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Family Changes By Karen Elizabeth L. Copyright 1999 May be archived to free sites "You're out of your mind!" I told Sue, my sister, older by two years. "I could never do anything like that and neither would any normal guy!" "It happens all the time," She replied with an indifferent shrug of her shoulders. "You might be surprised to find out just how many guys do it." "Queers and pansies sure," I sneered. "But no normal guy would ever consider dressing up like a woman." "Care to place a little wager on that dear brother?" "Don't be ridiculous," I laughed. "I'd be taking your money. What would you do to win, walk up to a woman and ask if she was a guy?" "Just go ahead and bet me!" Sue challenged. "If I can't prove you wrong and make you admit it we forget the whole thing. Write it off as a dumb joke." "I can live with that," I grinned as I accepted what had to be a sucker bet. There was no normal man in the whole world that would willingly dress as a woman, I was certain of that! "Can you live with losing....." Sue asked, her voice trailing off mysteriously. "You mean?" "Of course I mean....." Sue said in earnest. "Look I'm trying to help you out here and this seems like a really good way to do it. If I win you and Craig agree to move in with me and Amy in California and you get a job as a woman." "But Craig..." I suddenly realized that this bet was not just about me and Sue, I had a sixteen year old son who would be involved too. How could I possibly tell my son that the man he looked up to and respected was going to be wearing women's clothes? Things went into the crapper for my son and I when my wonderful wife Mary died a little more than a year ago. It was totally unexpected and left me so depressed that I let the company I had started go the dogs. I finally sold out, too devastated to care anymore. Craig's grades had plunged also but there seemed little either of us cared to do to help ourselves. Sue had stepped in just in time, Craig was talking about dropping out, and our finances were at an all time low. In a few months I would have to sell the house that meant so much to me when Mary was still alive. I still had Craig's love and respect though, that much I knew. How would losing this bet change all of that though? Why was I letting my foolish pride pull me into such a strange predicament? "I wouldn't worry about Craig if I were you Dave," Sue said with a laugh. "He'll be just fine." "Fine! It might send him over the edge." How could Sue be so callous I wondered. "Craig will be fine, you'll be fine, the whole world will be fine," Sue laughed. "Now are you willing to bet or not?" I shouldn't have done it, I realized that at the instant I accepted the bet but Sue wasn't about to allow me to renege. "Okay, you won't let me back out but you're going to have to go pretty far to win this, I don't plan on just taking your word for it!" I said bitterly. "Far?" Sue laughed. "I don't have to go very far at all. As a matter of fact let's start right here." "Here?" I asked confused. "What's here?" "Not what, who." Sue corrected me. "And who is your dear son Craig, or should I call her Lori?" "What about Craig, and who is Lori?" What in the world was she talking about I wondered? How was she going to win her stupid bet with Craig? "Your son is a perfect example of a normal guy who likes to dress as a girl!" Sue announced triumphantly. "He plays sports in school, acts like any other teenage boy yet he also enjoys spending time as a girl named Lori!" I listened closely as my sister explained that several years ago my wife had accidentally caught Craig wearing one of her nightgowns and a pair of panties. Craig was very upset but Mary took it very calmly and had a long talk with him during which she learned that it wasn't the first time he'd worn her clothes. After hearing the whole story Mary told him that she understood that he felt an overwhelming need to dress up like a girl occasionally and promised never to tell anyone as long as he didn't do anything that might call attention to himself. Mary had been keeping it a secret from me for several years afraid that I wouldn't understand Sue explained. "Understand?" My mind was spinning out of control. "Of course I wouldn't understand, I still don't! Craig has always been a perfectly normal boy, he's on the swim team at school, he loves baseball, and the girls are crazy about him!" "Perfectly normal, you said so yourself, yet he wears girl's clothes." Sue grinned broadly and clapped excitedly. "I win!" "Hold one, one misadjusted kid doesn't mean you win anything. I want real proof. A guy who no one but no one would ever suspect does that sort of thing." I was sure I had her this time, I'd deal with Craig later. "Would John do?" Sue asked calmly. "John, Your fiancee John?" I gasped. It couldn't be! John was practically the ideal man. His boyish good looks made him nearly irresistible to women, his skill with a pool cue or hunting rifle were legendary, and his knowledge of sports rivaled professional commentators. I'd known John since Sue brought him for thanksgiving dinner three years ago. I'd gone hunting, fishing, and skiing with him but I never suspected anything odd. "That's right little brother," Sue squealed in delight. "He can hunt, he can fish, he can do anything any other man can do and do it better yet he can also wear a pretty dress and have men drooling at the sight of him!" "Prove it!" I demanded. "How can I be sure you're not making this all up?" Sue reached into her purse and removed an envelope. Opening it slowly she removed a letter and some pictures which she handed to me. My hands shook as I looked at pictures of John in various stages of dressing and making himself up as a woman. This was my hunting buddy wearing a pair of high cut panties and a matching bra. This was my fishing buddy in a lacy slip attaching nylons to the garter belt he was wearing. Finally here was a man I was proud to know in a short black dress, curly blond hair, perfectly made up, his long nylon clad legs ending in a pair of black heels. "Cute isn't she?" Sue broke my concentration and brought me plummeting back to reality. I picked up the letter and slowly read John's explanation of his dressing and assurance that he'd be there to help me every step off the way as I made the change into a woman. I didn't need to look at Sue to know that she was smiling. She had me beat and she knew it. "When do I have to start?" I asked weakly. "And what about Craig?" "You're not working so I thought it would be best to start right away. You can dress like a woman around the house, it's secluded so no one's going to see you. We'll explain everything to Craig when he gets home from school, I'm sure he'll be thrilled." "Thrilled? With watching his father learn how to be a woman?" "I suppose I should have mentioned it," Sue laughed nervously. "But John and I thought it would be best if Craig stayed behind." "I can't leave him in Minnesota while I'm off in California!" I shouted. "I'm not going anywhere without him!" "When I said that Craig was staying, I should have explained myself better." Sue was avoiding my gaze for some reason and I knew it always meant that she was up to something. "You see Craig is staying but Lori will be coming along." It took a moment or so for the name Lori to register in my mind. "Lori? You can't be serious!" "Yep, that All American boy son of yours is going to become an All American girl! With his pretty blond hair and cute blue eyes he'll be adorable! I felt terrible as I listened to Sue describe her plans for me and Craig. I hadn't been able to recover since Mary had died, every place I looked, every place I went, everything I did reminded me of her. Sue knew that I had to get away if I was ever going to recover. She