Carol's Diary free porn video

Carol's Diary Or "The Transformation" By Carol Holloway Friday, March 26th 1993 Before I start this story, I'd better tell you a few things about myself. I've been a transvestite, or crossdresser if you prefer, for about sixteen years now and it has always been my fantasy to live life as a woman for a short period - a few weeks or maybe a month - just to see if I could carry it off. I never thought I'd have the chance or the courage to do it, but recently, I was granted a golden opportunity to give it a try. After I had placed a small ad in 'Loot' I had been lucky enough to hear from a woman who was sympathetic and she had offered to put me up in the spare room at her house in London after meeting me a few weeks ago for a quick drink and a chat. Anne is 27, has a slim rounded figure and a lovely mane of long red hair. She loves life, lives for clothes and sex and is very liberal in her views. As Carol, the only real difference between us is that my hair is black - and I'm a man of course. It was obvious that this was a relationship made in heaven. I arrived at Anne's home in Ilford early this morning carrying a giant suitcase packed full of all my favourite women's clothes, underwear and make-up - in fact, the only male clothes I had with me were the ones I was standing up in - that was one of Anne's conditions. As I struggled through the door she took one look at me in my jeans and T- shirt, smiled and shook her head in admonishment. "Nice to see you," she greeted, "but I'd like you to get changed out of those boring old men's clothes as quickly as possible. I've already told all the neighbours that my cousin, Carol, from Surrey is going to be staying for a few weeks, so all the time you're here I want to see you dressed as a woman. They might start asking awkward questions if they see a strange man hanging around." Well, that suited me - after all, being Carol for twenty- four hours a day was just what I had come here for. "I'm going out to the shops, so make yourself at home," she added. "I'll be back in a couple of hours and if you're ready by the time I get back I may have a surprise for you." Indicating the stairway, she added, "The bedroom at the top of the stairs on the left is yours." With that promising statement she left, leaving me breathless and eagerly anticipating my weeks as Carol. I made my way upstairs and found myself in a reasonably large bedroom, complete with double bed, bedside table and dresser. One entire wall was occupied by a sliding mirrored door wardrobe. I slung my heavy suitcase down on the bed, opened it and started to unpack. I carefully put all my dresses neatly on hangers in the wardrobe, put my underwear away in the drawers and lay my cosmetics and brushes out neatly on the dressing table. Before I went any further, I got undressed and took a long hot bath. I'd already taken the step of removing all my body hair the day before as I thought it would save some time. I'd used a good strong depilatory cream on my body and wax on my face, so I was still hairless and very smooth and probably would be for some time. For an extra feminine touch, I used some Body Shop scented foam bath oil and washed my long dark hair in apple shampoo and conditioner. I lingered in the bath a long time, as I was still quite nervous. After about three quarters of an hour I plucked up the courage to get out and dry myself off, deciding as I wrapped a towel around my wet hair that it was time for my transformation into Carol to begin at last. I desperately wanted to get into the type of clothes I felt most comfortable wearing as quickly as possible but as I'd never appeared dressed as a woman in front of anyone else before, let alone a complete stranger, I had slightly mixed feelings. How would Anne think I looked and more importantly, how would I compare to the real thing? The transformation started by spraying myself all over with some musk scented Impulse Body Spray and putting on a pair of nine denier Pretty Polly 'nearly black' stockings and a Gossard lacy black suspender belt with bra and knickers to match. I always get a feeling of sheer femininity when I roll the stockings on over my smooth legs and I like to savour this part for a few minutes in front of the mirror once I've slipped on a pair of black high heels. I should really take a size seven, but I always manage to squeeze into a size six to help make my feet look a little more feminine. As it was still quite early in the day, I decided that the 'career girl' look would be the most appropriate and the least conspicuous. I've got a plum coloured pencil skirt and a black jacket from Next that always sets my pulse racing, so I popped in my boobs, pulled on a black slip, buttoned up a heart neckline collarless pink blouse and put them on, finishing off the outfit with a tidy black leather belt. My boobs are the type that pre-op transsexuals use - they cost me a fortune, but they're worth it as they look and feel so realistic. As I also have a pair of plum coloured shoes that match the skirt and blouse I had decided to wear, I decided to swap them with the black ones for the sake of colour co-ordination. As I steadied myself on the dressing table with my hand and bent my leg backwards at the knee to swap a shoe, I glanced in the mirror and