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Looking For Love By BOBBIESHAW I had always looked forward to finally getting out of school and going to work, when I finally turned sixteen I just mostly put in an appearance. Going to my job at a fast food outlet was more fun and the money gave me freedom from asking for anything from my parents. By the time June came, the idea of failing had long ago been accepted and I did. Not only did my dad, who never said much nor was around much, wanted me out, and out and away I went. Finding a place that I could afford was difficult, a one-room place with a shared kitchen down the hall close to the university for the summer was all I could find. As I could not get full time at work I applied for other work and by the middle of August I got a job cleaning an office building evenings. It was full time and more money but after a few weeks it became somewhat lonely. Every evening, Monday through Friday from 5:00 to midnight wasn't too bad but then I had to come in on Saturday's at 1:00 to 6:00 also. By the time I slept in and then got ready my social life had ceased to exit. Now I had never had much of a social life anyway as I was somewhat of a loner all through school. My parents did not venture out of the house unless absolutely necessary. Any social outings had ceased years ago. Some of the people at my part time job had been nice but I was not there long enough to really get to know them. And school had been anything but a pleasant experience! I had always been small and somewhat frail compared to the others at school and had always taken a quiet approach to things around me as not to stand out too much. Anyway emptying garbage cans, mopping floors and cleaning carpets soon lost its appeal and each day got a bit gloomier. My boss always smelled of not having had a shower for weeks and sounded like he didn't care either. I stayed as far away as I could from him and quietly did my job, eager to finish and go home but not eager to stay there alone. Anyone I might have called a friend was still in school and I really didn't want to talk to them either. About the middle of August I was opening the door to one of the offices and just as I entered I noticed a light on in the back. I slowly worked my way down the hallway, leaving the one with the light on to the last, hoping maybe by the time I got there it would somehow be out. Not so! The door was open and sitting behind the large desk was a woman, her head bend over a pile of papers. I quickly moved on down the hall hoping she would be gone before I had to come back her way. No such luck, the light still shone and this time her head was up! "Come on in, you can start, I am just about finished here for tonight." Slowly I came in and keeping my head down I started my chores. Within a few minutes she was up and gone, her silhouette gliding down the hall into the darkness. I had not gotten a good look at her but enough to remind me of one of my teachers at school. She had to be mid to late 20's, feminine for sure but something about her was cool and somewhat aloof. A strange mixture somewhat and I found myself thinking about her for the rest of the evening and that made the time go. A couple of days later she was in the office again and this time I stayed clear until she came out and up to me in the hallway! "I will be here for a while yet so why don't you come in a do my office while I get some things from the library?" As I did her office my mind was on the black hair pulled to a bunch at the back of her head, the thinness of her hands, especially the fingers and her face! She was not modelling beautiful but she excited me! It was a thin nose but one that was noticeable on a face that was somehow strong, not in an athletic way but capable strong if you know what I mean. Maybe a better word is confident. Just as I finished up she reappeared and casually took her chair behind the desk and I found myself edging towards the door, wishing to be gone into the darkness. "How long have you been working here? You were here the other night weren't you?" I mumbled something about a couple of weeks and yes it was I the other night, still trying to make it to the door! "Well you seem to do a good job, some of the cleaners in the past have been less that acceptable. Are you getting enough hours?" All I could do was nod a yes and then when she asked me about when I worked I had to open my mouth and tell her my times. Something about it felt like I was in school again, teacher and student, and the student was about to get the dickens! "Nice to hear, if you have any problems let me know!" With that I finally felt I could leave without sticking out and feeling foolish. I don't know if I had a dream about her that night or I was just thinking about how odd I had felt in her office for the next day or so but my mind kept going back to her. Especially laying in bed at night or when I got to work. I found myself looking to see if her light was on when I came to her outer office and then I found myself going up to her floor shortly after 5:00 when I was sure all the normal office staff was gone. I missed her for the next few days but she was a lawyer as her office was a law office and she had the biggest office there! With that knowledge I knew all I could and would do with her was fantasize about loads of things, if only things had turned out different. Then on Friday she was sitting in her outer office when I arrived! "Hi here, I didn't catch your name the other day but I wanted to talk to you about something if you don't mind?" After mumbling out my name I stood fidgeting and waited! After a bid she slowly smiled which grew into a broad grin and motioned me to follow. She sat at her desk and after a minute or two that felt like an hour she motioned me to sit. "Well Bob, or is Robert?" My nod confirmed what she believed. "Okay Robert, I am giving a small patio party tomorrow evening for some of my fellow workers and I wondered if you would like to be involved? I know you are supposed to work here at noon but I have spoken to your boss and made arrangements for you to come to my place instead! I can pick you up here at say 11:45 as I have to come in the morning to do some things." The wind had been knocked right out of me!!!!!! My head was spinning with the possibilities and they were too much to deal with so I just sat and nodded! All that evening and the next morning my head was full of wonderful things that might happen at the party! I was ready in my best slacks, matching shirt and good shoes with a fresh haircut and over an hour to shave after a long soak in the tub. Unfortunately I was a bit early and sat waiting in the outer office. Finally down to the garage, into a new BMW and off we went, over the bridge and into an older part of town close to the river and quite expensive for sure. All she had said was hello as she went by me, motioning me to follow. Nothing was really said until the car was in the garage and we had made it to the big kitchen looking out over the patio and pool! "I will have to go and get changed, why don't you find something to drink in the fridge, we can have a quick lunch and then get busy!" I was kind of perplexed but when she came back down it was clear as could be! She had changed into a sort of jogging outfit, hair firmly tied up, runners and any makeup she had on was gone. She was quite different! Seemed a bit older somehow, maybe a bit starker, not so feminine as anytime before. A quick bite with me feeling more odd than ever, and then worse when she stopped, looked me up and down and then stood there; slowly shaking her head. "You don't want to get those clothes dirty, I will find you something to wear, there is a bathroom down the hall, you can change there." Somewhat deflated I slowly hung my things up on