My Sister free porn video

My Sister By Anon Writer Let me start this tale by telling you about my sister. Why, because she is central to this story and because she is special. If she weren't so special then what happened to me wouldn't have happened. I wouldn't have fallen for their plans. I would still be male in all senses of the word. My sister is beautiful. She has long, deep, brown hair that flows to just below her shoulders. She has light, green eyes and the prettiest face imaginable. Her body is shapely in an appealingly athletic way, strong, firm yet soft and sensuous. She is slightly taller than me and just under two years older. I love her. I was fifteen, nearly sixteen when it started. I was in awe of her. She was popular, not just with the boys but with the girls also. The head cheerleader, a top student and everyone's friend. We always had a fairly good relationship, one characterised by her grace, her beauty and her witty intelligence in the face of my resolute geeky nature. I was a computer nerd. I played role-playing games with my friends and spent my spare time not outside getting exercise but hunched over a computer terminal playing games and surfing the net. We had always teased each other, or we had for the last few years, now that we were a bit older. She baited me as being a nerd, a stay-in-doors. I retorted with barbs about how butch she was, how she should have been a boy. That she didn't suit being a girl. Her response was that being a girl was better than being a boy, so much better that perhaps I should try it. Mum and Dad did not let her out at night as yet and so she was stuck at home each evening with just a few weekends spent away with her friends. She was a quick thinker and sharp witted, I wasn't so, I tended to get there, just a little bit slower - I'm not thick, but I'm not as fast as her. She had a boyfriend, of course. He was a jock, star running back of the school football team. He was a perfect match to her. Where she was beautiful and graceful, he was handsome and powerfully built. He was tall, slim and fast, not hulking slow moving and steady. Her intelligence was matched by his. They were both popular individually and as a couple. The story starts (for me) one evening when I saw her naked. She had been in the shower and was walking between the bathroom and her bedroom when I left my bedroom. She was not expecting to see me and when she did she jumped. The start dislodged the towel that she had wrapped around her and it fell to the floor in a puddle around her ankles. Her hands flashed to cover her breasts and her pubic region but they were too slow, despite her being hunched over to hide from me and the speed with which she had moved I saw everything and I mean everything. She was damn sexy. I had never thought of my sister in that way and I gaped at her in a stunned fashion. It was graceless, she was exposed and vulnerable, her body on display between her splayed fingers and there I was, crudely staring at the bits of flesh that escaped her grasp. She paused and then reached down with the hand that had been covering her breasts and picked up the towel from the floor. Holding it, she placed her hands on her hips and stood facing me. 'First time is for free, little brother, the next time you have to pay for it.' She walked clutching the towel in one hand into her bedroom and closed the door. I just stood there open mouthed. I went back to my room. I could feel the hard-on tenting out my trousers. I was struck by just how perfect she was, her legs were smooth and long, gracefully tapering from her long tanned thighs down to her sleek calves. Her belly was flat and lean, her hips boyish and not too wide. There did not appear to be a gram of extra fat on her. She had ample breasts, not big, but enough to keep my fantasies occupied for months, topped with a dark red, small nipple. Even her butt was perfect, toned, small and pert, balanced daintily on top of those long legs of hers. When she moved, believe me, she moved in a way that grabbed the eye. All I could think about was how badly I wanted to see her naked again, and not to be rushed but to have the time to study her body, to drink in the beauty of her movements. I quickly went into my bedroom, I had a problem that had to be dealt with, I had no thoughts as to why I left the room in the first place. The most important thing was to deal with that bulge in my pants. I pulled the drapes closed and closing my eyes began to remember how she had looked. Her breasts, her belly, the area of her below that firm belly, the way that she moved and how everything moved with her. I pictured her body as I saw it, stroking my erection faster and faster. There was a knock at the door. I quickly re-arranged myself, my hard-on disappearing rapidly at the interruption. 'Come in.' The door opened and my sister walked in. 'Well, get your kit off.' I gaped at her, what was she suggesting? 'You saw me, now I want to see you.' I made no move. I wasn't going to strip for her. What did she think I was, mad. 'If you ever want a repeat of earlier, you'll do it.' I stripped off my T-shirt; I could feel myself hardening at the thought of a babe like my sister seeing me naked. I didn't mind that it was my sister, it was a girl and that is what counted. I sure wanted to see her nude again and if this is what it took, well then. Peeling off my trousers next, I turned my back to her as I took off my trainers and my socks. That only left my jockeys. I pulled them down. 'Nice ass.' She commented dryly. I turned to face her with my hand over my dick, I could feel myself blushing. 'Let's see it all, little brother.' I moved my hand away to reveal my hard-on in all its glory. She chuckled. 'Some girl is going to be seriously disappointed.' I felt like I had been kicked in the gut. My mouth was dry as I replied. 'What do you mean?' 'I mean Michael, that whatever girl marries you is going to feel short-changed. You have a small dick.' My penis now hung limp, the feeling in my stomach had changed to a sense of hollowness and despair, was it really that small? I thought that it was about average, but I didn't have a lot to compare it against. She ambled contentedly over to me and reached out to touch it. 'Don't you like girls? Is that what it is? I'm not surprised, you'll be lucky if you ever get one to touch it, it's so small.' She stroked it a little and then cupped my sack. Nothing moved. 'Your balls haven't dropped have they? That is why your voice still hasn't broken. Maybe in a few years if, and I stress if, your balls can drop, you'll grow a little. But for now, you don't measure up as a man.' She turned on her heel and leaving me crushed behind her left the room. I sat on the bed, oblivious to the fact that I was naked, she had never been that cruel to me before, was I really that small. I had seen some other boys in the shower and their penises did look larger than mine, they also had hair down there, I was still waiting. It was the contemptuous way that she said it, I guess, that hurt me the most. I got dressed, not thinking, my mind was a whirl of worry. What if she tells someone, I'll be the laughing stock of the school, I could imagine the names that they would call me. I didn't know what to do. I think all men worry about their size, I was normal in that but most men don't have that kind of matter of fact confirmation of their worst fears. The next day when I got home from school she was waiting. Not a pleasant day, I had been worrying all night about what she said to me, even my mother had noticed that I looked rough that morning. I had been pre-occupied in class, not paying attention to the teachers, stressing instead about how small I was. I went to the library at lunch recess and consulted the books. Puberty for boys was around twelve. I was three years late. Three years. Then I started thinking what if I had been through puberty and this was all I was going to get. I was going to remain this small for the rest of my life. I had worried before her remarks occasionally, about my lack of hair, especially as a lot of boys now sported a full crop down there, but this brought home all my insecurities. She had proven what I knew all along. I wasn't going to be able to get a girl. Their mysteries, their bodies all would be a closed book to me, and if I did get one then she would scarper at the first sight of little Mikey in his full glory. Jesus, what a fucking life. Anyhow. She was waiting at home when I got there, this is not unusual, sometimes she finishes class early and she'll be at home first. She was in the kitchen. 