Sissy Boy Chapter 1 free porn video

I'm often asked where I get my ideas from. You might observe that my sister appears in some of my stories and it is she that created my submissiveness and the cross dressing 'illness' within me. Most of my stories come about from experiences, 'adventures' that occurred through my life by the foolish cross dressing need she instilled within me. Many of my stories are therefore based on those happenings. There is a cross over between fantasy and reality of course, whilst the framework is often based on reality the detail is subject to fantasy. I'm telling you this because I want to explain that in this story no under-age perversion is meant, insinuated or condoned in any way. In addition, sexual abuse is hateful and not to be tolerated. In this story the things that happen, happen with agreement, albeit seemingly reluctant and they cause some enjoyment to the characters. Here I am simply telling a story of a time that I went on a cycle ride with the intention of dressing up and being silly and unfortunately got caught by the gentleman who owned the estate that I was playing on. The young man (me in first person or you the reader) may seem to be a young schoolboy, but he is a schoolboy over the age of consent as was I when I was in upper school when this happened. I am also very aware that I haven't explained the perverse persuasion of Mr Layton Phillips, but I will expand on that at a later date. So this is the first part of this story named Sissy Boy, it has been part written and in and out of my mind for some time, I hope you like it and that in itself will persuade me to develop the story further for you. Before I stop my babbling and let you get on with this story, I thought I should refer to some of the other stories which you have requested that I continue. I apologise for my slowness with subsequent chapters, often I have to have time to think and often I am just not in the right frame of mind to continue with the storyline at that time. In Submission is one example, but there, isn't it nice to be teased and to use your own imaginations for a while, about what terrible things might befall our hero! So without further ado, here is Sissy Boy. Mum and my sister were working as usual, but it was an inset day at school so I had the day off. I'd been looking forward to this day for a few weeks, I had decided to cycle up to the woods in the old estate by the river. I'd discovered the spot one day when I was wandering about on my bike, it seemed an ideal hidden place to go to, there certainly was no sign of anyone having been there and it was so quiet and private it seemed ideal for a little secret adventure. Today I wanted to, perhaps, if I had the guts, go and dress up and play in the woods there. I was trembling in a mixture of excitement and nervousness as I carefully selected my dressing up clothes from my hidden stash in my bedroom, gently taking out each item, folding them and putting them into my rucksack. I had to stop myself from being silly and just putting lots of things in so I restricted myself to one of everything. When I finished, I stuffed my coat on top to hide them and pulled the string tight, tying it safely before setting off on my bike. This part of the old estate was close to the river and was my planned secret playing place that I was convinced no one knew about. I turned left off the main road, down a lane and after about half a mile, when the woods were starting on my right I came to the path. It was very narrow and I had to push my bike to go along it. The path meandered along with high hedges either side of it, it was slow going and I was feeling quite hot by the time I came to the little narrow gap in the hedge. Unless you knew about it, or had explored it as I had, you would never know that it was there. I wriggled the bike through first and then followed until I was finally on the moss clad floor of the woods, lit by the dappled sunlight that filtered through the trees. It was easy going now, pushing my bike along, the wheels making crunching noises as they rolled over the dried leaves and twigs, breaking the stony silence of the woodland. I finally stopped where the woods dropped away over a bank to the shore beside the river, this was the favoured hiding place that I'd found. I plonked my bike down on its side and walked down to the shore sitting on the soft mossy ground there, clutching my bag, my heart pumping in my mixture of nervous excitement at the thought of dressing up here, in this outside place, far away from the safety and secret privacy of my bedroom. My nerves held me back though and instead, I explored a little, listening and watching for signs of anyone nearby. For some reason I kept deferring my fun an uneasy fear flirting inside me until I Finally, in a thrill of excited naughtiness, overcame my nervousness. With a pounding heart I suddenly couldn't stop myself and with trembling hands I undid the string holding the top of my rucksack closed and began to open it. The voice almost gave me heart failure, it was right behind me, male, authoritative and very loud. "What are you doing here? This is private property you're trespassing; this is my land. What are you up to eh? You're planning to steal something or break into my house, aren't you? Thief!" I jumped up, clutching my rucksack to me, near tears at the shock of seeing him and his aggressive accusations. I tried to stutter my denials and to tell him that I was only playing on the river bank. He was a tall, upright and mature man, clean shaven and well dressed and he spoke with a precise English accent. "I don't believe you, I think you're here to steal something. What's in the bag? Is it something to help you break in to my home?" I was sobbing. "N, n, nooo sir, no it's only my coat," I babbled panicking now. "Show me," he barked. I opened the top of my rucksack and pulled my coat out a little, showing him as I did so. "What else is in there? What are you hiding?" His aggression was increasing if anything, he seemed furious. "Nnnothing ssir, nothing," I was almost begging him to listen to me, to believe me. "Give it to me, let me see, I'll soon find out what you're up to you little thief." I had no alternative, there was nowhere to run and though he was old, he seemed to be a fit lithe man and I was sure I'd be in trouble if I tried. Reluctantly and in fear of an awful impending embarrassment, I nervously passed my rucksack up the bank to him. He pulled out my coat, dropping it to the floor, then began to take out my dressing up clothes, one by one, laying each out in turn, more and more carefully, slowly studying each item in turn, before placing them gently on top of my coat. I couldn't look at him, my eyes were to the ground, my face blushing scarlet, struggling to think of some excuse but burning in the sheer embarrassment of the knowledge that I'd been caught out. I was too ashamed I didn't look up, I didn't see the gleam in his eye, didn't see the gleeful look that spelt my downfall. There was a long pause, silence as I stood there trembling, waiting for the humiliating words, until. "Ha, so... You thought you'd disguise yourself and dress up as a boy, that's it, isn't it girl? You planned that I wouldn't be able to recognise you or trace you as the boy who robbed me, eh? However, I have found you out, haven't I girl?" I gaped at him, confused as I glanced up. "Well, let me tell you for nothing, for a start I don't like girls dressed up as boys, for another, I've caught you out haven't I girl? Seen through your little trick." I looked at him, my confusion growing even more, what was he on about? Yet deep down I felt a strange fluttering in my tummy. "Well I won't have it girl, I won't have any of it. Now strip, get those boy's clothes off immediately and get your proper clothes back on." He took a mobile phone out of his pocket and waved it at me. "Before I call the police. Now get a move on girl and strip, get into your proper clothes and quick about it." His last sentence was shouted in such aggression that I began to cry. "Quit the tears girl, they won't help you, now get out of those boy's things and quick about it, or else." I sobbed in abject humiliation as I undressed to my pants. "Come along, everything, your panties are here in this pile, you're not fooling me anymore girl." Whimpering in embarrassment I slipped my pants down too, my bare genitals totally obvious to his eagle eyes, showing my youthful boyhood to him, yet it didn't seem to make any difference. "Give them here girl." His hand was outstretched for my clothes and terrified I handed them to him. "Now get dressed in your proper clothes girl, quick about it, all of them, or I will phone the police." I'd stupidly chosen the clothes because I thought they looked sexy and turned me on when I wore them in the secrecy of my bedroom, but this was a whole different humiliating and terrifying thing having to put them on in front of this forceful and threatening stranger. The panties were white satin and were clingy, cool and silky to wear, I was trembling when I picked them up, my face burning in shame as I stepped into them and pulled them up my legs a terrible humiliation surging through me as I pulled them up over my bum, trapping and hiding my small penis as I did so. The camisole matched the panties, I'd idiotically chosen it because it always made my body quiver when I wore it. Putting it on now created a quaveringly submissive feeling in the pit of my stomach. The Tee shirt was pink with a picture of Barbie on the front, the neck a scoop which just showed the lace edge of my camisole beneath it. I knew this was childish and little girly, but it was part of the stupid game I'd planned playing on my own here in the woods. Now in this state of awful shamefulness that childish baby girl look, only furthered my tearful feelings. The skirt was a red tartan miniskirt, it came to upper mid-thigh, with buttons all the way down the front. With the tee shirt it only enhanced the little girl look, but worn by an older girl, would have easily been mistaken as a slutty sexy come on. Putting it on now made me feel even more embarrassed and in reality, very vulnerable. I'd included a pair of white ankle socks with pink piping around the edge as I thought it went with my idiotic little girl look, never intending it ever to be seen by anyone, it was just planned to be a part of my own silly fun. I pulled them up over my feet, the frilled tops just covering my ankles. I didn't look at him, I couldn't, I was too ashamed, but He was watching me closely as I dressed, taking in my every quivering move. "Where are your shoes girl?" He was rummaging in my rucksack I glanced up at him, terrified, then pointed at my discarded trainers. "Hmm, I suppose they'll have to do for now girl, but I don't like girls wearing those things." He paused. "You'd better put them on then." He was still feeling about in my rucksack when I put my trainers on, then to my horror he pulled out my mobile phone, the smile on his face was unmistakable and