Crystal's StorySite

My Sister's Crazy Idea                                by: Janet Stickney   


My sister had come up with some really crazy ideas over the years, but when she told me about this one, my first reaction was to tell her that her hobbyhorse had broken a rail. But like so many times before, I sat and listened to her, waiting until she was done before I told her what I thought. But she persisted, explaining in greater detail, and against my better judgement, I agreed that she had a point, but wanted to know why me?

My name is Tim Grant, I'm 18 years old, 5'7" tall with brown hair and blue eyes, I weigh about 140. My sister Gretchen is 19, 5'7" tall with brown hair and blue eyes, weighing in at 125 pounds. We lived with our parents in a suburban home much like any other, our dad worked as a plumber and mom was a registered nurse. Gretchen had been mauled by one of her dates and wanted to get even, or more politely, more than even. She wanted the guy destroyed if possible. She had escaped being raped because someone had heard her screams and saved her. When dad found out he was all hell bent on a more direct approach to justice, but mom had said no, "We can find a better way". I think it was mom and Gretchen that came up with the idea together, but Gretchen always said it was her idea. The idea? They wanted me to dress as a girl, get close to this fellow, and ruin his day in a most public way. The problem is, I would be destroying myself as well. All four of us were at the kitchen table talking about it, and when I mentioned my dilemma, dad, who was not real keen about my dressing as a girl anyway, asked why it had to be in a public place.

Mom said, "Why not in a private place, but put it on film? That way Tim wouldn't have to be exposed, and as a motivating factor the film would serve nicely."

When he thought about it for a moment, he added, "I still don't like having Tim dress as a girl, so I'll say no until I am convinced he can do it easily and get away with it without being found out."

That was all my mother and sister needed to hear.

I was unsure about doing this, even though I had dressed as a girl several times over the years at Halloween. But this time I wasn't a little boy, I was an adult, and if I failed I would be the one to suffer the failure, nobody else. But when mom and Gretchen looked at me, I did what I always did when mom wanted me to do something, I nodded my head yes.

"Good! We'll start right now. Go to your room Tim, and I'll be up in a minute."

Mom made it clear that Gretchen and dad were not invited to help in any way, and in fact asked them to leave the house.

"Come back at 5 and the four of us will go out to dinner."

As soon as dad and Gretchen left mom came to my room with an armload of things. Under her direction I was introduced to cream hair removal, eyebrow tweezing, and having my hair in rollers. After I had showered off the cream and shaved as close as possible, mom did the rest. My eyebrows were thinner and had a higher arch, my hair was set in rollers with some kind of gel. I was starting to look like Gretchen!

Using my sister's clothes, mom helped me get dressed, or at least she tried to. I asked her to leave the room.

"I can handle it from here mom."

Once she had left the room I pulled the panties on, then the pantyhose. Mom had also put out a padded pantybrief that Gretchen had used when she was younger. When I had that on it gave me hips and a rounder shape. Then I found the waist nipper, and after I wrapped it around myself my waist shrank to a nice 25 inches. The bra was 36B, with what I now know had a demicup. I used some socks to pad it out, and pulled the dress over my head without zipping it up, and called to my mother. She returned, zipped up the dress, and had me come into Gretchen's room. I sat at the vanity as mom put a towel around my neck and I got my first lesson in makeup. Foundation, then a loose powder, which I brushed off after it had dried. Eyeshadow, green and plum, black eyeliner and pencil to outline my eyes, and just a bit of black mascara. Then mom took out the rollers and styled my hair. When she was done I was stunned at how I looked. I was handed a lipstick, which I traced on my lips, the hot pink making my face seem to come alive.

"Now all you need is some jewelry."

I had long ago pierced my ears in an effort to fit in at school, so when mom gave me the gold hoop earrings, I merely slipped them into my earlobes. A gold necklace and a thin bracelet along with two rings she gave me completed the jewelry.

"Now some perfume."

