Remembering Winston

Prologue

I was just starting my junior year at a four-year prep school in New England. The dorm rooms each housed two boys and were all paired off with an adjoining bathroom. The common rule was that bathroom doors were always kept closed and, when in use, locked, if privacy was desired. During your freshman year, however, you soon learned that you had to allow others free access to the bathroom and overcome your shyness. You became nonchalant, for example, about a "roomie" coming in during your shower to piss, shave, brush teeth, etc., and vice-versa. Bathroom doors were usually locked for only one reason-well, two, really, but one was a pretense for the other. Of course, we occasionally saw each other naked when dressing or sharing the bathroom, but, otherwise, we practiced common modesty and decorum. My friend and roommate, Brent, was also a junior, and two seniors resided in our mate room. I think the school administrators tried to pair upper- and lower classmen, for the "mentoring" factor. It being a somewhat small school, and with most students starting as freshmen or sophomores, we had, all four of us, known each other to some degree for two years or more.

The first weekend after the start of classes was the long Labor Day weekend, during which most students went home. Since it was just a week into the first semester, and my family lived far away in New Orleans, I always stayed at school that first weekend. That Friday night, when I returned from chow to the seemingly deserted dorm, I entered my room, kicked off my Nikes, turned on the stereo, then opened the bathroom door. Strangely, the other door was open and, in the other room, I could see Winston, wearing only a T-shirt and boxers, sitting at his computer-ever the diligent student, I mused.

I knew Winston was staying over the weekend because he had mentioned that morning that his parents were in Africa, and that he didn't feel like driving hundreds of miles to his empty house in Pennsylvania and back. I told him that I would be staying, too. I had, momentarily, imagined hanging out with him, going to a movie or something, but, though he was gregarious and friendly with everyone, he usually only associated with those his classmen or older. Besides that, it was well-known that he dated several different girls-some from the nearby girls' school, a couple of local high school girls, even a local college freshman-and I assumed he probably had dates every night that weekend.. As well as being a serious, straight-A student, and chess club champion, Winston was a fairly good-looking guy, well-liked, well-built (but not athletic), and was commonly seen outside of school in the company of one or more girls, from the plain to the gorgeous.

I, on the other hand, had only resumed exclusively seeing the same girl (from the girls' school) I had dated most of my sophomore year. And her parents had insisted she go home to New Jersey that weekend, for a family gathering.

The Incident

When I stepped over to close their door, I could see, in the high-intensity desk lamp light flooding his lap, that he was fondling, with his left hand, a quite large erection. I blinked and squinted, questioning what I was seeing. But, there it was! Now, ...I've masturbated ever since I can remember, but, having never seen an erect penis other than my own, outside of porn videos, this sight startled and embarrassed me. I swung the door with normal force, catching it just before it closed, and pushed it shut as quietly as I could. I immediately tried to put the incident out of my mind, discounting it as an unfortunate happenstance.

When I returned to my room, however, my mind was, unavoidably, flooded with questions, the possible answers to which further perplexed and perturbed me: Had he not KNOWN I was standing there, perhaps blinded by his lamp?

Surely he had heard my stereo when I opened my door. But he had just stared straight ahead, not typing or mousing, just...stroking. WHY was he at the computer? Was it ON? Yes, I'm SURE it was. If he was unaware of my presence at the time, HE IS NOW! Maybe he's hoping I didn't notice what he was doing. No, he MUST know that I saw him! He was right THERE, not four feet in front of me! Is he embarrassed? How can I FACE him again? I can't POSSIBLY avoid him all year! How utterly awkward! Dammit! Why wasn't he on his BED, where I wouldn't have been able to see him? Why was the door open at ALL? Did he WANT me to see him? THAT couldn't be! Don't even THINK that!

During the first hour or so of mulling over these questions, I heard Winston taking a shower, then running the sink faucet off and on. Finally, there was a knock on the inside of my bathroom door. I bolted out of my uneasy meditation. What now? Already I had to face him?

"Come in!" I blurted out, with trepidation.

Winston appeared, neatly coifed and dressed.

"Hey, dude, I'm going out. Could you do me a favor and answer my phone, in case my parents call, so they don't just get my machine? They hate that, when they're abroad. I'll leave the doors open, since nobody else is here."

The stark contrast between the scene I had witnessed just an hour before, with the bland, normalcy of everyday conversation with which Winston approached me, almost made his words sound foreign. Struggling out of its internal confusion, my reeling brain slowly deciphered his request.

"Okay?" he appended.

I, finally, responded with a terse, "Sure".

He left the bathroom doors open, and I heard his dorm room door slam, shortly thereafter. I assumed he was off on a date. After our verbal exchange, my foreseen uneasiness about facing Winston socially had subsided, but, I was still confused. I pondered the situation deep into the night.

