Uncle Roger - Part 3 free porn video

I could barely stop thinking about my last visit to Uncle Roger. What we had done was very wrong, and I felt ashamed and disgusted. I was also extremely confused and conflicted - Roger had insisted that I had acted voluntarily, and that he had simply encouraged me. Encouragement is one thing, but coercion is another, and I wasn't sure whether he had crossed that line. At first he had blackmailed me into wearing girl's clothes, threatening to tell my mother that I'd been snooping through his daughter's old clothes. My mum had already caught me taking her underwear, and had since made it clear that she didn't trust me, so I knew she'd probably believe Uncle Roger's story over mine. But if I was honest with myself, Roger no longer needed to force me to dress up. I loved dressing up and doing my makeup, and I was no longer embarrassed when he saw me dressed as a girl. I was even coming to terms with him calling me Jessica. Although I had put up a struggle when he first tried to kiss me, when I gave into him and kissed him back, it made me feel femimine, sexy, and desirable. But when I remembered sucking his cock, his hands clamping my head in place, I felt violated and nauseous. While it was true that he hadn't physically forced his penis into my mouth, I didn't feel I was given any choice. I kept thinking about it, going over the events over and over in my mind, asking myself what I could have done to prevent it - and questioning whether I tried hard enough. Had the alcohol and cannabis made me susceptible to his advances? Or did I make a voluntary decision to submit to his wishes? But I was sure of one thing - he was calling the shots. He was in control. I was still practising my feminine deportment as Roger had instructed, walking and sitting in an elegant and graceful manner. Part of my "homework", as he called it. I was also practising my makeup skills as often as I could, and studying the makeup book he'd given me with far more attention than I had ever paid to any school textbook. The makeup set he had given me was large and comprehensive, containing eye shadows, mascara, eyeliner, lipsticks, foundations, and blusher. I had carefully hidden the conspicuous pink box, so that I had to fully remove a drawer from my wardrobe to get to it. My parents didn't give me much time to myself (I wasn't trusted to stay home alone ever since my mother found out I'd been taking her underwear), so it was difficult to find the time and privacy necessary to practise properly. I would often pretend to be taking long baths as an excuse to lock myself away in the bathroom. But I wasn't doing this just because Roger had told me to - I was doing it because I loved to do it. So while a whole weekend at Uncle Roger's place was on one hand a welcome opportunity to dress up and spend more time as Jessica, I was extremely worried about what he might have planned for me this time. But I had no choice, my parents had already decided to leave me with Roger while they went to Scotland. So on Friday night I carefully shaved my whole body, just as he had told me to, knowing that he would want me to look as feminine as possible. --------- My parents dropped me off at Uncle Roger's house early on Saturday morning. They were on their way to catch a flight to Edinburgh, and Roger seemed barely awake when we called round. "I'm so sorry to trouble you again, Roger," my Mother told him. "Hopefully this will be the last time we need to leave Jamie with you." "Oh, no problem," he replied. "He was a bit more cooperative last time he came round, so hopefully this weekend will be a breeze." "Well, for a former teacher, you don't know much about teenage boys!" "No I suppose not," he laughed. "Teenage girls are more my speciality." "Be good, Jamie" my mother said, turning to me. "Make sure you do your homework, and do your share of the chores." Uncle Roger took me inside, as my parents sped away to catch their plane. "I'm going back to bed. You will go and get changed immediately, do you understand? I do not want to see you dressed as a boy again this weekend. Did you bring your makeup?" "Yes sir, of course." "Good, so you know what you have to do. I hope you have been practising. When you're ready, you can start on your homework. I will check on you in a couple of hours." And with that, he disappeared - he obviously wasn't much of a morning person. Excited at the prospect of some time to myself, I went up to the spare bedroom, and found exactly the same clothes as I had worn last week. I immediately picked up the beautiful tan stockings, and the soft, luxurious, ivory colour lingerie. I couldn't wait to take off my boy clothes and put it all on, but I did so slowly and deliberately, savouring every moment. First the silky panties, then the gorgeous padded bra, and then the suspender belt. Finally I slowly rolled the stockings up my legs, and attaching the suspender straps to each one. I sat at the dressing table in my lingerie, and decided to try something a bit different with my hair. On my first visit, Uncle Roger had tied my hair in bunches, and I had repeated the style myself the following week. But bunches were more suitable