sent a cold shiver through me. Moving quickly, he stuffed my clothes in to my rucksack, then picking it up, he grabbed me by the wrist and pulled me after him. I stumbled along through the woods until we got to a proper path which he hurried me along. I'd never seen the house before, never even knew it was there, but now it looked like a mansion, huge, grey and imposing, the very sight of it terrified me. In moments he'd unlocked the front door, tugging me along, his grip like steel, unrelenting as he steered me into what I soon realised was his study. He released me then, turning to lock the door behind us, before he went over to sit behind his desk. "Stand still there, girl." His voice was loud, authoritative. I stood there watching him, in nervous silence, my face bright red. He pressed various buttons on his computer which was to his left. There was a funny ball shaped object beside the screen and he moved it about, turning it to face me as he did things on the computer. "Right, now I'm recording this as evidence, I'm not having you lying, this video will be proof, understand?" I felt the blood drain from my cheeks at his words. "I I'm not lying sir. I I didn't mean to trespass sir I was only playing," I stuttered feeling horribly afraid that he would call the police and that I would be in terrible trouble. He had my phone in his hand and I suddenly heard the tell-tale click of the camera going off, but he remained silent tapping away and studying my phone whilst making notes on his notepad. It all fuelled my already shattered nerves. "I, I didn't mean to trespass sir, I, I only wanted to play by the river bank sir," I was pleading, begging now, but he seemed to be ignoring me. Then finally he spoke again. "What's your name girl?" He sounded like my headmaster at school, a voice that instilled fear. "Richie..." I began quietly. "No, no it isn't, you're lying to me again girl, Richie is a boy's name, the boy you dressed up as to fool me, now stop lying and tell me your real name girl." His voice raised in anger. "M, my n name is Richie sir," I began again. "You're a little liar, you little bitch," he spat, "if you don't tell me the truth now, I'll call the police and we'll see what they have to say." He reached for his phone, my head was going around and round. Girl! He kept calling me girl, what girls name? What girls name? What could I tell him? What did I need to do to stop him? After what seemed like an age and as he began to dial, it came to me, I'd tell him the stupid girl name I pretended to call myself when I played dressing up in the privacy of my bedroom, that would have to do. "Rachel sir," I gasped the name out. He stopped dialling and looked at me, then put the phone back down. "What did you say girl?" My cheeks were burning again. "M, my n, name is Rachel sir," I stuttered, feeling peculiar as I said it. "Hmm, that's better girl, it's best to always tell the truth, now tell me your name again, properly without stuttering." I looked down at the floor, not wanting to have to say it again, he gesticulated with his hand to hurry me up. "My name is Rachel sir." It was barely more than a whisper. "Louder girl," He pressed me once more. I swallowed then spoke again, trying to quell the tremble in my voice. "My name is Rachel sir," The words made me feel odd, a funny tightening in my tummy as I said them. "That's better girl. Now where do you live?" He had my phone in his hand and my address was on it, so he knew I couldn't lie. I quietly told him. "105 Hadfield road sir." "He nodded, that's the road out of town towards the river isn't it?" I nodded nervously. "Whereabouts on that road Rachel?" The name made me feel strange, but I was too afraid not to answer him. "On the left as you leave town, just before the builders yard sir," My voice was quiet. "What's your mother's name Rachel?" The questions went on and on. "Amanda sir," I whispered. "Where does she work?" "In the supermarket sir." "Father?" "I, I haven't one sir." "Brother? Sister?" "H, half sister sir." "Her name?" "Diana sir." "Hmm, her father?" "I, I don't know sir." "I've got their telephone numbers from your phone so I can check later. Now, Rachel, what were you up to sneaking onto my land and disguising yourself? What were you hoping to steel?" I almost wept as I begged him to believe me. "I didn't mean to trespass sir, really I didn't, I was just playing, I wanted to play on the river bank sir, honest sir," I repeated and repeated it, I was sobbing by the time I finished. "Hmm, alright, but why were you dressed up in boy's clothes then Rachel, disguising yourself eh?" I was taken aback, how could I reply to that, without lying, was he stupid or blind, he knew I was a boy yet he kept on calling me a girl. So I just said the first thing that came into my head. "I, I was just playing sir," I sniffled. "You know you've been a very naughty girl don't you Rachel?" I half nodded, I had to admit, I'd knowingly trespassed and it was wrong. "Then tell me Rachel." "I've been naughty sir," I mumbled. "No, tell me you've been a very naughty girl, now tell me properly, admit it and look into the camera as you say it." I blushed deeply again, then reluctantly, half looking at the little camera I took a deep breath. "I've been a very naughty girl sir," I mumbled once more. "Yes, you have Rachel, you've trespassed on my estate, caused goodness knows what damage to the river bank and dressed up as a boy when you were doing it. I don't totally believe your reasons, but time will tell. You can see why I am annoyed can't you Rachel." I nodded. "Ys sir," I whispered hoping that this was the end of it "So, Rachel what do little girls like you deserve for being so naughty?" I struggled to think, what did he want me to say. "Umm, apologise sir?" I said hopefully. "I don't think that's good enough, do you Rachel?" I looked at him thinking, perhaps he was right, it wasn't good enough, I shook my head. "N, no sir." "No Rachel, so what should happen to a naughty little girl for being so bad?" "M make her pay for the damage sir," I mumbled. "Perhaps that will come later, but no Rachel what do we have to do now, to teach a naughty little girl a lesson?" I was quivering, my mind racing, I couldn't think, I could hardly look at him. "Umm, umm, s s smack her sir." My voice was not much more than a whisper. He looked at me in silence, the pause noticeable. "What do you mean, smack her Rachel? Smack her where?" I was struggling to think, I was stupid to have said that and now I was terrified trying to avoid the obvious, but deep down I knew where mum used to smack me if I was naughty. The silence dragged on and he just sat there looking at me expectantly, until I finally said it. "On, umm, on her umm, on her bum sir." My voice was just a whisper now. I missed the little smile, the gleam in his eye, I was looking at the floor unable to look at him. "On her bum Rachel? Do you mean she should be spanked Rachel?" His voice was low, measured. "Is that what you mean Rachel?" I was still for a moment, feeling extremely uncomfortable in the silence before finally giving a little nod. "Then tell me girl, tell me what you mean." I felt terribly nervous, my legs were trembling "She umm, she, she should be spanked sir," I finally mumbled. "You've been a naughty little girl Rachel, haven't you? Do you think I should spank you?" His voice was low, measured. For some foolish reason I nodded, probably in reaction to his words or was it because I couldn't think what else to do. "So, you think I should spank you, do you, you naughty little girl?" I was wringing my hands, one foot scraping over the top of the other, I didn't realise how much I must have looked like a naughty girl. "Do you?" He barked, making me jump. "Ys sr," My reply was again a pure reaction to his voice. "Then say it girl." His voice was loud and authoritative "I, I, umm, I, think you should spank me sir," I whimpered. "I want to hear it from you Rachel, tell me, I've been a naughty little girl and I think you should spank me sir." A tear ran down my cheek. "I, I've been a naughty little girl and I think you should s, spank me s, sir." "Yes Rachel, you have been a very naughty little girl, now show me what a good girl you can be and ask me nicely to spank you." "It was sheer hell I was going through, the complete embarrassment of the whole situation, yet my tummy felt in knots and a submissive tingling was bubbling up inside me. He was staring at me now, silent, waiting. "P, p, please sir, will you spank me for being a naughty girl." The quivering buzz through parts of my body was confusing me. "Yes I will, Rachel." He got up from his seat and walked across the room to a big, heavy looking, oversized upright dining chair which he carried over with ease, placing it beside me, then he adjusted its position, looking across at his desk as he did so. I was fully expecting him to tell me to bend over it, but when he seemed as if he was satisfied with its location he sat on it instead, while I looked on nervously. "Ok Rachel, you naughty little girl, over my knees with you." His voice was firm and assertive. I paused, looking at him nervously. "Come along, quick about it girl." He raised his tone. In nervous trepidation, trembling in a mixture of fear and humiliation, I bent over against his knees. "Come along right across them girl." He grabbed my arms and pulled me forward over his knees, for a moment I thought I was going to fall, but his grip was firm and in seconds he had me fully lying over his knees. I found that my feet were off the ground my head and shoulders dangling to the floor, my hands on the floor because I still thought I would fall. His left arm was across my back, around my body, holding me tightly to him, his right hand resting on my bottom. "You've been a very naughty girl haven't you Rachel?" "Ys Sr," I whimpered, just wanting it all to be over. "First you trespassed on my land, causing damage. I think that you deserve to be punished for doing that and I'm now going to spank you as you asked me," Then to my horror I felt him pulling up my skirt, tugging it up over my hips, over my bum, until it was rucked around my waist. He placed his hand on my panty clad bottom. I quivered, a tremble going through me as I wriggled there, the heat of his hand almost teasing my bottom and I suddenly felt terribly submissive and girlish. The first smack took me by surprise and I jumped squeaking, but he held me tightly. The spanking was a weird slow painful yet confusing process. He paused after each smack, resting his hand on my bottom for a few seconds before smacking me again. My bottom getting hotter and hotter, each stinging smack seeming to hurt more, I struggled and squirmed each time, but by the time he got to eight, nine and ten I was still and sobbing, weakly broken and under his control. "You will be spanked each time you are naughty, girl, you must learn to behave, mustn't you?" I just whimpered a barely heard, "Ys Sr," through my sobs. "Yes, now you were also very naughty dressing up as a boy and trying to fool