finally decided that bringing me to California to live with her and her daughter Amy would be just the change I needed. The only problem was that the area she lived in had very few job opportunities, especially for men. The Want Ads were overflowing with Secretarial jobs and other traditionally feminine role jobs because so many of the young women wanted to move into previously male dominated fields. Now the secretarial jobs were paying salaries unheard of in the past simply to attract qualified workers, male or female. Men however considered the jobs as women's work and the women considered them to be beneath them when they too could become executives! The result was that there were no secretaries to assist the executives who were now answering their own phones, and typing their own letters leaving little time to manage the businesses. She knew that I'd never consider becoming a secretary even as a male, since I too would consider it to be a woman's job. My pride would keep from taking a job with a lucrative paycheck and eventually I'd end up as a security guard in some deserted warehouse with little income and less hope. That was when she thought about Craig and remembered his crossdressing. One thought led to another which eventually led to thoughts about John which led her to my current predicament. No one would know me in California and no one knew she had a brother and not a sister, with a little work and some help from John I could become her sister. She knew that even if I initially objected to the idea I was getting more desperate by the day. I couldn't hold out for long so she simply waited for the right time to spring it on me. Her timing couldn't have been better, I was desperately seeking a way out of my depression and her arguments were wearing me down. Everything had been all planned out, all I had to do was agree and my problems would be over. I'd be happier, I'd have a good job with a very good salary, I'd be with my sister and niece both of whom I cared for, and if Sue was telling the truth even Craig would be happy. I sighed deeply. "If Craig agrees to it you have yourself a sister." Sue and I spend the rest of the afternoon talking about what was going to happen and waiting for Craig to return home from school. He seemed happy to see Sue again, I wondered how long it would last. "We have to talk about something Craig," I smiled and motioned for him to sit next to Sue. "How would you like to be able to spend your summer on the beach with Amy?" "That would be great dad!" Craig replied enthusiastically. "A whole summer just hanging out on the beach!" "In a Bikini." Sue added as if an afterthought. She always did have a way of springing little surprises on people but this time I wish she had waited. I wanted to explain everything one step at a time. "Excuse me?" Craig's head swiveled around to see Sue smiling at him. "What did you say Aunt Sue?" "She wants to know if you'd mind wearing a bikini to the beach." I moaned. "You see there's a catch to this little vacation." "Me, wear a bikini?" Craig shot back obviously trying to hide his excitement. "You're kidding right?" "Your mom and I had some interesting conversations over the years Craig," Sue smiled at her verbal checkmate. "Or should I call you Lori? Want to talk about the underwear you keep in the back of the third drawer of your chest of drawers?" "I'm sorry dad, really I am. I don't know why I did it but I'll never ever do it again!" Tears ran down Craig's cheeks in a torrent. "Calm down Craig," I sat next to him and gave him a hug. "Please pay attention and don't interrupt me because I have a lot of things to tell you." I then went on to explain all of what Sue had told me. After I finished explaining everything to Craig he had a very confused look on his face but I could hardly blame him for that, could I? "You're serious aren't you dad? We're really going to move in with Aunt Sue, you're going to be my mother and I'm going to be your daughter?" When I nodded my agreement Craig suddenly threw his arms around me and hugged me tightly. "Dad, that sounds great but I really don't know anything about being a girl. I just played around with some clothes." Sue assured him that by the time summer came he'd be a perfect girl and wouldn't give a thought to even wearing a bikini. The big gin on his face told me that he couldn't wait to get started. We started that day with Sue taking us on a shopping trip to pick up a few outfits. With Sue acting as a wife with her bored husband and son we shopped in several of the local discount stores and a few major department stores until the trunk of my car was jammed with bags containing all sorts of feminine outfits. All sorts that is except for casual clothes, Sue insisted that we wear nothing but dressy outfits until we became comfortable with women's clothes. Only then would we be allowed to switch over to slacks and other casual wear. I went to bed that night wearing a short red nylon nightgown and matching panties. Craig, who loved the idea of wearing skirts and dresses at home insisted on a pale blue cotton nightie that barely came to mid thigh. The straps as well as the hem were trimmed in white lace as were the leg holes on the matching panties. I tossed and turned wondering what had possessed me to do such a crazy thing while Craig fell fast asleep, a contented look on his face. The next morning at breakfast Sue showed up in a very conservative pink nightgown while Craig and I looked like a couple of hookers. Craig didn't seem to mind at all though and was very happy when Sue complimented him on his nightie. He later left for school, a smile on his face, panties and girls socks under his jeans. Sue had a great time picking out clothes for me as I bathed and shaved my legs and underarms. A pair of white nylon panties whit a lace panel extending down the front with a matching bra, half slip, and garter belt were waiting on my bed when I finished. As I threaded the garters down through my panties I thought back to the times when I had watched Mary do it and how erotic I had thought it to be. Why then did it seem like such a silly thing to do now? Numbly I finished pulling down the garters then rolled on the nylons Sue handed me and attached them to the tabs at the end of my garters. "There, don't you feel sexy?" Sue asked. "Just imagine how sexy you'd look in a pretty dress with heels on!" "I don't feel sexy at all," I shrugged. "I still think this is a stupid idea but I don't have any other options right now." "Don't worry your pretty little head about it little sister," Sue giggled. "Soon you'll find yourself looking forward to wearing something sexy under your outfits. It feels wonderful to wear something really frilly and sexy under your outfits. You're the only one who knows what you're wearing and it makes you feel so feminine and naughty!" "I don't see myself ever feeling that way, now could we please get this over with?" I pleaded, wanting to put something on even if it had to be a dress, just so that I wouldn't have to see the extra feminine lingerie I was wearing. "In a bit little sister," Sue teased. "Now be a good girl and hold still for a moment or so." Sue took her time applying some type of gel to my newly shaved chest then produced a pair of very realistic looking fake breasts which she pressed firmly to my chest. "Now hold them tight for about thirty seconds please," She instructed as she reached for the bra to complete my lingerie. Thirty seconds or so later and I had breasts firmly attached to my chest and a bra being fastened around my chest. Finally and to my relief Sue helped me into a black and white striped sweater dress cut in such a way that combined with my new breasts made me look very physically attractive. "What do you think?" Sue asked hopefully. "Still worried about people