for a six year old than a sixteen year old. And my hair was long for a boy, so I had a few options available. I started by brushing my hair thoroughly to get rid of any knots, and then pulled most of my hair back into a pony tail. I created a side parting at the front, so that one side fell over my face, and held it in place with a little hairspray. It wasn't perfect, but looked quite passable. I secured the pony tail in place with one of the ribbons he had left out on the dressing table. It was time to start on my makeup. All the practise was paying off, and I applied a simple 'day look' that I'd learned from my book - foundation, setting powder, a subtle eyeshadow, eye liner, and a light bronze lipstick. I then put on the remaining clothes - the school uniform consisting of a grey pleated skirt, white blouse, cardigan, and simple black court shoes - and made my way downstairs to start my homework. I laid my homework out on the dining table, and started working away. It was starting to feel natural to be dressed like this, I found that I could even concentrate on my work without feeling too self concious. Although, of course, I was still worried about what Uncle Roger might do to me... I had to find a way to tell him that it couldn't happen again, but without making him angry. "Good morning, Jessica" he said, walking into the dining room. "Good to see you hard at work. You look beautiful this morning." "Thank you sir," I replied, blushing. "Your hair looks lovely, very cute and feminine. I like what you've done with your makeup, too, I'm really glad to see you've been practising. Now, I will have cereal and juice for breakfast, please don't keep me waiting." "Yes, right away, sir". I went into the kitchen and got Uncle Roger his cereal and juice, grateful that he wasn't demanding a full English breakfast, and brought it to the table, where he had settled down with the morning newspaper. "Good girl. Thank you, you may put it down on the table. I'm so glad we have the weekend to ourselves, Jess. It's going to be a lot of fun." "Yes, sir. But please... what we did last week... it can't happen again." "What thing in particular, Jessica?" "You know. The things we did. Together." "Do you mean when you gave me a blow job?" "Yes sir," I replied with my head held in shame. "It was wrong of us." "I didn't force you, my darling. It wasn't all one way traffic. It wasn't just me kisssing you, and you seemed more than happy to drop to your knees." "But sir," I protested, unsure if his version of events tallied with my own. "Regardless of what happened, it can't happen again. I've been feeling guilty and ashamed all week. I can't look my mother in the eye." "I see. We can discuss this again later, but I won't force you to do anything like that again if you really, really don't want to do it. But I do demand obedience in every other respect. Understood, young lady?" "Yes sir," I replied, relieved. That had actually gone better than I had dared hope. "Of course. Thank you." "Now, while I'm eating my breakfast, I want you to show me how your walking is coming along. Show me how graceful and feminine you can be. Walk the length of the room, out through the door, and then back in here, with a little twirl at each end. Keep on going until I tell you to stop." I started walking, moving as smoothly as I could, my head held high, and my back straight. I placed each foot in front of the last, slowly and carefully, my stocking clad thighs rubbing gently against each other, my hips swaying gently with each step. I was still not really used to walking in heels - even though they were not particularly high - but I was improving, and the movement and the balance was becoming easier and more natural. Every time I reached the end of the room, I paused briefly, crossed one leg in front of the other, and turned as gracefully as I could. "Well done Jess! You are doing very well. But make sure you keep this up at all times, not just when I ask you to demonstrate. It's no good doing your hair and makeup, and then ruining it by walking around like a moping teenage boy. Remember not to look at your feet, and to keep upright. You know what happens if I catch you out, don't you?" "Yes sir," I said, keen not to earn myself another spanking - or worse."I will concentrate." "Good girl. Keep at it, and very soon it will become second nature. Now, You may continue your homework for the time being, I will check on you again in a while. Oh, and I'm sure I don't need to tell you, but make sure that you clear up after my breakfast. I don't want to see any mess in the kitchen." "Of course, sir." I obediently cleared up after his breakfast, washing the dishes and wiping the table, before returning to my homework. I felt pleased at how the day was going - now that Uncle Roger had agreed not to push me into anything I didn't want to do, I felt I could relax and enjoy spending time as Jessica. I was feeling more happy and confident about my feminine side, and I had to admit that Roger, despite his bullying, had played a big part in that. It's not as if I wanted to be a girl - that thought had never even entered my mind. I was starting to draw a distinct line between my