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Becoming A Prom Queen
🕑 Added 2020-05-21 05:28:08 +0000 UTCSUMMARY - Tim moves in with his Grandmother who decides that since he likes to dress he will have to follow her rules. Grandmother makes him go farther than he ever expected to go.
My name is Tim Grant, I'm 17. I live with my Grandmother now because my parents wanted to retire to another state, and since I still had my Senior year to go in high school, I wanted to stay here. Without my knowledge, it was arranged that I would stay with my Grandmother. She is in her fifties, a slender, beautiful woman with blond hair going gray. She and I always got along well even though she's a snob. She has money, lots of it, and lives in a huge mansion segregated from the city by a tall stone wall with only the huge iron gates by the street as an entrance. When I was younger I loved to roam around the house 'discovering' things, but I had not been there in several months now. When I was told about the arrangements I carefully packed my things, and dad and I moved them into Grandma's house. Fortunately, none of the boxes popped open, and my sisters' clothes remained a secret. I spent all day setting up my room, hanging up my clothes and filling the dresser, and so on. That night at dinner my Grandmother she shocked me to the core when she told me that she had a garden club meeting the next afternoon, and wanted Clarice to go with her!
In tones that left no room for either discussion or debate, she told me what she wanted. "As you know I live here all alone, and I was eager to have you here with me. However, when your mother told me about Clarice I knew that having a girl with me would be more fun than having a boy here. If you, as your mother insists, dress as a girl once in a while, then I will allow you to do the same here. There are a few rules of course." Her silky soft voice mesmerized me, and her decision to let me dress up once in a while made me smile. "One, as a male you will wear not pants that require a belt or have a zipper in the front. Two, whenever you are dressed as a female you must present yourself to me for approval. Three, your typical male bulge must never show at any time. And finally, you must let me help you in your appearance whenever you decided to dress as a female." It sounded easy, and without any discussion or listening carefully, I agreed. "Now that we have that settled, why don't you go get dressed and let me meet my Granddaughter?"
It was the style, and I had let my hair grow quite long, and I now had silky blond hair that just reached the middle of my back. I had been 'out' with my sister a few times, and I knew that I was reasonably passable as a girl my age if I was careful, and had long ago learned to cope with the fear that I would be discovered. When I was dressed I looked pretty good, and I knew it. Little did I know then. As I rose to leave the room and change, Grandmother said, "The party is at three, so I want you ready by two. A nice summer dress will be okay Clarice." I said nothing as my Grandmother smiled that enigmatic smile she has.
I found out that if I pin my hair back with a barrette, put on lipstick and blusher a bra and a pretty blouse, not many have been able to tell I'm a guy. Because of that, I was filled with myself as I went to my bedroom to lay out the clothes I would wear to show her just how nice I looked. I returned to my room to get ready with a smile on my face. During the last year, I had found several sites on the Internet that sold things to make men into women, and with my allowance, I had bought some very realistic breast forms, the kind you glue on. The problem was they stayed on for ten days at a time. Since Grandma had started this, I intended to do my best, and undressed. I started by putting the bar on and carefully slid the breast forms into it. After I smoothed out the bra it looked like I had boobs of my own, and smiling, went to the bath to shave and wash up.
I had to set up my makeup on the small counter but managed to do my makeup for the day. Light foundation, then powder, and some light pastel eyeshadow with soft brown eyeliner both above and under my eyes. On my cheeks, I used a blended peach/rose that I made up myself. Everything else waited until I was dressed. Ever since my body started to grow hair everywhere I didn't want it, I had shaved or used a cream hair remover to keep my skin soft and smooth. I usually did it once a week, on Wednesdays, so my skin was still hairless and soft to the touch. I slipped on my panties, and then some shorts. The bra was the thin pink one, lace-trimmed, with demi cups in 34 'A'. The pink shell top went over my head and I let my hair cascade straight down, framing my face in a halo of golden blond. I walked down the stairs and saw my Grandmother out on the patio, and walked out to her. It was the first time she had ever seen me dressed as a girl. "Good morning Clarice! You look very lovely today!" I stood across from her and waited. In a moment she also stood and looked me over very carefully.
