My Ken Doll Part 1 of 2

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My Ken Doll

By Zylux

Part 1 of 2

After catching her younger brother going through her closet, a teenage girl strikes a deal, one in which she agrees to satisfy his curiosity and he agrees to help her realize a childhood fantasy.

I’m so glad I was born a girl. Girls have it so much better than boys. We get to dress up in so many pretty and different things of every shape and sensation. Boys just have pants, jeans, and shorts that all look and feel pretty much the same. Oh sure, they can get fairly formal, but its nothing like the range that girls formal wear comes in. We can out shine the boys anytime and there’s nothing they can do about it. Even our names sound better, lyrical even, conjuring up serine images, just like my name, Laura. Of course that wasn’t wasted on me. I would often dress up and parade around the house enjoying, and expounding, on the wondrous feel of my clothes, especially when Mike, my bratty brother was around.

Mike is five years younger than me but is nearly my size and shape, only just about a head shorter in height. He took after our father who is over six foot while I took after our average height mother. While I had a slight advantage in height, he had the advantage in strength which meant that I couldn't boss him around or even fight back. Combine that with the mind of a child and one has the recipe for his making my life miserable, something he took full advantage of. My teasing him with my clothes was my way of getting back at him for all the mean things he would do. Admittedly, I had no idea just what effect my actions had on him as he would act uninterested and didn’t appear to even notice me. I was soon to find out.

It all started after a weekend during which I had gotten a new emerald green, satin evening dress, and a brown, wool skirt suit. Of course I showed them off in front of Mike, who for once, seemed to pay a small bit of attention to what I was doing. That was odd enough, but it didn’t stop there. For the next few days he acted strange, impatient, like he couldn’t wait for something to happen. It quickly became a mystery that I just had to solve and as it turned out, I didn't have long to wait.

It was the following Thursday evening when the mystery began to play out. My parents had decided on a family night out. Mom had had a very busy day and didn’t want to cook. Dad’s day hadn’t been much better and he wasn’t in the mood for an eclectic mix of leftovers. A restaurant and a movie seemed to be the best solution. I was thrilled at the idea but my brother opted out, claiming to have too much homework to do. I couldn't remember when he last willingly did his homework. It was always a struggle to get him to do it, and then he only did enough to get by. He had to be up to something and I was going to find out what.

I left the house with my parents but just before getting into the car, I “remembered” that I had a big project to do and should stay and get a good start on it. My parents seemed to like the prospects of an evening out by themselves and quickly granted me permission to stay home. I watched my parents drive off and then snuck back into the house and made for the hallway leading to my bedroom. Trying to be as quite as possible, I moved down the hallway coming first to Mike's room located in the right front corner of the house. At the entrance to his room the hall made a short 90 degree bend that led to our common bathroom in the right back corner of the house and my room on the left side of the hall opposite the bathroom. The door to Mike's room was open but he wasn't in the part that could be seen from the hall. Moving as quietly as possible I approached Mike's room stopping just outside the doorway and leaned forward just enough to see the whole room. Mike was not there. Just then a noise came from my room and I continued on, again stopping just short of the doorway. I ever so carefully peered around the door jam.

Mike was at the far left side of my room standing in front of my wall length closet with his back toward me. He had opened my closets double folding doors and had started to search through my dresses, pausing every so often to run his hand over one. This continued until he came to one dress that seemed to capture his full interest. This one he took hold of by the hanger and pulled from the closet. It was my favorite dress.

My favorite dress is a stunning, red satin, strapless formal gown that I started obsessing over two years prior, soon after I had turned fifteen. It's very tight fitting from the bust to the waist with the skirt portion coming straight out from the waist then hugging the hips, tapering down to the ankles. There is a left side slit to mid thigh, far more than what one needed to be able to walk in it. Attached to the waist is a long wide sash that could be wrapped multiple times around the waist, or be tied in back in a large bow, or an ascot with ends descending to the floor. The overall look was very sexy and way too much so for a girl of only fifteen years, but I just had to have it. Mom was very much against my having that kind of dress at such a young age and refused to buy it for me. After much pleading on my part, she ended up saying that if I wanted it that badly, then I would have to earn the money to buy it. She probably figured I wouldn't be able to, or would lose interest. Well, it took nearly a year of babysitting and running a lot of errands for other people, but I did earn the money just before my sixteenth birthday and Mom had to let me buy it as we had agreed. Of course, getting her to let me wear it outside the house was another thing.

I watched my brother hold my dress up at arms length by the top of the hanger and look it over. He turned the hanger around and looked over the back of the dress with his attention coming to rest on the hidden back zipper. Mike seemed hesitant about something, kind of indecisive. Then he took a deep breath and as he exhaled, he reached for the zipper with a visibly shaking hand. I watched in shock as Mike took hold of the zipper and pulled it down. He stood there for a moment, just looking at the back of the dress, then again nervously reached for the dress, this time removing it from the hanger. He placed the hanger on the closet door knob and then moved to the right of the closet. With gentle care, he laid the dress face down on my bed. He again paused for a moment, and then started to strip, stopping when he was left with only his undershorts on. Mike then picked up the dress, held it up in front of him and stared at it. He took a deep breath and as he slowly exhaled, he started to lower the dress down in front of him. I stared in disbelief as I realized that my brother was about to step into, and put on, my dress, MY FAVORITE DRESS! I quickly become outraged and was about to put an end to what ever perversion he was about to engage in, when a thought came swirling up from my childhood memories. It caused me to pause and rethink about how I was going to handle the situation.

When I was much younger, I used to have a certain fantasy when I played with my Barbie dolls, a fantasy that went unfulfilled because of a physical size difference between Ken and Barbie. It was something that I had forgotten about when I had outgrown playing with dolls but had apparently been rekindled by my brother's actions. A thought occurred to me, maybe I could coerce Mike into helping make my fantasy a reality. But it would take an understanding sister, not threats, to pull it off. Taking a position in the center of the doorway with arms crossed and leaning against the door jam, I confronted my brother.

"I think that's too sexy for you just yet. You should start with something more conservative until you become comfortable wearing girl's clothes."

Mike whirled around to face me, dragging the dress along with him. He stared at me with his eyes and mouth wide open in both shock and surprise.

"SIS! Wh…what are you doing here? You went with Mom and Dad."

"You were acting odd, even for you, and I thought I had better stay and keep an eye on you. So, just what were you planing to do with my dress?"

"Nothing, just leave me alone. I don't have to say anything to you."

He let go of the dress, letting it fall to the floor in a heap, gathered up his clothes and started for the door intending to bully his way past me.

"Your right, I can't make you talk to me, but you will have to talk to Mom and Dad."

"What? You'd tell on me?"

"What choice do I have? I don't know what perverted thing you were going to do with my dress, my FAVORITE dress."

"Look, I didn't mean any harm. It's that, well, your always bragging about how great your clothes feel and how lucky you are to be able to wear such nice things. I just got curious and wanted to see just what the big deal was, that’s all. You aren’t really going to tell on me are you?"

"Why didn't you just ask me? I would have understood."

