What If

by Thesandman

Caution: This Sex Story contains strong sexual content, including Consensual, Reluctant, First, Oral Sex, Masturbation, Petting, Squirting, Voyeurism, .

Desc: Sex Story: This is a story about a lot of firsts, a lot of memories, emotions. It is about lust, desire, mistakes, regret. It's a story about life


This is a story about firsts. A whole bunch of them in fact looking back at them now. Everyone says they clearly remember the first time they ever made love with anyone. And I suppose that's true. But I clearly remember all the other first times as well, as though they were yesterday.

I met Teresa in the 5th grade. She would later become the girl I would date and eventually experience a fist full of firsts with. But that was years away yet. Right now, my female experiences were limited to gawking, acting silly, stupid, trying to impress a girl who wouldn't give me the time of day. Hell, what girl at that age, who was of the right mind would anyway? And to what point? The point was, there was just something about Teresa that told me, even at that age, we were somehow meant to be together. And then as it was perhaps expected, I chased ... and Teresa ran like hell. Funny how fate can step in and totally change things so unexpectedly. As the next few years passed by, Teresa and I found ourselves sharing classes, and then into Junior High, taking the same bus to school, likewise again having a couple of classes together. By now, she at least tolerated me, even smiled on occasion, enjoying my still somewhat stupid jokes and attempt to befriend her more than she was willing. All for naught of course, Teresa was still as elusive as the pot of gold at the end of the proverbial rainbow.

She wasn't as anyone might classically call a raving beauty, but she really was pretty. Of Spanish decent, she had an olive complexion, dark smoldering eyes to go along with her middle of the back length almost coal black hair. She wasn't tall ... if anything short, at just five feet, if that even. The fact she had a rather large chest for her size, (which by the way was admittedly one of the reasons I was attracted to her back in the 5th grade. She was about the only girl in our class that actually had boobs large enough to require wearing a real bra.) But try as I might, I made no better headway with her than I had early on, and so at last ... I finally quit trying. And fate had a hand in that as well, in the weirdest of ways.

Heading into the second year of Junior high school, the powers to be for whatever reason, changed school boundaries on everyone. With Teresa just living on the next street over from where I lived, they had chosen the very street that separated us as the border for sending us to different schools. Teresa remaining with the same school we'd both attended the previous year, and me ... off to a brand new school that had recently been built. When that happened, I had pretty much figured that it was meant to be, and that it was time to give up on my almost life-long endeavor to win her over. As such, I began looking elsewhere, and eventually had better luck with a girl I soon met, and began seeing as often as I could after school. Sure, I still saw Teresa on average of once a week as we attended the same church together, but beyond that, that was all. She'd even made a point of coming up to say hello to me first, something she had never done before. But like I said, by this time ... I'd given up on her, and having someone else who did seemingly enjoy my attention and affections, I suppose I was far more aloof around her than I had ever been before.

The chaser ... became the chase' e.

Dawn was my first ever "French Kiss," a cute petite little blond who was also a member of the girls junior cheerleading squad. She was in a sense quite a catch, and furthered my status in the rankings back then as 'lucky guys'. And though we hadn't done anything ... and I virtually mean anything, French kissing a girl was considered more or less a prelude to eventually going further with them. So as far as I was concerned, it was only a matter of time. Needless to say, the furtherest thing on my mind was Teresa. Though when I saw her again, so unexpectedly I might add, the timing couldn't have been any more perfect.

Dawn and I were milking our five minutes between classes to maximum degree. With both classes close to where we were standing, there was just enough time for a press against our respective lockers (also close to one another ironically) a quick (non tongue) kiss in this instance, and then a promise to see one another after school of course. We wouldn't have time to visit again until then as after this, our two remaining classes took us off in entirely opposite directions. And so it was with the warning bell that we had less than a minute to make it to class now, Dawn kissed me quickly once more, and then headed off to her class down the hall. The moment she broke away, I looked up past her as she ran off, and low and behold, there was Teresa walking towards me. Surprised to see her yes ... I nevertheless took a moment of secret delight as she had to have seen Dawn and I actually kissing there in the hallway. She continued to approach, even having a smile on her face as she looked at me. I stood however still dumbfounded at seeing her here, at this school ... my school.

"Cute girl," she said passing, still smiling and then walked right by me looking at obvious room numbers. In doing so, reminding me that I was going to be late for class myself if I didn't get a move on here. But still curious as hell as to why Teresa was now here at my school. When she stopped, looking at the teachers name on the door, and room number, and then entered the class, I almost fell over. She'd just entered into my classroom. Social studies and human nature class, of all classes to be having with her ... but obviously, I would be.

I couldn't help but wonder if fate wasn't once again intervening here for whatever reason. With Teresa being given a seat one up and across from me, I sat just behind her, occasionally given glances backwards from her as she caught my eye, once again smiling in a way I had never seen her smile at me before. I soon learned she had been transferred, even this late in the year with only a couple of months to go before school was out for the summer. An oddity as that wasn't a very common occurrence, not at all ... especially this late in the school year. But as it turned out, there were still adjustments being made. One of which was class size, and so the word had gone out on a volunteer basis, that if there were any students who were willing to transfer to the new school, even inside current boundaries, then arrangements would be made.

Teresa had been one of a small handful, who had volunteered to transfer, and now she was sitting in my class.

Role reversal

Though I continued to see and more or less date Dawn, Teresa and I likewise reacquainted ourselves, and basically renewed our friendship, more so in fact than it was before. But now, I didn't actively pursue her of course, not like I had done. Dawn was now a part of some of our conversations in fact, though I found it interesting that she herself wasn't seeing or dating anyone. Towards the end of that year, we found ourselves thrown together in a very unique way, though at the time I didn't foresee the future, or what would come out of it, because of it.

There was a TV program being aired at the time, called "The dating game." It was very popular, if not quite outrageous at the time for prime-time viewers. All of the drama and arts classes were involved in producing our own version of the Dating game for school assembly, and as luck would have it, I was to be one of a handful of so called "eligible" bachelors. What I didn't know until we were literally on stage, was that Teresa was the unknown, likewise eligible bachelorette. Needless to say, it didn't take long for either one of us to realize she was the one asking questions, and that I was one of three guys answering them. I even got most of the laughs as the game progressed, and it also seemed more than my fair share of the questions being asked too. I was fairly sure that Teresa would be picking me as her "date" as the game continued, which consisted of a cheap evening meal at a local hamburger joint as it turned out. But to my surprise, along with everyone else's as it later turned out, Teresa selected someone else. And though I think Dawn was quite relieved at the outcome, I was taken aback by the end result, along with a goodly number of classmates and friends. Everyone said we had this sort of real "chemistry" and why Teresa had picked someone else, remained an unsolved mystery. At least until the very next weekend.

We were back to sharing a bus ride home. And though I didn't always take the bus, most often walking Dawn home after school instead, it left me with a two mile walk home after doing that whenever I did that. On this particular night, I'd been tasked by my parents to "take the bus", as they were going to an office party that evening where my dad worked, and wanted me home before they left. Thus I found myself sharing a seat with Teresa on the way home, which is when she told me, "You know why I didn't pick you over Jerry?" She began. Although I was curious as to why, I didn't want to seem too anxious about it either.

"Haven't really thought about it," I told her. "But since you mention it, why didn't you? Everyone said afterwards that they thought for sure you were going to."

"And that's the reason I didn't," she said candidly. "Because I knew everyone there ... including your girlfriend, thought for sure I'd be picking you. I didn't want to cause problems for you because of it."

.... There is more of this story ...

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