everday life, and the time I spent as Jessica. It was almost as if we were becoming two separate people, with quite different personalities: while Jamie was a grumpy, nerdy, non-conformist teenage boy, Jessica was feminine and compliant. She took pride in her appearance, did her homework, and did what she was told. Almost the antithesis of Jamie. So when Uncle Roger appeared some time later, telling me to finish up my homework and start cleaning the house, I obeyed him without a second thought. I worked methodically, starting in the kitchen, cleaning the floor and the worktops, putting the dishes away, and wiping the fridge. I progressed room by room, vacuuming the carpets, dusting all the surfaces, and making sure everything was tidy. Roger would check on me from time to time, telling me to reach into the corners, or to pay particular attention to certain areas, or simply to say 'good girl', and pat my bottom. "I'm impressed," he said to me as I was cleaning the stairs. "I didn't know you were such a hard worker." "Oh, it's nothing, sir." "Well, it's almost lunchtime. Make us both some sandwiches for lunch, and you can continue cleaning upstairs this afternoon." As instructed, I made some sandwiches and put them out on the table, along with a jug of water with ice and lemon. We sat and ate together, and I made sure that I ate slowly and delicately, instead of scoffing my food as I usually would. We chatted for a while, and Roger made small talk about the school and his teaching days. I sat upright with my legs together, smiling and nodding politely. Roger ate most of the sandwiches himself, only allowing me to eat a little. He explained that men need more calories, and that I needed to watch my figure. After lunch I quickly cleared the table, and continued the cleaning, completing the two bathrooms upstairs - even cleaning the toilets - and making the beds. Having spent a total of five hours cleaning, I felt certain I had finished. "I've finished cleaning the house, sir. Is there anything else you'd like me to do?" "Let me see... have you finished the bathrooms?" "Yes sir, I did both of the bathrooms this afternoon." "And the kitchen?" "Yes sir, the kitchen is also clean." "In that case, I shall have a quick check," he said, as he started walking around the house, inspecting every room. But as soon as he entered the kitchen, I realised that I had not cleaned up after lunch. "Sorry sir," I hastily said, "I forgot about the lunch things. I'll sort it out now." "I expected better from you, young lady. You specifically told me that the kitchen was clean, but there are crumbs all over the place! Plates not washed! It's a disgrace!" "I'm sorry, sir. I cleaned the kitchen before lunch, then forgot to clean up again after we'd eaten." "That's all I hear from you, Jessica - sorry, sorry, sorry. You weren't concentrating on your work, simple as that!" "I'll clean it up, sir. It won't take long." "I don't know... I'm very disappointed. You asked me this morning to go easy on you, and I agreed to cut you some slack, on the condition that you were obedient. But you've not upheld your end of the deal, have you, girl?" "It... it's just a few crumbs and a couple of plates. I can clean it up now," I said, hastily picking up a cloth to wipe away the crumbs. "Stand still, young lady." "Yes sir." "Face the worktop," he ordered, as I obediently moved into position. "Bend over. I know this seems like a minor infringement to you, but I expect complete obedience. If you tell me that you've cleaned the kitchen, then I expect it to be spotless. And I expect you to clean up thoroughly after every meal, without delay. I said bend over. Further." I bent over, with both hands on the worktop. He reached down and put one hand on the back of my knee, rubbing softly with his thumb. He slowly moved his hand up over the back of my thigh, over the tops of my stockings, and onto my bottom. His hand roamed over the silky fabric of my panties. I shivered as he touched me, feeling helpless, vulnerable and humiliated. He slowly lifted up my skirt with his other hand, and he started to spank me. One, two, three, four hard slaps. Another, and another. It started to really sting, and I winced as he continued, finally stopping after ten. "I know you don't like it, Jessie. But you must learn. When you are told to do something, you need to concentrate. Remember when you came here a few weeks ago, and I spanked you for walking like a boy?" "Yes, sir." "And how many times have I caught you walking like a boy since then?" "None, sir. At least, I don't think you have." "Exactly! So you understand that's it for your own good. You need somebody to give you direction now and then." "I... I suppose so." "So you should be thanking me." "If you want to put it that way!" "I wasn't joking," he said in a no-nonsense tone. "Say thank you." "Th... thank you, sir" I replied, barely believing what was coming out of my own mouth. "And what for?" "Thank you sir for giving me direction. Thank you for punishing me." "Good girl. I knew you'd see things my way. Now, clean the kitchen properly, then you can go back up to the spare bedroom and practise your makeup some more. Would you like