Sometimes we realize it's too hard to let go of some memories. Leighton can't seem to let go of his past. His father can't seem to let go of his mother. Then there's Natalie...

I'd simply given up. This had to be the most boring class I'd ever sat through. One hour stood between me and saying goodbye to my sophomore year of high school all together. The computer in front of me sucked. It had basic capabilities, and the only fun thing about it was being able to get on the internet. They even stripped the games off of it that came with the operating system. So I handled my time the best I could, by emailing a few of my friends.

I can't believe I took an entire year on how to use office software. First off, I already knew how to use most of it from home experience. I just thought it would be an easy A, but there was nothing easy about sitting through an hour of it each day. It was during that hour everyday when my mind began to roam, and I got myself into a lot of trouble. I didn't get into trouble with my teacher, but rather with the new online friends I surrounded myself with.

Normally I would talk to friends overseas, as they wouldn't be in school the same time as me, and could send back emails pretty quickly. However, I managed to find a few perverts along the way. Perverts usually found it easy to get online at any time. They also had a radar of sorts, which led them to younger people that sparked their interests. Unfortunately, I had met quite a few perverts online. I kept them around though, as they were always fun to mess with. Since they were all online, I figured nothing bad would ever come of our sometimes odd conversations.

Nothing odd, special, or out of the ordinary, ever happened to me. While everyone around me got whatever they wanted, I pretty much got left on the wayside. My dad came from a wealthy family, and invested into various things, which made him even more wealthy. He never had to work again, and would usually take long trips out of town with his flavor of the month. This means I usually had to fend for myself, but a caretaker was never further than a phone call away.

Mother was his trophy wife, beautiful beyond all description. My father captured her early on in his life, and she could never pass up the wealth and vacations. She died suddenly in a boating accident; tragically swept out to sea in the Gulf of Mexico. Before she died, however, she managed to provide my father with a family of his own. After giving birth to two daughters, one year apart from each other, she finally had me four years later.

My dad never really got over my mother's death. Though many thought he moved on, he just filled the void with women, booze and exotic trips. Even before those changes happened with him, neither parent really stayed to play house that much. They were always on the move. This usually didn't leave much time for me or my sisters. As soon as we got old enough, we were taken care of by a nanny and a maid, and my parents were out the door for another vacation.

Carly, my oldest sister, happened to be a spoiled bitch who got everything. Whether she wanted new shoes, or a new boyfriend, she got it. Once she even wrecked dad's car, and got one of her own to make her feel better. By the time she reached the age of eighteen, she flew as fast as she could away from home. Not long after she got married to husband number one. They shared a nice three months of marriage before she moved on to another.

Julia, the middle child, happened to be down to earth. She never let our dad's wealth change her. When she hit the age of eighteen, she went to college on scholarships. Out of the entire family, she was the only one who wanted to make it on her own merit. That doesn't mean she didn't get things. My dad loved to give presents. He thought if we always had nice things, it would fill the void of him not being there. To Julia, nice things meant clothes.

Then there was me, Leighton. If I had to be honest, I would put myself on the scale right between the two. Sure, I was down to earth as much as rich kids could be, but I also had a firm knowledge that dad's money could bail me out of any situation. This fact proved to be a great asset, as nothing else about me could bail me out of anything. I just wasn't any good at getting myself out of sticky situations.

I also happened to be an easy target. By the start of my sophomore year in high school, I had settled into my five foot and seven inch frame, which would undoubtedly stay with me for the rest of my life. Even though I weighed what was considered the healthy weight of a boy that height, I still looked like a scrawny nerd. I would've been considered a nerd if it wasn't for my mom's side of the gene pool.

I inherited, from my mother, a gorgeous pair of rich brown eyes. She gave me her dark auburn hair, while my two sisters got my father's raven black hair. Along with both of my sisters, we all inherited my mother's lightly tanned Latino skin. I never had to tan in my life, but if I did, my skin looked even sexier, not to mention healthier. The best thing she gave me was my pretty boy looks; small, bell-shaped nose, pouty lips, thin eyebrows and a small chin.

There were, however, some things I regretted about my genes. Weight and height aside, I also had some other small features. By seventeen I wore a size seven shoe, and never got into anything bigger. I also had small hands. Worst of all, I had a small package; at least from what I read about online. Going near women scared the crap out of me, as I felt embarrassed by my size. So even with looks and all, I never had a steady girlfriend.

This all led indirectly to my troubles. Since I couldn't land a girl in everyday life, I turned to the internet. During the course of my freshman year, I had gotten very involved with several places to meet people online. Mostly I lurked in the chat rooms, or talked to random people on an instant messenger program. I met quite a few people on a picture sharing site, but most of it got so annoying to use, that I eventually canceled several of my accounts. The only site I kept a constant eye on, was an instant messenger and picture sharing site called Xconnect.

Since about October of that year, I had become increasingly involved with talking to a girl, as well as many other strange people, both by instant messaging and through email. We updated each other constantly with messages about everything. I opened up to her about how I felt about my body and all. She eventually got me to post pictures of myself. When she said I looked cute, my confidence shot through the roof. I posted more, and she posted a few of herself.

We eventually got to the point where we were like old friends, and she told me her real name was Natalie. On one particular boring night we ended up on the subject of cross-dressing during one of our crazed message exchanges. Natalie was watching some comedy show where one of the characters cross-dressed to fool another character. We joked a little more about it, and then she made a simple suggestion. It was a suggestion about something I had never considered.

Natalie knew I had older sisters. She also knew they had left tons of clothes behind when they moved out. After a bit of coaxing, and quite a bit more nudging, I made a deal with her. I told her if my sisters' things fit me, I would wear them and take pictures for her. She loved the arrangement, but bet me I wouldn't follow through. I had to prove her wrong, and boldly asked her for suggestions on an outfit.