"Well, you look a bit like a girl of course, but your posture is terrible, and those nails! You need to have your hair attended to as soon as possible, and when you walked out here it was obvious that you still walk like a boy. We can't do anything today, well, maybe a few small things, so I will lay out some clothes for you to wear today, and starting in the morning we'll work on the rest. Okay?" I nodded my head yes and turned to walk away when she stopped me. "Clarice!" I turned, and she told me that young girls always curtsy when they enter or leave the presence of an older woman! "I curtsied the best I could, and she waved her hand at me to leave. I did not see the slow smile that came to her face as I walked back into the house.
On the bed was a pile of clothes, that obviously the housekeeper had put there. As I looked at them I wondered how I would even get them on! Piles of lace and chiffon in pastel yellow and white, and under that, a corselet, hose, and panties. I undressed and changed panties, carefully 'tucking' myself like I always did, and wrapped the corselet around myself. I just barely managed to get the hooks fastened, and even then it was tight. I felt the laces in the back and was just trying to pull them when Mrs. Handle the housekeeper came in. "I'll help you with this. You need to be this small to fit the dress dear, standstill." She tugged and pulled while I grunted and moaned, but she kept at it until my waist was a trim 21 inches. Then she reached into the front of the corselet and pulled my skin up and massaged my flesh until she was satisfied. When I looked down I saw that I had boobs! She had me sit on the bed and put the hose on, then helped me fasten the garter tabs and pull the tension tight. "Your makeup is almost right, let me help you." She added some mascara and made my blusher a bit redder. The dress was slipped over my head and buttoned-up, from the waist to my neck. It had long, sheer sleeves, a round neck with lace trim; it swelled over my new boobs and tapered to my now skinny waist and flared out in a skirt that was full and had two lace petticoats under it. I stepped into the white heels and turned to look in the mirror when Mrs. Handle slipped the pearls around my neck and fastened them. She handed me a bottle of perfume and told me where to use it, then she gave me a soft pink lipstick. "Sit here please Clarice." I sat, and she braided my hair down the back, using a yellow ribbon, ending with a bow at the very end.
"That looks a little young for me doesn't it?" She harumphed, kept working, and merely told me that girls my age always wore ribbons in their hair. "Carry this Clarice.: She handed me a small white clutch bag. "Your Grandmother is waiting on the patio for you. I do not suggest that you keep her waiting." Walking in a dress that big was new to me, but Mrs. Handle told me how to hold it up when I walked down the stairs, and I made my entrance to the patio as gracefully as I could. "That's so much better Clarice! You look simply marvelous! Shall we go?" It was a rhetorical question of course. Her driver took us to the garden party, where I was introduced to everyone as her Granddaughter, Clarice. It lasted several hours, and by the time we returned home my waist was killing me. "You did very well today Clarice. A bit awkward now and then, but very nice for a boy in a dress. You may change if you wish. Dinner will be in two hours."
Mrs. Handle was there to untie the laces for me and help get the dress off, then I washed off the makeup and went to my closet to get some jeans. They were all gone! I picked out some tan slacks and immediately saw that the zipper went up the back! I looked at all of the rest of the slacks and all of them had the zipper in the back, on the side, or were elastic at the waist! I pulled the tan slacks on and saw that they were tight on my waist, hips, and butt, and in front, my male bulge pushed out against the material. Then I remembered her telling me the rules. All of the slacks I had were for women! I once again 'tucked' myself and fastened the slacks up and reached for a shirt. A simple white shirt is what I wanted, but what I got was a simple white blouse. It had a round neck and short sleeves that puffed at the shoulders! That's when I knew just how devious she was. Even the loafers were gone, in place of them were flats. I slipped my feet into them and joined her in the parlor.
