The things he didn't tell me
Boston, Fall 2007.
"I don't really know anything about these people", Jake had said the night before, at Kendrick's, a crowded bar two blocks away from where we both worked, his perplexed voice barely audible in the swarm of our inebriated colleagues. "You know, it's strange, you work with people for years, you see them every day, and yet..." he trailed off.
He was looking at me intently. There was something pleading, a little apologetic too, in his tone. Whether he was appealing for an explanation, venting out loud some regretful realization, or extending an invitation, I couldn't tell. "What do they know about you?" I asked, and he smiled, looked down, and pulled away his left leg, which had been faintly pressed against mine for the previous ten minutes. Or so I liked to think.
I had moved to Boston some six months before, in a particularly cold spring. Boston had seemed as good of a place as any to get a fresh start, after two difficult years spent in New York trying to fix a relationship, to engage intellectually with my job, to discipline myself to curb the aimless anarchy of young adulthood. The consulting firm I worked for had an opening in their Boston branch; I was well-liked, well-regarded and got the job easily. I had just turned 30 and felt no ties strong enough to keep me from trying something new.
My first apartment was always supposed to be temporary; it was small, blandly furnished, too quiet, and I hated it. My landlord seemed to harbor similar feelings towards me, for reasons about which I was never entirely clear. I had intended to look for a place to buy, but kept postponing the exertion: I was loving my new job, building a social life at the slow pace I had intended and enjoying the city. When I received an unexpected notice from my landlord to vacate my apartment by the end of September, I had just been back from some time off on the West Coast and was not prepared to look for nor settle on a place to buy. My trip had been emotionally intense, just two weeks of upsetting lows and exhilarating highs. I was actually looking forward to shutting myself off in my apartment and emerge only for work, until I found the drive and energy to mix in the world again.
Jake came to me with the perfect offer: he was taking a month off work, travelling to Australia to visit the country and a college friend who had moved there a few years before. He was looking for someone to house sit or sublet his apartment. It bought me a month and it gave him, he said, some peace of mind – and a modest financial return.
I liked Jake Winfield. He was a couple of years older than me, but it still put us both in a somewhat sparse age-bracket at work. Most of our colleagues, or at least our male colleagues, seem to be either over 50 or just fresh out of college - interns and PAs mostly. He had thus caught my eyes on my first day at work, but, for all his warm, calm and cordial demeanor, there had always been something opaque about him. Aloof and oblivious often, he could also be earnest and engaging at times, as well as a little intense when immersed in his work. Dedicated and studious, he took his job and his performance more seriously than I ever managed, my allegiance and commitment to the betterment of the corporate world never morphing into a calling as it sometimes seems to do for Jake.
As an occasional smoker, I benefitted from quite a few gossiping sessions during smoking breaks with colleagues, mostly women. They all seemed to observe a general, if reluctant, deference towards his privacy and I never heard more than vague morsels about his work-out obsession and a rumored broken engagement, or suppressed giggles about their desire to set him up with a niece or girlfriend of theirs. There were all in obvious awe with Jake's handsome if conservative good looks and his elegant if subdued charm. Jake was tall, lean and broad-shouldered, with short dark hair, somber blue eyes, a clean-shaven angular face and, I noticed early on, very large, long and sturdy hands. His fingers and palms stood out as rugged, hairy and brawny, the only blunt manifestations of rough masculinity that weren't tamed, softened or neutered by his fitting suits and impeccable grooming. On some occasions, I shared a cigarette with Jake himself (he didn't smoke, except before important presentations he felt nervous about) and, as I'd lit his, these hands, cupping the flame, always jolted me a bit.
These breaks usually had a particular beauty to them, they lasted longer than my usual ten minutes and were always brought to an end by the interrupting arrival of a third person. Jake's attitude was often an inordinate sequence of showing himself relaxed, intense or politely guarded. I would maintain some distance, however, letting him vent or reflect or enjoy the silence, letting him keep the things he didn't tell me.