me by your disguise, didn't you girl?" I just whimpered. "You have to be spanked to teach you girl." His right hand was still resting on my poor overheated panty clad bum as I lay there sobbing and quivering. I was hardly aware that his left hand had slipped up beneath me, finding my shrivelled little penis through the thin nylon of my panties. Slowly he began to touch and tease me there, his fingers delicately finding and stroking. I gasped, wriggling, his fingers beginning to create feelings that I didn't understand and were turning me to jelly. "You have to be spanked to teach you haven't you, you naughty little girl?" His voice was softer now, like the teasing. "Haven't you, you naughty little girl?" I couldn't stop myself the feelings we're doing such strange things to me. "Ysss." I gave a whimpered hiss, my little penis erect and tingling to his touch, I so wanted more. He began again then, but each smack was interspersed with his continued teasing. It was confusing me, the smacks hurt, but the feelings in my buzzing little penis was making me quiver all over. It was like a demanding itch, I wanted him to itch it more and more until I felt desperate for it. "You like me spanking you don't you girl." He spoke softly, his fingers teasing more. "Yss, ysss," I whimpered, I couldn't control myself anymore, the stinging smacks seemingly softer, more like stroking pats to my over sensitised cheeks, his fingers straying between them as he moved his hand to give me another. Suddenly I was aware of a voice, my voice, I couldn't control it, couldn't control myself anymore. "Ohhhh, ohhhhh, ohhhhhh, oh sir, oh sir, oh sir oh sir, oh sir." He stopped then, just holding me across his knees, my craving penis throbbing in search of his fingers, my body trembling as it had never done before. "Stand up girl, put your clothes straight." His voice was calm yet still so assertive. I struggled to my feet, somehow I almost felt cheated, my little penis was still stiff, tenting my panties, I so wanted to touch it, but I was too embarrassed to do something like that in front of him, instead I wriggled my skirt back down to try and regain some foolish modesty. He returned to his seat behind his desk and looked at me. "Stop wriggling girl." I tried to calm myself. "I think you enjoyed your spanking didn't you girl?" I couldn't speak, I just blushed furiously and whimpered softly. He took his time looking at me until I'd managed to get my emotions under some control. "Now, we have the business of the damages Rachel. You said you'd pay, but let me put that into perspective. First, I have to get some ecologists down here to assess the situation, they will probably have to stay here whilst they do their survey. They will then go away and prepare a report and send it to me, then I have to agree to the work and they have to schedule it. They will then have to come down, perhaps several visits, to do what is necessary. They will probably have to stay over each time. You can see where I am going with this Rachel." I nodded, worriedly, becoming more and more aware of the scale and the cost of what I'd unknowingly caused. "So, have you any money to pay for this Rachel?" I felt near tears again and shook my head. "No sir," I mumbled. "No, I thought not, so what are we going to do?" "I, I don't know sir, I'm so sorry." I couldn't stop my tears. "Hmmm, you can turn off the water works girl, it doesn't work on me." He looked at me scornfully. "As it happens I have an idea. I happen to know some friends who are ecologists and I can arrange for them to stay here in my house, so that will help a little with costs. What I suggest is this girl, you will come to work for me on weekends and holidays, I will pay you, shall we say ?20 per day, but I will hold back ?10 per day to pay for the damages. You will continue working for me until you pay off your debt. That way you will earn some money whilst at the same time pay for the damages you've caused and learn to behave. What do you think of that girl?" I couldn't believe my ears, this was my chance, my opportunity to make amends. On top of that, I didn't get pocket money, Mum couldn't afford it and this was a chance to have my own money too. I nodded hopefully, for once completely forgetting how I was dressed and that he was calling me girl. "Yes, oh yes please sir." He smiled for the first time, but I was too relieved to understand his smile. "Good girl, now you can go and make me a cup of tea whilst I write out a contract. You know how to make tea don't you?" I nodded again. "Yes sir." The relief making me want to do anything to please him. He got up and unlocked his study door, then led me out through the big hallway down a dark corridor towards the back of the house. We emerged into a large kitchen. There he pointed out the necessary things needed. "Get yourself a glass of milk too girl and bring my tea and biscuits to me in my study. In this house you bring the teapot, milk jug and sugar bowl on the tray with the cup and saucer, remember that." "Yes sir," I nodded again, eager to please him. He turned to leave, paused, then opened a drawer beside the door, he pulled out a white frilled item and turned back to me. "You had better wear this to protect your clothes girl. Turn around." It was with mixed feelings, primarily embarrassment, that I stood and allowed him to tie the apron around my waist. When he'd tied the knot, he patted me on my sensitive bum, which made me jump. "Bring it to me in my study when it is ready." With that he marched out of the kitchen, leaving me alone for the first time since he'd discovered me on his river bank. Uneasily I made his tea while pondering my own stupidity in letting this happen to me. Yet I was also feeling strangely mixed up inside my head. On the one side a silly, submissive, girly feeling a lot like the way that I felt when I had my own secret fun in my bedroom. Whilst on the other side, a deep embarrassment was burning inside me. I couldn't wait to run away and escape back to my own secret security, a lesson learned, a foolish mistake that I never wanted to make again. Eventually I nervously carried the tray up to his study, the door was closed so I put it down and knocked. "Enter." He sounded like a headmaster again. I brought the tray in and put it on the end of the desk where he indicated. "Take your milk and sit there quietly girl." He pointed at the big tall chair that he had sat in to spank me and that was still in its position. I took my milk, feeling like a child and sat on the chair, it was so high up I had to almost climb to get on the seat, but then I sat there drinking the milk and watching him. He poured out his tea, nonchalantly stirring in milk and sugar, then continued working on his computer. I felt terribly uneasy yet I only watched quietly, desperate for him to finish so that I could at last change and leave. Eventually he grunted, the printer on a table behind him beginning to disgorge paper. "Right Rachel." I blushed red, shrinking in a horrific embarrassing reminder of that female name which I had hoped he had forgotten. I still couldn't understand why he was treating me like a girl. Yes, I foolishly had girl's dressing up clothes in my bag and yes, he had made me put them on, but surely he had seen that I was not a girl, he surely must have noticed I had a penis. "Here is a copy of your statement and the agreement that we discussed. Read it through and sign the last page to confirm your agreement with what is stated within it. So that you understand, It is in three parts, the first is your statement regarding your trespass and the damages that you caused. The second is the agreement on your repayment of costs for those damages and the third is a contract of employment. Read it through carefully and sign it to say that you understand its contents and that you agree to the terms and conditions of your contract together with the repayment of your debts." He picked up the wad of papers and handed them to me and I began to read them through. The first page began with a harrowing description of how I was found trespassing on his property. It outlined how I had changed my clothes and was caught dressed up in a disguise with my own clothes concealed in my bag. It described the area that he had found me in was one of special scientific interest and it inferred about the ecological damage that I had caused in an area where rare and specialised plants were growing. It then went on to describe, that on questioning I had admitted my guilt to him and that for legal evidence my admission had been recorded. The recording was stored on a computer file that was in his possession, a copy of which was being sent to me for my own records. It went on to say that I had fully and readily admitted to everything under no duress and as shown in the recordings. I was more or less scanning the sentences now; the legal terms weren't easy to read and in truth it embarrassed me greatly to read about the full consequences of my foolish actions. I picked up the next page, hardly wanting to read more. It expounded on the discussion that had occurred between us regarding an agreed punishment for the misdemeanours to which I had admitted my guilt. It went into detail about how he had asked my thoughts on how I should be punished for my crime and how I had begged him that the best thing was to spank me and that after some debate he had eventually agreed. My begging and the ensuing spanking were also recorded as proof and once again with copies kept by him and sent to me. This was followed by a statement of my understanding regarding the damages I had caused and how in addition to the previous punishment I had agreed to pay for the survey of such and the repair of those damages caused. The second part of the document continued by explaining how I had agreed to work for him in order to pay off the cost of repairing the damage I had caused. It explained that half the money I earned would be taken to pay off my debt and that the debt would be subject to annual compound interest payments of 40 % APR on the total costs. On the next page the document flowed through into the contract of employment and it continued stating that any additional damages which I might cause during my employment, would be added on to my debt and that the contract would continue under the same agreement until all the debts were paid off satisfactorily. It then went on to say that I was expected to do the tasks allotted to me as instructed and that if I didn't do my work to the standard required, my wages would be docked for that period. Further to that it said that I must obey all and every order that I was given and that I must adhere to all the rules of my employment, a list of which was given on a separate page. I was getting confused by then, the writing looked odious and I didn't understand the legal terms. I had to agree that in general, much to my distaste most of what I had read was relatively true. I flicked through the heavily typed pages until I got to the end. There I found a page with my