Mary Mary Quite Contrary            by Janet L. Stickney       JanetLynn17@Hotmail.com

 

Mary Hanover was not a woman to mess with, or so she thought. As the highest rated student in school, head Cheerleader, and a true to life Goddess, she had it all, and a rich father that spoiled her just made it worse. She was spoiled to her core and we all knew it, but there wasn't much we could do about it. Until I came up with an idea. My name is Jason Grant, I'm a junior in high school, 16 years old, I'm 5' 7" tall, weigh about 140, I have brown hair and green eyes. I live with my mother, just the two of us now that my sister got married and moved away. My idea? Get a girl to challenge Mary in everything, including grades and cheerleading. The problem was that there weren't any girls that could even come close to her. I was the highest rated male student in the school, short and skinny, and poor. I was her direct opposite in every way. Since Mary often talked down to even the teachers, most of them wanted to take her down a notch or two but didn't have a way either.

I was talking about this with Kelly, Janet, Mike, and Steve when Mrs. Brown must have overheard us. I saw her walk away smiling, but she said nothing to us and I forgot about it. We were close to the summer break when Mrs. Brown called the five of us that were talking into an office. "Close the door please Jason." When we were all seated she got right to the point. "I know that you all want to take Mary down a peg, but she earned all of her grades and had to try out for the squad like everyone else. But if you were to continue to try and find a way, knowing we don't have any girls that can take her down, then that leaves only the boys. If you picked someone who was smart as she was, and willing to try out for the squad, and could talk him into dressing as a girl, I'm confident that he could be enrolled as a girl for the Senior year. But he would have to be as smart as she is." I watched as they all looked at me!

"Not me!…why me!…NO!" Janet looked at Kelly and then back at me.

"Yes! Of course! Jason is the only one that could upset her from her throne! And besides that, only Seniors are able to be Queen of the Prom! It's perfect!" "Janet… no!" "Yes! Jason, we have all summer to change you into a girl! Kelly and I will help you…" She turned to Mike and Steve, and added, "if you guys say one word about this…" "Not a chance of that Janet, Mary ruined all of my books once and I had to pay for them myself. Steve nodded his head in agreement. "Okay then! Jason, you're it!" I'm still not sure how it happened, but I was elected to become a girl, and one that would topple Mary! I gave a half hearted "No" one more time, but it was done as far as they were concerned!

I somehow forgot to tell my mother about all of this, and on the last day of school I went home just like always, walking with Janet the four blocks home. "I'll be over in a few hours Jason." "Okay Janet, see you then." I walked in the house and saw my mother with Mrs. Brown and Mrs. Roth, two of my teachers! "Jason, they tell me that you are going to become a girl for the summer and all of the next year. Why didn't you tell me this?" "I was afraid mom, and I was hoping it would just go away." "Your father worked for Mr. Hanover for years, and when your father was killed on the job he didn't even send a card! If you can take his daughter down a peg I want you to do it!" It was more anger out of my mother than I had ever heard before! "The teachers took up a collection Jason. We know that you'll have to buy some things." She handed me an envelope filled with cash! It's $3000 and should be enough to get you enough clothes to manage." They stood up, shook mom's hand, and then left!

"Heather left a lot of her things behind Jason, maybe we can find some things you can use." "Mom!" Just then the doorbell rang and Kelly and Janet walked in, both of them carrying a small bag. "Ready to begin Jason?" With everyone pushing me, I was done for, so I reluctantly nodded my head yes and the four of us went to my room. Janet began laying things on the bed. This is a complete outfit from the skin out and should fit you." Then Kelly started to pour our makeup and shoes, and a bag of rollers and a curling iron. "I think I can handle it from here girls; why don't you come back in two hours?" Janet and Kelly said okay and left me alone in my room with my mother. "I know that this seems a little strange Jason but it would be a very good way to get back at the Hanover family. His daughter has been a spoiled brat her entire life and he's a tyrant. The only one in the family with and grace at all is his wife and she's scared of him." Mom sat on the bed and looked at me with a gleam in her eye that I had rarely seen. "I'll tell you that if you insist, I will not make you do this. It will be hard for you to be something you're not and I know you think it cannot be done, but I think you can do it, and more, I think you'll begin to like it. For today however, I want you to let us make you over into a girl. If it's a disaster we'll stop and go no further. The final decision will be yours, but make it after we make you up."