the hanger she offered with the pile of material she came back with. Upon going through the pile I was left with 3 options. The first was to leave, most likely lose my job and then what? The second was a pair of sweat pants and cotton shirt, both white in colour with a small red rose on the pocket of the shirt! The third was a white pair of shorts, elastic waist, rather large at the leg! A pair of white thongs rounded out the possibilities! "Very nice, very nice indeed." Was all she could say as I produced myself in the sweat pants, the least of all evils? We started in the house and since in was air-conditioned real well it was not too hot in my 'work' clothes. She seemed to find something for me to do and then was gone on other missions in a minute or so. By the time the house was done she opened the patio doors and ushered me out to the patio. In less than 10 minutes I was sweating and wishing I could get the sweat pants off! The beads on my face caught her eye and she suggested I might like to do just that as she pointed to the bathroom and gave me a funny look! It was that teacher look again! Reappearing in the shorts caused a red face as I rejoined her but she must have thought it was the heat, as she paid no attention to it at all. Soon I was back at work cleaning and getting the yard ready. By 4:00 she seemed to be satisfied that all was in order and we sat down for a cool drink. She just seemed to keep staring at me and each time I looked up I was forced to look down and wonder what she was thinking about. Finally she got up. "You had better get out of those clothes, they need to be put in the laundry. I have to have a shower and get ready, there is a shower in the bathroom upstairs, and you need one too. You did a nice job here today, thanks!" Not only did I feel better, but also her tone was comforting in an odd way. Also she had not said anything about me leaving! All my good feelings came to an abrupt end and I realized the bathroom door had opened and she had come in! "I just came to get your dirty things to put them in the laundry." And with that the door closed and all was quite! I had been left with a large white towel just outside the shower and a pile of white on the counter top. The towel was easy but the other was a cotton jacket type garment that I knew some people wore after a shower or bath until they got all dry and then changed into whatever. Since she was the only one living here I knew it had to be hers and therefore??????? It was either the wet towel or the jacket, which came down to about where the shorts had come, that was the choice! Since the jacket was oh so open at the bottom I wrapped the towel around my waist too. In the bathroom downstairs were my pants and shirt and I was just about to pull the pants on when she knocked on the door. "I have been trying to find you some shorts and socks to wear, you need something for sure, no one comes to my parties with no underwear on, too many chances of something embarrassing happening!" She was right on two fronts, I was going to stay for the party and for that I was jumping for joy and I did not want to cause her any embarrassments for sure, let alone myself. My first social function in months and not dumb school kids or drunks. I hated drunks and I hated especially when they got belligerent and wanted to pick on someone. Especially someone smaller and not wanting to fight back! "Are you decent?" The door slowly opened with her seeing me with one leg pulled on and the other laying on the floor and me all tied up trying to get back to a straight position. Thank god for the robe, no matter how short it was! "Come with me. I have some things that might do upstairs. You can pick out something you are comfortable with." She had picked up the towel by now, throwing it in the laundry room as she headed towards the stairs again. All I could do was follow! The second door to the right revealed a bedroom with a single bed, one dresser and a closet door. All white but sparse and plain looking, not what I would expect to see in her place at all. She opened the dresser, sorted through a few things and then sort of through some items on the bed. With that she turned and headed out the door again! "See if there is anything there you might like and then come back downstairs." The door closing behind her was one thing but the stuff on the bed was another for sure! I knew it was underwear and I knew it was not for me but I also knew she intended it for me? Not only that, if I wanted to stay for the party it was surely for me! The first one must have been nylon or something like that as it was definitely a girl's under thing! I sorted all the cotton ones out and then tried to pick one that at least might give me some illusion of masculinity if only in my mind. The closest was a plain white one and I closed my eyes as I pulled it up over my legs and into place. The worst part of it was the elastic closing in around my waist and thighs, holding it firmly in place and letting me know just that! Thank God my housecoat hid them from view! Back downstairs she was waiting in the bathroom with a hand full of material, which turned out to be socks of some kind. They were black but when I pulled them on after my pants and shirt they stretched out very thin and by the time the elastic at the top snapped tight they came almost up to my knees! Again I knew whom they had been meant for originally but as I stepped into my shoes I knew who had kind of inherited them for the evening. I felt really odd as I came out and she was waiting for me in the kitchen, looking me up and down, as she seemed to check and make sure everything was okay in some way. She was quickly gone and I was on my own until just before 6:00 when she came back down in a black pant suit, heels, hair let down so as to go half way down her back and with the makeup she looked a lot different. More distant, less approachable and way out of my league and I felt quite alone as the first of the guests started to arrive. She said very little directly to me most of the evening and I was content to stay close to the kitchen and seemed to fall into a format of her coming to get certain things and then on her next trip I would have them ready. The only guests I really saw were through the window and on the far patio at that, and that was fine by me, I knew I would not fit in anyway. One thing that kept coming back to my mind was the elastic and the feel of the material I had on under my pants for some reason. I wondered when she had last worn them, how they might look on her, (that was a difficult picture to form for sure), and that progressed to how she might look in some of the other one's that were on that bed upstairs. For some reason they all did not fit my image of her at all and then I started to wonder how it might feel if I had chosen another pair! Especially that first nylon pair! I had never worn nylon, only cotton and this was different cotton once the elastic was added and I knew they were hers to begin with. My thoughts moved to how close I was to her now that I was in something she had worn and something she had worn so close to her body and so intimately! When the last guest had left, she came back into the kitchen, gave me a light peck on the cheek with a big smile. "You were a dear tonight Robert. I couldn't have done it without you. Thanks for the help, I am so tired how about I call you a cab, you don't mind do you?" At that moment I was not really listening!!! It seemed but a minute and I was in cab with an envelope pressed into my right hand as I left her. I waited until I was in bed before opening it and as I was getting ready for bed I really did not want to take off my... er... her... er... underwear as it was so much more personal in a way to keep them on. In the envelope was a $50 bill with