Usually, I eagerly took the opportunity of an empty dorm to masturbate freely and uninhibitedly in my room, but persistent questions about what I had witnessed earlier annoyingly distracted me enough to inhibit my ability to relieve myself. I finally fell asleep, mentally exhausted, before midnight.

Winston returned at curfew, and I awoke when he noisily closed the bathroom doors. Starkly awake, I was instantly, and with unmistakable clarity, convinced that the earlier event of this night had been completely contrived for my benefit. The questions I had kept asking myself had distilled down, after my long musings, to the last two questions: Why was the door open at all?, and, Did he want me to see him?, and the last had to be answered, "YES!"

I immediately began masturbating, with abandon, sensing Winston's presence in the next room, the indelible vision of his engorged cock imprinted in my memory, and with the vaguely expectant fantasy of his desire for sexual contact.

Contact

The following day, Saturday afternoon, I spent on the soccer field, honing my skills. I returned to my room to shower before chow, only to find, once again, the opposite bathroom door open. There, again, was Winston, completely nude, this time, slumped down in his chair, legs straight out, in front of his computer, obviously masturbating his ample cock. This time, his eyes momentarily, almost imperceptibly, shot over to mine. I slammed the door in an instinctive fit of defiance, knowing that he was erotically manipulating me. Although uneasy about it, I found the look on his face powerfully magnetic.

I showered quickly, knowing that I would surely succumb to Winston's advance, but completely unsure of what that would entail. I dried off, donned a T-shirt and gym shorts, opened his door, quietly entered his room and strode slowly to the side of his chair. He was still stroking his big cock, which, I observed, was much thicker than I had remembered. Our rooms were dead quiet, except for the spacy hum of his computer's CPU. I looked up from his cock to his computer monitor to see a full-screen image of a guy with a huge erection. He closed the jpeg and quickly clicked his mouse to open another. This one was a close-up of a guy with his mouth wide open, about to devour another huge erection. Winston successively closed and opened a couple of dozen images, including hunks, cumshots, gay scenes, etc. Between viewing those images and the sight of Winston stroking his cock, I became extremely aroused.

Finally, Winston got up from his chair and stood inches in front of me with a serious expression on his face. Reaching behind him, he doused the desk lamp, so that the room was bathed only in the glow from his computer screen. He put the palm of his right hand, fingers down, on the front of my T-shirt then slowly slid it into and past the elastic waistband of my shorts. He firmly clasped my semi-erect penis, and I felt its head engorge. My heart bounded in my chest, as my bloodstream filled with adrenaline. I knew I was about to experience something completely foreign and unexpected; something, it turns out, I would always remember as if it happened yesterday.

In this position, he gently coaxed me, helplessly, backward, to the foot of his bed, his full erection bobbing, heavily, as he stepped. Unwilling to look at his face, I stared at his chest. With both hands, he pulled my shorts down to my knees, then pushed them to the floor with his right foot.

He rested both of his hands on my shoulders, and I sank to the bed. He, gingerly, pushed me into a reclining position. My cock rested on my abdomen, as he, sitting beside me, softly ran his fingertips and thumb up and down its underside, occasionally lubricating his fingertips with dollops of his precum, which seemed to flow freely from the tip of his cock. I lay there, dizzy with the confused emotions accompanying finding myself in this odd situation; but those feelings were gradually overcome by my unadulterated, carnal lust. Soon, there was a small puddle of my own precum on my belly, and he started using IT on me, too, as well as on himself, to my elation! Then, he lifted my cock to perpendicular with one hand, and fisted it loosely with his other hand. The nerve-endings in my prick were bristling, and my cock leapt on his every downstroke. I don't think I had ever been that hard!

Winston then stood up and opened his night stand drawer, removing a jar of Albolene. He dug out a blob with his finger and, kneeling between my legs, applied it to my standing penis. The gel melted quickly with the friction of his strong hands on my hot, petrified organ. He kneaded my cock for what seemed like hours, alternately tightening and loosening his grip and slowing down whenever he sensed I was nearing orgasm. At one point, he did something I call the "rope climb". That's where he followed one fist behind the other, always from head to base, continually, it feeling like I was penetrating a mile-deep pussy. This technique sent spasms of pleasure deep into my groin, eliciting a long, involuntary, staccato moan from my throat.

My cock was almost painfully hard, feeling as if its veins would burst. The sound of my excessively lubricated prick squishing in his hands heightened my lust even more.