that, Jessica?" "Yes sir, I would love to." "Good, that's my girl. Take your time, I want to see your favourite, prettiest look." "Yes sir, I will." I couldn't argue with his logic, I had indeed concentrated hard on my walking and movement since that first time he spanked me. But that doesn't mean I agreed with his methods. It wasn't so much the pain that bothered me, it was the complete, total humiliation. I cleaned up the kitchen and went upstairs, sitting down once more at the dressing table in the spare bedroom - my bottom stinging slightly as I sat. I had to admit to myself, it really was a treat to be able to spend time on my makeup, rather than just hurried ten minute practices in the bathroom. I rarely had the time to complete my whole face, but now I could spend as much time as I needed to get it perfect. So this time, I decided to go for a more elaborate, sexy, evening look. First of all, I topped up the foundation I had put on earlier, and then applied two contrasting shades of eyeshadow. I replenished the eyeliner on the bottom of my eyes, and applied liquid eyeliner to the top to create a more dramatic outline. I had only practised this twice before, but held the brush horizontally as I had learned in my book, rested my elbow on the table, and drew dark, well defined lines above my lashes. A bit of mascara finished off my eyes, making the lashes appear longer and thicker. I used a dark red lipstick, and some blusher on each cheek, and the job was complete. I admired myself in the mirror for several minutes, delighted with the results, before walking downstairs to find Roger. As I expected, he was in his study, so I knocked on the door, waiting for permission before entering. "You look stunning, my dear," he said when he saw me. "You really have been practising! You look really beautiful." "Thank you, sir." I still wasn't used to being told I was attractive, pretty, or beautiful. But I felt flattered, and was happy to accept the compliment. "So, I understand it is your seventeenth birthday next week young lady, is that correct?" "Yes sir, that's right." "Well, I have something for you," he said, disappearing momentarily, then reappearing with a handful of bags. "I put together an outfit I thought you'd like - consider it an early birthday present from me. You can go upstairs and try it on now. Take your time... come downstairs and find me when you're ready." "Thank you sir," I replied eagerly. "I will!" "Oh, and there are some bottles of nail varnish too in one of those bags, paint your nails with whichever colour you like." I went back upstairs and rummaged through the bags excitedly, and was absolutely delighted with what I found. In the first bag, there was a matching black thong, bra, and suspender belt, and fishnet stockings. In the second, a beautiful black mini-skirt, comprised of cascading layers of thin black fabric. The next bag contained a black sheer blouse, and another bag had three bottles of nail varnish, just as Roger had said. Then I came to the largest bag - I recognised the logo from a goth shop in town. I opened it, and found a pair of knee-high, lace-up leather boots, with a heel of maybe three inches. And then finally I came across my favourite item; a pair of black gothic elbow length gloves, with a beautiful lace and ribbon detail. Now I realised why Roger had showed me those pictures of girls last week, and asked me to pick my favourite. He was letting me choose my own outfit, which he had now recreated for me. He really had gone to a lot of effort. I took off my clothes as quickly as I could, and folded then neatly on the bed. I was so excited, I must have spent ten minutes just holding and touching the things he had bought for me. I decided to paint my nails before putting on any of the clothes, so as not to stain anything. I had tried painting my nails once or twice before, so had a rough idea what I was doing, but it was a slow process. I picked a dark red shade, and dipping the brush into the bottle, painted each nail, starting at the cuticle and painting outwards. I was so pleased with the way they looked that I decided to do my toe nails too, so I sat on the floor at the repeated the process for each toe. I gave them ten minutes to dry, and then started to get dressed. I started by putting on the thong - I had never worn one before, but I loved the way it looked and felt. Then I put on the bra; it was well padded giving a pleasing shape, with delicate lace around the cups.I fastened it at the back, before pulling the straps over my shoulders and adjusting them to fit. The suspender belt was deep, pulling in my already slim stomach, and the four straps each had a little ribbon over each clip. I gently removed the stockings from the packet, carefully gathering each one up, before slowly rolling them onto each leg, and attaching to the suspender straps. The lingerie really was beautifully feminine and sexy, even more so than the ivory underwear I was wearing previously. I stood in front of the mirror for a while, topping up my lipstick and generally admiring myself. The skirt was also a lovely creation, the multiple tiers of light fabric felt sensual to the touch. It was quite