"What, come up to you and say, 'hey sis, can I wear your dress?' Who knows what you would have thought of me, or said?"

"When you put it that way, you're right, I probably would have called you all kinds of things. But you already said the right thing, that you are curious, and I can help you. That is if you would be willing to do something for me in return."

"That depends, what do I have to do?"

I entered my room, headed for my open closet.

"I want you to be my Ken doll…"

I paused for a moment to sweep my hand up and out towards my clothes.

"But with Barbie's wardrobe."

"You want ME, to let YOU, dress ME, in YOUR clothes?"

"Why not? You want to try them on, it's perfect."

"Look, I just wanted to see what the big deal was about wearing a dress, it's not like I want to try on everything you've got. Can't we come up with some other deal?"

"Not really, besides girl's clothing can offer far more sensations than you will get from trying on one dress, and I can help you experience all of them if you are willing to let me dress you up from time to time."

Mike was clearly at a crossroads and couldn't make up his mind as to which way to go. He didn't like the idea of being in my control, having to wear what I wanted. But then again there was that sexy red dress he had picked out, the one now on the floor. It was obvious that he wanted it as he kept glancing at it. That dress was the key to my fantasy.

"I'll tell you what; I'll let you wear my favorite dress when I think you're ready for it. So, have we got a deal?"

"Can I back out of this any time I want without you saying anything or telling on me?"

"Yes, I promise."

"You won't tell anyone, not even your best friend?"

"Not even a hint; this will be our little secret."

"Well, okay, deal."

"Great! Now take your clothes to the bathroom along with your pajamas. Oh and there’s something you will need to put on."

I moved over to my dresser and pulled open the top drawer.

"Bathroom, pajamas, what for?

"It's a precaution in case Mom and Dad come home early. You just run into the bathroom, take off my things, put them in the hamper, and get in the shower. They will never know what we we're doing. Here, these will do."

"Panties, you want me to put these on? Why? Can't I just wear my shorts?"

"They are quite different from your shorts and are necessary if you want to fully experience the feel of wearing girl's clothes."

He didn't appear to be buying my explanation, but took the nylon panties anyway, and then headed off for his room. I stood there watching him leave my room in disbelief, not fully believing that my bratty brother, who had never done anything for me, had just agreed to let me dress him in my clothes. It was a side of him that was totally unexpected, but reasoning it out would have to wait as I needed to pick out something to dress him in. I took a step toward my dress and bent down, reaching out to pick it up from the floor. Turning back to the closet, the hanger was plucked off the doorknob and slipped into the hanging loops. The dress was zipped up and put back in its place in the closet. I then scanned over my wardrobe, but with so many choices, it was quickly becoming difficult to choose. As I tried to decide, another thought came to me. Mike was looking through my dresses, and he admitted he wanted to experience wearing a dress, if I obliged him, then he just might decide that’s all he wanted and would back out of our agreement, his desires for my favorite dress not withstanding. That would leave me far short of what I wanted. Better to start with skirts for my wants and keep the thought of wearing a dress for enticing him into another session.

Mike returned to my room wearing only my panties and looking a little sheepish. Not wanting to make him any more embarrassed, and there by possibly losing the opportunity, I got to work dressing him. Most of my skirts have a liner but I wanted to intensify the feel of the liner rubbing against the lower body and I had a pretty good idea as how to do that.

From my dresser, I pulled out a nylon half slip and held it down in front of him. Mike put a hand on my shoulder to steady his self and stepped in. I wiggled it up his legs making sure it flirtingly caressed them. The elastic waistband was allowed to snap in place around his waist. As I retrieved a camisole from my dresser, I thought about a bra. But I quickly decided that that would most likely exceed his limits. It would be best to introduce it in a future session.

“Put your arms out in front of you so I can slip this on you. OK, now raise them up and I’ll pull it down into place. There you go. Well, go ahead touch them, rub your hands over your body. Feel how different girl’s underwear is from boy’s underwear.”

I left Mike to explore the new world he had stepped into and headed for my closet. I had decided on what to dress him in. My new brown, wool skirt suit would be perfect for his first skirt. I decided to pair it with a burnt orange satin blouse with a wide, folded in half collar that was close fitting around the neck. It buttoned up in back which presented a smooth, sensual look in front that I was hoping Mike would want to explore. Of course, it also meant that he couldn't take it off without my help, giving me some leverage if he were to develop cold feet when presented with the skirt. Both were retrieved from the closet and the hangers were hooked over one of the closet doorknobs. I removed the blouse from its hanger and held it in front of me. All I had to do then was wait for Mike to finish his exploration and join me.

Mike finally looked over at me and saw that I was waiting for him. He came to me without being prompted. He was hooked. I wasted no time in slipping the sleeves of the blouse up his outstretched arms and setting it onto his shoulders. I turned him around and buttoned the blouse from the top down. Mike ran his hands over it taking in the new feel. As he turned back to face me, I turned to the suit hanging from the doorknob. He watched me intently, as I unclipped the straight skirt from the hanger. I undid the two side buttons on the wide waistband, opened the side zipper, and held it for him to step into. He steadied himself like before and stepped in. I worked the skirt up his legs to his waist, fastened the buttons, and zipped him in. He wanted to rub his hands over it but I stopped him by taking hold of the knee length hem on each side and gathering up the skirt nearly to his waist.

“Here, take hold of the skirt while I pull down and straighten out the blouse. Unlike pants, it's easier to work from under the skirt instead of trying to tuck in the top while trying to keep the skirt from falling down at the same time. There, that looks good. You can let go now.”

The heavy skirt fell down his legs, straightening out with a tug on his waist and backside. Mike obviously enjoyed it as his hands immediately went for his backside. I took the jacket off the hanger and held it in front of him. He slipped his arm into one sleeve and then turned around backing into the jacket. He slipped his other arm into the other sleeve and I fitted it onto his shoulders. I turned him back around to button it up and then stepped back to get a good look at him. He looked pretty good, and a thought came to me that with some makeup and a wig he would make a convincing girl. And what fun it would be to turn him into one. A new fantasy began to form, but it would have to wait. For now, I had other things for him to do.

"Go for a walk and tell me how it feels."

Mike walked away from me in the typical uncouth manor of a boy. He stopped short of the bedroom door and turned to face me.

"I don’t see what the big deal is. It's different but not all that great."

"Alright then, try walking more like a girl. Put one foot in front of the other as you walk and add a little more hip swing, get the skirt swinging from side to side, hitting your legs with each step."

Surprisingly he did as I suggested and did pretty good, although it was clear that it would take a lot of practice before he would have a convincing walk. Still, he got the heavy skirt moving enough to rub against his legs and backside. Combined with the half slip, it was a sensation he was clearly enjoying and I suspected he wanted more.

"Sorry sis, I just don’t see what the big deal is."

"You're lying; I can see it in your face. You're enjoying it, admit it."

"No I'm not, and I don't care what you think."

"Fine, have it your way. Perhaps you just need to spend more time dressed. Come on, let's go to the kitchen and find something for dinner."

"What, walk through the house dressed like this?"