thinking you're a guy?" "Hell, I'm not even sure that there's guy under all this!" I told her as I stared wide-eyed in amazement at the reflection in the mirror. Except for the short hair even my facial features seemed feminine! "You must have been very sure I'd go along to have had those fake breasts handy," I chided. "What if I had refused?" "I sell for a living remember?" Sue said calmly. "And I'm very good at what I do, you weren't going to refuse. Now sit over here while I do your makeup." I have to admit that I was sort of intrigued as I watched myself being made over. Ever since I was a teenager I was absolutely amazed at the difference a girl could make in her looks with a little bit of makeup and now that difference was happening to me! Sue seemed perfectly at ease with the chore of making me into a pretty woman, she applied liquid to my face then powder to set it, outlined my lips with a lipstick pencil before filling them in with a lighter shade of lipstick, before applying blush, and doing his eyes. As I sat transfixed by my image in the mirror Sue disappeared for a few minutes only to reappear with a shoulder length auburn wig in her hands. She was humming a happy tune as she placed the wig on my head and brushed out the curls to give it a very full look with a loose curl. The change was nothing short of astonishing, if I didn't know who the person in the mirror was you would never have been able to convince me that I was looking at a man! The woman staring at me from the mirror had full lips that begged to be kissed, her smoky brown eyelids and long curly lashed brought out an innocence in her eyes, and her soft fluffy hair cried out to have fingers run through it. She looked soft, innocent, a woman to be cared for, yet she was all me. What do you think of yourself now little sister?" Sue was the type who fished for compliments whenever she did anything and this was not going to be any different. There was no room for doubt, she had done an extraordinary job of making me look like a woman but how in the world could I compliment her for that? "I think you shouldn't let you do this to me Sue," I tried to let her down easily. "It's just not right. I'm a man, a father for heaven's sake, you just can't change that." "Bet me!" Was Sue's challenge. "In just a few more weeks you won't think of yourself as anything other than a single woman and the mother of a teenage daughter. You'll see a pretty woman and compare yourself to her wondering if your butt is a as nice as hers, what you'd look like in the dress she's wearing, and if you should get your hair done like hers." "It's not going to happen Sue, I'll never think of myself as anything other than a man pretending to be a woman." "We'll see," Sue said with a devilish gleam in her eyes. "By the way, we can't call you Steve anymore, from now on your name is Jacquelyn. Now lets get some shoes on and get started with your training." That was the end of it as far as Sue was concerned, she now had a younger sister named Jacki and a niece named Lori. Both her sister and her niece needed a lot of help in their development as women and she was going to see that they got it. I'd go along if only because for some strange reason this was lifting my spirits. Soon I'd be leaving for sunny California, a new job, and a new life as a woman. It wasn't the type of job or life I wanted but I found the idea to be sort of intriguing and that was more than I'd felt about anything since Mary died. I slipped on a pair of low heeled shoes Sue bought for me and allowed her to spray some of her favorite perfume on me. The perfume she said would act as a constant reminder that I was a woman now. No matter what I was doing, preparing dinner, matching a movie, or just relaxing and reading the paper I'd smell the perfume and be instantly reminded of the change that I was undergoing. Sue helped clean up the breakfast dishes but her helpfulness came at a price, the entire time that we worked she called me Jacki and insisted on complimenting me on how pretty I looked. With the dishes out of the way though she instantly moved into high gear and began teaching me how to walk, sit and stand as a woman would. I must have walked the length of the first floor fifty to sixty times with my arms outstretched and parallel to the floor before Sue told me I could stop. Just as I was about to plop down on the sofa and kick off the dreaded heels that were causing my feet to ache Sue insisted that I learn to walk up and down steps in a ladylike manner. Finally after twenty five trips up and down the steps Sue told me to take a break. Exhausted I flopped down on the couch, kicked off my heels and began to rub my feet. "Ladies do not sit like that!" Sue bellowed. "Look at you, your skirt is up to your waist, your slip is showing, and your going to put a run in your nylons if you're not careful! Get up and let's practice your sitting until you can do it like a lady instead of a truck driver in drag!" It took all of my energy to put my heels back on but I somehow managed and after thirty five tries at standing and smoothing out my skirt, sitting and smoothing out my skirt, pulling my skirt down to keep my slip from showing, then crossing my legs like a woman I was finally allowed to gracefully sit down, remove my shoes and gently massage my feet. My relief was brief however and soon it was back to walking and sitting practice until it was time for lunch. Sue freshened up my makeup and wig then hit me with a shot that took my breath away. "Come on Jacki," She laughed. "Let's pick up something for lunch!" A feeling of panic swept over me. "I'm not going out in these clothes, someone's bound to notice." "We'll just go to the drive through, you won't need to get out of the car. I just want you to get a feel for going out this way, you'll have to do it before long." As usual with Sue, the discussion was over before I had a chance to talk and with my heart pounding I was soon following Sue out to the garage thankful that Mary had insisted on a house that stood away from the rest of the world. Two acres of trees separated me from my nearest neighbor and any chance of imminent discovery. It didn't do anything though to calm the fears that escalated as Sue drove away from the house and into traffic. As we drove towards town I tried not to look out the window at the people who smiled at us while we waited at traffic lights. Did I say people? Make that men, nearly every man between the age of 12 and 80 checked us out whenever the chance arose. There was once a time in my life when I did the same thing so I knew what they were thinking, they'd momentarily look at our faces then our chest's and if they were close enough they'd look down to see if we were wearing skirts and check out our legs. If they couldn't see our legs they'd be content to stare at our chests until we drove on. They had to be wondering if we were wearing some type of sexy lingerie under our outfits, possibly a lacy bra, high cut panties, or a garter belt and nylons. I knew what they were thinking, I thought the same things when before Mary died and my mood changed. After that I didn't even care about what a woman had on, I had no fantasies about her at all. Now my problem was that everything these men were fantasizing about my wearing I had on! I was wearing the lacy bra, the sexy high cut panties, even the garter belt and nylons, I was the woman of their horniest fantasies! I was lost in thought when suddenly Sue reached over and pulled my skirt up several inches, exposing more leg than I cared to show. "What are you doing?" I frantically clawed at the hem of my skirt to pull it down only to have Sue slap my hand away. "If you got it flaunt it!" Sue laughed as she held my hand. "Now I can't drive and worry about your being a prude. Either you leave your