She handed me the small bottle. I dabbed some on my wrists, elbows, and neck as directed, and stepped into a pair of mom's shoes. They were black to match the dress. I stood in front of the mirror and looked at the girl standing there, and she did not look at all like Tim! It was like I was my own sister in a way. I looked more like mom, but definitely a girl rather than a boy in a dress.

"Now all you need is a name. Have you picked one out yet?"

"A name? No, of course not!"

"Well you'll need one now… how about… Kelly?"

I did not want the name Kelly, it was the name of a girl that had dumped me. That's when I suggested Janet. Mom loved it, and added a middle name, Lynn.

It seemed to me that some of the more feminine movements came naturally to me, like walking in heels. I was forced to take shorter steps, which made my butt sway more, and to keep my balance it was easier to hold my arms bent at the elbows. Mom gave me some tips on how to sit, what to do with my hands, and so on. The dress was short on me, the hem was mid thigh, and my nylon clad legs were quite shapely if I do say so myself. It was seeing so much leg showing that threw me a little. The dress was a sheath that had the skirt portion flaring at the waist, a round neckline, and was sleeveless, and it fit me pretty good. Mom was ecstatic at how I looked, which bothered me just a little. I was her son, but she was acting as if I was her daughter! I was sitting in the familyroom when dad and Gretchen came home, and their reactions were worth it. Gretchen squealed and smiled a lot while dad just harrumphed a few times before he finally nodded his okay.

Dinner was uneventful, just a couple with their two daughters having dinner. I was surprised that I passed as a female so easily, especially since I was so acutely aware of my circumstance. By the time the dessert was served dad wanted to know what the plan was exactly, as I did.

"Well, I thought that we could set things up so that Janet would meet Mike at a party or something. Knowing how he likes to conquer, he'll go after Janet and then we'll get the film we want."

"There's a lot of holes in that plan, and Janet would be at serious risk the entire time. It seems to me that you should take the time to introduce Janet around and gather some friends before you spring this plan of yours. See just how she is accepted by some of your friends."

Dad was already starting to use the feminine pronouns when he was talking about me, which was okay I guess. Based on how I looked, it seemed almost natural. Meeting Gretchen's friends would definitely be scary because most of them knew me, but when I mentioned it both mom and Gretchen just smiled and told me not to worry about it!

That night Gretchen and I went to her room and talked about what she wanted me to do. I told her that no matter how nice they thought I looked, making Mike come on to me would mean that I would have to let him touch me, even kiss me. I wasn't prepared for that, and wondered how we would get around that.

"Play it by ear Janet, and don't do anything you can't handle. This is going to take a while anyway, maybe a month or more, and by then you'll be so used to being a girl that it might seem different by then."

A month! Or more? I thought this would only take a few days, but she said no.

"You have to become known, and he has to see you at least a few times. It'll be okay, really."

The next day Gretchen spent the whole morning teaching me how to do makeup, and after the fifth time she said I could do it. Hair was harder, but I managed to learn how to put my hair in a ponytail, braid it, and also brush it out into a modest pageboy. She had me put my hair in a ponytail and gave me some shorts and a top and told me to go change.

"It's time you met a few friends of mine."

I was in my room and had just taken my shirt off when mom came in.

"I went over to see your Grandfather this morning, and when I told him what you were doing for Gretchen he gave me these." She handed me two small pink and white boxes. "These were your Grandma's. He kept them after she died because he didn't know what to do with them."

I opened the boxes and saw a pair of breastforms! They were very realistic in shape and color, and when I picked one of them up I was ashamed at myself for what I was thinking. They felt like the real thing!

"I'll help you put them on Janet, but as soon as I do they'll stay on for at least ten days or so. By the way, they're a B cup and should be perfect for you."

Then she attached them to my chest using a medical adhesive. Within minutes they felt warm to the touch and I could feel the weight of them whenever I moved. I looked in the mirror and it was as if I had grown boobs overnight! As soon as mom left the room I put on clean panties, 'tucking' myself before I pulled the padded pantybrief on. When I put the shorts on I had the tapered look in front that most girls have. I put the bra on and instantly saw that I now had cleavage. I pulled the top on, put the gold earrings back on as well as the rings and watch, the ankle socks Gretchen had given me and my own tennis shoes. Then I joined Gretchen in her room.