'I've been thinking.' She announced as I wearily walked through the door. 'I can't show you anymore about me, you know my body and all, because you're my brother and that would be wrong.' She twirled as she said this and it made her little skirt ride up, exposing her knickers a little, she was behaving strangely. I took on board what she was saying and my face fell. I remember how she looked and I wanted to see more. Now she was telling me I wouldn't get to. All thoughts of my size problem disappeared. 'But...' She paused and looked me straight in the eye. 'If I had a sister, I could show her everything, and I mean everything there is to know about being a girl.' I looked at her puzzled by what she had just said. If I was a girl I wouldn't need her to show me, I would be the same. And more than that, she didn't have a sister - just me. She was obviously losing the plot. 'But I'm not your sister Ang, I'm your brother.' I said it slowly and not a little bit sarcastically as well. Obviously she was playing thick, her cheerleader routines had caused her brains to leak a little bit. 'But duh, what if you became my sister.' I must have looked incredulous as she continued. 'If you dressed as my sister and pretended to be my sister, I could show you all sorts of things about girls and it wouldn't be wrong, I would be showing my sister and not my brother.' I replied quickly, too shocked by what she had said to take it all in. 'I'm not dressing up as a girl for you or no-one, I'm a boy.' 'Oh well, too bad, it could have been fun. You could have learnt a lot of things that someone like you...' She wiggled her little finger at me to emphasise what was meant by 'someone like me'. 'Needs to know.' She spun around again and in a blaze of flashed knickers and whirling skirts left the kitchen. I shouted after her that she had left the milkshake behind that she was making. She hollered down that it was for me, she didn't want it. I drank it down, you don't turn down generosity like that from a sister, not in a hurry anyway. It was nice, had a powdery after taste, but it was appreciated, it was a free milkshake. As I climbed the stairs to my room I thought more about what she had said, trying to weigh it up in my mind. She could help me a lot, learning from a babe like her what girls like and how they work could help me get a girlfriend of my own. I know I'm not popular at school with the girls there, too small and underdeveloped compared with the jocks, not cool enough either. Her knowledge could give me a real head start. It could help make up for my lack of, well you know, size down there. She could really help me. By the time I reached the top of the stairs I had reversed my earlier decision, I had to find out though if the offer was still on the table. I regretted my hastiness, the opportunity to spend time with my sister, learning about girls and stuff in exchange for chucking on a few of he clothes, not a bad swap at all. Remember, I had a bad night's sleep and a rough day at school. I went to her room and knocked. I opened the door when she said come in. She was lying on the bed on her front reading some magazine, her knickers were still on display where the skirt had ridden up beneath her, it was quite a sight, like I said she really did have great legs and an ass to die for. 'I've been thinking about what you said.' I started hesitantly, she interrupted, jumping up off the bed and grabbing my hands sweeping me into the room. 'Cool, I knew you would, we'll have so much fun. There is like, so much that I can show you about being a girl.' She shoved me onto the bed and flouncing around the room, opened one of her dresser drawers. I could see the lingerie and undies spilling out of the drawer and felt a prickle of nerves run down my spine. 'Come on dopey.' She said. 'Take off your clothes and we can begin.' I started to strip off my shirt; she turned giving her attention to the drawer and its contents. 'All off.' She said, her back to me. I slowly eased down my trousers, folding each item of clothes as I removed them. I don't know why, I'm not normally that tidy, I guess was trying to hang it out. I took off my socks and that just left my boxers. She turned around and seeing I was still partially clothed, urged me to hurry up, reminding me that each night we would have about two hours before we had to stop, after all we didn't want our parents knowing what we were doing with each other. She was right about that. My dad is a tall well-built man. He was a stud in his youth and had aged well. He was distinguished looking and he could still turn girl's heads to this day. My sister and him got on very well, they spent a lot of time with each other and had lots of little 'in' jokes just between the pair of them. I didn't get on too well with him. Don't get me wrong we didn't have any big falling outs, it was just, well I guess he was a bit disappointed with me. I think he wanted a son more like him, sporty, popular with the girls, up for going to football and baseball matches. Instead I was more solitary, preferring the company of my computer. I was a good student, which I think made him a little uncomfortable around me. He was a bit of a jock at school and had the grades to prove it. Mum was a fretter, she tried her best for all of us and worried over us constantly. She could be a harridan at times and once her mind was set on something, there was no way that anyone was going to change it. As such my dad spent more time and attention on my sister and my mother on me. Well, sort of. In our house the girls did the chores whilst the men relaxed, watching the game or in my case playing on the PC. This old fashioned approach rankled with my sister, but she had learnt that it was something that she wasn't going to change. I stripped off my boxers, covering my penis so that she wouldn't see it and sat back down on the edge of the bed. I was nervous, here I was naked in my sister's bedroom and she was planning to dress me up, like I was some sort of doll. I kept reminding myself that the end justified the means, that I would get what I wanted and that I could stop this whole thing if it started to get out of hand. But the whole situation seemed a little out there. She turned to face me and looked down at my groin. 