Caitlin Knows Best free porn video

Foreword Authors note: Those of you that have read 'The Siblings' will know that Lucy and I moved in together a couple of years ago, since when I have very much enjoyed helping with her hobby of genealogy, with considerable success. We have traced our mother's ancestors back to the early eighteenth century starting with our great-great-great- grandfather, Horace Templeton. Horace migrated from England to Hong Kong in 1834 with the first of his three wives, all of which he outlived and each of which presented him with four children. On Mum's side alone we traced 224 relatives in total, a large percentage of which had returned from the Far East to settle in the UK. The Templeton fortune ? and it was a big one ? was made in the rag trade, from spinning to weaving the fabrics and to the making of clothing. We have traced the current major shareholder, a Miss Maria Templeton, to Birmingham, England and discovered in so doing that her father had changed the name of the company immediately after the First World War because of some unknown German connections. Maria is a spinster and seems to have accepted she will have no natural heirs and I have started her story at the time she tried to adopt a young couple of orphans with a view to them taking over her empire. The story is related by one of those orphans and is entitled Caitlin Knows Best By Donna Dee I was raised in St Phillips Orphanage and, until I was turned 12, knew no other life. The orphanage has no record of who my parents were, or if they have they will not tell me, and I have no known surname. Therefore any chance of my trying to trace my birth mother and father is strictly limited as to all intents and purposes they are both dead, as well they might be for all I know. There were 4 dormitories housing about 40 of us orphans in St Phillips's at any one time; As a general rule ten of them girls and 30 boys, all around the same age; we schooled together, ate and played together but, of course, the girls were not allowed in the boys dorms and visa versa. The name given to me (by the sisters I presume) was Laurence ? as I said we had no surname and were all known as Phillips, and so far as I know I have no living relatives. St Phillips wasn't one of those homes you read about in books by Charles Dickens, it was a clean, reasonably modern building, centrally heated with well decorated rooms, decent carpet and, of course, all mod cons and really good bathrooms. The food was very nourishing and well prepared, (there was usually a choice) and there were no complaints in that respect. We had good clothing, not always brand new but always clean and we had far more freedom of choice than a lot of kids who live with their folk, we could choose what to wear for instance and how long we grew our hair, that sort of thing, my own at the time was worn rather long to just touch my shoulders. We had all been allocated birthdays as near as possible to the sister's estimate of when our real birthdays might have been and on those days we had presents, and of course we had presents at Christmas. I learned later that an eccentric millionaire was the patron of St Phillips and all I can say is thank you very much. There were visitors who called and had talks with us, usually every couple of months to be sure we were not mistreated. There was discipline, of course, it would be chaos without, and we all had our chores to do ? on a rota so that over a period of time we all did the same. I got the cane two or three times but it wasn't that bad. There was one visitor who called every six months or so, we speculated that she might be the millionaire who looked after our interests but decided in the end she was probably too young ? not that a 40 year old woman would seem all that young to a twelve year old. Her name was Maria Templeton and I discovered that she had taken several children from the orphanage and found them good homes with childless couples. I don't remember her speaking to me, other than to say 'hello,' but she always smiled nicely and I particularly liked the way her brilliant white teeth sparked between her bright red lips. Sometime after my 12th birthday the senior sister sent for me, I wondered what I'd done wrong, but she smiled as she sat me down. She asked me if I would like to go and live away from St Phillips, with a woman who was looking for two teenagers to adopt, one boy and one girl. She told me that the woman was wealthy, had a lovely home and, since she had no children of her own it seems she wanted to train a boy and the girl to work in one of her shops with a view to becoming the manager and manageress when they were about 21 ? it was a wonderful chance to build ourselves a future. Obviously our schooling would continue and this would probably be in what we might call our spare time, but, she said, it was very clear to her that this was the opportunity of a lifetime for orphans like us. I asked who the girl was going to be but the sister wouldn't tell me until she had asked the girl if she wanted to go. There was no pressure on either of us, if we didn't like the idea we only had to say, but she said I'd be a fool to turn it down. I thought that as well. I asked if I would have the chance to meet the lady first to see how we got on. "Well of course you will, Laurence. She has seen you here a number of times over the last two or three years and picked you out ages ago." The next day I was told that the girl who had been chosen was Colette and since we liked each other OK I had no problem. At the end of the week we were told that we would be spending the coming weekend at our new home to see how we got on. "Best behaviour mind," said sister as we set