<This story is archived on Crystal's Story Site, but I've also asked permission to showcase it here as well, since it's based on one of the images I have in the Modified Covers gallery. (This one has a character named Jenny, also...hmmm...) - Jenny>
This story was inspired by the fine graphic artistry of Jenny North. Her grasp of the conflicts and impossible situations we sometimes find ourselves in, are without a doubt some of the best I have seen, as she brings a refreshing and sometimes funny peek into our secret lives. Jenny North's site is worth a serious look. Laugh, cry, or snicker all you want, but please, hope you don't end up on one of her magazine covers. This story was inspired by her cover entitled "After School Transvestite."
Jenny's site is tgfa.org, which is a link on Crystal Sprite's site: Storysite.org
A New Waitress
"You girls have it made! All you have to do is look good and wait for some guy to ask you out! We pay and you get all the benefits without doing anything."
"Listen, you big ape. I work six days a week just to have any money at all. That means that when I go on a date it costs me money--money I need just to have an allowance!"
"Right. Okay, you maybe, but not many girls have to do that, and I still say that you girls have it easy!"
Shelly, my sister Carol, and Michelle went into a huddle for a minute, then they stood facing me.
"Okay, since you seem to think we have it made, we'll make you a bet. We have a game this weekend, right? If we win the game, we'll pay you $300. But, if we lose the game, then you have to work my job, as a girl, wearing the same uniform I do, for a month, and I still get the money--tips and all!"
Nobody ever said I was the brightest in the school, and I proved it that day. Our team was the favorite by everyone, including the other team. So far, they haven't won even one game. This would be a snap, and both of those girls would pay for it. Just as I was about to say something, my buddy Greg walked up, and I told him what the bet was. Like me, he knew we were a shoo in to win. With him standing right next to me, I agreed to the terms of the bet. Carol very carefully said them again, and asked me if that was right, and I said yes. There was no way we were going to lose this game. We're ranked third, and they are in last place. Greg agreed with me, and we walked away knowing that the girls had made a dumb bet. Of course, our bet was all over the school the next day, spread by the girls no doubt, and I took a lot of teasing about it, but most people thought that I was in no danger. Only the girls were gloating. Even my teachers had heard about it, and one of them even wanted me to extend the bet. If our team won, I would get extra credit, which would put me in the top ten percent of the class, just, but if we lost, she wanted me to come to school as a girl, for the same month I would be working as a waitress. I was so sure of the outcome that I agreed to her bet right in class, which was also all over the school in a hot minute.
I stand about 5'7" in my bare feet, weigh about 140 or so, and I have auburn hair streaked with dark blond and green eyes. I'm 17 now, and just as cocky as any 17 year old boy. My buddy Greg was a constant companion, and a good friend, but twice he told me that I would makeup as a real foxy chick! I wanted to slap him. When mom found out what was going on, from my sister of course, I got no sympathy at all. She merely told me that if I lose, she would be the one to help me become a girl, and after all, a month isn't that long. Dad thought it was hilarious, because like me, he knew we weren't going to lose the game. Then mom told me that I would be quite pretty as a girl!
"Face it honey, you look more like me than Carol does. We have the same nose, chin, eyes and coloring, while Carol takes after your father a bit more. I think it's going to be easy to turn you into a girl!"
"We're not going to lose mom, no problem there!"
"We'll see, won't we?"
There it was. The bet, the odds, and the possible outcomes. There was no way I was going to lose, and I was going to enjoy watching those girls fork over a $100 apiece. I went to bed confident and sure of myself. When I got to school the next day I found someone had painted my locker pink, and there was a bra hanging from the lock, still in the package. I got a lot of laughs about that, but stuck it in my locker and went to class. The guys on the team assured me they were going to win, which was very reassuring. With two days to go before the game, still sure of myself, and now over confident about the outcome, I guess I was a bit cocky about it, which is when I was confronted by several girls on the cheerleading squad. They told me they wanted in on this bet. If we win the game they said, they would do my homework for the rest of the year. If we lost the game, I would have to become a cheerleader for the rest of the season! Why did everyone want to see me in a dress I asked myself, just before I agreed. How could I not? I mean, the game is a lock isn't it?