a thank you written across the front of it. I tried to see if I could recognize her perfume on the bill but no way. By the time Monday came I was anxious to see her again and by the time everyone left I was more than anxious for sure. She was not to been seen! It was the same each day all week and by Friday I was almost heart broken! In fact I had looked at the things of hers I had left with and after washing them, I ironed them and took them to work each day in a small bag for her. On Friday when she was not there I snuck into the storage room in the back of her office and without letting myself think about it I quickly shed mine and put her things on under my jeans. I felt somewhat better for a bit and then started wondering if I might ever get to go to her place again. That night I wore the underwear to bed again and then I rinsed them out in the morning and waited for them to dry so I could wear them to work also. About 4:30 as I am finishing up my boss tells me to go down to the parkade before I go and check the doors? Strange as he always did it before, but just as I got there she pulled up in her car and rolled the window down! "Hi there, can I buy you a bit of dinner for being so nice last week?" And with that she reached across and opened the door! We were off and gone before I had a chance to think about it. We picked up fast food and headed to her place. There was little conversation and just as soon as we ate she told me she had some calls to make and maybe I could tidy up a bit. By the time she came back down I had finished up and she had changed into a black lounge type of outfit, slacks and shirt but a lot more casual that at the party. Sitting on the sofa she motioned for me to sit in the chair opposite and just as I went to sit she almost yelled! "Oh my God, not in those pants! I forgot you just came from work! I didn't realize how dirty they are! How about we find you something that's clean and then we can have a nice visit." I didn't have a chance to say a thing; she was gone and back with the sweat pants, shorts and top from the last weekend in hand! "It is a nice evening, how about we go out on the patio? A bit warm yet so how about these?" The shorts it was and when I went to the bathroom to change I looked down to see and realized I had on the undies from then also! The shorts covered them up and that was a relief but the top was a bit different than before! This one had a bit of a collar and the short sleeves had elastic holding them in place. With the thongs I was all in white and she was waiting all in black just outside the door! It was a strange type of evening! I with bare legs and arms and she with pants and long sleeves! Me all in white with my light hair, her all in black with her black hair! In the semi darkness she asked a lot of questions and I answered the best I could, as they were not really personal ones but as the time wore on I seemed to answer more and more of a more personal nature. By the time we headed inside about 10:00 I felt she must know pretty much everything about me and I didn't even know her name! "Time to go now Robert, it was a very nice evening and I hope you come and visit again. By the way how do you like your work, any problems there?" I heard myself complain a bit about my boss and how he was, rude, dirty, and not pleasant most of the time but that I kept clear of him if possible and got by. "Well if you run into problems let me know and if we have to make some changes we can, okay?" Just then a taxi pulled up!!!!!!!! "I... I... well... have to change?" "No time for that now, your ride is waiting, run along and have a nice sleep!" "Thank you... I don't even know what to call you?" It was all I could think of to say as she ushered me out the front door! "Tess, my friends call me Tess, that will do for now, okay?" "Oh, yes, sure, thank you Tess for everything, thank you very much!" Getting into a taxi in a white top and shorts, with white thongs while a woman paid the taxi driver and told him where to take me while I said nothing gave me a strange feeling and by the time I got into my warm bed in the dark I tried to figure it all out. The best I could do was come up with a feeling of having had no choice but to sit quietly and not kick up a fuss, it had been the right thing to do! She was nowhere to be found the following week and by Saturday I was down in the dumps. Most of my acquaintances were going back to school and I felt even farther removed from everything. I had not spoken to my parents in over three weeks and they had not called either. The old man had told me time and again if I quite school he would disown me and I guess he meant it. It was Labour Day weekend and going home to my tiny room Saturday was a real downer! Monday morning, when I was called to the phone her voice made me jump! "Hi there, I was thinking of maybe an afternoon by the pool if you are free to come over? I will come by at say noon or so to pick you up, how does that sound?" I just got a yes pushed out as she continued on. "It promises to be a nice day so, let me see, did you wash that pair of shorts and top you had gotten from me last weekend? That sounds appropriate enough for a nice day in the sun! See you just after noon, bye!" Now going over there was what I really wanted to do but going in those things seemed weird so I got myself all cleaned up, nice and neat and then found a pair of jean shorts and a blue tank top and some flip flops I had. Her things were folded nicely in a bag and I went down to the front door to wait. Noon came and went then it was 12:30 and then 12:45 and I was almost shaking, knowing she was not going to show up! Finally that BMW came around the corner and I wanted to leap for joy! As I crawled in, giving her a big smile all that I got was a deep frown in return! There was nothing said all the way across town and even when we got into the kitchen and stood facing each other there was still silence! "What's this?" As she asked the motion of her hands clearly referred to my attire! All I could do was look down and grimace, then hold the bag with her things in as a sort of peace offering. "I don't like blue jeans at any time, and I expect some sort of dress code in MY house that is suitable to me! I didn't think that was going to be a problem with us or I wouldn't have called today!" "Ah... er... sorry! I... er... well, I didn't think it was..." "I can see you didn't think, that is really obvious and maybe you need some lessons in thinking clearly, what do you think about that Robert?" It was a very strange feeling! Part of it was my mother talking, partly a teacher and I wanted to be here with her and that made it different also, very different and something I wanted to try and make happen! I nodded and looked down at the floor and waited, just as I had done when the old man had gotten angry about something. "Time for a swim anyway, we can discuss this again IF it needs to be discussed that is! I will get you a bathing suit, you can get changed down the hall." I was so happy to be able to go and close the door while I shed my clothes that for some reason really upset her. I was down to my shorts when a knock, a crack and then a piece of white put on the counter without a word being said. It was a bathing suit all right but with two pieces of cord holding the front and back panels together at the top only! My cheeks were half exposed and by the time the elastic around the edges snapped into place my legs really were bare! The bulge in front was tucked down into the fabric lining between my legs, as I knew it was not wise to let it stick out, even a little bit! On the patio she was sitting in one of the chairs, not in a bathing suit but in the top and shorts that I had brought back in the bag! Raising her sunglasses, she looked me over, motioned to