Natalie made it clear I had to wear something undeniably feminine. She said it would be cheating otherwise. Other than that, she didn't have an preferences. She simply told me to wear whatever fit me. The requests seemed fair enough, and made it so I simply could not think of a good excuse to back out of it. Natalie even promised to make it worth my while if I went through with her little dare.

With an empty house, and a Friday night alone in front of me, I raided my sisters' rooms. There was very little chance anyone else would be in the house that night. Carly was way out west, and never came back to visit. Julia had started college, and only came home once a month at the most. Even if she thought about coming home that weekend, she wouldn't have. As she only came home when dad was there, which at the time he was in Europe somewhere.

So there I was, rummaging through my sisters' things, trying to find the best outfit to get Natalie's affections for the night. It felt like I was on a scavenger hunt. I promised to send her the photos before midnight, and in return she promised to send a topless photo of herself. This was more than enough motivation to keep to my end of the deal. I actually had the idea to wear something racy, as it might solicit more than a photo from Natalie.

That's where I ran into problems. I found most of Julia's clothes fit me better than Carly's clothes, but Carly had the raciest outfits of the two. Things did fit me, however, so there really wasn't any reason to go back on the dare. Once I had settled on what I needed for my outfit, I thought Natalie might get a kick out of me going all of the way with it. I went back into Carly's dresser and rummaged through her panties and bras. To my surprised, I found something even better.

In the back of one of the drawers, I found a red bodice, with black lacy trim along the top and bottom. It had silky, ribbon laces crisscrossing the front, and two thin straps to hold it up on the shoulders. When I pulled it from the drawer, I noticed six black garter straps fall and dangle around the bottom. This told me Carly had stockings somewhere to go with this.

It took a lot of searching, but I found her stockings. They were rolled up in the back of another drawer. I pulled them out and unrolled one of them. For some reason Carly had gone classic sexy with her stocking choices. They were seemed with reinforced toes, and two inches of lace at the top. The black stockings also happened to be silky smooth and light. I looked at my legs and had a sudden spark of inspiration.

Before I could change my mind, I had run into my sister's bathroom. After several minutes I came out showered, smelling like my sister's shampoo and body wash. I had also shaved everything. I initially thought of only shaving my legs, but once I started I kept going, until every hair below my eyebrows was gone. Even my arms were now hair free and silky smooth. For some reason I wanted to go all out with this, to impress Natalie in some way.

I shivered as I stood nude in the air-conditioned room that Carly once occupied. A little seed of doubt started to spread its roots in my head. For a moment I stood trembling, letting my nerves get the better of me. Then, with the image of Natalie's body in my mind, I forced myself to get dressed. Mentally I had made my sisters' clothing my only option to be warm. I stepped over to the small pile I had amassed on her bed. With my hands shaking, I picked up her panties.

The panties felt so sensual going up my legs, and when I tucked my already small penis into them, I instantly felt emasculated. Their frilly lace trim tickled my now hairless skin, and the sheer black material of the back panel made it feel like the panties were hardly there at all. When I looked in my sister's full length mirror, I noticed the French cut accentuated my round ass perfectly.

My ass was another thing I had inherited from my mother. She had an ass like Jennifer Lopez, only she wasn't famous for it. I stared at my ass for several more minutes, before I decided to continue dressing. My legs were begging for the stockings. So I eased myself onto the bed and took one of them in my hands. Carly's bed had so much padding on it, that when I sat down, my toes barely touched the wood floor.

I had seen so many girls get dressed around here, that I knew the routine of putting on hose and stockings. It didn't take me long at all to have both stockings rolled up my legs. Most of the time was spent on getting the seams straight in the back, but I eventually managed. I smoothed each one out, while trying to keep from sliding off of Carly's bed. The stockings felt incredible as they encased my legs with sheer delight.

I knew if I didn't hurry and finish dressing, I would arouse myself too much. Once I attempted to squelch that arousal, this little journey would be over. I figured if I could maintain composure, I could use Natalie's picture to aid me in my other endeavor. It was too bad I didn't think to get her to wear something sexy and do a strip tease. Perhaps if she saw me first, I could convince her to do a show. I picked up the bodice and slid from the bed.

The wood floor was cold under my feet. So I pranced around on my tiptoes as I slipped into the bodice. I rested my ass against the top of Carly's dresser for balance while I laced up the front of the sexy garment. While I laced, I amused myself with the fact I was still on my toes. I could imagine people seeing me would call me a prancing sissy, and it made me laugh at how silly this all was in reality.

For several minutes I fumbled with the garters. I took great care to line them up, and not damage Carly's stockings. There was a very slim chance she would come back for them, but I didn't want to be the one blamed for destroying them. I had just gotten the last garter snapped closed, when I heard a sound from my room. It was a sound I had gotten all too used to hearing.

After prancing across the wood floor of the hallway and my room, I slid into the chair in front of my laptop. There were two emails waiting for me, and a new message from Natalie. I clicked on the emails to find one was a note from my dad saying he'd made it to London on schedule, listing his room number and other contact information. The second email was informing me I had a new follower on Xconnect. Great! Not like the majority of them talked to me anyway. Lastly I checked Natalie's message.

"What's taking so long? I want to see before I go to sleep. Backing down?"

I quickly typed out a message to her. "Not hardly! I'm just making it special."

Another message from Natalie popped up instantly. "So your sister's clothes fit? Noting this for future…"

I typed out a response immediately. "Ha! Don't get used to this. One time only!"

"Can't wait… Don't forget the lipstick and heels!" Natalie responded.

Natalie's suggestion actually excited me. I rushed out of my room, switching to prancing on my toes again halfway down the hall. After rummaging through both of my sisters' shoes, I realized none of them would fit me. Julia wore a size six and a half, while Carly wore mostly sevens. I thought Carly's would fit me, but quickly realized a seven in boys' does not equal a seven in girls'. Having no shoes to complete the outfit, really saddened me for some reason.

