I Wish She Hadn't Ch. 01

I wasn't going to argue with her, but I don't know why Madi thought that I was any different than she and Libby and Tommy were. We were all from "the wrong side of the tracks." The only difference was that in my family, it was made it clear to all of us kids that the only way to cross the tracks was to go to school -- that getting an education was the way out.

My mother insisted on it, and being the fifth of six children, things had pretty much been decided by the time I wandered onto the scene. Whether I liked it or not, I was going to school. Not that my mother was helping, mind you. We kids were on our own as far as money was concerned, but I guess, in retrospect, I'm glad those expectations existed. In that particular instance, I was better off not having a choice.

Still, that was a discussion for another time and another place, so rather than lecture her about all that, I let the matter drop. "I aim to please!" I said, smiling at her.

"I do, too!" She smiled back. She kissed me again, and then she suddenly reached for the damp washcloth at the foot of the bed and gently wiped the mess from my face. "There. Feel better?"

I shook my head childishly. It seemed like maybe Madi and I had reached some sort of détente on how our sexual relationship might proceed. That was good, but now her "mind-boggling orgasm" had me in the mood for something more. Besides, she'd made me promise that we'd have intercourse that night, and I was ready for something romantic now, some lovemaking, not just "mindboggling" sex. Ironically, we ended up have both.

"Do you still want me inside you?"

"Of course! Why, do you ask? Did you change your mind?"

"No, not at all! When you came, you got me excited all over again!"

"You don't look all that excited. Not like you were before", she said staring at my flaccid cock dangling between my legs. "I bet I can change that!"

"I bet you can, and I'm guessing you will!"

She smiled sort of devilishly, removed the damp thong that covered her sweltering pussy, dropped it to the floor, pushed me back into the middle of the bed, crawled between my legs, and then began to make love to me with her mouth. This time her purpose was different and so, too, was her technique.

Now, she took her time, and I followed her lead. It is interesting because I never told Madi of my desire for something more romantic, but once we started up again, something sort of magical and really natural took over. The pace of our lovemaking slowed; our kisses and touches became more languid and sensual. We'd both cum, so the urgency we'd each felt earlier seemed a thousand miles away.

Madi got things started by using her mouth and hands to kiss, caress, lick, and suck me back to life, but this time she didn't take me in her throat, and I was really glad about that. It didn't take very long before she had me rock hard again, and now I was ready to make love.

I gently grasped her about her shoulders, and pulled her up my body until she lay atop me, much like she'd done to me only minutes earlier. We kissed and caressed each other like that for few moments, and then with my legs between hers, I slowly rolled her over, so that we'd changed places and I was on top of her.

"I need to be inside you", I said kissing her sort of breathlessly. "Are you ready for me?"

"Yes, I want you." She spread her legs wide, and then wrapped them tightly about my hips.

I rose above her, hovering over her slender torso while I extended one hand to the mattress to support my weight, and with the other, I grasped myself around the base of my shaft and found her wet opening. Then, I slowly pushed myself into her, just the head for now, but as soon as my engorged glans slid past that narrow opening an inch or so inside her -- the same tight place that I'd discovered earlier with my fingers -- I popped through into uncharted territory -- that metaphorical, but literal Promised Land -- and now my slow, unhurried penetration unleashed a long, low coo, "Ooooohhhhh mmmmmyyyyy gggggoooooddddd! That feels so nice!"

I wanted our lovemaking to be gentle and passionate, so when Madi reached for my face with both of her hands and leaned in to kiss me, I froze with only my bulbous cockhead penetrating her. We held that kiss a long, long time, our tongues and lips playing together, like a string quartet, delicately swirling their way through a baroque canon -- slower, faster, then slower and faster again. But as nice as her tongue and lips felt on mine and as sensual as the feeling of her velvety pussy caressing my cockhead was, I really needed to go deeper.

So, I gently grasped first one and then the other of her hands in my own and then moving Madi's arms up and extending them above her head on the mattress with her palms facing upward so that our fingers were interlocked together, I supported my upper body on my outstretched arms and now our faces were only inches apart so that we could share sweet kisses and whisper romantic platitudes in each other's ears.