'Look at it, it's so cute.' Before I could counter that, other than to flush with embarrassment at her remarks, she threw me a pair of her panties and told me to put them on. I stood up, very hesitant now that the time had come. I slowly turned them in my hands inspecting them and making sure that I could put them on correctly, then bending over, slipped first one leg in, then the other and then began to draw them up my legs. They were small, that was my first impression. That someone had skimped with the material in making them. As I drew the rather scratchy material up my legs I felt strange, weird, scared, apprehensive and a dozen more novel feelings. The overall sensation was kind of nice in a forbidden sort of guilty way. I pulled them on and tucked myself into them. The material had a bit of give in it and the panties fit me. I could feel my penis harden slightly at the contact with the material. The panties felt a lot different from the boxers that I normally wore. The material was tented slightly at the front due to the presence of my now hardening penis. I stood there awkwardly not really knowing what to do or say. I just felt incredibly self conscious. My sister threw me a garter belt. I had seen women wearing these on the Internet and so I clipped it around my waist. She told me to make sure that I tucked the straps inside of my knickers. Next she handed me some stockings. These were a revelation. Pulling them up my legs was perhaps one of the most pleasantly unusual sensations that I had ever experienced, the way that the soft flexible material gripped my legs, gently yet firmly. As I clipped them to the straps of the garter belt, I knew that my penis was rock hard. I looked back at my sister as I finished strapping the suspenders, as I looked up she said, 'Cheese!' There was a flash as she took my picture. She took a picture of me wearing just a pair of panties, garter belt and stockings. I could not believe it. I immediately tried to grab the camera off of her and protested that this was bang out of line. I felt cheated, why did she want pictures. She held the camera out of my reach and told me to calm down. I quit jumping for the camera and began to start stripping out of her clothes, telling her that we were through with this silly idea. She sat down looking hurt and said in a small voice. 'I'm only trying to help you. You need to see what you look like and taking pictures gives you a measure of how far you have gone.' I stopped what I was doing and we talked it through. I was still very unhappy with the idea of there being pictorial evidence of this afternoons activities, but could see the sense in what she was saying. She agreed that the pictures would be destroyed once this exercise was over and that no one else would ever be allowed to see them. Slightly mollified I re-strapped my suspenders. She gave me a quick kiss and began to shuffle through her drawer again. She passed me a bra. This took some figuring out as to how to put it on. She ended up having to show me. At this stage she asked me if she could take another picture. Because she had been so helpful with the bra and because she had asked I agreed and she took a shot of me. I could see what I looked like in the mirror and felt that anyone seeing me would have to be myopic to think that I was a girl. I was conscious as I moved, of the fabric that I was wearing. It held me differently to the clothes that I normally wore and as I moved it shifted its grip, different parts tightened and loosened. I almost got lost in the sensation. My sister was watching me closely and asked. 'So what do you think of the clothes you've tried so far?' 'Not bad.' Was my curt reply, seeing the look on her face I continued. 'They feel weird.' 'Weird bad or weird good?' She interrupted trying to draw a response from me that she could work with. 'Weird good, I think.' I was trying to be as helpful as possible, it was part of a learning process for me so I felt honesty and as full as a description as possible, would help that learning on. 'They hold me differently to my clothes. They seem very fancy to put on, you know complicated. It's not like a bloke who just hauls on a pair of pants, these you have to strap on, climb into, and fasten up. It's different.' 'Is that the only difference?' Her face was a picture of curiosity, of rapt attention in my replies. 'No. When you move they hold you different. I am a lot more conscious of what I am wearing, I can feel my underwear, I don't know if that makes sense to you.' She nodded. 'Also they are far more decorative. Men's clothes are plain, they do a job, these clothes seem like they do a job but also part of that job is to be decorative, to be seen, to be on display.' She nodded again, encouraging me but I had said all that I could. 'To understand women, you need to know what it is like to be one. Part of being one is the clothes, the make up, the effort that goes into getting dressed. You're doing well. The clothes are complicated, girls wear these kinds of clothes only for special dates, not around and about, despite what men wish.' I felt encouraged by her remarks. I still felt like a fish out of water, standing in her bedroom wearing her underwear whilst she watched and helped me, but her words helped me feel better about why I was doing this. 'Of course.' She added before she turned back to her dresser. 'You having such a small dick is going to help in this regard, it'll make it easier for you to appear as a girl.' I froze, the idea of appearing as a girl shocked me I stood mortified as she rummaged through her drawer for the next part of the lesson. She turned with some lacy thing in her hand and saw me frozen faced, she quickly moved to cover up her mistake. 'You'll be dressing as a girl with me, here, having your little wiener helps you pass more easily with me. It is easy to hide it from view, a proper man would find it harder.' That made it a little better, I thought for a moment that she was suggesting that we leave the house or something, I completely overlooked her repeated reference to my penis as being small or to my not being a proper man. 'Michael. I am going to show you and spell out to you the mysteries of girls. I am going to talk to you about why and how we do what we do. Girls don't articulate such things, so some stuff you need to experience first hand.' She threw me what she had in her hand, it was a lacy slip. I stepped into it without needing to be bidden. As I pulled it up my leg, the material shimmering as it rubbed against the stockings, I almost came in my knickers. She saw the look of delight on my face and made me walk around the room, so that could experience the feeling of the slip swishing against my legs as I moved. It is a rapturous feeling. Seeing the look on my face, I strove to control it, she commented that some of the clothes not only performed a task, and looked good, but also felt nice to wear and that was one of the pleasures of being able to wear these clothes. The lesson didn't last much longer, I had to undress and give her the clothes back. She ended it by saying, 'That was a first taste of the clothes involved. We will look at all of the different types of clothes, what it feels like to wear them, how they look, how they work as the first thing that we do. 'For tomorrow I want you to think of a girls name for yourself. Think about it hard because this name is going to be with you whilst we do this learning. Here a present for you, wear them tonight in bed.' She passed me a pair of simple panties. They were a light shade of pink, were cotton with a simple elastic frill around the waist. I tucked them into my pocket and thanking her, left her room. I was happy with the way that it had gone, all right running around in her clothes was embarrassing and not very manly, but I was starting to learn about women and what they have to go through. I felt incredibly self-conscious that night as we all sat down for the evening meal. I knew that only my sister knew that I had been wearing her clothes, but I felt as if it had been branded across my forehead in large letters. I barely spoke throughout the whole meal. That night, alone in my room I wore the pink knickers that she had passed to me. I played with myself to get rid of the frustration, I wasn't yet able to produce any cum, but I enjoyed the feeling when I orgasmed. I came home from school quickly the next night, not waiting around after class to talk with any of my buddies, I wanted the learning to continue. My sister was waiting for me, her classes finish a little before mine. I drank down the milkshake that she had made for me and then I went up to her room and knocked on the door. 