Then I remembered we used to have one more woman in the house. A few quick moments of prancing later, and I found myself in the closet of the guest room. We had moved most of mom's things in there after she passed away. I really didn't understand why dad had kept it all of these years, but now I was glad he did. Most of my mom's shoes were eights and a tight squeeze, but I found a few eight-and-a-halves in another box that fit me perfectly.

My mother really liked shoes. She seemed to have three pairs for every occasion. I kept digging through the box, unsure if she had anything for this occasion. Then one pair in particular caught my eye. They were a simple pair of shiny red pumps with a five inch heel. After pulling them from the box, I placed them carefully on the floor. I slipped my nylon-covered feet into them, and stood shakily.

At my new height, I discovered one of my parents' little hidden secrets. On the shelf, now eyelevel with me, I found a box labeled "toys" across the side. Now any kid would think the box was full of fun things to play with while it's raining outside. I knew better. My parents couldn't hide how crazy they were about each other. Especially when we caught sounds of them showing their fondness for each other emanating from their bedroom.

I pulled the box down, and slid the lid off of it. Right on top was a box of breast inserts. Thinking I'd hit the jackpot, I didn't look at anything else. I yanked them out of their box. They were the nice ones, to give women one cup size bigger. I imagined my mother used them to change things up for my father. Then I shook the thought from my head as I took the inserts and slid them into the top of my bodice. One cup size bigger for me happened to be an A cup, but it had to impress Natalie.

I figured my additions were better than nothing, and took a few wobbly steps out into the hallway. After getting used to the heels as much as possible, I carefully walked back to Carly's old room. Once I reacquainted myself with my sisters' belongings, I gathered up the black miniskirt I had laid out on the bed. It barely covered the lace of my stocking tops once I had pulled it up to its place.

The waist of the skirt was six inches wide, and had two inch-wide belts sewn into it. I realized the belts had to be buckled for the skirt to close. Closing it this way also forced the skirt to be worn higher, around the natural waist. I pulled the skirt up and sucked in my gut a bit to get the belts buckled. The finished result of wearing the skirt gave my body an hourglass shape, but the tops of my stockings now showed completely.

I turned to face the mirror, and posed in my new racy outfit. At least I hoped it was racy enough by Natalie's standards. There really wasn't anything to judge that by, as she seemed pretty open-minded about sex; at least online. Thinking about her reminded me of the rest of her suggestion. Lipstick! I rushed over to Carly's vanity and searched around for a tube of lipstick. The only one I could find still decently intact, was a laser red.

It fit the outfit, so I popped the cap of it off and brought it to my lips. Again, having to sit and wait for three women in the house to apply makeup, I readily knew how lipstick was applied. I carefully spread on a coat of the waxy substance, and rocked my lips together. Then I grabbed a tissue from the box on her vanity, blotted, and applied a second coat. I saw some smoky gray eye shadow sitting on the vanity, and thought I might as well apply some of it too.

After walking back to my room, I gathered up my digital camera. As I checked the battery and settings on it, another message popped up. I ignored it for the time being, and set the timer on the camera. In a matter of minutes I had snapped off several shots. I downloaded them to my computer, and quickly picked out the best ones. What I ended up with were ten somewhat sexy, but completely ridiculous pictures. I looked at the message. It was from Natalie.

"Come on! I'm dying here!"

Part of me wanted to send the ten I took, but another part of me wanted to take better ones. I made my decision, and left the room without sending them. Several minutes later I found myself back in Carly's room. I found a place to put the camera where it could see the majority of her large room. Her room always made me a bit jealous, as it had about a third more space of my room. Not to mention she had her own bathroom, whereas I had to walk down the hall to use one.

I shook the jealousy from my head as I started to take picture after picture. The more pictures that I took, the sexier I wanted to make them. I actually began to try different poses, and tried posing for quality rather than quantity. From my room I could hear the sound of Natalie's persistent messaging. Each chime from my laptop sounded so distant. I tried to ignore it as I shifted into different personas. In a matter of minutes I went from sultry to playful, and then back to sexy.

Each picture I took turned me on more. After dumping the memory of the camera onto my laptop, I went back to take more. This time I pretended like Carly's room belonged to me. I posed on her large four-poster bed, wrapping my legs around one of the posts, and then I started holding her stuffed animals. By the end, I had lost the skirt and heels, and posed sitting on the edge of the bed with my toes barely touching the floor. Carly's entire room made me feel small and girly.

I filled up my camera's memory once more, and made my way back to my room. By then I had amassed quite a collection of pictures. Without editing them, I simply picked the best ones and made them ready to send. I messaged Natalie "Incoming!", and started posting picture after picture to my Xconnect account. It took me almost ten minutes to get them on there, but each time I posted one I found it quite arousing.

As I posted the last picture, I fell back in my chair. I relaxed a bit, ready to receive my reward from Natalie. Only there was no response from Natalie. I looked at the time on my desktop and it was just past eleven. I obviously took too long. She either went to sleep, or chickened out on her end of the deal. I sat for several minutes waiting for her to respond, but she never did.

I cycled back through the messages she sent me. Not one of them said she was logging off, but there were several that coaxed me to hurry. I stayed online to wait for her, but I finally gave up around midnight. For some reason I still had energy. For some reason I wanted to continue this little adventure. After gathering up my camera, along with an extra memory stick, I rushed off to Carly's old room again.

I had the urge to wear something sexier. Frantically I looked around for more things to wear, but then I remembered I'd disrupted my mother's things. I dumped my stuff onto Carly's bed, and nearly wiped out in the heels as I scurried to the guest room. As I got to the closet of the guest room, my entire attitude had changed. Instead of wanting to clean things up, I actually thought my mother might have some sexy things. She was once married to my dad after all.

Looking through a box labeled "Undergarments" I found a lacy black garter belt to switch with the bodice. I wanted to try out some bras, but didn't want to take off the stockings. They felt incredible on my legs, and made me feel sexy. I picked through my mom's shoe collection, and rushed back to Carly's room with several pairs in my arms. Dumping the shoes on the floor, I rushed to Carly's closet.