"Why not, it's just you and me, there's no one else to see you. But you can take it all off and put your clothes back on, or you can stay here. It's your choice, as for me, I'm going to get something to eat."

I turned away from him and headed for the bedroom door. Mike hesitated for a moment then quickly hurried to join me. I had been right; he was enjoying wearing my clothes and didn't want to take them off, nor miss out on dinner by staying in my room. Mike came up close behind me until he was practically on top of me. Perhaps he was using me as a shield, just in case.

Once in the kitchen, we assembled dinner from leftovers in the 'fridge. While I was heating thing up on the stove, Mike surprised me by setting the table. It was something he only did under extreme threats. Could wearing my clothes be changing his attitude? What ever it was, I liked it.

We didn't talk during dinner and for my part, I thought about how to best continue our dress up session, pausing every so often to covertly watched mike to see how he was reacting to wearing a skirt. He was a lot more fidgety than normal, and I guessed that the interaction of the panties with the half slip and skirt liner as he sat was playing a major roll. It was an unexpected bonus that could possibly translate into getting him to wear more girly panties (and other things) in dress up sessions to come.

With dinner finished, I started to clear the table and was again surprised to find Mike helping me. For a moment, I thought he would help me wash the dishes but he just placed his dirty dishes in the sink and turned back to the table. He didn't sit down but just stood there, I guessed he was impatiently waiting for me to lead him back to my room to continue our dress up session. I obliged him, leaving the dishes for later.

Back in my room, I knew just what I wanted to do. It was time to show Mike that unlike boy's clothes, girl's clothes were more versatile and a whole new and different look could be created by just changing or adding an item or two. I took the jacket and skirt off Mike and hung them back up. I then removed a stiff yellow flared skirt from its hanger and made ready for him to step into. He practically jumped in. The skirt was pull up into place then, reaching around him, I hooked and zipped him in.

Mike took a few steps from me then started to play with the skirt. With both hands, he pushed down on the front of the skirt and looked around him to see what effect that had. He looked a little disappointed. Then he began to twist back and forth resulting in the same disappointed look. I couldn't believe my eyes. Mike was copying things I had done in front of him in the past. He had paid more attention than I had suspected and was trying to experience the same things I had. But he wouldn't be able to as I had worn a petticoat under a less stiff, but equally flared skirt and he wasn't. I could have fixed that, but didn't oblige him, figuring that I could use his desire as an enticement for yet another session. All in all, things were going better than I could have hoped for and I watched Mike deal with his frustrations while I was wrapped up in my own enjoyment. But not for long as he quickly tired of what he was doing and returned to me.

Continuing with my new theme, I unbuttoned the blouse and pulled it up and off of him without unfastening the skirt. I put the blouse back in its place in the closet and selected a white, long puffed sleeved blouse with a ruffled collar that extended half way down the front. Each sleeve ended at the wrist with a two button French cuff. It was presented to Mike and he quickly turned around and slipped his arms into the sleeves as I drew it up onto his shoulders. I turned him back around and buttoned him in, and then buttoned the cuffs. Reaching around him and under the blouse tails, I unfastened the skirt and slid it down to just under the blouse tails, then pulled it back up and over the blouse. I reached around him again, fastening him back into the skirt. The blouse tails were straightened from under the skirt as before.

I retrieved from my dresser a yellow, sleeveless, pullover sweater with a deep v neckline. Mike put out his arms and I slipped the sweater onto him over the blouse. A wide white belt was fitted around his waist and I cinched him in tight. White thigh high stockings were pulled over his feet and up his legs. White boots with side zippers were slipped onto his feet with some difficulty as they were a tight fit and I knew he wouldn't tolerate them for long. That was a shame as it was a cute outfit and a perfect pairing with his young personality. I stared at Mike, imagining him with a pixy hair cut and thinking what a perfect girl he would make. But just how do I get him to be one?

I was hopping Mike would go look at himself in my full length mirror and see just how cute he was, but he didn't. Instead he again went for a walk, adding enough hip action to his walk to get the skirt to swing side to side like a bell. He clearly liked the motion of the skirt, although he was trying his best to hide it. His play gave me the idea that I might be able to teach him how to act more like a girl and that in turn might make him receptive to entertaining my new fantasy in the near future.

"Hey mike, why don't you come sit on my bed, see how that feels."

Mike hurried over the bed, turned, and more or less fell back on to it.

"So what's the big deal, Sis? Not much different then sitting down in my clothes."

"That's because you didn't sit like a girl would. Go back and do it again, only this time walk slower, like a girl, and then as you sit down, run your hands down the back of your skirt as you sit. You know, like you've seen me do."

Mike did as instructed with much better results. The pleasant sensations he was experiencing were clearly reflected in his face. But there was no need to get him to admit that he was enjoying it, instead, I decided to plant a seed that might ensure another session of dress up.

"If you think that's different, then you have just HAVE to try sitting with a petticoat on, you'll love it, and just wait and see how wonderfully your skirt moves as you make a quick turn. It's a little secret that we girls have that boys don't know about. But I think we will try that some other time as I don't know when Mom and Dad will be back and I do want you to feel what its like to wear a tight, restrictive skirt."

"What do you mean by 'restrictive'? Are you going to make it impossible for me to move so you can force me into doing something I don't want to or you'll leave me for Mom and Dad to find?"

"No, of course not, we have an agreement, remember? I'm only doing as promised, presenting different experiences for you to try. Remember, you can call a halt anytime you want."

"Ok, I guess I can trust you, but still…restrictive?"

"Relax, it just means that it's a really tight fitting and long enough to affect how a girl walks. It forces her to take slower and smaller steps, more mature like. There's also a feeling of being vulnerable as she can't suddenly run away. It's just something that's part of the girl experience that boys will never know of."

I let my last sentence work on Mike's mind and it wasn't long before he got up off the bed and stood before me ready for the new experience that only girls could know of. As I turned to my closet, a sly smile came across my face. I was really enjoying our little dress up session and felt that I could entice him into much more with the right bait.

From my closet came a shocking pink, hip hugger, bottom of the knee length skirt that tapered to hug the legs with a short walking vent in back. The hanger also had its matching vest. But first I had to take off the skirt Mike was wearing as well as the boots. Having done that, I dressed him in the hip hugger skirt. It was a tight fit and took no small amount of effort to work it into place.

"Ok, now the hem can't be pulled up as we have been doing, so you will have to tuck in the top like you do with your shirt and pants."

"Um, this is really hard. I think this skirt is too small for me."

"That the way it's suppose to fit, nice and tight to show the boy's what a girl has to offer."

"Hey, I don't want to show anybody anything…"

"Relax; you are only going to experience the fit and feel, not the emotional experience of boys looking you over, unless you want to."

Mike tried to act like he didn't hear me by increasing his efforts with the blouse and eventually got it tucked in, then voluntarily turned around for me to hook and zip the skirt. I picked up the vest and held it behind him for him to slip his arms into the sleeves. As I fitted it onto his shoulders, he turned back around to face me so I could button him in. Taking a step back, I looked Mike over. He looked so cute standing before me waiting for instructions. I obliged him by sending him off for a walk. He got to the doorway with some difficulty and turned to face me.