noticed that I was striking a very feminine pose. I continued facing the mirror and smoothed the lines of my skirt and jacket - so far so good. Next, I took off the jacket and sat down at the dressing table to put my make-up on. I applied a light layer of cream, blotted it and allowed a few minutes for it to dry. I wanted to get this right, so I was taking extra care. I followed this with some eye shadow. I used my favourite shades of plum again and blended them in as well as I could. Then, I applied two coats of black mascara, lengthening my upper lashes and slightly darkening my lower. I sucked in my cheeks and applied the blusher that gave my face that warm look and finally, the most sensuous part of all, a deep plum lipstick. I applied two coats, blotting each on a tissue and added a coat of 'lip-seal' to stop it running before moving on to the final steps of hair and jewellery. I blow dried, brushed and sprayed my hair into a straight but feminine style and quickly popped a pair of large gold hooped earrings while admiring the result in the full length wardrobe mirror. Stunning, I don't think I had ever looked that good before! Posing with my hands on my hips, I realised that I hadn't painted my nails yet so I used a varnish that was the same plum colour as my lips and sat for what seemed like ages while waiting for them to dry. I'd let them grow for about a month in anticipation of this day and I'd spent an hour the day before manicuring them so they were quite long and pretty. I applied a coat of nail strengthener and two coats of varnish. When both had dried I decided that as this was a special occasion I would treat myself to a light spray of Chanel perfume. Finally, a ring bracelet, a delicate gold neck chain with my chosen name, Carol, on it, a few rings on my fingers and a long appreciative glance at the final result. I looked amazing. As I made a few minute adjustments to my hairstyle with my fingertips I began to appreciate why I had let my hair grow - the real thing was so much better than the wigs I used to use in the early days when I could only change into Carol during the evening or at weekends. I hoped that Anne would agree to style my hair for me with her curling tongs when she returned. Although it looked quite feminine it was a little straight and needed something to break up the lines. I walked to the lounge, poured myself a drink of gin and tonic - heavy on the gin, nerves again unfortunately - and sat reading some of Anne's magazines until she returned. At long last I heard the front door open and in stepped Anne carrying a few bags of shopping. I rushed over, hardly able to contain my excitement. "Well, what do you think," I asked coyly as I stood posing in the hallway. "You look pretty good," she said, checking me up and down, "but there is one thing that could be better. Your hair needs styling. Come on, I've booked an appointment at the best hairdressers in town for a perm." Seeing my horrified look, she added, "You are serious about this aren't you?" I nodded, but inside I was still a little unsure even though she seemed to have read my mind and focused on the one thing that I was still unsatisfied with. "Of course," I said, trying to sound more decisive than I actually felt. "I'll just get my handbag." I quickly popped upstairs, grabbed my handbag and packed a few cosmetics and some money. I looped the bag over my shoulder, grabbed a thigh length black overcoat and nervously descended the stairs to rejoin Anne who was waiting by the front door. Suddenly, just as I slipped the coat over my shoulders, a wave of panic hit me. "Wait," I said holding up a trembling hand, "I think I need a cigarette before I go. I've got a bad case of the butterflies." I reached into my bag and pulled out a packet of JPS, offering one to Anne, who smiled and produced a lighter. She lit hers first and then offered me a light as my hands were shaking too much. I placed the cigarette between my lips and as I bent over and pointed the end of the cigarette into the flame, I caught my reflection in Anne's hallway mirror out of the corner of my eye. It felt as if I were a third person standing and watching from somewhere else in the hall. I appeared to be watching a beautiful woman inhaling deeply as her cigarette was lit, a look of calm and relief taking over her face as she took the smoke gratefully into her lungs. I continued to watch this woman as she took the cigarette from between her lips and exhaled a long stream of smoke upwards toward the ceiling, her every movement strangely mimicking mine. All at once, the reality sunk in. The woman in the mirror was me. I'd only ever dressed like this alone before, but standing next to Anne was putting a whole new and delightful perspective on things. Even though my nerves weren't totally under control this gave me the boost I needed so I decided that it was now or never. Opening the front door I took my first tentative step out into this strange new world - then another and another, each step becoming harder than the last and each echoing click of my heels on the ground reminding me of exactly what I was daring to do. Anne followed, locking the door behind her and placing the keys in her handbag which she snapped shut with a loud and unsettling click. Seeing the determined and knowing smile on