Carly had the sexiest outfits, while Julia dressed more conservatively. The only problem seemed to be with fit. Julia's clothes fit me better. Julia and I were almost the same size, while Carly happened to be a little thinner. Maybe if I lost a little weight, I could wear both. I thought about this as I perused Carly's clothing. My mind kept bringing up the question of why I would want to fit better into these clothes, but I kept brushing the thought aside.

After dragging out a pretty heather gray dress, I laid it on the bed and tiptoed over to the dresser. The bodice was halfway off of my body by the time I opened her bra drawer. Inside the drawer, I found a bra which closely matched the panties I had on. The top half of both cups were black sheer material, while the rest of the bra was jet black with lacy trim outlining the sheer top.

I removed the bodice, and exchanged it for the bra. After quite a bit of adjustment, the bra fit snugly against my body. I placed my mom's inserts in the cups, and instantly had small perky breasts. All of the excitement gave me a burst of energy. Fixing the stockings to my newly acquired garter belt didn't even seem to slow me down. A few minutes after finishing with that, I was zipping up the gray dress.

I looked at myself in the mirror. The dress had a plunging scoop neck, and some of the lace and sheer material from my bra could be seen peaking out. It fit pretty snug to my body, but the material of the dress was soft and stretchy. The bottom hem of the dress barely covered the tops of my stockings, and there were cleverly cut holes, one on each side, that showed skin from the bottom of my rib cage down to my waist.

I started to wonder why dad would even let Carly go out in something like this. Then I realized dad was hardly around. Mom hadn't even been around to see Carly through high school. She probably would've applauded Carly though for demonstrating her femininity. Dad, on the other hand, would've cringed at his little girl going out with some guy dressed like this. I laughed when I wondered what he would think of me going out in the same dress.

After a few more minutes of demonstrating to myself how sexy I was in the mirror, I found a pair of knee-high boots in the pile from my mom's old things. I fell in love with how amazing they felt as I pulled them on. They were sexy boots, with tapered four inch heels and slightly pointed toes. I still had to get used to walking in them. What was I saying? I didn't have to get used to anything. This was for fun.

I looked amazing in the mirror. Before long I was back in the swing of things. I bumped Carly's clock radio onto a rock station and went back to recording my night of fun. My camera got a good workout that night. I really hadn't used it that much. Secretly, I had this plan of traveling the country and taking pictures with it. I was still too young for that, but damn if I didn't get another use out of it. After several more pictures of me sprawled out everywhere, trying to look sexy, I headed to my room to dump the pictures onto my laptop.

There was still no response from Natalie. She must have passed out waiting at her computer for me. That poor girl probably had a long day. I had a long day too, and it was starting to catch up with me. As I returned to my sister's room, I slapped the radio off and tried my best to put her clothes back where they came from. I tidied up her bed, and slipped out of her gray dress. While I was sitting down to take my mother's boots off, my energy left me all of a sudden. I spent the night in Carly's bed, wearing nothing but her panties, bra and stockings.

I don't know why I woke up so early the next morning. Maybe it had something to do with the strange surroundings of Carly's bedroom. Whatever the reason happened to be, I was glad I did. Our maid, Stephanie, usually came around eight in the morning to check things over for the weekend. I still had a couple of hours to return everything back to normal before she arrived. Somehow I had to get motivated enough to get out of Carly's plush bed.

I slid one leg over the side, instantly becoming aroused by the feeling of my stocking-clad leg sliding over Carly's silky bedding. The other leg felt even more erotic, but I had little time as it was to explore these feelings any further. Eventually I rose to a wobbly stance. The wood floor felt like a frozen pond beneath me. I kept the undergarments on, but checked to make sure everything in Carly's room seemed normal.

Satisfied, I ran to check Julia's room. I hadn't disturbed much in there, but I had to make sure. Then I went to the guest room, stopping to get the shoes I had dumped in Carly's room. The guest room is where I spent the most time, making sure everything got placed neatly back in the boxes. I was reluctant to give up the false breasts, but soon found myself placing them back in the cleverly mislabeled box of toys. I made a mental note to check that box later; to see what other treasures she might have hidden away in there.

After double checking every room, I stopped by the bathroom to wash my makeup off. Then I stumbled to my room. The undergarments felt so good, I really wanted to wear them longer. I did take the bra off, finding that it really wasn't all that comfortable. The rest I covered up with some baggy sweatpants and some sneakers. I'd just pulled a shirt over my head when I heard our front door close.

"Mister James?"

I guess dad just had this thing about having hot women around him. He hired Stephanie almost immediately after her first visit. She had been out of high school for a year, and had absolutely no prospects. Somehow she got into being a maid with very little experience, but she did a fantastic job. Even running after my sisters and I, when we were younger, wasn't much of a challenge for her. She was probably the only candidate with the energy to do so.

I seriously doubted the girls were much difficulty for her, as they were starting middle school. How Stephanie ever dealt with me, however, was a question for the ages. I was an absolute monster when I was younger. Somehow she kept us all in line. She kept the house in line, and even my father at times. I even think she'd struck a workable friendship with my mom before she passed away. I could never really get over how hot Stephanie was though.

Stephanie had this amazing, curly dark brown hair, that never seemed to come down past her shoulders. I knew it was longer, but she always managed to keep it up somehow. Her hazel eyes were the kind that told you they'd take no bullshit, but at the same time invited you to try. She had a hard body too; the kind you'd want to see in a French maid's outfit on the weekend, but she'd never wear such things. In fact, you had to imagine as hard as you could just to picture what all she had under her traditional corporate maid attire.

"Mister James!?"

I suddenly realized it wasn't Stephanie at all calling out my name. It was in fact Miss Stevens, my teacher for the next ten minutes. I had been daydreaming again, lost in the mundane hell of another office class. Miss Stevens stood behind my monitor, holding out her hand for my assignment. I sat up and fumbled around for the sheet of paper. It was some lame busywork thing to make sure we showed up and stayed in school for the last day. As soon as I handed it over to her, she exchanged it for my report card.