With my hair still in a braid, I looked like a girl and I knew it just as she did. "I see you found something to wear." "Yeah, but they're all girl's clothes!" With breaking her smile, she sat back and looked at me. "Remember the rules? No pants with a front zipper or a belt. You agreed, so I merely supplied you with slacks that met that criteria!" "Yes but." "You may wear a skirt if you wish, or whatever else is in your closet. I will not force you to dress as a girl, of course, I merely made sure that you have clothes compatible with the rules. If you wish to wear slacks and do whatever it is boys do, you may do so." She had managed to maneuver me into a Hobson's choice. Wear women's slacks and blouses, and do whatever I wanted, and probably be beaten to a pulp by the local guys, or dress as a girl and at least look normal! "You tricked me!" "No dear, I did not! I carefully explained the rules and you agreed to them. Now quit complaining, please sit down, and let's talk about what we should do now."
In my heart, I wanted to dress as a girl, and now was my chance; I just didn't want to tell my own Grandmother that! "Your sister told me that the two of you had been out, with you dressed as a girl several times, and that tells me that you like dressing as a girl, so do not try and deny it. I am willing to let you continue to dress as a girl, and I will not force any changes on you. You will have to ask me for any help that you think you need. If it's reasonable I will see to it that you get what you need. In return, all you have to do is abide by the rules I gave you. and you agreed to." I was a bit angry, but sat there, holding it in, waiting. "Do you want me to help you?" If I said no, I would never be able to leave the house without taking a terrible ribbing, and if I said yes, there was no telling what she would do. I really never had a choice and she knew it. "Just what did you have in mind for help?"
"There should be no reason other than illness, that a girl your age should need a corselet to wear the dress you did today. You need to be enrolled in a class to help you lose weight. I noticed at the garden party that you tried your best to be as feminine as you could, and you did very well, but you had to work at it. Femininity should be natural, not forced, so I think some classes in poise and grace, and of course, if you don't need the corselet, you would be forced to use those silly bags of silicone. Since very few girls your age need breast forms, maybe a little help there too." She leaned forward and looked me right in the eye. "I take an aerobics class every day at eight in the morning. You can join me. I'm sure they can get you down to more proper weight for a young lady your age. I also have a friend that can help in your grace and poise. As for the rest, you would certainly have to agree to that in person." "This aerobics class, do I go as Clarice or Tim?" "That's up to you dear, but You might want to try on your exercise outfit before you decide. You'll find it in your room. But if you decide to go as Clarice, we might of course want to see about taking care of your bustline first." I went to my room and found the outfit, and wasn't all that shocked to see that it was a tight spandex outfit, all in pink and purple. I was almost ready to cry when my Grandmother walked into my room. "Good! I see you found it!" "Why are you doing this to me?" "I am not 'doing' anything to you at all. I gave you the choices and you made them. You can always leave of course, but where would you go? With your parents? They moved away to enjoy their retirement. Your sister? She has twins in a small house and a husband to take care of. When you went to the garden party dressed as a young girl you admitted that's what you wanted to be, don't you see that?" She stepped up and wiped away the tears in my eyes and hugged me.
"If you want to be a girl, I promise you that you will be a true lady, in every way. But we cannot continue fighting and throwing insults back and forth. Now tell me. Do you want to be a girl your age?" "Can I dress my age?" "Of course!" I nodded my head yes, collapsing on her shoulder. "Now that we have that out of the way, let me call the doctor." "What will he do?" "I don't know Clarice, we'll find out together I guess," Grandmother called, then told me I had an appointment in the morning. "We'll skip aerobics tomorrow, but be ready to go by nine. Mrs. Handle will lay out your clothes for you again." "I can get dressed, Grandma." She looked at me for a minute and then nodded her head.