forth. It was, of course Maria Templeton's home we were taken to. First of all she wanted to know if the sister at the orphanage had explained what this was all about and I confirmed that she had. Having done so she made it clear that for this weekend we were her guests and that we were here to enjoy ourselves. "But," she said, "if we do like each other and intend to try to make this work, you had better understand that you will be in for some very hard work. She told us that she owned a large haberdashery shop in the city and a chain of smaller boutiques dotted here and there in the West Midlands. If we came to live here with her, there would be a private tutor come every day from eight, a tutor she knew well and trusted, so there would be no point in our trying anything on. Then, after lunch we would study haberdashery and learn everything there was to know about the trade. We would spend two afternoons a week in one of the shops, just observing at first but then serving and becoming generally useful. After evening dinner, which we would take with her, we could relax, watch television with her in the lounge or in our rooms. If we visited each other's rooms the door must be left wide open. We would get pocket money and a clothing allowance, which would be generous as she wanted us looking a credit to her at all times. She said the only thing for which we might be punished was if we did not keep ourselves spotlessly clean and our rooms tidy, but she didn't indicate what that punishment might be and I for one had no intention of finding out. Miss Templeton pointed out that there was a butler and several servants, but that they were her servants, not ours. We must NEVER ring the bell and request a service of any kind. The butler's name was Truscott and that was how she addressed him, but we must call him Mr Truscott. Of course, if any of the servants offered a service we wanted we were free to accept. Dinner was the one exception when we could make requests for things we wanted. We would be introduced as her nephew and niece and we were to call her Aunt Maria or Auntie as the case may be, EXCEPT in any of the shops when we must always call her Miss Templeton or ma'am. "I want you to think of this as your home. Presuming that all goes according to plan, when you are sixteen you will be formally adopted as my children and will then, in all respects become my sole heirs and I imagine you can see there is plenty to inherit. Once that happens I will allow you authority over the servants, provided you have by then proved to me your ability to exercise that authority. Watch and learn all the time, treat people as I treat them and you won't go far wrong. Phew!" she exclaimed, "I do hope that's covered everything because I do hate being bossy. Now then my dears, do you think you will be happy living here with me?" We both assured her that we believed we would and I know I said it from the heart. I said just now we were well fed at the orphanage but it paled into insignificance at the spread laid out for us that weekend. After each meal the three of us sat and just talked about everything, subjects to interest both Colette and myself. My bed was so comfortable I could have slept for a week. Sunday evening came far too quickly for me and I was asked if I still wanted to come and live with her, remembering that once I moved in I would be expected to work really hard at all my lessons. I said I did but to my amazement Colette said no thank you. She was asked if she was really sure and she said that she was and so that was that. I was driven back to St Phillips Monday morning to collect my things, such as they were and I was back at what Aunt Maria said I must now think of as my home by lunchtime. The housekeeper was the butler's wife; she showed me around the house and told me where I could and couldn't go and then she came with me to my room to help me unpack. I was somewhat surprised as she held up each item as if it were a dirty floor cloth and then to see her deposit most of my clothes in a large bin. She was very friendly and, noticing I was concerned smiled nicely as she told me to look in the cupboards and drawers. In the cupboards I found suits, trousers, shirts and outdoor coats. In the drawers were more sets of underclothes than I'd ever seen. There was sports clothing, a tracksuit, half a dozen pairs of shoes and trainers. "Those are all for you, Master Laurence; it's a pity Miss Colette isn't coming," said the housekeeper, "there are nearly 40 pairs of shoes in her room, but then women do need more than boys, don't they. Now then young man, Miss Templeton is out all day but she has left instructions that you are to try on each of these suits and casual trousers and that I am to check that they fit you properly. Put them on, one at a time obviously, and come to my rooms or the kitchen to let me see you before you change into another. They should all be perfect; your measurements were taken by the sisters at the orphanage and passed on to the tailor. When we are done, put on whichever casual outfit you prefer and relax until it is time for dinner. I will see you later." Mrs Truscott then left me and I spent the rest of the afternoon doing as she said. Needless to say all the suits were a perfect fit. I joined Miss Templeton for dinner at seven and was rebuked for failing to call her Aunt Maria ? a mistake I was not to repeat, she said. The meal over she made me sit with her on the settee where she held my left hand between the brightly painted fingers of her two and told me what to expect from tomorrow onwards. "Every morning you will be awoken at 6.45, you will put on your track suit and run the length of the drive and back, twice, a