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Poor Baby

by sissyboi997

Poor Baby

I had been toying with lingerie for years. I started in the usual manner, and borrowed my mothers panties and slips from the hamper, then progressed to going through her things. I moved on to going through the drawers and hampers of my friends mothers and sisters, and quietly amassed a small cache of pretties, which I would then get paranoid about, and dispose of, before starting all over again. Such is my story up until I left home. I wasnt what you would call college material, as I was only an average student. My only saving grace was the fact that I would read anything I got my hands on. I would read medical journals at the doctors office, flying magazines, watch collector magazines, literally anything I could read, I read. This got me a good job, in spite of no college education I had moved in with an aunt and uncle and their 13 year old daughter, Sue. They lived in a larger city, to help make the job search easier. I had gone on dozens of interviews with no success, until that fateful Monday.
The pickings in the classified were thin, and I was desperate. I answered an ad for a sales associate at a jewelry store in an upscale shopping arcade without a lot of hope, and set an appointment for Thursday morning for an interview with Mr. William, the store owner. I mean, hey, who would hire a short, skinny 20 year old, who has never sold anything to anyone, to sell multi-thousand dollar Rolex watches to snobs? But, since I had nothing to lose, and the interview cost me nothing but time, what the heck! In the next few days, I got my longish hair trimmed, polished my shoes, and trimmed my neglected nails. On Thursday morning, I put on my only suit, and set out for my interview. I arrived at the shop a few minutes before my interview, and took a moment to look around. This was not only the classiest jewelry store I had ever been in, it was by far the classiest store period. Soft carpet, classical music on hidden speakers, leather club chairs scattered around in little groupings, and case after case of stunning watches, rings, necklaces, and gems filled the store. I had only been there for a few seconds when a tall, elegantly dressed man walked up to me and asked if he could help. He was wearing a tweed jacket, grey wool slacks, a white oxford shirt, and a dark grey wool tie. He had the look of a wealthy English country gentleman. I told him that my name was Matt, and that I was here about the position that was open. He cocked his head, and looked me over, from my shoe soles to the top of my head, and then held out his hand. œMy name is William, he said. œI spoke with you on the phone this morning. Why dont we step back into my office and chat a bit. His hand shake was not what I was expecting. While not limp, it was not the hearty handshake I was ready for. I followed him back to his office, which could only be described as Victorian, fussy, and a bit on the feminine side, I suppose. Still, what the heck did I know about style? He waved me into a wingback chair done in a flowered fabric, and sat down in a matching chair, set at a 90 degree angle from mine. Just as he sat down, he pushed a button on his large desk, and then asked me if I would like a coffee or maybe an espresso. I told him an espresso would be nice. His door opened, and a good looking lady looked in. I had time to notice that she was wearing a short dress of dark blue silk or satin, a pair of very high heels, and two very pretty legs and a mass of long brunette hair. œTwo Espressos, please, Linda, he told her, "and then no calls for a little while, so I can talk to this young man about a position." He looked at me, œLinda was just like you starting out, not very knowledgeable about the business, and now shes my right hand here at the store. A few minutes later, I was sitting with a delicate demitasse cup of wonderful espresso, talking to the owner of the store, and here was where my voracious reading paid off. He asked me if I knew anything at all about the jewelry business. I told him that I knew a little from reading. He then asked me a series of questions, such as what is the difference between cultured pearls and natural, what are the grades and colors of diamonds, which watch companies made their own movements, and who bought movements from other companies, what is a jeweled movement, and so on. I did pretty well on the diamonds, the pearls were so-so, but since I lusted after a nice watch, I had read everything I could about them, in books, magazines, and of course, on the internet. œWell, well, he said, leaning back in his chair, œYou not only know a lot about watches, but you show a great interest and passion in them as well! I think that with a little on-the-job training, and a bit of book work, you would make an ideal sales associate. There is, however, the matter of dress. œThank you sir, I said, kind of stunned, œI promise that I would work very hard, and since I am living with relatives, I can use my first few paychecks to buy some nicer things, you know, more in keeping with the stores atmosphere. Here he stopped me and told me that if wanted to work there, I needed to start dressing properly on the first day. He thought a moment, and then surprised the heck out of me. He told me that I would