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Family Changes
by: Karen Elizabeth L. © 1999
"Youre 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?"
"Dont be ridiculous," I laughed. "Id 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 cant 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 Im 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 womens 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. Craigs 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 Craigs 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 wouldnt worry about Craig if I were you Dave," Sue said with a laugh. "Hell be just fine."
"Fine! It might send him over the edge." How could Sue be so callous I wondered.
"Craig will be fine, youll be fine, the whole world will be fine," Sue laughed. "Now are you willing to bet or not?"
I shouldnt have done it, I realized that at the instant I accepted the bet but Sue wasnt about to allow me to renege.
"Okay, you wont let me back out but youre going to have to go pretty far to win this, I dont plan on just taking your word for it!" I said bitterly.
"Far?" Sue laughed. "I dont have to go very far at all. As a matter of fact lets start right here."
"Here?" I asked confused. "Whats 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 wasnt the first time hed 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 didnt do anything that might call attention to himself. Mary had been keeping it a secret from me for several years afraid that I wouldnt understand, Sue explained.
"Understand?" My mind was spinning out of control. "Of course I wouldnt understand, I still dont! Craig has always been a perfectly normal boy, hes 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 girls clothes." Sue grinned broadly and clapped excitedly. "I win!"
"Hold one, one misadjusted kid doesnt 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, Id deal with Craig later. "Would John do?" Sue asked calmly.
"John, Your fiancee John?" I gasped. It couldnt 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. Id known John since Sue brought him for thanksgiving dinner three years ago. Id gone hunting, fishing, and skiing with him but I never suspected anything odd.
"Thats 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 youre 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 isnt she?" Sue broke my concentration and brought me plummeting back to reality.
I picked up the letter and slowly read Johns explanation of his dressing and assurance that hed be there to help me every step off the way as I made the change into a woman. I didnt 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?"
"Youre not working so I thought it would be best to start right away. You can dress like a woman around the house, its secluded so no ones going to see you. Well explain everything to Craig when he gets home from school, Im sure hell 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 cant leave him in Minnesota while Im off in California!" I shouted. "Im 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 cant 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 hell be adorable!
I felt terrible as I listened to Sue describe her plans for me and Craig. I hadnt 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 womens 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 Id never consider becoming a secretary even as a male, since I too would consider it to be a womans job. My pride would keep from taking a job with a lucrative paycheck and eventually Id 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 couldnt hold out for long so she simply waited for the right time to spring it on me.
Her timing couldnt 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. Id be happier, Id have a good job with a very good salary, Id 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?" Craigs head swiveled around to see Sue smiling at him.
"What did you say Aunt Sue?"
"She wants to know if youd mind wearing a bikini to the beach." I moaned. "You see theres a catch to this little vacation."
"Me, wear a bikini?" Craig shot back obviously trying to hide his excitement. "Youre 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?"
"Im sorry dad, really I am. I dont know why I did it but Ill never ever do it again!" Tears ran down Craigs cheeks in a torrent.
"Calm down Craig," I sat next to him and gave him a hug. "Please pay attention and dont 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?
"Youre serious arent you dad? Were really going to move in with Aunt Sue, youre going to be my mother and Im 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 dont know anything about being a girl. I just played around with some clothes."
Sue assured him that by the time summer came hed be a perfect girl and wouldnt give a thought to even wearing a bikini. The big gin on his face told me that he couldnt 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 womens 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 didnt 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, dont you feel sexy?" Sue asked. "Just imagine how sexy youd look in a pretty dress with heels on!"
"I dont feel sexy at all," I shrugged. "I still think this is a stupid idea but I dont have any other options right now."
"Dont worry your pretty little head about it little sister," Sue giggled. "Soon youll find yourself looking forward to wearing something sexy under your outfits. It feels wonderful to wear something really frilly and sexy like that Youre the only one who knows what youre wearing and it makes you feel so feminine and naughty!"
"I dont 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 wouldnt 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 youre a guy?"
"Hell, Im not even sure that theres 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 Id 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 Im very good at what I do, you werent 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 my 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 didnt 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 shouldnt let you do this to me Sue," I tried to let her down easily. "Its just not right. Im a man, a father for heavens sake, you just cant change that."
"Bet me!" Was Sues challenge. "In just a few more weeks you wont think of yourself as anything other than a single woman and the mother of a teenage daughter. Youll see a pretty woman and compare yourself to her wondering if your butt is a as nice as hers, what youd look like in the dress shes wearing, and if you should get your hair done like hers."
"Its not going to happen Sue, Ill never think of myself as anything other than a man pretending to be a woman.""Well see," Sue said with a devilish gleam in her eyes. "By the way, we cant 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.
Id go along if only because for some strange reason this was lifting my spirits. Soon Id be leaving for sunny California, a new job, and a new life as a woman. It wasnt the type of job or life I wanted but I found the idea to be sort of intriguing and that was more than Id 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, Id 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 youre not careful! Get up and lets 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. "Lets pick up something for lunch!" A feeling of panic swept over me. "Im not going out in these clothes, someones bound to notice."
"Well just go to the drive through, you wont need to get out of the car. I just want you to get a feel for going out this way, youll 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 didnt 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, theyd momentarily look at our faces then our chests and if they were close enough theyd look down to see if we were wearing skirts and check out our legs. If they couldnt see our legs theyd 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 didnt 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 what 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 cant 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 wasnt 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.
"Dont eat too much Jacki," She chuckled. "You have to watch that figure of yours now. In case youre interested youre a perfect size nine, the same as me, a great size for finding really great outfits. If I were you Id try really hard to stay that size."
What did she expect me to say to that - thanks for the great advice sis, Ill keep to a strict diet and start exercising? I just gave her a smile to shut her up as Id 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.
"Youre 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 cant go in there," I begged and pleaded for sympathy but her eyes had that cold look I had always hated. "Im really happy that you think Im a perfect size nine, really I am!"
"Too late, Jacki," She said coldly. "But Ill still go easy on you and not make you talk. Other than that theres 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 youre 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 someones face, and then it would turn into a laugh and theyd 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 wasnt going to be the one to expose me. No, the look on his face said that there was nothing hed like more than to see me exposed! Sue noticed the mans stare and her face lit up."Smile at him!" She whispered. "He likes what he sees, smile to say thanks for the compliment!"
I wasnt 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. Its impossible to describe the relief I felt when he returned my smile, nodded, and kept walking!"See that wasnt 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. "Youre having a good old time setting me up like this, arent you?"
"Yes I guess I am," Sue replied indifferently. "But at the same time youre learning some important lessons, you really can pass as a woman, and youre learning how to react to men."
"Im not ready for these kind of lessons yet and you know it!" I argued. "Youre pushing me too far, too fast."
"Were you ready for that dress?" She teased. "That lingerie?"
"You know what I mean," I pleaded. "Its too much!"
"If you were wearing a flimsy negligee and getting into bed with a guy I might say its 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 didnt 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 couldnt 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 couldnt 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. "Hows it feel to have men lust over you Jacki? Did you enjoy it?"