her lips I realised that there was no arguing or turning back now - here I was, standing in broad daylight, dressed from top to bottom as a woman, answering to the name of Carol and about to go into a strange town busy with Friday afternoon shoppers - when all I had ever done before was venture out at about one o'clock in the morning for a quick panic filled walk around the block. "Come on, Carol," she said, smiling wickedly at my very obvious discomfort. "We don't want to be late, and don't think I'm letting you go back inside either. You can stand outside all day if you really want to but it's a bit cold and the neighbours might get curious, so I think you'd be better off coming with me." With that she brushed past me and set off down the garden path, her bottom swaying and her heels clicking on the ground. I followed her, doing the same. I had long ago discovered that a great many things about the sexy way a woman moves are down to her clothes. The pencil style of the skirt I had chosen forced my legs to take small and precise steps one in front of the other and that made my hips sway and bum wiggle provocatively - try it and you'll find you can't help it. The high heels encouraged me to place the flat of my sole down before the heel which I still couldn't stop from clicking when it struck the hard ground - all this tends to make me push my buttocks together and helped me stand straight and elegant. It also stopped me from walking too fast which added to that elegance. As Anne had mentioned, it was a bit cold and there was a slight breeze. As I walked, I could feel its chill on my nylon clad legs and up around my crotch. That 'open air' feeling is one of the best a transvestite can have. We made our way to Anne's car and she opened the passenger door for me. I remembered to keep my legs together as I sat down in the seat and brought them round into the car. That was one rule of feminine deportment that I did know. Anne started the engine and began heading towards town. We hadn't gone very far, no more than about a quarter of a mile, when Anne pulled over and parked. "What's up," I asked? "Didn't you say that we had a hairdresser's appointment? I don't want to be late." The idea of having my hair femininely styled by an expert was beginning to appeal now that I was in the safety of the car. "Don't worry, we won't be late," said Anne "but I'm out of cigarettes and I noticed that you're down to your last few. There's a newsagent just over there." She finished parking the car, reached into her handbag and brought out a ten pound note. "Twenty JPS, get some for yourself and pick up a few magazines while you're there." Seeing my shocked face, she added, "Look, you're going to have to face people sooner or later unless you're planning to spend the next two weeks locked and hidden away in your bedroom like Rapunzel or something. Why not make a start now." This made sense but it was only later that I began to wonder why Anne hadn't bought her cigarettes when she was out shopping in the morning as at that moment I was feeling too frightened to think clearly. If I could have, I might have realised that this was all part of a plan but I'll save that part for later as I don't want to get ahead of my story. I climbed out of the car and started walking towards the Martins newsagent, my heels clicking very conspicuously on the pavement and seeming to echo clear across town. I was sure that everyone in the street was staring at me as I walked from the car and I prayed that it was just nerves again. I pushed open the door and entered. There was a queue of about four people, so I busied myself in the magazines for a few minutes until they left, selecting the latest Cosmopolitan, New Woman - how appropriate that title was - and Woman's Own, the latter of which had a free lipstick that I could add to my collection. When the queue had died down I cleared my throat, walked up to the counter and asked the young girl for forty JPS as femininely as I could. Without a second glance, she took the cigarettes from the display behind her and rang them up on the till. "That will be four pounds and twelve pence please." "Oh, don't forget the magazines", I said, with a bit more confidence this time as I indicated the pile I had placed on the counter. "Oh, yes. I'm sorry Miss." She entered the price of each magazine. "That'll be eight pounds and seventeen pence please." I handed over the ten pound note and opened my handbag. As I put the cigarettes and change away I couldn't help feeling a comforting thrill as I saw all my make-up sitting there - the make-up that I was wearing on my eyes, cheeks and lips right at that moment. I had also decided to keep a few tampons in my handbag at all times. Obviously I don't need them but I thought their absence might seem a little odd if anyone got to thinking about it. Feeling extremely feminine I snapped the bag shut, thanked the girl and went to leave the shop. When I got to the door, a man who had just walked in held it open for me and I thanked him. I could barely stop myself from breaking into a run as I went back to the car. I couldn't wait to tell Anne about my first success. I felt like a million dollars. "See," she said tearing the wrapper off her cigarettes and offering me one. "All you need is a bit of confidence. A great