details and a place for a signature. Again, I skipped over the text not seeing the female under sex and not really noticing Rachel under my first name, in truth I was more focussed on getting it all over and done with, so I went straight to the signature line with its dots, ready for my signature. I took the pen he offered and I signed it, writing the date he gave me on the following date line. "Good." He nodded, then produced a few separate pages. "Whilst we have legally stated the situation and you have agreed to the contents of your statement and signed your contract of employment, as you are still of school age, you must also get the permission of your mother." I looked at him in horror. "Here is a letter to her explaining my offer of a job to you. It contains a very basic overview of your contract for her to see, together with a signature page for her to sign too," He handed it to me and I looked at it in fear. Surely he wasn't going to tell her about all this. "I will expect to see a picture of her signature on this document tonight. I have put my number into your phone and you will send me the picture after she has done it. If, for any reason she has not signed it, then I will personally come to see her to discuss this whole affair with her." He paused looking at me as I sat there trembling. "Is that understood girl?" I nodded tearfully. "Good." "Whilst we are discussing your phone, I have been through it and extracted the numbers for your mother and your sister, together with a few other random numbers which might become useful. I want texts and photos from you every morning and evening, I want to see that you are dressed properly and that you aren't trying to dress up as a boy again!" I looked at him aghast, speechless, a horrible trapped feeling flowing through me. "There, now that that is done girl, I want to take your measurements, you will start your maid's duties next Saturday morning and I want to have your uniform here for you by then." I looked at him startled by his words. "Mmaid sir?" He unnerved me so much, it was just a mumble. "Yes of course girl, as your employment contract stated, if you read it fully, you will work as a housemaid here at weekends, high days and holidays until further notice, that is what you signed in the contract. Is that clear?" I blushed pink as I looked up at him. A maid, oh my god what did he mean a maid, I thought that he was wanting me to be out in the woods making good what I had damaged. "Put your papers on my desk and stand up straight girl." He opened a drawer in his desk and took out a tape measure. The measuring process itself was a horrible embarrassment, he could tell that I was a quivering nervous wreck as he did it, him writing down each measurement in turn as he took it. When he was satisfied he replaced the tape in the drawer together with the page of measurements then turned to me once again. "I want you to be completely aware. You might not know, but I am a Justice of the Peace for the county. If there is a sign of any backchat, disobedience or nonsense and you break your legal agreement as stated in these papers then I will be taking you to court. That means, as you are still under your mother's guardianship, I will be taking her to court too. I will have to explain everything to your mother and show her the signed documents, together with the recordings made today. If a court case was to be brought, then these documents and recordings would be publicly available. The minimum you would expect in court is a claim for damages and a claim for breach of contract, though trespass and attempted robbery could be conceived too. You can imagine what the consequences of those things will be, not only to you but to your family. Do you understand girl?" His voice was strident and arrogant. I nodded almost in tears. "Ys Sr." "Good, so now I want you to clear the tea things away, bring them to the kitchen, wash them, dry them and put them away, then tidy up all the things in the kitchen that you have used. Do you understand?" I stood there stupidly, feeling foolish in my girly clothes, the frilly apron tied tightly around me exacerbating my appearance as I nodded miserably. "In the mean time I am going back to the woods to take pictures of the damage and to retrieve your bicycle whilst trying to minimise any further ecological damage. If I am not back by the time you finish, then stand and wait for me in the kitchen. I will put these papers in an envelope for you to take with you then." I gathered up the things onto the tray under his watchful eye, I dared not look at him so I didn't notice the evil smirk that he had on his face as I left for the kitchen. The next I heard was the front door closing with a bang and all was silent. I sobbed a bit then as I did the task he had given me. They were tears, in part due to fear of him, but in reality, mostly due to my own frustration and stupidity at what I had done. Yes, he was treating me terribly humiliatingly, but in truth it was all my own fault. The only weird thing that kept going round in my head was how he kept on insisting I was a girl, yet surely he had seen that I wasn't. I had no explanation to the bag of girl's clothes I had with me, I know and I had stupidly told him my name was Rachel. Idiot, idiot that I am, what else could he have thought, I suppose, other than I was a girl. In my mind I decided that I would have to come clean, tell him I was going to dress up as a girl because in an embarrassing way it excited me, but I was really a boy and that I had learnt my lesson and would never do it again. It seemed like as good an idea as any, but then another idea came into my head. I'd finished in the kitchen, so if I hurried into his study, I could find my clothes and put them on, then escape out of the front door. I smiled to myself for the first time since he had seen me and with a pounding heart rushed out to the hall across to the door to his study. I turned the knob, hurrying to get inside. My shoulder banged into the door and it didn't move. I rattled the knob and pulled and pushed, but there was no doubt, the door was locked. I felt deflated, disappointed, I looked at the door one last time, then returned despondent to the kitchen. I stood there a moment looking around myself, there was a door into a utility room, I opened it and saw the back door at the end of the room. The key was in the lock, it beckoned me and I tiptoed over to it. With nervy fingers I turned the key and the door was suddenly unlocked. It swung open easily and there I was standing on the step outside, in the warm sunshine and I was free. But I wasn't free, not really, I was dressed in the most sissy girlish clothes that I had stupidly chosen that morning and the frilly apron was not helping at all. Instead of feeling free, I was actually feeling highly nervous and in actuality completely scared at being seen dressed like this. I glanced about me listening very carefully, what could I do? What could I do? I could make a run for it, yes, but where would I go dressed like this? There was no way I'd walk back home like this, what would people say if they saw me, I'd be a laughing stock, I'd never make it. The sound of the front door banging closed made me jump from my querulous reverie and with a sigh I went back inside, closing the door behind me. With any luck he would give me my clothes and bike back now, and then it would be all over. I would deal with the other issues when I was back home and I could think straight, I definitely couldn't think straight here, that's for sure, not dressed like this I couldn't and certainly not after the way he'd made me feel when he'd spanked me. I just got back into the kitchen in time before he opened the door to the hallway. "Come along Rachel." His tone was abrupt and I followed him meekly, the tremble flowing through my body once again. We went into his study, the door was open, he had obviously unlocked it when he had returned. "Pick up you bag girl." He stood by his desk watching me as I nervously picked it up, hopeful of changing back into my boy clothes. "Here are your documents and your mobile phone, put them into your bag." He handed them to me and kept watching as I hesitantly put them in with my clothes, which were begging for me to change into. "Now follow me girl." I followed him my heart pounding nervously, where was he taking me, oh god not outside, not again dressed like this. I hesitated on the step outside the door and he pushed me gently onwards. My bike was standing there by the balustrade and he started to push it, leading me reluctantly and feeling very very vulnerable along a concrete path which lead past the kitchen garden. We walked silently for a while with me concentrating hard to hide as much of myself as I could behind my rucksack until he stopped and turned to me. "Stop that you stupid girl, behave yourself, put your bag over your shoulders and walk properly. I can see you're asking for another spanking before you go, aren't you?" I blushed bright red and nervously slung the bag over my shoulders, unable to look at him. "Hmmph," he grunted and continued along the footpath. It took us all of ten minutes longer to get where we were going, I was convinced he was going to send me home dressed like that and I was terrified, walking slower and slower as we proceeded. The path went through a heavily wooded area then emerged by a large grey stone built building. It was like a small house, to its side was a lean too garage and just in front of it were two pillars and a large iron gate, the main road scarily visible just beyond it, with cars regularly passing. He pushed my bike into the garage, then lead me over to the front door, which was to the side of the building, closest to the garage. "You'll find the key beneath that pot." He pointed to a glazed flower put full of pansies and he obviously expected me to get it. In a natural reaction I bent over to look, oblivious of the fact that in so doing I was revealing my panty clad bum to him. That didn't dawn on me until I felt his hand touching me and I hurriedly went to avoid his touch by bending my knees so that I was crouching. "Stand up straight girl." His voice was a gruff bark and I immediately popped back up, straightening, my shoulders back. "Now, try again and do it properly this time girl, bend over and get the key." The road suddenly seemed to get busier, several cars passed, one after the other. "Quick about it." I took a nervous breath, my head mixed up with feelings of humiliation, embarrassment and yet my little penis was tingling. Then I bent over once again, my satin covered bum in the air whilst my fingers sought vainly the key beneath the pot. The touch of his hand again, made me gasp, my fingers freezing in my search, his hand hot against me as it slid over my clinging panties, teasing me yet giving me a quivering reminder of my spanking too. "Have you found it girl? Have you? Is it there? Are you still looking?" His voice was soft almost hypnotic, the drone of the traffic fading into the background. I