"It felt weird and very scary!" I admitted. "I dont think I care for the way men have been looking at me, its 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 wasnt 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. Youre going to have to get used to men looking at you, believe me theyre not going to stop. If you just relax and let me work with you I promise youll 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 shed 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 shed 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, youll 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 youll 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 Id be buying myself pretty shoes to go with every outfit I own and that theyd 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 couldnt 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 didnt really think Id 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 couldnt quite make out.
"Here you go," She cried triumphantly. "Just what that dress cries out for!"
"A woman to wear it?" I joked hoping shed 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 Ill 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. "Its too tight, I cant breathe!"
"Dont be such a baby," Sue laughed. "This is a waist cincher, itll give you the shape you need for that dress. Just calm down, in a few minutes youll get used to the tightness and adjust your breathing." "In a few minutes Ill 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 wasnt 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 isnt she?" Sue giggled guessing what I was thinking. "And thats just her face, it gets better. Want to see?"
Between being stunned and the cincher I just couldnt 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 Id 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!
"Thats you in there Jacki," Sue taunted. "That beautiful, sexy woman in the mirror is my little sister Jacquelyn. Shes gorgeous, dont you think?" "Gorgeous," I whispered. "But me?"
"All you Jacki dear," Sue whispered back. "This is what youre 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. Youre 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. "Wheres my dad?"
Sue acted as if nothing was unusual. "Your dads gone, Craig." She said very calmly and deliberately. Gesturing towards me she smiled. "Id 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 its really me Craig," I smiled. "So quit staring at my breasts like that will you!"
Craig immediately returned his gaze to my face. "Youre beautiful dad, I cant get over how good you look!"
This time I didnt wait for Sue to step in. "Thank you Craig, thats very nice of you but please remember to call me mom okay?"
"Uh okay mom," He agreed with a laugh. "But youre still hot!"
"Thanks," I said as I slowly walked over to him and took him by the arm.
"Now its time to change you into my daughter Lori. Are you ready?" "I cant wait!" He shouted excitedly. "I just want to look as good as you do okay?"
"Trust me Lori," Sue laughed. "Youre 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 couldnt 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 Craigs 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 dont know how much this means to me!"
"Im happy to help you Lori," Sue told him. "I just want to see you and your mom smiling and happy again."
"I dont know about dad, I mean mom, but I couldnt be happier!" Craig said his eyes beginning to glisten with tears.
"Id be happy if I could just breathe and get out of these heels," I laughed trying to seem happy. "But in any case its your turn now Lori, so lets get changed and have dinner."
Actually I didnt care about whether I had dinner or not, for some odd reason though I couldnt seem to wait to watch my son being transformed into a pretty girl!
"Arent 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. "Were all girls here. If you cant 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 werent 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 Id see just how much fun Craig thought this was going to be. Just wait until I glued these breasts on to his chest, hed realize that to Sue this wasnt 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 hed feel as silly and humiliated as I had but instead he was smiling happily.
"Thanks mom," He said softly. "I never thought Id 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 hed balk at taking what might have been a little game as far as this. Instead of balking though Craig was happier than hed 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. "Youre 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. "Im going to be so proud to have such a lovely girl as my daughter!"
"I think youre 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 Craigs 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 Ill 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 wouldnt 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 didnt 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 Id 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 wed 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 wouldnt 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 its too late for us to back out now so spill what you know."
"All right but remember its all revers..."
"I know, reversible, if we want. What I dont know is what they will be!" I was either very brave or very foolish but I wouldnt 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, youll 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!
"Youll 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 youll notice some breast growth then some time later youll 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."
"Im going to have real breasts?" Craig exclaimed giddily. "Will I really be able to wear a bikini like Amy?"
"Youll probably end up as a thirty two B," Sue explained. "I dont see any reason why you couldnt wear one if you want to?"
"Hear that dad, er mom, Im going to be wearing a bikini!"
"And driving the boys wild," I added that just to watch Craigs reaction. It didnt seem to bother him at all that hed 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 wasnt sure I wanted to know but it was probably best to know what was happening to me.
"Youll probably end up with thirty four C bustline," Sue explained.
"Youre 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. wed be more subject to our emotions as were most women and thanks to some special course we would take wed also begin to think of ourselves as being female. Craig would start to think and act just like any other girl his age and Id 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 Id really begin to think of myself as Craigs mother! Craig would have a subtler course since hed still have to retain his masculine gestures and actions until the end of school. Hed 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 hed listen to a very special tape that would contain the keywords needed to flip the switch in his reprogrammed mind from boy to girl. Wed both stay that way until we decided we wanted to change back then everything would be reversed. Id 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 Craigs 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 didnt hurt did it now ladies?" Sue laughed. "Youre 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 wasnt 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 moms and seemed to have no problem in sitting properly. I wondered how hed do when Sue took him out in public though, it was one thing to prance around the house pretending to be comfortable in womens 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 dont 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, Id 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 couldnt 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 Id ever heard. Id have to thank Sue for the tape at breakfast but thought that I should also mention that they didnt 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 didnt 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 wouldnt 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 wasnt 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 didnt 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. "Youre 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. "Im 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. "Theres a whole series Id like to have you listen to, theyll smooth out any rough spots and make a perfect lady out of you."
I thought about objecting, I still wasnt 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, Id 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 isnt 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. "Doesnt 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 cant 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. Youre 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!"
"Wasnt that kiss so precious?"
"I nearly fell off my chair." Craig hadnt given me a goodnight kiss since he was eight years old saying that big boys dont kiss their dads. Now hes 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 wasnt 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 wasnt sure how Id dress if I had to do it alone. Sue spent a great deal of time on my lingerie, backless dresses required special bras that wouldnt show, strapless dresses required strapless bras, and if I didnt want to wear my fake breasts Id 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 didnt 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 couldnt 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 didnt 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. "Theyre a lot of trouble but they make my legs look so nice!"
"Good girl!" Sue clapped happily. "Youre learning fast. Being a pretty girl is a lot of hard work but its worth it right?"
"Oh absolutely Aunt Sue," Craig gushed as he worked on crossing his legs without showing off his panties. "Dont you think so mom?" "Yes, I suppose youre right Lori but Im 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 so after a few goodnight kisses we parted to ready ourselves for bed. I was looking for a nightgown to wear when suddenly I was overcome with the urge to wear a very short, very sheer, gown with a matching jacket and panties with rows of ruffled lace on the seat. The gown had short sheer sleeves, a satin underskirt ( I learned the term from my wardrobe lessons) for modesty, and a sheer lace bodice (another term from my lessons). It was something a woman would wear for her honeymoon or a romantic get away with her husband or lover since it pretty well screamed out take me! I looked around worried that someone might be watching me then quickly pulled out the gown, robe, and panties and dashed into my bathroom to admire its breathtaking beauty as I waited for my bath to be ready.
When all was ready I slipped into the tub of warm , softly scented water and let the silky bath oil work on my skin as I relaxed or at least tried to relax. the problem with relaxing was that I had hung the nightgown I wanted to wear on a hook that was directly in my line of sight from the tub. There was just no way to avoid seeing it as I laid back to enjoy my bath and the more I looked at it the more excited I became! I was getting all worked up imagining how sexy that nightgown would look on some lovely woman later that night but I was going to be the woman in that nightgown! I was starting to turn myself on!
