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I was a rather sweet boy child with a mass of blonde curls. I was about three when my mother took me to the village hair salon for a haircut. As the girl finished, I asked if I could have a ribbon in my hair and after a lot of embarrassment and tears from me, they found one. No sooner had they tied it, I realised from the fuss that was made, that as a boy I had done something dreadful. This moment lived with me and made me quite introverted. I just had one brother, five years older, and I knew nothing of girls at all, yet I was attracted to what they did and what they wore. At five years old when I went to school, I came home the first day and asked if I could have a gym slip. Mother, surprised, explained that only little girls had gym slips, boys had shirts and shorts. Why I asked? She had no answer and ignored my question. One day, not knowing what to do, I found an old dress of mothers in what she called the rag bag. It was beautiful, silky and had green and white stripes. Of course it was miles too big, but I took off my shirt and put it on. The material felt just wonderful on my skin and I proudly entered the kitchen wearing it. Mother just laughed and said "That is miles to big for you. You can play in it, then put it back." "It's got lovely material mummy. Can't I keep it?" "No, dear, you don't want a dress to play in, do you?" Again I realised that I was overstepping the mark. About a year later at school, I played alone with Elizabeth who was a bit of a tomboy. I asked her if I could try on her gingham frock. She was quite willing and we swopped outer clothes, going back to class after playtime, she in my shirt and shorts and me in the dress. We were sent at once to the headmistress who told us to change our clothes, then our mothers were sent for. At home mother told father about it when he arrived home from work. He just laughed. Then he took me onto his knee and explained that boys and girls were different and that included the clothes they wore. I was about eight years old and playing with about ten other children in the woods. We took it in turn in pairs to hide while the rest hunted for us. I was hiding with Heather, a lovely girl with auburn hair, about 18 months older than me. As we lay in the bracken, I asked if she would let me look in her panties. Very reluctantly she did so. I was fascinated and said she looked lovely. I hated my penis. While other boys enjoyed theirs, pulling at them, peeing up walls and trying to pee over the five bar gate in the fields adjacent to our country road, I hated everything to do with it. Nothing else happened with Heather. I just told her she was lovely and said I would like to be like her. Next day in the afternoon, my older brother asked if I was going on a cycle ride with him, but mother said no, I had something else to do. I asked what, but she just said we were going on a visit. She told me to have a quick but thorough bath, because she didn't want me to be seen dirty. I took it that I was going to the doctor. She ran the bath and sprinkled in her favourite bath salts. This really surprised me. I came down dressed in a shirt and shorts, grey socks and my scuffed black school shoes. My brother lent against the wall with a sardonic smirk. "Sissy," he said, "You'll grow up to be a cocksucker. I hereby disown you," he spat out of the door as if to seal his disowning me. Mother and I did not go far. We walked up the hill and instead of going on to the doctor, we turned into Heather's house. Heather's mother Vera opened the door and invited us in. We sat in the lounge and mother and Vera talked while Heather and I played with her doll's house. As Heather and I had our heads together, she whispered, "You are in for a surprise." There was a pile of clothing on the spare easy chair which I suspected was ironing. Mother and Vera talked a lot , saying things with looks rather than words and nodding towards me from time to time, mouthing words I could not hear and nodding to each other. "Right Timmy," said Vera, after a considerable time, "it is time to take your clothes off, so we can have a look at you." I started to protest, but mother said I had looked at Heather, now it was her turn to look at me. Suddenly I was ashamed, knowing that I had done something so wrong that I was in real trouble. I protested that I did not want to. Mother said sternly, "For once do as you are told. I have had enough." Tearfully I stripped down to my underpants. Vera pulled me towards her and deftly slipped her thumbs inside the elastic and pulled my last garment down. "What a funny little thing," she said, flicking my penis with her finger, "not much to be afraid of there." "Right," said mother, "we had better dress him. What do you suggest Vera?" Vera selected several items from the pile of clothing and laid them out. "I think these will do nicely for her." Vera said. "If she wants to be girly, then we should call her a girl, should we not?" Mother nodded grimly. She had selected a little chemise in a silky material with lacy shoulder straps. She handed it to mother and she slipped it over my head and guided my arms through the straps.. Next Vera handed mother matching panties, which had elastic on the legs and a pretty little bow on the front. I was told to step in and pull them up. I refused. Mother gave me a quick swipe across my buttocks with her hand. I pulled the panties up to meet the chemise. My eyes filled with tears from the pain and humiliation. Mum had never hit me before. Pink ankle socks were passed to me and I threw them back. Although inside I really loved the new clothes, pride made me put up some resistance. "Heather," Vera said, "get one of the short canes from the greenhouse to keep this girl in order." Heather scampered away and returned with the cane as I sat on the floor howling, rocking back and forth at the humiliation. "Heather, help her put the socks on." Heather knelt in front of me, rolling the sock so she could slip it onto my foot. "It's all right', she said, "it will soon be over. Just do as they say." Next came a frilly little waist slip, which I saw from the label was nylon. It was silky, smooth and soft, pink with white lace at the hem. Heather then came forward with a white blouse, with