Nostalgic Ramblings

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How he got the one that got away.
9.1k words
4.68
60.1k
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Part 1 of the 2 part series

Updated 09/22/2022
Created 05/12/2004
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It's 2:13 p.m. on the East Coast, a murky gray day, just the kind I like. All my afternoon plans fell through, so I'm walking around my apartment naked, trying to solve a problem in my head. Also, I'm masturbating like the steam drill that killed John Henry. My roommate, who's also my sex partner, is out for the day, so I'm having fun by myself. She knows I write stuff for Literotica, and I'm sure she won't appreciate me mentioning her as my "sex partner" instead of my "girlfriend," but I don't appreciate her having a threesome last week with two girls from the restaurant where she works, so life continues to accumulate little moments of angst the way a beautiful beach retains the trash the tide brings in. Shit, that's downright poetic.

The problem du jour is what to do with "Chicago Hotel Adventure." By the time you read this, you'll probably already have seen part 4, but today, I'm really stumped on what to do with the last part of the story, and many of the Literoticans are wondering when the hell I'm going to post that last chapter. I'm as psyched as anyone that the story is so good, but I've really painted myself into a corner. If you've read parts 1 through 3, and you know anything at all about good storytelling, then you know I face a tough path toward a great ending. How could it top what's come before? It probably won't. In the end, George Lucas and I will have to settle with a stellar first three parts.

But that's not really what this submission is about. You see, I have an idea on how I can break through this minor mental barrier, and it all starts with brainstorming. Ideas create themselves, and you must stand by and allow it to happen. You just have to listen to your subconscious sometimes, you know? Right now, every time I try to think about "Chicago," my subconscious keeps turning my attention to an incident I remember from my senior year of high school. I figure I need to get the idea out of my head, and if it's as steamy as I remember it to be, and if I write it well, then I'll have my next post for the pervs back at Literotica. So, let's start typing.

I don't keep a journal, but if I did, it would probably read like my stories read -- random, unedited thoughts, strung together as the muse dictates. I know how to edit my work for clarity and a reduction in errors, but who gives a fuck. Why should my recollection of the memory be more pristine than the memory itself? And why is my dick so hard even though I'm typing these ridiculously profound elucidations? I turn myself on with my own pontification, I suppose.

Anyway, here's the story:

It was the spring of 1992, and I was getting ready to graduate from high school. My girlfriend and I had just broken up, and she was my first in every way. You may be surprised to learn it, if you've been paying any attention at all to my writings -- true stories of group sex, bi-sex, public sex, dom/sub sex, Rep/Dem sex... you name it. But at the tender age of 18, I'd only been with one girl. Hell, I'd only kissed three, one at the age of 14, the one before that at age 8. But my high school sweetheart was something special. We both started out naïve and ended up giving each other Ph.D.'s in sex ed. I highly recommend it... well, except for the part where you exclude anything from the relationship other than sex. That's definitely the reason why everything went so sour. What a thoughtless horndog I was.

I could try to explain why my relationship with that girl was so great, but unless you've been there, you just won't get it. What's so fun about fumbling around like an amateur for an entire year? Trust me, it just is. Grades went down the toilet, friendships got put on hold, but the orgasms were always stellar. And when we finally got past months and months of finger painting and snapped on our first condom, let me just say, even the awkwardness was sublime. For a time, we were true soulmates, whatever the fuck that means.

(There's another reason I can't tell you about my relationship with my first true love, and that's because we were both 16 and it was very physical. It's just not cool to talk about teenage sex on Literotica, which is to say, it's not legal. So do the Feds bust down my door once they learn I engaged in statutory rape? Was it mutual rape? I've read enough stories on this site to know rape stories aren't taboo, but that's not what this was at all. I've seen a website forum about masturbation where all the submitters are 13 and 14 year old girls, and while that makes me very uncomfortable, the hard cold truth is that I started jerking off at 14, and so did you and your sister and your dad and your best friend and your parole officer. I guess I'll just have to wait until I see this story posted to learn whether or not this parenthetical got edited out. I doubt that will happen. Wow, just look at how my philosophical introspections are turning me on once again. Put a social studies textbook in my hand and my libido goes through the roof.)