I felt guilt about wearing the nightgown when I finished my bath but something inside my head told me that I was going to love the silky sensation of the satin underskirt against my soft, smooth skin and I just had to see if I looked as sexy as I had imagined I would. As I slid the panties on I noticed how exquisitely smooth and silky they felt against my skin and that I was getting even more excited wearing them than I was thinking about wearing them. I quickly slipped on the gown hoping to hide the telltale signs of my growing excitement but it wasnt of much help coming as it did to just past my panties. I used to beg Mary to wear clothes like this but she refused saying it made her feel silly. I felt sexy, naughty, and just a very little bit guilty but silly was not something I was feeling at all. I set up my cassette player then slipped between the sheets enjoying the silkiness of my nightgown and panties against my body. Surely this is what heaven was meant to be like!
The next morning I felt wonderful, happy, carefree, and anxious to show off how I looked in my nightgown. I slipped on the short robe with the pink sash and was just ready to start breakfast when I realized that something wasnt right. I thought and thought of what it could be, makeup would be silly with a nightgown, so would a pair of heels or nylons, something was missing but what? Just when I thought Id never think of what was missing it hit me - perfume! A light spritz of perfume would really set this little ensemble off just perfectly! I found a scent on my vanity that I liked so I sprayed just a small amount on my neck and went to make breakfast content that I was done up just right! When Sue entered the kitchen I stopped what I was doing and turned with my arms outstretched so that she could get a good look at what I was wearing.
"Jacki, that is such a sexy looking outfit!" She gushed. "You look positively delectable in it too!"
Thanks," I blushed self consciously even though I really didnt want her to stop telling me how pretty and sexy I looked. I wanted to know that I was woman enough to wear satin, lace, and chiffon. "I came across it in my drawer last night and I just had to wear it. It isnt too slutty looking is it?"
"A woman is allowed to look slutty now and then," Sue laughed. "It reinforces your femininity to feel sexy and desirable!"
"Im so glad you said that," I sighed with relief. "I was really worried last night that I might be going a little too far too fast."
"How do you feel now?" Sue asked concern evident in her voice. It was so nice to have my sister showing such concern for me. I blinked back a tear and collected my thoughts. "I feel pretty, feminine, sexy, and so happy that Im going to cry!"
"Go ahead and have a good cry if you feel like it," Sue told me as she kissed me on the cheek. "Its a womans privilege as much as changing her mind."
Sues kiss seemed to cheer me up that suddenly I no longer felt the need to cry. I still had to get breakfast ready and I couldnt wait to see what Craig thought of his mom in a sexy little nightie! I thanked Sue for her concern then kissed her back before returning to preparing breakfast. Minutes later I heard a low whistle as Craig caught sight of me.
"Mom you look so hot!" He said as he stared. "Got a boyfriend stopping by later?"
I playfully swatted him on the backside. "You know Im not interested in having a boyfriend. Im afraid that youd steal them away!"
"Your boyfriends would be just a bit too old for me mom, " He joked.
"Im not in the market for a Sugar Daddy right now!"
"Oh really," I asked in a mock serious tone. "And just what are you interested in?"
"Well theres always Randy, the quarterback of the schools football team." Was I seeing things or did Craig have that far off look in his eyes of a girl in love?
"That cute huh?" I knew I was leading him on but I was wondering how far he was really willing to take this idea of becoming a girl. "Oh mom, hes the cutest boy in the whole school, maybe the whole world!" My sixteen year old son had a major crush on the quarterback! I hoped hed hold on long enough for us to get to California. It would be very hard to explain why he was staring all dreamy eyed at another boy. After breakfast I sat down and had a long talk with Sue about Craig. As it happened she was concerned about his attitude too but explained that it was a combination of the tapes and the hormones. He was a slow developed and the female hormones in the pills must have had a stronger effect on him than Sue had counted on. He was having feelings of attraction to boys because of the hormones and those feelings were reinforced by the tapes. I was going to have to sit down and have a little mother daughter talk to him about boys in the hopes of getting his emotions settled down before they got him into trouble.
I felt so much better after talking to Sue that while I was changing I decided to listen to another one of the tapes she had given me. I knew that they were designed to make me feel more like a woman but that was okay, Id been listening to them for two straight nights now without any problems. It wasnt as if I was working the streets hustling men or anything like that. I was going to have to start looking for a job as a woman soon so it was a good thing for me to get used to all of the pretty outfits I would be wearing.
I removed my nightie as slowly as I possibly could, okay I actually did a striptease routine that left me in a giggling fit! When I finally recovered I decided that after the wonderful experience of wearing a sexy nightie I should try something daring for the day also. I thought about a miniskirt like Craig had worn but it just didnt seem right to me. I didnt want to look like some over the hill streetwalker, I just wanted to feel really pretty and sexy like I did when I wore that nightie or that black dress. I looked at the clothes in my closet but there wasnt anything sexier than that black dress and I didnt feel in the least bit interested in wearing that waist cincher again. It was sexy looking and it gave me some wonderful curves but it had taken most of the evening before I had gotten used to wearing it. I was about to give up when I got the idea for the perfect outfit. A full skirted red dress with a black patent leather belt would certainly catch peoples eye and if I selected just the right lingerie I could project an image of a well dressed secretary without anyone knowing that I was wearing my sultriest lingerie underneath! I quickly pulled out a pair of black lace bikini panties, a push up bra with lace cups, a garter belt with black lace garters, a sexy looking black full sip and a pair of the sheerest black nylons that I owned completed my lingerie.
I carefully examined the way I looked in the mirror before donning my dress. My breasts were being pushed up and out by my bra, my panties were taut against my hips and just high enough to prevent any embarrassing show of my true sex. My garters were carefully threaded though my panties, and my lace trimmed slip ended several inches above my sexy looking knees! I was one hot looking lady. I put on my wig and brushed it out all by myself but I needed a little help from Sue with my makeup.
"You look fantastic Jacki!" Sue told me as she thinned out my eyelashes. "This will give your eyes a little sexier look though. You have such pretty features, its a shame you had to be a guy."
"I guess you mean that as a compliment so thank you," I certainly didnt want to aggravate her when she was next to my eye with a sharp object and I was beginning to appreciate my new looks. When I thought about it I couldnt believe that in a few short days Sue had cheered me up and given me something to live for.
"Youre starting to enjoy dressing this way arent you Jacki?" Sue teased as she applied a coat of mascara to my lashes. "You like being a pretty woman dont you?"
I smiled up her, I probably didnt need to say a word but I wanted to. "Yes," I answered blissfully. "I guess I am. I love wearing sexy lingerie under my clothes! Its just the way you said it would be, just an ordinary lady on the outside but sexy and oh so feminine underneath!" "Are you afraid?" Sue asked softly as if reading my mind. "Does it bother you that you enjoy becoming a woman?"
"Yes, it still bothers me a little bit," I confessed happy to unload my feelings. "I guess I never thought of myself as much of a woman before, I never thought I could look like this."