Then, I started moving... really slowly. Gradually, I lengthened my strokes, trying my best to gauge my advances by her vocal response to each penetrating thrust, "Ooohhh! Oooohhhh! Ooooohhhhh!" After a minute or two of progressively deeper plunges, my fully engorged shaft had disappeared from sight, and my pubic bone was making its first contact with hers, and it was that last thrust that educed a long, low, and inimitably sensual growl from Madi, "Ooooohhhhh, baby, you fill me up!"

Over the next few minutes, Madi became just incredibly effusive and over-the-top in her play-by-play of my lovemaking -- "I just love your cock, John", "oh lover, you are so fucking big inside me", "I love the way you fuck me, babe", "ooooohhhhh, deeper, John, deeper", and on and on.

On the surface, it seemed like it was the same kind of bullshit comments that two or three other women had used on me when we were in the sack together, and I had always regarded those as patently fake. Those women were always lying because they had one ulterior motive or another that they thought they could achieve with that kind of obsequious flattery and servile adulation. They were as transparent as they were dishonest.

But in Madi's case, it wasn't bullshit. I realize now, she meant every word of it. For reasons that I couldn't even begin to understand at the time, but began to appreciate years later, Madi Adams had elevated me to a pedestal that I had no right to occupy. I think it may have all stemmed from a freshman high school girl's infatuation with a senior boy that she somehow inexplicably found "dreamy."

The problem was that I just wasn't "dreamy", wasn't the handsome, star quarterback, the big man on campus, the studly hunk in a letter jacket overloaded with medals and patches. In fact, I hated those assholes, hated them and most of the other jerks from high school: the brainless conformists, the artless sycophants, the moronic jocks, the annoying Future Leaders of America, and, worst of all, the cruel fucks that teased and abused the younger, weaker kids, all the while having somehow convinced all of their parent, teachers, and coaches that they were upstanding, compassionate, pure, and chaste, when the truth was they were the absolute antithesis of all of that.

They were all hypocrites, as far as I was concerned, and to me high school was just the first of Dante's Circles of Hell, a fate to which we had all been condemned, but one which I endeavored to endure by ignoring it as much as humanly possible. It wasn't that I was alone in choosing to suffer my misfortune in such a way. I had my own group of friends. There were plenty of people that felt the way I felt, and, like me, they all just wanted to get out of hell as fast as they could.

But my cock was buried in Madi Adams' tight pussy at that very moment, and that was a heck of a lot closer to heaven than it was to hell. Once I entered her pearly gates, I wanted to spend the whole night there inside her, and as it turned out, I very nearly did!

But when I looked down at her beneath me, I could see the erotic pressure building inside her, and I realized that Madi was even closer to heaven than I was. The root of my stiff spike was pulling her slender, pink clithood to it on every deep thrust, and now even in the darkness of that stranger's bedroom, I could see her swollen, little bud emerging from its sleeve and bumping up against me. Madi's irregular breathing and involuntary grunts and groans portended an imminent explosion.

So I decided to build my speed. I was getting close myself, and I wanted to get us both to the place we longed to be. I started pushing even deeper, and once I was gaining maximum depth, I tried to grind myself against her, and when I did that, Madi responded by pulling her knees toward her chest, until I could move my outstretched arms behind the backs of her thighs, so that her legs were pointing straight to the ceiling and there was nothing to hinder the depth of my thrusting. Now my pace became frantic.

Soon, her non-verbal pants, grunts, and groans transitioned to obscene words and phrases, "Oh, I'm fucking close! Oh, one more! Just one more, baby! Oh, oohh, ooohhh, oooohhhh! Oh fuck, I'm cumming! I'm cumming! I'm cumming, baby! Oooooooooooooooooooohhhhhhhhhhhhhhhhhhhh!"

And then I could feel that pussy spasming again, closing tightly around my shaft and releasing, over and over, at least a dozen times. She kept screaming things, but she was so loud I couldn't really tell what she was saying, and her slender body, despite being pinned to the mattress by my own, was writhing and quaking beneath me.

And when I felt her already snug pussy begin to convulse around my inflamed head and engorged shaft, I, too, started to pass through those pearly gates, and the cum started rising out of my balls. "I'm gonna fucking cum! Fuck! I'm gonna...! Fuck! Fuck! Oh shit, I'm cumming!" I growled while a tortured grimace swept my ruddy face.