It was good and we liked it, but we were kids (18 by the end of it), and we didn't know what we wanted, and it ended in April. By the time May came, I realized too late that I wasn't going to spend the rest of my life with her, and that I probably better ace some finals in order to get my grade-point average back up. Then I caught bronchitis, which put me on the bench for track, which was another scholarship option that vaporized on me.

The biggest part was the regret. Not that I'd messed up on school, not even that my relationship had fallen apart. No, I regretted all the missed opportunities with OTHER girls. That's right, studs, you know what I mean. Things may be bleak with the girl you just dumped, but you are the creature you were meant to be, and that means you're always looking ahead to the next sexual encounter, whether your brain is a willing participant or not. Your frontal lobe may be screaming, "Don't think about other women! Can't you even remember ten minutes ago, when your heart was decimated? How can you want MORE of this?" But your dick doesn't care.

One of those girls for me was Melanie. (The name I've given her in this story is the ONLY part that isn't true.) Melanie was two years older than I, and I first met her in band. (Go on, laugh.) She played oboe and was good at it; I played trombone and hated it. Ours was a three-year school, so I was enjoying my first year (sophomore) as she was completing her last. One day, a mere week after starting high school, I got locked out of the school without my wallet and didn't have a way home (long story, who cares). This was before cell phones, and also, I was sort of an idiot. Well, Melanie drove by the front of the school and saw me sitting there. She offered to give me a ride, and I said yes.

That was the single moment at which I began to believe I might rise above my own junior high mediocrity and become what the ancient sophists referred to as "cool." Melanie was perfect in every way -- blonde, muscular from playing basketball, very nice to everyone she met, and approachable. I'd learn later that she was also very smart and quite giving, but during those first weeks, she was simply another unattainable goddess in a sea of high school goddesses. Never once during that car ride did I believe I had a chance with her, but the mere fact that she was aware of my existence was an affirmation that I didn't NOT exist. Perhaps the popular kids weren't just looking through me after all. It was a milestone.

In some ways, Melanie was responsible for me finding the courage to ask out my first girlfriend. (Let's call her Madame Ex.) Ex was my age, and we'd been friends for a long time. Only after my body pumped out the prerequisite amount of testosterone did I begin to see her as a sex object, and only after Melanie befriended me did I realize I could talk to Ex about things other than movies or the mall.

And so I began to look at Ex in a new way. In the meantime, Melanie was looking at me in a new way, and I had no idea. Why should I have? A senior lusting after a sophomore? By Jove, man, wouldst thou stand idly by whilst the planets crash 'nto the sun? These things go against the natural order! No no no, I was meant to be with Ex, plain and simple. She was pretty but not intimidatingly so, smart but not brilliant, foresightful but not ambitious. Also, she was brunette, and just between us, I was more into brunettes, and perhaps to this day I think of them as more obtainable than blondes, although the opposite is perhaps more true. See how convoluted the reasoning becomes? Just try having this discussion with yourself when you're sixteen!

Ex and I hooked up, and Melanie and I stayed very close friends. Melanie dated older boys, graduated from school, went to college, dated more boys, lost touch with me. Years passed, Ex and I imploded, and then May of '92 arrived bringing bronchitis in its wake.

The fateful day was a Thursday, a heavily clouded day just like today. I was home excused from school, listening to "The Soul Cages" by Sting. I had very poor taste in music then, don't be distracted by the fact. Daytime television sucked as much then as it does today, so I sat on my bed reading comics by the gray light of my window.

A knock on the door. I remember thinking it was probably the mailman; my parents would still be at work this early in the afternoon.

When I opened the door, there stood Melanie.

(Pause while I silently relive the moment...)