"Enjoy your summer Leighton."

"You too Miss Stevens," I said, as I deleted the history on the internet browser and closed it.

"Class!" Miss Stevens said, as she turned away from me. "I want you to remain in your seats until the bell rings." She walked over to the next row of computers. "Just because it's the last day of school, doesn't mean you should neglect the rules."

I tried to clear my mind as I watched the clock tick away on the desktop. Natalie had sent me an email, and for some reason my mind went back to that night. We'd talked countless times since I sent those pictures, but it definitely changed the dynamic of our relationship. It opened both of us up to talking about different things; perhaps even stranger things. I thought at one time we had grown really close, but then she stopped talking to me all together.

That's why I found it strange to get an email from her now. It had been almost a month since I last heard from her. I figured things got weird and that was all she wrote. Instead, she wrote again. She wrote me an email asking me to talk to her this weekend. I really didn't think twice about the request, and planned on jumping online as soon as I got home. Still… it was pretty strange to hear from her again. I wondered if it would be like old times.

Sometimes we realize it's too hard to let go of some memories. Leighton can't seem to let go of his past. His father can't seem to let go of his mother. Then there's Natalie...

There seemed to be nothing to clear your mind better than a bus ride full of teenagers on the last day of school. I felt relieved, and a bit rejuvenated. My report card held mainly B's, with a C coming from biology, and the A from my computer class. If my father was around to be proud of me, he'd be especially proud. Unfortunately, he left earlier that day to catch a flight to Canada. I actually wished I was old enough to force him to take me along.

The most irritating thing of all, was that I couldn't even have my own adventure. I had to basically hold down the fort, while my dad spent nearly the whole summer away. This left me alone in the house, but I still would have checkups from my father; and of course the maid. Stephanie really wasn't bad company, but she had recently turned thirty and had reached that point where she was like a mother to me.

Granted Stephanie was still impressively attractive for her age. I bet she could still work the high heels if she wanted to, but I never saw her in anything that wasn't practical. She did have a job to do after all. I figured flats were a lot easier to do housecleaning in than pumps. Still, it was fun to think about her clicking around the house in court shoes. That only got me thinking about what kind of maid uniform I'd really like to see her in.

"You coming to Jake's party tomorrow night?"

I turned to face the culprit who had grabbed my arm as I walked down the aisle of the bus. My eyes met the sparkling blue eyes of Veronica Garret. She had not said as much as a paragraph to me since grade school. Now she was asking if I wanted to go to Jake's party. Jake happened to be one of the most popular seniors at our school; or at least he was up until he graduated this year. Veronica smiled at me, anxiously waiting for a reply.

"I… I'm not sure," I said. "I have to see what's going on."

"Oh," Veronica said. "Well just stop by if you want. It's supposed to be wild."

"I'll see," I said, as I backed down the aisle.

"Well see you there I hope."

Veronica and I exchanged smiles before I turned to face the front of the bus. A few more steps and I was free. As the doors of the bus closed behind me, I hurried down the somewhat long driveway of my dad's estate. My mind quickly pushed Veronica's invite to the back as I thought about Natalie again. For many reasons I enjoyed her company online more than I did with people from school.

"Mister James?" Stephanie's voice echoed through the empty house. "Is that you?"

"Yeah," I said, as I shut the front door. "I keep telling you to call me Leighton."

"I haven't called you that since you were ten," Stephanie said, as she came around the corner from our living room.

"You're here kind of late," I said. "Is everything okay?"

"Everything's fine," Stephanie said. "I've stayed on a bit longer to make sure you were set for the weekend." She held up her hand as she turned around. "Your father left a list of some things for you. Mostly rules, but he asked me to go through them with you."

Stephanie walked away, waving me to follow. My eyes drifted down to take in her shapely legs. Even with that bland uniform covering her from elbows to knees, she still left a little bit of eye candy showing. The uniform itself fit tight enough to show off her assets, but I liked bare skin. Her legs, like everything else about her, were tight and toned. I managed to look up before she caught me.

"He wanted to tell you no parties, no girls, and nothing that will blow up the house," Stephanie said.

"Oh come on," I said. "He does the same list every time he goes away." I slumped into one of the dining room chairs. "Like I'm going to have some wild all girl party where we make our own pipe bombs."

Stephanie giggled. She actually giggled; like a schoolgirl. I watched her for a moment as she collected herself. Then she put the note down on the table. She sat down in the chair next to me, innocently crossing one leg over the other. Her closeness made me a bit uncomfortable, but yet she drew even closer. Finally she folded her hands in her lap and looked me over.

"I'm sure you'll keep out of trouble." Her lips rose to a pleasant smile. "I just wouldn't be doing my job if I didn't read your father's rules. You can read the rest later."

"You do a great job here," I said. "I just think my dad doesn't realize how often he does this sometimes. I mean… he's never here, but he feels he has to lay down the rules." I sat back as a sigh escaped me. "It's kind of funny… laying down the law of his house when he's never in it."

"Do you miss him being around?" Stephanie asked.

"I just don't get why he had a family if he's always flying somewhere to get away from us."

"I don't think he's trying to get away from you," Stephanie said. "I think he just can't find another way to express…" She held her head down.

"You mean he feels closer to mom this way?"

"Yes," Stephanie said. "I've been working for your family for so long, I feel like I'm part of it. I think I miss your mother as much as I'd miss my own relatives."

"I… just feel alone in my own house," I said.

"Well I'm here if you need to talk," Stephanie said.

"I'm able to handle it," I said. "I just wish my dad was able to handle his own issues."

"Maybe in time he will," Stephanie said. "I hate to bring this up…"

"More rules?"

"No," Stephanie said, smiling. "The real reason I stayed a bit later today, is to tell you that I'll be out of town until Tuesday."

"Oh… that's fine," I said. "I think I can manage."