I was in the stands, watching as we rolled over them. We were ahead by 6 going into the fourth, and I almost left I was so sure we were going to win. But they intercepted a pass and ran to the 5. A short lateral pass, a mad dash, and they scored! The game was now tied, and I had an ugly feeling in my gut. They have the ball, and need only one point to win. The kicker hit it squarely and the ball soared high and right, but drifted back and crossed over the cross bar. We were now down by one, and there were only two minutes on the clock. I was on the edge of my seat as we accepted the ball at the 25, and our man began to run. He was hit by three guys, the ball squirted free, bouncing into the air, end over end. There was a scramble to catch it, and we tried, but their team ended up with the ball. In two plays they scored again with a field goal and we were down by four with less than two minutes to play. As the clock ticked down we moved the ball to the 40. A field goal would not win the game, only a touchdown. The snap, a long pass, a rush to catch it, then our man dropped it just as the whistle blew. We had lost the game! Lost! I looked around, and saw a lot of the girls pointing at me, laughing as they knew what was coming. So did I. The benches were all metal, so I couldn't sink into them, but I wanted to.
By the time I got home my sister was there, grinning from ear to ear. My mother wasn't very sympathetic, and told me that in the morning she would help me get ready, then turn me into a girl! Dad was there at the game with me, and also knew what was about to happen to me, but there wasn't a darn thing he could do about it. "A man sticks by his word" he always said, and I had made the bet all on my own. By the terms of the bet, I would have to work as a waitress for a month while attending school as a girl at the same time. But there are six more months of sports, and I had also agreed to become a cheerleader for every game from now until then. Mom saw the implications at once, and dropped a bombshell on me when she told me that I would probably have to remain as a girl until the end of the year since it would be to hard for me to keep changing back and forth, and with some games in the afternoon, there would not be enough time for me to change clothes! I protested, but the best I could get out of her was a "Maybe. We'll see."
All three of the girls were at our house in the morning. Shelly had brought one of her uniforms for me to try on, but I was with mom in her room, with very strict instructions that everyone was to stay away. I had no idea how to go about this, except maybe to just put the clothes on, but mom asked me if I really wanted to be such a clown while I was a waitress. I could do it that way of course, but I would be the laughing stock of the town if I did. Mom had me strip down, then covered me with a cream she said would removed all of my body hair, and she was right. After I washed my hair and shaved as close as I could, I stepped back into her bedroom wearing nothing but a towel. In her right hand she had a pair of panties. Pink panties. The idea of wearing them made me feel like a pervert, but, she insisted, so I slipped them on. They didn't hide much by the way. Then she showed me how to put on pantyhose, which much to my delight, gave me shivers as the slick nylon slid over my now smooth skin. Once I had them to my waist, she gave me a pantybrief to wear, then pushed a folded washrag on each side, to give me hips. My still damp hair hung limp as she had me sit at her vanity.
Mom didn't do anything but guide me through the mysteries of makeup. I had to do it all myself, because, she told me, I might as well learn how. First, foundation that matched my skin tone and a powder to make my face smooth and matte looking. Then eyeshadow in soft blue with gray over that, and lilac highlights. The hardest was the eyeliner, but I managed to draw a reasonably straight line on each eyelid, and outline each eye with a black pencil. It was starting to get scary as the face I knew so well became that of a cute girl! Mom was smiling while I was in shocked silence. Then she began to use her curling iron on my hair. Slowly but surely she made my mop of hair into a style that was not only feminine, but enhanced my face! That done, she wrapped a bra around me and fastened it in the front, drawing my fleshy chest up and into the cups, which she then padded with some small foam shoulder pads from one of her dresses. Next came the waist nipper that took my pudgy waist and made it a trim 26 inches! The slip was short and white with lace trimming. The dress she had selected from Carol's closet was dark green. The sheath dress was at mid thigh on me, maybe higher because I'm a bit taller than my sister. The vee neck and no sleeves made me look thinner, and there was no doubt that I have a feminine figure.
Without warning, mom used a pin to pierce my one ear, then slipped a large gold hoop into each lobe. A thin gold necklace went around my neck, then she handed me the shoes. I stepped into the black heels and let her move me to the mirror. My greatest fear had come true. I looked just like a girl. All traces of the face I knew so well were gone.
"Shall we go?"
"Mom…do I have to do this? I mean, just look at me!"
"Yes, I know. You're quite lovely. You should be very happy."
"But they'll think that I…"
"They will think that you're very pretty, and that's all! But maybe we should find a name for you when you're dressed this way. I'm certain that you won't want to use your own name. Do you have any suggestions?"