My climax had snuck up on me. I wasn't really ready for it. Madi's own orgasm had gotten me there faster than I expected. Had I been ready, I would have done what I usually did and pulled out, but I didn't have enough time to really think about that. In the moment, Madi's reminder from earlier that she was "on the pill" never really registered with me. Thankfully, she was, but, whether I should have or not, I kept thrusting away until I just let go, depositing eight or nine ropes of my goo deep inside Madi's frothy pussy.

When I was finally done shooting, I let go of her legs and just sort of collapsed on top of her. Pressed chest to chest together as we were, I could feel both of hearts pounding and our lungs heaving up and down. We were both gasping for air.

What had started as passionate, gentle lovemaking had morphed into something more urgent, physical, and aggressive. We were both just slightly overcome by the whole thing -- a little exhausted, but happily so. When our breathing normalized just a bit, we kissed again.

I was the first to speak. "Oh my god, Madi!" Then, I smiled and said more seriously, "Madi! That was amazing! Really fucking amazing!" She didn't say anything, but she was nodding her head up and down so enthusiastically and smiling so brightly that I'm certain that she felt exactly as I did.

We were back at it soon enough, and now we were foregoing the romantic stuff. Madi rode me backwards. Then, we spooned for a good long while, and finally I took her doggie style. Madi came in every one of those positions, and then after I had already made her cum from behind, she asked me if I would cum on her face again. She said the liked to watch me cum, said it turned her on a lot to see how much jizz I could spurt. The truth is -- and I'm convinced that nearly all guys think exactly this way -- the biggest turn-on for us is cumming on a woman's face. I think, whether we admit it or not, all of us secretly want to do it.

And so, five or ten minutes after her final orgasm of the night, I was slapping my haunches against her taut derriere -- watching as percussive ripples rolled across her sexy butt as I pounded away at her pussy, until I felt that old familiar twinge deep inside, and asked Madi to turn over so I could finish off the night depositing a half dozen spurts on her face and neck. She said she loved it. We cleaned each other up again and finally fell asleep in each other's arms about four in the morning.

It was a memorable night, undoubtedly a beautiful night, but for some reason, I think I just expected too much from it, from Madi. For some stupid reason, I was sure that whatever happened to me on any given occasion was certain to decide everything that would happen to me for the rest of my fucking life. That puts a lot of pressure on whoever is involved, but that's the kind of shit I always did. It was just the way my immature brain operated. It was my problem; I knew it even then, but I just couldn't stop myself.

Why couldn't I just leave well enough alone? Why couldn't I just enjoy the moment and be happy? Why couldn't I understand that the perfect is always the enemy of the good? Unfortunately, I am a man that can probably pull failure from the jaws of success more adeptly than anyone I know, with the possible exception of Tommy. And so, the next morning, my brain just started thinking of all the things that were wrong about Madi and me being together.

First, Madi wasn't her sister, and I had a thing for her sister years before I met Madi. I started to see the situation from a vantage point that was contrary to my original perspective. I determined that I must have been subconsciously trying to fuck Libby when I was fucking Madi. It wasn't that Libby was trying to have a vicarious sexual relationship with me by setting me up with her sister; it was that I was trying to have a vicarious sexual relationship with Libby by having sex with Madi. It was my problem, I assumed, not anyone else's.

Second, I started thinking that I was taking advantage of Madi because she was too young and too naïve to understand that I was just incredibly unremarkable -- an absurdly mediocre, white male that a paternalistic, misogynistic, racist society had elevated to an anointed place. I was afraid that she viewed me as the great, white hope, when in cold, hard fact I was nothing more than the great, white dope smoker!

It was a societal thing as I saw it, and I was the beneficiary of our society's preconceived prejudices. Still, I didn't feel right about being that beneficiary, because I viewed myself as someone who was unfairly lucky. I got the feeling that Libby and Madi thought I was going to accomplish something, but didn't realize that accomplishing something was easier for someone like me. Even as a lower middle-class, Caucasian man, I was a thousand times more likely to succeed than most everyone else in the world by virtue of the unassailable fact that I was born a white male in that time and in that place. In short, I was a fraud.