"You look very nice Janet! Take this." Mom handed me some money. "You need to buy some panties and a few bras of your own, so you girls go to the mall and buy what you need. Gretchen will help you. Get a few skirts and dresses of your own as well, and maybe a few blouses and at least two pair of shoes."

Before I could say anything Gretchen took my hand and we left. The purse hanging on my shoulder felt strange, but walking into the mall was worse. My only consolation was that I now looked better than the day before, and with the breastforms I was a lot more confidant. We went into a department store, and then the lingerie department. I bought a dozen panties, three bras, and a new waist nipper and padded pantybrief. In the dresses, Gretchen and I picked out several dresses and I tried them all on, buying three of them. I got four blouses, three skirts, and at her suggestion, or rather her demand, I tried on a few suits, buying a tailored pink suit. I also got a swimsuit.

"You know, since you're going to be Janet for a while, maybe several months, you should have you hair styled and your nails done. We have enough money, so why not?"

I knew what that would mean of course, but I was getting over being afraid of it, and more into this being a girl, so, without a thought, I agreed.

They had an opening at the salon, and I soon found myself in a chair. The girl wanted to dye my hair blond but that was too much of a change for me and only agreed to let them add auburn highlights. Gretchen had suggested a light perm to make it easy for me to take care of and not knowing exactly what that meant I said yes. The girl cut, trimmed, tinted and put my hair in rollers and I was soon under the dryer. While I was there another girl came over and started on my nails. By the time I left the salon my hair was done in a pageboy that had curls cascading down the back and sides, framing my face, with bangs swept to one side. My nails were now longer and painted a soft red; the longer nails made my fingers look longer and thinner! When I looked in the mirror all traces of my boy self were gone!

"Let's go home Janet, put all of this stuff away and I'll make a few calls."

Dad was home when we returned, and when he saw me I thought he was going to swallow his tongue, but Gretchen and I breezed right by him and went to my room. When we went in I saw that someone had made me a small vanity, complete with mirror! I hung up the clothes and put the rest in my dresser and was about to leave when Gretchen told me to change into one of my new skirts. She went to her room and I began to undress. I changed into the new padded pantybrief, added pantyhose, and then pulled on the dark green pleated skirt and a white blouse and wore the new black flats. With my hair and makeup still okay, I went to Gretchen's room and went in without knocking. She was standing there in her bra and panties brushing her hair out. I started to leave but she insisted that I stay.

"Might as well get used to seeing other girls partially dressed Janet, after all, you're a girl now and they won't think anything of it if you're in the room."

I sat on the bed and watched as she also put on a skirt and blouse. When we walked into the familyroom together dad once again started to sputter. I pulled his chain a little by posing and asking him if he liked my new hairstyle.

"It's… nice… but you look so…"

"Feminine?" Gretchen said.

"Well, yes as a matter of fact!"

"That's the idea dad. Janet has to be perfect and you know it. You even said it yourself."

"I know, but I never thought… I mean…"

"Dad" I interrupted, "We all agreed on this, and I have to admit that I was worried a lot, but we were at the mall all morning and nobody even gave us a second glance. Besides, I kind of like it now."


"I said I'm beginning to like being dressed as a girl."

Mom walked in right then and heard me say that and told dad that was exactly I needed to feel if this was going to work. Then she looked at my hair and nails, the new skirt and the way I looked in general.

"I see you had your hair done! I like it! It fits you."

"We're going over to Pamela's house. We'll be back later, okay?"

Our parents nodded their heads yes and Gretchen and I left. This time I drove. Pamela had known me for years, yet she did not give any indication that she recognized me, and accepted me as just another female friend of my sister's. When we were alone with her in her bedroom we told her the truth. Her reaction at first was denial, then shocked acceptance. Gretchen told her why I was doing this and we asked her to keep our little secret. Of course she agreed right away.