Sue assured me that faithful listening to the tapes would ease my guilt and allow me to enjoy living as a woman. Soon Id be dressing in more casual clothes and living my life completely as a woman with little thought of being a male. I would she promised be happy and content living as a woman and a mother.
I began picturing myself in a pretty outfit watching a football game where my pretty daughter Lori was one of the cheerleaders, Shed be stirring up the crowd in her short skirt and tight sweater, her long blonde hair tied back in a cute ponytail. The reason for her excitement would of course be her boyfriend the quarterback.. After the game she and I would stop for a cup of hot chocolate and shed tell me all about how wonderful, cute, and sexy her boyfriend was. Id smile happily enjoying the mother daughter bonding.
"Are you still there Jacki?" Sue asked as she finished with my makeup.
"Thinking about something special?"
"Being a mother to Lori is going to be wonderful," I answered wistfully.
"I just know Im going to be a great mom for her."
Sue let me go on and on about how wonderful I felt as Loris mom as we straightened up the house then reaching into her suitcase she produced a large envelope and pulled out a sheaf of legal documents. Laying them on the table before me she smiled and said, "Time to put your money where your mouth is Jacki!"
I looked over the papers in font of me and felt my heart leap into my throat. Staring me in my pretty face were documents asking that corrections be made to my and Craigs birth certificates - the sex was to be changed to female and our names were to be changed from Steve and Craig to Jacquelyn Marie and Lori Elizabeth. After that came a form to change my drivers license to show my new name and sex and to have all of Craigs records changed to his new name and sex. Once everything was submitted and approved Craig and I would be legally considered to be Females by the state of California.
"Come on Jacki, you told me that you couldnt wait to be a woman and a mother all you have to do is sign these and from the moment you arrive in California you will be!" Sue was pressuring me to give up my masculinity and become legally female along with Craig. I reached for the papers and the pen that she offered me. I wanted to be Jacquelyn Marie and I knew Craig would want to be Lori Elizabeth, all I had to do was to fill out a few simple forms and our dreams were on their way to becoming reality. I smiled happily as I filled out the requests and signed them, all that was left would be Craigs signature when he got home.
After I signed the papers I smiled at Sue, "How about lunch?" I asked.
"Ive got cabin fever and need to get out."
"Youre willing to go out dressed like that?" She beamed. "Are you positive?"
I fluffed my hair and pouted. "Dont you want to be seen with your little sister?"
Sue threw me a small black clutch purse, grabbed her own and we were off to lunch. Once again I was going to be far away from the safety of my home while dressed entirely as a woman. This time though it was my choice and I couldnt wait!
We pulled into the parking lot of a restaurant that catered to many of the local office people which is why I had asked to go this one. I wanted to get a look at what the women office workers wore just to make sure that I fit in when I eventually became a working girl myself.
Once again my the clicking of my heels on the surface of the parking lot seemed to announce my arrival but this time it sounded like a beautiful symphony to my ears. I was a woman and this was the sound a woman made, it was wonderful!
We ran into a man leaving just as we got to the door, he smiled and held the door for what he surely thought were two women out for lunch. I caught his eye briefly, smiled, and thanked him for his kindness. His smile widened noticeably as he nodded and said good afternoon to us. It was just as Sue had told me, as an attractive woman I would have incredible power over men with just my smile. I had certainly brightened up that mans day just by giving him a smile, it cost me nothing but gave me an exhilarating sense of control. I followed Sue into the lobby with my head held just a little higher, my breasts jutting out just a little further, and a new sense of self confidence.
As we waited to be seated I took a quick glance around and noticed that men sitting nearby were fining all sorts of reasons to look in our direction. One man must have decided that the wall next to us was suddenly the most interesting thing in the world judging by his stare. Once in a while I would notice his eyes moving from the wall to the floor and our legs but he always avoided my gaze by returning to his study of the wall. Another was clearly interested in us and made no attempt at all to hide his appreciation for our looks, smiling if I happened to catch his eye which was busily undressing us.
So that was what it felt like to all the women I had stared at, did they realize I was undressing them with my eyes? Did they find as much enjoyment in it as I was finding? I often wondered what they were wearing under their dresses and suits, did they get as much delight wearing erotic lingerie under an ordinary suit as I did? My world was changing rapidly and it was all I could do to hang on for the ride. I had so many questions, experienced so many wonderful new feelings, and loved each and every minute of my new life!
I paid careful attention to what the other women wore, how they acted, and everything about them. None of them seemed to notice my watching them, if they were interested in anything but their lunches it never showed. It was an odd feeling, similar to being invisible, as long as they thought I was a woman I could look as much as I pleased. Studying the other women really boosted my ego, I was dressed and acting just like any other woman, I fit in perfectly!
I had a pretty light lunch since I had a private goal of fitting into that sexy black dress without a waist cincher then we were headed for home when Sue brought up the idea of having my nails done and ears pierced. "It sounds like fun but Id almost certainly be discovered," The thought of having my ears pierced really excited me. It would be a big step to modify even that small a part of my body to make me more feminine but someone that close would realize that I had on a wig. Even sitting there getting my nails done would put me under a magnifying glass that I wanted to avoid.
"What if," She asked, dangling what she knew to be a juicy carrot before me. "I took you somewhere where it wouldnt matter? Would you consider having your hair styled too?"
"Id let them do anything they wanted!" I promised. "Anything!" If only such a place existed it would be the answer to all of my prayers. "All they do is hair, nails, and ear piercing," Sue laughed. "Anything else is a personal problem for you!"
"That would be just fine, thank you," Was she just teasing me or did such a place exist?
"Good, because you have a two thirty appointment, wed better get going!"
"An appointment? You set this all up without asking me if it was okay?" I didnt know whether I should be mad or not, once again she was making important decisions without asking me. Of course an opportunity like this was too good to be passed up!
"Did I ask your permission to take you shopping that first time?" She flashed me her best stuff it smile. "Today you practically begged me to take you out. Now do you want to look like those women in the restaurant or not?"
She knew the answer, I could see it in her face. "I hope you know what youre doing," Sue drove to a small shop called Lindas where we were greeted by a woman a year or two older than me. She introduced herself as the owner, greeted me as Jacki and led me back to a room and asked that I take off everything but my bra and panties then put on a button down shift. Once I was changed Linda escorted me back out to the shop, shampooed my hair then led me to a waiting chair where they already had a manicure tray set up with several other items I didnt recognize. After taking my wig she began working on my hair. She seemed so easy going and friendly that we were soon chatting away as if we were old friends.
"Your sister tells me that you want to go out without your wig as much as possible," She said as if there was nothing odd about what I was doing. "Luckily your hair is just long enough and thick enough that it can be fixed into a pretty style that should be just what you want. Its a very popular style with my clients who want to do without a hot wig in the summer."
"I didnt realize that many women wore wigs, they all seem so natural looking!" I guess she realized what I was really asking.
"Some do but I was talking about my male clients!" Even her laugh made me feel at ease. She wasnt laughing at me, just at a crude attempt to ask what was really on my mind.
"Im sorry, Im very new at this. I never realized before that many men did this sort of thing."