Those twinkling blue eyes of hers got to me, and I agreed to let her make me into a girl that one time, just to see how I looked. As soon as I said okay she told me to strip and began by smearing a cream all over me, as far as my briefs. At her direction I went in the bath and did the rest, waited for a time and stepped into the shower. I didn't have a lot of hair anyway, but what I did have washed down the drain in a swirl leaving my skin smooth and hairless. I washed my hair and shaved before I put on a robe and went back into my bedroom. With no preamble at all, mom gave me a pair of panties to put on. Once I was covered she used a measuring tape on me, just noting it on a pad before she gave me a bra to wear. I slipped it on and she adjusted the straps, filling the cups with socks. "These are pantyhose, let me show you how to put them on." As the slick nylon slid up my legs I felt an electric charge as they whispered up to my waist. A slip was held out and I stepped into it and a short dress was slipped over my head and zipped up. The shoes were my sisters, a pair of red heels only two inches high. My feet slid into them and to my surprise they fit! "Let's go into my room and I'll do your hair and makeup." I knew how mom did hair, my sister complained about it all of the time, so I asked her if Janet could do it instead. "After all mom, she's my age, and has a better handle on the current styles." With a nod of her head I called Janet and within minutes she was at my house.

She took one look at me, smiled, and went right to work. Within a half an hour I had pink hair, from the rollers, and she started in on my face. "I'll show you how and after this you'll have to do it yourself, okay?" "Okay Janet, if there is a next time." All she did was snort in disbelief and begin by covering my face with foundation. "You have that same clear, pale skin your mother and sister have Jason, this will be easy!" After the foundation came the powder, which she let set and then brushed away the excess. On my eyes she used earth tones and a brown eyeliner on the upper lids, and a brown pencil on the lower. As I watched her in the mirror I was astounded that she was able to make what I thought was a typical male face and make it into a very feminine face! On my cheeks she used a soft peach blusher, which she drew out with a sponge. "I'll do your hair now Jason." A towel went around my neck and she took out the rollers, leaving my hair a mass of small curls. As she brushed my hair out she used scissors to trim here and there, and when she was finished I had a curly cascade of curls down the back with a higher, fuller top and bangs that swept to one side. Mom gave her two barrettes which she put in, holding my hair back on the sides exposing my ears. Red and gold button earrings were put in place of the studs I usually wore and then she handed me a soft red lipstick. I traced my lips and looked in the mirror in shock.

"Stand over here Jason." Mom pulled me to the full length mirror and I saw her for the first time. She was beautiful! She had long legs perched in red heels that accented the short hem of the dress, a modest bust with a face like an angel! "I told you that you would be beautiful Jason!" I simply could not take my eyes away from the mirror to respond! "This is going to be so easy Jason! Your biggest problem is going to be how to keep the guys away from you!" "Right! Like I'm going to date or something!" Janet changed tactics and asked me about a name for our new creation. "I never gave it any thought Janet, I don't know!" "If you had been born a girl we were going to name you Megan. How about that?" "We already have three Megan's in school now Mrs. Grant, how about… Carolyn?" "Carol" I said, not willing to lose what little control I did have over what was happening to me. "Okay, Carol…Michelle" my mother said, and it was over. I now had a name. Carol Michelle Grant.

"Let's go over to my house Carol, I'll call Kelly and the three of us can do something!" "But your mother knows me!" "As Jason sure, but I already told her what we are doing and she agrees. Hanover passed over my dad for a promotion and made his son the Production manager. Believe me, there is no love lost in our house for Mary Hanover." I looked at mom and she told me to go ahead and go with Janet, "because sooner or later you'll have to leave the house and now is as good a time as any." But… But I…" "I'll get you a purse Carol." My mother found the red purse and put my wallet in it along with the lipstick and gave me a peck on the cheek. "Be back by dinner time or call me, okay?" "I will mom."

Walking out of the house was the hardest thing I have ever done! Being dressed in my own room was one thing, being outside was another altogether, but with Janet holding my hand, I stepped outside. As we walked I felt the skirt swaying back and forth, the swish of the nylons as my legs rubbed together, and the taste of the lipstick. "See, nobody is looking at you in any way funny Carol. You're doing fine! Relax and enjoy it!" We made it to her house without incident, but when she introduced me to her mother, who had known me since birth, all she did was give me a hug! "You're very pretty Carol, Janet might have to be careful!" "Mom!" "Well she is very pretty!" I was embarrassed and Janet quickly took me to her bedroom.