'Come in.' She yelled. I walked in to find her again lying across her bed, she hadn't yet changed from her school clothes. She wore a skirt that came down to just above her knees, a white shirt and a blue blazer, dark blue matching her skirt. Yep, our school believed in uniforms for the pupils. She had me strip down and we went through a selection of her clothes. Panties, to be specific. First one type then another, after I had tried each one she had me compare them, to tell her which ones I liked and which I didn't. She told me the names of each style and started walking me through why girls would wear each of the different types. My penis hardened the moment I walked into the room and it didn't soften through out. My favourites turned out to be a pair of French knickers, they're cut like boxers and the material was awesome. I could have worn those all day they felt so great. She told me that girls wore these to avoid a visible panty line. I also liked the thongs and g-strings. It seemed too weird to be wearing something so small that slid right up the crack of your butt. The sensation of my butt being touched like that felt just a bit too good. She told me that she would have hidden the penis so that it didn't spoil the line of the panties, but as mine was so small, there was not much need. I didn't know whether this was positive as I felt that tucking it between my legs would have been uncomfortable or whether to be insulted by her repeated remarks about how little of a man I was. Her comments certainly hurt. We had covered this ground yesterday, bring it back up seemed to be just insulting. We settled on the name of Michelle. I didn't like it but she insisted. It was a bit too similar to my own name for me to be happy, but she seized on it as soon as she heard I hadn't come up with one. It is a strange sensation for any boy to be called by a girl's name. To choose one to be called was just too freaky for me. The next few days fell into the same pattern. I would rush home from school, we would try on different items of her clothes and she would talk to me about them. We did items singly so the first night it was panties, the next bras, then stockings and tights (one of my favourites!), after that we moved onto skirts, dresses, pants, we covered swimwear, oddities such as shorts and boring ones such as blouses. She kept referring to me only as Michelle and as her sister. There were lots of comments like 'us girls' or 'when we girls go out.' That felt strange but I got used to it. She kept up the references to my tiny dick as well. I even started to think of it as small and when I was in the locker room, changing after class I looked secretly of course, at some of the other boys and noticed that they were bigger than me. She also praised different parts of me. When we did stockings she told me that any girl would be proud of my legs, when we did bras, she told me that the little bit of puppy fat I had around my chest looked like small breasts and encouraged me to refer to them as my tits. My ass also had praise heaped upon it for being soft and gentle, and for having a nice curvy shape. At first these comments made me feel very uncomfortable, like she was saying that I was less of a man, but I realised that she was just trying to praise me and compliment me for the efforts that I was putting into trying to understand girls. But the compliments did seem to be as frequent as the negative, spiteful comments deriding my masculinity, she referred to me as a natural a number of times, she mocked my attempts to be tough or manly. She teased me about the size and potency of my penis almost relentlessly. I enjoyed the compliments as time passed on, the negative remarks to be honest just got ignored as I heard them so often. After we had run through her clothes we started putting outfits together. It was a rainy afternoon and I had been a little later than usual, one of my friends hadn't wanted to let me go and I couldn't tell him why I wanted to go, so I got stuck with him. She had changed out of her school uniform and when I was naked indicated to me that I should wear that. I got a pair of plain yellow panties from the drawer (girls don't wear their fanciest panties unless there is a special reason, I was learning after all), I took the matching bra and put those on. Despite the comments of my sister, I didn't come close to filling out a bra, my chest was larger than I liked (speaking as a man) but too small to be of any real use in her bras. I pulled on a pair of the regulation dark blue tights and slid them up my legs. Then bending over pulled on her skirt. It was slightly long on me, falling to just the knees, whereas on my sister it came to above her knees. After doing that up, I pulled on a fresh blouse that she had laid out for me and buttoned it up. Our school does not expect anyone to wear ties, so that just left the blazer. After putting on the blazer I turned to face the full- length mirror that my sister had attached to the front of her wardrobe. I was shocked. My sister came up behind me. 'Michelle, you look gorgeous.' We hadn't got around to learning about make-up yet, and the sight in the mirror showed that. My gentle (for a boy features) still showed that I was male, but it was clear to both of us that with very little effort I could pass as a girl, and a not bad looking one at that. I was stunned. I knew that my small frame and my looks were quite feminine, after all my sister had been telling me this for well over a month now, but I didn't realise just how feminine I would look. I must have stood looking at my reflection for nearly five minutes before my sister broke me out of my spell telling me. 'Take those off now Michelle, we both have seen how girlish you look in them, have you noticed that there is not even the hint of your little thing showing through the skirt - are you still hard?' I was, but looking down you could see no evidence of that fact. My little dick was quite well hidden, not tucked away but just too small I guess, to show through the skirt that I had on. I nodded to her. She laughed. 'So cute and so small, you should have been a girl from birth, Michelle.' I stripped out of the uniform and the rest of the time was spent trying on different ensembles, casual clothes for going out in, small little skirts. I got to try on her tennis dress (that instantly became one of my favourite outfits), her cheerleader costume and many more. When it came time to finish for the day I was quite worn out. She gave me my first night dress that day. I fell in love with it. The first time I tried it on, that was it. The gentle way that it fell down my body, it felt like it shimmered down me. I know that doesn't make sense but that is how it felt. I tried it on with tights and the feeling of the soft material against the tights almost made me erupt on the spot. That night I wore it all night. We started in on make up after that, the ensembles were tried on at the same time and we combined learning on both topics. First came nail varnish, learning to apply that to my fingernails and my toes. My sister was not impressed with the state that my nails were in and she told me. 'Michelle, from now on no biting your nails, no picking at the either, look these hang nails can be trimmed away very easily and the skin at the base of the nail, that needs to be pushed down. Here look at mine.' I was careful not to let my nails get in that state again. But my defence was that as a boy or a man, you are not told how your nails should be nor to look after them, men keep their nails short and so long as there is no crap underneath them, then they are in good shape. The next day we started to look at how the face should be done up, I had to get dressed for these lessons, including building on the work of the previous day, so I had to waste time re-applying the nail varnish. Like my sister said, girls have to do this for a date, now you know what a pain in the ass it really is. She was right, it is a nuisance. Make up was something that I didn't enjoy at all. I couldn't see the point of it. That is until the end of the week. By that time we had tackled how to put on lip stick and use a lip pencil, how to put on foundation and blusher so that you would look healthy and at your best, even if you were washed out from a heavy night before. How to use eye make up to its best effect and the effect of different lighting on the end result. The end of the week, I got dressed in a rather plain and demur skirt and top ensemble, I varnished my nails so that I could wear sandals and open toed shoes, I put the make up on. My sister handed me a long, brown wig which I clumsily put on then my sister asked me to step away from the dresser and look at the cumulative effect. 