skirt where I put it and enjoy the attention or I pull over and you can walk the rest of the way!" I knew she wasn't kidding about walking, it was a favorite trick of hers when we were younger to make me walk home when I made her mad. I nodded silently in agreement and left my skirt where she had placed it. We got to my favorite fast food outlet and just as promised Sue went straight to the drive through where she ordered a salad for each of us. "Don't eat too much Jacki," She chuckled. "You have to watch that figure of yours now. In case you're interested you're a perfect size nine the same as me, a great size for finding really great outfits. If I were you I'd try really hard to stay that size." What did she expect me to say to that - thanks for the great advice sis, I'll keep to a strict diet and start exercising? I just gave her a smile to shut her up as I'd done in the past and it seemed to have worked. It seemed to have worked for about five minutes that is. The next thing I knew we were pulling into the parking lot of a supermarket and Sue was turning off the ignition. "You're pretty low on a few things back at the house, no point in having to come back later right?" She asked with an evil grin. I had completely forgotten that Sue hated being ignored and my refusal to thank her for the compliment about my size had struck a nerve and now it was time for revenge! "Please Sue, I can't go in there," I begged and pleaded for sympathy but her eyes had that cold look I had always hated. "I'm really happy that you think I'm a perfect size nine, really I am!" "Too late, Jacki," She said coldly. "But I'll still go easy on you and not make you talk. Other than that there's no chance of your being read." "Read?" "Found out, discovered, whatever you want to call it," She said as she opened the door to leave. "Now either you're coming with me or your wig is, your choice." "Some choice," I muttered under my breath as I slowly opened my door. I was shaking like a leaf as I walked with Sue to the store. The clicking of my heels seemed to broadcast my coming and I was sure that everyone would turn towards the unbelievably loud noise and the woman making it. Then it would happen, a grin would come over someone's face, and then it would turn into a laugh and they'd shout, "Check out that guy wearing a dress!" We passed several people entering and leaving as we walked, some smiled, others passed by without a glance. Only one man passed us and the look on his face made me feel sure that he wasn't going to be the one to expose me. No, the look on his face said that there was nothing he'd like more than to see me exposed! Sue noticed the man's stare and her face lit up. "Smile at him!" She whispered. "He likes what he sees, smile to say thanks for the compliment!" I wasn't stupid enough to ignore Sue twice in such a short time, heaven knows what she would have done if I had so I looked right at the man and smiled as women had done to me when they caught me checking them out. It's impossible to describe the relief I felt when he returned my smile, nodded, and kept walking! "See that wasn't so bad was it?" Sue teased. "He paid you quite a compliment and all you had to do in return was smile at him." "I was terrified and you knew it!" I whispered back. "You're having a good old time setting me up like this aren't you?" "Yes I guess I am," Sue replied indifferently. "But at the same time you're learning some important lessons, you really can pass as a woman, and you're learning how to react to men." "I'm not ready for these kind of lessons yet and you know it!" I argued. "You're pushing me too far, too fast." "Were you ready for that dress?" She teased. "That lingerie?" "You know what I mean," I pleaded. "It's too much!" "If you were wearing a flimsy negligee and getting into bed with a guy I might say it's too much, right now that is. Until then...." By the time I recovered enough to respond we were already walking into the store and I didn't dare open my mouth for fear that my voice would give me away. Sue was amazing in her planning skills, she had drawn the argument out then made an outrageous statement at a time when I couldn't possibly respond to it. I followed her into the store madder than ever, hoping to get revenge yet worried about what would happen if I tried. I quietly followed Sue around the market trying to avoid looking directly at anyone. Sue was taking her sweet old time picking out a half dozen items obviously trying to make me feel as uncomfortable as possible and it was working perfectly, I couldn't wait to get back to the car, pull my skirt up past my knees and generously thank Sue for her compliments on my size and looks! I let out a huge sigh of relief once I closed the car door behind me which caused my dear sister to break into a fit of laughter. "That guy thought you were cute!" She said during a short break from hysterical laughter. "How's it feel to have men lust over you Jacki? Did you enjoy it?" "It felt weird and very scary!" I admitted. "I don't think I care for the way men have been looking at me, it's not right." "Jacki," Sue said in a suddenly serious tone. "I was really surprised at how pretty you looked after I finished with your makeup and everything. I wasn't sure how you were going to turn out but when I saw what a doll you were I knew I just had to get you out of that house. You needed to see yourself as others are seeing you, a very attractive, nicely built woman. You're going to have to get used to men looking at you, believe me they're not going to stop. If you just relax and let me work with you I promise you'll enjoy it." "Work with me? What more do you have to do, you said I looked very attractive already." I asked wondering what she had in mind. She had promised to turn me into a woman but never said how she was going to do it. Maybe now she'd open up. Sue must have felt guilty about our little side trip to the market, she smiled to show she was doing it on her own and then told me she'd explain it all when Craig got home. Back at the house I sat down as gracefully as possible and removed my heels. "God, it feels great to get these off," I groaned. "How and why do women wear these things?" "We get used to them, you'll see. And we wear them because they make us look pretty and sexy and men love them." She explained patiently. "Once you get used to them you'll understand and enjoy the way they make your legs look and get looked at!" I padded around in stocking feet preparing dinner and listening to Sue predict that soon I'd be buying myself pretty shoes to go with every outfit I own and that they'd be even higher heels that I wore today. How could I argue with her? She knew her plans for me far better than I did, all I could do was go along until I could get back on my feet and go back to being a man again. Whether Craig would follow was a question I couldn't answer though. Just before Craig got home Sue insisted that I change into another dress that she had selected for me. Laying out on my bed was a low cut short black dress and lingerie that made what I was wearing seem positively tame! I examined the half cup black lace bra and wispy black lace panties for a few moments then asked Sue to unzip the dress I had on. I carefully stepped out of the dress and my slip then unhooked the nylons from my garters and set them aside. I was about to ask Sue to leave the room when I realized that I might need her help so beaten again I continued changing while Sue carried on a conversation about how cute I looked and what a nice figure I had. I of course thanked her for each and every compliment fearful of ending up outside in only my panties and bra! I slipped out of my panties and into the sheer lace black ones then fastened the garter belt and carefully rolled on a pair of nylons that felt as light