start on the next Monday, and that between now and then, I was to go to the mens store at the end of the arcade, and they would take care of my wardrobe. I could pay him back for the clothes a little each week. He then mentioned a salary that was at least double my wildest dreams for a sales clerk! We shook hands, and again I got the not-quite-a-manly-man handshake, and I practically ran down the arcade to the mens wear store. The next two months flew by in a hurry. I found that I was a natural, and in spite of my young age, the customers seemed to think of me as an expert in the field of high-end watches and writing instruments. The ladies seemed to think I was just too cute for words, and I found that I could suggest a piece of jewelry that was twice the price of what they said they were looking for, and 3 times out of 5, they would buy it! I was in heaven, and William seemed to think I could do no wrong. By the end of my 6th month I had rented a very nice little bungalow just a little ways off from the arcade, had a nice wardrobe, and by the end of the first year I had at least a dozen steady customers who would only buy from me, and respected my choices in all sorts of jewelry and gift items. I was also buying a few œspecial items for myself from the internet, and an occasional foray into some of the other shops in the arcade. What was I buying? What a silly question! Lingerie, of course! I now had a dozen pairs of beautiful, soft, silky panties, two absolutely gorgeous night gowns, 4 pairs of shoes, a wonderful, ultra frilly œtraining bra and panty set that from Christines of England that I found on the internet and just had to have. I had also started to narrow down the type of lingerie that turned me on. While teddies, corsets, and night gowns were wonderful, I discovered that it was the little girly, ultra feminine, and very frilly satin garments that got me hard as a rock, and made me daydream about getting home and changing into my other self. Pale yellow, pink, lilac, and ivory satin filled the drawers and closets in my second bedroom, and I loved it! I was standing there on my usual Wednesday off (Saturday was too busy to even think of taking off!), when I looked around and made my next decision. I slipped off the pale blue negligee that I was wearing, and reluctantly removed the marabou trimmed mules from my feet, and slipped into my boy clothes (of course with satin panties on underneath!), and headed for a discount furniture store on the other side of town. I had bought a lot of my stuff here, along with a lot of nice used things, so I knew what they sold, and how reasonable the prices were. Right away I found what I wanted, although I saw a piece of furniture that sort of caught my attention, and made me think in a new direction. More about that, later. And so, with a quick signing of the credit form, I left for home, with the promise that on the following Wednesday, my new bedroom... no, not mine. œLets see, I thought, œThe name has to be just right, girly, soft, and innocent. Hmmm. Heather seamed like a dancers name, or some rich bitch. Kelly was too ambiguous, could be boy or girl. Jennifer might work, so might Karen, or Lisa, or Rachel...I had it! The name just jumped out at me. Chrissie was the first girl I had a crush on (She was he older sister of my best friend, and hers were the first panties I stole outside of family). So, I was going to decorate Christinas, or Chrissies bedroom. Anyway, only a week from now, a white canopy bed, with matching dresser, nightstand, make-up table, and mirror would be delivered to Chrissies room. I hit the internet as soon as I got home, and found a white and pink satin comforter trimmed in lace, along with some pink chiffon material to drape from the canopy. A trip to my local big box store netted me an inexpensive rug with pink and pale green roses, perfect for a little girls room. The following Wednesday evening found me standing in a perfect little girls room, with a few stuffed animals, a few Barbie dolls, a unicorn lamp (courtesy of the Good Will store) and a lovely ballerina poster on the wall. I stood there in a little pink baby doll nightie, clutching a stuffed bear, and almost cried. I knew something right away. I liked feeling like this, and when I though about the piece of furniture in the store that caught my eye, I knew also that I had to have a similar piece, and a few goodies that went along with it. I checked my new credit card, found I had a large credit limit, and went online with a plan. That night as I crawled into the smooth, cool satin sheets, wearing Chrissies nightie, I felt totally at peace, and knew this was the real me. However, it seems there were a few things I didnt know! Lets see, how naive and simple was I? The answer to that, dear reader, is very naive and very simple! Why did I get a job I was unqualified for, with much higher than average pay? Why the assistance with a wardrobe, and at what I found to be a deep discount? Mr. William was the answer, although I didnt know it yet. He was the one who œfound this bungalow for me to rent, again, for much less than I thought it would be a month. He is the one who told me about the furniture store, and œlent me a computer that was excess to store needs to use at home. Now, I found this all to be rather convenient, but who am I