I walked into a room that was all pink and white, with dolls everywhere and smelled of perfume and makeup. "Mary is smart Carol, and she'll find out where you live within a day or so. We have to say that Jason went to live with his Aunt and you came to live at Jason's house. That explains your being new, why you look like your mother and sister, and why she can't find out anything else about you." It sounded realistic and I agreed. "But I haven't decided to do this yet Janet." "Right. The way you look will make her eat crow and you know it!" I wasn't so sure. "Your mom says that you wear a size eight and I have a lot of clothes that are that size that I can't get into anymore. Want to try them on?" In for a penny they say, so I nodded my head yes.

Kelly came over about two hours later. I had on a mini skirt and a see through top, spike heels and wicked makeup when she stepped into the room. "Goddamn! You look terrific!" "Kelly, this is Carol Grant." "I knew that you could look good, but I never figured on this!" Still unsure of the impact I was having on them, and not sure if they were just being kind, I had no response. Janet filled her in on the 'legend' she had created for me, and then Kelly picked up the phone and called Mike! I heard only her side of the conversation, but it was enough to make me nervous. "Mike, she's gorgeous! Call Steve and meet us at the Burger Bin in half an hour….yes, she'll be there. Her name is Carol. Bye!" "You better change into something a little less… sexy Carol. Wear what you wore over here." Janet helped me get undressed and I quickly had the red dress on again, washed my face, and with Kelly and Janet watching, did my own makeup for the first time. When they said it was fine I was propelled out the door and soon found myself in front of the local hangout, the Burger Bin. Kelly opened the door and we went in together and sat at a table by the window.

Ten minutes later Mike and Steve walked in with Peter, Kelly's boyfriend. When they sat in the booth I found myself sitting next to Mike, Janet next to Steve. Both Steve and Mike knew who I really was they're reaction was worth it. Pete didn't know, and when I was introduced to him as Carol he actually hit on me, drawing an elbow from Kelly. "You look fantastic Carol!" "Thank you. I try." "The first summer dance of the year is tomorrow, why don't we all go?" Peter, since he did not know about me, had assumed that three boys…. three girls, why not? Before I could answer Janet said okay, and then she added, "Mike, can you pick Carol up at her house? We'll all meet at the dance." "Okay Janet. Okay Carol?" What could I say? "Of course Mike, I'd like that." I had to be polite just to protect myself didn't I? "Great! We better be going if we want to be ready on time. Dressy?" "Of course my dear, I'll wear a suit if you like!" Peter set the tone and after we left Janet told me that she had the perfect dress for me to borrow, "with all of the right undergarments of course. You can take them home and get ready, your mother can help you get dressed." It was a done deal, and I was crawling further out on the limb.

When I left Janet's house I had a bag over my arm, my purse, and a small bag of other things. When I told mom what had happened she was excited! "This is a good way for the other kids to meet you Carol! Show me what you brought home." In my room I showed her the dress, and she was unimpressed. "I think Heather still has that black dress here, let's look." I knew which one she meant, and if it was still in the closet, and I wore it, I would certainly make a splash at this dance! Mom found it, and I started to take it to my room when mom told me that I might want to move into Heather's old room. "It does have the vanity, a private bath and a lot of clothes you will be wearing, and it is decorated for a girl." I nodded my head yes and drove even deeper into becoming a girl, which after this dance, would be a foregone conclusion and I knew it. Now was the time to say no, yet I couldn't! During the day I felt the clothes, tasted the makeup, and saw the way people treated me, and I liked it! All at once I knew that I would be Carol for the coming school year, and like it at the same time. Why I could not figure out. I had never dressed as a girl before, yet now I liked it! After mom unzipped me I stripped and looked in the mirror. As a male I was unimpressive, but as Carol I had a beauty that drew me into her clutches, and decided right then to be as feminine as possible that night.