the pool and went back to reading some papers. Nothing had been said but it was clear, she wanted me in the water and that is where I went. For the first time I really got a look at her legs, longs and slender, all the way up to the opening in the legs of those shorts! I had to concentrate on other things as not to push the front of my suit out of shape. About 15 minutes later she got up, came over and motioned me out, taking my hand at the same time she led me to the cabana on the other side of the patio. Inside she guided me into a changing stall, closing the door behind me after handing me a towel and then I heard the outside door close behind her! In about 15 minutes the door opened again, a white item was draped over the door and I was instructed to put it on. It was the housecoat from before and when I opened the door she was waiting dressed now in a somewhat transparent black blouse, bra, and pants, which looked like leather going down into a pair of black high-heeled sandals. She had gone from white to black just like that! Picking up the towel and my suit I followed her out and towards the house. She stopped at a small line that had been opened and handed me four clothespins and motioned me to hand up my wet things. That was okay by itself, but as I hung my suit up next to a bikini top already there I realized it was the matching piece to what I had worn! I wanted to ask but I didn't want to know why it was here! I knew what the bottoms were when I put them on but until now I could pretend that maybe some guy might wear them in maybe California or Hawaii. I followed her up the stairs and down to the room second on the right again and again she dished around in the dresser drawer, dumped some things on the bed again and then with a smile headed for the door. "You didn't seem to like what you had on last weekend to I guess you want to pick out something a little more to your liking, and mine!" This was said with a big smile but it was not really a question at all! Also the selection had been altered more that a bit! There were two tops only, one with about two inches of shoulder strap and the other with somewhat less, more like an undershirt for a guy but definitely not a guy's top! Only one pair of shorts, so no choice at all! All white with a tie string at the front, elastic waist band and about knee length with wide legs, which along with the top that had the widest shoulder straps was all I was left with. I really didn't want to wear any thing underneath but I knew she would be pissed if she found out. There were only three options! One a hint of yellow left me with only two, both white but there was quite a difference! Before I at least could tell myself that maybe some guys somewhere wore what was offered but this left no doubt as to what and whom wore these! The cotton one had elastic all around and was full like before but it also had a tiny blue angel on the front off to one side with the word 'Virgo' over it in an arch!!!!!!!!! The other was plain but similar to my bathing suit and not cotton! I knew exactly what it was made of and therefore exactly what it was and exactly whom they were meant for, just like the other pair. One was a panty that some schoolgirl would wear and the second was a bikini panty that some girl maybe a little older would wear! It was either, yellow or one of the latter! I just closed my eyes, grouped for one of them and then quickly pulled them on while trying to block out any thoughts that might disturb me. She was waiting on the couch with a pair of white thongs on the floor in front of the chair across from her. I slipped them on before sitting and waiting for her to say something. "Now that is much better than those old jeans dear, I like you in white of some sort, makes you look so nice. Don't you think so dear?" "Yes ma... am." I didn't know what to say! "Would you like to have a nap or maybe you could do a few things for me around here while I finish up some business on the phone and in my office upstairs?" Taking a nap was scary for some reason, maybe taking off my shorts again and having to look at my pan... underwear did the trick and I offered to help. "Okay then, I don't want your clothes to get soiled so soon or you will have to change again! Come we will find you something suitable to make sure that doesn't happen." Now changing again was not what I wanted but her fishing out a plain white apron and tying it around my waist and affixing it in back was not much better, but in a while I forgot about that too. She showed me how to sort the laundry, where the vacuum was, the window cleaner and the stuff to clean the kitchen. By the time she was finished upstairs it was close to dinnertime and I had been at it for almost 4 hours. We found something to eat, I cleaned up while she made a phone call and then she suggested a movie. I tried to undo my apron but it was in a knot and so was the bow that had been manufactured over it! "Keep it on hon, I will untie it later. You can sit and watch the movie without it bothering you now? Can't you?" I just sat down, curled my feet up in my chair and was thankful for the movie to start. It was a dark story about some guy mistreating his girl and then in the end getting sent to jail and really getting paid back by the inmates. During the movie she was visibly upset and asked me for tissue a couple of times, a drink of water once and we had to turn it on pause when she had to go to the bathroom but not when I had to go. I didn't really care and was glad it was over. "Men, sometimes they need to be taken out and given a good beating! None of them were taught any manners when they were boys or they wouldn't be such pigs. Now you are going to mind your manners around me aren't you Robbie? I won't have you hanging around here unless you are going to be all manners and no talk back, right?" I knew it was the movie that had brought that out in her so to humour her I smiled and said of course I would. "Good to hear that dear, now come over here and I will untie your apron. Don't make it difficult, bend down further, sit on my knee and be still! My, you are heavy, here lean over my knees and rest your elbows on the couch while I try this knot. Get your legs over so you are not so far away! Come on!" It had taken but a moment but I was neatly draped over her lap having moved this way and that to make it easier for her to get at my apron. Finally she gave my bum a firm slap and told me to be still and I did! Finally the apron loosened and I went to get up. "Wait!" Her voice was sharper that I had heard before and I froze! Then ever so gently her hand moved down from my waist and ran down the back of my leg closest to her! Then back up to the bottom of my shorts! As I moved a bit her other hand pushed a bit down on the small of my back. "You know you have nice legs for a boy! So young and really quite soft, your skin is really very nice." Very slowly she leaned over and whispered in my ear! I could smell her and her warm breath on my ear made me shiver! "I think I want to keep you in shorts all the time so I get to see your legs, what do you think about that? Yes I think that is a very good idea, something short and revealing just for my personal enjoyment and pleasure. How about that dear?" With that she gave me another slap on my rear and then with a laugh pushed me towards her knees and then up on my feet. When I turned to say something she was already up and headed by me to the kitchen. Then down the hall to the garage, holding the door open for me as she waved for me to follow. When I was dropped off at my door her parting remark was that she would look after my outfit that I came over in and she would pick me up next Sunday at noon and what I had on would be just fine with her. During that week a number of times I checked my legs out