to look a gift horse in the mouth? I shoulda checked that nags dental work Ill begin with the part of the story I didnt find out until later, when it was a bit too late. Mr. Williams had called my aunt back (curse caller ID!) later on that Monday, and explained who he was. The problem here is that my aunt is quite friendly and uncomplicated, and will gladly babble about family secrets to perfect strangers if they show any interest. He and my aunt talked for quite a while, and she, of course, gave him more background than I would have liked, including the fact that I was short, skinny, quiet, didnt go out for sports, and was almost more like a niece than a nephew, as I helped out around the house, just like my younger cousin, Sue. In fact, she told him in a conspiratorial way, she was pretty sure that I had worn my Moms panties a few times as a youngster, which she thought was quite funny, as she thought I would make a prettier girl than Sue! Thus began the stalk. The bungalow? Mr. William owned it. The furniture store was owned by guess who, which explained the fact that most of the pieces I seemed to want were on clearance exactly when I wanted them. He also knew exactly which pieces of furniture I bought. Do you think thats creepy? Hang on to your bloomers, if you think thats the creepiest! Remember that computer he œlent me? Ill give you three guesses (and the first two dont count!) who put spyware into my computer, and knew exactly what sites I was frequenting, and what items I had ordered. So all the time I spent on sites such as Fictionmania, Storysite, and the most excellent Sissy Kiss was being monitored by my boss. Now that is beyond creepy! Fast forward about three weeks. That special piece of furniture arrived, and several packages from places like Protex, and Big Baby Fashions, and well, you get the picture. The furniture? Of course it was an adult size baby crib! It was beautiful! It was white with pink flowers, and the rails on one side went down, just like in a real crib, and there was even a locking top cover, should I choose to use it. Strong, sturdy, yet oh so delicate is the only way I can describe my new crib. A thick, soft pad, covered in a waterproof fabric completed the crib, and I was in heaven! I couldnt decide what to do first, so I decided to calm down, and take a bath. I had taken to trimming the hair around my crotch, and now, for the first time, I decided that I needed to be completely hairless. It took depilatory cream, three razors, scissors, and about 2 hours to accomplish the task. After that came a long, hot bubble bath with perfumed bath oil, and three or four glasses of wine to calm my nerves. After drying off, I pulled on an ivory satin dressing gown, and made my way back to Chrissies bedroom. I opened the correct drawer, and just stared at the pile of pure white cloth diapers, the little box of pink diaper pins, and the neat pile of yellow, pink, and white plastic panties. I selected a diaper and a pair of the pink plastic panties, and laid them on the bed. Next, I opened another drawer, and selected a pair of pink satin panties designed to go over the plastic ones. These had gobs of lace on the bottom and around the leg openings. A pair of white nylon ankle socks with stiff lace tops, and an adorable pink satin baby dress with lashings of lace went on the bed next to the diapers and diaper covers. I was shaking all over as I let the dressing gown slide from my shoulders, and lay down on the bed. I gathered the diaper up around my bottom, and snugly pinned myself in. I noticed that they were very thick, as the ad said they would be. I had ordered ones with an extra œsoaker pad which made them extra thick between my legs. I slowly slid the crinkly plastic panties up my now smooth legs, and settled them into place with a sigh. The socks and satin panties came next, followed quickly by the dress. When I was done dressing, I avoided looking into the mirror until I was completely done. I waddled to the closet, and removed the black patent leather Mary-Janes, and slid my feet into them, and buckled the little strap. I then pulled on the pink lacy bonnet that I had purchased, and popped the NUK size 5 pacifier into my waiting mouth. Only now did I look into the mirror, and when I did, I didnt know whether to laugh or cry! I looked, well not like a baby, but like a twelve year old boy who was dressed up like a baby. I loved it! I decided to log onto the computer, as it was my usual time to check into a few chat rooms. As soon as I opened my home page, I noticed a new e-mail, with the words, œYour Make Such A Cute Sissy! in the subject line. I was stunned, and a bit frightened! I could not remember giving anyone my e-mail address, and thought the subject of my dressing was very private. Maybe it was cookies, or spyware, I thought, and boy was I right! I opened the e-mail, and found out that the sender knew my name, my address, where I worked, and what kind of car I drove. He went on to tell me that he knew of the dresses, and panties, and shoes, and all the other things I had purchased over the net, and if I did not log into a certain chat room by nine oclock that evening (it was almost that time, now!) the news would be all over town by morning! He went on to tell me that I would get a private message from œTrueWolf and I had better