tiny lace around the small collar and at the cuffs of the short sleeves. Heather was now my dresser, deftly buttoning it up for me. To complete the outfit, I was handed a full yellow skirt, which finished just above the knee. Heather showed me how to fasten the hook and eye and zip it up. To complete this out came a pair of Heather's cast off black patent Mary Jane's. Heather knelt down and fastened the straps with the little shiny black buttons. "Mummy," Heather said, "It is just like having my own real life doll." "That is a very good observation Heather. What do you say," Vera said to my mother, "shall we give this girl to Heather to train?" "I think that a very good notion," said my mummy. I could not believe that she was giving me away so easily. "I don't want to live here," I wailed, tears running down my cheeks again. "You will still live at home, but Heather will train you. As you so want to be a girl, there are things you have to know and do. Heather will teach you." Although I had always vaguely wished for this to happen, now it had been thrust upon me it was too much. I started to undo the buttons of the blouse. The cane swished across my bottom, stopping my hands from fumbling with the tiny buttons and somehow halting my snivelling too.. "Now," said mother, "you have so often shamed me with your girliness, it is time to get it out of your system once and for all. You will behave like a girl until you decide to be a proper boy. You make a very nice girl. We just need to do something with your hair. What do you suggest," mother said to Heather. They all three primped and brushed my hair, chattering and making suggestions. At last they seemed satisfied. "Stop crying," mother said, "you have only yourself to blame. Thank Aunty Vera for giving you these lovely clothes." "Do a little twirl. Heather, what are we to call your new girl friend?" "I think I would like Timmy to become Trudy, mum." "How lovely, a good choice!" Mother and Vera said in unison, laughing at each other. "Give us a twirl Trudy." I turned around with as little grace as I could muster. "Not like that. Show her will you Heather?" Heather whirled around, her pigtails flying out and her skirt flaring. I did my best to copy her movement. " Not too bad. Heather, you will help Trudy be a better girl, teach her how to sit and how to manage her skirts when she sits on the loo. Heather, you make sure Trudy is really girly. No tomboyish games. If she wants to be a girl, then girl she will be. She can have your old bike too, the pink one with the basket on the front." "That's lovely of you Vera. And we have to do something with Trudy's bedroom. Heather you can design it for your new little sister." The one thing I loved was my bedroom. It was not very boyish, but I loved the blue walls and the pictures of our cat and dog and the blue curtains. My bedspread was a big picture of a lion's head. "That will be fun," Heather said, "It will be all pink and fluffy." "It's lovely out. Why don't you both walk down to the village and you can both buy some sweets at Mrs. Wilson's." Vera said, handing Heather a note from her handbag. And get one of your handbags for little Trudy, because no good girl goes out without one. Find her a little bracelet too, perhaps that one you bought at the bring and buy sale last week." "Mother, I can't go out like this. Please let me put my clothes on?" I pleaded. "Now stop it Trudy. You will be all right. Heather will take care of you. Do you want that cane instead of sweets, because you are not changing into your boy clothes until you have learned your lesson." I saw it was no use. Soon I was equipped with a pink shoulder bag and Heather fastened a bracelet around my wrist. Heather showed me her room. It was lovely. The curtains held back by frilly bands of the same material, her bedspread was covered in appliqu?d rabbits, and little china animals and girls in frilly frocks on her dressing table. She opened a drawer and putting a finger too her lips, signalled me to be quiet. She lightly applied a lipstick to my lips, showed me how to purse them and rub them together, then took a tissue and gently removed the excess. "Now you are really my little sister," she said kindly, and kissed me quickly on my reddened lips. "I am going to enjoy having a sister." Heather took my hand and led me to the door. I was terrified as we exited the garden gate and my eyes roved to see whether there were people about. All was quiet, at least until we neared the shops. My friends Graham and Johnny were sitting on their bikes. I cast my eyes down relying on Heather's tight grip on my hand to guide me. "Hello Heather," said Graham, "who's the shy girl?" "She's my new friend Trudy. I think you've seen her before, you just don't recognise her." I tried to escape, but Heather just increased her grip. Graham came closer, and peered into my downcast face. He laughed, "That's Tim." "Not Tim, Trudy now. She wanted to know what it was like being a girl, so she is finding out. Do a little twirl for the boys to show how nice you look, like I showed you." She swung me round, still holding my hand, her arm passing over my head as though we were dancing. My skirt flared showing my pink slip underneath. The boys cycled off, laughing, saying they couldn't wait to tell the others I had gone sissy. I was so ashamed, knowing forevermore that I would always be a sissy in their eyes When we came to the sweet shop, I peered in the window and my reflection stared back at me. It was a remarkable transformation I saw. I turned my head and swayed my body to see what I looked like sideways. I was quite impressed. Suddenly I was thrilled, realising that at last I felt as I had always wanted to. We went inside. Mrs Wilson was a large woman, always smiling and very quick witted, as she had to be to stop children pilfering from the counter top. She was also a great gossip. "Hello Heather, now who is this with you?" "This is my new friend, Trudy. She's like a sister to me." "Hello, Timmy, I mean Trudy. Trying out being a girl are you? Oh well, you look very nice in your yellow skirt. What can I get you girls?" We selected our sweets from the jars on the back shelf, and I spoke as Trudy for the first time. We walked back to Heather's and my whole gang of boy friends were all