I gave it a minutes thought, then said "Janet", because I don't know any girls by that name. Mom merely nodded her head, took my hand, and led me out of the room. With my heels clicking on the hardwood floor I felt as if I were walking the last mile to my death. I was both ashamed, and inwardly happy, that I looked this way. Happy because I didn't look like a clown, and ashamed because I look so damned good! We walked into the familyroom together, and drew immediate gasps from the girls, a shocked "oh no" from my father, and a grin from my mother.
"Everyone, this is Janet."
It was all I could do to stand there quietly and let them stare at me. Shelly, the waitress, stood up and walked over to me. Her eyes looked me over from head to toe and back, then she smiled at me!
"The way you look? I'll have more tip money than I ever got! You look fantastic! I can hardly wait until Jenny sees you! She'll probably not want you on as a cheerleader!"
It was all I could do to stand there like that. Every instinct in my body was telling me to haul ass and change clothes as quickly as possible, but of course, no matter how much he might dislike it, my father would make me stand by my word, so there I stood. Carol wasn't grinning quite as much now that she has seen me, while both Michelle and Shelly looked at me carefully. The girls wanted me to go with them, to some hamburger joint I guess, but mom said no. My tenure as a girl didn't officially start until Monday, and "besides" she said, "She needs a few things of her own." All of the girls understood, but it went right over my head. My parents told the girls to leave, then mom told me what she meant.
"We don't share underwear, Janet. You and I are going shopping and get you a few things you'll need, like panties of your own, probably two bras, and if we can find it, a padded pantybrief of your own. That way you won't have to use washrags to have hips. I'll get you a handbag and we can go."
That was it. No discussion, no questions, nothing. I was going with her and that's all there was to it! Mom returned with a small black shoulder bag, handed it to me, and headed for the door, only stopping to make sure I was following her. I didn't like it, but I did it. That first step outside was terrible, and I quickly got in the car, and saw mom laughing at me!
"Quit worrying so much about this! You look just delicious, and if someone didn't know, they never would unless you tell them or give it away. Walk with me, take the same step I do, hold your elbows in and use your hands more. Stand up straight and act like you belong there, and you'll be fine. This might last a while Janet, so you might as well get used to it. Who knows? Maybe you'll end up liking it!"
Mom was way off base there, but I said nothing. At the mall it was all I could do to get myself out of the car, but as soon as we walked inside I started to freeze up, really. Mom gently took my arm, and started walking, and I had no choice but to follow her. She was walking normally, and I had no trouble keeping up with her. Only my pace was wrong. We went into lingerie, and mom picked up a couple of packages of panties and two bra, without asking me if I liked them or not. Because we now had what she said I needed, I expected to leave, but no. She went into the shoe department, pointing out that I would need to have some very comfortable shoes to work in at the restaurant, plus shoes for school and pair of gym shoes for cheerleading. The guy never batted an eye as I tried on the shoes for fit, although I'm pretty sure he tried to look up my dress once. From there mom took me to one of those makeup shops where they redid my makeup and mom bought what they used. As good as I looked when mom helped me do my makeup, I looked twice as good now. There wasn't one trace of my beard at all. I also had the feeling that my mother wasn't done yet, and I was right. She took me into the dress shop where I also bought two dresses and two skirts with blouses to match, and later, at a specialty lingerie shop called Freddie's, a padded pantybrief and a pair of breastforms! I was thoroughly embarrassed when mom dragged me into the changing room to try on those breastforms, but she said they were perfect, and I left wearing them.
By the time we got home I had lost most of my fear of being in public, but quite not all. Dad wasn't home when we got there and I assumed that I would be able to change, and I was right, but not into my jeans. Mom wanted me to try on both dresses and skirts. She unzipped me and I went to my room, put the first dress on, and went into shock. I had not realized how low the vee neck front was when we bought it, and the twin mounds of my brand new breasts could clearly be seen swelling against the bra! I zipped it up, and because mom demanded it, I went back to the familyroom, and there sat dad, my sister, mom, and Shelly! After we all stared at each other for a moment, I walked and posed for everyone, trying to camp it up a little.
Shelly held up a plastic bag that had uniforms like the ones she wore in it. Four of them, all in my size.