'That can't be me.' I exclaimed, surprised by the sight in the mirror. 'Michelle, let me present you to yourself, you pass as a girl. There are few boys around that would be able to look as convincing as you do. You really look good, not just girlie, but beautiful with it.' She was right, I did look good. The wig wasn't right and it kind of spoiled the overall image, but a few tweaks from my sister and soon it sat in place as it should. I wouldn't go for me as a girl, my taste ran more to blondes who showed a little more flesh, I was a bit too demur for my taste, but I knew looking at myself, that no-one would question my sex. I must have stared at my image for a good ten minutes before I moved away from the mirror. I spent the rest of the session at my sisters urging, trying on different outfits to see what I felt looked the best. Again, I liked the tennis dress and the shorter skirts and dresses, I just loved the way that they felt when I moved around, the sort material caressing my thighs. I also was fond of the clothes that gripped me and held me in different ways to boy's clothes. Clothes such as tights, stockings, the different sort of panties. I wasn't over fond of bras - I didn't need them, and they were a pain in the arse to put on and take off. But corsets, basques and teddies - the lingerie I simply adored and if my sister gave me a choice of what to wear then it would be those. My little (see even I'm thinking of it as little now!) penis would cheerfully rise each time that I put on those items. That night I guess I must have not been concentrating properly, I didn't clean off all the nail varnish properly. I never noticed, my father did. We were sat around the table having just finished our evening meal. 'What's that on your hands Michael?' My father asked. I looked down and saw in two of my nails there were traces of scarlet nail varnish around the cuticle. As I realised what it was I flushed red and he grasped my hand so that he could have a closer look. I wrestled my hand out of his large paw and replied quickly. 'Oh that's paint from art class.' He looked keenly at my face as he answered. 'Art class? I didn't know you were taking art.' I was caught, I wasn't taking art, it was nail varnish, but sat there I couldn't tell my dad that it was nail varnish that I was wearing earlier when I was running around dressed up as Michelle. This is when I needed a quick answer. 'I'm not' I replied quickly. 'I just helped out in class after school.' He harrumphed, then leaving the table he turned and looking me in the eye said quite clearly 'If you want to play dress up with your sister and wear her nail varnish, that's fine, but at least clean up properly. I don't want to see it on your fingers again.' He was gone before I could protest, but my sister and mother were not. 'Angela, lend Michael some nail varnish remover would you. Michael, don't let your dad catch you wearing that stuff again, for all of our sakes.' 'Mum...' She cut off my protest with a silent look. It just said 'don't bother going there'. She left the table. Angela took my hand and walked me upstairs. I allowed myself to be lead. We cleaned the remainder of the nail varnish off my hands. I felt hideous; my family all thought I was some kind of faggot who ran around dressed like a girl. 'Ang, we're going to have to stop, mum and dad think I'm some kind of...' She interrupted me. 'They don't know anything, Dad was just teasing you, so was mum. Stop being such a little girl. Anyway you are going to enjoy our next few lessons so quit whining and come down stairs.' 'Ang, Dad knew. I saw the look in his eyes.' 'Bullshit Mickey.' That sorted me out. I felt slightly less upset, but still on edge. As we walked into the room dad stared at me. 'What are you looking at?' I asked quite hostile. 'Just checking to see if you had a visible panty line, Michael.' My face fell and I began to get upset. He saw this and quickly mumbled that he was only teasing me and reached for the paper. I spent the rest of the evening quietly watching television. That night I overheard my parents talking with my sister after I had gone bed. 'Either he is or he isn't.' That was my father. I had just popped out to go to the bathroom after my usual furtive between the sheets activity. I paused to hear what they were saying. 'He is, but don't go blowing it, I'm working hard and it's starting to have results, don't waste that effort.' What effort, what were they talking about. I paused for a moment and caught my mother saying. 'Well so long as he is heading that way, I don't see why we can't be patient, hey dear.' I left at that point I don't know what they were talking about or even if I was the person involved. The next day I felt wrong going home and getting dressed up, but it was a habit now and so I found that I had nothing else to do. Most of my friends had moved on from after school activities with me. When I was dressed and had checked myself in the mirror to ensure that I was presentable, in other words that all of my make up was correctly applied, I turned to face my sister. She had come up behind me and stood next to me. 'Today we are going to do something different. Every girl likes to be kissed and every girl needs to learn how to kiss. Today we are going to start lessons on that.' This excited me, my penis gave a slight lurch at this news, nothing like anticipation. She bent forward and checked my breath. 'Your breath stinks. Go to the bathroom and clean your teeth. There is nothing more gross than kissing someone with bad breath.' After I had cleaned my teeth and freshened my mouth, I needed to re-apply my lippy as it had become slightly smudged. When I was finally ready, my sister walked over to me and asked. 'What do you know about kissing? Have you ever kissed anyone before?' Slightly ashamed I had to admit that I hadn't, well not properly, I had pecked people. 'The first thing to remember is to be gentle. It is an expression of love, not a fight. Don't try to dominate them, gently touch their lips.' She bent forward and just lightly brushed my lips with hers. My penis lurched in the panties again. This was cool. This was what I was going through all of this for. She was hot, and she was kissing me. She had me try it a few times until she was happy with the results. 'Now try holding it a little longer. Press slightly firmer, not hard but gently. Remember you don't want to ruin your lipstick.' I tried this, and tried it and tried it until she was happy that I could sensually brush my lips against hers and gently kiss her. 'The next step Michelle, is to open your mouth slightly. Not a lot, here like this.' We kissed and in the middle she opened her mouth. 'Don't breathe through your mouth, use your nose. Try again.' On about the third or fourth attempt I was surprised when she almost imperceptibly licked my lips with the tip of her tongue. She had me in a close embrace and after the shortest pause gently entered my mouth with her tongue and ran it against the edge of my lower lip. It felt so damn horny I could have mounted her there and then. I could feel her breasts against my chest, the closeness of her body was overpoweringly arousing. We broke away from the kiss and then on the next kiss she slid her tongue into my mouth. She danced her tongue around mine, teasing my lips, tantalising my tongue, I felt like swooning. She could have done anything she wanted to me then. 