standing at the bottom of the road waiting to see the princess that had once been Timmy. Back at Heather's house we found Vera alone. "Mummy, can I paint Trudy's nails?" "I think that a very good idea of yours Heather. It will be a nice reminder to Trudy that she is now a girl." Heather took me to her room again, removed my pink socks and cut my toe nails, filing them smooth, so they would not cut my socks or make a hole in stockings, she explained. Then she painted them a deep pink. She next repeated the action on my hands. "There," she said proudly," you are now complete." "How do you feel?" she asked, kindly, looking deep into my face. "I, I.........," I stammered, "I like my appearance, but I am so ashamed." "Don't be. Look all the boys know now that you like being dressed as a girl. They will probably tease a bit, but then they always tease girls. I will look after you. You are my sister now and I will teach you everything. I'll walk you home." As we walked down the road to my house, there were a few whistles from my friends. "Take no notice, keep your head up and ignore them. They will soon leave you alone. If you cry, they will always make you cry." Later that evening, when father returned from work, mother told him what had happened and why I was dressed as Trudy. He just smiled and pulled me over to his chair. I started to cry, but he just shushed me gently, patted my bottom through the skirt and under slip, and kissed me on the forehead. "Mother knows best," he said, "and as Trudy you do look very nice." My brother sniggered from where he sat reading his book. When I went up to bed, mother made me take the clothes off carefully, folding them, or hanging them in my closet, putting the underwear in the linen basket. I felt for my PJs under the pillow, and pulled out what I found there. They were pink and silky and had ribbons threaded around the cuffs. By this time I knew that it was no good protesting. Then mother watched as I first sat on the loo to pee, and as I washed and brushed my teeth. She made me clean myself thoroughly, not as I used to as Tim, a lick and a promise, and showed me how to hold my hair as I sponged behind my ears. As I lay in the dark, I thought about tomorrow and how I would be able to be Tim again. In the morning I was surprised to find mother in my bedroom, drawing back the curtains. Laid out on the bed were more girls clothes. "Mum," I pleaded, "haven't I been punished enough?" "Oh no," she said, "this is the way forward now. At home you will be a little girl, but at school you will still have to be a boy. This is to make sure you respect women and girls and don't go looking in their knickers. You have to get over this penchant for girly things too." "But I will be good, Mummy, please?" "Stop wheedling. Now Trudy, wash yourself properly, and get dressed and brush your hair. When you are ready you can come down to breakfast. If you look nice, there may me a treat for you." I took nearly half an hour, to wash and dress, struggling with the little buttons. I brushed my hair and descended the stairs in the little pink slippers that mother had left for me. My gingham skirt and petticoat felt nice against my legs. Mother said I could have whatever I liked for breakfast, but my stomach was in knot of apprehension at what was going to happen today. As I sat, eating my cornflakes, mother took my hand and fastened a thin gold bracelet around my wrist. "Good girl, Trudy," she said. Vera and Heather appeared late in the morning. My brother was asked to tidy himself up which he sort of did, then in my Mary Jane's we all went to the bus stop. We spent the afternoon at the fair, we went on all the rides and I especially liked the chair-o-planes, swinging around at speed, my skirts flying about in the wind and showing my frilly under slip. I was constantly having to hold it down, while holding on to the chain with my other hand. I was beginning to enjoy being a girl, I felt vulnerable but protected. After that I lead a double life, Tim at school, the rest of the time as Trudy. Mother just told everyone that I had asked to be treated as a girl, and usually they just accepted that I was effeminate and mother was allowing it. Even the doctor concurred, when she explained that I had pleaded to be a girl over and over, crying myself to sleep. Soon I just accepted that I was always a girl the moment I came through the door from school and changed right away. The boys in the neighbourhood left me alone, just treating me the same as all the other girls. I played with the girls and found I was so happy in their company. The treatment that was supposed to cure my desires was in fact just what I had really wanted. It was not what my parents wanted though, as I was to find out. When I was 12, father insisted that I be sent to boarding school, to toughen me up he said, for my own good. If he is a boy, then he has to be a boy he said. This meant having all new boys" clothes, mother carefully sewing nametags into every item. It seemed to take her forever. I looked at the dull items of underwear, the grey shirts in harsh material, the awful grey suits and clumpy black shoes. The school was a horrid shock. In coarse feeling boys wear all the time, with smelly boys all the time. I missed Heather and the other girls I played with at home. No one here played the games we had played. Once more I slept in beastly striped boy PJs. Secretly I still peed sitting down and kept myself immaculately clean, but I had to shower communally and play sports, even rugger. I did my best to fit into this male society, but I really missed my female life and attire. My mother had asked the school to allow my hair to be longer than most boys, but there were others at school with long hair too. When the holidays came I was once more Trudy. It was so lovely. Everyone was so nice to me when I was pretty. All the boy clothes were stacked in a locked closet. I was taken shopping for new girl clothes as a treat and it was spotted by one assistant that I was a boy, but as usual, mother just told the story that I had grown up wanting to be a girl. And it was true I realised, I did want to be a girl. I loved my feminine life and my girl friends and the way I was treated as a girl. I wanted it all the time. I had been there a couple