"Enough to make my family financially secure to say the least." Her laugh and smile were contagious and soon I was relaxed and listening to her stories of how she got into making men pretty.
She had worked in a shop for years just barely making a decent wage when she decided to strike out on her own. It was tough going and she was about to give up when she got a call from a man asking if shed mind making him up for a party. She had her doubts but needed the money so she agreed and set an appointment.
As she listened to what the man wanted done she began to realize that he was asking for things to be changed that would not wear off in the near future. She finally told him that it would be easier for her if he told her what her really wanted and he broke down and said he wanted to be able to pass as a woman for a job interview. She thought it a little odd but a customer was a customer and soon he was a very happy customer with golden blonde hair, perfect makeup, long, polished nails, and smooth legs. Several weeks later a very well dressed woman in a smart looking business suit stopped in to thank her for helping her land the job and asking if shed mind if he recommended her service to some of his friends who also wanted to look like women. She agreed and soon had a clientele pleased with both their looks and her discretion.
Sue looked at me smugly, an "I told you so " grin all over her face. God, I hated it when she was right!
"My husband wasnt thrilled about it at first but once we bought the new house wed always wanted he never complained again!" Linda laughed as she combed and cut. "By the way Jacki, is there anything special youd like to have done?"
The question caught me completely off guard. I was finally being given a choice in what was being done to me, what a shock! A tiny whisper in the recesses of my brain wanted me to tell Linda to stop, that I didnt want to wear womens clothes, didnt want my hair and nails done, didnt want to be a woman at all.
"Yes," I nearly shouted in glee. "Can you dye my hair the same color as my wig? I think it would look so pretty!" So much for the whispering in my brain. Now it was more of a faint whimper, growing fainter by the second.
Hours later I was rolling my nylons up my silky smooth, newly waxed legs being very careful not to snag them on either my long red fingernails or my pretty red toenails. Only after I was completely dressed did I chance a look at myself in the mirror.
After I was all done Linda had allowed me to look at myself in a mirror. I was thrilled with the pretty hairstyle she had created for me, short but undoubtedly feminine, very pretty and flattering, and a near perfect match of the color I had hope for. Looking at it now with my dress on I could see that it was everything I wanted it to be and I was practically in tears because of it! I could go shopping, have lunch, see a movie, do anything I wanted to do without worrying about my wig.
If my new hairstyle wasnt enough I could always stare at the pretty little gold balls in the center of my earlobes. Linda had worked very hard to make me over into a woman and I couldnt begin to thank her. My legs were smooth and silky, my face was still tingling from the facial and makeover, gorgeous red nails extended beyond my fingertips and I was the happiest woman alive!
"What do you think of yourself now Jacki?" Sue asked as I left the changing room. "Are you satisfied that youll pass?
"Pass? I was thinking of entering a beauty contest or two!" I feigned indifference for maybe thirty seconds then threw my arms around Sue and hugged her tight. "Thank you Sue, youve been so good to me!" "I was worried that you might get mad at me for this," Sue admitted. "I couldnt stand to watch you sink any further, I had to do something drastic just to get your attention. This is all I could think of." "I could never thank you enough for what youve done Sue. I know its a little odd but I dont care, Im really having a wonderful time as a woman!"
Between Lindas and home I must have thanked Sue a couple of dozen times but I still didnt think it was enough. After all she had picked me out of my depression and shown me that I could have a life if I wanted to, a life as a beautiful woman for as long as I wanted!.
Craig told me that I was a real knockout and hung on my every word as I talked about the events of that afternoon. Once again he was wearing a miniskirt but this time it was as if hed grown up in them, he sat perfectly with his legs together and his movements were the perfect emulation of a poised young woman who had the benefits of a finishing school. It wasnt hard to imagine him sunning himself on a beach in a cute little bikini, a good looking guy rubbing suntan oil on his back, or at a formal dance in a pretty gown dancing with some handsome young man who was totally captivated by the lovely young woman in his arms. Craigs looks and actions would surely guarantee him plenty of male attention and he seemed to know it.
Sue worked us tirelessly until we could do anything she asked in a feminine manner without having to think about it. It had been a long, hard week with me starting off as Steve and ending up as a beautiful woman named Jacki and my sixteen year old son wasting no effort to become my daughter Lori. The long week had finally come to an end though and it was finally Friday, the day Sue had promised to set aside to let her sister and niece celebrate.
Craig burst through the door after school and after a quick "Hi Mom" to me he sought out Sue and asked if she was still serious about letting us celebrate. His question answered to his satisfaction he hurried off to his room to change into something more appropriate for a young woman out for dinner with her mom and aunt. My dress was dark blue with a white pleated skirt, white trim on its short sleeves and lapels, and an insert for the bodice that appeared to be the lace top of a dark blue camisole. My lingerie was virgin white satin, the panties had a lace front panel, and the bra was another push up style designed to produce breathtaking cleavage. I slipped into one of my favorite garter belts, rolled on a pair of white silky nylons then stepped into a white half slip with a six inch lace hem before I slid my dress over my head. The sensation of my skirt brushing against all of that nylon and satin was nothing short of being sinfully erotic and I loved every second of it!
I did my makeup and carefully brushed out my hair to keep the look I had gotten at the beauty shop. A pair of dark blue pumps with three inch heel completed my outfit and provided me with a sexy little sway to my butt as well as drawing attention to my long legs. I examined myself carefully in a full length mirror then checked my makeup in a magnifying mirror but Frankly it was just a waste of time, I was simply beautiful! Sue was wearing a very nice green dress, low cut but below the knees.
She was a good looking woman and men had always found her attractive.
I found myself wondering which of us theyd prefer now!
When Craig was finally ready I thought it a real shame that there werent any trumpeters forming a lane for this most beautiful princess to walk down. He wore a black dress with a pink cast to it that shimmered as the light caught it. His lipstick was a subdued shade of pink that matched the pink in his dress perfectly and his eyes were highlighted with white then overlaid in pink. All of his practice with his makeup had obviously paid off as his face did not appear to have had a drop of foundation or a grain of powder on it. Even the light touch of pink blush on his cheeks looked perfectly natural and blended in so well with his nail color. Craigs dress had a very modest scoop neckline which was offset by being just slightly longer than the baby doll nightgown I enjoyed wearing. His legs, so smooth and shapely, looked as though they were meant to be admired and I had little doubt about they would be as soon as boys caught sight of him!
He wore a pair of pink low heeled pumps with a small black bow at the tongue which drew your eye to his trim ankles then to his well shaped legs and back to the hem of his dress. Craig had done his homework and learned his lessons well, he presented the perfect picture of a well dressed young lady.
The three of us exchanged compliments on our outfits then with Sue leading the way slung our purses over our shoulders and walked out to the car, skirts swinging and heels clicking. Craig was a little hesitant about getting in but after watching me slide right in he held his short skirt close to him and slid in next to me.
"Youre sure this is safe, right mom?" He asked nervously. "Everyones really going to think Im a girl right?"
"Its going to be fine Lori, " I said soothingly. "I felt the same way my first time but if you just relax youll have a ball.. Youre a pretty young lady out for dinner with her mom and aunt, just act the part and nothing will go wrong.".