tight, but I managed to fasten it without too much effort. It was also very short, clearly revealing the tops of my stockings, so I adjusted the suspender straps to bring the stockings as high as possible. The blouse was almost transparent, and as I fastened the buttons, I realised that my bra would be clearly visible beneath it. The soft fabric felt great against my skin, and the short sleeves showed off my slim arms. I picked up the boots - despite the laces and the various buckles, they still looked feminine due to the slim fit and the three-inch heel. In fact the boots, together with the stockings and mini skirt, created a very flattering look, making the most of my long, slim legs. The heel was a little higher than the shoes I had previously worn, but after a couple of minutes I was moving around without too much difficulty. Finally, I put on the gloves. They were fingerless - in fact they were completely open ended, so my hand went entirely through the opening, with a small loop to attach to the middle finger. There was a ribbon detail criss-crossing the length of each glove, and both ends were finished in lace trim. They felt incredibly sexy, and looked very elegant, particularly with my red fingernails at the end. I walked downstairs, trying to descend the stairs as gracefully as I could in the boots. Roger must have heard me coming, and came to meet me in the hallway. "You look stunning, Jessie" he told me, as he put an arm around my waist. "Very, very sexy... I could eat you up, I really could! But you're not done yet. I have a few finishing touches that I know you will love." He took me back into his study, and reaching under his desk, brought out yet another plastic bag. He reached inside it, and took out a black corset. He walked behind me, put it around my waist, and wrapping his arms around me, fastened it at the front. It was a half length corset, which came up to just below my chest. He started to pull the laces tight, and I noticed that a well defined waist started to take shape. My small hips looked larger, and the padded cups of the bra became accentuated. Both my movement and my breathing started to become restricted, but didn't care - it looked great. "How does that feel," Roger asked as he started to tie the laces, pulling them tighter still. "Quite tight sir. A little hard to breath, and hard to bend over." "Well, it's supposed to be tight. I'm sure your breathing will be fine after a few minutes. It looks really good on you, it goes well with the outfit, don't you think?" "Oh yes sir, I think it's lovely. And now I realise why you were showing me those photos last week - you were letting me pick an outfit!" "Well, it is your seventeenth birthday in a few days! I wanted to get you something you'd like. Here, I have a few more things for you." He produced a pair of clip-on hoop earrings, a long silver necklace, and two silver rings. He walked behind me again and fastened the necklace around my neck, and clipped the earrings onto my ear lobes. He wasn't sure what fingers the rings would fit on, but after some trial and error, he had put a ring onto one finger from each hand. "I don't know how to thank you, sir. This is the best present I've ever had." "Two more presents still to come, my darling. But first, go into the kitchen and fetch the bottle of champagne from the fridge. Two glasses. I think we should be celebrating." I went into the kitchen and found the bottle of champagne in the fridge, and took out two glasses. How things had changed in just a couple of weeks - when he had first forced me to dress up as a girl, I had found it more embarrassing and awkward than anything else I had ever experienced. But now, here I was, ecstatic with the new clothes he had bought for me, and excitedly fetching a bottle of champagne! Roger poured the champagne, touched his glass against mine, said 'cheers', and we drank. Roger disappeared into his study momentarily, before emerging with two more gifts for me. "Here you are, Jessica" said Roger. He was holding a black leather collar, with a large D shaped ring at the front. "The finishing touch to your outfit. Hold still," he said, fastening it around my neck. "All the goth girls seem to wear them. There you are, perfect." "Thank you, sir" I said, taking another mouthful of champagne. "This is all just... amazing." "OK, the last thing. I hope you like it." He handed me a small box wrapped in pink paper, with a bow tied round it. Inside was a bottle of perfume - I had no idea whether it was expensive or not, but the bottle was very elaborate and pretty. "A girl should always smell good," Roger said. "Try some on." "I'm not really sure how, sir." "Not sure how to put on perfume? Don't be such a silly girl," he scolded gently. "Let me do it". He took the bottle from me, and sprayed a small amount onto my wrists, and a little onto my chest. It smelled enticing and feminine. "Now you smell sexy," he told me, "as well as looking sexy." "Sir, please..." "What, I can't pay a girl a compliment?" "I'm sorry sir, of course you can. I just feel a bit embarrassed when you say things like that." "Well, you do look sexy, and very beautiful." "You've been so generous. I don't know