of years when a boy named Stuart befriended me. His family were quite well off and he wanted for nothing. One Sunday he said he was going to blow up a sluice on the little stream outside the village. We went to the sluice and Stuart produced a handful of banger fireworks all taped together. He lit the fuses and much to my astonishment, held them until all the fuses touched the powder and flared then he dropped the bundle into the water. Bubbles came up, and I grasped his arm and hid behind him. There was a sudden muffled whoosh, and a plume of water shot up from the surface, but the slice held firm. Stuart laughed because I had been frightened for him. He grasped me firmly in his arms and held me over the water, threatening to drop me in. It was an amazing experience, being held like this, the biggest thrill I had ever had. I realised that being a girl had other rewards besides lovely clothes. Stuart asked me to go home with him at half term, to the family farm. I agreed and mother let me go saying that I would not be Trudy there, but it was up to me. Stuart's father picked us up from the railway station. He picked up my little bag and said, "You sit in front darling," to me, then became rather confused. "He's not Claire," Stuart said, referring to his sister. I loved being mistaken for a girl. I explored the wardrobes in the bedroom, which were an overflow for his mother's clothes. She had once been a model and it was full of lovely dresses, furs and in the drawers, undies and corselettes. After we had gone to bed, I tried on a corselette for the first time. It fitted reasonably well,and I found stockings to fix to the suspenders and a pair of silk French panties. I sighed as I put them away and went to bed in my horrid boy PJs. Next day when I got up, I put on the corselette under my clothes. I felt a bit better as though I was Trudy again. At night, I tried on the various dresses, a bit big for me, but so gorgeous feeling and pretty. I admired the girl smiling at me from the long mirror. On the third day Stuart's father took us to the cinema. We had to take the pick up as his mother had the car to go to a meeting. As I had the corselette on I did not want to be discovered so I said I would sit in the truck but it was so cold that I had to move to the cab. Stuart's dad felt the suspenders digging into him. "What's that?" he asked, I lied that it was something in my trouser pocket, but I knew he knew................. The next day Stuart's parents went to an agricultural fair. Stuart said that we were going to stay at home to work on his car that we had driven around the yard. As soon as the grownups had gone, Stuart said he knew all about what I had been up to with his mother's clothes. "Show me how you look," he said, "don't understand the attraction myself. Let me look at you." I had to make a choice, the shame of showing my true self to Stuart or enjoying a chance to be Trudy and dressed in his mother's wonderful clothes. I pretended reluctance, but secretly could not wait. I asked Stuart to stay down stairs until I was ready. Then I set to work, pulling dresses and underwear from the wardrobes, found a pair of black heals to go with the long black ball gown I had selected. I dressed carefully. Black boned corselette, seamed stockings carefully rolled up my legs to avoid laddering them, black French knickers. I raided his mother" makeup and did my hair like the girly way I did at home. "Ready," I called, and Stuart lumbered up the stairs. He took in the sight he saw shyly. "Crikey, Moses." He gasped. Then he produced the camera from behind his back, and before I could say anything snapped me. "No Stuart," I protested. "Yeah, you may as well pose nicely as not. I have one pic of you already so why not do your best. Look at those photos of mum, see how she posed when she was on the catwalk. You look a million." For the next hour he made me pose and snapped away, making me change into other dresses from his mother's collection, even a fur jacket and a cute little hat. "That will do," he said at last. "I find you so attractive. Always have but didn't understand why. Now I know, you really are a girl under those clothes you wear as Tim. What do I call you now?" "I am Trudy at home." "You mean you are like this at home?" "Yes, for the last five or six years. As soon as I get home, I am Trudy." I explained a bit about my strange double life. "So you really want to be a girl?" "Of course." "Take off the dress. Here....." He unzipped the long back zipper, and the dress rustled to the floor. "God you are beautiful, and sexy." He undid his belt and let his trousers slip to the floor. Carelessly he kicked his way out of them and started playing with his penis which was already bulging in his boxer shorts. I was also aroused, my penis suddenly expanding in the lovely French knickers. "Take them off," he said, we don't want you marking them do we. I turned my back to him and let the silk fall to the floor, delicately stepping out of them. Before I could turn, Stuart's firm hands were on my hips, turning me and his mouth was on mine, his tongue into my mouth, sucking on my tongue, my lips alive and reacting to this invasion which I had never experienced before. I felt weak, possessed, helpless, but so alive and grateful for this turn of events. "I have got to have you," he said. "Don't you dare move." I stood, not knowing what to expect, spellbound, sexually excited as I had never been before. Stuart returned with a large pot of hand cream his mother used, sweet smelling of roses. He now had no shorts on. His penis was full blown, throbbing with the beat of his heart, the circumcised head a deep purple. Gently he pushed me down onto my knees, his penis in my face and I was suddenly revolted and petrified. The euphoria of the clothes show I had put on and his kisses had faded and here I was faced by his throbbing cock. "Suck me darling," he said gently, "it will be OK." "I don't think I want to," I murmured. "Yes you do, Trudy darling. You are so beautiful. You were made for this. Anyway, I have the photos and the one of you in the corset and knickers would look so good on the school notice board. I won't do that, but you have to do this for me. After all, you have had a lovely time this morning, now it is my