"Jill is having a party tomorrow night, why don't I call her and ask if you two can come over. Maybe she can ask Mike to be there as well." I sat there while Pam called, nervous about what was going to happen.

Needless to say we were invited, and Gretchen and I went home to change.

"Pam said it's supposed to be dressy tonight. I guess Jill's birthday is the day after and she wanted to really go all out, and I have the perfect dress for you to wear."

I went to my room and stripped, grabbed the hair remover and covered every part I could reach, washed it off after a 30 minute wait, and shaved as close as possible. A plastic cap protected my hair while I was in the shower. When I was in my room I used a skin lotion, and then dusted my body with a flower scented powder. I had done some searching on the Internet and found a few helpful hints that I wanted to try. I cut a small triangle of pink material and made a slit in it, then using medical tape I secured my penis between my legs. Then I pulled on clean panties, the padded pantybrief and added a single foam pad right at the waistline in front. The pantyhose were next, and after that I sat at my new vanity. In the top right hand drawer I found some makeup and began. Foundation, a loose powder to soften the skin tone, and then the eyes. I used earth tones with a bit of gray, using a deep black eyeliner and mascara with a brown pencil to define my eyebrows a bit more. On my cheeks I used a soft silk rose blusher. Gretchen came in and gave me the dress, and for the first time saw the breastforms attached to my chest.

"God! I thought those were real at first Janet! Now I know that this is the perfect dress for you to wear! But let me get you something else to wear with it."

What that something else turned out to be was a corselet.

I took the pantybrief off and wrapped it around myself and fastened the hooks in the front. Once the zipper was pulled closed I tightened the laces until I could just bear it and looked in the mirror. My waist was now down to about 24 inches and my boobs had been pushed up into the cups of the built in bra and held together. Reaching in I settled them a bit and it scared me just how sexy I looked. My nipples were just barely in the cups of the bra! I went into her room and this time she was naked! She pulled on her panties and then I watched as she also wrapped a corselet around herself.

"Can't let you be the only one showing off!"

Gretchen had a nice figure, and the corselet made it even more so. Then she went to her closet and pulled out two dresses and gave me my choice. Both were sheath dresses, both low cut, both sequined. But one dress was a light green and the other one red. I took the green one, and she helped me get it over my head and zipped up. It had a low back and a single strap that went from one side, around my neck and down to the other. While she slipped her dress on I looked in the mirror and saw just how short it was. A bit higher than mid thigh, form fitting, and the material just covered my corselet, leaving a lot of breast showing. I zipped up her dress and saw that hers was just as short and revealing as mine was.

She gave me the jewelry that went with the dress and I went back to my room. Black heels and purse, the white rhinestone and green chandelier earrings and a small choker style necklace with a matching stone in the center, perfume, and lastly I removed the plastic cap and used a brush on my hair. It fell right into place because of the soft perm. I went back into Gretchen's room just as she finished dressing. Once again we went into the familyroom together. Mom was the first one to see us and stood up.

"Janet! I never imagined that you could… You look ravaging!"

Dad's mouth popped open and nothing came out, so I went to him and gave him a kiss on the cheek.

"Like it daddy?"

"You look very nice… Janet."

Mom and Gretchen both knew I was pulling his chain a little and giggled. Then we left for the party.

By now I really liked the way I looked and had begun to wonder if I had to give this up after Mike had been taken care of, but kept that to myself. We walked up to the door and Jill let us in. I was introduced to her and she showed us in. Mike was in the corner working on a girl named Stephanie. He never even looked up. Jill and Pam introduced me to a lot of people that I have known since grade school, and not one of them gave the slightest indication that they knew me. But all of the guys, 100% of them looked me over from the ground up and stopped at my boobs every time. Now I knew how the girls felt about that. It was like being raped with an eyeball. When Mike saw me he smiled but stayed with Stephanie, while Pam's brother Dave began to talk to me. When the music started he took my hand and I found myself in his arms as Rod Stewart sang. He was a lot taller than I was even in heels, and I had to look up a bit to talk to him. I did that one time to many and found his lips pressed firmly against mine! All night he stayed close to me while continued to ignore me, and when it was time to leave he asked me of he could take me home. I wanted to say yes, I mean no, but "yes, I'd like that" came out of my mouth. I told Gretchen and all she did was smile at me.