My skin was still smooth, so I washed off the makeup and shaved again and looked in the bag Janet had sent over. The waist nipper was big on me and I asked mom to help me. She came up with something a lot worse, a corselet! I didn't know it at the time, but when she wrapped it around me and tightened the laces I felt as if I was being cut in two! "Raise your arms dear, and take a deep breath." I did and when she pulled my waist shrunk to a svelte 20 inches, down from my normal 25! When I lowered my arms all of my now compressed flesh fell into the bra cups creating a bustline! I pulled the skin up and filled the cups even more, and mom gave me two small foam pads. "Put them under your breasts Carol, they will fill out the cups and lift you a bit more." She was right, and all of a sudden I had an hourglass figure, and boobs! "Heather used this all of the time because she was so flat chested for so long; now you can use it." Her giggle did not humor me, as I could hardly breathe. "You'll get used to it, we all do. In a few days you'll feel naked without it." Mom left and I sat at the vanity to do my makeup, alone, for the first time.

With careful attention to detail I created a softly feminine look that was perfect for me. Not overtly sexy nor to young, but that of a girl on the cusp of becoming a woman. With my green eyes I used the earth tone eyeshadow with a softer gray over that, deep black eyeliner and a black pencil to outline my eyes, making them wider. Black mascara just a bit though, to add fullness. On my cheeks I used a silk rose blusher that gave me higher cheekbones and a wider smile. My hair was still just like it had been done that morning and I saw no reason to change it. I pulled on the pantyhose and snugged them to my waist and took the dress out of the closet. The shapeless black satin dress was in my arms when mother came back into the room, and she helped me get it over my head. As she pulled it down and zipped it up I felt the material close around me in a delightful way. The twin shoulder straps held up the square cut neckline exposing a modest amount of my breasts, tapering down the bodice tightly, then flaring out at the hips. The crinoline petticoats held the skirt out a bit and crinkled with every move I made. I stepped into the black heels and looked in the mirror. The hem was a good two inches above my knees, my waist tiny with a nicely full bust. My skin, like my mothers was porcelain clear, my makeup accenting the natural beauty I never knew I had. Mom went into her room, returning with black and gold chandelier earrings with a matching choker style necklace. It slipped the earrings on as she fastened the thin gold chain around my neck, leaving the small pendant between my breasts. On my left wrist I wore her gold watch, on the right, a small bracelet. "Any more jewelry than that you would look like a tart Carol. Use this." In her hand was her bottle of Obsession perfume. I dabbed some on my elbows, wrists, and in the crook of my neck, and stood in front of the vanity and put on my lipstick.

When Mike arrived mom answered the door and called for me. I walked down the stairs just like she had me do twice before, with a saucy feminine step that made the skirt sway. His eyes never once left me as I walked over to him. "Hello Mike." "God Carol, you're gorgeous!" "Thank you." "You have her home by one Michael!" "I will Mrs. Grant." Then he surprised me by taking my hand as we walked to his car. On the way over he kept looking at me, which was hard not to notice. "What!?" I was just thinking how lucky I am to have the prettiest girl there with me!" "But…" "You're my date right?" "Yes," "and you know I don't date boys?" "yes," "well I'm not. I'm taking a beautiful girl to a dance, so relax and enjoy it." When we pulled up I stayed seated until he opened the door for me and we walked in together.

Mike introduced me all around, to kids I had known for years and not one of them knew who I was. To them I was the foxy chick with Mike and that's all. Mary saw us of course and made an effort to meet me but Mike always managed to head her off by asking me to dance or something. Janet and Kelly had expected me to be wearing something else and they were shocked when they saw that I now had boobs, just like them, but did not take me too far from Mike. On the way home we stopped for a snack and later, in front of my house, when he opened the door for me I stepped out, right into his arms! We looked at each other for what seemed forever, then his lips touched mine, not once, but twice! "Carol, you are just what I said you were. The prettiest girl in the school, can I call you tomorrow?" "Sure." Over run with emotions exploding inside I ran into the house and slammed the door. "Have a nice time dear?" "He kissed me mother! On the lips!" "And why not? you're a very pretty girl!" I ran to my room and undressed, trying to figure out why I liked Mike kissing me!

In the morning, after breakfast I went to my room and slipped on some shorts and my gym shoes and looked in the mirror. Carol was still there in the traces of unwashed makeup and a slightly messed up hairdo, and I sat at the vanity and brushed my hair out, putting it into a ponytail and redid my makeup, just like the night before. I wore a bra with socks in the cups again, slipped on a Tee shirt and went to rejoin mother. Together we cleaned the house until Janet came over at 11. "Girl, you were a smash in the dress!, and look at you! Sexy even in a tee shirt and shorts!" Just then Mike called and wanted to come over, which Janet picked up on right away. "I'll call later Carol, bye!"