pair of legs help too and it looks like you've got both." We lit our cigarettes and Anne drove off. "Now for the final part of your transformation," she said, smiling. When we arrived at the salon, I strolled in behind Anne confidently and a nice young man offered to take my coat and hang it up. Suddenly, a voice said "Miss Holloway?" I turned round and saw that the voice belonged to a pretty young blonde who was presumably the hairdresser. It took a few seconds before I realised that it was me she was addressing. "Y-Y-Yes," I said timidly. "My name's Julie and I'm your stylist. Please sit down and I'll be with you soon. Would you like coffee?" she asked smiling. I nodded and sat down. After a few minutes Julie returned with a cup of coffee. "Okay, Miss Holloway," she said, fluffing my hair up with her fingers. "What would you like me to do?" I had just opened my mouth to reply when Anne stepped in and answered for me. "Carol's looking for something totally different but she hasn't quite had the courage to go for it yet. She really wants a loose blonde perm because her last boyfriend wouldn't allow her to have one." My heart nearly stopped - I wasn't expecting this - but it was too late to get cold feet now. "Oh, I see," said Julie, laughing and brushing back her blonde locks. "Afraid you'd get too much attention from other men, was he? Sounds like you're well rid of him! Well, golden blonde it is. How about a few highlights as well? You'll be fighting the fellas off then." "Yes, why not?" I said. "Golden blonde with highlights." I could scarcely believe my nerve but there was no going back now. Anne said that she was popping out for an hour or so leaving me to my fate. A little while later I was sitting in the chair looking at myself in the mirror, my hair covered in foil. I couldn't see what the end result would be from this mess so to take my mind off it I leafed through some magazines paying extra attention to the make-up and fashion pages. There were so many different styles that I wanted to try. Before I knew it, an hour and a half had passed and I found myself sitting back in the chair checking the result as Julie held up the mirror and made a few minor adjustments as she did so. I was amazed when I saw the beautiful but unknown woman who was staring back at me. I looked lovely, sexy, stunning and all importantly, I looked like a completely new woman! Julie had done a fantastic job. My hair had been permed, but not tightly, so it hung loose and curly midway between my shoulders and the small of my back, the new golden colour contrasting beautifully with my blusher and lipstick. It was held behind my ears by two clips, which showed my earrings off beautifully, and she'd added a small black bow at the back. The colour was an amazing golden blonde with lighter streaks running the length of it. I looked perfect and told her so. When I paid, I thanked Julie and gave her a handsome tip. By this time Anne had returned and she was as impressed as I was. As I left the salon and we walked back to Anne's car, I could feel the men in the street staring at me, in particular, at my legs. "Why not," said Anne. "You look amazing and your legs are very feminine. I'll bet they're all thinking 'does she give blowjobs?' Trust me, I know how men think - they can't wait to get their cocks into a woman's mouth, especially a blonde." She must have seen the excited look on my face because she added knowingly and under her breath, "and you'll find out all about that part of things very soon I'd imagine." As we walked back to the car, I wondered what she meant by this second cryptic statement of the morning. Before we returned to the house, Anne suggested stopping off at the shopping centre. I was now totally confidant as Carol and wanted to buy a few new dresses, some more underwear and some different make-up to go with my new blonde hairstyle so I readily agreed. I felt wonderful walking around the centre amongst all the shoppers, none of whom gave a second thought to my sex, except for the men who obviously thought about it a lot, thankfully for the right reasons. A couple of workmen who were busy redecorating a shop front whistled as we walked past. Anne blew them a kiss and we wiggled away, giggling like schoolgirls. I was especially pleased with a dangerously seductive little black pencil skirt dress with a heart shaped neckline that I'd just bought at the Miss Selfridges sale for thirty pounds because I was certain I'd look amazing in it. I'd also bought a new cream and brown woollen skirt and jacket and three white blouses. I'd tried them all on, feeling very naughty for using the ladies' changing room but nobody seemed to notice anything out of the ordinary. My new blonde hair suited these lighter colours and I suspected that I'd soon find a good use for a smart suit. The best part of the afternoon was a visit to Saxone where I must have tried on a dozen pairs of shoes before making my final choices. With each pair I tried, I stood up and walked to the full-length mirror and admired the way they looked with my legs and eventually choosing a pair of black and a pair of creamy white stilettos. I must admit - I'm a bit like Imelda Marcos when it comes to shoes. Finally, we popped into Marks and Spencer and I had a thrilling time choosing underwear. It