Craig closed his pretty eyes and took several deep breaths which caused his bust to rise noticeably. He exhaled, smiled and said he felt better knowing that his mom was there with him. I felt so warm and protective that I leaned across and kissed his head. "Dont worry Lori, Moms here with you." I told him as I held his hand. It seemed to make us both feel better.
We were escorted to our seats by a pretty young woman about Craigs age with long blonde hair and a tight skirt that showed off her cute little butt and legs. "What do you think of her?" I whispered to Craig who was staring at the young woman as she walked away from us.
"Im wondering if Id look that good in a tight skirt," He replied absent mindedly. "And shed look better with shorter hair." The old Craig wouldve been more concerned with getting a date with a hot looking girl like that but now all he could seem to think of was how hed look in her outfit. Hormones, special tapes, they were all having the desired effect on us, we no longer seemed to think of ourselves as males. Women held an interest only for purposes of comparing ourselves to them, sexually there was nothing.
We enjoyed a wonderful dinner and were the object of many a males admiring glance. Craig found it hard to take at first but Sue whispered something to him which made him smile, cross his legs, and sit up much straighter to the delight of several young men in the immediate area. Whatever Sue had done had just caused Craig to do a complete change to Lori, the few rough spots in his gestures were completely gone, he was smiling, laughing and enjoying himself as a pretty girl!
Halfway through the meal I had a familiar urge. "Ive got a problem Sue, I have to use the restroom," I whispered.
"So do I mom, cmon lets go." Craig volunteered in a cheerful voice. He grabbed his purse, stood up and looked at me. "Coming?" He asked. Sue smiled at me. "Its up to you but were not going home for a few hours."
Pretty dresses, sexy lingerie, men smiling at me, all that I could handle. Using the womens restroom though was a terrifying step. If I was discovered Id probably be arrested and branded a pervert, dinner was one thing but the bathroom was another world altogether.
"I cant wait mom. You can hold it if you want." With that he smiled, turned and began walking towards the restrooms. I thought about it for a second then quickly grabbed my purse and hurried off to catch up with him. We waited in line for several minutes with other women but we were more interested in each others outfits than anything else. When my turn came I casually walked into a stall, locked the door, did what I came to do and resisted the urge to do a victory dance. I was a woman in a womans world!
Craig was waiting for me at the sinks touching up his makeup, I joined him and we smiled sharing another special mother daughter moment. I touched up my lipstick, brushed my hair, then carefully smoothed out the wrinkles in my skirt. I wanted to take my time and enjoy myself but my dinner was getting cold and Craig wanted his desert. I tucked away the memory of my first time in the Ladies room in a warm spot of my heart to be treasured always then followed Craig back to our table. Sue gave me one of her smug looks but it didnt matter, I crossed my legs, straightened up and smiled at a man at a nearby table.
We had a great evening and when it was all over Craig and I carefully hung up our dresses, put away our lingerie, slipped into our nightgowns and fell asleep listening to the wonderful sounds from our tape decks. Sue had explained that once we listened to the first minute of the first tape we would be hooked and feel that we just had to listen to all of the tapes. It was so exciting to think that listening to those tapes was turning us into women and we couldnt stop it! When we woke up the tape would have done its job implanting suggestions on our brains and pushing us further along the road to becoming women.
The next day was Saturday and Craig was thrilled to be able to spend an entire weekend as a girl. He came to breakfast in a very pretty black and with dotted dress with a two tiered skirt, tan stockings, and black skimmers. his makeup was just right for the shopping trip we had planned for the afternoon He seemed completely at ease in his pretty outfit and the gracefulness and gestures from the night before seemed to have carried over nicely, he did everything just the way any girl his age would. I was dressed in a pretty pink floral, ankle length skirt that caught my eye when I went to find something to wear that morning. I looked over the many dresses and skirts in my closet without finding anything that appealed to me until I saw that skirt. It looked very pretty and seemed like it would be comfortable to wear so I paired it with a pink nylon shell top and a pair of pink skimmers. I considered wearing my usual sexy lingerie but I felt drawn to a pair of plain white nylon panties, a simple bra with lace covered cups, a long half slip and a pair of tan pantyhose. I felt odd pulling on the pantyhose, I preferred the sexiness of a garter belt and nylons but my legs looked just as pretty and it felt nice to have my whole lower body encased in nylon. I slipped the straps of my bra onto my shoulders and was pleased to see that even with an everyday type bra on I still looked enticing! My slip gave me an added bonus, the sensuous feeling of nylon against nylon as I moved. It felt so phenomenal that I found myself wondering why I had never tried something like this before. Why hadnt Mary had ever mentioned the wonderful feelings produced by putting nylon and satin against the skin? If men knew how erotic it could be to wear lingerie I doubt theyd ever buy another pair of cotton briefs again! How could anyone not enjoy feeling sexy and pretty?
I looked great in the skirt but the shell was just a little too sheer until I slipped on a pretty lace trimmed camisole. What a fantastic garment, the lace pattern was visible under my top yet hid my bra effectively. Id have to pick up a few more, a woman couldnt have too much petty lingerie! I slipped my top back on , brushed out my hair, then went to work on making my face match my outfit.
That wasnt too tough, a light pink blush, coral lipstick pink eyeshadow blended with white were very effective at drawing out the pink from my skirt and the white from my top. I carefully stripped off the red nail polish I had on and replaced it with a shade of pink that matched the flowers in my skirt. I smiled to think of how well Id mastered the art of using makeup and nail polish in only one short week. I had watched Mary do it many times but it never seemed to sink in, until now.
Craig was generous with his compliments about my outfit but I could see that he was getting very anxious to leave. My son who hated the idea of shopping for clothes now couldnt wait to get to the mall and shop till he dropped! Craig had a major league shopping list. He wanted to buy some makeup, new outfits he had seen advertised in his Young Miss magazine, and of course a couple of necklaces, some rings, and a bracelet or two, the typical wants or should I say needs of a sixteen year old girl. Craig shopped like a real pro, hed spot an outfit that he liked in his size and add it to the growing collection of outfits he selected to try on. Hed select the best from the choices he made and hurry off to the dressing room with the maximum number of outfits that he could take in with him. occasionally hed come back out to ask our opinion about a dress but for the most part he made his choices then came back to choose the next load. Sue was nice enough to wait with Craig in the Junior size department so that I could enjoy myself in the ladies section. The styles in the junior section were very pretty and eye catching but they just werent right for a woman my age. I needed dresses that were just a little longer and a little looser than the ones Craig liked and the lingerie I preferred was much sexier than I would consider allowing Craig to wear. His cute little bikini panties were nice but they were just no match for the black lace bikini panties that I loved to wear and he was far too young for the strapless push up bras that I was buying as a little treat for myself! We shopped in every store that sold womens clothing or jewelry and by the time we finished I as trying to imagine how I was going to pay my credit card bill! When I mentioned my concern to Sue she shrugged and told me that Id be making more than ever before and that she was sure Id have no problem paying my bills. I briefly wondered what I was going to do with all of the clothes I had bought but then it occurred to me. Id have to work throughout the summer to pay my bills and get back on my feet so why not just work a little longer to make use of my new outfits! It was amazing how well things were working out, problems just seemed to resolve themselves!
