their mother’s ass cheeks and her jeans were tighter than even Gina’s. ...

2 years ago
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Naked On TV The Erotic Demise Of A Cowboy

“When a man walks or rides into a forest, he is lost among the trees, can’t see ahead, doesn’t know what might be lurking there. The forest surrounds him, obscures him with shadows, confuses itself with him by its vertical composition and competitive detail. But when a lone horseman appears on the desert plain, he dominates it instantly, his view extends as far as the eye can see, and enemies are exposed to his gaze.” (Tompkins, Jane. West of Everything. Oxford University Press.) The vision of...

Outdoor
3 years ago
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Divorcee and her toyboy

She divorced 3 years ago and has been living in a shared flat since then. Her ex-husband was amicable during the divorce and they split everything 50/50. After 20 years of marriage they had just drifted apart. They agreed to sell their house and they shared the money from the sale as well. Rather than buying a smaller place, Paula found it easier to keep the money in savings and rent using her salary. Paula had a good job in IT and could often be sent to other cities to work for short...

3 years ago
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MY LOVERS TOYBOY

“What would make it better for you? Harder, faster, slower?” She is obviously jealous, but very turned on as she watches her toyboy sucking my cock. We made an understanding some time ago that she could have a threesome situation around once a month with a third man for her sexual gratification. One of her girlfriends runs an ‘agency’ that specialises in supplying toyboys who are capable of providing sexual gratification for both females and males. We are in the fortunate situation of...

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