how to thank you." "I'll tell you how you can thank me. You can give me a kiss." "Sir, we talked about this earlier. I don't know..." "Oh come on, just a little kiss. Tell me you didn't enjoy it last time. Tell me you haven't been thinking about it every day. I know I have." "Sir, please, no..." He took the glass from my hand, then grabbed my arms tightly, clamping them to my body, and pushed his mouth to mine. He kissed me harder, pulling me against him so tightly I could hardly move. I melted into his arms, surrendering to his inescapable grip, as our tongues mingled together. His hand moved downwards and he grabbed my bottom. I breathed heavily and nervously as his touch became increasingly intimate, but the tension was suddenly broken when the doorbell rang. "Who's that," I asked nervously. "Dinner! Chinese takeaway. Hope you don't mind, but your cooking isn't up to much, and we need to eat something! Now, go and fix your makeup, then come down and set the table." "Yes sir." "I'm going to have a lot of fun with you tonight, young lady!" he called out as I walked up the stairs. I touched up my foundation and lipstick, put on a bit more perfume, and straightened up my hair. I then headed back downstairs to set the table. Throughout dinner, I continued to drink the champagne - but I noticed that Roger was not really touching his. He told me that he was just making sure that I had enough - after all, we were celebrating my birthday. But I knew that he was trying to get me drunk again, in fact I was already starting to feel rather dizzy. After dinner, I cleared the table and washed up - making sure that I made no mistake this time - and went to join Roger in the lounge. He stood up and took hold of both of my hands. We kissed again, but this time it was more gentle and tender. He held me in his arms, and I realised that it felt natural - put simply, he was the man, I was the girl. "Be my girl, Jessica. Give yourself to me, just for tonight. You don't have to worry, you don't have to think about anything, just be a good girl and do as you are told." "I don't know, sir. We shouldn't." "Just accept what is coming naturally to you. Don't fight it. Accept that you're a sexy, submissive young lady, and hand control over to me." He reached forward and touched the collar around my neck, put a finger through the ring at the front, and pulled me towards him. My actions spoke louder than words, as I let my body go limp with acceptance. He kissed me deeply, holding my collar tight, keeping his mouth locked onto mine. "I'm going to take you out, OK?" "Tonight?" I said, shocked. "But sir, I can't go out like... like this!" "Why on earth not? You don't like the clothes I bought you?" "I love the clothes sir, you know I do. It's just that... somebody might see me." "I should hope so! We don't want to keep you hidden away when you look so stunning." "Remember, Jess - don't worry, don't think about it, just do as you are told. I won't let you come to any harm. I will look after you." I finished the last of the champagne while he grabbed his car keys, he then put an arm round my waist, and ushered me outside. The first thing that struck me was the cool night air around my thighs - the skirt was both short and thin, and was flapping slightly in the breeze. Roger opened the car door for me. The corset made it impossible to bend my back, but I managed to manoeuvre myself into the car, while keeping my knees together - although a flash of the tops of my stockings was inevitable. I did not ask where we were going, but my worst fears were confirmed when I realised we were heading straight into the town centre. I couldn't believe I had got myself into this mess - furthermore, I couldn't believe that I hadn't even tried to get out of it! I tried to do as Roger had told me, and not to think about it - just go along with it. But even so, I was trembling as we pulled up in a town centre car park, terrified of being seen like this. Although I was pleased with the way I looked, anyone who gave me more than a fleeting glance would probably realise that I was a boy. And what if I saw somebody I knew? Would they recognise me? Roger parked the car, opened the door for me, and took my hand. As we started walking, I looked at the ground to ensure I didn't make eye contact with anybody. But, realising that this comprised my deportment, I decided to hold my head high and concentrate on my best 'Jessica' walk, looking straight ahead. Roger held into my hand reassuringly - some people looked at us, but most ignored us. But I still felt incredibly vulnerable, dressed like this, with no money, and no keys; I was totally dependent on Roger to look after me. Then, as we walked round the corner, I realised where he was taking me. "Sir, are we going to The Castle? The Castle Tavern?" "Good guess Jessica, well done!" "But that's... it's... a gay pub." "Yes darling, but don't worry, they are used to girls like you in there. It's a friendly place. Just remember, don't worry, I will look after you." "But I'm too young to go into pubs," I protested. "My darling, with that makeup, you could pass for 22 or 23. Don't worry." It was a busy Saturday night in the pub, the music