distance of about a mile and a half. Take a shower and dress for school in a blazer and flannels, shirt and tie. Breakfast is at 7.45 in the main kitchen, lessons start at 8.15 until 12.30. Your tutor is Mr Bond and, as I told you at the weekend, he has my full confidence. You will have an hour's break for lunch that you will take in the kitchen and after which the chauffeur will take you to the main shop where you will report to Caitlin Ross at 1.45. Caitlin will teach you all about the haberdashery business. I truly believe there is very little that she doesn't know about the business so you just listen very carefully, she is a font of knowledge. This routine will be repeated Monday to Friday each week. Any questions?" I said that I fully understood her instructions and hoped to be a credit to her. I hadn't expected Mr Bond to be quite so old ? though maybe he just looked old, but he certainly had a way with his teaching methods. He made every subject seem interesting and I know he gave me good reports each month. As to meeting Miss Ross for the first time I had even less idea what kind of woman to expect, Aunt Maria told me very little about her other than that she was good at her job. On that first afternoon Caitlin was waiting for me at the shop doorway. I submit it is very difficult for a nearly thirteen-year-old boy to accurately guess the age of a woman who is obviously older than him self. In the end I guessed she was in her early thirties, mainly because of the position she held in Aunt Maria's organisation. She wore a smart black suit with a knee length skirt, black stockings and modestly heeled shoes. Her name was printed on a badge followed by 'Managing Director' and this was pinned on her lapel, just below the buttonhole. I thought she was very attractive in spite of her severe hairstyle, most of which was wound into a bun at the back of her neck. She wore make-up, her blue eyes shining out from below fairly heavily painted eyelids and her bright red lips stood out from a peachy complexion; her nails were brightly painted with the same colour and she smelled absolutely divine. It was obvious to me that she regarded me as a mere schoolboy as she shook my hand quite firmly, said I was to call her Caitlin and bade me follow her as she led the way through the store and up two sets of stairs to the top floor. I noticed that all the other sales girls looked exceptionally smart in black dresses and that all of them wore their hair in buns or ponytails. "Staff may not use the elevator unless escorting a client to a different department," she announced as we climbed the stairs, "and that includes you." I followed her into a large room in which there were literally hundreds of items of ladies underwear stacked on rows of shelves; there were stockings, knickers, bras, slips and the like from which all the labels had been removed. "This is a job in which you literally start at the bottom," she smiled, handing me a pair of silk stockings. She told me the meaning of the word 'denier' and bade me slide my hand down the inside of the stocking ? and, of course, my rough fingernails snagged it in three places, and I thought I was in for a rebuke. "My fault," she smiled, "I really should have checked your hands beforehand." Taking up the receiver of an internal phone system she tapped three buttons and spoke clearly into it once it had been answered. I could, of course, only hear one side of the conversation. "Hello Beryl, Miss Ross here, are you with a client?" (reply) "No, then bring your emergency kit to my office at once, please." She replaced the receiver and smiled again, I thought once more that she had a lovely smile. "Finger nails cause more damage to hosiery than anything else which is why the nails of all staff are checked by the supervisor twice a day." There was a tap on the door and a middle-aged woman I soon realised was Beryl came in carrying an attach? case. Caitlin nodded towards me and Beryl started her examination. "My God!" she said, what have you been doing, digging up potatoes with your bare hands?" She got to work with an electric rotary file and spent half an hour smoothing out all the snags before asking Caitlin if she should coat them. Caitlin said, "Yes, Beryl, but use a matt finish that wont show, we don't want him looking like a sissy, do we? The stuff she put on smelled a bit like nail varnish and it soaked in and dried almost instantly and was quite invisible once it had set. "That will help prevent snags from re-appearing," Beryl said, "all the staff use it under their nail polish, it lasts about a week." "Thank you Beryl, that will be all. Bring me up a manicure set and a bottle of that stuff before 5.30 please." "Yes Miss Ross, thank you," said Beryl as she departed. Caitlin told me to take care of my nails, not to cut them too short though obviously I was not to let them get too long either. She continued to instruct me in handling stockings, that the lower the denier numbers the finer the silk or nylon. She told me why seams down the back had lost their popularity in recent years with some people. She thought that wearing seamless stockings was a sign of laziness. Over the following two years I was taught to recognise the look and feel of silk, rayon, satin, polyester and so on ? to tell the difference between good and inferior quality garments, to assess their value and assess a selling price that was not necessarily based on the purchase price. I found this very hard at first, but Caitlin said I was doing extremely well, for a boy. This training was kept up month after month and I thought it would soon be time for me to try my hand at actually selling lingerie in one of the shops. "I was making good