'Never put your tongue into another person's mouth. Tease their lips with the tip of your tongue, but it is not your place to kiss them. Let them kiss you. Remember it is not a fight, it is passion and love so it should be soft, cunning, delicate. Don't force your face up against theirs; let them apply the pressure that they want.' We spent the afternoon practising. It was for me, heaven. This was what I was hoping for. There were a few refinements that I had to do, I had to learn to discretely check my lipstick, so I wouldn't look ruffled by the kiss. I had to raise my right leg as I enjoyed it to signal my enjoyment, bending the leg behind me at the knee. I had to learn to put my hands either around my partners neck or alternatively firmly on their buttocks. I never realised there was so much involved in kissing, I'm not complaining, it was fun learning. I have not enjoyed an afternoon more in my life. Dressed in the clothes of a girl, being kissed by a total babe, it was too much for me and when I was changing out of the clothes at the end of the afternoon, I found to my surprise that I had shot my load into the filmy, silk panties that I had chosen to wear. I could produce semen now. It was watery, and there wasn't much to it, but hey I was a man now. Still hairless however. Wow, I wanted to kiss everyone. I wanted to share this feeling with the people around me. No wonder people viewed this as being so special, it was. It was absolutely incredible. I took more care that afternoon with concealing the evidence of my afternoon's activities. My sister was slightly put out by my cumming in her panties, saying that although my penis was small enough for us not to need to hide it, it would be a good idea just to wear a pad in future so that I didn't mess up anymore of her clothing. Afternoons changed after that, we kissed each day, though it wasn't all that we did. My sister was happy that I could physically pass as a girl, but she did feel that my behaviour and mannerisms would give me away. And that to understand women better it would be a good idea for Michelle to, when dressed, behave as a girl would. I learnt how to sit, and not expose yourself to the world, How to stand, when you're in a queue, when you are talking to a man, or to another girl, when your by yourself. I learnt how to walk, in heels, out of heels, how to twist your hips to impress a particular man. She showed me how to bend over in a tight top and to steal any guy's attention with my chest. That's right a small sea change had happened. Part of what I was learning were skills that girls were employing to attract men. This was partly so that I would be realistic as a girl, as girls are often trying to attract men - even when they don't know it nor do it deliberately and partly so that I could recognise girls employing these behaviours. One of my homework requirements was that I paid attention to how girls moved and the mannerisms that they employed. To look not at their bodies, but at what they are doing with their bodies. This was hard. As a man I knew that you look at a beautiful girl walking past by looking at her face, then her breasts, then her crotch. Followed up by once she had walked past, looking at her arse, her hips and her legs. Having observed the different mannerisms, when I got home I had to learn how to reproduce them and when it was appropriate for me as a girl, to do so. My sister was great at this, like I have said, she is popular and it is easy for her to without thought, communicate well with people around her. Her looks help her popularity, but part of it is also the mannerisms that she employs when talking to the different people, to men, to her friends, around our parents to get what she wants. We started to also look at how to flirt, how to flip your hair, to look down and away after making eye contact with a guy that you fancy and then to look back at him, making direct eye contact so that he knows you are interested. How to hold your hands and gesture, how to make sweet innocent remarks that make guys sit up and beg. These lessons were making me quite cynical about my interactions with the girls in my life. Classmates would be closely watched to see if they were trying to manipulate me and my lab partner got quite a rough ride when she tried to swindle me into doing her share of a project by flirting with me and playing to my ego. Before I tell you how I next got in trouble with my parents - nearly giving the game away all together. I want to talk more about guys. My sister set me as home work a tough assignment. She handed me a pristine copy of Playgirl. 'I want you to read this magazine. It is important.' 'But it's for girls; it has pictures of men in it. I'm not gay. I don't want to look at pictures of other guy's things.' I threw down the magazine and started to walk out of the room. She picked it back up and followed me across to my room. 'Keep it for at least a week. Look at the pictures of men in it. I want to know what kind of man you are attracted to.' I started to protest, but she just continued talking to me, slowly and levelly. 'I know you are not gay, but you are dressed as a girl and part of being a girl is being attracted to men. We have already started to do work on this, about how we treat them. Now I want you to start thinking about them. We all do. We spend our time imagining what they would look like naked, fantasising about them. You need to incorporate this into yourself.' She paused, I couldn't look at her. 'Michelle, you have come a long way and have learnt a lot. Now trust me, I haven't got it wrong so far have I?' I shook my head and she continued. 'When you play with yourself, look at these pictures and imagine what it would be like for you to be with the men in them. What it would feel like if you really were a teenage girl. How would you feel? How would they make you feel? What would you want them to do with you? Soak up the experience. Don't cheat.' She was right; each thing that she had got me to do was benefiting me. I enjoyed wearing the clothes and wasn't afraid of admitting that to myself. Truth be known I wasn't looking forward to these lessons coming to an end I liked wearing them so much. The mannerisms lessons had taught me how to manipulate and how I was being manipulated. Useful stuff when you are still only fifteen. This new request of hers must have a reason behind it and I would give it a try. That night safely ensconced in my room. Dressed in a light yellow babydoll nightdress and matching panties, I opened the magazine. It is a similar format to Playboy - a publication I had sneaked a few furtive glances at in my time. Features and articles interspersed with picture sets of scantily clad and nude men. The articles were different, clearly geared towards women readers as opposed to the Playboy articles on cars, sport and the interviews. I skipped the male pictures at first, reading the articles was not too bad. Some of it even was interesting. Stealing up my courage I decided that it was time that I faced the men. I closed the magazine then opened it to the first shoot. The man was blond, in his mid to late twenties and dressed in cut off denim shorts with a white T-shirt. I didn't find him attractive. He was tall and had blue eyes. His upper arms were muscled, not heavily but enough to show that he was strong and to make him look manly. I looked at the next picture. He had his arms above his head stretching to take off his T-shirt. His stomach and chest were visible. He was lightly haired across his chest and in a small line that disappeared as it travelled from his belly button into the top of the shorts. He looked tanned, his stomach was firm and his chest broad with clearly defined pecs. I still wasn't impressed. He looked alien to me. His body was so