was loud and men of all ages were enjoying themselves. Men in suits, casual young men in jeans and t-shirts, a couple of muscular guys with shaved heads and tattoos... and even two or three transvestites. That was the first time that I realised what I was becoming... although I was much younger, and - at least in my opinion - more convincing. I was no longer a boy playing with my Mum's underwear drawer, I was a transvestite. Roger bought us some drinks - a beer for him, and sparkling wine for me. I started to feel more relaxed, as I realised that not many people were looking at me. "See, it's not so bad," Roger said, as if he could read my mind. "Nobody is staring at us. And if anyone does look at you, it's probably because they fancy you! But you're with me. You're my girl tonight, so nobody will try to chat you up. I'll make sure you're OK." "Thank you, sir" I replied, sipping my wine, feeling increasingly intoxicated. "How does it feel, knowing that some of the men in here are checking you out? Looking at you, dressed like that, with your miniskirt and see- through top?" "It feels strange, sir." "I bet it does, Jess. But I must admit, I like the thought of other men looking at you and lusting after you... because they can't have you. But I can. And I will." He leaned forward and kissed me. When we walked back to the car an hour later, I was very tipsy, but altogether more relaxed about being seen in public. I walked confidently with my head held high, Roger's arm around my waist. **** "Fetch me a whisky," Roger said when we arrived home. "With ice and a drop of water." I made his drink, and brought it to him in the lounge. "Good," he said, tasting the whisky. "Good girl. Sit down, I want you to try something." "What's that," I asked, as I saw him pick up a small glass bottle and some cotton wool. "Have you heard of poppers, Jessica? Nothing to worry about, it will make you feel relaxed and sexy. I'm sure you'll love it." I had never heard of poppers, but I sat on the sofa, as he poured some fluid from the bottle onto a wad of cotton wool. He put one hand behind my head, pushed the cotton wool against my nose, and told me to sniff. My nose filled with the burning, acidic vapours, and I tried to pull away, but Roger held my head tight. I caught my breath, but he immediately poured more onto the cotton wool and held it against my nose again. This time I managed to fully inhale, and I immediately felt relaxed and light-headed. In fact, I felt as if I was floating away, and when Roger kissed me again, it felt almost like an out-of-body experience. "Now, stand up," he told me. "Get onto that stool, girl." He pointed to a large upholstered foot stool, with four short wooden legs. "Lie on your front. With yours knees on the floor and your arms in front of you." I silently did as I was told, as he took two leather belts, and used them to tie both of my wrists to the legs of the stool. He took a piece of cloth and tied it over my eyes, so I was completely blindfolded. I heard him walk up the stairs, and he was gone for two or three minutes, leaving me helpless, desperately wondering what he was going to do to me. I was scared and nervous - had I done something wrong? Was he going to punish me? I heard him walk back downstairs and into the lounge, and I felt him behind me, his hands on my body. He lifted my skirt, and my whole body jerked forward as I felt his hand reach under my thong. I heard the clicking sound of a plastic bottle or tube opening. He pulled the thong to one side, and suddenly there was a cold, wet sensation sending another shock through my body. I felt an object being pushed into me... a strange alien feeling, penetrating and stretching me. Roger comforted me, stroking my hair and telling me not to worry. He then told me to open my mouth, and proceeded to put something inside - longer and fatter than the first object, made of a type of plastic or rubber. He asked if I could still breathe - I nodded. "Do you like that, Jessica? Do you like having a dildo in your mouth? You look so sexy, bound and helpless, with a dildo in your mouth and a butt plug in your hole." He moved behind me, and put his hand inside the front of my panties, and grabbed my penis, rubbing it for a few seconds. He then left the room again, I don't know how long for; five, maybe ten minutes. When he returned, he removed the dildo from my mouth, and then slowly took out the butt plug. The sensation was unbelievable as it slid out - a wave of pleasure passed through my body, and I let out a sigh of ecstasy. I felt more cold, slimy liquid. And then something else being pushed into me... I realised it must be the dildo which had been in my mouth. He pushed hard, pulling my buttocks to the side, as I moaned at the dull pain. There was a brief pause, and then the cotton wool soaked with poppers was pushed under my nose again. I inhaled deeply, and the floating sensation returned as the my whole body relaxed. Pain blended with pleasure, and I started to accept the dildo, feeling it pushing further and further into me. He started to slowly slide it in and out, fucking my hole with the dildo. After several minutes, he took off my blindfold, and