Staying Connected - Part 2

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 2

~by Taylor Ryan~

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!"

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