That evening Craig and I put on a fashion show to model all of our new outfits. We had a great time choosing outfits, coordinating our makeup and nail polish, mixing and matching skirts with different tops, pretending to be models at a fashion show. We were just about ready to end when Sue surprised us with several pairs of slacks and shorts that she had bought while we were in the dressing rooms.
Those slacks meant so much to me and Craig, Sue was telling us that we had mastered our lessons in passing as females. It was sort of ironic that we had to master wearing dresses before we could start wearing pants but Craig and I both saw it as the compliment Sue meant it to be and were about to model our new slacks when she stopped us.
"Those pants are going to be pretty tight, I think you girls will be needing these." With that she tossed each of us a package containing what looked like an athletic supporter. "Directions are inside, read them carefully." I stared at the package in my hand completely baffled at what it contained. The pink label with flowers on it said "1 Tuck-em-Up Belt" but the paper with directions was folded over preventing me from learning any more.
"Dont just stand there ladies," Sue urged. "The directions are very good, but read them carefully to avoid a good deal of pain." I had a lot of questions but Sue wasnt in the mood to answer them so Craig and I took our slacks and other gift and went to change.
I couldnt believe it when I opened the package and read the directions. What looked like some sort of athletic supporter was designed to hold my genitals inside my lower abdomen. If I followed the directions properly I was promised a smooth flat front that would appear perfectly normal in the tightest pants, or even a pare of panties! I quickly removed my clothes and with trembling hands I pulled on the belt. I followed the directions carefully tucking my genitals up into my lower abdomen and then allowing the wide elastic band of the belt to fit snugly against the opening to prevent anything from coming back out.
I gasped for breath as one of my testicles sprang loose at the last second and got pushed in by the belt. The directions said it might take some getting used to but I had no idea I was going to have to get used to being slowly castrated. I did my best to adjust everything to relieve the pain then slipped on my panties and looked in the mirror.
I was incredibly happy to see no sign of the bulge that had previously marred the look of my prettiest panties. I turned from side to side, checked over my shoulder, and still there was nothing. No bulge, no lump, just a woman in a pair of panties! I pulled on a pair of jeans that were nearly skin tight and to my delight I was able to get them zipped without any trouble at all. The best part of it was that I looked fabulous in those jeans! My butt seemed to be molded perfectly as were my hips, and the jeans tapered to my ankles making my legs look nearly as good as they did in a dress and nylons.
I knew exactly how I wanted to look. I removed my jeans, slipped my pantyhose back on along with the shell and camisole I had worn earlier. I slipped my feet into a pair of red heels, redid my lipstick and went out to let Sue see her sexy little sister.
Craig had beaten me to the punch and was busy modeling a pair of short shorts and a midriff top for Sue. He looked so cute in tight white shorts which emphasized his butt and hips, his top bulging just right over his bust then showing off his tight stomach and small waist. He had his hair puled back into a high ponytail and wore a pair of white girls socks and a pair of pink and white sneakers. He looked sweet and innocent, a girl ready for school to end and summer vacation to begin and that was exactly what he had become. I have to admit that I stole the show though, after all a good looking woman in tight jeans, heels, and lipstick that screams "Kiss me" can not be ignored! That day was another turning point for me and Craig, we could now dress casually which opened up new worlds for us to explore.
You dont often see women at the grocery store or running errands in dresses and you rarely see girls Craig age in dresses unless its a special occasion. We were limited to wear we could go when we could wear nothing but dresses but now with a little help and our belts we could plan mother daughter outings to remember!
It took an enormous of amount of determination to get used to wearing that belt but Craig and I were both very determined to pull off this little charade. I couldnt wait to start earning a living gain and getting on with my life. Id be getting on with it in a skirt and heels but it had to be better than sitting around vegetating. Craig and I wore our belts day and night for three full days until we could honestly say that we didnt notice it anymore. We each had our own reasons for being so determined, I wanted to be able to go shopping for groceries without looking like Donna Reed and Craig had his heart set on a bikini.
It was a warm spring day and time for my debut. I had been spending way too much time indoors doing housework and learning to type with nails and now it was time to enjoy the fruits of all of my labors. I slipped into a pair of tan pantyhose, threw a white knit top on over my bra, then tugged on a pair of tight jeans before stepping into a pair of blue flats. I applied a minimum of makeup to avoid attracting too much attention, brushed my hair, sprayed on a little cologne, and then it was off to the store. I was taking a big chance driving alone dressed the way I was with a drivers license that said my name was Steve and my sex was male but I had to do it. The danger only intensified the excitement.
After turning off the car I spent a couple of seconds checking my makeup and fluffing out my hair before I opened the door and stepped out. I wont lie and say I breezed right up to the store because truthfully I was scared stiff. It was a matter of minutes before I could get both feet out of the car and stand up. I checked my purse several times to make sure that I had my keys before I finally locked and shut the door. Just then a car pulled in next to where I was parked, a whole parking lot with empty spaces and this person wanted to be next to me. How lucky could I get?
I shouldnt have wondered. No sooner did I get to the other side of the next car than the door opened and acting on a reflex I turned to see who was coming out bringing me face to face with another woman. I smiled and nodded while we did a mutual comparison of how we were dressed. I must have passed her test since she kept walking and I was left wondering how my legs had suddenly become rubber.
Another test, another passing grade, I found myself thinking as I entered the store feeling more confident about myself. I smiled at men and women I saw as I shopped and even had a young man help wheel my filled cart out to my car for me. As he helped me load my car I saw him giving me a quick appraisal and then smile obviously happy with what he saw. He was far too young for me, not much older than Craig with the same delicate build and facial features. I couldnt help but wonder if hed look as pretty as Craig did in a dress.
I monopolized the conversation over dinner that evening with tales of solo trip as a woman. Sue seemed amused and Craig jealous but I couldnt stop going on and on about how great it was to walk around a store filled with people while I looked like a woman. I was truly hooked at that point and began to plan more and more trips to pick up a few things at the grocery store, fill up my gas tank (Three times in one week!), or anything I could think of to go out as a woman.
The last week of Sues visit was a hectic one, she wanted to make sure that Craig and I were on the right track before she left. John wouldnt be here for a few weeks and she was worried that we might change our minds in that time. Just to make sure nothing would change sue got rid of every piece of mens clothing that I owned and left Craig just enough for school use. She also gave me another series of tapes to help reinforce my feminine feelings and encouraged Craig to wear some of my lingerie from time to time knowing that a simple thing like that would be enough to keep him hooked..