"I cleared it with my boss, Janet. I told him you were filling in for me, but I didn't tell him you're a guy. You look so good that he wouldn't have believed me anyway. He gave me these for you to wear. Here's my schedule. Girl, you look hot! See you tomorrow in school."
I took the bag and watched her leave, that sinking feeling in my gut again. Mom told me that I might as well stay dressed for the rest of the day, so I did, and that night she set out what I would wear to school the next day. A skirt and blouse with pantyhose, ankle socks and flats. I was told to be up early so she could help me do my hair and makeup. She also tossed me a nightgown, a nylon one. I had a hard night filled with dreams of taunts, but also having some of the guys hitting on me!
Mom helped me get ready, which didn't take as long this time, since I knew what I had to do, but the skirt was a lot shorter than I realized, and once again I had a lot of leg showing. Mom gave me the same purse, this time it was filled with my wallet, a lipstick, a small bottle of perfume, and some tissue. She also reminded me not to forget it. I drove to school with more than a little apprehension, but I was on my way, and there was no return. Especially after I set one foot in the school. After that it would be what it would be. As I walked in I was a bit surprised that nobody stared at me, and I went to my first class. Nobody even bothered to look at me, until I sat down in my regular chair, which set off a few gasps. Just then the teacher came in and took roll call. When she got to my name, I expected to hear my male name, but she didn't miss a beat when she asked for Janet. "Here" I said, and she went on as if it was the most normal thing in the world, but it wasn't! The fact that she knew what name I was using told me that someone, probably my mother, had called and told her in advance of my appearance.
I got a lot of looks, but nobody said a word, because they wouldn't dare, not in class. On the way to my next class however, it was an entirely different thing. My best friend, Greg, stood there looking at me like I was an alien.
"Holy Cow! You look just like a…I mean you're beauti…what I mean to say is, you don't look like I thought you would!"
"You should try it from my side of this, Greg!"
"No thanks! Let me walk with you to your next class."
I thought he might take my hand for a minute, and so did he, but we both pulled away. It was like that all day. Gaping stares from the guys, but the girls weren't giggling at me either. The boys always had their eyes wide open when they saw me, but only Greg talked to me. By the time lunch came around I was used to it, and simply sat at a table by myself. I was quickly joined by Shelly and my sister.
"This isn't working out the way we planned, Janet. You simply look too damned good!"
"Does this mean you want me to stop?"
"No, but we never expected you to look so good, either. What I'm saying is, you're very pretty, and I'm glad that you decided to do this. Not many boys would do it."
There wasn't anything for me to say to that. Nobody but mom had told me I was pretty, unless you count Greg, and he choked on it. It was easier somehow after that. I went home after school and changed into the uniform Shelly gave me, and drove to the restaurant. The owner, Gladys, wasn't expecting a boy in a dress, so she gave me a quick run through, assigned me some tables, and I went to work. After just a few hours my legs were killing me, and I'm glad mom made me buy these shoes, or I would have died I think. I made $20 in tips, which I stashed in my purse before I went home at 8. I undressed, took a shower, then did my homework. I had no trouble sleeping that night.
It was like that every day for the next three days. Then it happened. One of the guys, an acquaintance, asked me out! He actually asked me out to the show for Saturday! I was so shocked that I didn't answer him, but ran to my next class. Greg, who sat next to me, asked me if Stan had asked me out. When I looked at him, all he did was smile and shrug his shoulders.
"He thinks you're hot, and asked me if he should ask you. I told him you might say no."
"But why me? There are plenty of girls here, Greg! I'm not a girl and everyone knows it!"
"True, but have you looked in the mirror lately? You look more like a girl than some of the girls do! You're even starting to act like one lately, what with the hand waving and all that. For my money, I think you should go, just to piss off Shelly and your sister. Especially Carol, since she's been after Stan for a long time now."
That was true. And it would be a slap at my sister. The more I thought about it, the more I thought Greg was right. After class I found Stan and told him I would be happy to go with him. He said he would be over at seven. Now all I had to do was break the news to mom. There was no way I would tell dad, zero chance. I'll let mom tell him. Friday was hectic at the restaurant, and I didn't get home until almost midnight. In the morning I slipped on a bra, clean panties, then a tee shirt and my jeans before I went to eat breakfast. Mom was there all alone. I had my coffee and was munching on a roll when she asked me what I was going to wear that night.
"For your date. What did you plan on wearing?"