Pardon me, had to deal with a severe flashback there. I can tell you in varying degrees of detail everything that happened that day, but I can tell you with PRECISION the moment that Melanie showed up at my door. For one thing, she was the last person I expected, and she was also one of the people I'd most like to have seen at that moment. It's a powerful combination, and it leaves an impression. Every detail is burned in the mind -- the careless way her bright blonde hair was tied back behind her head, the healthy white glow of her skin, the fact she wasn't really wearing much makeup that afternoon. She had on a boy's burgundy knit golf shirt (was that something she bought for herself, or did she get it through more risqué endeavors? Hmm...) with tight plaid shorts and sneakers with those short socks that showed off her ankles. You don't see plaid shorts around much these days, but in the early 90's it was pretty prevalent. Besides, she could have worn an XXL leisure suit and I still would have wanted her.

I even remember the tiny red zit she had on her left temple. Now, you may not want to hear that Melanie had a pimple, because anytime YOU write a story for Literotica -- or I do, let's face it -- the girl has flawless skin like a porcelain vase or a bar of perfect soap or blah blah blah. To be fair, whenever I remember the incident, I usually remember Melanie without the pimple, so you'll have to do the same as you read my story. At the end of the day, most of you writers craft perfect women for your stories, but those of you who've actually HAD sex with a woman are familiar with all sorts of skin blemishes and love handles and other imperfections that you actually grow to love or admire or turn into a fetish. As for Melanie, well, that pimple is the single flaw I remember. Everything else was storybook good.

I wore denim shorts and a black t-shirt, which is what I still wear when I'm alone, if I wear anything; early habits die hard. My hair didn't look as good back in those days as it does now, and I remember worrying that it was out of place. What a little geek I was. But she probably didn't care about my hair, considering how my face lit up at the site of her, and hers at seeing me. She stepped forward and gave me a big hug, the kind you give when you see an old buddy after a long time. Innocent, to be sure, but very warm. We'd missed each other.

She asked why I wasn't at school, and I told her I'd had bronchitis. She made a sympathetic face, and I told her it was pretty much passed and I was just playing hookey at the end of the house arrest I'd been assigned. It didn't take much convincing for her to agree to stay.

At this point you're asking, where's the dialogue? You want to know exactly what she said, and what I said, and how we mugged and moaned and pleaded and yelped. Truth is, I remember a lot, but not everything, especially the words we said. And since I can't relay precisely what happened and how, to put down the words would sound hokey and sort of dishonest. When I write a fictional story, the dialogue is a very important component, but when I remember times like this, they're hardly important at all. The good stuff happened after the blabbing.

Melanie sat on my bed next to me and we listened to Sting. Melanie was more of a Smiths and Erasure kind of girl, and I really resent that she didn't try to expose me to better music back then. Today I'm all about the Hives and the B-52s and Radiohead (at the moment it's Neko Case blaring from six channels), but back then it was Duran Duran and Steve Winwood and whatever other shitty artist was on the radio that afternoon. But like I said, I learned from the mistake, no regrets. She told me how college was, and who she'd been dating, and how much she missed home. Then I told her about breaking up with Ex, and that was pretty much what the rest of the conversation was about.

Oh yeah, baby, that's right. Talkin' about ex-girlfriends with someone who has a crush on you. For those of you paying attention, you know that the good part is coming up, because this conversation is the classic segue to sex. Girls get jealous when you're dating them and you bring up past lovers, because they wonder if they can live up to what's come before, but BEFORE you start dating, ex-lovers are simply something for the girl to be curious about. She wants to know that you're experienced, and that you miss the physical relationship more than you miss the ex-girlfriend, and that you are ready to move on and start having more sex again as soon as possible.

In fact, the moment I knew something was stirring between me and Melanie was the moment she asked, "So, what kind of stuff did you guys do?" It sounds so simple, but it's really the first part of a very complex process. First, she has to ask the question just that way so she can hear you talk about having sex and being naked and getting raunchy, because the girl is horny and that's exactly the kind of thing that will get her even more worked up. Second, she can't say anything like, "Is that okay to ask? I didn't mean to pry. Oh, I'm so embarrassed. Did I embarrass you?" That's exactly what she WANTS to say, but she's trying to create a mood here, and bringing polite societal rules into the mix is counterproductive to the atmosphere she's trying to convey. Needless to say, while I was sitting there staring at Melanie's thighs, thinking how nice it would be to get something going with her, she was seducing ME. Good times, buddy, good times.