Dave wasn't forceful about it, but when he drove up in front of the house he pulled me close to him and kissed me. I didn't pull away and he kissed me several more times before I opened the door.

"Can I call you Janet?"

I gave him the number and went in the house even more confused than ever. In my room I undressed and went to bed, but I dreamed of Dave kissing me. In the morning Gretchen was kind enough not to ask, but when Dave called and dad answered the phone it was all I could do not to run to the phone. He asked me out to the show and I said yes. Dad isn't stupid by any stretch, and knew right away that I had accepted a date with someone named Dave, and he wanted to know what was going on.

"For all intents I'm a girl now dad, and Dave asked me to the show, and I can't see any reason to say no."

He merely shook his head in disbelief and I went to help Gretchen and mom clean the house.

I wore a skirt and blouse for my date with Dave. I had known him for years, but now he thought I was a girl and I wanted to keep it that way, so I was as feminine as I could be all night. When he drove me home he stopped at the park, which I knew meant that he wanted to stop and make out. I wanted to say no, but my newfound feminine self said yes, and I was quickly in his arms as his tongue probed my ears and mouth. I felt his hand on my leg, and then as it crept up to hold my breast. As soon as I felt his hand on my breast I broke away, but he held my hand on his leg, and then, in a single move, he put my hand on his manhood. I was in a trance like state by then, overcome with feelings of femininity and strangely, lust, and did not move my hand away like I probably should have. Quicker than I imagined, he had his member out and my hand was wrapped around it as he was kissing me. Unbidden my hand began to stroke him, the velvet hardness so different it seemed from my own. He lay back and all at once I had a handful of little proteins. He gave me his hanky and I wiped my hand as he kissed me again. Soon after that he took me home.

As soon as I was in my room I knew for sure that I did not want to go back to being my old male self. I felt no shame at what I had done for David, rather I was elated that he found me sexy enough to ask out and then try to have sex with. All I had to do was tell my family. I think they all knew except dad, and he would take it the hardest. On my bed was a nightgown, which I put on and went to bed. In the morning I wore it to breakfast, my breasts and homemade fake vagina clearly visible through the thin blue material, which was my objective. Mom chided me about it, but when I told them I was done being a boy all she did was say she already knew that. Dad however was angry at me.

"You're a male and damn it should stay a male!"

"But I can't dad, not any more, not after what Dave and I did."

I left it vague so that his imagination would make it worse than it was.

"Just what did you and Dave do!"

"We went out to the show, and I let him kiss me!"

By that point I could not take it any more and started to cry as I ran to my room.

I slammed the door shut, but mom came in right after me and closed it. Just like she did when I was a child she held me to her breast and waited until I stopped crying.

"Janet, it was obvious that you liked dressing as a girl, especially when I saw you in that green dress. Your father however is having a very hard time accepting the fact that his only son wants to be a girl after only a few days. And what you did down there was cruel and you know it. I know a little about men that want to become women, and I'm having trouble understanding how you decided to become a girl after so short a time, care to tell me?"

"It was like a light turned on after my trip to the salon mother. I knew right then that this is the way I should have looked all along and wanted to stay this way. The way all of the guys looked at me, like I was sexy, made me wonder why I ever wanted to be anything but female. Now David wants me, and I want him! He kissed me and my brain went numb mother. I… I gave him a hand job! Do most males do that to another male? No! Only a girl does that, and I'm a girl!"

I was crying when dad came into the room.

"I do not understand why you would want to give up being a male, but you're old enough to make that choice, so I'll go along with it. But you will have to follow the same rules Gretchen does. From now on you are not to wear any clothing that can be considered male, and in fact after we return from church I want you to clean out your closet and remove all of your male clothing. We'll give it to a local charity on Monday. Do we all understand the rules?"

