Oh, Julie!

This is my first shot at writing, so I would appreciate any feedback and any tips. If I get a good enough response, I would love to make a follow up story. All of this is based off of a real life experience. A special thanks to ExperiencedStoryteller for the edits.

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My name is Carlos. I was never really a one to kiss and tell about my sexual experiences. But in this particular case, it was too good of a story not to tell. I often think back on this particular night that I had with my old friend over and over again. Till this day it still brings me to the edge. And it all started with me reconnecting with this particular friend a few years ago.

I remember the first time I reconnected with Julie as if it was yesterday. It had been nearly ten years since we had last laid eyes on each other. At that time we were both straggly little high school freshmen. And when I say straggly high school freshman I mean probably me more than her. I was a prototypical skinny little 15 year old who was still going through puberty, had a fist full of acne and had band as a high point. While Julie back then was part of the so-called "in" crowd, being a part of the student council, the yearbook staff and to top it all of... a cheerleader.

And being a cheerleader came with the usual good looks and cuteness that Julie definitely had. While she herself was still in the early stages of "growing up," she had already filled out nicely. Tall, thin, with pretty fair skin and long beautiful light brown hair. And those eyes, those light brown beautiful eyes. Even though they sat behind a pair of small thin framed glasses, I could still remember those eyes of hers as if she never even wore glasses.

Despite her looks, she was actually the kind of girl who didn't seem completely out of reach. And while I was fair to say there were "hotter" looking girls than her, she was definitely one of my of not biggest high school crushes. And unlike my many other high school crushes, she was a person that I was lucky enough to have formed a nice little friendship with. Julie was an easy girl to talk to, and me being in high school, that was a big thing to say. She didn't stick her nose up at anyone and she wasn't really into hanging out with the other cheerleaders and jocks. So for me that meant I had a chance.

I think that was the biggest factor for me actually getting enough courage at the end of our freshman year to actually ask her out. And to my surprise she didn't say no and actually said to give her a call as she wrote her number in my yearbook. Needless to say it was the highlight of my very awkward first year in high school.

As my luck would have it though, we unfortunately never went out on that date.

I remember finally getting the courage to call Julie. When I did, I was heartbroken after the call. She was moving. And not only was she just simply moving and going to another school, she was completely moving out of town all together. It would be the last time I would talk to her or see her again for a very long, long time.

Nearly 15 years had passed since we had last talked. So when we did finally meet up it all happened by chance, finding each other online through a mutual friend on Facebook no less. A friend of a friend of a friend happened to comment on someone's status which popped up on my page. Luckily for me I had happened to stumble across the comment and lo and behold, there was Julie, replying to the exact same comment. It took me a while to realize who it was, but when I clicked on her profile, her last name assured me it was the Julie I knew.

I didn't waste any time trying to contact her, in the least creepiest way possible of course. Once we started to finally talk online, strangely enough despite us living in different cities and having different lives for over a decade - we ended up on nearly identical paths.

During that time, we both ended up dating our college sweethearts that ended up becoming very long relationships. Julie would spend 6 years with the guy she met and eventually married. I spent 7 years with the girl I met and to whom I became engaged to. Of course, heartbreak would fall upon us both and after all those years, we both ended up getting dumped by the ones we thought we would be spending the rest of our lives with.

Our similar stories led to instant chemistry. Since we knew what each other had gone through and the pain we had to deal with, everything came so naturally easy between us despite the years apart. Our back and forth messaging flowed easily and we started to have fun talking to one another. And only after a few days of messaging each other online and then finally exchanging numbers to text one another, we finally decided to meet up for dinner.

Even though it wasn't specifically specified as one, this was the first date that either of us had since our respective breakups. So I made sure I went all out on my end. At this point of my life, I like to consider myself a decent looking guy at best. I'm not a model by any stretch of the imagination, and I don't have a perfectly ripped body but I always felt that I was a handsome guy with an average sized body standing at 5'9 and just under 200 pounds. I definitely wasn't the scrawny little freshman that I was back in the day.

So that night I had dressed up in my nicest grey slacks and a buttoned up deep purple shirt that matched up well with my tanned brown skin. And before I left, I slicked my medium length dark brown hair back, combed and parted it slightly to the side and felt confident I was looking my best. I made sure I was in top shape from the bottom up. My only concern was going to the restaurant looking too overdressed.

I didn't know leaving my house with that mentality that I would arrive at the restaurant feeling completely underdressed when I finally laid my eyes on Julie.

As I waited for her outside and as she stepped out of the car, the first thing I saw were Julie's legs peeking out from under the door. I'm not kidding that they came out in slow motion looking as if they were coming out straight from a commercial. Her gorgeous legs were perfectly golden tanned, clean shaven and unblemished. With the three inch shiny black heels that she had on holding her up only accented their beauty.

When the car door finally swung closed, Julie stepped out wearing an outfit that nearly made my jaw drop. There she was walking towards me in her full glory. The woman was no longer that thin lanky girl I use to know. Now she was a full on hottie that had grown into her body quite well. At first glance you could tell she at least casually worked out, but even then, regardless if she did or not, her body was in perfect shape. She wasn't too skinny and definitely not big, she was a perfect in between size as a woman who had curves on her in all the right places.