in the mirror and wondered why she found them "nice" as I was not only skinny but also rather short at 5' 7". I had never been big nor heavy and at 115 lbs. I did not portray much of a masculine image at the best of times. The best part was my hair had always been kept short to enhance what little image I could muster. By the way it was getting time for a cut, starting to get down over the neck again. The shorts and top got washed and ironed for Sunday but each night I just had to pull the panties... er... shorts on and climb into bed. I was glad they had been the cotton ones even with the little angel on the front. Light and rather comfortable to sleep in they were along with the fact that I knew whose they were and got up with a raging erection most mornings thinking of where they had been before. Sunday I was ready for her, shorts et all. The bathing suit was again ready for me and then the line and then up to the bedroom to get dressed again, as "what you wore over is in the laundry, you don't put dirty clothes back on." The yellow and white pairs of nylon panties were still there but two more had been added also. One was white nylon also but rather large for sure. The other was cotton but one of those thong type, really narrow all over, kind of like one thin piece around the waist part and another almost as thin piece down through the legs. When I pulled them on my er... stuff... kind of fell out both sides, not suitable for wearing and then the clincher, not good for sleeping in! It was yellow nylon, bikini nylon or large nylon and the best for sleeping and having nice dreams was the latter. The shorts were a bit shorter than the last pair and had snaps holding the legs in place on the inner thigh of each leg. Very strange shorts indeed! At least the top shirt had sleeves, short and rather snug but sleeves just the same. As I cleaned up and did some of the chores, (she had some office stuff to do), the snaps on each leg kept popping undone. And each time one went they all seemed to go. And each time that happened they flapped with each step and the white nylon under kept becoming visible! A number of times she caught me trying to redo them up and then she seemed to get agitated all off a sudden! "Get over here and stand still while I fix you! You cannot run around here like an unkempt hooligan!" I stood in front of her while she sat on the chair and did up my shorts! I felt the snaps go into place but after the fourth one I knew something was different! When the sixth one was done she ran both hands down one leg and then up the other without saying a word. Then she turned me to one side, patted me lightly on the bum and pointed to the kitchen. "You forgot your apron dear, go and get it so I can do it up for you before you get your nice things dirty!" It only took a few steps to realize my shorts had been done up but so the front of each leg was attached to the other and the same in the back. Thus leaving me with a complete panel of cloth all around, and an open space between my legs! As I hunted for an apron I wanted one that would go ALL the way around and hide what had become of my shorts! I found one that did just that but by the time she had it done up I wasn't sure which was worse. It came all the way around all right but on the front was a tiny pocket with a bit of lace trim around the edge! I tried not to think of any of it as I continued my chores. Just before dinner she seemed to find the noise of my thongs upsetting and immediately found a replacement for them. Almost the same but they had a band going around the back of the heel that held them from flipping off with each step. Another movie, then the awkward thing of me having my apron untied, just like before, but this time she ran her hand right up my legs and almost touched what was under my shorts... er... whatever. In the car on the way home she handed me an envelope with a smile and thanks for being so nice. She was really nice all the way home. However when I got out I realized that I was standing in the street in a rather unisex top but definitely what anyone would construe as a skirt and definitely foot ware that would match for sure! I was glad it was dark and ran as fast as I could to the safety of my room. The $20 bill was not what I was interested in at all; it was crawling into bed in my new panties! I don't know why but the first night in the large nylon panties really felt wonderful and by Wednesday night I was even thinking of maybe finding some way to buy some of my own so I did not have to wash them out each day. And then maybe I could also wear them to work and think of her even more that I did now. Saturday when I arrived my boss told me I was to work at something else today and put me in a cab instead! All was fine until we pulled up in front of her house. I knew she would not be happy with my jeans, etc., but also I had not brought the things back I had at my place. Boy was I right on! Before I got to the front door she confronted me. "I need some things done around here on Saturday's so I made arrangements for you to work here, but not like this." Before I knew it we were in her car and headed for my place! She told me to get out and be back in 5 minutes or less in something suitable or look for another job! The only thing I knew she would find suitable for sure was soon on and I was running back down to the street. I was almost crying, as she looked me over before opening the door for me to get in. Just as I sat the snaps all popped and I was sitting there trying to pull the material down over my panties. In the garage she made me come around to her side so she could do me up "properly" and as we walked into the house my shorts had changed into a skirt again! This time she picked out an apron, not only tying it in back but also then to my horror taking the extra material around the front and pulling it up until a bib covered the front of my shirt being tied at the back of my neck. It also had a pocket, much bigger and not only lace around the sides but over the whole front of the pocket also! And that matched the small ribbon of it that also went around the edges all the way around and the bid too! That wasn't the worst of it though! It only came about 3/4 of the way around leaving no doubt at all what I had on under the apron! She said very little all day and by dinnertime I was more than a little anxious about what lay ahead. She helped get things ready and then sat down with some papers and for the rest of the meal she read and I handled the chores. Same with cleaning up and by the time I was finished she had disappeared upstairs. I hung around for a bit trying to be quiet and then trying to get my apron undone but to no avail. Then I quietly turned the TV on and gingerly sat down to watch it. It was only a few minutes before she came down the stairs. "Nothing to do hon! Well I can send you home if you like or maybe we can find you something to do besides wasting your time with television. Which do you prefer sweetie?" Her tone was pleasant and it was the first time I had heard her call me sweetie and I had nothing to do at home but curl up in my bed and think of being here with her so I forced myself to say it before she could make up my mind for me. "No, I mean that is, if you want me to do something I can do it! I just didn't know what to do, that was all!" The whine in my voice said more than the words did and I hung my head and looked down realizing how it must have sounded. "Okay if you say so sweetie. Follow me please." Her grin was huge as she turned and headed up the stairs with me behind her. At the top of the stairs she opened the door on the left and stood aside as I was ushered into her bedroom! Well really not a bedroom but two large rooms with the large double bed in the first with TV and entertainment