In the morning, knowing what was in store for me, I wore a skirt and blouse, minimal makeup, flats, and my hair in a ponytail. I at least looked 17 now. Grandma was in the parlor waiting for me. "You look very nice dear, eat your breakfast and we will go.
The drive didn't take long, and I was soon in a doctor's office surrounded by the aroma of a medical building. My name was called and we went into the small examination room. The situation was explained to him and he asked me to undress. I got a physical, and when he was all done he called Grandmother back into the room. As I understand it, you want me to give her a bust more in line with a girl her age, is that right?" "That would be a helpful doctor. "I need to keep her for most of the day. Can you come back at two?" "Of course." She left, and the doctor took me next door to his small clinic. I was given a paper gown and told to change, and without any explanation at all, he gave me a shot in the arm. After that, nothing until I woke up.
I didn't feel sore at all, but the way the sheet tented I knew that I now had breasts; the only question was, how big? The nurse came in and helped me sit up, then walk to the bath. "Your clothes are on the hook dear, you can get dressed it you like." I did. When I removed the paper gown I saw them for the first time. Small, but pert and perfect. Twin mounds that no boy ever had on his chest. I felt them with my hand and they were soft and pliable the nipples tender. I saw no scars or stitches until I pulled my panties on. My navel had two small stitches. But the biggest shock was that my waist seemed to be smaller, which was confirmed by the way the panties fit me. My hips seemed larger somehow, yet I had no idea how he did it. The skirt also fits better, if loose, and my bra fits me perfectly. The way it held my breasts up was a new sensation, which I have to admit I liked.
Grandma took me home and insisted on seeing the doctors work once we were in my bedroom. I undressed to my panties, and she carefully examined me. "He told me that he took almost five inches from your waist. Said it was excess fat anyway and used it to create your breasts and make your hips rounder and fuller." Then she used a measuring tape to find out my correct measurements and wrote them down. "It looks like you need all new sizes of underwear Clarice, how about you and I go shopping tomorrow and get what you need? "Yes!"
Once she had left I knew that I had to do something about my male bulge, and went into my bath and found a roll of flesh-colored medical tape and some bandages. I found the scissors and set about making my maleness go away. But first, I had to shave my groin and genitals. Yanking tape off somehow might be painful if I left the hair on! Once that was done I cut a small rectangular out of the bandage and made a slit in the tape after cutting a piece a foot long. I split the end of the tape, and with the bandage, pushed my testicles back into their sockets and held them in place with the tape, then covering the tip of my penis with some cotton, I pulled the tape up, pulling it back into my body. I secured it to my skin tightly and checked to make sure I could urinate easily. I could, and when I put my panties back on it looked as if I had a small cleft of the female sex. I pulled the tight tan slacks back on and joined Grandmother for dinner.
In the morning I slipped into the aerobics outfit and after breakfast, joined the class. It was the first time I had ever seen my Grandmother in anything but an almost a formal dress, and she was a stunner! She had a lithe, agile body, perfectly proportioned and well-toned. I almost died during the workout while she was barely breaking a sweat! After a shower, she drove us to the mall, where she surprised me again. To me, in my fantasy, I had been in a salon with a girl making my hair in a special style, like for prom, and the even greater ecstasy of having someone do my makeup. Curled hair, a pretty updo, and a frilly pink prom formal. The only time I had even been in a salon was with my mother or sister because I was scared to have them touch my hair. I had been shopping exactly once as a girl, and even then I had let my sister lead the way and do all of the talking. Now, my Grandmother had made it possible for me to go shopping, with her, and not have to worry about it.
Grandma didn't say anything about the way I looked in the exercise outfit, so I assumed she missed it, but on the way to the mall she mentioned it, and asked me how I managed it. When I told her she giggled! I had never heard her giggle before! "Inventive anyway Clarice! I hope it's comfortable." "It is Grandma, at least it has been so far." I had worn a sundress that was backless with a single strap that went around my neck holding up the square-cut neckline, and flats, my hair in a ponytail. "I called the beauty salon and made appointments for both of us Clarice. I told them that we both wanted our hair, nails, and makeup was done because my Granddaughter was going to make her debut today." She led the way in, and I was soon getting the works.