Then Winston started doing something that swept me into unimaginable ecstasy, causing me to hyperventilate until I thought I was going to pass out! "MY GOD! What the hell is he doing?", I wondered. Breathlessly, I lifted my head to see. He had the thumb and forefinger of both hands firmly around my cock, stroking vigorously, and methodically, in opposite directions. The sensation was incredible! I looked at Winston's face. He was dutifully watching his "handiwork" with the determined countenance of someone concentrating on a difficult task.

I knew he had decided that it was time for me to cum, which was FINE with me, because there was no way I could hold back now, and he knew it. When I held my breath, tensed my whole body and began a long grunt, Winston moved one ring of fingers to the base of my penis while tightening the other ring of fingers and stroking regularly, concentrating on the pleasurable jolt he was causing me every time his fingers slipped down over my swollen glans, onto the shaft. Continuing to watch this lustful spectacle, I finally relaxed, surrendering to inevitability. Winston then, expertly wrapped his whole fist around my cock, pumping it firmly and steadily. My first three cum spurts shot straight up about two feet, landing on my belly, and the remainder poured copiously over his skilled hands and onto my scrotum. I lay my head back down, mouth open, as my breathing slowed, wondering what to do next. Winston disappeared but quickly reappeared with a hand towel to wipe my cum off of me. I gazed gratefully into his face; he returned a slight smile of self-satisfaction.

With the towel in his left hand and his right hand still covered with my cum, he stood up before me and furiously jacked himself off, as I sat up on my elbows, watching, and, within a minute, a "hnnnt" sound escaped from his throat, and he began intently ejaculating stream after stream of cum onto the towel. My fading erection became turgid again, as I watched this exhibition. I thought he would never stop cumming! Finally spent, he wiped off the cum clinging to the end of his cock and threw himself across his bed, motionless, except for the heaving of his chest..

I retreated to the bathroom to wash off the Albolene and the drying film of cum remaining on me, and, not knowing what else to do, returned to my room, closing my door behind me. A few minutes later, I heard Winston washing up. I slept very well that night.

The next night, when all was quiet, I entered the bathroom to, again, find the other door open. I instinctively knew what this meant. I knocked on the open door and entered Winston's room, as he was preparing for a date, his stereo blaring. Wearing only boxers, he looked at me, hooked his thumbs into his shorts, raised his eyebrows, and I nodded. He dropped his shorts and, soon thereafter, we stood facing each other, reveling in our masculinity, jacking our hard cocks and rubbing them together, finally ejaculating on each other. While we were jacking off, I felt obliged to reach over to surround his bountiful cock with my well-lubricated hand to stroke it, but, he would have none of it, and pushed my hand away. After we came on each other's cocks, I went to the bathroom to wash up, closed my door upon returning to my room, and heard Winston washing up before his date.

Continued Contact

After these two episodes, Winston and I deduced that with my roommate's working at the library on Tuesdays and Thursdays from 5:00 to 7:00 p.m., and with his idiot, jock roommate going to tutoring sessions on Thursdays at the same time, gave us ample time to "play" almost every Thursday afternoon that semester, as well as a few other fortunate times, when one or the other of our roommates was away. I made a habit of abstaining from orgasm, if not masturbation, for a day or two before every Thursday, so that my anticipated Thursday prelude to orgasm with Winston would be all the more intense, and my resulting ejaculation more plentiful.

Sharing his ample cache of gay jpegs and video porn, sometimes Winston and I would just lube ourselves up and seriously jack off together; sometimes he would jack himself off, making me hard, then give me one of his luxurious hand-jobs. Sometimes he would briefly suck my dick while jacking me off, which was admittedly pleasurable, but a little uncomfortably gay to me.

Sometimes he would rub our stiff, lubed cocks together, which was intensely pleasurable and erotic, and, somehow, not as gay; and sometimes we would cum together this way, simultaneously pouring out our cum together, the sight of mine or his ejaculation immediately triggering the other's. Mysteriously, though, he never let me get him off, instead always concentrating on getting me off.

Epilogue

During our sexual encounters, Winston and I never exchanged a word, yet we continued to socialize as usual, when in public settings.

After the end of my junior year, I never saw Winston again. Although I often fantasized about seducing another guy, especially my soccer mates, the entire next year, and throughout University, I lacked Winston's moxie, and never had another homosexual encounter. I still speculate whether Winston is gay, straight or bisexual. While I'm fairly positive he had had another jackoff buddy, or buddies, before me (since he was so adept at it), I wonder why he targeted me, aside from circumstantial convenience on his part and fortuitous chance on mine.

Several years ago, I made an online, "white pages" search for him and found that he is a partner in his father's architectural firm, but was unable to find out any more about him.

I got married shortly after college and now have three children. My wife and I often use pornographic videos to enhance our sex play, but, unbeknownst to her, I often privately masturbate to male/male porn videos, relishing the handjob scenes, remembering Winston.