stuff to go with it. The second was rather dark and in between was a vanity and large mirror, with lights all the way around it, and across from that were two large sliding glass doors that opened revealing a huge closet. From this she retrieved two pair of leather boots, one maybe just below knee high and the other meant to go up well over the knee! In fact it looked like it would reach to her hips if that were possible. She handed them to me along with a shine kit and without a word ushered me back out the door, down the stairs and to the laundry room where she closed the door behind us! Not a word had been said but I knew what she wanted me to do so I started to get the stuff out of the kit. "You cannot wear that outfit to do my boots hon! You will be a mess and your nice clothes will be even more of a mess. Turn around so I can untie you and then you can change into something that can go in the garbage after." I was untied, my apron hung on a hook, then she dropped an item of black on the washing machine, telling to get everything off and use this to do the boots in before leaving. I gingerly picked up the item realizing right away it was an old pair of cotton panties that when on more that covered my hips and lower stomach. In fact they must have been two or three sizes too big for me and I wondered whom they had belonged too, certainly not her size at all! Bye the time I was finished I had black marks all over not only my arms but my upper legs as well. My hands were a mess even after I washed them as best I could. She was waiting in the kitchen and I handed the boots to her and then realized how I must look standing there in nothing but woman's black panties!!!!! "Very nice job sweetie, they look just like new but you look like you need a good scrubbing in a hot tub. Now do you want to go home or go upstairs and climb into a nice hot bath and get cleaned up all nice?" She was all smiles, I just stood there and shrugged my shoulders, not knowing what to say. Without a word she got up and headed towards the stairs and I just followed along. At the top she dropped the boots and then led me down to the second door on the left where a big tub full of water was waiting. "I'll call you when it is time to get out dear, have a nice soak and get yourself all nice and clean for me." With that she was gone and I was left to pull down the undies that I could not believe I had worn to do her boots and climb into the tub. I was almost dozing off when she opened the door and just walked in!! Picking up a bottle from the closet she dumped some fluid into my bath, told me to wait 5 minutes and then get out and get dried off. It was an odd smell, sort of sweet and strong at the same time and as I dried myself off most of the little hair I had on my legs seemed to come off into the towel! With that in mind I gently ran the towel over my groin area and that started to come away also! Stopping that before it was all off I waited for the rest to dry without a towel and then stepped into the bathrobe she had left for me. I just got out the door and she was waiting just outside the room with the bed and dresser in it where the stuff was still on the bed. "If you want to go home I will call a cab for you and you can get dressed now. If not you can stay here tonight and we can have a nice quite day tomorrow. I will be back in a bit and I will know your answer by what you have found to wear." She had a big grin as she closed the door and I was left with decisions. If I put on my things I would be going home and she might be pissed after the outburst earlier. If I put on a clean pair of shorts and top maybe she would take that as me wanting to go home but still anxious to please her. And then the third choice, if I found something to wear for pyjamas she would know for sure what my intentions were. In the bottom drawer I found the nightwear but not what I hoped would be there! Most of them were what girls wore, I don't know, maybe for show, or something where a little satin or nylon was called for. There were only a couple that were close to being reasonable and the best was a nightshirt that came down to just over my knees. It was light blue but the problem was it had a yellow pooh bear over the pocket on the chest. It was the best I could do under the circumstances and just as I got it on she knocked and then quickly opened the door. "I see. Looks like it fits you honey, turn around and let me see. Yes, yes it does but honey you need some under things to go with it. Find something that will do and I will be downstairs." Every pair of underwear I tried showed through the material and I knew I need something close to the blue of my night... wear. In the drawer I found a pair that were close but had see through lace sewn in to connect the back panel to the front panel! Not only where they panties but nylon, lace panties, girl's panties and that was all the choice I had! As I sat in the chair opposite her I wondered if she could tell what I had on under my nightwear. And then it truly dawned on me that not only did I have girl's lace panties on but also a girl's nightie to go with it and if I wanted to stay this is the way she wanted me! For the first time I let myself think about how odd this all had turned out! It was a bit too much and I concentrated on the movie even more. Shortly after 10:00 she had me brush my teeth and get ready for bed and within just a few minutes I found myself in the room with her closing the door and saying goodnight. I put the stuff from the bed back into the dresser and then sat and wondered what had happened to me over the last few weeks. It was mid September and I was in panties and I nightie and I had put them on willingly! A month ago I had plans of getting close to her and it had not gone as planned at all! I was close but it was getting out of control. If this kept up I could see myself sitting in her living room in a pretty dress, all ribbons and bows and that were just not in the cards. There was something odd about her for sure and I was scared for the first time. Quickly I changed into my own clothes, quietly opened the door and tip toed down the stairs and out the laundry room door. I felt much better as I walked all the way home; it was over two hours before I got there. I was scared to go to work the next week but nothing was said and I tried to do her office last so as to make sure she was gone by then. For a few days I resisted wearing anything to bed but I soon could think of nothing else and each night I donned the panties and each morning I washed them out, hung them to dry and then even started wearing them to work. Saturday I booked off sick so as not to take a chance of seeing her and by the following week I felt safe again. I started even wearing the shorts and top during the day in the safety of my own place. But as the days turned to October I thought about her more and more. How was she, was she mad at me, had she had enough of the silly game we had played, maybe we could start over? It wasn't until about 2 weeks later I happened to run into her just as I came in the back of the building. I had never seen her there before! "Well, if it isn't my little friend Bobby! I believe you have some things of mine that you didn't return. Did you wish me to give an itemized list to Dave and have him take it off your check?" I almost fell over! If Dave found out I had shorts and a top of hers was one thing but panties! It would be all over the building in a day and I would never be able to face anyone again. "No please! Don't do that, I will return them tomorrow!" "You probably have them worn out by now and I would just have to throw them away. No you owe me for them, you took them and you wore them, they are yours now. I want to be paid for them and one way or another I will get paid!" "Okay, okay, sure