During the next two hours what happened to me surpassed my wildest expectations. I was treated just like any other girl as my hair was washed and a perfumed setting lotion was applied. My hair was then rolled, twisted, and twirled in hair curlers of every possible size and shape. I sat under the dryer as a manicurist came over and cut and filed my nails, then put a reddish-pink polish on my nails that perfectly matched my lipstick. After my rollers came out, she spent a half-hour trimming, brushing, and teasing my hair. I was sent to another person who did my makeup. When she was done and turned me toward the mirror, I almost fainted in joy. My face was that of a 17-year-old cover girl. I looked like I should be doing commercials for bubble baths, perfumes or lipsticks, clothes, or sexy cars. My makeup was flawless, pink-toned with a blusher that gave me prominent cheekbones. My eyes were wide and innocent, shadowed with blue to match my eyes, outlined in black to accent the almond shape. My lashes were upswept and thick with mascara. My lips were full, soft and a bit pouty, creamy in reddish-pink lipstick and gloss. My entire fantasy had come true! My hair had been set in a perm, making waves down the sides of my face, with tighter curls that cascaded down the back to just above my shoulders. Both of my ears had been pierced and small gold hoops hung from the lobes, swinging free as I moved.
I actually gasped when I viewed my ringlets and cascading curls, and the stylist giggled. "It looks darling on you!" Then she proceeded to make an adjustment on the right side. To my delight, she had selected a small pink satin hair ribbon set on a gold filigree flower barrette and pinned it to my hair. It was perfect! The ends of the satin bow sat streaming, settling softly against my hair. I thought it was wonderful, and stood up to look in the mirror. My Grandmother smiled at me from over my shoulder and asked if I liked it. "Oh yes, Grandma! Thank you!" "We have a long day ahead of us Clarice, ready?" I was.
"After we get you some undergarments of the right size, why don't we get you a pretty dress for the Spring dance at the country club?" It was all I could do to stop from yelling Yes! By the time we reached the dress shop, my arms were aching from all of the packages, so it was a bit of a relief to set them down. We selected several dresses for me to try on. We went off to the dressing room, and when I was wearing just panties, pantyhose, bra, and slip, layers of crinolines were slipped over my head. Whenever I moved I crinkled! When I stepped out, Grandma was waiting with my dress, and as I reached my arms up, all that frilly material swept over me with a rustle, settling gently at my waist and shoulders. This time it was she who gasped. "Oh, but that is the prettiest dress," she said happily. First, she tied the satin ribbons securely at each wrist, then she moved to the back where she zipped me up and worked to tie the three ribbons on the sash. Then she reached under and smoothed my crinolines and gently arranged the tiers of pink, white and blue ruffles on the sweeping full skirt.
After everything was in place, she made handed me a lipstick and told me to redo it, Then with a purse sachet, she sprayed my wrists and neck with expensive French perfume and led me over to a full-length mirror. She looked at me carefully, smiled, then giggled, and said, "Is this what you had in mind Clarice?" She put her hands lightly on my shoulders and told me to twirl. As I did, the rustling and swirling of my crinolines and the gentle swaying of my curls were just too much. I began giggling uncontrollably, just like a schoolgirl. I looked up at her and said, "Gee, Grandma, this is wonderful! How did you know?" She ignored the question and I stood looking in the mirror. Seventeen and never been kissed." To which she replied, "That won't last long." She helped me change out of the dress and we made arrangements to have it sent to the house.
That summer I took ballet, for poise and grace, aerobics, and by the time school started I was 118 pounds with a 34-20-34 figure, and I simply could not go back to being my male self again. I went to a regular school, and wore that pink dress to the prom, just like in my fantasy.