time." I took his cock into my mouth, trying not to think what it was used for, and started to suck, working my lips up and down, it. He started to writhe and gasp, as though in agony, and I stopped. "No, keep at it please Trudy darling." I continued, by now I was also enjoying it, enjoying his power over me, and the endearment, of being called darling. My own penis was now throbbing as it had never done before, I thought it was going to burst. Suddenly Stuart jerked and thrust and his penis descended deep into my throat, I gagged, retracted until I could again breath and then suddenly my mouth was full of sperm. I swallowed, enjoying the taste, sucking every last drop of nectar I could. At the same time I came, for the first time in my life, my stomach shuddering with the ecstatic pain. I bit onto his penis with the shock of it. "Oh baby, you are a naughty Trudy. Look what you have done on mum's nice oak floorboards. You have to lick that up." He guided my face to the cum glistening on the floor. Gently he raised me up, his hands on my buttocks, a finger playing with my anus. "I want to bugger you now. Men and women often do that, you know. I have to have you because you are so lovely and then we will go out for lunch and I will get you a little present. He guided me to the bottom of the old fashioned bed that I slept in, bending me over the footboard. I felt him smear my anus, could smell the rose scent of the hand cream, then he opened me with a finger and thrust his penis in. The shock and pain made me gasp. Tears filled my eyes and I was suddenly afraid and ashamed. Then he was in, thrusting gently, each thrust entering me further and further, his balls slapping against my own, his hand snaked around and grasped my penis, he clenched and squeezed it so that I gasped anew. Oh, mummy, I said to myself, hurting, liking the hurt, loving his power over me. "Do me Stu, fuck me darling." I found myself saying, hardly realising it was me saying it.. He pumped and pumped, the pain was terrific but I did not want him to stop. Suddenly he released my penis and started pumping it with his hand. He came first, he filled me with his cum and then I filled his hand with mine. He retracted, and I turned to face him. He raised his handful of my cum to his face and drank it, licking the last drops. "You have such sweet cum," he said, "you lovely naughty girl." We kissed, again gently. For a young boy he knew some things. He later told me that his elder sister had given him lessons in seduction. His lips caressed mine, bringing them alive, raising another orgasm in me. Oh the ecstasy, I had never dreamed life could be so good. "Come on', he said, I will pick out something for you to wear from my sister's wardrobe. Mum's clothes are lovely but too old for you to be seen out in." He came back with a blue gingham dress and some wedge sandels. "Do your face again and your hair, I have ordered a taxi so we can go into Lincoln for lunch." I spent half an hour, showered, made my face and put the clothes on, keeping the black corset on and replacing the black stockings with some tan ones, pulling on the black French knickers. It felt so good. In Lincoln Stuart guided, holding my hand firmly, to a street where there were several restaurants. We walked past a few then turned into one. This should be OK, he said. He ushered me through the door, his hand firmly on my behind, giving it a little squeeze. I was instantly excited again. The waiters were most polite, and smiled at me, treating me with great deference. "They like the look of you," he said, perhaps I should rent you out for the afternoon." "Bastard," I said. "Now, now. That's not nice language from my lovely little whore, darling Trudy. Now I know why I was so attracted to you, why I asked you to share my study. You ought to be a girl. You are just irresistibly sexy and beautiful with your make-up and dressed. How could I have not seen that before?" After lunch we walked the High Street. Stuart kept looking in the windows of jewellers. At last he said, "Wait here, I have to get something." He went in. After a minute he opened the door and beckoned me in. "Ah, this is the young lady. Come through to our room." We followed him through to a room that looked more like a doctor's surgery. "Sit there if you would Madam!" He produced a box of ear studs and asked me to pick a pair. I picked some plain gold ones. "No, those ones," Said Stuart, picking some with little twinkling stones. I sat not really thinking until my right ear was taken and clamped. A sharp pain and this was then repeated with my left ear. I ran out of the shop, stopping to look in the mirror of the porch to see what had been done. I now had the two fake diamond studs firmly in my ears. Stuart emerged grinning. "Thought you would like them. Something to remember me by. Here, for being such a good little Trudy whore," he took a gold bangle from his pocket and placed it on my wrist. "Now," he said, "no matter what, you are my little Trudy. I am going to treat you nicely, but I will fuck you whenever I want." We got a taxi back to the farm. We opened the door to find his parents in the kitchen. "What the hell," said his father, looking me up and down, "What's going on Stuart.?" "Couldn't stop him dad. Found him all dressed up and he nearly threw a fit if I would not take him to get his ears pierced. Don't know what to do with him." "Stuart, go to your room and stay there. We need to talk to Tim or is it someone else?" "You heard your mother," his father said sternly. "Calls herself Trudy dad," said Stuart, closing the door behind him. "So Trudy or Tim, how long has this been going on? Is that why Stuart brought you here." "No. He never knew until today. I am sorry, I just love girls clothes. It's like he said, I just moaned until he took me out after he found me dressed like this." "You were wearing suspenders yesterday in the pickup. I never knew a boy behave like you have and a visitor too." said his father. "I'm sorry. I just can't help it." "Darling," said Stu's mum to his father, "why don't you go and see to Stuart. I will see to Trudy. Shut the door after you, we are going to have a long talk." When we were alone she said, " Now, little Trudy, does your mother know?" I told her about myself. "Well I can see