made a change from being stared at while buying my undies as used to happen when I shopped before. A man buying lingerie attracts a lot of unwanted attention, but a beautiful blonde woman buying some sexy undies looks and feels totally natural. I could take my time and choose exactly what I wanted. Anne had said that a woman feels sexy when her lingerie is sexy and this seemed like good advice. I bought several complete sets of underwear in black, white and pink, as well as various shades of stockings to go with them, a few slips and teddies and a new outdoor coat. I must have spent about five hundred pounds in total on new clothes and make-up but I could afford it and I had a feeling that I was going to need them. When we returned to the flat, I got the shock of my life and nearly dropped all my shopping. There were two strange men sitting in the armchairs waiting for us. "Hi, Tony. Hello, Alan," said Anne, smiling. "I'd like you to meet Carol, my cousin from Surrey. She's staying with me for a few weeks." The two men laughed and said hello in a friendly sort of way, but never took their eyes off my legs as they did so. Anne was right. They were wondering if I gave blowjobs! Standing there in a skirt and blouse, stockings, suspenders and bra, make-up, my new hair style and looking at these two expectant horny men, I made the decision that I did give blowjobs and I'd be giving these two men a bloody good blowjob very soon. Well, why not, I thought. The idea of sucking a man's cock while dressed as a woman had always turned me on and I was never going to get a better chance than this. "I'm just going to try my new dress on," I said, as femininely as possible. "I'll see you men soon." I emphasised the word 'men'. I beat a hasty retreat upstairs to the bedroom and stripped off, giving my hair a quick brush as I did so. I changed from my black undies into a white bra and suspenders and a very sheer pair of matching stockings. I decided that a pair of white stilettos would look most appropriate for this occasion - either my brief stay in Ilford had already turned me into an Essex girl or perhaps I just liked the idea of dressing in virgin white for my first sexual encounter with a man. I went to the wardrobe and took out an old favourite - a little white shift dress with a 'v' back and front - and tried it on. It was a tight fit, but worth the struggle. After all, I was a woman, I was determined to give both those guys the blowjobs of their lives, so I was going to make damn sure that I looked as sexy as I could for them. I freshened my make up with a new coat of lipstick and changed my eye shadow to some new shades of gold and brown to match my hair and returned to the lounge. One of the guys whistled when I walked in and sat down. I crossed my legs seductively and put a cigarette between my lips which one of the men immediately lit for me. I blew out a long stream of smoke, smiled and made some small talk while I waited. I was very much enjoying the fact that I was the centre of attention. I didn't have to wait very long either I'm glad to say otherwise I think my nerves would have given out. Anne had obviously planned all this right from the start and was making sure that I went from one experience to the next without time to think about the consequences. "Okay, Carol. I know what you're thinking and you're right," said Anne. "I gave Tony and Alan a spare key last night and suggested they come round to meet you. I've told them that you want to learn how to suck cock, and they're willing to give you as much instruction as you need. I suggest you try Alan first. He's a bit easier if you've never done it before, but remember this - you are going to suck both these men off before they leave." As I smoked my cigarette and sipped a gin and tonic that Anne had prepared for me while I was getting changed, Alan stood in the centre of the room and took off his clothes. He had a good physique and a lovely bum, but his cock was just mind-blowing and I just couldn't take my eyes off it. It was eight inches long at least and it terminated with a lovely shiny purple head looking like it would burst if it wasn't sucked soon and mesmerising me like a cobra mesmerises its prey. Fortunately, despite its length it was on the slim side and I noticed that its owner, Alan, was looking at me very expectantly, smiling as I let out a little involuntary gasp of awe at his shaft. I took one last drag from my cigarette, stubbed it out into the ashtray and walked towards my first moment of true womanhood. He was already fully erect - the way I looked in this dress you wouldn't expect anything else - so I just walked right up to him, got down on my knees, closed my eyes and took that lovely knob into my mouth, caressing it gently but firmly with my tongue and masturbating the rest of its considerable length. As Alan began moaning, I heard Anne remark that it didn't look as if 'the little tart' needed teaching very much at all. This compliment only spurred me on so I decided to step up the action immediately. I slid my lips, which I kept tight over his cock, down about half way and back again, running my tongue firmly all around his knob when I reached the end and allowing it the occasional lingering brush against the roof of my mouth. Who's a big boy, I couldn't help