Mike came over an hour later and we went out on the patio. "All my life I thought I liked girls Carol, and then you came along!" "Mike, didn't you tell me I am a girl?" Before he could answer I added, "well, I am a girl now. I found out that I like being a girl and IÉ liked it when you kissed me." "Good." He leaned over and kissed me again, but this time my arms went around his neck and held him as his tongue probed my mouth. Gasping I let go, afraid to continue. "Now that we have that settled, would you wear this?" He handed me his class ring! "But Mike!" No buts Carol. Wear it for me." He slipped it on my finger and smiled at me. "I know what Janet and Kelly will say, but I don't care Carol. You turn me on every time I see you, and I want you to be my girl." I was flabbergasted that he felt this way, but I kept his ring tightly in my hand. I said one word, "yes", and he kissed me again, just as mom walked out on the patio. She said nothing and put the tray on the table and left us alone again.

Over the week Mike and I saw each other every day, except on Thursday when I stayed home to try on some things I bought from the Internet. I showed mom and agreed to let me use her credit card. When they arrived I went to my room and after carefully reading the instruction sheet, put everything on. When mom saw me for the first time I thought she was going to faint. I had perfectly crafted breastforms that attached to my chest with a special glue and were undetectable even up close, and the vaginal panty hid my small manhood easily while at the same time padded my hips out. I would now have to sit for all bodily functions, and I could, if it happened, have sex with a male! When I got dressed this time I was a lot more confident now, and asked mom if it wasn't time we expanded my wardrobe.

I wore shorts and a top shopping because mom said that I would have to try on a lot of things, and she was right. We bought four bras in 34 'A', slips, skirts, blouses, a dozen panties, slacks in three colors, two suits, five pairs of shoes, all sorts of earrings, bracelets, a watch, necklaces, sweaters, two 'good' dresses, and lastly, a bikini. I tried it on and mom had a heart attack when I stepped out of the booth, but I liked it and added it to the pile. After we took it all to the car mom drove me to a salon and I had my hair and nails done for the first time. Mom told the girl what she wanted her to do, and I sat back and let her do it. Three hours later I left the salon with richly auburn hair, my eyebrows tweezed into a high feminine arch, my nails now longer and painted a soft pink. From there we went to a store that specialized in makeup and when I had my makeup done by a pro, we bought plenty of everything she used.

Janet came over later that afternoon, took one look at me in my bikini and flopped on the floor! "Carol! You got tits!" "And more Janet. See how the bikini fits?" The cleft of my sex was clearly defined, and she saw it; then I slipped the bottoms off and walked to my dresser and slipped on some panties. "I would say that we are now equal, wouldn't you?" She didn't say a thing as I took off the top and put on one of the new bras, the lacy low cut one and pulled a blouse on. Then she saw the ring on a chain around my neck. "That's Mike's!" "I confess, he fell to my charms and he is mine. "Carol, not only do you look stunning with your hair that way and that magnificent body, but you have Mike too!" I stepped into a denim skirt and sat on the floor next to her. "I'm going to stay living as Carol, even after we graduate Janet." "If I looked like you do I would too!

Mary Hanover tried everything to get to me. She hit on Mike, asked questions about me all over and generally became frustrated, and it got better. When we started school in the fall I tried out for the Cheerleaders and won a place, then I was elected the lead Cheerleader by the other girls. Later, when our grades were released, I scored higher than she did, and she almost had a fit, right in the school. Mike and I became well known as a couple and she quit trying to get to him. By Christmas I was as much a female as I could be, and began taking hormones. In the spring I was named the Class Valedictorian for graduation, and shortly after that came the Senior Prom. I now longer need the breastforms, and the night of the Prom was memorable for Mike and I. I suggested that he might want to get a room, and after the dance he and I made love many times. My special panty was worth every cent, but my lips made him quiver in delight and I tasted him as often as I could. At the Prom I was named the Queen of the school, which made me chuckle inside because they were exactly right.

And Mary? Well she turned bitter and no amount of money her father spent could make it better. She had it all and let it slip away to a crossdresser because she was so snobbish. I hear she's in Switzerland now, at a finishing school. I hope she learns something about people there, she didn't learn it here.

(the end)

 

 

 

© 1998
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.

At the request of the author, this story is presented in 12 point, Times New Roman.