why you got to the state you are in. Do you really want to be a girl?" "Yes, more than anything." "I must say, you make a beautiful girl. There hasn't been anything sexual between you and Stuart has there?" "No, he just gave in when I said I wanted to go to lunch as a girl, then I pleaded to have my ears pierced." "Good. Thank you for being so honest. Well, I see no reason why you cannot be Trudy for the rest of your time here. Come with me, we will see what clothes we have for you." In Eleanor's room, she looked through the wardrobe and pulled out dresses and underwear, shoes and slippers. "Try on some of these. They ought to fit. I will stay and give advice whether they suit you." One by one I tried on Eleanor's clothes and Stu's mum watched with a critical eye. Soon we had a pile of rejects and a pile which she said suited a fourteen year old. I put the gingham back on as she told me and then she asked me to kneel down in front of her. She brushed my hair, cut my hair into a fringe and then pulled the rest back, dividing it into three hanks which she plaited into one long pigtail. She tied a ribbon over the elastic band she used to secure the end. "There," she said, "wonderful. How does it feel to you?" "Lovely, thank you. Thank you for being so kind, when you might have been so horrid with the shock." "That's all right dear. There is a way to repay me. We have a friend who wants a female companion to go to a dance tonight. You will be his companion. I will get you ready, dress you, do your makeup. He likes young girls, and we owe him a lot of money, so this will pay off some of the debt. You'd like to do that for us, wouldn't you? And it will be such fun, such a fine trick on him, though we shall not tell him anything. You just have to be Trudy, be nice to him. Do you dance at all?" "I can do the waltz and sort of quickstep, not very well." "Good, that will be fine. I will ring him and tell him to pick you up at 7.00. At five we will have to start getting you ready, so let's go and choose some lovely clothes. Eleanor has nothing here other than that green gown which will fit you. Let me find some lovely underwear for you." At five sharp I was in the bath. I came out smelling beautifully. Stuart appeared as I went to the bedroom dressed in his mother's robe. "Be careful of Tom tonight. He's a right perve, don't forget you are my Trudy. Thanks for not giving me away." Suddenly I felt the more powerful. Stuart was frightened of me and what I might say. I smiled. "If you look after me, then I will look after you, Stu, but no more threats of putting my photo on the notice board." At that moment his mother appeared. "You can go downstairs Stuart, while I get Trudy ready for her big date." "Now dear, let me look at those hands. You have let you nails grow nicely I will show you how to make them a good shape." She filed away until they were all beautiful. Then she applied nail varnish, telling me not to touch anything until they were dry. While they were drying she used tongs to put curls in my hair, arranging it in a style that made me look a bit older. I sat in front of her mirror, watching as she gradually transformed me from a pretty girl into a beauty. I kept looking at the dark red of my finger and toe nails. She was so clever with the make-up. She used some false lashes, gluing them to my eyelid, carefully making sure they were just right. At first my lids fluttered, but I soon got used to them and I was soon done. I looked just fab, could not believe how much older I looked, at least eighteen, I thought. "Now dear, do you know how to look at a man? No not like that, glance sideways from under your lashes, then full into his eyes with a smile that says to him, he is the most charming person in the world. Let him think he is a king." She made me practice being a coquette until she was satisfied. She drew a corset out from behind her on the bed. The front was fastened with little clasps. Then ordering me to hold tight to the door handles, she pulled the ties at the back, bit by bit, ever tighter, until I thought I could not breathe. My waist had gone almost to nothing, well about eighteen inches, and at the same time it pushed my chest up until it appeared I had real cleavage. "Whatever you do, you do not remove the corset." She said. She explained exactly how I was to behave and what to say. The black shiny suspenders hung down my legs. Carefully she rolled up sheer shiny black stockings on my legs, and fastened them to the suspenders, leaving six inches of bare thigh. Next came a tight thong which she told me to pull up, but first she took my testicles and pushed them one at a time into a little pocket under my flesh that I had never known was there. Then she pulled my penis back so that I had a really female look. The Thong was pulled up tight. "You do not let him touch you there." I nodded, not really understanding. Then came black silk French knickers, followed by a black silk slip with beautiful lace. I glanced in the mirror and nearly wetted myself, I looked so good. Out of the wardrobe she pulled a ball gown in deep burgundy. It was so heavy, but the material was so soft and luxurious. I touched it gently, stroked the surface. "Yes," she said, "I wore that at a Paris show. It is Chanel, beautiful, simple, chic. That's why I had to lace you so tightly. I am zipping you in" She worked the zip from my backside to just below my shoulder blades. "Lovely fit." Now here are your shoes. She placed a pair of black patent high heel stilettos on my feet. "Stand up," she ordered, holding my hand to steady me. "Walk up and down." I did as I was told, a little unsteadily but gradually I mastered the heels. "Don't attempt to straighten your leg fully at the knee or you will find yourself making too long a step. Take small steps, quickly. If there are stairs, put your hand out and he will take your hand or arm and support you. With your other hand, lift your skirts just a little so your feet do not tread on it. The same coming down stairs. Have a look at yourself in the long mirror. Head up, chin up, shoulders back, bottom out." She pushed at my torso until she was satisfied with my posture. "There, perfect. Remember that attitude. Smile. Look relaxed, a little haughty. Yes, that's it, good girl. If he wants to