crouched in front of me, kissing me once more, tenderly touching my face. He gradually released my wrists from their bindings, and helped to my feet. "Good girl Jess, well done. Come on, we're going to bed." He held my hand and led me upstairs, turning off the light as we went. I stood in the bedroom, as still as a statue, as he removed my corset - loosening the laces at the back, and then unfastening the front. He unzipped my skirt, letting it fall to my feet, and slowly unbuttoned my blouse. He pushed me down gently onto the bed, and slowly removed my boots one at a time, stroking his hands along my legs and ankles. I now was wearing just my underwear, stockings, and the long black gloves. I sat nervously, silently, as he took off his own clothes. I was terrified - but I realised that I wanted this to happen. I wanted to feel what it was like to be a girl, and to be fucked like a girl. I wanted to wake up as Jessica, in this beautiful, sexy lingerie. I reclined, and Roger got onto the bed beside me. He grabbed the ring of my collar just as he had earlier, pulling me towards his naked body, and kissed me deeply, almost aggressively, as his tongue mercilessly invaded my mouth. We embraced, and he rolled on top of me, putting his full weight on me so I was helplessly trapped beneath him. I felt his cock pressing against my panties, I could feel how hard he was, and I knew what was coming next. He reached for his bedside draw, and took out a condom and some lubricant. "You do it, Jessica" he told me. "Put the condom onto my cock." "Yes sir," I replied. Although I had never done this before, I obediently removed it from the foil packet, and unrolled it over his hard, manly shaft. He told me to get on all fours. Again, I was unquestioning in my obedience, and moved into place. He grabbed my legs, pulling them apart, and positioned himself, kneeling behind me. He put his hands on my hips and slowly entered me. He was being quite gentle, but I nevertheless whimpered at the pain. "Relax, Jess. Just accept it. Be a good girl. Don't force me to gag your pretty little mouth." "Yes sir, I will try," I gasped, as he pushed further inside me. It felt as though I was watching this happening to somebody else. It was too surreal... was this really happening? Could I really be having sex with Uncle Roger? He started to thrust back and forth, and my cries of pain turned to small, high-pitched cries of pleasure with every pump. His grip on my hips tightened, and I started moving my body towards him, matching his rhythm, until he tensed up and came to a shuddering climax. We hardly slept that night, it seemed as though whenever I closed my eyes, he would grab me by the collar and push his tongue into my mouth, and our bodies would intertwine. When he ordered me to suck his cock, I slid under the covers with an obedient 'yes sir', and took his penis into my mouth, licking, sucking, and rubbing for all I was worth. When morning broke, he told me to fix my makeup, and bring him breakfast in bed. After he finished eating, I gave him another blowjob, and then we lay together in a lazy embrace. I couldn't believe what we had just done, but it felt good. Lying there in his arms, I had never felt so feminine, and so fulfilled. "Oh Jess," he said after a long silence. "My dear, sweet Jessica. You know, I can't force you to keep coming to see me. Your mother won't be angry with you forever, she'll have to start trusting you alone in the house some time. But I want to keep seeing you. You've done so well, in just a couple of weeks you've become an attractive, sexy, obedient young lady, and I know I'll never find anyone else like you. Keep coming to see me, and you will have beautiful, sexy clothes and lingerie. Jewellery, perfume, and all the makeup you want. Chocolates and flowers. Night clubs, restaurants, and champagne. Next year, you will be eighteen, and before you know it you'll be leaving home to go to college. We can have weekends away, stay in romantic hotels with four poster beds, and nobody will know. In return... you will continue to be my obedient, compliant, sexy young girl. You will do as you are told, without question, both in and out of the bedroom. You will work at making Jessica even more sexy and feminine. You will accept the appropriate punishment when you misbehave. You will be subservient to me, and continue to call me 'sir' at all times - it wouldn't work otherwise. I will look after you, guide you, and train you to be my perfect girl." "I... I don't know what to say, sir. It's a very tempting offer, and I know you've done a lot to bring out this side of me." "Look, this won't last forever. I'm a lot older than you, and you have your whole life ahead of you. But neither of us will have this opportunity again. You'll still have plenty of freedom to do what you want in your everyday life as Jamie, even date girls if you like. But Jessica... Jessica will belong to me." "Let me think about it, sir. I love dressing up like this, and I love being Jessica. But this would be a very big commitment." "Please do think about it. I know I will be thinking of little else. Now, you'd better get changed. your parents will be here soon." "Yes sir."