Staying Connected - Part 1

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...

Staying Connected - Part 1

~by Taylor Ryan~

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.

If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
132 users have voted.

And please, remember to comment, too! Thanks. 
This story is 5925 words long.