different from mine that I could not identify with him and his blonde, blue eyed look did nothing for me. I skipped the rest of his pictures. He wasn't my kind of man, if the others were like this then Angela would be disappointed. The next pictorial showed a black man. Again I looked at the first few pictures of the shoot, and felt nothing stirring. It was the centrefold that caught me. A tall dark haired older man. He was at least mid thirties, possessing a tall fit body. I looked at the first picture of him, his eyes were staring directly at the camera and they caught me. I felt small looking at him, weak, effeminate. I suddenly found myself ashamed of the silky nightdress that was spread around me, for just a moment I could again feel the silken panties stretched across my buttocks, holding me in a way that no male briefs ever could. The feeling passed as other parts of the picture caught my eye, but just looking again at his penetrating, calm gaze I could recapture the uncomfortable sensation. He seemed to be almost mocking me, his eyes seemed to tell me that I couldn't be like him. That he was something different, something unattainable. He was wearing a suit, less the jacket, that was over a chair. His chest was broad and his rolled up shirtsleeves revealed hairy forearms. I move my gaze to the next picture. Like playboy they didn't make a lot of sense, here was this 'businessman' in his office taking off his shirt. He had a hairy chest with again a well-defined stomach visible below the short curling hairs. It was flat, not over defined but muscled. Moving to the next pose of him topless and again looking at the camera as he undid his belt, I felt like a voyeur watching this man undress. This was an unusual sensation. I felt like I was intruding upon him. The next picture showed his legs as he stood before the camera in just his boxer shorts. His legs were solid and hairy. There were no muscles clearly visible, but they looked strong. The next pose revealed his penis. I looked at this picture closely, this was my first real look at a man's dick. It was limp, but long, very long when I compared it to mine. His hung down over his sac like a coiled animal, mine jutted cheekily up when it was limp, not big enough to actually hang down. Again looking at his penis I realised why my sister was so mocking of mine. Mine just didn't compare to this. I knew that my penis had hardened from looking at this man and using my fingers I flicked between the two pages, the first picture of his dressed looking at the camera and a later one where his penis stiffened slightly, it's true hinted at length becoming more real. I brought myself off lying on my belly staring at the two full-page pictures, one second enjoying the torment that his gaze brought out in me, the other looking at the length and power of his penis. I came. A shuddering orgasm. I could understand why my sister made me read this and part of me hated her for it. I began to realise as I looked at the pictures of this man, that I was never going to be like this, that he was something that I could just not be. This realisation hurt. The next evening my sister questioned me as to whether I had read any of the magazine. She made me get it for her and the two of us looked at the pictures and she made me talk about how I felt as I looked at them. When we got to the centrefold it was clear to her how I was feeling about it. She seemed glad, then realised what I went through and the understanding that I had came to. This seemed to hit her a bit. 'Michelle, you're right, you can't be like this guy. You're not going to be this big. I mean in height. You'll only ever be a short arse and not built this well either. Does looking at him make you feel like a girl?' 'No. It just makes me realise that I am so different from him. I feel ashamed looking at him dressed like this.' She interrupted. 'Ashamed of what? That you look pretty for him? Imagine meeting him, what would you want to do.' I looked at the picture, visualised in my head meeting him, running into him at a party and turning to my sister replied. 'I would be scared, scared of what he would want to do to me. He could do anything to me and I wouldn't be able to stop him. I'm too small and too weak.' There were tears in my eyes as I said this to her. 'What do you think he would do to you?' Angela probed gently. 'I don't know, probably hit me and beat me up for being some kind of sissy, I guess.' 'Michelle, look in the mirror. You are a sissy, but there are benefits in that. He would never know that you were a boy until he got stripped you down to your pretty little panties. By that point, he probably wouldn't care he would be so hot for you.' Her words were spoken softly and soothingly, they calmed me down, but when I looked at the pictures I still saw his eyes telling me I never would be like him, that I was weak, inferior and I saw the coiled potency of his resting penis. His gaze still made me feel, I don't know it's hard to put into words, inadequate is about the best I can do. We lay on the bed still for a few minutes before Angela asked. 'What do you think it would feel like, kissing him?' I looked again at the pictures of this man with his strong jaw line, cleft chin and unable to meet her gaze replied. 'I think he would have to kiss me, that I couldn't look him in the eyes because I am just a little sissy and would be afraid. I think that his mouth would taste of cigarettes and that he would not be gentle but would grab me and hold me so tight that I couldn't escape.' I paused and looked at the pictures again. 'I think that his face would feel rough against mine, that he would thrust his tongue into my mouth, that it wouldn't be gentle like kissing you, but harder and faster.' I stopped there. I could almost feel the man kissing me and I felt silly for that. 'You did well, Michelle.' My sister said, rhyming my name. 'I didn't expect you to go this far this quickly. I have another magazine for you as well.' She clambered off of the bed, her skirt that had been around her waist fell to mid thigh as she moved to her closet. The magazine that she handed to me again was new and I did feel some curiosity as to when she could have bought it, but my thoughts were dismissed when she opened up a few of the pages. The men were hard in this one, their cut penises winking at me. There gaze firm, hard and level as their eyes stared out at mine. 'Play with this tonight, but look some more at our friend and think about how it would feel for a real girl to be with a man like that, what would they do? How would it feel, and then think about what a sissy like you could do with a man like that.' I took the magazines from her with a heavy heart. They proved to be interesting when I got round to reading them. Again I was wearing the babydoll nightie this time with the matching thong panties. I enjoyed the way that the thong felt between the cheeks of my butt, sensual and strange - not a feeling I had ever had when wearing my jockey shorts. I opened the Playgirl at the picture of the man with his clothes on. His gaze seemed after this afternoon, slightly friendlier. He was looking at me as if to say, you're never going to be what I am sissy, but that doesn't mean you're a bad person. His calm gaze looked up from the page at me almost challenging me to meet him and to try him, to see what he would make of me. I left the magazine open at the first page of his photoshoot. I opened the other mag, this one didn't have the articles that the other had, it was packed cover to cover with picture spreads. The pictures were the same quality, but the models were not. What they did have, that the Playgirl did not was erections. These fascinated me from the first page. Some of the men were alone, others were in pairs. There wasn't any overt gay sex, but the message ran through that boys were boys and some boys liked other boys. The models, like I