I jumped up and hugged him as hard as I could, and kissed him on the cheek.

"Thank you dad."

"Get ready for church, we almost enough time to get there."

He left the room with me looking at mom.

"Did he mean that?"

"I don't think this is the time to question it, just do it if this is what you want, but by the tone in his voice I would say that your about to suffer some cultural shock. Get ready for church dear, we'll wait for you."

I wore the pink suit with white heels and blouse and a minimum of jewelry. David was there with his family as was Mike. He looked at me and smiled, but David and I sat together with my family. He was showing everyone that I was his woman I think. I introduced him to everyone, with dad smiling widely at the time. The service was the usual hour long, and as we walked out the police went up and arrested Mike for rape! I myself heard the officer say that Stephanie had pressed the charges! As they took him away David walked me to the car.

"You're Gretchen's brother aren't you?"

I knew that sooner or later everyone would he to know, but I never expected it to be so soon. If I had to tell anyone it would have to be David, he deserved it.

"I was, now I'm her sister in almost every way David. I'm sorry I deceived you, and I'll understand if you don't want to be seen with me."

"It's not that Janet. You're a beautiful woman by any standard and I like being with you. I'm just confused right now because I'm still attracted to you even though I know that you're not a female."

"Don't worry David, I like me this way too."

He and I were both confused by our relationship because of our mutual attraction. I was about to say something when dad walked up and asked if he could talk to David a moment, and I was left standing there alone.

I watched as dad and David talked, more dad talking and David listening I think. Mom came up and took my arm and pulled me back into the church.

"Your father wanted to talk to David. Man talk he said, which by definition leaves us out, but you are certainly what they are talking about. This afternoon I want you to talk to a friend of mine, and if she agrees you'll be put into the transsexual program at the hospital. Is that what you want?"

I nodded my head and watched as dad and David shook hands and walked over to us.

"Can I steal Janet for the afternoon Mrs. Grant?"

"She has an appointment at 4, so as long as you get her there on time, of course."

He took my hand and almost dragged me to the car, and then drove me to his house.

"I wanted you to meet my parents Janet."

This was a very big step and told me he wasn't very worried about me.

His mother was a darling woman, his father was polite and both of them looked at me like I was going to steal their son away right then. But we all managed to get along and before we left, I had his dad eating out of my hand so to speak. His mother was smiling, so I assumed that I had passed the test, whatever that was. He drove us back to the park, and once again he kissed me, often and hard, which I did not resist. Then he took me to the lab, and when I asked him, he joined me. The doctor and I talked, then she gave me a prescription. When I told David what it was for, he smiled and told me that he could not wait that long, and to my surprise he stopped at a motel!

I stood in front of him and slowly took my jacket off, then his shirt. My skirt followed by his pants, his socks and my pantyhose. When I was down to my bra and panties he could not stand it any more and swept me off my feet and put me on the bed. In a fevered lust I yanked his briefs down and his manhood jumped out and hit me in the face as he pulled my panties down. My small triangle of pink was holding me in, and strangely I was not erect or even felt like I wanted to be. He was kissing me all over and I pushed him on his back and started to nibble on his ears and worked my way down, knowing full well what I was going to do.

"You're a vixen Janet Grant! But you're my vixen, and I want it to stay that way."

I showed him one more time that I wanted that too.

Four months later I removed the breastforms because I no longer needed them, and the padded pantybrief was a thing of the past. By the end of the year my breasts had grown to a full C cup and I wore a size 12. What started as a favor to my sister became a reality for me, something I discovered and have come to love. In less than a year I will be a complete woman and David will finally be able to make love to me like a normal woman. I think I can guarantee that he will walk funny afterwards because I am going to do my best to sap him of all of his strength.

Mike? Well, he was convicted and sent to prison where he himself was raped and contracted AIDS. They say he has a few more months to live.




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