make love to you, say it's your period and you can't. Men are very squeamish, they always accept that excuse." Now lastly, a bag. She passed me a sequined bag to match the dress. "I have filled it with everything you might need. You look divine. How do you feel?" "I feel great I can't tell you how great. Thank you so much." "Before you go, I will take a photo of you and Tom. That is most important." I descend the stairs, lifting my skirt a little as I had been taught, trying not to trip in the long skirt or catch my heel in it. Every step rustled. It was divine and I felt wet already. My date stood in front of the sitting room fire, warming his bottom. He was a small man, two inches shorter than me in the heels. He wore a dinner suit with white socks. "Tom," said Stu's mother and kissed him on the cheek, "here she is, this is our Trudy. Be nice to her and bring her back no later than 2 am. What do you think?" "Charming." He came forward and took my free hand, raising to his lips. They were soft and I felt a wetness on my hand from them. "Quite delicious." "Let me have a photo of you before you go." The bulb popped and then again and we were safely photographed. We went out to the car and he opened the door for me. I got in as I had seen the film stars do, sitting first, then keeping my legs together, swivelling in. I saw that it was either a Rolls or a Bentley. Wow. We went to a large hotel and into the banquet suite. We sat at the top table. It was all very grand and I was not a little afraid. Everyone was so nice to me and I realised what life as a pretty woman could be like. I ate very little, my corset made me feel full. I just pecked at the food, but that seemed fine. Apparently we were at some important County do and there were presentations. Tom seemed very well known. I was introduced as his niece from finishing school in Zurich, and it was left to me to make up things about my life there. After speeches we danced. Tom if a little tubby, danced well. He did not tread on my lovely shoes and kept up a constant quite amusing conversation about the other guests we danced by, who was on their second or third wife, who had made money out of what or lost all, who used to be with who. He seemed to have everyone's history. I decided he was not a very nice man. He began to sweat and his face turned red. At 11.30 he said it was time to go. I smiled sweetly. And took his arm. We left saying goodnight to people as we went. "Going already, Tom'. One chap said as we passed, don't blame you. Got a corker with you tonight." She's my little niece, from Zurich. Yes, she is a pretty girl." "Pretty doesn't do it. A real beauty. How many nieces from Zurich do you have?" We moved out of the room and into the cold night air. Tom helped me into the car. I felt drowsy from the wine. "You OK little Trudy?" "Just a bit tired." I replied lightly. "We'll stop at mine on the way. Have to get something. Better get you a coffee to sober you up or I will be in trouble." Tom's place proved to be a penthouse overlooking Boston Harbour. The garage doors moved as we approached and closed behind us. I felt strangely out of it and laid my head on Tom's shoulder as we travelled up the elevator. I felt him sniffing my hair, breathing in the scent of it. I liked that. The flat was wonderful, very modern, white furniture and carpets, large windows and panoramic views. "What a lovely place." I said. "Not as lovely as you. You were without doubt the belle of the ball, and I just had to get you home by midnight. Would you allow me to make love to you? I would be so gentle." "That's kind of you Tom, but I have my period." "Oh damn. Just my luck. They have certainly done a good job with you at that school in Zurich." How about if we do it the other way," he smirked, "you know, up the arse, or you could give me a blow job?" He was so direct, he made me laugh. "Are you serious?" I said. "Darling Trudy, never more so. Wanted to the minute I saw you. Give me a kiss." He grabbed me and pressed his mouth on mine, and then his tongue was within my mouth, a taste of brandy, a smell of masculinity. "Could I have a drink Tom?" "Of course darling, what brandy, a liqueur?" "A vodka sling please." I had never had one, but I couldn't think of anything else. Tom went into the kitchen. He returned with a goblet, filled with a slightly green liquid. There was a slice of lime on the edge of the glass, the top of which was frosted with sugar. I sipped tentatively as Tom rolled a brandy round a balloon. The drink was lovely, and I soon downed it. "Another? asked Tom. "Sure," I said, I was suddenly American. I finished the second drink too. I found myself sitting on Tom's knee, kissing him. "I am going to take your dress off, so it won't spoil," he said. I stood and the lovely gown sank to the floor like a puddle of silk. "Phew," said Tom, "what an arse on you. And that corset. Can we take that off?" "No, but you can lower my panties." "I'm going to use some KY so you will be more comfortable. I felt a slim tube enter my anus, and a cold liquid fill the cavity. Then he pushed into me with his penis. "No," I said, "first I want to suck you, please?" I could not believe I was saying this. "Alright baby. This is more like it." I turned and saw what he was holding. It was the most enormous knob and I could not wait to take it. I worked it into my mouth, slowly moving up and down, playing with his testicles, pulling at the hair on them, squeezing them so that he moaned. He came very quickly, his cum rushing into my throat and swallowed before I knew what was happening. "God," he said, "You little whore, You've done that before. Trudy you are the most." "Fuck me darling, " I found myself saying. "Give me all you have. Fuck me up the arse like the little whore I am, now in my stilettos and stockings, Fuck me like you have never fucked before." How could I say these things? I clung to his bed, legs straddled so I was the right height, feeling the intense pain as he entered me, waiting for it to subside as I knew it would once he was properly inside my arse. He gasped., then started pumping. "Slowly at first darling," I said. He slowed, then gradually sped up. I shook with the pain of his giant knob, thrilling to the pain, loving the degradation. Soon he came, I felt the