"Well just incase," Stephanie said, quickly rising to her feet. "I made sure you're set with anything you'll need until then. There are some meals for you, labeled and all." She pushed her chair in and started to tidy up a bit. "If you have an emergency at all, you know how to reach me. I'll be out of town, but I can have someone from the agency check on you."

"Don't worry about me. I haven't had an emergency yet," I said. "Mind if I ask where you'll be?"

"Not at all," Stephanie said. "I'm taking some personal days to be with my mother. She lives in Oregon, so I'm flying out there tonight."

"You don't see her that often?"

"Well normally I don't take time off to be with her," Stephanie said. "But I haven't seen her in quite a while."

"Then I wish you all the best," I said, standing up from my chair.

"You just keep out of trouble mister," Stephanie said.

"I'll try."

I flashed her a grin, and she returned a knowing smile. Then she stepped forward and put her arms around me. I didn't know what to think at that point. She hadn't hugged me in years, and usually it was when I scraped my arm or something. I quickly put my arms around her, thinking it would be more awkward not to hug her back. And just as quickly as the hug began, it ceased. Stephanie retracted from me, and started to gather her things.

"You be good," Stephanie said. "You're not too old to be punished."

"I'll be fine," I said, laughing. "Have a safe flight."

"I'll see you later this week."

I held up my hand, waving to her as she backed out the door. As soon as the door shut I could finally taste my freedom. My dad's rules were a joke. I never had parties, and he'd never know if I had a girl over. I could have a threesome in his own bed and he wouldn't spend enough time in it to even notice. The only thing I had to worry about was Stephanie finding the aftermath. Only now, she too would be gone.

I rushed over to the door and locked it. After making sure Stephanie had made her way down the drive and out to the street, I grabbed my school bag and rushed up to my room. I couldn't wait to get back in touch with Natalie. All through my last class I had wondered what she could possibly want to talk to me about. Since I hadn't heard from her in a month, I wasn't sure what all she had been up to. As I booted my laptop up, for some reason my mind took me back to that night I sent her those pictures of myself dressed as a girl.

I had been in such a hurry to send the pictures, yet I had taken all of the time in the world to send them. As I suspected, Natalie had fallen asleep at her computer. She didn't get the pictures until she woke up several hours later. In the meantime, I had bombarded Xconnect with my pictures, sending all of the ones I found favorable. The last pictures I took were of my legs, with some close-ups of my mother's shoes. Then, after waiting for Natalie and getting no response, I finally passed out on my sister Carly's bed.

After I got rid of Stephanie the next morning, I couldn't wait to rush back to my laptop. I had dropped my sweatpants and t-shirt at my bedroom door. Wearing nothing but panties, garter belt and stockings, I sat in the chair at my desk; prepared to pleasure myself to the picture Natalie promised to send. I excitedly pulled up the Xconnect website, seeing my latest activity consisted of sending picture after picture of myself. I casually loaded my email.

To much surprise, I found my email box, and messages on Xconnect had exploded overnight. I had fifty new friends on Xconnect, yet no new messages from any of them. This struck me as odd, but I groggily read through the messages I did have. An enormous portion of them were from Natalie in private messages. I found it shocking that she had sent so many, as I figured she would simply comment on how funny the pictures were and be done with it. I started reading the messages, though they seemed strange with the backwards way in which the site posted them.

"Please get on soon!"

"I have to go to my dad's today. Maybe we can talk before I leave."

"I hope you wake up soon. Would like to talk to you."

"Hope you like them. I thought you earned more than one, but I don't think they're as sexy as yours."

I rubbed my eyes, making sure I was awake enough to figure out what the messages were saying. Something had sure gotten her excited. I seriously doubted it was me looking like an idiot.

"I kept my end of the deal, but my pics are in your email."

"You have GOT to send more! Maybe another outfit?"

"If you went girl, I would sooo go lesbian."

"The things I would do to you…"

"Did you shave your legs?"

"You even posed like a girl… so hot!"

"Can't believe you did it… You're so sexy!!"

I started to smile at Natalie's remarks as I continued to scroll through her messages. She obviously was shocked that I went through with it. Not only that, but she thought it was sexy and wanted to see more. I laughed, knowing that would be the one and only time I would ever do something so crazy. A small part of me was glad I did it, at least for her. It seemed she'd be willing to maybe do something crazy to see more though, which got my mind wandering as I continued to read.

"You actually make a cute girl."

"You are so hot though!"

"Miss Popularity!"

"I think you did. *wink*"

"Unless you wanted that?"

"Wanted what?" I asked myself. I scrolled down to the next message.

"OMG… You should have emailed those pics, or made a private folder! You posted them in your public section! Everyone following you can see them!"

As I read Natalie's first message, buried at the bottom, my heart instantly sank in my chest. I learned a hard truth that day, and it was a bit too late to erase what I'd done. I'd been stupid. I had put myself out there, thinking only about impressing one special person. Instead, I found out that all of my pictures could be seen by anyone following my Xconnect account. The perverts alone scared me, but even worse, someone I knew from school could be following my account without saying a word to me. My eyes fell on the few messages a stranger actually left on the site; a stranger going by Tfan128.

"You're the sexiest gurl I've ever seen. Would love to hook up."

"The pics were well worth the wait. You are smoking hot!"

"Been following you for months now. Glad I did. Pure gold!"

"I always thought you had potential."

I sat there at my laptop, and reread the messages over and over. The easiest thing to do would be to delete everything, block anyone I didn't know, and go hide in a hole. On the other hand, I had found a new side of me the night before. I kind of wanted to explore this path for a bit, and the nervous giddiness I felt now seemed exciting. The worst that could come of it is sixty or so total strangers had seen me dressed in female attire. It wasn't like I gave out extremely personal information about myself.