whimpered, still unmoving, his touch, his words somehow erotically making me stiffen and unable to move. His hand moved, joined by the other as they slid around my hips, holding me tightly and pulling me back against him, until I could feel his tweed trousers rough against my barely covered bum. "Are you still looking, Rachel? Are you? Or are you enjoying yourself too much you naughty girl." Whimpering softly I tried to regain my focus, my trembling fingers trying to move again, to reach for the pot which seemed further from me than it had been previously. "Are you enjoying yourself too much you naughty girl, are you?" In my mind I wanted to pull away from him but I felt so weak that I could only whimper. "Are you being a naughty girl Rachel? Are you? Tell me," That droning voice was eating into my head mixing with the humiliation of my predicament in such a public place. A slowing car a glance through the gate and what would they see!!! "Are you being a naughty girl Rachel? Tell me girl, answer me. Are you being a naughty girl?" My panties felt so thin that I could feel every touch of him against me. "Yss." I blurted the word out before I'd even thought about it. "Well you know by now what that means don't you Rachel, you know what's going to happen now." He released his grip on my hips, yet his one hand still stayed on my bum. "You'd better find that key quickly then hadn't you girl." In a total quivering embarrassment, I scrabbled around under the pot until I finally succeeded in finding it. I straightened up with it clutched in my trembling hand and I showed it to him. "Open the door then girl." I put the key in the lock and opened the door and he pushed me into the hallway inside. "This is the old gate house, when there isn't enough room in the house some of my extra visitors or staff stay here. Come along up the stairs." He lead me past a number of open doors, one was a small dining room, one a lounge with sofas and a large television, the last a small kitchen which was at the end of the hall by the foot of the stairs. He stopped there a second so that I could pass him and I made my way up the stairs with him following me. There was bathroom and three bedrooms upstairs, he directed me into the last bedroom. Inside, there was a single bed, made up, a bedside cabinet, a dressing table with a stool, a stiff backed chair and a large wardrobe. "Put your bag on the bed Rachel." I nervously did as I was told, worried and confused about what was happening. "Every day you come here, you will put your bicycle in the garage and come into the gatehouse. From now this will be your room, everything you find in it is going to be yours to use and enjoy, I expect you to keep it clean and tidy. On your bed you will either find your clothes and your uniform for that day, or you will find a note telling you what to wear and where to find it. That note will also include any other instructions which I will expect you to follow. You will change here, do your hair and put on makeup. I expect to see a girl wearing makeup, I believe that girls should look like girls, feminine, if I catch you pretending to be a boy again and wearing trousers or not wearing makeup then I will be extremely angry and there will be consequences. Your makeup and hair brush will be chosen by me and left on the dressing table. I will be sending you video clips on how to put on your makeup and I will be expecting nightly pictures from you showing me what you've done." I looked at him in complete horror, clothes were bed enough, terribly embarrassing, but makeup, that was the limit, I couldn't, I just couldn't. I opened my mouth to speak, to tell him that I couldn't do it. He interrupted me before I started. "Remember your contract Rachel," It was more of a threat than a statement of fact. I closed my mouth and a cold shiver went down my spine. He looked at me waiting a second to see any further reaction and then went on. "I'm glad that at least you have fairly long hair, but I want to see you growing it much longer and eventually you will have a perm, I like to see girls with curly hair, it makes them look sweet and innocent," He looked at me as he spoke, carefully awaiting my reaction to his words, pushing me further. I just stood there aghast, I couldn't believe what he was saying, he was teasing me surely. "When you have changed and done your hair and makeup like a good little girl, you will leave the Gatehouse, put the key back where you found it and walk up to the house. Go to the back door and go into the kitchen, wait there until I come. I will expect you there by 9.30 at the very latest, but this will vary. I will then inspect you to see if you have been obedient and done as you were told and if I am completely satisfied, I will give you your duties for the day. At the end of your working day, you will be free to return to your room in the gatehouse to change, Is that clear." I nodded unhappily, this was all getting much too much for me. "Now before we finish there is the matter of you being a naughty girl, again." I looked up at him in horror, my heart rate increasing dramatically, I thought he had forgotten about that. "But, But," I began. "Don't give me your buts girl. Outside, not five minutes ago you admitted to me that you were a naughty girl again, is that correct?" I couldn't look at him, the scene flashed through my mind and I felt my cheeks burning a deep red. "Well?" He paused. "Did you just admit to me that you were a naughty girl again?" You could cut the silence with a knife. "DID YOU?" his bark made me jump. "Yys ssr." The stuttered reply left my lips even before I could think, but it was true, I had stupidly admitted that I had been a naughty girl again. "YES, Yes you did girl" He paused for a second. "And what happens to naughty girls?" My heart was pounding, I was trembling all over and yet my little idiotic penis was tingling like a mad thing. "Come along Rachel, tell me what happens to naughty girls?" "Th they get s spanked ssr," I whispered my cheeks bright red. "Were you a naughty girl Rachel?" There was a dramatic pause as he waited my reply. "Ys Sr," I said eventually, my words were but a quiet whisper. "So, what should happen to you girl?" I was backed into a corner there was no way to avoid it, but in truth the growing tingling in my penis was turning me into a submissive wreck. "What should happen girl?" "S sspank," I began. "Speak up, say it properly girl." "I, I sh should be s spanked again s sir," I mumbled, my face burning even more, yet my unfathomable penis was buzzing madly even as I said it. "Ask me then girl, ask me to spank you because you've been a naughty girl again." I looked at him in burning humiliation, but deep inside I knew that I needed to, wanted to, say it. He was looking at me expectantly, waiting for my reply. I whimpered slightly, I couldn't help it, then mumbled my words. "P, p please w, will you, will you s, spank me again p, please s sir. I, ive b been a a a naughty g girl again s sir." My penis pulsed stupidly even as I said it. He pulled the chair into the middle of the room, sat down on it, then pointed to his lap. "Come along then girl, over my knees." He was serious and assertive, I couldn't look at him I was so embarrassed and I missed seeing the leer on his face. I nervously inched forward towards him until he stretched his hand out and pulled me forward over his knees once again. I almost fell, sliding awkwardly across them but he caught me and he adjusted my position until my head was once again almost touching the floor. Slowly then, ever so slowly, I felt him lifting my skirt, pulling it up to my waist, his left arm wrapped around me pulling me closer to him and holding me tightly. His right hand rested for a minute, gently on my satin covered bum, softly rubbing my twitching cheeks through those clinging panties. "You want me to spank you don't you, you naughty girl? Hmm?" I felt his left hand snake under me once again, this time into my panties and between my legs until it touched my little buzzing penis. I whimpered softly, wriggling, expectantly, I couldn't see his dominant smirk, only feel his touch. Gently he pushed my penis backwards between my legs, keeping a pressure on my pubic mound to hold it there. He pushed my little throbbing thumb up between my testicles pressing it tight against my clinging panties. The feeling immediately began to drive me insane. "You are a naughty little, girl. aren't you? Tell me you want me to spank you then, you naughty little girl. Ask me nicely, ask me nicely to spank you." The feel of his hands, one on my bottom softly circling my cheeks and one pushing my pubic mound pushing my little pulsing penis between my legs and up against my panties, was eating into me. It driving a submissive arousal that was twisting my mind until I couldn't think straight anymore. Suddenly I wanted to say it, I wanted to beg him I needed to beg him, I wanted that feeling again, so much. "Ohh ohh, yes yes I im a a naughty little girl s sir, a naughty little girl, ohh please please sir ss spank me ohh please please spank me. His first stroke made me jump, it was a surprise, even though I'd just begged him for it. He continued then with sharp stinging smacks which I'm embarrassed to say, made me begin to squeal like a girl and which brought tears to my eyes. I wriggled trying to avoid them, but as he persisted and I rapidly deteriorating into a sobbing quivering wreck, until I finally stilled, broken, my legs akimbo as I lay submissively across his knees. He slowed then into a gentler more rhythmical spanking and each time at the end of every smack he softly slid his hand down between my legs over and around my testicles, teasing the head of my entrapped penis, before returning the next smack. It was giving me the most curious twisted mixture of feelings, the smacks stung my poor hot cheeks, but the teasing onward stroke between my legs touching my genitals was wonderful. I began to steel myself for the smack whilst spreading my legs and lifting my hips to meet the caress that culminated in that incredible wanton teasing of my little penis. My brain was slowly becoming confused, at one time lifting to meet the erotic stroke, at another lifting to meet the stinging smack until they both seemed to mingle. Eventually he had me in a complete arousal, almost begging for more, I so wanted a climax. I was whimpering incessantly, but he could tell when to stop and he did, leaving me on edge in a frustrated heap on the floor as he stood up adjusting himself. "I have to go now girl." His voice sounded gruff. "I have a meeting I have to go to." He looked at his watch. "I want the picture of your mother's signature tonight and make sure you are here bright and early on Saturday." With that he turned and left me sitting on the floor, my legs apart, my skirt still up around my waist. It took me an age to pull myself together and eventually I stood up, my legs feeling like jelly. I closed the bedroom door, completely unaware that all the rooms in the gatehouse were covered by CCTV, then still