"It's no big deal, see, I'm not having any trouble walking."

"But you have to walk like a girl to do so."

"So, I can do that, watch."

Mike started to walk back to me, doing even better then he had on the outbound trip. He was letting go of any inhibitions he had of acting like a girl. I turned away from him and bent down to look over a shoe rack on the bottom of my closet.

"You think so? You're not wearing girl's shoes. Let us see if you can walk in that skirt, wear … ing … THESE!"

I knew what I wanted, found them, took them from the rack and quickly whirled around shoving a pair of white, high heeled pumps up toward Mike's face.

"Try to walk with these on, or are you ready to admit that there are things a girl can do but you can't."

Mike stared at the shoes I was holding. The heels were a good three inches tall but were wide enough so that he could adapt with a little practice. I just wasn't going to give him the chance at that time, but would give him the chance to show me he could do it at a later session.

"Hey, I can do it. It's just that my feet are bigger than yours. They won't fit, so I don't have to prove anything."

"They're not bigger by much. You can squeeze into them and tolerate wearing them long enough to prove to me your right. Let's try it. Hey, you've got a shoehorn right? Go get it."

Mike hesitated and was clearly looking for something to counter with. I wasn't about to give him the chance.

"What's the matter, afraid you're going to prove yourself wrong?"

Mike didn't say anything, just stuck his nose up in the air and headed off to his room. I watched him walk away, with my gaze coming to focus on his cute little butt sashaying out the door and broke out in a big smile. This was much better than a toy Ken doll.

I used the time during his absence to get a pair of nylon footlets. When he returned, he found me kneeling on the floor, sitting back on my legs. Mike came to stand before me holding his shoehorn. I got to work by stretching one of the footlets open enough to slip onto his foot. He raised his foot and I slipped it on. We repeated with his other foot. I then placed one of the shoes in front of the appropeate foot and reached up for the shoehorn. Mike handed it to me, then put his hand on my shoulder and tried to wedge his foot into my shoe. With help from the shoehorn, his foot slipped into the shoe with little difficulty. The other foot surrendered just as easily. His feet weren't as big as we had thought.

"Okay, now let's see you walk."

"No problem, watch."

"Ha, look at you stumble. See, you can't do it."

"Sure I can, just give me time to get used to walking on my tip toes."

"And there's half your problem, you need to walk like normal, coming down on the heel first and rotating forward onto the toe."

"But these heels are far narrower than the ones on my shoes. I've never had to balance on such a small point before."

"Oh but you do, you just don't realize it. Think about it, you don't come down on the whole heel, just the very back of it and look at the shape of it, it's rounded. I'd be willing to bet that the area of contact on your shoes and these is the same. The only difference is the back of your foot is much higher off the ground when the shoe makes contact with the ground, and that is what you need to get used to."

"I don't know about that, but I'll try it your way if you will walk with me and catch me if I fall."

"I think we had better save that for next time. It's getting late and you have homework to do."

"Homework, bah! That was just an excuse to stay home."

"That's what I figured and is why I stayed home so I could see just what no good you were up to. But think about it, when Mom and Dad come home and see that you didn't do any homework, their going to think that you were up to no good as well. Do you think that they will leave us home alone and stay out late long enough for you to again explore the wonders that girl's clothes have to offer? And you do want to prove to me that you can walk in those shoes you're wearing, don't you?"

"Hey, I just wanted to see what it was like to wear your dress and that was all. I didn't have any intention of going beyond that."

"And you will get to try on my favorite dress as I have promised. You just have to earn the privilege and that's going to take time. So, if you want Mom and Dad to give you that time, then you have to start doing your homework. I can help you with it if you want."

Mike didn't say anything; he just glanced over to my open closet. It was obvious that he wanted my favorite dress and that was just what I was hoping for.

"Right, lets get you undressed. You know, you can keep wearing my panties under your clothes for the rest of tonight if you want. Just put them in the hamper when you take your shower."

Again Mike didn't say anything. He just made ready for me to undress him. Having stripped him to just the panties, I sent him off to the bathroom where he had taken his clothes. As I watched him leave, I was slowly overcome with a feeling of being in a dream world. I just couldn't believe that at long last I had a Ken doll that I could dress up in Barbie's clothes. While there was no way of knowing which of us was having more fun, I was sure that my brother would be up for more, even if it was just to earn points towards the dress he desired.

Mike got dressed and finished up his homework (with some help from me) then hit the shower as I returned to the kitchen to do the dishes, finishing just before Mom and Dad got home. They came to look in on us and seemed relieved that all was well. They were down right surprised that Mike had actually done his homework and I could see them silently planning more late night outings without us in the near future. All was going well.

Wednesday of the following week presented me with the next opportunity to play dress up with Mike. Dad came home late from work carrying a pizza box. The pizza was for us kids as he and Mom were going out. It seemed that Dad had had a frustrating day and needed to unwind. He had called Mom before leaving work and had asked her out for dinner and dancing. She of course had accepted and was going to fix something for Mike and me for dinner when Dad said that he would take care of that by stopping for pizza. I was thrilled at the prospect of being able to play with my new Ken doll again and looked over at Mike. Mike briefly glanced at me, trying to hide his feelings with a noncommittal look.

Dad put the pizza on the coffee table in the living room. Mom came into the living room carrying a couple of cold sodas and placed them on either side of the box. She and Dad then headed for their bedroom to dress for their evening out. Mike turned on the TV, and then joined me on the couch. We had almost finished our dinner by the time our parents were ready to leave. Mike seemed to take far more interest in what Mom was wearing that usual. He followed her with his eyes as our parents exited via the front door.

It wasn't long after that before we both finished dinner. I took the remnants to the kitchen then returned to the living room. Mike was where I had left him, seemingly absorbed in watching TV. Instead of joining him, I walked towards the hall leading to our bedrooms, taking a roundabout route that enabled me to slowly pass between him and the TV. As I blocked his view, he switched his attention to me, looking up at me with some annoyance. I smiled back and nodded with my head towards the hallway. He caught on to what I was up to and after looking around and acting a little shy, turned off the TV and followed me to my room.

Once in my room, I headed straight for my dresser and retrieved the same pair of panties Mike wore during our first session. He took them from me and without any prodding, headed off for his room. He soon returned, wearing just the panties. I felt so overjoyed that I wanted to kiss him, but refrained as I didn't think he would stand for it. Instead, I got to work dressing him.

I had no trouble deciding on what to dress him in as it was nearly all I could think about since our first session. From my closet came a slim white skirt that had some stiffness and weight to it. I paired it with a stiff, black, button front shirt with long sleeves and one button cuffs. It was a professional looking outfit set apart from the mundane by the visual stimulus created by placing a very dark color over a very light one. I sent him off to walk and play in it while I sat on the floor to watch him. He started out mimicking the way girls walk, but that didn't last long. Before he got halfway to the door, he started looking down and touching the skirt. He didn't make it to the door before he turned back with a look of disappointment.

"What's the matter?"

"This is the same as before, and it's still no big deal."