After a brief moment of reflection, I finally decided to act. I decided to leave the pictures up for awhile. If I felt differently by the end of the weekend, I'd delete them. The next thing I did, was send a few messages of my own. I figured since Tfan128 actually took the time to comment, I would respond to them first. Nobody besides Natalie had talked to me, so I figured it wouldn't hurt to reach out to someone new. I started typing out a private message to my new fan.

"I'll have to think about hooking up with you. I'd like to get to know you better first. Maybe we can work something out in the future?"

I hit send before I could change my mind. To get my mind off of what I had done, I focused on Natalie's messages. She mentioned she sent the pictures of herself, so I opened up my email to see. Sure enough, there was an email from her with several attachments. A few clicks later and several fantastic pictures appeared on my screen. Natalie was always drop dead gorgeous, but now I knew she had perfect breasts to boot.

In one picture, Natalie's hair cascaded down in wavy brown streams, and danced atop her breasts. If I had to guess, I would say they were a C cup. Her eyes were hazel, bright and excited. She had the cutest features, small ears, small nose, and her upper lip went up into a bow. Her small hands held a sign in them which read "To my CD friend. Thanks for the sexy pics. N" in purple letters.

I instantly fell in lust, and my hand moved to my crotch. Then I looked down to realize I still had panties on, and I had subconsciously crossed my legs like a woman. Instead of messing up anything I had on, I decided to wait. I studied Natalie's other pictures, burning her image into my mind. She was beautiful. Right as I got to a picture of her bare bottom and upper legs, an incoming private message startled me.

"I'd love to meet you. Still dressed sexy?"

It was Tfan128. For a moment I didn't want to answer them. Hooking up with some stranger from Xconnect wasn't top on my list of priorities. Still, I had put myself out there, and felt a little vulnerable at the moment. I don't know why, but I felt like talking to this person. Even if it was harmless flirting, it would at least be something different. I quickly typed out my response in a private message.

"The lingerie hasn't come off since last night. Will probably wear them a little longer this morning." I hit send.

Almost instantly another message popped up from Tfan128. "Are you alone? We could have a little fun."

Without thinking I typed out a response. "I'm all alone. What did you have in mind?" I figured this person wanted to engage in cyber sex, so I chased after the perverted thoughts going on in my head.

Another message popped up. "Excellent! I would like you to put on another outfit. Perhaps you have a pretty dress with flowers on it?"

Before I could even respond, an add request popped up for the instant messenger tied to my email account. It was Tfan128. The mouse shook in my right hand, while the fingers of my left hand tapped nervously on my stocking-clad thigh. I clicked to okay the add. After all, I did say I would hook up with the person if I got to know them. There's no better way to know someone than talking to them. An instant message box popped up on my screen.

"I'll wait while you change," Tfan128 typed.

I looked at his line of text for a moment. This guy actually had the audacity to think I would put on an outfit just because he asked me to. I started to type out a rude response to him, but then for some reason I revised my tone. "I don't think I am going to dress anymore actually. It was a one time thing I did for a friend. Not like I do it all the time."

"Perhaps," Tfan128 typed. "We'll see. In the meantime, I would like you to put on a nice floral sundress, nude hose, clean undergarments and fix your makeup."

"I don't know…" I typed. "We just met. I don't really feel comfortable with it."

Tfan128 typed out his next message. "Why not live a little this weekend? Just get dolled up, put on what I requested, and we can start having some fun."

I slowly typed out another question. "Are you a guy or a girl?"

"Panties, bra, hose, dress, shoes and makeup," Tfan128 typed. "I'll give you an hour."

I sat there stunned. Whoever this was, they were beyond persistent. In fact, they were downright domineering, and wouldn't take no for an answer. For a moment I sat and stared at the unrevealing cryptic messages. I couldn't even tell what sex they were. In a last ditch effort I tried to persuade them from their obsession with my crossdressing.

"Maybe if I knew you better," I typed. "How about we just chat for now?"

"Perhaps I'm not making myself clear," Tfan128 typed. "This is not a suggestion, nor a negotiation. For each minute you're late, I'll select one picture to send to your father's email address."

I called his bluff by claiming he didn't even have my dad's email address. He responded by reciting all of the addresses on my email list. Then he went further by typing out our home address and the addresses to where my sisters were currently living. If that wasn't enough, he listed all of our telephone numbers, and claimed to know where Natalie lived.

"How did you know all of that?" I hastily typed to my newfound stalker.

"I suggest you embark upon this journey with an open mind Leighton," Tfan128 typed. "I know an awful lot about you. For now I'll even let you keep your little online girlfriend, but keep testing me and I'll make sure you get rid of her as well."

"Why are you doing this to me?"

"My motives are moot," Tfan128 typed. "I'll provide further instructions when you show proof you have dressed accordingly. From now on I would like you to post all pictures I request publicly on Xconnect."

For a short moment I stared at the screen of my laptop. I really had no options. If I didn't appease this person, everything I did last night as a joke would become a very serious issue for me. I clicked out of everything, hoping it would make this guy go away. He had all of that information though. I stood from the chair and solemnly walked across my room. This person left me very little choice.

A perverted stalker wasn't the first person I wanted to talk to that day. I had hoped Natalie would log back on. By now we could be talking about something far removed from my little adventure last night. Instead, I had responded to a stupid message I shouldn't have bothered with. That's when I realized it didn't matter. This person would find some way to get to me anyhow, or just flat out send everything out to my friends and family.

Eventually I stumbled into Carly's room again. I found myself standing in front of her mirror, looking myself over. Still dressed in her undergarments, I remembered Carly had mostly sex appeal clothing. I'd have to work with what my other sister, Julia, had in her room. Julia was the sensible one. I had been quite sensible myself, until last night. Now I was paying for the craziest thing I'd ever done.

I had already been told what to wear, so there weren't many decisions to make. The one major decision happened to be the lingerie. I sifted through Julia's dresser and settled on a simple, yet elegant, matching set of white lacy panties and bra. She also had a few pairs of nude pantyhose, which I borrowed one pair for my outfit. The stalker gave me an hour, so I decided to grab a quick shower before changing.