trembling I picked up my rucksack and emptied it out on the bed. I put the envelope with the documents and my phone on one side of the bed and my clothes on the other. Hurrying now, I stripped off my trainers and socks, then my skirt, my tee shirt and the camisole top and finally my very moist satin panties. Naked, I looked for my pants, desperate to get them on and return to my male normality. Only they weren't there, I couldn't find them. I thought I must have dropped them and I got down on my knees to search the floor for them, but they were nowhere to be seen. I felt panicky, they must have been dropped, perhaps at the river, or worse still in his study. I stood nervously debating what I could possibly do, before finally making a decision. I wasn't going to go bare beneath my loose shorts I'd be showing everything as I cycled along, so my only option was to put the panties back on again. With some reluctance I did that, the trouble was, that just putting them on sent me downwards in a submissive sissy spiral once more. Trembling again and with my willy tingling stupidly again, I pulled my shorts up over my panties and turned to get my vest and tee shirt. At least they were there, putting them on I began to feel a little more normal and hurried myself to get out of there. Only my socks, but again they were missing, I searched under the bed once more, but I knew deep down that it was futile, they were probably with my pants. Finally giving up, I once again put the girly ankle socks back on, then wearing my trainers I tried to shake off the submissive sissy feelings that kept flirting with my brain and I packed my rucksack and headed out as quickly as I could. I got home by late afternoon, my bum tender and still stinging, slowing my journey as I had had to cycled along in my discomfort. When I finally arrived, it was later than I had anticipated, I had barely a half hour before my mother and sister were due home. The note from the morning was still on the table. "Make sure you put the potatoes on to cook, the casserole is in the slow cooker, check it and give it a stir." Hurrying, I dropped my bag in the hallway, ready to take it upstairs when I'd finished and I swiftly got the potatoes on to cook before dutifully and much later than it should have been, stirred the casserole. I looked at the clock, I was feeling very nervy. It was five o'clock, they'd be back anytime, I hoped Mum would be back before my sister, I really couldn't face her at the moment, she had a way of picking up on all my secrets and teasing me mercilessly about them. Which reminded me I had to change my socks and those damn panties that I'd foolishly chosen to bring with me that morning. But first I had to hurry and finish laying the table for dinner. I knew that if I didn't, I would have all sorts of rows and complaints about how lazy I was. I'd just finished and was heading back out to the hallway when the front door crashed open. It happened so suddenly that it made me jump and broke my silent reverie. My sister came blasting in, looking at me, an immediate suspicious expression on her face. "What are you up to Richie?" "NNothing Di," I stuttered, immediately blushing. "You're up to something I can tell." Then she looked me up and down and smiled. "You've been playing dressing-up, again haven't you?" she paused, her grin widening. "You little sissy." It was she that had caused the whole dressing up thing to take over my head in the first place. It was she that had planted the seeds that I constantly struggled to be free of. It was she that had forced me to dress up and play her evil games all those years before. And now my face was on fire, my heart in my throat. "N noo Di, I I haven't," I babbled, a horrible nervousness immediately growing inside me. "Yes you have, I can tell, I know how much you love it and I know when you're lying sissy, you'd better not have been wearing any of my clothes." She looked me up and down and it made me shrink in dread. "I like your girly socks by the way, they suit you!" She had a broad evil grin now, she knew exactly what she was doing, she just loved to humiliate me. The socks, the socks oh my god the socks. I should have changed them, if only I had when I'd got in, My face was immediately on fire with the embarrassment. "I bet you're wearing sissy panties too, aren't you?" She was so mean; she was enjoying every minute of this. I shook my head violently. "Noo, noo, I I'm not Di, I I'm not, honest I'm not." "Show me then sissy. Let me see if you're a little liar or not" She was walking purposefully towards me, along the hallway, the front door slamming closed behind her. She had that evil expression I knew so well and I knew that she wouldn't take no for an answer, she'd caught me out and forced me to show her things before. "Please Di, please." I was so embarrassed I was almost in tears. "Show me now sissy, or else." She spat the words out, she knew I was afraid of her, I always had been. With a huge fearful reluctance and with quivering fingers, I slipped my shorts down a little until she could see the top of my panties. "Right down, let me see. NOW" She barked, with the sound of an anger that I knew she was capable of. Whimpering, I pushed my shorts down until they dropped to my ankles, I felt in a hell of complete and total humiliation. The clicks made me glance up just in time to see her using her phone taking pictures and with a little squeak and a burning face I hurriedly bent to pull my shorts back up as she filmed the whole thing. "What pretty sissy panties." She was smiling gleefully. "I knew you'd be wearing panties, you sissy; I can always tell." I was burning in embarrassment "Perhaps I should tell Mum what a sissy you are, what do you think?" A cold shiver went down my spine. "Noo, noo, please, oh please Di, noo," I begged, tears filling my eyes. "Well you'll have to be a good girl and do as you're told, won't you sissy?" She was still grinning that awful evil grin. "Or should I show her these pictures?" She waved her phone at me. I shook my head in horror. "No, Nooo, Please Di, please," I whimpered. "Well you'd better get back into the kitchen then, and get our dinner all ready before she comes home, hadn't you." I nodded in submission, feeling broken. "Y,yes Di." I was still trembling as I headed into the kitchen, thankful that the confrontation was over and glad to hear her heading up the stairs, leaving me to my inner embarrassment as I tried to focus on checking that the potatoes were cooked. She appeared a few moments later however and to my surprise she was only wearing her bra and pants. She is a big girl, tall and muscular with an androgynous look and this was exacerbated by her state of undress. Her bra was a grey sports bra, her small breasts featureless beneath it and her pants, again they were grey, were a type of boxer shorts. She had big feet for a woman, size 11 and on her feet were sports socks. In her hand she was holding something bright pink and shiny. "Here put this on sissy, Mum won't want to see you making a mess of your clothes, will she?" Her aggressive directness left no space for argument, especially now. I was terrified that she'd show Mum the pictures she'd just taken. I took it from her, it was an apron, but in the colour and material I instantly knew what appearance it would give, I had no idea where she had got it from. "Put it on, get a move on or I will show her your pictures and I will tell her all about you." She stood there with her hands on her hips, scarily forceful. I had no choice, I put the frilled loop over my neck and then tied the ribbons around my waist. "Now get on with the dinner and if I see you've taken it off when I come down, then Mum will see exactly what you are like." I watched her as she left the kitchen again, her underwear moving over her lithe muscular body as she walked. Mum was late, but her arrival was before my sister had come back down stairs and I tried my best to put on my brightest smile as I greeted her. "Hi Mum, I've got the dinner all ready." She looked at me curiously, I really hadn't realised quite how much of a sissy I looked wearing that apron and with the ankle socks as virtually the only other visible piece of clothing I had on, it made matters even worse. She grinned a wide grin almost as if she was laughing at me. "Well look at you, where on earth did you get that apron?" There was scorn in her voice. A voice interrupted before I could speak, my sister appearing just beside me. "He saw it in a shop downtown, he begged me to get it for him. I thought it looked a bit...." She paused raising her eyebrows at my mother. "But, well if he likes it then that's all that matters don't you think?" I looked around at her, I couldn't believe what she was saying, it was all a complete lie. Mum studied me a second then laughed "Well if you like it and it makes you help out more in the kitchen then you must wear it all the time, mustn't you Richie." With that she walked into the kitchen as I stood there open mouthed, blushing to my roots. We sat down to dinner; I didn't want to tell her anything about the job in front of my sister so I kept quiet leaving them to talk as I toyed with my food. It was only after we had finished the casserole and were about to eat our yoghurts for sweet, that Mum turned to me. "I was late home because I had a phone call just as I left work Richie." I looked at her a knot forming in my tummy. "I had no idea you were looking for a job! Don't get me wrong, I'm delighted you are finally doing something, but you hadn't discussed it with us," She paused awaiting my reply I hesitated; I didn't know what she knew. "I, I was going to tell you Mum," I stuttered. "Mr Layton-Phillips, who owns the estate by the river, rang me and I must admit I was surprised, but he was very nice and explained it all." I looked at her blushing I was terrified what he might have told her. "He explained to me that he had approached the school about an opportunity for a job and that you just turned up. I was shocked, I didn't know what to say, but in retrospect all I can say is, well done Richie. I am pleased that you've shown some initiative at last, you know how tight money is and you're finally trying to do something about it. I am glad to say that this could be a brilliant opportunity for us all." She was smiling as she looked at both Di and me. "He told me that you would be given full training on the job, it would be minimum wage to start of course, but that would increase after you'd completed your apprenticeship." She seemed delighted. I nodded apprehensively, the real story buzzing around in my head. "Yes Mum." My sister was all eyes and ears, I couldn't look at her, I was terrified she'd find out what really happened. "It seems that you might be expected to live in at weekends and during your holidays, he asked me if that would be alright and of course I agreed. He said that if you got on well with your training and he was pleased with you, then it wouldn't be necessary for you go back to school, but you would continue