"There's more to girls clothes than the way they fit and feel. It's also about how they look on you and how you look in them, adding another dimension to the experience. Come over to the mirror and I'll show you what I mean."

"NO, I don't want to see."

"Why? Do you think you look silly? Well you don't. You look pretty good; in fact, I'll wager that you look better in that outfit than a few girls I know would."

"No I don't. A boy can't possibly look better in girl's clothes than a girl."

"Come see for your self, that is, if you are not scared."

I turned away from Mike to retrieve a wide red belt from my closet, taking my time so that Mike might try to sneak a look in the mirror without my seeing him. Suddenly a faint gasp came from the direction of the mirror. Turning to it, I saw Mike staring at his image in the mirror and not believing what he saw. I joined him, bringing the belt with me.

"You can see what a nice outfit that is, but watch what happens when I add this belt."

Without giving him a chance to protest or run away, I quickly wrapped the belt around his waist from behind. I was able to thread the end of the belt through the buckle just before he started to squirm. I finished fastening the belt despite his antics, then seized him by the shoulders and steadied him square with the mirror.

"Now look. See how a small change can make a big difference in the look. Try doing that with your clothes."

Mike didn't say anything and I didn't press him. Instead, I left him to look him self over while I went back to my closet to fetch the next skirt. It was to be a mini flip skirt which I was going to pair with a sleeveless shirt. But instead of buttoning it up, I would tie the ends in a knot. It would be youthful and trashy, and hopefully different enough to keep him playing dress up. But it was not to be. Mike looked at the outfit I held up before him with the same disappointed look.

"I'm tired of the same old thing. I'm going to call a halt. You can take this off me."

I was about to lose my Ken doll unless I could come up with something he would want to wear and fast, but what? My thoughts quickly backtracked to when our parents left and how Mike intently watched Mom as she walked to and out the door. And who could blame him as she looked fabulous and moved in such a graceful manor that was accentuated by the almost liquid movement of her dress.

Mom had chosen to wear a dress designed with dancing in mind. The bodice was tight fitting to the waist and was completely covered in purple sequins. There was a plain circular opening slightly bigger than her neck with a keyhole opening in back, closed by a single button and loop at the neckline. The knee length, nearly full skirt, was of a light weight material in a purple color that matched the bodice. A much heavier material had been sewn up in the hem so that the skirt would flow and move in response to her being spun around the dance floor. Even as she walked out the front door, the skirt moved in a most feminine manor. That was the key, and by good fortune, I happened to have something similar, just in turquoise, and without the sequins. I retrieved the dress from my closet and presented it to my brother with a quick turn. The heavy weighted hem caused the full skirt to dance and twist through the air, demanding his attention.

"Sure you want to quit? Wouldn't you at least want to try this on first?"

He just stared for a moment at the dress with his mouth slightly open, before trying to feign disinterest.

"Naw, but make it your favorite dress and you have a deal."

"No deal. It's too soon, but not to worry, the day you get to try it on is not that far off. That is, if you continue to be my Ken doll."

"Yeah, but our deal was that you would let me in on all the different sensations girls clothes can offer. So far, this time has been just like the first, nothing new."

"But look, I'm holding something new, a dress. Remember, you said that you were curious about wearing a dress, well, here you go."

"Yeah, but I was referring to your favorite dress, not any dress."

"No, you just happened to pick out that dress. Look, so far you've experienced a few of the various styles and sensations skirts have to offer. Dresses are just as varied and each offers its own fit, feel, and look. This is the one I want you to try first. So, put your arms out in front of you."

Mike wasn't ready to give in to me and showed it by just standing there, refusing to do as asked. An appeal to his curiosity was in order.

"This one has something unique to girl's clothes, it's a side zip."

"So, what's the big deal with that?"

"You can't step into it and pull it up. It has to go on over the head, intensifying the feminine feel a dress offers that a skirt doesn't. And I just love the way it falls down my arms, enveloping my head, and settling into place on my shoulders, conforming to my body even before the zipper is pulled up. Boys have nothing to compare with any part of the experience. So come on, put your arms out in front of you and experience the wonder that awaits you."

Mike's desire to experience the feel of my favorite dress faded into the background as his curiosity muscled its way to the forefront. I guess he just couldn't stand my being able to experience some wondrous sensation he could not because of the differences in the clothes society says each sex is limited to wear. He slowly raised his arms up in front of him. I took the dress by the hem and quickly slipped it over his outstretched arms, working it on until his hands were at the arm holes. I guided his fingers into the arm holes but not his thumbs. Instead I hooked the shoulder of the dress on his thumbs. Not wanting to give him a chance to back out, I seized his arms just above the elbow through the dress and quickly raised them up over his head. I let go and the dress floated down enclosing his head and caressing his shoulders as it straightened out.

"You can let go any time now."

Mike slipped his thumbs into the arm hole and the dress finished it journey down his arms, settling onto his shoulders. He didn't know it, but he was now trapped in my dress, as it was highly unlikely that he knew how to get out of a side zip dress without help from me. I took my time with the zipper and the keyhole button as well as straightening out the skirt before sending him off to explore.

As I watched Mike walk away, I started to think about the next outfit but didn't get too far, as a thought occurred to me that he may not be up for more given his earlier attitude. It might be a wise precaution to try and get as much out of the dress as I could and that would require something that would grab his interest. Fortunately, our first session had ended with the perfect enticement. I turned to my closet and hunted down the same pair of white, three inch high heeled pumps. I also picked out a pair of nylon footlets from my dresser and returned to sit in front of my closet to watch Mike play. He was twisting back and forth, making the skirt fly out and wrap around him.

"Hey Mike, remember that's there's also a visual sensation girl's clothes can offer. Try doing that in front of the mirror."

Surprisingly, he did as suggested and seemed to enjoy the experience. Taking advantage of his mood, I held up the shoes.

"Hey Mike, remember these? Want to give them another try? Go get your shoehorn."

Instead of making a protest, Mike hurriedly headed off for his room with the skirt of the dress trailing out behind him. He returned almost as quickly, coming to stand before me ready to hand me the shoehorn. I got the shoes on his feet with the aid of the footlets and shoehorn as before and sent him off for a walk, ready to tease him before offering him my assistance.

But Mike had a surprise for me as he did far better than his first time. Oh sure, he stumbled here and there, and looked a little awkward now and then, but all that gradually disappeared with each trip across my room he made. It quickly became clear that he had been practicing, but how? There had been no opportunity to use my shoes as I had been home when he was. Could he have been wearing Mom's shoes? But again, there had been no opportunity. It was a mystery that would remained unsolved as I knew that he would never clue me in no matter how much I were to plead with him. And that was probably what he wanted. Instead, I would employ a different tactic. I would first act like I didn't suspect he had been practicing, and then hit him with a new challenge, one that his ego could not turn down.

"Bravo! You've got it. I have to admit, you can walk like a girl while in heels."

Mike started to strut around with a smug look on his face.

"Oh, feeling confident are we? Okay then, let's dance."

"What? No way!"