thing, how about you tell me how much they are worth and I will give you the money when I get paid." "I will tell you what they are worth! I am giving a Halloween party in two weeks on Saturday night. I need some help with the food and things and you can work it off by doing that for me. I expect you at noon, I will make arrangements with Dave and it is your choice now. Either do my party or have Dave take it off your check!" For the two weeks I worried day and night and by that Saturday I was fit to be tied. I found solace in lying in bed in nothing but panties and thinking about what it might have been if I had been born a girl. I would never be in this mess and I would probably still be in school and maybe even happy there and doing well. I tried to stay away from Dave as much as possible and really kept to myself as much as possible. However my rent had been jacked up because there was now a waiting list to get rooms in my building as it was just across the street from the university and this was the time of year the landlord really gouged his tenants. I was behind and getting further behind each week, I needed money! When I rang her doorbell at noon I was shaking in my shoes. But when she answered it was all smiles and even more it was like she was a different person. "Well hello dear, nice to see you again, come on in, how about some lunch? How have you been? You are looking good these days, I am glad to have you come back and see me!" It was only a matter of minutes and I felt like we had first met! No hint of anything wrong between us had ever happened at all. We were sitting have a nice lunch as if this was our first meeting. After that we went out to the patio to sit and talk, as it was a nice day for late October. By mid afternoon I was getting nervous, as I was sure she had work for me to do and this was not getting it done! "Uh... did you have anything you wanted me to be doing... uh... Tess!" I had to almost spit out her name as I realized for the first time I had used it in addressing her. She just waved her hand and said it could wait till later. After a light dinner she went upstairs to 'do some things' and I kind of cleaned up somewhat. I noticed that everything was spic and span, squeaky clean as if it had just been done over by someone with lots of experience. I had just sat down when she reappeared and my mouth fell open for sure! Hair down, on her shoulders, a deep, shiny black! Red lips, really dark eyes and the outfit! A white blouse type top with rows and rows of ruffles, covered by a type of jacket, black without sleeves, a sort of tunic going down to just over a black pair of shorts that seemed far too big, all puffed out. And then the boots, those tall, black ones that I remembered from my polishing duty the last time I was here! From the top of the boots to the bottom of the shorts was about 2" of bare skin, white and in sharp contrast to everything above and below! She was all decked out in a sharp contrast of black and white except for the movement of her red mouth as the lips moved with each word! "Well what do you think of my costume? Do you think I look okay?" All I could do was mumble some "wow's", and some "oh's and ah's" as I just sat there with my jaw unable to form anything coherent! "I hope you like it because I have one for you also, it fits right into the theme I had in mind for you and me. I have it all laid out for you upstairs but first you need to get into the tub and get all squeaky clean for me. Then we can get you ready for the party!" "But I thought, I mean I just assumed I would be working, like maybe in the kitchen, I didn't know you meant for me to be really at the party!" "By all means dear, I have every intention of you being a big part of this party, I plan on you and I being a big hit together, now hurry upstairs and get into the tub for me please." I had just gotten settled in the bubbles when she was again standing over me. First she dumped some more stuff into the water and then she bent over and pushed something into my mouth before I could sit up and stop her! "Just something to make sure you have a nice fresh mouth to go with the rest of you when we are all finished getting you ready for the party." It kind of fizzed in my mouth and then it was gone. Just laying there seemed so peaceful and I had to really try to be able to pull myself up and get myself dry! Each time I bent to pull the towel over my legs and torso things seemed so slow, I felt a bit dizzy for some reason. I didn't realize until after I had wiped my groin that it was now completely devoid of hair! My legs and arms were the same way! What little I had had was now completely gone! But then the door opened again and she was back in before I could cover up completely! "Hurry my sweet, our guests will be here soon and we have so much to do with you! Put this on and you won't feel so shy while we get you into your outfit." It was kind of a black thong undergarment with one of the panels somewhat there but the other just a thin sliver of material! I went to put it on but fumbled as I bent over, she took it from me, had me sit on the toilet and she pulled it over my feet and up to my knees as I was somewhat unsteady? She then pulled me up and I pulled it the rest of the way up myself. Things seemed to be going so slow and her voice seemed to be at a distance somehow as she led me across the hall to a room I had never been in before. A large white bed with a canopy all in ruffles and lace and two dressers and a vanity with a large mirror beside the bed all lit up. She took the wet towel and sat me down on the bed. I watched her pull something out of the drawer beside the bed and place it over my eyes and then fit it behind my ears like a pair of glasses! Not only could I not see a thing, my mind was still trying to keep up with great difficulty! "I want you to be a good boy, nice and quiet for me while I get you ready. When I am done with you we will fix your mask so you can see and we will be ready to go down and great my guests." My hands had gone up to the mask but she had firmly taken them and pushed them down again, I had to think about what to do and by that time she had me on the move again. This time I was standing and she was draping something around my front and then doing it up in the back. Then she tightened that up a lot, telling me to breathe in as she tightened it. Something went on over my head and fell down over what she had just put on me. My mind was wandering off and on what she was doing and I just let things go after a bit and waited for her to finish. It was too hard to concentrate. After more and more things were added she started pulling something on over my feet and I hoped they were boots like hers but I knew it was not leather, something softer like socks, but they came all the way up my legs and she fixed them to something hanging down! Then she brushed out my hair, affixed something to it also, then something around my neck, snug and snapped shut in back. Then a glove of some sort on each hand, and then the piece of the mask just over each eye was removed and I was starting at her smile! "Very nice sweetheart, very nice for sure! Just a bit more here and there and you will be perfect." She did something with each eye that seemed to make them heavier somehow and then made me close each one while she put something on each! Finally she lifted each foot and put footwear of some kind on each foot. Then she helped me stand up! I lost my balance and she was quick to hold me steady! "You will get used to them in a few minutes, until then I will help you, now come with me!" The thing around my neck kind of kept my head looking straight ahead and the difficultly walking was all I could deal with but she was definitely shorter than she had been for some reason. We walked