thinking as I felt his cock touch the back of my throat before even a single stray pubic hair could brush against my lips - a good four inches remained. I continued doing this for about five minutes while massaging his balls and stealing the occasional glance at my lover's ecstatic face. It was quite obvious that he was enjoying my mouth on him and I was enjoying it so much that I was only vaguely aware that Anne was urging me on, and that the other guy, Tony, had a video camera and was taping the whole affair. I'd managed to turn from an ordinary transvestite to a porn star all in the space of half a day. Well, as I was going to be on screen then I'd better put on a performance worth watching. Remembering all the videos of blowjobs that I had seen and plucking up all the courage I had, I pushed hard on his cock and swallowed. About six inches of it disappeared into my mouth just as Tony was taking a close up shot of my head. A few more attempts and I had the lot, the curls of my new blonde hair buried in his groin and his balls pressed up tight against my imprisoning red lips! "You're doing very well, Carol," said Anne, "and I'd say from the sound of things it won't take much more of that before Alan comes. When he does, I want you to remember this. It's going to be in your mouth, you're going to swallow every drop of his sperm and you're going to lick his cock clean afterwards. I don't want to see you pulling away or spitting it out or our agreement is off and you can leave tonight. When a woman learns to suck cock in this house, she damn well learns to suck it properly." The way I was feeling, I wouldn't have had it any other way. Besides, I was eager to get to Tony's dick, little tart that I was, so Anne's words just made me suck harder and faster. When Alan's hands suddenly gripped my shoulders I gripped his cock tightly and braced myself - this was it! He groaned twice and shot a hot stream of sperm into my mouth, followed by several smaller ones in such quick succession that I could hardly swallow the first before the next arrived. It was gorgeous! I'd never tasted anything like it so I kept swallowing and made sure that I didn't miss a drop just as Anne had instructed. After I had licked his cock clean and placed a gentle and grateful kiss on the tip, I looked up to find Anne operating the camera and Tony removing his boxer shorts. Good God, this was going to be difficult! Tony held what looked like ten inches in his hands (ten and a half as I discovered later) and it was thicker than Alan's. Anne caught the shocked look on my face. "Same rules apply, you little whore. I'm sure you'll manage. You seem to have managed well enough so far," she commanded heartlessly but with a smile. "Well, I'll need a rest before I start sucking that monster," I said, still enjoying the taste Alan's sperm on my lips and in my mouth. Anne agreed, switched off the camera and freshened our drinks while I lit a much needed cigarette. As I smoked and fondled Tony's cock, Anne poured me another drink and got down on her knees to suck Alan hard again, swallowing his entire length with an ease born of long experience. I could see that I had a lot to learn from this woman. Before too long, I was on my hands and knees again, sucking Tony for all I was worth. I couldn't take everything he had, but by Christ, I was going to give it my best shot. I twisted my head trying all angles to make it easier to swallow and eventually succeeded in taking eight thick inches. I couldn't manage the rest as hard as I was trying - the thickness as just too much for my untrained mouth. All of a sudden, I felt Anne's hand tugging on my shoulder. I pulled my mouth from around the cock I was sucking and looked up. "Perhaps you need some help. Eight inches is pretty good for a beginner, but we're not going to quit there. I've got a reputation to live up to you know." She knelt down and gripping the base of Tony's shaft tightly in her hand she began to instruct me. "First, make sure your mouth really wet. It'll help lubricate your throat. Then make sure his cock is straight and align your throat with it, relax. Open wide and just take it all in." And she did, effortlessly. After a few slow and teasing strokes with her mouth, hardening him even more, she released him. "Now you try," she added, "but first take that dress off. You'll feel sexier in just your underwear." I did as I was instructed, revealing the virgin whites of my undies as seductively as possible, trying to look coy as I was being followed by the close eye of the video camera and tried to put Anne's advice into practice, but it was still impossible even though I was now fairly drunk. No matter how hard I tried, those last few inches were completely beyond me. "Perhaps you need a little encouragement," Anne said firmly. With that, she picked up a cane and before I could protest, she moved behind me and struck it swiftly across my bottom. My flimsy knickers did nothing to take the sting out of the blow and despite the size of the cock in my mouth; I opened it wider in shock and surprise. As soon as I did, she administered another and much harder stinging blow. Instinctively I moved forward to try and get out of the way but of course I only succeeded in pushing down harder on the cock that was invading my mouth. After ten more