as air itself. I did what I could with the bra but Sue ended up showing me again the best way to put on a bra without help, something I thought best to remember since I didn't really think I'd want anyone else around while I put these things on. I stepped into the delicate half slip that matched everything else I wore and adjusted it so that the slit would be on the same side as the one I noticed in the dress I was going to wear. Sue was thrilled that I had taken that little step but it was really something I had picked up from watching Mary dress. I decided not to mention how I knew to do that preferring instead to reap the compliments Sue was lavishing on me. Once I had all of my new lingerie on and properly adjusted I took a deep breath was about to lower the dress over my head when Sue stopped me. "Hold it just a second Jacki," She called out racing for her room. "You need something else to go with that dress." Sue came flying back a few short seconds waving something black that I couldn't quite make out. "Here you go," She cried triumphantly. "Just what that dress cries out for!" "A woman to wear it?" I joked hoping she'd let it pass without problems. "A woman is going to wear it," She snapped as she handed me the garment. "My sister Jacki as a matter of fact. Now put this around your waist and I'll hook you up." Puzzled I put what looked like a girdle without legs with hook closures along the side around my waist and drew my breath in sharply as Sue pulled the sides together and fastened them. "Whhhhat is this?" I gasped, barely able to take a breath. "It's too tight, I can't breathe!" "Don't be such a baby," Sue laughed. "This is a waist cincher, it'll give you the shape you need for that dress. Just calm down, in a few minutes you'll get used to the tightness and adjust your breathing." "In a few minutes I'll be dead!" I gasped as she helped me lower the dress over my head and zipped it up. I had to slip on a pair of black three inch heels which Sue insisted went with the dress before she helped me over to the mirror to redo my makeup. She smoothed cream all over my face then deftly removed every trace of the makeup I wore earlier and quickly added what she called evening makeup to my face. This time the woman in the mirror wasn't just pretty, she was absolutely sexy and alluring! I could feel a familiar but embarrassing stirring in my groin as I stared at a woman that seemed so very desirable. How could I want that woman so badly and yet be her? "Hot isn't she?" Sue giggled guessing what I was thinking. "And that's just her face, it gets better. Want to see?" Between being stunned and the cincher I just couldn't speak so I nodded my head slowly and Sue helped me to my feet and to a full length mirror where one of the most beautiful women I'd ever seen stared out at me! She had everything a man could want in a woman, beautiful curly red hair, a dress that fit like a glove, showed her ample curves, allowed her breasts to peek out daringly from their confines, and showed shapely legs encased in black nylons and sexy heels! "That's you in there Jacki," Sue taunted. "That beautiful, sexy woman in the mirror is my little sister Jacquelyn. She's gorgeous, don't you think?" "Gorgeous," I whispered. "But me?" "All you Jacki dear," Sue whispered back. "This is what you're going to look like when you move in with me. Men will fall all over themselves just to get a smile from those beautiful red lips of yours. You're a woman now Jacki, a beautiful, sexy, desirable woman." She was right, I looked every bit as good as she said and more. A major shock to my already badly bruised male ego, this was going to take a lot of getting used to. I had barely enough time to get used to balancing on the higher heels before Craig walked in the door from school. He looked at me, smiled and said hi, then looked over at Sue. "Hi Aunt Sue," He called cheerfully. "Where's my dad?" Sue acted as if nothing was unusual. "Your dad's gone, Craig." She said very calmly and deliberately. Gesturing towards me she smiled. "I'd like you to meet my sister Jacquelyn, just call her mom though." "Mom?" Craig asked seeming thoroughly confused. Suddenly he turned his attention back to me. "Dad?" "Mom," Sue corrected. "This lovely lady is your mother." "M....mom?" Craig asked as he looked me over from head to toe. "Is that really you?" "Yes it's really me Craig," I smiled. "So quit staring at my breasts like that will you!" Craig immediately returned his gaze to my face. "You're beautiful dad, I can't get over how good you look!" This time I didn't wait for Sue to step in. "Thank you Craig, that's very nice of you but please remember to call me mom okay?" "Uh okay mom," He agreed with a laugh. "But you're still hot!" "Thanks," I said as I slowly walked over to him and took him by the arm. "Now it's time to change you into my daughter Lori. Are you ready?" "I can't wait!" He shouted excitedly. "I just want to look as good as you do okay?" "Trust me Lori," Sue laughed. "You're going to be just as pretty as your mother here, your days as a boy are about to come to an end!" Odd that the same words that terrified me seemed to delight Craig. He couldn't have been more pleased by the idea of being turned into a teenage girl! When Sue mentioned that she had an outfit prepared that she expected him to wear he never protested once, instead he practically ran to his room to see what he was going to wear. I thought he was going to start doing flips and handstands when he saw the outfit Sue had chosen for him. On his bed lay a set of matching lingerie, very pretty but yet appropriate to a girl his age, a pair of white satin panties with lace around the waist and leg openings, white satin bra with a tiny pink rose where the cups joined, and a white half slip with about two inches of lace at the bottom. Even I had to admit that Sue had excellent taste, the lingerie was definitely chosen to make Craig look and feel dainty and feminine without any overt sexiness. Just perfect for Craig's budding womanhood. What really caught his attention though was the pink dress hanging from his closet door. The dress would have set any young girls heart to pounding and it was obvious from his blank stare that it was having the same effect on Craig. The dress was pink lace over some type of pink satin type material with a neckline that was cut high enough to be modest yet low enough to tantalize any boy who might glimpse at the girl in it. Craig turned and threw his arms around Sue. "Aunt Sue, this is so wonderful, you don't know how much this means to me!" "I'm happy to help you Lori," Sue told him. "I just want to see you and your mom smiling and happy again." "I don't know about dad, I mean mom, but I couldn't be happier!" Craig said his eyes beginning to glisten with tears. "I'd be happy if I could just breathe and get out of these heels," I laughed trying to seem happy. "But in any case it's your turn now Lori, so let's get changed and have dinner." Actually I didn't care about whether I had dinner or not, for some odd reason though I couldn't seem to wait to watch my son being transformed into a pretty girl! "Aren't you two going to leave?" Craig asked as Sue and I made ourselves comfortable. "I mean I have to get changed and everything." "So what," Sue shrugged. "We're all girls here. If you can't get used to changing in front of your mother and aunt how will you ever get used to changing in front of Amy this summer?" "Amy knows about this Craig asked as he undid his shirt. "What does she think of the whole idea?" "She was very concerned about the two of you," Sue said as we watched Craig remove his shirt and start on his slacks. "she hopes that this will help and she loves the idea of having a girl cousin to talk to and hang out with." Craig hesitated for a bit when it came