answer it promptly, or risk everything! What choice did I have???? A minute or two later, there I was. Diapered, in a pink satin baby dress, complete with bonnet and pacifier (I was so scared, I forgot to take it out!), I logged into the chat room, and within seconds, received a private message from TrueWolf. œHow is the little sissy tonight? He typed. œIm okay, was my meek reply. œLet me tell you a little about yourself, he continued, and then described exactly what I was wearing, and where I was sitting! œYou see, sissy boy, he went on, œI know all about you and your little dressing up games. I thought you might make a suitable candidate for me when we met, but now I know that not only are you suitable, you are perfect! œWeve met?? was all I could type. I was in serious panic mode, and had no idea of who was doing this, or what to do next. œOf course weve met, you stupid sissy! In fact, we will meet again in exactly 7 minutes. You are to turn off the computer, and then go into your living room. You are to unlock your front door, and be kneeling on the carpet, in exactly what you are wearing now. If not, your secret will not be so secret, and I DO have pictures to prove it! By the way, you pathetic little sissy, look up at the œsmoke detector and smile, youre on my little sissy candid camera! I was horrified! I was humiliated! I was caught and in trouble, and could only do as directed. 7 minutes later, I was kneeling in my baby sissy finery, and a fat manila envelope came sailing though the mail slot. A voice from outside the door told me to open the package, and follow the written directions, and I had darn well better be quick. Even through the door, the whispering voice sounded disturbingly familiar. I opened the envelope, and out fell a long pink ribbon, a pair of handcuffs, and a note. The note directed me to tie the ribbon to my pacifier, and then tie it behind my head as tightly as possible, and then to cuff my wrists behind my back. I now was kneeling on the floor, completely helpless, and what was a comforting pacifier was now more of a gag than a comfort. Slowly the front door opened, and in walked Mr. William, my boss, and now my new master. He was wearing a pair of jeans, black cowboy boots, and a black silk shirt, and looked even taller from my position on the floor. œWell, well well, he said, almost licking his lips, œI seem to have hired a pathetic sissy baby for a sales clerk! Diapered, wearing a satin dress, and handcuffed, all on his own little initiative! Such a baby girl! What is it you call yourself, girly? Oh yes! Chrissie! He just stood there and gloated, staring at me like a hungry wolf watches a young rabbit . He stepped inside, and closed the door, and told me to not make a sound, and crawl back to my little girly room. Here, as I stayed kneeling on the rug, he explained the whole set up to me.When he finally finished, he told me that he was going to remove my pacifier, and I was only to speak when answering a question, and if I yelled, or did anything unwanted, he would deal with me in a manner most unpleasant. I nodded, and he undid the ribbon, and pulled the pacifier out, placing it on the dressing table. Now he asked me about my history of dressing up, and reluctantly, I told him everything. At his urgings, I even described my favorite panties in great detail. He asked my about my fantasies, and I told him about dressing as a little girl, and now dressing as a baby seemed like fun, and, well... He asked me if I liked girls or boys. I told him that I liked girls, and would never want to be with a man. œThat, my dear little sissy, is about to change! He gleefully told me He took a slim cell phone out of his pocket, dialed a number, and spoke a few words, œGet the chair and bag, and come in. Then he hung up the phone, and left the room. I heard the front door open, close, and then I heard someone lock it. A moment later, he was back in the room with a large leather gym bag, and right behind him was the female sales clerk, and Mr. Williams assistant, Linda! She was carrying what looked like, no what was an oversized babys high chair, and it matched my crib! I had seen it on the web site, and thought that it might be a later purchase! Linda set the chair on the floor, and on command from Mr. William, she helped me into the chair. Once the tray was clicked into place he reached into his bag and pulled out some nylon straps with Velcro, and seconds later my ankles were secured to the chair. Now one side of the handcuffs were removed. Any thought of escape was cut off when the cuff that had been removed from my left hand was locked back to the chair. My left arm was pulled up, and once again there was a dip into the leather bag. This time, he came up with something in pink satin that I could not identify. œHold your hand out, fingers straight, or you will a spanking from Hell, Whispered Linda in my ear. I did as I was told, my mind in a whirl. Things were moving at light speed, and my brain was still in first gear! I could not even begin to comprehend what was going on, and as for thinking of the future, well, that wasnt even possible. My thoughts were centered when a pink mitten was pushed onto my outstretched hand. As it was pushed on, I found I had to curl my hand into a fist inside the thick mitten. Then, a small lock was snapped