The shower did nothing to relieve tension or relax my nerves. I still felt locked into doing an objective for some stranger. The dare for Natalie felt like a game, more fun and carefree. This, on the other hand, felt threatening. I felt violated even though nothing physical had happened to me; at least not yet. As I slipped my sister's undergarments on, I wished upon hope that this wouldn't turn ugly.

As the pantyhose rose up my smooth legs, I started to get aroused again. I had no time to even think about relieving myself. This would probably come down to the wire, and I didn't want to be late. I still had to deal with makeup. It needed to be fresh, and I needed to make it look appealing. Maybe I'd get bonus points from my stalker for looking nice. The good thing was, I didn't have to shave at least for another day. I didn't have much of a beard to speak of, and it grew slower than molasses.

Moments later I found myself sitting at Julia's vanity. I spent a good fifteen minutes perfecting a subtle look, and I really do mean subtle. There was a lot to be said for growing up around women. You just picked up certain skills you never knew you had. One of them happened to be the concept of "less is more" when it came to makeup. It would probably take years to learn how to do this as quickly as my sisters did it, but with enough care I could manage to make it presentable today.

Light blush, a little light blue eye shadow, coral lipstick and some powder was all it took to get me somewhat feminine looking. The only difference I had with my sisters was the fact it took me so long. I needed to pass desperately though. The person I was doing this for probably didn't appreciate many mistakes. If I slipped up once, my life could flip upside down on me. I took a moment to dry my hair and brush it out into something that resembled a female's style.

Then I invaded Julia's closet. Most of her clothes were pastels, usually without pattern, and almost all were girly. She thankfully had a few patterned dresses, and I let out the biggest sigh of relief when I found my objective. Julia had a beautiful white dress with a massive floral pattern. I think they splashed every color known to man onto that dress. Nobody in their right mind would argue that it wasn't the perfect dress for this stalker's demands.

I slipped the floral dress on, and zipped up the side. After a bit of adjustment, I went over to Julia's mirror. The dress fit perfectly too. Even with a slight taper, it hugged me in all the right places. The pretty sweetheart neckline and two inch shoulder straps hid my bra perfectly. While the hem of the dress came down low enough to be modest. It even swished a bit against my pantyhose when I moved.

I looked at the clock, and realized I had just enough time to find some shoes and take a few pictures. A few would have to do for this person. If they wanted more, I could take more later. Right now I had a deadline to meet. With one final glance at myself in my sister's mirror, I rushed off to the guest room. My mother's shoes would be the only ones that fit me, and it wasn't worth my time to try my sister's shoes out.

I took a moment to catch my breath when I hit the guest room closet. In a matter of seconds I had yanked out the box full of size eight-and-a-half shoes. Black wouldn't do for this outfit. White just seemed a bit mundane. I tossed aside the pair of red shoes I had tried the night before. My stalker would probably think I was implying sex with them. That's the last thing I wanted to worry about. Then there was pink, which would've implied weakness; another thing I wished not to show this person.

Finally, after what seemed like hours of digging, I found the perfect pair in the bottom of the box. They weren't black, white, red, or pink. They weren't some oddball glittery pair that would've clashed like the titans. They were true blue pumps, with four inch tapered heels, and matched the blues in the dress perfectly. They had a wide strap to wrap around the ankle, with several holes to adjust size. Instantly I deemed these as my favorite shoes. I was so enamored with the shoes, that I nearly forgot to get the breast forms from my mother's "toy" box.

After fiddling around with the straps, I finally got the shoes situated on my feet. As soon as I found my balance, I hurried back to my room to take more pictures; stuffing my bra as I went. I posed as sexily as I could, like I was trying to seduce my stalker. When I had filled up one memory card on the camera, I slipped it into the card reader on my laptop. Quickly I picked out the best ones, and nervously opened my instant messenger.

My fingers shook as I typed out a message to my new stalker. "I've taken the pictures and am posting them now."

I hit the enter key to send my message, and then clicked over to Xconnect. With each picture I posted, I saw my masculinity slowly start to fade. I wondered if this would be my new secret life, or even my new life period. Never did I think of being or want to be a girl, but now I was locked in to playing this fantasy out for someone I didn't even know. I just hoped this wouldn't last long, or turn out badly for me in the end.

"Excellent!" Tfan128's message popped up as I posted the last picture.

I quickly typed back to them. "Now will you tell me what you want, and why you're making me do this?"

Tfan128 took a moment to respond. I found myself hanging on every word they typed, unsure of where this was going. "You are a very pretty gurl. I think we're going to have a lot of fun together."

Now I was getting frustrated at how this jerk responded without responding. My fingers flew through my next message. "Who the fuck are you? What the fuck do you want? If you don't answer me, I'm calling the police. I don't care what you do, but I'll be sure to end it."

I stared at the instant messenger for several minutes. My stalker didn't reply. They left me waiting. My eyes were starting to glaze over with rage. Finally my stalker replied. The message blinked up on my screen and then they logged off.

"I can see you are a difficult one, but I know now that you have it within you to follow orders. Your final order for today is to remain dressed as you are. I will know if you disobey. We'll talk again tonight. In the meantime, I ask that you refrain from mentioning me to anyone. There could be dire consequences…"

I started to respond to them, but then I realized it was pointless. As I started to calm down, I realized it was probably someone messing with me. They probably got scared when I threatened to call the police, and ran off crying to their mommy. Still… why would they have all of that information about me, my sisters and even Natalie? How would they know if I kept this outfit on all day? This person was really checking into me, but for what purpose?

"You there?"

Natalie's message startled me. I had been so absorbed in my thoughts of the past, that I hadn't noticed my laptop had finished booting. My messenger service logged me in automatically, and Natalie had been waiting for me. It had been a month since I talked to her, and I didn't know where to begin. I thought of using a funny line on her, or somehow showing my wit, but I went with something more meaningful.

"Where have you been? I missed you!"