"Afraid to dance with your sister, or are you afraid you can't do it in heels? Come on; show me that you truly are comfortable wearing heels. It's one of the requirements you have to meet before you can wear my favorite dress."

"Alright, I'll do it."

"Great. Now, since I'm the one wearing the pants and you're the one wearing the dress, I'll lead."

I put on some dance music in my portable tape player and proceed to lead Mike around my room, slowly at first, adding quick turns and twirls as he adapted. He seemed to really enjoy the way the skirt flowed around him and it was a long time before he tired of it and called a halt. I was really enjoying that session and tried to get him to try on another dress as I undressed him, but he wouldn't do it and headed off to his room to do his homework. Disappointing, but it didn't bother me much. After all, given the enjoyment he had just displayed, I was sure it would be no problem to get him to submit to the next session.

It was two weeks later on a Saturday morning that I was presented with my next chance to dress up my Ken doll. Mike and I had finished with breakfast and had moved to the living room to watch TV. Our parents were still sitting at the kitchen table reading the paper when Mom had come across an ad in the entertainment section for a play she suddenly decided she wanted to see. She showed the ad to Dad and he smiled back and gave an affirmative nod. I looked over at my brother and gave him a knowing nod, but he just shrugged his shoulders, and acted indifferent.

All the following week, mike continued to act like he didn't want to engage in another dress up session. He rebuffed my every attempt to talk to him about it with increasing annoyance to the point where I began to think he really wasn't fooling, his desire for my favorite dress not withstanding. He maintained that attitude right up to Friday morning, the evening of which our parents were to attend the play. It was most perplexing given his enjoyment of our last session, and that quickly turned into frustration, for it was the perfect opportunity to dress him. After all, there was no school the next day, nor was there any homework to do, and we knew when our parents would be headed home. An opportunity not to be missed, and I was not about to let him spoil my fun. I need an enticement, but what?

All that day at school my thoughts were less on lessons and more on how to get Mike to once again assume the role of my Ken doll so I could dress him in Barbie's clothes. I still hadn't thought of anything, short of extortion, by the time we had gotten home from school. A couple of hours later Dad arrived home from work and started to read the paper to relax and unwind before getting ready for the evening out. I took a break from my thoughts by visiting Mom in the kitchen. She was preparing what I thought would be dinner for all of us, but it was actually something she could leave for just Mike and me. She explained that she and Dad were going out to dinner before the performance. Great, that meant more time for me to dress up Mike, IF I could find a way to get him to do it.

Mom finished fixing dinner and left it on the stove as she headed off to the master bedroom to get ready. I retreated to the living room where Dad and Mike were. I sat down on the sofa opposite from where Mike was sitting on the couch. Dad soon followed Mom, leaving Mike and me alone in the living room. It was a signal that I was running out of time and the added pressure wasn't helping my thought process. I quickly sank into a pit of isolation, blocking out everything around me, concentrating fully on finding a way to bust through the wall Mike had thrown up between us.

Suddenly, I was yanked from the pit and back into the real world by a sound, a subtle, but attention grabbing, rustling sound. Our parents had finished getting dressed and had come into the living room to give us instructions for the evening before leaving. It was Mom making that sound, or rather her gown. She was wearing a dark ruby red satin, off the shoulders with a wide collar, formal gown. It had an elegant ankle length full skirt with a black lace overskirt. Under the skirt, she was clearly wearing a full, lacy petticoat.

As our parents headed for the front door, I glanced over at Mike. He was focused on Mom, turning his head to follower her more with his ears than with his eyes. It was the sound, that seductive, rustling sound, and it was casting a spell on my brother. My tired mind seized on that bit of luck and quickly formulated a way to exploit that spell to both my advantage and pleasure. All I had to do was get him talking about how nice Mom looked (and sounded) and dinner was the perfect opportunity to do that. As the front door closed, I turned back to Mike.

"Hey, I'm getting hungry and it's close enough to dinner time. Let's go see what Mom left for us."

"I can wait. You go ahead, I'll eat later."

"You want me to bring dinner out here? We can watch TV while we eat and talk a little."

"No, I'll eat in the kitchen after you. Now let me watch this program in peace."

Clever boy, Mike had been ahead of me all week. He figured out that the only way I could get him to be my Ken doll again, was to sweet talk him into it, but he was too smart to even give me a chance to do it. He knew, given our agreement, I could not use force or extortion. He probably felt, given the experiences of our last session, that I didn't have anything left to use as a means of enticing him to let me dress him now. He was leaving only one path open, to negotiate on his terms, and I knew what his terms were. Too bad he didn't know that I did have an enticement that would cause him to tear down his wall of resistance for me.

I withdrew to the kitchen and plated my dinner. Eating quickly, I soon finished and took the dirty plate and utensils to the sink to wash and dry them. I returned to the living room and sat down on the coach next to Mike, knowing that he would not like that and would move off. I would use that to hurry him into eating dinner instead of waiting.

"That was really good, sure you're not hungry?"

"It does smell good. I'll just go check it out. This program is over anyway."

He wasn't fooling me; I knew he just wanted to get away from me. It was just what I wanted. My plan was to corner him in his room where I could deploy my new enticement without him being able to run away. His desire to stay away from me would make that easy. I just had to be patient and let him set the pace.

It wasn't long before I heard the sound of dishes being put in the kitchen sink, signaling Mikes return to the living room. I was ready for him.

"All finished? Great, let's go to my room, I've got just the thing for you to experience. You'll just love it. If you think you had fun last time…"

"NO!"

Mike headed for his room with a smug attitude, firmly in the mistaken belief that he was in control and that if I wanted to dress him, and then it would only be in what he desired, and that being, my favorite dress. I followed him at a more leisurely pace, looking into his room only to make sure he was there, and he was. Continuing on to my room, I headed for my dresser where I picked out a plain pair of panties with my left hand and then moved to my closet and opened the doors. Quietly as I could, I removed the hanger on which was suspended the fullest, nosiest, most totally feminine petticoat I had. Holding the hanger in my right hand out in front of me and the panties still in my left hand, I made my way back to Mike's room in nearly total silence. I took a position at the left side of the doorway, holding the petticoat so that it filled the middle of the opening with me peering around the door jam and over the petticoat, and engaged my brother in battle.

"Hey Mike…"

"Go away! I'm not interested in anything you have to say."

"I just wanted to see if you remembered the yellow skirt you wore? The one you sat on the bed in and played around with like a girl? Imagine doing all that again, but with THIS on underneath it."

Curiosity quickly got the better of Mike and he turned to face me. His attention instantly focused on the petticoat, but his reaction was not what I had hoped for.

"No! It's too frilly and little girly! I'd look silly wearing that! There's no way you are going to dress me in that, so forget it."

"But you can't see it once a skirt or dress is put on over it."

"Oh yeah? I've seen it peek out from under the hem when you wear one."

"So? It's only a hint of what's there. You only see the wondrous effect it has on a full skirt. You don't think I look too girly when I wear one under something, do you? And what about Mom tonight? She was wearing one."

"Well, maybe. But I'm still not going to let you dress me in one."

"Why not? Don't you want to experience something new?"