progress," Caitlin said," but I was at a distinct disadvantage because the only way to really appreciate the luxury of women's underwear was to wear it." I wasn't sure what, if anything I could do about that. I had noticed on several occasions that my aunt, Caitlin and Mrs Truscott for that matter were adept at making this kind of suggestion and watching for my reactions, and after a few days I asked Caitlin if my aunt expected me to suggest that I try wearing women's undergarments. "Good gracious me NO, Laurence, whatever next. You should know by now that Miss Templeton does not involve herself in your training programme in any way ? that has all been left to me." She thought for a few moments then added, "Having said that it is a very good idea of yours, after all, no one will ever know what you have on under your trousers, will they?" She nodded thoughtfully and added, "Yes, my dear, I think that is an excellent idea, I wish I had thought of it myself. We shall start straight away." "Oh my God," I thought, "What have I got myself into now?" Caitlin was smiling even wider as she picked out a pair of panties, a suspender belt and some nylons. "Go behind the screen, take off your shoes, socks, trousers and Y fronts then put these on," she directed, "suspender belt first of course, you should know that by now. Be extra careful of your fingernails and make sure you don't ladder the nylons, roll them on gently as I showed you on the model last month. Put on the panties and replace your trousers and walk around until I return, I wont be long. Oh yes, and Laurence," she called, "do not be embarrassed, no one will ever know, unless you tell them." With that she left the room and I went behind the screen to do as I was told. I couldn't help but feel embarrassed, but putting on the clothes was a sensation in itself; the feel of those stockings as I pulled them up and fastened them to the straps on the belt and the silky touch of the panties gave me a hard on I would never forget. I looked at my legs in the mirror and thought how much nicer they now looked and I was very reluctant to put my trousers back on, but of course I knew I had to. Caitlin returned with a pair of shoes that had a 2" heel and bade me put those on as well and then to walk around. It wasn't as difficult as I had expected and I quickly got the hang of it. Suddenly she shouted, "Stop." Then she told me to drop my trousers and added that I was not be silly when I looked a bit coy. "You have nothing there I haven't seen before or that interests me in the slightest. I merely wish to tighten the straps on your stockings." I dropped my trousers and she took a good two inches out of every strap making the stockings much much tighter and making them feel even nicer. She totally ignored my bulging penis and asked me how the things felt. I said they felt so good I never wanted to take them off, and then I added, without thinking what I was saying, that she would never believe just how good they felt. Then, realising what I'd said, I tried to cover up my mistake. "That's all right, Laurence, my dear, I do know just how you feel, but I have been wearing them all my life, remember?" She made me leave my trousers off and walk around her office, correcting me when I took too long a pace or turned too quickly. All too soon it was time to go home and I went towards the screen to change back into my own clothes. "Do you want to keep them on, Laurence?" Caitlin asked me, smiling again because she already knew the answer. "Just put your trousers back over the top and put your own shoes and socks back over the top, we don't want everyone to know our little secret, do we?" Caitlin put several quite different pairs of panties in a bag with several pairs of nylons and told me to wear a different pair each day, then tell her which I liked the best and in what way they felt different. They all felt wonderful to me but I picked out the ones I preferred and she merely said, "Trust you to choose the most expensive ones." I was sixteen and a bit by now and Caitlin considered I was sufficiently knowledgeable to spend some time on the shop floor ? observing not selling she emphasised. That was fine, I felt quite proud in my black suit, white shirt and black tie and with my name on a badge ? Laurence Phillips, Trainee Manager - but when I offered to serve a lady to some stockings she said quite bluntly, "No thank you young man, I wish to be attended by a female." I quite understood how she felt and thought this might be a major obstacle to my future employment. I told Caitlin and she put me on a different department for work experience saying that she would have to think over the other problem. A few weeks passed before Caitlin returned to the problem when, during a training session in her office, she asked me if I'd like to try wearing a camisole and a bra, just to see how they felt. I was amazed when she handed me a bra that was so fully padded as to be very obvious beneath my shirt and the camisole did nothing to disguise the bulge even when I replaced my jacket. The pleasure that garment gave me was largely in my mind, (I'd got a king size hard again) and I hated having to remove it before I went home. A week or two later she asked me if I'd like to wear a dress and waist slip. I was even more thrilled when she produced a uniform dress so that I looked like all the other staff. Caitlin brushed my hair tightly to my scalp and fixed a band to the back creating a lovely high ponytail that she brushed and brushed to a shiny finish. In the high heeled shoes, (I was now wearing three inch heels at least twice a week), with my false bust standing proudly on my chest, I really felt like any other salesgirl. I was hoping