encouraging blows which brought tears to my eyes, to my shock, I managed another inch. That still wasn't enough for Anne who just kept the cane coming down harder and faster. Eventually, in a desperate attempt to stop any more blows from landing I swallowed as hard as I could and found my lips up tight against Tony's heavy balls. I gripped his buttocks and started sliding up and down his delicious penis in raptures of joy, the accompaniment of the cane and my stinging bottom making me feel every bit the submissive woman that I had willingly become. After a few extra strokes from the cane - just to keep me eager and compliant, Anne had explained - I felt my knickers being removed and before I could complain, which wouldn't have been easy with my mouth full as full as it was, I was being fucked from behind by Alan. So what? I was a woman now and Anne and these two guys had every right to expect me to behave accordingly. Crouched on all fours in make-up, suspenders and bra and allowing two men to satisfy themselves as they chose with my body I felt the most delicious slut imaginable and vowed that I'd have more of this in the weeks to come. When both Alan and Tony had come they swapped ends and resumed fucking me just as hard as before. Before the afternoon was over, I had become a woman in the best sense of the word, five times over. Three times at the front and twice behind. However, there was more to come. Just after Alan had shot his load for the second time into my eager mouth, Anne returned to the lounge. She'd changed out of her clothes and was now stark naked except for a pair of black thigh boots. In her hand she carried a riding crop. "Well done, Carol. I think you've got these two studs nicely warmed up but I think it's time I took a turn with them now." She walked over to where I was kneeling on the floor and continued, "I don't like to waste my time with flaccid cocks. Get them hard again for me, you little slag," she commanded, tilting my head up with the tip of the crop. Well, frankly I couldn't believe there was a drop of spunk left in these two guys but faced with the riding crop I wasn't about to argue so I began to lick Tony's dick. Within a few seconds I was proved wrong as his organ swelled to fill my mouth again. Once he was at full length I reluctantly released him from my mouth and led him by his cock, still on my knees, to where Anne was down on all fours and guided him into her vagina. Anne accepted his cock with ease and as he began fucking her I set to work on Alan, a job I was looking forward to - he did have such a lovely cock. Eventually, after about five teasing minutes, when he began to swell, Anne gave me further instruction. "When he's ready for my mouth I want you to go and lie on the sofa and masturbate. Wank as hard as you like but don't come until Alan, Tony and myself have - you won't believe the thrashing I'll give you if you disobey me." "I obey, Mistress," I said demurely, my head cast down to the floor. God, how easily I had slipped into the role of slave. When he was ready I led Alan to Anne's lips and went to lie on the sofa to do as commanded, wishing it was going to be me finishing the job. I lay down and began wanking, already too close to orgasm for comfort. When, after half an hour of stern fucking, Tony and Alan had both relieved themselves inside Anne's fortunate body and I could hold on no longer, I cried out and shot sperm halfway across the room, collapsing in an exhausted heap as I did so. When Alan and Tony finally left at about eight they both offered to give me further lessons whenever I felt ready. Personally, I felt exhausted, sore and drunk. I slumped in the armchair while Anne cooked us a late dinner. As we ate, we watched the video we had shot that afternoon. It was a funny feeling watching myself being fucked but I didn't look too bad at all. The best part was the look of shock on my face when Anne had started caning me as it was replaced by one of sheer panic as I desperately tried to swallow the rest of Tony's cock and prevent another blow landing. Anne agreed that I gave good blowjobs and offered me some advice about how to make it last until a man is begging to be allowed to come. She added that she would spend tomorrow morning teaching me the finer points of how to walk, talk and act like a woman. "You're pretty good, but there are a few rough edges to be ironed out. Before I finish with you, nobody will ever be able to tell the difference," she added triumphantly. It was almost as if she relished the challenge of making a woman of me. We spent the rest of the evening watching television as it was rather late and I was by now very tired after what had been a long and exciting day. Anne broke the news to me that while I was getting my instruction she'd taken the clothes that I'd arrived in that morning and thrown them into the dustbin. Frankly, I didn't care a bit. I wasn't planning to wear them ever again. Just before bed as I was removing my makeup and getting into a silk nightie I decided to spend half an hour beginning writing up my story in this diary. I was looking forward to spending as long as possible in my new identity as Carol Holloway, Anne's cousin from Surrey, and I didn't want to forget a single moment of it. (c) Carol Holloway 1998 (Email: [email protected])