Mike didn't answer; he just turned back to his desk. It was time to up the ante by shaking the petticoat side to side.

"Listen, isn't that the dreamiest sound? We girls just love it. It reinforces the feel and the look that a petticoat provides. It all combines to make a girl feel EXTRA special when ever she wears one. It's something boys can't experience as they have nothing that comes even remotely close to a petticoat. They will never know of any of the secret wonders that they are missing, unless they know someone who is willing to let them in on the secret."

"Like, you've been doing with me."

"Right, so, do you want in on the secret?"

"You won't laugh at me, will you?"

"Of course not. Get your pajamas and come on. Look, I promise I won't do anything to spoil your special secret experience."

That got him. Mike got up from his chair, grabbed his pajamas off the end of the bed and came towards me. I moved the petticoat out of the doorway, presented my panties to him, and then turned away towards my room moving my right arm out from my body slightly so that the petticoat would rub against the hallway wall. I even give it a subtle shake to generate even more noise. Mike hesitated for a moment, as if he were listening to the wondrous rustling sound, before making for the bathroom to change.

Back in my room I laid the petticoat on the bed and turned to my closet to choose something to dress my Ken doll in. I selected a orange and white, large checked pattern sundress which I also laid out on the bed. Finally, I took a full slip from my dresser and turned to see Mike come into my room wearing just the panties. He came to me but his attention was directed to what was laid out on the bed. Not wanting to give him any time to think about what he was about to get into, I quickly grabbed his wrists and raised his arms up and out in front of him. I slid the slip up his arm and pulled it over his head as he obligingly raised his arms up over his head. The petticoat was plucked from the bed with a flourish resulting in lots and lots of that wonderful rustling sound that caused Mike to follow its every move with his eyes. I stretched the elastic waist band open, and held it down in front of me motioning with my head for him to come and step into it. As if he was under some kind of spell, Mike slowly came to me, placed his hand on my shoulder and stepped in. I quickly worked the petticoat up his legs, letting the waist band snap into place around his waist.

Mike stared down at the layers of stiff lacy fabric encircling his legs as I grabbed the sundress from the bed. He was clearly uncomfortable standing there in something so girly, so when he noticed the dress being held open in front of him, he quickly raised his hands up and into the dress. I pulled the dress up his arms, over his head, and down into place on his shoulders. Turning him around, I zipped up the back zipper before fluffing out the skirt over the petticoat again and again. Mike stared down and watched me without making the slightest protest. I could not believe he was allowing me to do something so girly while dressed in something so feminine. A thought came to me that this might be the time to take him to the next level, but first I would let him play.

As mike explored the wonders offered by a petticoat, I would suggest things for him to do, and he did until, while doing an energetic, complete twirl, he caught himself in the mirror and stopped dead in his tracks.

"No! Get this off me, it's too little girlish!"

"No it's not; a sundress is a very mature look…"

"Its a little girls dress and I don't want to wear it any longer."

"I can prove it isn't, just give me a second to get something from the far reaches of my closet.
It’s a blouse I no longer wear. It's my old white blouse with ruffled front and short puffed sleeves. Here it is. Put this on under the dress and you will see what the 'little girly' look really is."

"No way! That makes it even worse."

"You've seen me wear that dress and you've seen Mom wear a sundress, do we look little girly?"

"No, but on you it looks…"

"I've got it! I know what's wrong. It seems little girlish because you don't have a big girl's chest. That, I can fix."

I quickly went to my dresser and pulled open the top drawer. I grabbed a plain white bra and presented to Mike.

"This will give you a more mature look."

"NO! You're going too far with this. I'm not going to wear a bra, ever!"

"What's the big deal? You've got a petticoat on, don't you? That’s very feminine, but I didn't hear any complaints from you."

"But it's not the same thing."

"Sure it is. A bra isn't any more feminine than a petticoat, their both just part of girl's underwear, although a petticoat is rarely seen nowadays."

"I don't care! I'm NOT wearing a bra. Now get this little girls dress off me."

"Okay, you win. Hey. I was just giving you the opportunity to experience something you can't as a boy. I didn't mean to upset you, hey, I'm sorry. Turn around so I can unzip you."

Mike turned around and I quickly unzipped the dress. Taking hold of the skirt, I started to pull the dress up. Mike raised his arms up over his head, allowing me to pull the dress up his arms and off. After straightening out and hanging up the sundress, I took down the hanger with the flared yellow skirt he had worn before. I decided to pair it with a yellow turtleneck pullover sweater I retrieved from a lower drawer of my dresser. Holding the sweater over and above the skirt, I presented the outfit to Mike.

"Now I know that you can't think this is 'little girlish' as you have worn the skirt before. So there is nothing to stop you from exploring this outfit same as you did before and see first hand the difference a petticoat makes."

Mike stared at me with a scowl.

"Remember the fun you had exploring wearing this skirt like a girl would? Don't you want to see what new fun you can have with a petticoat on under it?"

Mike continued to stare at me, but the scowl had faded away.

"Come on, besides, you need to show me that you can act like a girl. Its one of the things you have to be able to do before you can wear my favorite dress."

"But I don't WANT to act like a girl."

"Are you sure? No? That's too bad as you have gotten so close to earning the privilege of wear my favorite dress. It would be a shame to stop now."

Mike said nothing, he just stared at me in surprise with his mouth slightly open for a moment, then made ready for me to dress him. After first slinging the sweater over my shoulder, I unclipped the skirt from the hanger and tossed the hanger onto my bed. I dressed Mike in the skirt, getting him to help me by using his hands to push the hem of the petticoat into the waist opening of the skirt as I worked the skirt up his legs. Next, the pullover sweater was slid up his outstretched arms and pulled down over his head as he raised his arms up. The bottom of the sweater was arranged over the flared out skirt which in turn was straightened out over the petticoat. The outfit was completed with a black belt around his waist, and open toed black sandals on his feet. He looked absolutely darling, even without looking like a girl, although the sweater was screaming out for a well stuffed bra.

While I didn't need to prompt him to go for a walk, it was clear that he was just humoring me. But it wasn't long before the petticoat worked its magic. Mike began by pushing down on the front of the buoyed out skirt and looking all around him see what effect that had. He resumed his walk but in the manor of a girl ending with a quick turn and him watching intently the effect that had on the skirt. The look on his face said that he wanted more. He looked up and over to my bed then strutted over to it. He turned to sit down on the bed, smoothing the back of the skirt with his hands as he sat. He put his hands on the bed just beyond the sides of the skirt.

"Put your hands together, interlocking your fingers and drop them in your lap."

"That really lifts the bottom of the skirt up, how do you keep someone from looking up it?"

"Well, that's a very astute observation and I'll let you in on how we girls do it. First, put your legs together. Now point your knees slightly to the side and move your feet to the opposite side. Good, just move your hands to your leg, pointing to your feet and you've got it."

"Are you sure this is the way girls sit? I can't recall ever seeing one do this."

"Its not done much any more but you have seen girls sit like that, you just didn't notice because they were girls and you weren't interested in them."

"You might be right. How come they don't sit like this any more?"