And she didn't hide it. It was a modest, very "date" like outfit to wear, but just the way it clinged onto Julie's body made it all that more sexy then it would have on anyone else. Moving up from her heels and her legs, she came at me wearing a short black pencil skirt that tightly hugged the soft curves of her round hips. Even though she was just slightly shorter than me, the trim fitting skirt in combination with those sexy stilettos she had on, made her seductive legs look as if they could stretch for miles.

Meanwhile up top, she wore a matching small black and white, sleeveless checkered blouse. The blouse looked to be a lacy type of fabric that sat on her perfectly delicate trimmed body that made the checks in the pattern of her blouse constantly flowing and changing shape, drawing constant glances off of me that I couldn't stop throughout the night. What was even more compelling than how well the blouse fit her was just how she was actually wearing it. There only had to be a few handful of buttons on that shirt and Julie merely had half of them buttoned up, where the top of the blouse was left open enough to see the top of her exposed chest. Not in a way where it was a gratuitous manner on her part where her breast were hanging out, but just in the smallest way that the shirt needed to be worn to give that extra edge to her outfit. But for me, oh it was more than enough to see the glorious cleavage she was showing, showcasing her biggest change from back in school when I knew her.

I remember first laying my eyes on her voluptuous cleavage vividly. As they poked out from underneath her blouse, I could tell how firm and inviting they looked. I could see the edges of a black lacy bra peeking out behind her shirt and remembered how silky smooth her skin emanating off her breast looked. Throughout the night, her cleavage became the object of my desire as I constantly caught myself glancing out of the corner of my eye, hoping to get more than just the sneak peek that she offered. I had to bite my lip in order to remind myself not to make my looks be so obvious - but I just couldn't help it, I wouldn't have been in the least surprised that she noticed where I was looking.

I wondered immediately how anyone, especially her ex, could have been so stupid as to let a beauty like her get away.

Despite how aggressively sexy she was looking, it all came back to the familiar face I remembered so well from high school. Of course I had seen recent pictures of her that were posted on her profile and what not. But seeing her in person and in this light was something completely and totally different. She still had some of the same features that I remembered from when we were kids. However, everything about her appearance was more mature and had the defining edge of the woman she had become. Her cheek bones had more of a definition and a cute little dimple had formed on her chin. Her eyelashes flared our like a blooming flower while her lips had become subtly more plumped only to be accentuated by the irresistible light red pinkish lipstick that she had on.

There were still carry overs from back in the day that had a twist. Like how just in high school, Julie's light brown eyes were still hidden behind glasses. This time around though, the black framed glasses she was wearing really stood out giving her that very sexy innocent look going. A look that I was easily a sucker for given my past with woman and glasses.

Her hair meanwhile was also just as long as it had been back then, falling down just past her shoulders. But unlike in the past when she usually had it tied up in a ponytail with cheerleader bows, was now fully let down showing off her wavy flowing silky hair. Also her once dark brown hair now had light highlights that gave her mane more body and depth.

Everything about her from her hair down to her heels took my breath away. It's hard to judge a book by its cover, and a woman by her appearance, but I could definitely tell this wasn't the same innocent Julie I had known years ago.

I should have been wary right away of what the future had in store for us. But I was too stunned, pleased, and enamored by the shape and look of this girl who had become a woman before me, to even care what kind of consequences might come. She looked up at me with a gleaming smile that I swear brightened everything up around her. She was just so incredibly sexy and beautiful. I figured that nerves would kick in immediately and that I would end up becoming a nervous wreck. But in fact, I was surprised how open we actually were with each other and how it felt like if we had never missed a beat. And that was before Julie surprised me with how fast she could knock back the two glassed of wine she ordered with dinner.

Everything was just coming so easily, especially the flirting between us. Throughout the night there was the usual compliments and the smiles. But then things started to progress where we each started to find an excuse to touch each other's hands or somehow find a way where our bodies lightly grazed on one another. Which then lead to crude sexual humorous past experiences which then became a full blown conversation of things we liked to do in bed and how high each of our sex drives were.

Julie definitely was a different type of woman than I wasn't accustomed to or had come across, but a woman that was definitely welcoming. There was something about her that was dangerously smooth and seductive in the way that she carried herself. I had never come across a woman like this who could push my buttons so well.

Needless to say, when we finally parted ways and I went home that night, she was the center of my fantasy as I laid in bed. I couldn't help but think about slowly taking off those clothes she had on and finding what she had on underneath. I kept thinking about how soft her lips looked and how ample her cleavage stood out to me. I imagined us going into my car and her slowly moving down my zipper to release my manhood. I couldn't remember the last time I came so hard from masturbating, but I must have cummed twice that night before I finally fell asleep.

