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.