to removing his pants with me and Sue there but he finally got the idea that we weren't leaving and slid them down to reveal his pretty white panties. He stood there waiting again until Sue cleared her throat then stepped out of the panties he wore and pulled on the new ones. He sat down on the bed and with an expert skill level rolled up one leg of the pantyhose at a time and carefully pulled them over his hips and straightened the waistband. As he reached for the bra Sue jumped up and stopped him as I was hoping she would. with a flourish she produced a smaller set of fake breasts and a tube of glue. "May I?" I asked taking the breasts and glue from her. Now I'd see just how much fun Craig thought this was going to be. Just wait until I glued these breasts on to his chest, he'd realize that to Sue this wasn't just a game! I smiled inwardly as I stared into eyes and applied a generous amount of glue before placing the breasts against his chest and holding them firmly in place. "Here, let me show you how to put one of these on," I laughed as he picked up the bra he was to wear. I took a lot of pleasure in showing him how to fasten it in front of him, turn it around and set his breasts into it just the way Sue had shown me. I was sure he'd feel as silly and humiliated as I had but instead he was smiling happily. "Thanks mom," He said softly. "I never thought I'd ever be able to dress up with you at home, this is so great! I suppose that I had been hoping that Sue was wrong about Craig and that he'd balk at taking what might have been a little game as far as this. Instead of balking though Craig was happier than he'd been without his mother here, he was having so much fun that I knew I had been wrong. I watched as Craig adjusted his bra straps and stepped into the slip. I could almost hear a sigh of pleasure as he unzipped the dress and slowly slid it over his head. As he reached behind to get the zipper I stepped forward again. "Let me help Lori," I smiled as I pulled the zipper up to where he could reach it and finish zipping himself up. "You're such a beautiful young lady!" I choked back the emotion that was showing in my voice as I felt tears building up in my own eyes. "I'm going to be so proud to have such a lovely girl as my daughter!" "I think you're both very sweet but could you have your mother daughter bonding session after I do her makeup?" Leave it to my sister to ruin what had all the makings of a great Kodak moment! Craig stepped gingerly into the low heeled shoes and followed Sue to my room for his makeover. She reached into a bag she had and brought out a lighter shade of liquid makeup which she blended all over Craig's baby face then brushed on the setting powder and blush. She gently curled his lashes and applied a light pink shade of eye shadow to his lids before doing his lashes again with a coat of mascara. I drifted back to earlier when I had been the one sitting in that chair having my face painted and my lashes curled. Craig looked so angelic sitting there, he seemed to be getting prettier by the moment. what had I been so afraid of when I had been sitting there? What was I so afraid of now? His makeup complete Sue finished Craig off by clipping a fall into his long hair. He really looked cute with long blonde hair I thought to myself, I think I'll insist that he keep it that way. When Sue was done there was no trace of Craig left to be found. He had been completely replaced by a lovely young lady named Lori, my beautiful daughter Lori! He was thrilled with the change as much as Sue and I were, now it was just a matter of changing the actions and thoughts to person. Sue had worked hard on me today and I knew she wouldn't let up until she was sure that I would act like a woman at all times. Somehow seeing Craig all dressed up and looking so happy and pretty it didn't seem quite so scary. All I had to do was to survive I told myself and this is what would help me survive. Later when I was back on my feet and a man again I'd look back at this time in my life and laugh about it! Over dinner Craig and I listened intently as Sue described what her plans were for changing me into a secretary and Craig into a cute little beach babe. Sue would be here for the next two weeks during which time I would be expected to dress and act as a woman all day, every day. Occasionally Sue and I would go out but she promised not to purposely try to embarrass me, if I behaved which of course she would be the judge of. I would have to wear dresses or skirts for that time and would also be expected to learn how to dress and do my own makeup and hair which was a little long and I would not be allowed to get cut. Craig would become Lori as soon as he got home from school and all weekend long. He too would be expected to wear dresses and skirts to get accustomed to them and would of course have to learn about fashion, makeup, and hair styling. Sue said that she would occasionally take him out also to get him used to being in public and the three of us would have little outings to movies or dinner which would be both a treat and a lesson in acting feminine. Sue mentioned that she had ordered a few things to help Craig and I in our transformation and that she expected us to use them faithfully. We would notice a few changes but they would all be reversible, Sue assured us, reversible if we so desired. After the two weeks were up Sue would have to go back to work and for a month we'd be on our own. John was going to take a vacation and spend the last two weeks before we moved helping us to polish our feminine images. Once we moved to California we would be women Sue assured us, smart, beautiful, and desirable women. She laughed and said that she wouldn't be at all surprised if we decided we wanted to stay that way forever! "Exactly what type of changes will we notice Sue?" I hated to interrupt her little fantasy of having a sister and niece forever but I did have a few questions. "Nothing much, and like I said it will all be reversible, if you want." I knew a brush off when I heard one and although a part of me was afraid to push the subject I still had to know. "Come on Sue," I prodded. "What changes? You know it's too late for us to back out now so spill what you know." "All right but remember it's all revers..." "I know, reversible, if we want. What I don't know is what they will be!" I was either very brave or very foolish but I wouldn't stop insisting until she broke. "Physical," Sue said with a sheepish grin. "You two will start going through puberty again, this time though when it ends, you'll have female sex characteristics. You know, wider hips, prominent butts, breasts, the usual." "Anything else we should know?" I was on a roll now, it was the first time I could remember having her on the ropes! "You'll be using a special gargle that will change your voices and the hormones may have some affect on your feelings." "Hormones?" I was stunned. I never expected anything like that although I probably should have. How else could we fit in so well as women unless we took something to change us into women? "All very safe, reversible, reliable, and very fast acting." Sue continued as if she were simply reading a cookbook. "A few weeks from now you'll notice some breast growth then some time later you'll be able to put your fake boobs in a drawer and your own in a bra. In between your butts will fill out nicely and fat deposits will accumulate under your skin making you look softer, rounder, and much more like women." "I'm going to have real breasts?" Craig exclaimed giddily. "Will I really be able to wear a bikini like Amy?" "You'll probably end up as a thirty two B," Sue explained. "I don't see any reason why you couldn't wear one if you want to?" "Hear that dad, er mom, I'm going to be wearing a bikini!" "And driving the