---

As chances would have it, and to my delight, we continued to meet up every so often after that night. Then our "every so often" then became frequent, then frequent became constant and before either of us knew it, the days and months started to pass where we were seeing each other almost every weekend. We would go to movies, dinners, shows and get-togethers. It just became a constant thing with each hang-out being more tantalizing than the last.

We just had this undeniable chemistry that worked so well between us. As well as the huge amount of sexual tension that always formed so thick you could use a knife to cut through it. We started to get so emotionally intimate and close with one another that our flirting became second nature between us. We became so close that we each probably knew what position we liked the most and how to make each other orgasm without having even fucked each other.

But it was just nothing more than that - flirting.

Looking back at things the answer could have been more complicated, but for that time the answer was obvious; it was just the wrong time. Both of us were not really that far removed from our previous relationships. And while we mutually enjoyed each other's company and really enjoyed the flirting, neither of us really had the nerve to pull the trigger because we didn't want to be in another relationship so soon.

---

As time passed, Julie and I had rekindled our relationship for a little over a year and a half at this point. Everything was still also relatively the same, but I knew deep down inside, eventually the relationship we had built up was bound for some sort of shake-up sooner or later.

That change eventually fell to the sooner side when I got a random text from Julie one weekend. I remember I was casually watching TV and playing a game on my phone at the same time when a text bubble popped up from her simply stating: "You wanna go to Florida w/ me?"

I laughed as I read the text message figuring it was Julie being Julie. So I replied: "Yeah let's go LOL" and flipped the phone down as I got up.

I didn't realize how serious she was when I came back to my phone with another text waiting for me that said she had found a pair of roundtrip tickets for under $300.

My eyes were wide open as I stared at my phone for a few moments a little befuddled. I was just waiting for another text from her that would say LOL or something that would show she was joking around. But nothing like that came up, instead I got another text that simply stated: "So? What do u think?"

She was being serious.

In a matter of minutes, Julie called me and we were on the phone together for a few hours planning our sudden trip to Florida. She said that she just wanted to get away from her daily grind for a while and I was the first person she thought of going with. Plus she really wanted to go see her favorite football team play and she figured we'd enjoy going to watch the game together while we were out there. With me being a hardcore football fan, I didn't mind that icing on the cake one bit. But that's all it was - just icing. The real plus was her actually wanting to go out of town on a trip... with me!

A trip where we would be together 24/7 for three to four days and would possibly sleeping together in the same room. It was hard not to immediately think towards the possibilities that such a scenario would lead too. I smile at just the thought of what that all might be, but nevertheless after a few more hours of figuring things out and sending some back and forth text messages, we had already booked the flight, hotel and game tickets for the end of December.

The days and weeks that we had to wait to leave on the trip flew by. And never once during that time did it ever occur with me that rooming with this girl who I had feelings for and someone I had crazy fantasies about would ever be an issue. I thought it was just going to be all fun and games. In reality it just showed how naïve I actually was.

I was indeed right that we would be sharing a room together and it didn't really hit me how hard it would be until that first night we arrived. Immediately I had to bite my lip and do everything I could to keep my hands to myself the moment Julie casually began to undress and change with me just a few feet away. And it wasn't in the fashion of her pretending I wasn't there or in the way where she just naturally felt I was just a friend where she could just change next to me. No, in my honest opinion it was more of her purposefully showing herself off.

Not that I minded of course. Throughout all the times we had gone out with each other, I had never seen Julie in her natural state. It was something I had fantasized her doing on a weekly basis, but I couldn't really grasp the thought of her actually letting me see her in all of her glory. Yet, here she was, changing right in front of me with every single inch, every single curve in full display.

Even though Julie didn't go full frontal nudity on me while she changed, it was still a sight to behold. I didn't know exactly how I held myself back from drooling all over her during those moments. And even before we went to bed, I still couldn't pry my eyes away from her. The nights we were there, it was always the same little sleep outfit she wore that left little to my imagination.

The outfit was nothing special, her hair was always let down and loose while wearing a pair of green short shorts and a cotton yellow spaghetti string tank-top that matched the colors of the team she rooted for. But it was the way the clothes formed on her body that kept me awake. Then to top it all off, Julie didn't bother wearing a bra underneath her tank-top and with the AC on in the hotel room every night, her perky little nipples poked out from underneath the soft worn fabric. But the short itty bitty tiny shorts were especially my favorite as they were barely long enough to cover her cheeks as they hugged her roundly luscious ass. The shorts were on the level where if they could talk they would scream at me to take a quick spank of her behind.

That first night that we stayed together in the room was especially excruciating. After we had got situated and changed for bed, I couldn't stop thinking about how incredibly sexy she looked. I tossed and turned as I felt the growing frustration that was building up inside my own sleep shorts I had on. I just wanted to cum!

I knew that if I didn't take care of my growing problem that I would never fall asleep. After lying in bed for a few hours, I finally decided to get up and take care of the raging erection that was propping up the soft white sheet I had on top of me. But to my agony, I had to wait until Julie was soundly asleep. The first sound of her snoring softly in the darkness was my cue to get up and quickly tip-toe to the restroom.