sperm shoot into me. He did not withdraw, he moved it around in a circular movement within the cavity. I felt sick and weak, my own penis had escaped and exploded, shooting my sperm across his bedspread, but he seemed not to notice. At last he finished and let me go. He went to the bath room and I used Kleenex to mop up my sperm as well as I could . By the time he emerged from the bathroom I was putting my gown on. He zipped me up and kissed my shoulder, turned me, kissed me gently on the lips. "Will I see you again?" he asked. "I don't think so Tom. I go home the day after, oh today. That's tomorrow. But if I come here again, then I will ring you." I redid my lips in the mirror while he watched. I made the task as alluring as possible. In the elevator, he reached into his pocket. He pulled a bundle of notes out of his wallet. "This is not a payment, it's a present, for a wonderful night I shall never forget. Buy yourself a new gown or something, something I can enjoy seeing you wearing next time. My life will be dull until then. If you were only older and could stay with me. How old are you?" "Fifteen," I said, "well nearly. In six months." His face went white. "God almighty, what have I done? What have you done? You are under age. That makes me a paedophile. I could be ruined. He felt in his wallet again. "Here take it all, only promise not to tell anyone. Please God?" "I won't say anything Tom. I'm not that sort of girl. When I get home I will let you into a secret." We soon arrived at Stuart's As he escorted me to the door, I said, "Actually Tom, I'm not a girl at all. I'm a boy, but it's our secret. I kissed his stunned speechless lips. The door opened and Stuart's mother stood there. She took my hand drawing me inside. "Did you have a good time Tom?" she asked. "Oh well, it's late. We'll discuss things another day. Good night to you Tom. Trudy, give him a kiss good night. I kissed him. Stuart's father drove me home the next day dressed in the clothes from Eleanor's wardrobe. As I stood with mother on the doorstep, he told mother that I had been wearing his wife's clothes. "Oh yes," mother said. "He is having treatment for his addiction. It's a medical thing, would you please keep it to yourself?" Ah yes, he agreed. "But rest assured it has been our pleasure to have her and she can come back whenever she likes. We were shocked at first, but we then discovered Trudy, and I must say that my wife and I think she will make a wonderful girl. Quite remarkable." It was the end of the summer term and I was just fifteen. I could not wait to get home to my life as Trudy. The strain of being a boy was getting ever worse. I came into the house, went straight upstairs to find what mother had laid out for her Trudy. It was amazing. For the first time I had a brassiere with built in synthetic breasts, and to go with that a complete matching set of suspender belt and panties. I showered and shaved my legs for the as I always did on returning home. I also shaved off the pubic hair around my penis and the wispiness under my arms. This gave me quite a thrill. I raided mother's dressing table for nail varnish and did my toes, and used a little of her make up, eyebrow pencil and a bit of mascara and reddened my lips carefully, so it was not too obvious. I dressed in the new underwear, carefully pulling on the seamed stockings, making sure the seams were straight. They felt wonderful on my legs. I lay back and kicked my legs in the air in ecstasy. I put on the chemise and then the lovely new dress that was on a hanger. I brushed my hair but it would just not hang right. "That's OK, you have a treat tomorrow as you have done well at school. You are going to the salon at 10 and having the full works, hair, manicure and makeup." "Oh mummy, I love you," I said, and I really meant it. "We also have to talk, about the future. What are you going to do when school is finished? Do you want to be Trudy or Tim? You have to be honest. I think I know but it is up to you. If you tell me no more Trudy, then you will be Tim again. Think about it today. Why not go and see Heather, she has asked you to go round for tea. See what she says." I was suddenly so confused. I had gotten used to my double life. To be just one or the other? That was something else. I asked Heather what she thought. "I like Trudy best," she said, "Tim was just Tim, but as Trudy, you are my sister, and I love you. But what do you like best?" I thought about my life. I could leave my boy life behind, but never to be Trudy, that was impossible. At the salon, there was another surprise. They pierced my ears again because I had allowed the ones Stuart had done to heal up. Well I could hardly go to a boys school with those studs. I was asked to choose some gold studs and my ears were clamped one at a time, a sharp clack of the gun and a quick pain and I was done. I admired them in the mirror. One of the girls giggled, but she was shushed by the owner, Betty. Then I was over the sink for the shampoo, and as my hair was cut, one of the girls attended to my finger nails, filing and smoothing and paring away the skin to show the half moons. They were finished off with a pinky silver varnish. I loved looking at them. The cut was done and then they set my hair and put me under the drier. At last they were combing it out. I could not recognise Tim who had walked from the station yesterday, at all. Tastefully they did my make up, a little silver eye shadow, eyebrows plucked, cheeks faintly rouged, a little eyeliner and mascara. It was a fab morning. I walked out to get into mother's car in my new heels, clacking on the pavement, feeling a million, like a film star. It was the best morning ever. "Trudy forever, Mummy," I said. "I thought so, ever since you asked for a ribbon in that same salon when you were three. I just knew." I loved you as Tim, but love you more as Trudy. We will have to see the doctor and it is best that we see him as you are now, just absolutely ravishing. By the way, Stuart's mother has been on the phone. They are going to France and have asked you to go too. I said you would love to. Life was just too exciting. I still had the seven hundred pounds Tom had given me, so buying something lovely in France would not be a problem. To be continued.................