boys wild," I added that just to watch Craig's reaction. It didn't seem to bother him at all that he'd be a magnet for boys, in fact a bit of a smile seemed to come to his face. My son, in a bikini, surrounded by boys and loving it! What about me?" I wasn't sure I wanted to know but it was probably best to know what was happening to me. "You'll probably end up with thirty four C bustline," Sue explained. "You're a little older and heavier which will make a difference." Sue filled us in on everything without any further prompting telling us that we could expect to notice a difference in how we reacted to things. we'd be more subject to our emotions as were most women and thanks to some special course we would take we'd also begin to think of ourselves as being female. Craig would start to think and act just like any other girl his age and I'd feel just like a woman my age, maternal instincts included! I would start on a more intensive training course that night listening to cassette tapes of relaxing music as I slept. Hidden in the tapes were messages that would slowly alter my thinking, making me feel more and more like a woman. Because of my depression the tapes would affect me immediately Sue explained, my confused mind would latch onto the suggestions and hold tight to them. In a matter of days I would find myself enjoying wearing pretty clothes and makeup. Later my actions would be the feminine gestures and actions that I was learning, and just to ice the cake I'd really begin to think of myself as Craig's mother! Craig would have a subtler course since he'd still have to retain his masculine gestures and actions until the end of school. He'd still be learning to think of himself as a girl and my daughter with all the appropriate thoughts and gestures being fed into his mind. When school was over he'd listen to a very special tape that would contain the keywords needed to flip the switch in his reprogrammed mind from boy to girl. We'd both stay that way until we decided we wanted to change back then everything would be reversed. I'd end up as a man again and Craig would, well that of course remained to be seen. After dinner the three of us cleaned up then went to the other room to wait for Sue to begin our promised training for the evening. she walked into the room after us carry three glasses and a bottle of wine she picked up while we were shopping. Pouring three glasses she handed Craig and I each a small bottle labeled "Femenhance", mine said level 3 while Craig's was level 2. The directions on the bottle were to take one pill twice daily to develop female physical characteristics then one pill a day after the desired level of development to maintain them. Sue played the part of the gracious hostess handing a glass of wine to me then one to Craig. "Dual purpose," She laughed holding the bottle up. "A toast to your new lives and something to wash down the pills with!" Craig and I stared at the pills sin our hands then seemingly with a single thought popped them into our mouths and took a sip of wine. "That didn't hurt did it now ladies?" Sue laughed. "You're on your way to becoming women now!" Sue was nothing was sweetness and love the entire rest of the evening, unless we made a mistake in how we walked, sat, or did any of the fifty or so other things she asked of us in the wrong way. Then it was back to being a Drill Instructor again, barking orders and waiting for instant obedience, which I might add she got! Even with the constant threat of being screamed at I found it sort of fun to watch Craig as he learned the hard way that becoming a girl wasn't going to be easy. Craig did pretty well for himself though, I guess he was more interested in being a girl than I was, and soon he was walking with a gentle sway to his hips and flipping back his hair with a shake of his pretty head. He adapted easily to wearing heels after having practiced with his mom's and seemed to have no problem in sitting properly. I wondered how he'd do when Sue took him out in public though, it was one thing to prance around the house pretending to be comfortable in women's clothes but outside where people would be looking at you and judging you was a totally different experience. I hoped Sue would go easy on him and wait until he was ready. By the end of the evening Sue was even congratulating me on how much better I was doing and it actually made me happy. I don't know if it had been that I was feeling so bad for so long but her compliments seemed to mean something to me, in a strange way it gave me a goal. I decided to work as hard as I could to make Sue proud of me, I'd be a great sister to her and a wonderful mother to Craig! At the end of the evening Craig and I both bathed and slipped on our nightgowns, this time though I did it without the hesitation I had the night before. Sue was showing me a way out of my depression and the nightgown was part of it as were the matching panties. I slid them on, put the tape into my player, turned it on and fell asleep listening to the beautiful music. Tomorrow would be another day I thought as I drifted off, what would it bring? The next morning I woke feeling a little better than I remembered feeling before. I couldn't remember a singe thing from the tape Sue insisted I listen to except that the music was great. I was always a big instrumental fan and the music on that tape was certainly among the best renditions of some of my favorite songs that I'd ever heard. I'd have to thank Sue for the tape at breakfast but thought that I should also mention that they didn't seem to achieve their real purpose. I hated to disappoint her but it was something that she should know I thought as I carefully brushed my teeth. Staring into the mirror I thought that I looked just a little pale and washed out. I felt much better though after I went back into my room put on my wig and brushed it out then brushed on a little blush and added some lipstick. I considered going down to breakfast in my nightgown but since I had plenty of time before I had to start breakfast I decided to change into something nice from my closet. I chose a nice sleeveless blue dress with a white skirt and short blue jacket to wear, dressy in a conservative way I thought, not at all like the black dress I had worn the night before. I hoped Sue would approve of it and give me a compliment to start my day out right. I had left my breasts glued on and found it almost erotic to place a lace covered bra against my chest and carefully pull it over my breasts. I had watched Mary do the same things in the past and had been so overcome that on several occasions I had stopped her before she had them completely in the cups so that I could pull her down and make love to her. Would she find it funny if she were here to watch me put on a bra? Would she try to attack me as I had her? Setting aside my erotic daydreams I slipped on a garter belt and carefully rolled up a pair of tan nylons and fastened them before slipping on a white full slip. I slid the dress gently over my head and carefully inspected myself in the mirror just as Sue had taught me to do, I didn't want to be embarrassed by having my slip show beneath the hem of my dress. I slid on the jacket and fastened the single claps before stepping into a pair of blue shoes with a medium heel. They were higher than the first pair I had worn yesterday but I felt that a lower pair just wouldn't look right with my outfit and I did want to start wearing high heels soon. With everything just right I set off to make breakfast for my sister and daughter. It wasn't until I was halfway done with breakfast that it hit me, I had wanted to wear something pretty and it had been my idea to put on makeup! Those tapes really did work! For a second I considered going back up and changing into something a little