have said, were not the same quality as the ones in Playgirl, but there were a couple that I had to have a second look at. I seemed to have a preference for dark haired men, blondes and red heads did nothing for me. I found them unappealing and rather sinister. It was the dark haired men with their hairy chests and legs that fascinated me. I guess because I have so little hair, that it is the men covered in hair that spark my curiosity. I found a picture of a solo man that drew my attention. Again I was lying on my stomach and rubbing myself against the bed as I looked closely at his series of pictures. He was tall and broad, immensely more powerful physically than I could ever be, similar to the Playgirl model that I found myself drawn to. His penis again hung ominously over his sac when limp, but when erect it jutted arrogantly and confidently from his groin. His sac was full and heavy, swinging below his hard on. I kept being drawn back to the sight of his penis and following my sister's advice I began to try to imagine what it would be like to be with him. He looked slightly more approachable than the man from Playgirl. I stared at his pictures and imagined him talking to me. I was a sissy and he would know that from the outset, but he would be drawn to me. Perhaps he would find my soft skin and girlish dress arousing, perhaps it would be curiosity about how I came to be like this that would attract him. He would be the initiator, He would kiss me and I would open my mouth under the pressure from him. He would be quick at exploring my body with his hands, he would gently stroke me with his hard hands, hands that could hurt or break me, he would treat my softness in the same way that he would gently hold a baby. He would rein in his power to stop himself from hurting someone as delicate as me, but I would know as he held me, the power of the man. He would touch me, we had tried that my sister and I. She had me lie on the bed in my panties and bra and she had caressed different parts of me to find out what I liked. He would know, he would run his hands firmly up the outside of my legs and the top of my thighs. He would touch my stomach and run his hands, his broad, powerful hands down into my panties to discover what secrets lay in them. This is what he would do to me. I came looking at the different men, looking at the proud hard penises that leapt from the page at my face. I came looking into the eyes of tall, broad, dark men who would know how to treat the little thing that they found when they would play with me. I came in a shuddering climax, probably my best yet. My sister was right, imagining what these men would do to a little sissy like me was far more erotic and arousing for me that just looking at the pictures. I wondered to myself how it could get better. The voyage of discovery so far had shocked me with the pleasure that it contained for me, the sensations of girlie clothes, the idea of pleasing men, so new, yet so powerfully exciting. But back to the story, I was going to mention about my parents and my fuck up. I called my dad 'daddy'. This may seem small and insignificant, but it was a no-no to my family. Boys refer to their fathers as 'dad' girls refer to their fathers as 'daddy'. The three of us were watching television one evening, my sister was out with a friend. My dad had been giving me funny looks all evening and I was not feeling especially comfortable. He finally turned to me and said. 'Michael, you sit like a girl.' I looked at how I was sitting and flushed as I realised that he was right, my legs were together and crossed at the ankles and my hands folded in my lap. I sat square in the chair, the way that my sister had taught me to sit. I immediately moved my pose to that of a boy, I spread my legs and moved my hands. 'What do you mean I sit like a girl?' I questioned, my voice hostile. He mimicked the position that I was sat in and mocked me. 'My name is Michael and I am a little sissy, I sit like a girl...' 'Daddy!' I protested. As soon as the word was out of my mouth I realised the magnitude of my mistake. He sat there looking at me and shaking his head slowly. A smile, not a friendly one spread across his face as he contemplated the ammunition that I had just provided him. 'Daddy...' He mimicked. 'Daddy, you're being nasty to me and I don't like it.' He mocked me speaking as I had spoken, with a higher pitch than normal. 'Michael, perhaps it would have been easier for you if you were born a girl. You just don't make the grade as a boy.' I couldn't argue back, tears began to prick in the corners of my eyes, I looked to my mum for support and she made it clear that she was staying out of this one. 'Dad...' I started before he interrupted 'No. Call me daddy from now on. And if you are going to cry, go to your room young lady.' I was stung. Tears were forming rapidly in my eye from the harshness with which he had spoken and the shame of having to now call him daddy, as if I was a little girl. I went upstairs and cried with shame in the solitude of my room. That day my dad changed towards me. He stopped treating me like a boy and began to treat me more and more like a girl. When he spoke to me he often, in front of the others, called me a little girl or mocked me by referring to me as she. I had to start helping my mum with the cooking and the housework, jobs that before I had been exempt from as they were woman's work. All of this humiliation, that is what it was, humiliation. He was humiliating me and I resented him for that. But I didn't challenge him. I never argued I just sat there and meekly took the abuse. My parents were due to be away that weekend, I was looking forward to that a lot. They didn't often go away and there was no need for a babysitter, my sister told me that she had something special planned for that weekend, but wouldn't tell me nor even give me any hints as to what it could be. She sympathised with me over my dad's treatment, but like my mum she soon started doing it as well. It was about a week after my dad started to refer to me as a girl, that he issued the edict to the other two that they also had to do the same, neither of them protested, well not much anyway. They had at first stayed out of the bust up between the two of us, treating this as one of my dad's little funny fits and aside from token protests, had not gotten involved. Then like I said, he told them to start it. They were more relentless. My sister already referred to me as Michelle and treated me as a girl when we were alone, but now she did it in front of my parents. It was due to a slip of hers that all three of them stopped calling me Michael and started calling me Michelle. My mum was tough. If I used 'unladylike' language or sat wrong she would correct me, making me sit properly as a girl would. My afternoons were heaven, my evenings an embarrassing hell. The studying of boys intensified in the week before that fateful weekend. My sister wanted me to start observing boys in the street and at school and to start trying to imagine what it would be like to be with one of them. That I found difficult. I could imagine meeting with one of the men in the magazine, and as the days went by my fantasies regarding what would happen with them intensified in terms of content. They stopped just kissing me and started to do other things. This brings me to hardest part of this story, the day that my dad took me. You readers may have seen it coming, God knows as I read back over this account I can see how it was building, but at the time I was so caught up in this web of misery I could not think ahead to the next step for my journey into femininity. It was a weekend, a slightly ordinary one, where my parents were going to visit my aunt, staying with her over night. My parents left around nine o'clock on Saturday morning, with strict instructions to 'you girls' about what we could do and what we could not. My da