"A skirt and blouse, why? And how did you know about it?"
"Carol was very angry when she told me, Janet. Apparently the boy that asked you out is the same one she wanted to date."
"I had nothing to do with that, mom. I didn't even know about it until Stan asked me out, and even then I had to think about it before I said yes. Now I'm thinking I should call it off."
"You can do that of course, but if you do you'll spend a lot of time at home alone, and seven months is a long time Janet. You have to face it, honey. You're very pretty, and boys are going to be attracted to you regardless, and some, like Stan will ask you out. Now, if you want to be with me and dad all the time from now until the end of the year, that's fine, but I was thinking that you and I would go to the salon and get our hair done today. You need your nails attended to, and a better cut will make it easier for you to take care of. How about it? Are you Janet? Or are you just a boy in a dress?"
"I'm not a girl, mother."
"True, but that wasn't the question. Are you Janet?"
I know it was weak, but mom was right. "Yes."
"Alright, then. Go put some makeup on and we'll go."
I had never been in a salon before, so I had no idea what to expect, but my mom was her usual efficient self, and I was soon in a chair, getting my hair washed, then styled. The girl cut it short I thought, but after she stuck me under the dryer, another girl came over and did my nails, making them longer with rounded ends, then painting them a soft red color that has some metalflake in it. When the stylist was done I had a curly pageboy that accented my oval face just right, and those longer nails made my hands look slimmer, more feminine. I really liked the way I looked with that haircut, then, all of a sudden, I felt like a girl. On the way out of the salon mom told me that as long as we were out, we might as well take the time to expand my wardrobe a bit more. My first buy was a red and white corselet with matching panties, then two more dresses, a suit, and two more skirts with tops. I also bought heels in taupe and navy. I found myself enjoying the fact that mom and were shopping together, and after a week in skirts, I was aware of the hem length now. I still bought the shorter skirts or dresses, but now I knew what it means. Around three mom and I went home, and I went right past dad without a word, up to my room, and put things away. I did not hear mom telling him I had my hair and nails done, or the ensuing argument.
I was ready to go within a few hours. I had a bubble bath, which I found I liked a lot, then a shower and a close shave. I had redone my makeup, and changed into a pleated tan skirt with a brown pullover top that fit well enough that my breasts were well defined. Earrings and a watch, a thin beaded necklace, and my taupe heels. I did my lipstick in red to match my nails polish, then added a spritz of perfume. I had never worn perfume before, but it seemed like the right thing to do. I walked into the familyroom like always, and drew immediate stares from dad.
"Don't you like it? I think it makes me look a little better, and they told me it would be easier to take care of."
"You had your nails done as well. Just how long will it take to get those off?"
"Dad, this is going to last seven months! Even you agreed to that, so I had the acrylic nails put on! They don't come off!"
"You look…like a girl now, dammit!"
"That's the idea isn't it? You told me to honor my word, and I did. Then I found out that this was going to last a lot longer than I thought, so, if I have to dress this way, why can't I look nice? I don't want to spend the next seven months at home! Is that what you want me to do?"
Dad was in a corner now and he knew it. I had done nothing except honor my word, just like he told me. The problem is that I turned out looking pretty good, then I found myself not minding wearing a skirt at all. In fact, at the salon, when I saw myself for the first time, after my styling, I realized that I wouldn't mind staying this way. I just wasn't going to say it out loud. I let the facts say it for me, which is of course, why dad is so angry. There wasn't anything he could do about it. When he found out I had a date, he actually growled, but bit his tongue when mom told him I shouldn't have to stay at home the whole time. I had a few hours before Stan would be over to get me, so I simply sat on the couch to watch television. A little later the doorbell rang, and when I opened the door, I saw Jenny standing there!
"Hi. I thought I would stop by so we could talk a bit."
I grabbed her hand and walked out on the patio, shutting the door behind us.
"Some of the girls on the squad, well, they're wondering if you were going to practice with us."
"I have to work for Shelly after school every day for a month Jenny, so I don't see how I can, and I still have two weeks left on my bet with her."
"We understand, Janet, and that's why we were thinking that we'll let you slide on being a cheerleader, but you would have to continue dressing this way, just as if you were a cheerleader, which means it'll be for the same length of time. Either way, the result is the same. You'll be in dresses."