your education with him." I looked at her speechless, this wasn't what I had agreed and wasn't what I wanted at all. She moved on, seemingly keen to get things sorted. "Evidently you have a document for me to sign as your parent and if he is completely happy, then you can start on Friday evening. Isn't that brilliant?" I just sat there blinking, feeling numb inside. "It's all so positive, he even said that he would be providing a uniform which you will be expected to wear in work, so that will save your clothes." She turned to Di. "He was such a nice man, he's a justice of the peace you know and he told me that he would be happy to meet up with me, he even said that he would take me out to dinner to tell me all about it and discuss any concerns that I might have, isn't that nice Di?" "Sounds great, you should take him up on that Ma, a free meal woohoo." Di turned to look at me. "Where's the form siss?" My eyes opened wide at the word and I glanced at Mum but she didn't appear to have heard, or at least she had ignored it. "It, It's in my bag Di," I mumbled. "Go and get it then, so that Mum can sign it. You should have had it all ready for her." I slowly got up and went out to the hallway, then opened the top of my rucksack and pulled out the large manilla envelope. This was all happening too quickly, I hadn't had time to sort through the papers. Mums part was in a separate white envelope inside the main envelope thank goodness, it had her name on it. I stuffed the rest back into my rucksack and covered it, then brought the white envelope through to the kitchen and gave it to my mother. She opened it and her and Di, started reading through the contents. It was fairly basic, just saying that I was offered the apprenticeship working in the house and that the terms and conditions of my employment were available for her to read in another more expansive document if she wished. It went on then with paragraph after paragraph of legal jargon and she skipped through it as I had done, until she came to the last page where it said that as my parent, she was in effect my sponsor. It continued with an explanation that as my sponsor she would be held responsible if there was any default to my contract or issues regarding my work ethic. At the end her details were typed and a space for her signature together with the date. "Well that sounds about right Richie, pass me my pen from the work surface over there." Feeling suddenly very nervous, I almost dropped the pen as I passed it to her. She signed it with a flourish then pointed at that last phrase. "It says here about default to your contract or any issues with your work ethic then I will be responsible!" She looked at me seriously. "I don't want to hear of you defaulting on your contract or that there are any issues about any work ethic, whatever that means. You do as you're told, just you make sure that you behave and do whatever he says and if I get to hear of any issues about you not doing as you are told or being a lazy sod, then I'll personally sort you out. Understand?" I nodded again. "Yes Mum." My voice almost broke, It was no more than a whisper. Meanwhile Di was carefully reading the pages of writing, a gleam in her eye and a smirk on her face as she read. Mum seemed to want to get things sorted and out of the way as soon as she could. "You have to take a picture of this page with my signature on it to send to Mr Layton-Phillips, he said that if he didn't have it by tonight he could assume that I hadn't agreed, well I do agree, so don't hang about, hurry up and get your phone, take the picture so you can send it to him straight away." I went out to the hallway again, dragging my feet, unhappy about the whole situation. I rummaged around in my rucksack, my phone had somehow got itself entangled in the skirt and it popped out with it as I pulled. Panicking I shoved my skirt back into my rucksack and covered it up and carried my phone back into the kitchen. "Hurry up Richie, we haven't got all day." Mum slid the sheet of paper with her signature on it, across the table. I looked down at my phone and pressed the button on the side to switch it on, there showed three messages from "MASTER" I guessed it must be him. I swiped the screen to get to the desktop and froze. It wasn't my normal wallpaper, instead there was a picture of me dressed in the skirt and tee shirt in his study. "Look give it to me, I'll do it." Mum's hand was outstretched. I was panicking more now, but managed to open the camera ap just in time before she took my phone from me. She adjusted the position of the paper and focussed the phone before she took the picture. Then she took two more slightly closer. "Let's see what that looks like." I almost screamed, but luckily she could go straight to the picture from the ap without going to my home screen. "There, that should be ok, now send it to him," She handed the phone back to me. "Tell him I am very happy with that." I went to leave the room with my phone. "No Richie, do it here, now, in front of me, I want to be sure you've sent it, I don't want any last-minute changes of mind from you." I went back to my desktop, the wallpaper there making me quiver nervously just at the sight of it. Hurrying to hide it again I went into the picture of the document and selected the 'send to' command, it brought me to my contacts. At the top of the page in starred contacts was MASTER, I picked it and with trembling fingers typed Mum's message, then sent it. "I've done it Mum," I mumbled. "Now send him another message, ask him if it's possible for me to have a confirmation text from him to make sure that he has received the picture from you." She obviously didn't trust I'd sent it. "Ys Mum." My reply was quiet and I set about sending the new message she had given me. All this time, the pages of the document were clutched in Di's hands and she was watching my every move with a suspicious eye. It sent a shiver down my spine, I felt sure she knew something. Mum's phone bleeped in the hallway with an incoming text. "Fetch my handbag for me, then you can put the kettle on and get started on the washing up." I went out to the hallway and brought her bag in to her. As far as the washing up was concerned that was my duty anyway, it was one of the chores I had been given to make sure I did something for my keep. I filled the kettle as Di went into the lounge, the document still in her hand. Mum took her phone from her bag and was reading the text which I assumed he had sent her. She giggled a little and I heard a camera click, but when I glanced up, she appeared to be still texting. I started the washing up as she continued sending replies, surely that wasn't him. Eventually she too went into the lounge her phone still in her hand whilst I carried on with the washing up. I brought them both a cup of tea each after I'd finally finished, then gave an excuse so that I could finally go up to my bedroom, my rucksack clutched in my hand. My phone bleeped loudly as I got to my bedroom, I glanced at it, the message was from MASTER, it was him. I opened the messages, the earlier ones were about making sure my mother signed the form, then there were my messages to him with the picture of her signature and the request for him to contact her. The last message was a picture from him of me downstairs in the kitchen, it showed me in the pink satin apron standing at the sink, my mother had obviously taken it and sent it to him. Beneath the picture it said that he liked my apron and that as I was now officially his employee, he was going to ring me and I had better answer. Seconds later the phone rang. I was quivering all over as I saw his name come up, my finger hesitating over the button, but it was almost as if it answered itself. "Yes sir," I whispered into the phone. "You will call me Master from now on Rachel." His voice was deep and authoritative "Yyes Master," I whispered my voice trembling. "Good, now tell me what you are wearing girl." "The apron, my tee shirt, my shorts." I nervously started my reply oblivious of my mistake. "Shorts, Tee shirt! I told you that you weren't to pretend you're a boy anymore. You are not a boy, you are a girl, it seems to me that you are asking for another spanking girl!" He paused in his angry tirade. "Take those disgusting things off immediately and put on your skirt and the tee shirt you wore earlier, then take a picture of yourself and send it to me and quick about it girl." I closed my bedroom door then took off the apron followed by my shorts and tee shirt, then in a nervous unease, wearing only the sissy panties, I took the skirt, camisole and Barbie girl tee shirt out of my rucksack. I hurriedly put them on and took the picture, the intention being to strip them off again immediately after. The phone rang straight after, however and I nervously answered it. "That's better now put your apron back on over them girl and send a picture to show me." Again, I fearfully obeyed him and sent another picture. "That's more like it, now tell me where did you get the apron?" I took a deep breath. "I didn't get it Mmaster, my umm my sister gave it to me, she, she made me wear it Master," my voice but a low mumble There was a long pause. "She made you wear it? Where is your sister now?" "She, she's downstairs Master." My nerves were growing even as I spoke. "Get her, I want to speak to her." I could have died, I couldn't I couldn't, I didn't want to, "Ohh please sir," I began, whimpering now. "Get her, or I will ring her on her mobile myself." Felling like I was in sheer hell, I opened my bedroom door and crept out, perhaps as long as I kept facing her she shouldn't know what I was wearing under the apron. I tiptoed downstairs then lucky for me or unlucky depending on your viewpoint, I met her at the bottom, she was about to come upstairs herself. "Umm Di, umm please he, umm Mister Phillips umm wants to talk to you, a a second." I was trembling even as I said the words. She looked at me curiously. "What's he want me for?" I said nothing. "Ok come on, I suppose I'll have to see what he wants then." Now I was faced with having to turn around and go up the stairs in front of her, or walk backwards, I felt stuck, trapped. "Well come on then I haven't got all night." She sounded cross, snappy. I turned quickly with a slight sob and ran as fast as I could, but she saw what I was wearing straight away. "Ooo, look at you sissy, wearing a pretty little skirt, just what a sissy like you needs." She reached out and smacked my bottom as she followed me laughing as she came into my bedroom. I felt so embarrassed I was almost in tears, but she revelled in my embarrassment and held her hand out for the phone. "Give it here then." "Yes hello," They entered into a conversation together and of course I could only here her side. She sat on my bed and chatted away to him for ages and it was only later that I discovered the gist of the conversation. He asked her if it was true, she had bought me the apron and she told him that it was. He asked her where she bought it and she told