Finally, for all my white, male, American, Catholic guilt, I started thinking that maybe I was just lying to myself. Maybe what I was really looking for was a woman from "the other side of the tracks" -- a rich, college girl with an impressive IQ, a family in the suburbs, and a soon-to-be, corporate gig that she would hang on to just long enough to make a boatload of cash before settling down to play soccer mom to our children -- a pair of perfectly adorable, highly intelligent, polite, red-blooded American consumers, just like the two of us.

Maybe Madi was just too much like me. As such, she couldn't possibly be an appropriate match for someone who deep-down, maybe... possibly... probably... aspired to be another young, upwardly-mobile professional schmuck, just like all of those assholes with whom I'd gone to high school -- the ones I despised. Maybe I just hated myself.

It was just like me to overthink everything, but that was what was running through my mind the next morning when I woke up in bed next to Madi. I realized that I was naked, both of us were, and then I remembered that all of my clothes were still in the living room by the couch where Madi had first made me cum. Very carefully and quietly, I got up from bed and found my clothes in the other room. I put them back on, except for my shoes, retrieved my wallet, then came back into the bedroom and crawled back into bed very carefully again, trying hard not to wake, Madi.

I lay there for a little while longer, propped up on my elbow, watching her sleep, thinking. She looked so young there next to me, so pretty, but so naïve and vulnerable, too. For a moment, I seriously questioned my motivations. Just how crass was I in sleeping with Madi? I briefly wondered if deep down I was only trying to get my rocks off, and having succeeded, I should sneak out, head back to Lincoln, and just ditch Madi completely after one night together.

But I also knew that was bullshit. I knew I couldn't do it. For one thing, Madi was Libby's sister, and I was still going to be friends with Libby and Tommy, no matter what, so even if I wanted to, it wouldn't have worked -- I would have continued to see Madi upon occasion and then it would have been just incredibly awkward.

But even if that wasn't true, I wouldn't have done it anyway. It's just not in me. I'm not that much of an asshole. And let's face it, even if I had no emotional attachment to Madi -- and I did have feelings for her -- I'd just experienced the best night of sex in my entire life, so whether it was crass or not, I knew I'd be coming back for more. It was a conundrum, and no matter how much I thought about it, I had no idea what I should do at that moment.

My brain must have been making a lot of noise, because after a few more minutes of staring at her and thinking, Madi woke up to see me hovering over her like some kind of fucking ghoul. As soon as she realized where she was, her face broke into a huge grin, and she craned her neck upward to kiss me.

"Good morning, baby! What are you looking at?"

"You."

"That's nice! I like it when you look at me." She paused. "How did you sleep, lover?"

"Good, fine, I guess. I always wake up early though. I shouldn't stay up that late, because every time I do, I get up at the same time, no matter what time I fell asleep."

"What time is it?"

"A little before nine."

"That is early. Maybe we should tire ourselves out again, so we can fall back to sleep." She smiled at me again, that hopeful, expectant smile that I'd already come to recognize. Suddenly she realized I was dressed. "Hey! You got dressed; how come?"

"I probably need to get going pretty soon", I said sort of matter-of-factly. "I'm supposed to help my brother move some shit before I go back to Lincoln." It was a lie, but it was a lie that I knew Madi would never question, because Madi trusted me far more than she should have. It was a part of who she was -- innocent, trusting, and grateful.

"Oh." I knew it disappointed her, and I wondered briefly if that's why I said it. "Oh well, I guess I'll see you when I see you then. When do you think you'll be coming back to town?"

It was a good question, and one that I hadn't thought about at all. But, all of a sudden, in the moment, I came up with an idea that I suspected would appease her disappointment. "Madi, what are you doing two weekends from now?"

"I don't know. I guess I don't have any plans. Why? Do you think you're gonna come back home again that weekend?"

Right then and there, I made a decision. "You know what I've decided? I'm gonna put in my two weeks' notice tomorrow. I think I need a little vacation. I've been working all summer, and school is going to start up again in three weeks. I don't want to work right up until the fall semester begins. I deserve a vacation, a short one anyway, and you know what, so do you, Madi! Do you think you could get a day off from work -- maybe that Friday or the following Monday?"