In my mind, I knew that arrangement this would work out fine. Gladys had asked me to stay on, even when Shelly returned, which meant that I would be making about $200 a week, that I could keep, so I agreed without any further thought. Jenny is one of the best looking girls in the school, which is the reason she is the head cheerleader. Smart and beautiful. That defines Jenny nicely.
"When Stan told me that he asked you out, I wasn't that surprised, were you?"
"You bet! Your brother never had any trouble getting a date before, so I wondered if it might be a setup of some kind, but I couldn't figure out what more could happen to me. He knows I'm not a girl, and that bothered me for a while, but rather than sit home all the time I decided to do it, and accepted."
"It's not a set up Janet, you're all he talks about. How pretty you are, your great legs, and he says you have a smile that won't quit. No, girl, he's in love. Can't you see that?"
"But I never…I'm not a girl! He can't be in…you must be mistaken, Jenny!"
"Oh no I'm not. I know my own brother, Janet, and believe me, he may know you're not a girl, but he has pushed it so far down into that brain of his that he can't even see it! All of us kids have seen you every day for over two weeks now, and whether you know it or not, you have started to act like a girl, walk like a girl, and believe me, you look like a girl in every way. Especially with that soft perm and those acrylic nails you have on. And if you try to tell me you don't like being dressed as a girl, I'll have to call you a liar. You wouldn't have let those things be done if you didn't like being thought of as a girl."
I hate it when somebody can see right through you, and Jenny had done just that. According to her, some, if not a lot of the other kids had figured it out as well. But so far, nobody has said a word to me about it, not even those Neolithic fools every school has. But how had this happened in such a short time? I mean, before this I was like every guy in school. I was hoping to get into some girls pants, I just never expected to be in them at the time! Now, Jenny tells me it's obvious that I like being a girl. I looked at her, trying to find a way to deny what she had told me, but the words would not rise to my lips, which she noticed. When she smiled at me, I had to swallow hard and try not to smile back. That would only confirm what she already knew.
"This should be an interesting school year, Janet. Based on the changes we've seen so far, I'll bet that within a month, darn few kids will even remember you were once a boy, including you. Just remember this about the boys. They all have one thing on their minds when it comes to girls, and it isn't friendship. That specifically includes Stan!"
"But I'm not going to do anything, Jenny! How could I? I mean, well, you know what I mean!"
"There are a lot of things that you can do for a guy without going that far, Janet. Don't be so naïve."
"Not that either, Jenny! No way!"
She dropped the subject, then asked me if I wanted to join her and a few of the other girls for a get together on Sunday at 2. I said I would try to be there, and she went home, leaving me to wonder if it was true. Had I become so much like a girl that I have begun to act like one? Would I become so much a girl that everyone would forget the real me? Would I be able to return to the male I am? Or would I simply remain as a girl? I went to my room, stood in front of the mirror, and tried to find the answer. My oval face, now framed by the waves set in by the perm, the makeup that made me look so feminine, and my figure, all combined to cast doubt in my mind. I didn't look like a boy in any way, unless I undressed. Dad still doesn't like the fact that I look this way, but he has quit harping about it at least, while mom has taken to thinking of me as her daughter. Right now my figure is all foam rubber with a bit of silicone thrown in. What, I wondered to myself, if I could make it seem that it was all me? Would that make a difference? Jenny and the squad had actually given me a break by not making me try to do those jumps and baton twirling, but I still had to wear the clothes for the same amount of time, and seven months is a very long time. Maybe she's right. By then, maybe nobody will remember that I am a boy. I looked in the mirror again, then decided that I might as well try to do my best, and if they all think I'm a girl, well, I'll decide what to do then. In the mean time, I decided to check out the Web, and see what was available to help a boy like me look like a girl.
What I found astounded me! I found several fiction sites that had a lot of stories a bout boys just like me! I downloaded a few, then in another search, I found a site that seemed to carry everything a girl like me would need, from a very special panty to breastforms that would be custom made just for me! The prices didn't seem that outlandish, but I didn't have a credit card, so that meant that I would have to use snail mail and a money order. I downloaded the instructions, folded them and put them in my purse. I made a note to stop at the art store in the morning. Then I read the stories. Some were pure trash, but a few hit me right where I live. In more than one case the main character, like me, had found himself stuck in the role of a female. Several very interesting hints made me take notice, and I highlighted them for later use, then I started to get ready for my very first date.