onto the wrist, and my left hand was now useless. A Velcro strap held my upper arm to the chair, and very quickly my right hand was similarly restrained in a fingerless satin baby mitten. I finally had enough, and started trying to yell and cuss through my pacifier. It really wasnt much of a gag, although it was difficult to pronounce words. Mr. Williams just sighed, and reached back into that horrible bag. He produced a penis-shaped object with some straps and buckles, and without a word, handed it to Linda. He then untied the ribbon holding my pacifier, and I started yelling and cussing. Without a thought, he backhanded me across the face, and then grabbed my nose and held it shut. After I had recovered from the slap, I opened my mouth wide to get a breath, and Linda jammed that short, thick, rubber cock gag into my mouth. Before I could blink, the straps were being tightened behind my head, and all I could do was make gurgling and moaning sounds, as this monster was shoved into the back of my throat, and stretched my lips wide. "Now, my finally quiet little sissy baby, you have two choices. You are about to engage in sex. It can be consensual, or you can be forced. Either way, it WILL happen, he began in a quiet, matter-of-fact voice. œSo your first choice is easy or hard. Your second choice may be a bit easier. Your first sexual experience as a submissive sissy can either be with me, or with Linda. Nod once if you understand your choices. I slowly nodded my head. œGood! Now were getting somewhere! Now look at either myself or Linda and nod, to let us know which one of us gets you first. I looked at Linda, and saw her for the first time that night. Now, she always wore very nice dresses and heels, but they were always high class and conservative. Tonight, though, her heels were very high, maybe 5 inches or more, and were slinky sling-back pumps made in clear plastic with a silver sole and heel. White stockings soared up sexy legs, and ended just below a royal blue satin skirt. I could see the lacy white garter straps connected to these silky creations. On top, she was wearing a sheer white blouse with white satin cuffs and collar, which showed off the white lace bra that was doing nothing to conceal her small but perfect breasts. Her beautiful thick brown hair hung down on her shoulders, and I could smell the faint aroma of an expensive perfume. There was not a moments hesitation as I looked at this luscious creature, this fantasy come true, and nodded my head. œSo, he continued, looking strangely pleased with my choice, Are you going to cooperate, or do we have to force you? Nod once again if you will cooperate. Again, I nodded. Caressing my face, and kissing my cheek, Linda reached her own hand into the bag, withdrew something, and turned. She held up a baby bottle! With words of instruction to not talk, she gently removed the huge gag, and placed the bottle between my lips. I could just get my hands up to hold the bottle, and drank every drop of the apple juice as instructed. Truth be told, I was so parched, I would have anyway! A second bottle replaced the first, and when it was finished, I was released from the chair and placed on the bed. I was now in super thick diapers, and mittens which rendered my hands useless, and otherwise dressed like a baby girl. I was embarrassed, turned on, and scared. The whole time I was drinking the bottles, Mr. William has been taking digital pictures of me, and now he took several of me on the bed. I lay there and watched Linda, as she slowly removed that gossamer blouse. She was wearing a white satin bra with lashings of lace, even the shoulder straps were trimmed in lace! I could see her beautiful, small, and perfectly proportioned breasts rising and falling with each breath. Slowly, she reached behind her and undid the catch and the zipper of her satin skirt, and let it slither to the ground at her feet. I let my eyes slide down her perfect body, past her smooth flat stomach, to the lacy garter belt, and the pair of white satin bridal panties. I was in love! She reached down and began to rub my little cock through the layers of satin, plastic, and cotton, and all the time she was making little cooing sounds. I was hard as a rock, and very soon, I had to pee, very, very badly. The wine I had drunk earlier, along with the apple juice I had just suckled from the bottles had filled my bladder to the bursting point. I struggled to hold it in, and when Linda noticed, she gently pressed on my stomach, and told me to pee my didee like a good little girl. I finally gave in, and released a stream of warm wet pee that filled my diapers, and made me feel good, yet even more embarrassed. At this, Linda reached into the bag yet again, and pulled out a clear vinyl apron, with white lace trim. She put this over her shoulders, and tied it off in the back. Now, she slid a vinyl sheet under my bum, and told me it was time to change little Chrissie. Cooing at me all the time, she slid off the satin diaper covers, the plastic panties, and proceeded to unpin my diaper. All would have been right with the world, except for my boss recording the whole thing on a portable video camera.


Re: Poor Baby - nineprobs

Very good story, but I can't help but feel that it ended abruptly. Bravo!

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