What If

*Teresa*

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."

We'd barely gotten the mysteries of all that out of the way when we reached my stop. Standing up in order to get off, Teresa did as well, even though her stop was still several stops away yet, though admittedly, it would almost be quicker for her to get home in getting off where I did. And yet...she did so, following me off. I had on some few occasions walked her home to her place after church, so I certainly had been to her place before, and once even invited inside for a brief visit. But never ever had Teresa been to my place.

"Wanted to see where you lived," she'd said answering my unasked question. So I took her inside, introduced her to my parents though they already knew "of her" in a way, though never formally meeting, or having been introduced to her before. After making a phone call to tell her mom she'd be home later than usual, she stuck around long enough for me to be given my "while were out for the evening" instructions...and then I walked her home. By the time we got to her place, her mother had already left, as she worked in the evenings as a waitress. Her dad worked in the evenings too, so it was a strange situation for her where she became the supervising adult over her younger brother and sister. Both of which usually disappeared out the door the moment her mom left for work, thus leaving the two of us pretty much alone together. Something that over time, we'd begin taking a lot of advantage of, but that was still a ways out yet. I mean after all, we weren't actually even dating...yet.

*First kiss*

I remember the conversation clearly, as though it were yesterday.

"So, is Dawn a good kisser?" She asked me point blank as I sat there on her couch. I had only planned on staying a minute or two, after walking her home, before heading back. After all, Dawn would be expecting a phone call later on that evening since we hadn't spent any time together after school.

"Yeah, I guess," I responded a little sheepishly, feeling slightly uncomfortable at the weird topic she'd chosen to discuss with me.

"Better than me?" She then asked.

For starters, I obviously had no idea. I'd never kissed Teresa, for real anyway. Only in my dreams. "How should I know? I've never kissed you," I responded back, not seeing the trap I'd just sprung on myself, but not minding that I had as things eventually turned out.

"Then maybe you'd better find out," she'd said looking into my eyes, expectantly. I guess if I'd been all that serious about Dawn, I would never have kissed her. But the moment she said that, I somehow knew, it wouldn't be the last time I would ever kiss her either. That kiss turned into another, and then another and another. And before you knew it, I'd been there almost two hours, just the two of us sitting there kissing and making out as it was called. Until "curfew" for her younger brother and sister brought them home again, forcing us to finally part company.

I never did call Dawn that night, too busy fantasizing, and masturbating like mad for one thing. But for another, I was also trying to come up with an easy way to break things off with Dawn. Like the old song says, "breaking up is hard to do," and Dawn knew immediately who was behind it all too. It didn't take a lot of investigating to find out as for the last few remaining weeks of school, Teresa and I spent most of it hand in hand, wandering the halls together, riding the bus home...and then spending a minimum of two hours every night tickling one another's tonsils with our tongues.

*Getting up to bat, feeling my first ever titty.*

Back then, just getting up to the plate was half the fun. Few were, and few did. And though I constantly struck out back then, never even getting to so called "first base", the fact was, I knew one day...I would. But there would also be only an occasional single even then, it would be a long time before I would ever score my first double, or make it to second base. Such where the times then perhaps. But I digress.

Still together by this time, and still dating, now in high school of course, and with me having just gotten my driver's license, and first car, it was time to celebrate. And it was also time to go out on our very first "official" un-chaperoned, date together. As such of course, we went to the drive-in movie. We'd certainly gone before, with friends who were driving, though none of us had done anything more than a whole lot of heavy kissing. Yeah, admittedly I had managed to graze one of her boobs here and there, and even once remembering she'd allowed me to rest the palm of my hand on her once, for longer than two seconds. After that, it became more of a challenge just to see if I could increase the duration of "officially" holding her breast, which came in nanoseconds of time to be perfectly honest about it. It took a long time before I finally hit the three second mark before she'd finally move my hand away from her breast. Or so it felt like anyway. But...that was an official halfway down to first base for me. At least I was now actually hitting the ball on occasion, even if I was still being thrown out before ever really reaching the base.

But things were about to change, and at a pace that I don't think either one of us expected or had planned on up until then. That change was brought about by the times to some degree, along with drastic changes taking place in Teresa's home life. Her parents were about to divorce for one thing, something that had been a long time in coming. It was also the age of Aquarius...free love, bra burning (though Teresa wasn't about to burn hers, let alone take it off yet), but that too would soon happen. But when it did happen, when things finally did change, it happened so fast, and in such a way, that in some respects, neither one of us was really prepared for it. I think part of that was because Teresa and I had both turned eighteen early on in our final year of high school.