Dad was apoplectic when Stan arrived, but he tried to hide it and was polite. Stan led me out to hiss car, then drove us to the show. I wanted to ask him what the hell was going on, but didn't. If what Jenny had told me was true, he wouldn't be able to tell me anyway, so I let it drop. He and I saw the show, then stopped at a burger place for drinks. He was polite all evening, and didn't do anything more than hold my hand, so I wasn't ready when he took me home, and before I could get out of the car, I felt him pulling me close, then the gentle touch of his lips on mine! I broke away and ran in the house. Stan had kissed me, and I let him. I was afraid of what that meant. I went to bed with the taste of him on my lips, a shiver in my spine, and a feeling that it could have gone further if I had not run in the house.
In the morning dad merely asked me if I had a good time, while mom asked me if I had any plans, since it was my day off. I told them I was going to Jenny's at 2, but I had a few errands before that. I ate, then went to change. Mom insisted that I don't wear any slacks, so I wore a skirt and blouse with my gym shoes. Then I left for the art store. Finding the right color for my skin was a pain, but with the help of a mirror, I managed, then wrote down the numbers. I had decided not to tell anyone what I was going to do until I saw just how well the items looked. I arrived at Jenny's about fifteen minutes early, but she let me in, and we went to her bedroom. About ten minutes later two other girls showed up. Rachel is a tall dark haired girl with a wickedly wonderful smile and a very healthy body. Jill is about average in looks and build, but her dad has a lot of money so she always tends to be on the best teams or in the best clubs.
"I told Janet what we decided, and she has agreed, which makes her a de facto member of the squad, and I want to let her join us when we have our special outings. Anyone disagree?"
"Does that include the really special outings?"
"Of course, Rachel! Why shouldn't she join us?"
"I don't care, I was just asking, that's all."
"She'll have to get a uniform, Jenny."
"No, Jill, she doesn't. Janet doesn't practice or perform with us, we're just making her part of the squad, like a…an associate member."
They all looked at me, but I didn't have any idea what they were talking about. Jenny explained it to me.
"Once in a while we all get together, like a pajama party, or a girls night out. Once we managed to get into that strip club downtown. You interested?"
If they were asking me to join them, that meant that I had been accepted as a girl! I nodded my head, and they all hugged me. Then we all went to the mall for some therapeutic shopping. By the time I got home I never felt as feminine as I did right then. Just the way the girls treated me, like I was one of them, had made me realize that I didn't mind being a girl at all. I will admit that the thought of seeing 12 semi naked girls at a pajama party crossed my mind, but I knew in my heart that before I would ever do that, I would have those items, and it wouldn't make any difference. I would be one of them, a girl. In my room I filled out the form, and after using a measuring tape, wrote down the before measurements, and the hoped for after sizes.
In school it was like any other day, except that I didn't feel like a pervert, and none of the kids were staring at me now. My friend Greg however was staying away, and I didn't know why, because with his big mouth, it could have easily been him that made the bet instead of me. The teachers all used the name--Janet--when they referred to me now, and I had been exempted from gym classes for the obvious reasons. The coach even told me that if he let me use the locker room most of the guys wouldn't be able to do pushups without hurting themselves! I had to giggle at that. The class they put me in instead was sewing! It was the only opening they had, and I was forced to take it for the credit. Mom thought it was funny while dad thought it was stupid. After three classes however, I saw that I could buy clothes that maybe fit well enough, needed to be shorter of taken in a bit, and I could do it!
My time filling in for Shelly was over on Friday night, and I wasn't scheduled to start working for myself until Monday, so after school I withdrew the money I needed, and sent in my order for the special items. According to the web site it would take about ten days. That night I tried on one of my own uniforms, had mom help me, and made the hem shorter and took it in at the waist. Dad watched me sewing for a bit, then stomped off. I was not his idea of a son any longer, but there wasn't one darned thing I could do about it, and he knew it. That's what got him. Mom told me to ignore him, then, after he had left the room, she sat down and asked me how I felt about dressing as a girl. What should I tell her?
"You like it, Janet. That much is obvious. Now the question is how much?"
I decided to tell her exactly how much, and told her to wait while I went to get something. I went to my room and took the full color pictures I had printed out of my dresser, and the three stories with the highlighted portions, then returned to her sewing room. Without a word I showed them to her, let her read the text, and simply waited. Her eyes went first wide, then narrow, and wide again as she looked up at me.