"Because today's girl just doesn't want to make the effort it takes to be a proper little lady"

"I think if I were a girl I would want to go to the trouble."

"With a wig and some expertly applied makeup you could look like a girl. Hey, you defiantly can act the part, why not look the part?"

"What? Boys can't look like girls."

"Sure they can and I can prove it for I know someone who can turn you into a convincing girl, and that just happens to be a pet project of hers."

"What, turning boys into girls? That's weird."

"No, she just wants to put her makeup skills to the test. She's studying to be a theatrical makeup artist. To her, making up a boy to look like a girl or a girl to look like a boy is the ultimate challenge."

"Okay, but it's kinda strange for a boy to want to look like a girl, which…I…do…NOT."

"What about for Halloween? It would be the perfect excuse and you will get to wear my favorite dress."

"What, did you say your favorite dress? You really mean that?"

"Of course. You've shown me that you can act with all the mannerisms of a girl, walk and even dance in the high heeled shoes that such a dress would demand of its wearer. All that is left is to LOOK like a girl on whom that dress would look appropriate. So, if you give my friend a free hand in making you up as a girl, then yes, you will get to wear my favorite dress. Is it a deal?"

"Wow, I don't know, I mean, I don't want anyone else to see me in your clothes. What's she going to think about me? "

"Nothing, my friend does not know about you being my Ken doll. Look, I'll come up with something to do with Halloween that won't cause you any embarrassment. You and I will be the only ones who will know the real reason."

"I don't know, I mean, well… Look, I just can't have someone else seeing me. But hey, you're good with makeup; you can turn me into enough of a girl to be able to wear your dress. Deal?

"Sorry, no. I'm not that good. I'm afraid you would just look like an effeminate boy in makeup. Hey, I will be wearing that dress long after you, and I don't want to be recalling an image of you wearing it every time I pull it from my closet."

"But we had a deal and as you have just said, I've met every one of your requirements. And now I'm willing to let you make me up as a girl. A deal is a deal."

"But I can't convincingly make you up as a girl. My friend Crystal can. Look, it's just that my favorite dress is really special to me, and I want you to experience everything I do whenever I wear it. To do that, you will need to see yourself as a girl and think of yourself as a girl when you're in that dress. It's the total experience or nothing."

"But your friend will laugh at me."

"No she won't. She will be too proud of her work to even think of you as a boy in a dress."

"I don't know about this. I gota think about it."

"Don't take to long, Halloween is nearly here."

It was disappointing, but I knew all was not lost. Mike just needed one more push and the opportunity to apply said push came the following day. It was Saturday and everyone pretty much followed their usual routine. Right after breakfast, Mom and Dad went out shopping. Mike settled down in the living room to watch some ballgame on TV. I headed for my room, to change.

I stripped off the sweat shirt, jeans, and canvas shoes I was wearing. My shoulder length hair was put up and pulled back into a loose bun. Makeup was next, and I wasted no small amount of time making myself as glamorous as I could. Only when I was finally satisfied with the results, did I turn my attentions to what I would wear, my favorite dress.

I took hold of it by the hanger and pulled it from my closet. Holding my dress up at arms length by the top of the hanger, I look it over before turning the hanger around to gain access to the hidden back zipper. I paused for a moment, to revel in the thrill of putting on my favorite dress. I took a deep breath to calm my excitement and as I slowly exhaled, took hold of the zipper and pulled it down. I stood there for a moment, just looking at the back of the dress, before removing it from the hanger. The hanger was placed on the closet door knob as I lowered the dress down in front of me. I stepped into the dress, being careful not to pin the dress under my foot, then stepped in with my other foot with the same precautions. The dress was pulled up with a little wiggling to help get the tight fitting dress past my hips. Once it was in place, I reached behind me and pulled up the zipper. I was at long last in, and loving it. All that was left was to slip on the matching three inch heeled pumps, and head for the living room, after a brief pause to check myself out at the mirror, of course.

I sashayed into the living room and headed for the TV stopping in front of it, obstructing Mike's view. I slightly turned toward Mike but kept my left side presented to him and struck a sexy pose with my left leg sticking out the long side slit. I then started to run my hands over my body, bending and twisting as if I were enjoying some inner ecstasy, which of course I was.

"So, have you been doing any thinking lately?"

Mike just stared at me with his mouth slightly open and a look of envy in his eyes for what seemed like a long time before letting out a big sigh, and quietly uttering but one word.

"Deal."

"Great, I'll give my friend a call. Enjoy your game, if you think you can keep your mind on it."

I slinked out of the room with Mike's gaze firmly fixed on me. With a phone call, things were set up with Crystal, and then I returned to my room to reluctantly change out of my dress and remove the makeup. I then sat on my bed and reflected on my victory over my brother, feeling a little smug about my getting the better of him for once. It had been some battle of wits, and the only thing that was left, was for the both of us to wait for the appointed hour, if either of us could.

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Well...

Andrea Lena's picture

...slap a wig on my head and call me Kenny Mattel tm. Excellent start to a very interesting story, and from a fairly neglected perspective. Mike is teetering on virtual heels and is already top heavy with an imaginary bosom. He keeps denying it but his question about her 'really meaning it' regarding her dress seems to be pointed decidedly in a direction he claims he doesn't want to go. I can't wait for the next chapter...oh wait...I have no choice. But I certainly can say that I'll be somewhat anxious until your next installment. Thank you for a very well written first addition to the library here(I refuse to believe this is a first effort!).

P.S. I suppose it's fairly safe to assume that I'm not the only one to dress my sister's Ken in Barbie's strapless gold sequined cocktail dress?

  

To be alive is to be vulnerable. Madeleine L'Engle
Love, Andrea Lena

Thank you,

'for a great start to your story.Well done and most enjoyable,
bringing back memories of a time long past.Looking forward
to your continuation.

ALISON

Quite a delight. You've got

Quite a delight. You've got the pacing down very well. It seems Mike is a little over the top with his negative reactions sometimes, but I suppose that he's constantly waiting for the other shoe to drop from his sister. That would make anyone nervous and unpredictable. It's difficult to break through society's taboos so quickly.

Oh, welcome by the way. I look forward to seeing much more from you!

~Lili

Write the story that you most desperately want to read.

Actually, I think Mike's

WillowD's picture

Actually, I think Mike's negative reactions are just perfect. He wants it badly but he's scared silly about this. Big sis understands this. She is doing her best to ease him past the scary parts.

I am wondering if and when Mike figures out that his is a in a dominant-submissive relationship with his sister. And that's it's the submissive that's in control. I wonder what he will do once he figures out that saying that one little word "No!", he will have her squirming like crazy trying to woo him into a yes.

Good one Zylux

Laura is winding him in so slowly but so very well.

Great story on cross dressing, with a different twist.

Very enjoyable, thanks Zylux.

Age is an issue of mind over matter.
If you don't mind, it doesn't matter!
(Mark Twain)

LoL
Rita

My Ken Doll Part 1 of 2

How many sisters have used their brother has a dress up doll like she is with her's?

    Stanman
May Your Light Forever Shine