that she would suggest I wore some make-up, but she did not. I thought I looked wonderful, I certainly felt very good, but to my intense disappointment, Caitlin shook her head sadly. "It's no good, Laurence, for you to look anything like a young girl we'd need to take a good six inches out of your waistline, and that will take months of dieting and exercise, not to mention the use of one of our stiffer corsets, and I doubt you could stand wearing one of those for long enough to do any good, what's more you'd need to sleep in it as well." I said I wanted to try but she ignored the remark and added, "You could only remove it once or twice a week for a shower or bath and then it would need to go back on again, and you'd need to put it on at least as tightly every time." I insisted I could stand it because I now knew that I wanted to do this more than anything else in the world. Eventually she agreed to my trying a corset, and it wasn't long before I realised for myself just what she meant. She helped me into it easily enough and clipped it shut down the back. That was fine, I thought, I could stand that and I must have looked a bit cocky because she laughed and picked up some very long, strong looking laces and started to thread them through the eyeholes. "We haven't begun to torture you yet, Laurence," she laughed, and I gasped as she gave the first real tug. I thought she'd cut me in two but her tape showed that I'd only shrunk by just under four inches. "I'll let you off with that for today but be warned, I want another inch off tomorrow and the day after." I made it, don't ask me how I did but I made it and when Caitlin helped me into another works dress and it hugged my new shape, I really felt that I looked like a woman. "Before we go any further, Laurence, I need to be really sure that this is what you want ? it's a commitment for life, you know?" I said I did understand and I did want this more than anything, so she said OK, but that my Aunt had noticed how much slimmer I was looking and that if I was going to continue cross dressing while I was at work, and to use make up while I was working then Maria would have to know as she would most certainly visit me wherever I was to see for herself how I was getting on. She said that, in effect, I'd need to do it full time. I thought that idea was wonderful. Caitlin had anticipated my answer and had started me on hormone tonics and tablets some time before. Coupled with the effect of my corset which pushed my chest up (and my backside down), my breasts no longer needed the silicone breast forms had worn until recently, though not at home of course. I was almost eighteen by the time Caitlin was convinced of my sincerity. "OK Laura," she said ? (We'd changed my name tag six months ago and she always called me Laura now, even when I wore my suit!) ? "It's time we told your Aunt. I am coming to dinner on Friday, so you can put on your uniform dress and wear your make up, then we'll see what she thinks." I was ecstatic, but my Aunt was about to throw a spanner in the works, and how! On the Thursday night beforehand she told me that she had decided to finalise my adoption as her son, that my name would be Laurence Templeton, and that from next week I would be promoted to general manager. She said that to honour the occasion she had bought me a new dress suit, black tie, and since Caitlin was coming to dinner, the two women would wear evening dress in my honour. Obviously she expected me to be thrilled, and I was, except that it put off my wearing a dress and telling my Aunt of the change I was making. I said nothing, of course, but I couldn't wait to see Caitlin next day and to cry on her shoulder (before getting changed and putting on my make-up, of course). I was told not to worry, to trust Caitlin to sort it out. She said she would be at my aunt's house just after six and I was to see her in her room to see what she had arranged. I went there as ordered, as soon as I heard her arrive and, in her room, I saw the gown I imagined she intended to wear ? it was off the shoulder and looked fabulous. When she told me the gown was for me ? that she had another in the cupboard, I really did cry with happiness. Caitlin said we hadn't much time, there was a lot to do, so we bathed together and as we did she fondled my real but tiny breasts and kissed me deeply on the lips. Then she shaved my arms, legs, chest and just trimmed around my pubic area. We donned new underwear and returned to the bedroom just as Beryl appeared and started to give me a full manicure and another girl I'd never met began to work on my face. Beryl fitted small but obvious nail extensions and painted them, and my toes while her friend gave me a full makeover, pierced my ears twice and put in some danglers, even though she said I ought to wear small studs for the first few days. I wore the sheerest nylons, several waist slips, designed to throw the dress out at the bottom and I carried an evening bag. I wore 4-inch heels ? the highest yet ? in which I walked quite perfectly to everyone's amazement. What surprised me most, however, was that the butler, the housekeeper nor any of the staff so much as raised an eyebrow when they saw me come down the wide sweeping staircase to dinner. I discovered later that my new 'Mum' had put her up to this, it seems she had already seen me in the shop one day on an unscheduled visit and had arranged this surprise with Caitlin to honour the special occasion. In spite of the age gap, Caitlin and I became lovers ? for I am still technically a male, but she said it was because of the hormones I'd taken that we'd have to be satisfied with mainly oral sex. I was content, Caitlin always did know best.