"And this means?"
"I ordered this, this, and this mom. They should be here sometime next week. But if the panty doesn't fit I can send it back, and maybe you can do this for me."
I pointed to the highlighted text and she read it.
"I see. Well, alright, that answers the question of do you like it, but this says that you can have some sort of sex with this panty! I don't want you to find out if it works Janet, understand?"
"Yes, ma'am. But if that's the case, why not do the other for me?"
"No, I'll let you wear this panty, but no fooling around, and I mean it!"
Neither mom nor I told dad about the items. I went to school on Monday as usual, then went to work. Shelly was a bit surprised to see me there, and asked me about it. I told her what Jenny had said about my status as a cheerleader, and that Gladys had asked me to stay on. She also commented on my uniform fitting so well. I simply told her I altered them myself for a better fit, and she dropped it. She and I talked a bit, but it was clear that her bet wasn't turning out like she thought it would. I had turned out looking okay, done her job well enough to get one of my own, I could sew and she couldn't, and Stan had asked me out. Altogether, she knew I had come out on top.
On Thursday I went home right after school to see if the items had arrived. They had, so mom and I went to my room so I could put them on. It took both of us almost an hour to get me into them, but it was worth it. I now had two very pert breasts on my chest that looked as if I grew them myself, and the panty, which had a built in vagina and padding to make my hips in proportion. From any angle I was now a female, from the top of my head to the ground! When I got dressed all of my lingerie fit better, and for the first time I felt the weight of a breast as it pulled on my chest. The bra gave me a modest but definite cleavage, and I felt complete for some reason. Mom watched me as I got dressed, and saw the way the bra fit now. With the low, well padded cups, my boobs were almost straight out! Mom said that I would need new bras now, and for me to get dressed. Then she and I went shopping. I bought four new bras, only one of them had any padding in it, but with a normal bra, I had an impressive bustline now. My measurements were 36-25-36, with a B cup bra. I loved it while mom merely gave me a smile. I also bought a nightgown that was short, semi sheer, and had a robe. I had plans to shock dad that night.
After dinner, mom winked at me, so I went to my room and changed into the nightgown. It's black, so I wore the black thong panties that came with it. Tonight was the night I let dad know just how much I liked being a girl. Looking in the mirror I could just see the twin mounds of my breasts as they strained against the thin material, and smiled to myself. I slipped into the padded slippers and left the room. I walked right past mom and into the familyroom, past dad, who looked up, and almost made it to the couch.
I turned to face him directly, and he could see for himself how I looked.
"What have you done to yourself! You…you…"
"I look like a girl now, dad. It'll be easier on me, so I might as well, don't you think so?"
Tweaking him like that was dangerous, but he was so busy looking at my breasts that he wasn't thinking straight.
"Fasten that robe up and sit down! You may have to dress as a girl, but why do you have to have those! You're even starting to talk like a girl now! I give up!"
Dad left the room and went into his office, leaving mom and I alone. I went to bed satisfied that I had made my point.
School and work kept me busy, but Stan asked me out again, and I went with him. This time he parked on a shady street, and when he kissed me, I didn't pull away. It got hot and heavy, but nothing happened, and I knew that I would not return to my manhood when I went to bed that night. My days as a girl blossomed as Jenny and the squad kept their word, and I was included in many of the special outings, including a pajama party. I know what they thought, so I took the black babydoll. When we all changed, I felt seven pair of eyes on me, and turned to face them, naked of course. Without a word I slipped on the babydoll, leaving them to wonder how I did it.
Gladys went on vacation, and I was left in charge, so, as hostess, I was able to wear normal clothes, set the schedules and so on. Shelly and I had become good friends by then, and I made sure she got the times she wanted. Dad has finally accepted the obvious, but I had to help him one more time. The panty comes with a small packet that lets me simulate a menstrual period, so I used one without wearing a pad. Dad really freaked out when he saw the blood, but I cleaned up and returned wearing a pad. He never said another word about it after that. Graduation is two months away, but my time from the bet is over next week. I don't plan on changing back, but then again, I don't think anyone will care.
Stan is taking me to the Prom of course, and I intend to see if the panty will work as advertised. From a wart of a boy to a woman, that bet was the best thing that ever happened to me, and being a waitress? Well, I meet the nicest people that way.
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