Craig and I were in tears when we took Sue to the airport for her return to California. We hated to see her go, shed changed our lives so much, yet we knew that very soon wed be joining her to start a new chapter in our lives. Craig and I both wore short denim skirts with roll down socks and white sneakers. I wore a pink jogging top for comfort while Craig preferred a long sleeved, white cotton shirt to look stylish. After Sues plane had taken off I decided to treat Craig to a little lunch so we stopped at a fast food outlet near the airport. Thanks to my twice daily use of the "Girl Talk" throat spray and gargle Sue had provided my voice was settling into a normal pitch range for a woman so I did the ordering for both of us. Craig would nod or give an occasional one word answer while trying to make his voice sound more like a girl. I was sure that once he started using the "Girl Talk" his voice which was just on the high end of the range for boys his age would settle into a very pleasant sounding girls voice in a short period. Once his voice settled properly I knew hed quickly overcome his fear of being read, no one was going to think a sweet young thing with a voice that sounded like sweet music could be a boy!
"Mom, Im kind of scared," Craig whispered as we ate. "I never thought something like this would ever happen and Im not sure whats happening to me."
"But I thought you enjoyed this sort of thing Lori. I didnt notice any hesitation when you were trying on different outfits last week." I wasnt sure what could possibly be bothering him but even as his dad I would have been concerned.
"Sort of, " He said, almost on the verge of tears his voice breaking. "I kind of got started fooling around with moms clothes and that was sort of fun. Mom bought me a few things to wear and we sometimes pretended that I was a girl but I never thought..."
"I never did either honey," I wanted so badly to hold him tight and tell him that everything was going to be fine. "This is all completely new to me too. Whats scaring you so much?"
"Well its just that up to now its been just fooling around, now its getting to be real!" He whispered frantically. "I mean look at me, Im out in public wearing a skirt and a girls shirt, Im wearing a bra and girls underwear and thats not even mentioning the fake boobs!"
"You look perfect honey, no one thinks youre a boy. Dont let it worry you."
"But mom, thats the trouble!" Tears began to form in his eyes. "Even I dont think Im a boy anymore! At least Im sure not thinking like a boy." I handed him a tissue from my purse to keep his makeup from running and listened patiently as he explained how hed been noticing more and more changes which he couldnt seem to control. He told about how he no longer found girls attractive, he was interested in their outfits, their hair, and makeup but not them. Boys on the other hand were beginning to get to him. A few boys hed gone all through school with were now looking more and more interesting to Craig. He found himself daydreaming about what it would be like to go on dates with these boys, to have them put their arms around him and hold him, and especially what it might be like to be kissed by them and to kiss them!
"I understand completely Lori," I said trying to ease his fears. "My sister said that this was going to happen, its all part of what has to happen to us by this summer. I have to become a woman and you have to become my daughter. Between the hormones weve been taking and those tapes we listen to we dont have much chance at remaining males."
"You mean those tapes Aunt Sue gave me did this to me?" Craig was shocked and I was stunned. I thought that Sue had explained everything to him. "Why didnt she tell me what theyd do to me?"
"Im sorry honey, I honestly thought you knew what was going on. The pills youre taking will put your male hormones on hold for a while and make you feel a little different but the tapes were meant to really make you think of yourself as a girl."
"God, did they ever!" Craig exclaimed. "Friday I told a girl that she really looked great in her new outfit. She just looked at me kind of weird like and walked away. A couple of days before that I saw this really pretty dress at the mall and I wanted to try it on so badly that I almost cried!" "I understand completely," I said with a laugh. "A couple of days ago when I woke up I just had to wear some of the sexiest lingerie I could find! That was the day I wore that red dress with the Take me now pumps. One night of listening to those tapes and I ended up in the cutest little Babydoll nightie. Now when a man looks at me I just enjoy it and smile at him. I dont seem to have any choice, its just what happens." "But how do you feel when a guy looks at you like that?"
"I feel wonderful, sexy, and feminine Lori, just the way youre going to feel. I work very hard to look pretty and its nice to see that its appreciated. Its not easy picking out just the right outfit then doing my hair and makeup just right. If men didnt look Id be upset!" "And if a guy asked you for a date?" Craig asked with a smile. "Thats a good question," I answered. "I dont really know what Id do. I guess Ill cross that bridge when I come to it. Youll probably have plenty of chances to decide for yourself."
Craig was so busy baiting me that he had forgotten that he was going to be a blonde haired, blue eyed, boy magnet!
"What am I going to do if a boy asks me out?" His voice cracked with uncertainty.
"I think that if you just quit worrying about it everything will work out okay. It certainly has for me, I hardly ever worry about going out this way, it seems perfectly normal for me to look like this. Its going to be tough for a little while longer and then well be out of here." I told him in as soothing and motherly voice as I could muster. "Of course once we move you wont be able to switch back until I can pay off some bills and get my act together. Until then its strictly my daughter Lori, okay?" Craig nodded his agreement even though he was still unsure of what was happening to him. That wasnt terribly important right now though, after two weeks I knew that he was bound to be hooked on those tapes and day by day theyd make him more comfortable with being a girl. He couldnt possibly back out now.
Craig and I worked hard on perfecting our femininity over the next month, I went about my normal daily routine as Jacki and when he wasnt in school Craig had no further problems becoming Lori. We went to a few movies, did some shopping, and even got Craigs ears pierced. His hair was long enough that his ears were usually covered so we were confident that no one would notice. Craig was thrilled and never once questioned taking another step towards becoming a girl.
It was getting towards the end of the school year and Craigs class was putting on a little play which the parents were invited to attend. Since Mary died I hadnt been able to bring myself to go to any social functions or even school meetings. I knew that bothered Craig so that night while he performed his Aunt Jacki was right there in the front row offering him moral support.
Wearing a white silk pantsuit and heels I had a lovely time, Craig took me to all of his teachers and proudly introduced me as his aunt. Everyone was very sweet and understanding when I told them that his dad was down south beginning a new job and that I was looking after Craig until he could join his dad. One of his female teachers confided in me that what Craig really needed was a womans touch, his dad was doing his best she said but it would be better if there was a woman to help. I wholeheartedly agreed and assured her that I was doing all that I could to add feminine touches to Craigs environment and that come summer I was sure there would be many changes for him.
Later that week Sues fiancee John came to help me and Craig prepare to move. We met him at the airport and I recognized him immediately since he looked just like the John I knew. No dress, no makeup, nothing feminine at all to my shock. I felt slightly silly standing there in a pale lavender colored blouse and white skirt.
"Excuse me," He asked hesitantly as I approached. "Are you Jacki Windmark?"
"Yes I am," I pitched my voice to be as soft and sweet as the smile on my face. He hadnt recognized me at first, even with a picture of me in his hand. "Im Jacki and this pretty young lady is my daughter Lori!" Craig and I each got a hug and peck on the cheek before we gathered Johns luggage and went to my car. We were about to load his luggage into the trunk when a young sky cap appeared at our side.
"Could I be of some help?" He asked politely as he smiled at Craig.. "The airline doesnt think passengers should have to struggle with their luggage and I agree with them." He hefted Johns cases into the trunk as if they were filled with feathers. Why couldnt I do that I wondered. When I had tried to lift one of his small cases I found it far heavier than I expected yet this young man could pick it up with ease. Could I have changed that much in a few weeks? I gave the young man a generous tip for his help but I noticed that he seemed to prefer the smile from Craig much more!
"Oh mom, he was so cute!" Craig giggled a