him. Then he asked her why she had bought it for me. She was brazen in her answer and her explanation made me cringe in total humiliation. She told him quite blatantly, that I was a sissy and that she liked to tease me. To her surprise he seemed very interested in what she said and asked her for more information. She then told him all about our relationship, she said that she had dressed me up as a little girl when I was a child. She told him that it excited her and she had kept it up until she left school. She told him then that, she thought she had turned me into a sissy and she laughed loudly when she said it. He listened to her with interest, he told her that he had suspected that there had been something like this behind my attitude. It seemed then as if he was considering something as he was quiet for a while and she thought that he had put the phone down, she was asking if he was still there. He told her that he was, then he asked her, did she still want to make me a sissy? She answered immediately with an affirmative, smirking at me as she said it. He considered her reply then asked her if she would in future make sure that I was dressed 'properly', that I was obedient when I was at home and to keep him informed of everything that happened when I wasn't in work. She readily agreed, smiling almost gleefully at me as she did so. He seemed very pleased then surprised her by changing the subject, asking her if she liked to go out to nightclubs. She said she did, but couldn't often afford to go very often. He asked her if she had been to the new nightclub in a nearby town and she said she had heard about it but she hadn't been there. He said that he knew the manager well and asked her if she would like to go and she said she would love to. He told her then that he was far too old to go to nightclubs himself, but a young friend of his was keen to go and would love to take her, he said it would be his treat and if she liked it, he would arrange for her to have free membership. She was delighted and he told her that he would arrange for this friend, Tom to pick her up at 8.30 on Saturday evening. She was about to finish the conversation when he stopped her a second with another request. "Would you do me a favour too Di?" he asked, using her name as if he was her best friend. "Yes of course," came her reply. "Remove all Rachel's male underwear, I don't want her to pretend to be a boy anymore." She chortled loudly, Rachel, woohoo, what was this then, it was like all her dreams and fantasies had come true, she was grinning wildly. "Yes of course, I'll do it, no problem." "Also has she a nightie to wear in bed, Di?" She loved this gender twisting thing, she had always hated the fact that Richie was the son, not her. In her head she was fiercely jealous that he was the male in the house. "No not that I've seen," she replied. "Could you arrange for that too? Perhaps you or your mother might have an old one somewhere that might fit." "Don't worry, nothing is thrown out here, I'll find him, er her, Rachel, something appropriate to wear." And she laughed loudly into the phone. He was pleased, as was she and they ended the conversation having promised to keep in touch. Richie stood there looking at her in abject misery. "If you don't do as I say Rachel." She highlighted the name. "Then two things will happen, I will show your pictures to Mum and I will ring Mr Layton-Phillips and tell him. Understand?" I nodded miserably. "Get all your boy pants and any vests and socks too and put them on the bed, get a fucking move on sissy." Sobbing I emptied my drawers, there were frugal amounts, but soon they were piled on the bed beside her. "Now take off your apron a minute." I did so in burning embarrassment and stood there in my skirt and Barbie top, I should have guessed what she was going to do, but never the less I was shocked and humiliated when she took photos yet again. Leaving me for a minute she headed out onto the landing. There, she opened the airing cupboard door and returned with a large cardboard box. I'd seen it before, I knew exactly what it was, it was what we called the rag bag, but in reality, it contained all our old clothes. I'd rummaged through it many times, finding things for my hidden dressing up stash. She rummaged in it now and soon produced a pile of different female underwear and several nighties. "Put them in your drawers Rachel." She sounded abrupt and snappy, but I didn't realise that she was also flushed with her own arousal. This had taken her back to her schoolgirl domination of me and it was exciting her. I did as I was told, I was afraid of her threat to do otherwise, though she made me keep one of the nighties out for that night. Then she did a most curious thing. Smirking at me, she pulled down the slacks she was wearing then to my shock she pulled off her grey women's boxers too. She looked me in the eye as she stroked her naked self. I could see she was wet, my eyes were out on stalks as I looked at her, all thoughts of my own embarrassment temporarily fading, a tingle going through my little penis, my hand drifting down to the hem of my skirt, wanting to stroke it. She picked up a pair of my pants and looking straight at me, she put them on, they fitted her perhaps a little tightly, but she pulled them up anyway. Smiling wickedly, she took one of my socks from the bed and shoved it down the front of the pants adjusting it as she looked in the mirror. I suddenly realised that she was now looking more like a man than a woman, yet my little confused penis seemed to be buzzing more than ever. She pulled her slacks back on over my pants, the bulge at her groin noticeable, then before she gathered up all the things that I'd put on the bed she turned to me again, her hands on her hips. "I'm the man in this house now sissy and don't you forget it, so you'd better do as you're told in future. Now put your apron back on, then go and kiss Mum goodnight, tell her that you're tired and want to go to bed early and let her see that you're wearing that little sissy skirt. I'll be checking up with her after! Now hurry up and get back up here when you've done it, change into your nightie, but make sure you leave your sissy panties on and go to bed like a good little girl." Her laugh was coarse, evil and yet full of some unbelievable aroused animal lust. "Remember I will be checking on you." She paused smirking at me. "Rachel!" I knew that it was no use begging her and I knew only too well if I didn't do it, then god knows what the terrible implications would be. I dragged my heels as I headed out of my bedroom door and I slowly went down the stairs. Saying goodnight to Mum was usually no big issue, even though it was still early in the evening. Her telling me to show Mum that I was wearing the damn stupid skirt was another thing all together though. I opened the lounge door, Mum was watching the TV with one eye, her phone still in her hand, she was in the middle of texting someone. "Umm, I, I'm going to go to bed early Mum, I'm really tired and I've got school tomorrow." I'd thought up the excuse as I was coming down the stairs. She looked over at me. "Before you do, go and get me a can of coke from the fridge, will you?" She seemed to be her normal self, even though she appeared to be quite excitable. I nodded. "Ok Mum." Then taking my life into my hands, the nervous embarrassment eating into my very soul, I turned and walked away from her. I walked across the hall and into the kitchen, more than aware of the coolness around my thighs, tickling me, a constant reminder of what she could see. I felt sure that she must have seen what I was wearing and I steeled myself for her call, her embarrassing question, but thankfully she didn't call after me. I got the can of coke from the fridge and took a glass from the cupboard, half filling the glass I brought them both back to her in the lounge. She stopped her texting again as I entered. "Put it on the table." She pointed to the coffee table and I bent down putting them there for her. "I'm going to go to bed now Mum." I glanced over at her, trying to calm the nerves in my voice. She smiled a thoughtful, almost distracted smile. "You make a good little maid don't you." I felt the blush heat my cheeks and I did my best to smile back at her before escaping hastily back up the stairs. Di was waiting in her bedroom doorway, smirking as she rudely groped the bulge in her pants. "Get your nightie on and get into bed now Rachel." She could hardly hide her evil pleasure as she spoke. "And remember to keep your sissy panties on. I will be checking. I'll give you 5 minutes." I scuttled off into my bedroom feeling horribly humiliated and in fear of her further recriminations I hurriedly took my clothes off, all except, that is, the dreadful panties. I picked up the nightie that was left on my bed, I hardly dared look at it. It was a young girl's nightie, one my sister had reluctantly worn many years before, it was lemon in colour with a picture of a teddy bear printed on the front. I pulled it over my head with a mixture of feelings coursing through me. In reality, if I had worn it in one of my private closet play sessions, I would have loved the feelings it gave me putting it on, but in this situation, it only served to build my humiliation. The nightie came down to my upper thighs revealing glimpses of the panties that I now hated, and yet did I? The confused thoughts they gave me flared even further embarrassment within me. Trying my best to ignore my inner torments, I slipped into bed pulling the duvet up to my chin. I waited in a mixture of apprehension and fear, yet there was a stupid gentle tingling between my legs She kept me waiting in suspense for another five minutes before she came in through my bedroom door. "Let's have a look then Rachel. Show the man of the house what you're wearing." The smirk was ever present on her face and she came over to my bed lifting my quilt so that she could see me. I closed my eyes in embarrassment as I felt her lifting the hem of the nightie making a thing of looking, even though I was sure she could see anyway. "What a good little girl," She laughed coarsely "I'll be checking you again in the morning so make sure you're still wearing them, or else." I couldn't meet her eyes, I was blushing, unable to speak. She turned out my bedside light then. "Night night 'Rachel'." You could cut the sarcasm in her voice with a knife. "I'm going downstairs to have a chat with Mum now. I wonder what she'll have to say about you, sissy." She was still laughing as she closed the bedroom door leaving me in the dark. It was only eight o'clock and here was I in bed like a child. My head was full of anguish and latent humiliation it was buzzing round and round. I thought that I would never sleep, I was constantly reliving every second of it all. I knew deep down that it was all due to my own stupid fault, yet I did feel tired, the humiliation the harrowing embarrassment all made me feel very tired, sleep overcoming me sooner than I would ever have expected.