For me, it was because of my mother way back when. For whatever reason, she hadn't started me in school when I was really young, when she should have, holding me back a year before doing so. In her way of thinking, she wanted to make sure I would be a bit older, a bit more used to the idea. Being an only child, looking back, I think she wasn't ready to give me up being home all the time. As for Teresa, hers was a matter of being right on the dividing line perhaps. Turning eighteen shortly after school started, and thus...the two of us already well ahead of most of the others when our senior year began. It had its perks...advantages, but it had its disadvantages as well. I was no longer governed by a curfew for one thing. As long as I kept my grades up, graduated...then I could pretty much come and go as I pleased. Something I certainly took a great deal of advantage of. As for Teresa, with her mother now divorced, trying to survive and raise three kids without a whole lot of support from her sometimes father, she was thrown into the role once more of playing mom, looking after her siblings while her mom worked most evenings. Though by this time of course, Teresa and I both had part-time jobs. As an "adult" one of the downsides of being eighteen...I had to find money to pay for my own dates, and gas for the car I drove. The days of having an allowance as it were, was over with. Needless to say, whenever we had time together outside of all that, we made it quality time. And that's when things just seemed to dramatically escalate all of a sudden.

*Making it to first, and then second base...standing up.*

Fridays were very special to us. For one thing, neither one of us had to work. For another, her mom did, which meant we'd pretty much have the place to ourselves, though I didn't dare show up until long after her mother had actually left. Her brother usually bolted out the door to head off and screw around with his friends the moment their mother left, which left us with Teresa's younger sister Sara, who could be a real pain in the ass at times. I think she hung around just to annoy us, knowing full well that we wanted some alone time. But she used that to her own advantage as well. Very often it took some sort of a bribe to get her to leave the two of us alone. Either with allowing her to watch some movie she shouldn't be, or having a friend over, or even going so far as to allow her to have her own boyfriend over, though she wasn't (or hopefully wasn't) doing what we had been.

I knew there was something about this particular evening too. It wasn't as though we had discussed it, or even talked about it...but it was in the air. When Teresa suggested that we go outside, out back, and sit on the old sofa as opposed to staying inside, I knew there was a lot going on here. That was indeed our "later in the evening" make out couch. Usually where we ended up for the last hour before I had to scoot home before her mother arrived. The fact we were going out there a whole lot earlier than normal spoke volumes. That, and the fact Teresa was wearing my favorite pull over sweater, the one I loved being able to caress and rub her tits through. And on occasion, once in a great while, actually being able to sneak a hand under for even more direct contact, though still while she was wearing a bra. Yeah, seriously...that's as far as I'd ever gotten with her. I'd still never actually touched them in the flesh, nor had I seen them either for that matter.

All that...was about to change.

We started out as we usually did, lots of kissing...only this time, it was still light out, no stars yet. And as such, I didn't dare jump to light speed and simply place my hand on one of her breasts. At least not until I couldn't really see what I was doing yet. That seemed to be at the time, one of the requirements or something. I tended to think it was because Teresa didn't want me seeing her "horny face," as I called it. Though I knew she got that, especially the way she'd squirm, even pant and moan a lot as I kneaded her soft breasts like freshly rolled dough. So when she lifted my hand, placing it right there on her breast, in the middle of daylight no less...I knew indeed this was going to be a very...very special evening. Especially when I discovered that double D Teresa, wasn't wearing a bra!

Now, like I said...on some few occasions, though even then not for as long as I would have liked, she'd permitted me to actually sneak my hand up inside her sweater or tee shirt, and actually fondle and caress her breasts that way. I had more easily felt her nipples harden through the material, enough so I could finger, and thumb them, teasing her...teasing them, certainly teasing the hell out of myself if you will, but never directly. The fact I was now touching her, in daylight...outside, with the threat of her little sister popping out on us at any given moment was one thing. But the fact I was also feeling her hard extended nipple, even with her (my) favorite sweater on was something else. For one thing, that fucker(s) was hard! Harder than I'd ever felt it, imagined it...and she seemed to be doing a lot more squirming and moaning too as I sat there rubbing it, rolling it, pulling on it, even if it was through the material of her sweater. In the meantime of course, I am also kissing her, everywhere that I could, every place I could find exposed flesh, I kissed before going back to her mouth again. And then I began to notice something. Each time I moved downwards, kissing that "V" of her neck, it seemed to be getting lower and lower with each pass that I made. Opening my eyes (finally) I saw that she had hooked two of her own fingers in that "V" of her sweater, pulling it down. I was actually looking at the upper swells of her full firm breasts, and suddenly kissing them too! More and more of them in fact. It became this weird, highly unusual game we were suddenly playing. I'd make the return trip back to her face, lips, and then start downwards again, watching her as she pulled down on this damn sweater of hers. More and more flesh suddenly revealed, and then saw...actually saw this difference in texture, coloration. And I knew without any doubt whatsoever, I was looking at the crescent moon of one of her dark colored areolas!