less pretty and maybe even taking off the makeup but then it didn't seem like such a big deal to me so I continued on with breakfast. No reason to change out of such a pretty outfit, it was comfortable and it looked good on me. Sue was also dressed when she came down, except that she had on a pair of jeans and a comfy looking top. "You're looking very nice this morning Jacki," She greeted me with a big smile after looking over my outfit. Sleep well last night?" "Very well, thanks," I said as I stepped back to let her get a better view of my outfit. "Thanks for the tape, I really enjoyed it!" "I noticed," She said with a knowing smile. "Any problems?" "I never even realized what happened until I was almost done here," I told her as I started to set out the plates. "I'm amazed at how well the tape worked!" " I have a few others for you," Sue told me obviously thrilled with my acceptance of the tape. "There's a whole series I'd like to have you listen to, they'll smooth out any rough spots and make a perfect lady out of you." I thought about objecting, I still wasn't positive I wanted to be a perfect lady, but instead I smiled and told her how much I was looking forward to using them! Geez, one night with a tape and I was becoming putty in her hands. After the whole set I just might find myself wearing some flimsy nightgown and going to bed with a guy, I'd have to check with Sue about that possibility but not right now. Craig came into the kitchen a few minutes later, leaned over and kissed Sue on the cheek then me. "Morning Aunt Sue, morning mom, Beautiful day isn't it?" "It certainly is!" I exclaimed once I recovered from the shock of having my son kiss me. "Why the kiss though?" "Just wanted to show you that I love you" He said with a shrug of the shoulders. "Did I do something wrong?" "Not at all Lori dear," Sue told him. "Doesn't your mom look nice? She picked out her own outfit today!" "Very nice mom," Craig said as he gingerly nibbled on the dry toast I made him. "Not as hot as you looked last night though!" "I can't look hot all of the time sweetheart," I said with a wistful smile. "But thanks for noticing!" I stared and smiled at Craig as he finished his toast and small glass of juice. He normally had a plate of eggs and several sausages which he washed down with a large glass of chocolate milk. Today I had given him a slice of dry toast and a small cup of juice and he was not only happy with it, he said he was filled! Apparently he was being influenced by the tape he had listened to. "Aunt Sue, in case I forgot during the excitement last night I wanted to thank you for that gorgeous dress and all the help you gave me last night. You're the sweetest aunt in the whole world!" With that he gave each of us another kiss, washed down his hormone pill with the last of his juice, gathered his books and was off to school. "Notice any change?" Sue asked. "Or was that the same old Craig? "Oh Craig was there," I said with a laugh. "But Lori was peeking out and waving to us!" "Wasn't that kiss so precious?" "I nearly fell off my chair." Craig hadn't given me a goodnight kiss since he was eight years old saying that big boys don't kiss their dads. Now he's giving me a kiss at breakfast and calling me mom. That must have been one powerful tape he listened to I thought. I did sort of like it though! As we cleaned up the dished Sue and I talked about fashion, what to wear when, how to mix and match outfits to extend my wardrobe, and how I should dress for the office. It was so much information that finally I had to tell her that I wasn't sure that I could remember it all. She just smiled, patted my hand and said that by the time I was ready to start working it would all be second nature to me. Sue put me through a refresher course in mannerisms which I passed with flying colors. Next came a practical lesson in female clothing in which we went through my closet and drawers so that I could learn what each item was called, along with how and when it was worn. I learned how to unzip dresses just far enough to get them over my head while still being able to reach the zipper to pull it closed. That was an important lesson for me, until then I wasn't sure how I'd dress if I had to do it alone. Sue spent a great deal of time on my lingerie, backless dresses required special bras that wouldn't show, strapless dresses required strapless bras, and if I didn't want to wear my fake breasts I'd need to wear padded bras. I learned about high cut panties, thong panties, briefs, and bikini panties as well as full slips, half slips, slips for evening gowns, pettipants, and dresses that didn't need slips. We took a quick break for lunch, at home this time, then back to learning about makeup, nail polish, and hair styling. Learning about makeup turned out to be very fascinating, I couldn't believe the hundreds of shades of what I thought were just a few basic colors. Men I soon found thought a particular color was known as red but women knew it as cherry red, burgundy, pink, frosted pink, deep red, passionate red, and numerous other variations. It amazed me that there were so many variations but Sue patiently explained that they were necessary for a woman to coordinate her makeup with her outfit. It would be a terrible fashion mistake for a woman to be wearing a red dress with pink lipstick. After hours of makeup lessons we moved to hair styling and learning how to use curlers. It was of extreme importance Sue stressed, to get a trained beautician I trusted to fix my hair in a flattering style. I could then keep that style or have it changed but I should never change it myself. That was a job for someone who knew what they were doing, all I should do is to try to maintain the style with curlers and brushes! After a long afternoon of training we broke for dinner then started on Craig. An hour after walking through the door Craig was gone, replaced by a pretty girl in a short tight skirt and heels. Sue let him do his own makeup just as I had earlier and even she had to admit that he seemed to have a natural eye for colors and which ones looked best on him. He did his eyes in a smoky brown to match his skirt and wore a shade of coral lipstick that seemed to just darken his natural lips color instead of looking as though he had lipstick on. He selected a shade of light rose blush over his foundation and powder which gave his cheeks a healthy glow. When he finished with a light brown mascara and added the hairpieces I was sure that no boy in the world would be able to resist his face or his legs! After dinner it was the same training in clothes, hair and makeup for Craig that I had gone through. He had a little trouble with the clothes that I did, my years of observing Mary had helped, but breezed through the makeup part. His toughest challenge was maintaining his modesty while trying to do everyday tasks in the mini skirt he was wearing. "I didn't realize how tough it was for the girls when they wore these short skirts," He mused as he held the skirt close and sat down on the sofa. "They sure look good in them though!" "Which is why they wear them," Sue told us. "What do you think of them Lori?" "I like them," Craig giggled. "They're a lot of trouble but they make my legs look so nice!" "Good girl!" Sue clapped happily. "You're learning fast. Being a pretty girl is a lot of hard work but it's worth it right?" "Oh absolutely Aunt Sue," Craig gushed as he worked on crossing his legs without showing off his panties. "Don't you think so mom?" "Yes, I suppose you're right Lori but I'm a little old for mini skirts." I felt a twinge of regret come over me. My legs are every bit as nice as hers, I thought to myself. Maybe I should pick up a short skirt or two for myself! At the end of the evening we were all worn out from the hours of constant practicing s