I was horny, too, so as soon as she asked, I said, "We did EVERYTHING." I had to say it quickly to confirm for her that no apology was necessary, that it was okay she asked. After that, she bounced on the bed a little and told me she wanted all the details. Over the year we spent together, during the time she was a senior, we had several similar conversations -- in tone, not in content. Not about music either, damn it. Mostly we talked about movies and books that we both liked, or people we knew, or things we'd done growing up. It's exciting to share details about your life with someone who "gets" you, and once you have the same kind of conversation about sex, well, what comes next is inevitable.

We spent about half-an-hour going back and forth on the sex subject, and while it started out pretty tame, it got graphic by the end. It's true that I'd learned a lot during my time with Ex, and there wasn't much we didn't do, but DOING sex is a hemisphere away from TALKING about sex, and I'm telling you, sitting there with Melanie was my first honest-to-golly sex talk, and it was fucking fantastic. I'm not even convinced she'd talked like that before -- I was probably her first as well. It's liberating, you know it? To capitalize on all the great skills you've developed regarding social conversation and idea articulation, to apply those skills to describing what you've done while naked with a member of the other gender, how it felt, what you'd like to try next. Sometimes the anticipation you develop in moments like those is better than even the hard reality of actual sex. No, I'm not a fag, shut up asshole, I'm just saying that I've had conversations with girls that were better than the sex that followed. Your friend knows what I mean, yeah him, the good looking guy.

Half-an-hour doesn't sound like a long time, but it's longer than it sounds. Positions... tender moments... things that were whispered, things moaned... favorite kisses... best orgasms... By the end of it, we were both exhausted and also both incredibly turned on. She had the most beautiful pale skin that burned a little red when she was hot, and she was damn hot at this point.

What happened next is really my favorite part of the story. We were still sitting on the bed, me with my back against the window sill, Melanie beside me, kind of nestled back against my shoulder and the wall. It sounds deliberate, but it didn't come across that way, because it was a twin bed and there are only so many ways you and a friend can share space on a twin bed. Yes, I know, she wanted to be closer, and I wanted to be closer, so it WAS deliberate, but you have to understand the game we were playing. Both of us had the same idea: If she (he) doesn't want to kiss me or touch me, but there might be a chance she (he) does, what position could I be in where either one is okay? How to abort the mission without consequences?

When that's the game, a lot of factors have to line up before you can move to the next level. For starters, the conversation has to peter out. Melanie was lying beside me like that, and one moment we were talking about sex and future lovers and maybe even school and schedules and shit. The next moment, the talking hit a lull. The proper thing to do during a lull, so we are told, is to regroup your thoughts and develop a new topic so the conversation can move forward. Fortunately, sometimes you end up with someone you like a lot and feel really comfortable with, and that lull is actually a nice time to just sit and enjoy each other's company in silence. You might not even realize how much you enjoy simply being with that person UNTIL the lull arrives and you have the opportunity to stay quiet and enjoy it.

Another important ingredient in the mix was Sting playing on the cassette deck. I can't remember exactly how the lull occurred or what the last thing said was, but I do remember that "The Soul Cages" (song not album) was playing when it hit. If you know the album, you'll recall that this song is a guitar-driven rocker, or what counts for one in Sting's world. Melanie and I sat pressed side-by-side as we listened to the song, and it was just something to do. (Later I remembered that this song was about fisherman losing their lives at sea and confronting Satan so they could bargain for their freedom, but I wasn't paying any attention to that shit at the time, thankfully. Sting, you are one disturbed Englishman.)

What next? I'll tell you what next. I took her hand in mine, that's what.

No ceremony, no words, not even a pang of doubt in my mind or gut. I just wanted to slip my hand in hers, and I did. It felt right... "proper" is the word. We'd both been wondering for an hour whether we were attracted to each other, fumbling around for words to figure it out, and one touch was all it took to understand what a thousand words couldn't illuminate. We weren't in love, we weren't really even friends in the way we had been, but there was a physical spark at work, and now we both knew it for certain.