down the hall and into her room and right in front of the full-length mirror that was all lit up!!!!!!!!!!!! All I could do was gasp! She was still in her costume but the one beside her was all decked out in a frilly white bid apron, matching cap, gloves and as I kept looking a black and white short uniform with the short skirt held way out with billows of white lacy stuff!!!!!! And the legs from there down were black going into black shoes that fit the outfit but were something I had never even thought of ever wearing! Heels, high heels and dainty ones too! All straps and no wonder I couldn't walk very well, I was 3 or 4 inches taller!!!!!!! MY MIND WAS SPINNING!!!!!!!! "Why." It was all I could think to say! "I am going as a French nobleman from the court of Louis XIV and you have to be in character too so I needed you in something French to accompany me. I also needed help for the party, I decided a maid was appropriate, and voila, a French maid was obviously the only answer. That is your job this evening, no one will know, we all will be wearing masks and if you mind your manners and try to conduct yourself accordingly no one will ever know. If you make a fuss someone might figure it out. Now let's go, the first guests should be coming!" I was surely in a daze as she led me down the stairs but I started to do some clear thinking by the time we got to the bottom. I could feel the cool air on my bare bum! "I... er... well... I don't have anything on, something to cover my up underneath that is. I need some under things don't I?" "I tell you what princess, you walk for me over to that wall and back like a good girl would and then we can see about getting you some panties if you really feel you need them!" Her tone had changed again, she was smiling a bit but that note of irritability had come back into it. On the way over I just tried to balance but on the way back I started to think how a girl might walk in this get up and tried to copy that. "You walk like a someone who has never been in heels so you practise for a while going back and forth and then if you can show some improvement we can find you something nice to go with your uniform. Girls take small steps and let their hips move better, keep your knees and back straight, at the same time and your head up!" It took some time but with a little coaxing she seemed to be a bit happier and I was relieved to be able to get something to cover myself up better. As I watched myself walk in the mirror the idea of my outfit coming just down to the tops of the stockings and with each step bare skin I knew underwear was needed at any cost. I was here for the evening, the mask made it seem tolerable but the absence of underwear was a scary thought! "Now what was it you wanted princess?" "I wanted, wondered if I might get something to wear underneath?" "You mean under your dress?" "Yes... maam." "From now on I want you to say exactly what you would like, for instance something underneath is too vague. What and underneath what is much better, and start each sentence with may I and end with my name please." "I... er... may I have some... under... I mean underpants to wear under my... costume... er... Tess?" "Try it again, and PANTIES are what is worn under a DRESS and try MISS with my name also!" "May I have some pa... panties to wear under my... dress... Miss Tess?" "Much better princess, much better! This party will be better than I had thought! That sounds more like my maid, now run upstairs; there is a pair in the room where you got dressed on the bed waiting for you. Take that thong thing off also!" Now wishing for something and getting it can be two different things! They were there all right but?????????? But white lace satin and ruffles all over!!!!!!! Maybe a bit too big because when I walked in front of the mirror they peaked out with each step!!! Not knowing what to do I was caught with her voice telling me to hurry! Also getting the thong off took some doing, I had to undo the clasps that held up my stockings and then redo them once it was off. With the panties happily in place I rushed as best I could back downstairs. Standing just inside the front door she was waiting with something in her hand and a big grin! "You stand still!" With a bit of coaxing and one hand on the back of my head she slowly put some sweet smelling stuff on my mouth, and then a sprit of perfume from another bottle and she finally let me go. The first time I got a chance I checked in a mirror just to confirm what I already knew, my mouth was a not as red as hers but close! The party was only about 8 or 9 guests, mostly couples and all in elaborate costumes and thank god masks. In a very short time I was cut loose and found myself busy with trays and drinks and fetching things to and from the kitchen. Also my head seemed to clear more and more and with that my fear level rose more and more! Rather than have any chance of someone finding out I made a determined effort to walk as properly as possible, act as properly as I thought a maid might do and be so courteous and polite no one would suspect that I was anything but what I looked like. Now she had been calling me Robert and I had never liked that name but the first time I brought some things a small group she was in she smiled and thanked me with what sounded funny. "Thank you Borbby?" It sounded like Bobby but with an "r" added in there and when she said it rather quickly it didn't really hit me until I ran it over in my mind a couple of times! Anyone hearing it for the first time would and could hear it as "Barbie"!!!!!!!! In fact the next time she said it there was no doubt at all, it was "Barbie" for sure and when I thought about it maybe it was for the best anyway, in light of how I was dressed and how I was acting. By the time it was winding down around midnight my feet were sore but it was obvious to me that I had not been found out. No one had paid much heed to me and as time progressed I became more and more relaxed. With the last guest gone she turned to me with a big smile and a hug. "Very nice job, Barbie! You did a wonderful job indeed." And for some reason I played along as it seemed the right thing in some odd way and took the sides of my dress and apron, looked down for a second, then quickly bent my knees, and with a quick bob. "Thank you Miss Tess!" I don't know why but it just seemed to be somehow appropriate in keeping with the scene. And then she just gushed!!!!!!!!!!!!!! "Well now, wasn't that sweet! You know my little maid, I feel like a nice hot bath. How about going to my room and getting it started for me like a good girl!" It was like we had started a little game but one that had started hours ago and was now maybe all worth it! What was she up to? Was she going to let me be there when she was in the bath? Was???????????????? My hands were wet as I filled the tub and got my bearings in the large room adjacent to the one with her bed in it. A double sink, shower, large Jacuzzi type bath, two huge mirror covered doors, a cubicle with a toilet and all with a plush off white carpet! I had never seen something like this before! She disrobed down to her bra and panties as I stood in disbelief! Then asked me to fetch a towel from the hall closet and was safely in the bubbles when I returned. She had me pick up her things, hang up the costume and then deposit her under things in a hamper by the closet. She had me tidy up some other things as well and then all of a sudden she was up and out with a towel wrapped around her! Sitting on the vanity stool she looked at me in the mirror with a big smile. "Come here dear, here, my hair needs some brushing before going to bed. It has been a long time since I had someone do it for me. You don't mind, do you?" A fancy hairbrush was waving in the air, which I had to take and all t