The apartment deal had been quickly done, a week before his departure, leaving us both relieved to have found a last-minute, mutually beneficial solution. That Saturday morning, a few hours only after waving him goodnight at Kendrick's, I was buzzing at his door, ready to drive him to Logan.
He was excited to go and was more animated than I had ever seen him. He didn't seem worried to leave his place to a stranger, which in a sense I wasn't, and patted me on the shoulder at the airport curb. "See you in month", we both said, almost simultaneously.
I had packed the little I owned in my car and was all settled in by midday. I had never actually seen the apartment, even when agreeing to sublet it. It wasn't before I had put all my stuff in place and dropped on the sofa that I started to take it all in. The place was beautiful and comfortable. In some ways, it resembled Jake himself. It was dark, elegant, masculine, a little austere. Some exposed brick walls in the living room and bedroom. Retro style leather couches, tons of books and magazines neatly stacked, big television, nice cluttered desk in the bedroom, large comfortable empty bed. Some weights were on the bedroom floor, pushed in a corner. It also looked like an apartment that had been quite messy before a recent, somewhat rushed, tidying effort. This place was now mine, for the time being.
I felt a strange intoxication, a restlessness I couldn't quite grasp. I thought it resembled the occasional, even if somewhat inexplicable, urge to masturbate when I settle in a hotel room. I had, up to this point, successfully disciplined myself to divert my libidinal urges away from Jake and onto other outlets – which were numerous enough as a newcomer in an unknown city. Jake was attractive, in an obvious and generic way, but I had outgrown, after lessons learned the painful way, the self-defeating impulse to fall for straight men or for coworkers. Jake Winfield fit at least one of these criteria.
He provided a welcome distraction, however, in a working environment devoid of subversion, asperity, or oddity, where checking the shape of a man's ass in tight suit pants felt like an act of exhilarating and seditious depravity. And there had been times where he had been a full day source of curiosity, attention, and beguilement. But the day would end and the attraction wither (or be quashed by a night-out, a one-night stand, a jerk-off session, or a good book).
A few years ago, my good friend Tom, playfully devious and sexually extroverted Tom, was riding with me on the subway uptown. He told me about his hobby to pass the time when bored in public transportation. "Pick a guy, any guy, he doesn't have to be hot – though it helps. Look at him attentively. Then visualize in your head two things: when he lost his virginity and the last time he jacked off." I smiled. "Try it," he said. He leaned closer to me, nudged his head toward an ordinary frat boy, and whispered: "He fucked a girl in college, he was still a virgin but always lied about it to his friends. He found a willing, sluttish redhead. The sex didn't last long, he stuck to missionary, his fleshy pasty ass bobbing up and down. He came without warning, pulled out too late, cum dropping on his thigh."
I couldn't suppress a giggle.
"See?" he said, muffling his enthusiasm. "Hot, right?"
"I guess," I said.
"Okay, then, last night, visualize him in front of his computer, his pants down his ankles, wearing his white tennis socks and his red hoodie, spanking his meat furiously while his head leans closer to the porn on the computer screen. Can you see that?"
For the rest of the ride, Tom expanded on a guy with a janitor uniform jerking off in the broom closet, on a young Asian with a bowtie losing his virginity to his babysitter ("She practically raped him"), on a bald and bearded businessman masturbating in the bathroom at work, on a thirty-something guy in gym clothes fucking his first girl along with his best friend.
"Fun, right?" he concluded, as our stop was approaching. "It's most intense to do this with a guy seated next to you on a plane. Trust me."
So I had attempted to play that game once using Jake. We were seated in front of each other at a staff meeting one day. I was a little listless, mildly bored by his update on a project on which we all had to collaborate to a degree. I'd follow the rules, I thought, watch him carefully and start visualizing. I didn't get much further than gazing at his cheek (a midday shadow was already rebelling against his careful shaving), the ear of his lobe, a small cut on his neck. He noticed my stare and began to fluster, stammering on his otherwise engaged and animated rendering of synergetic outsourcing and forward-looking downsizing. "What?" he finally asked, puzzled and apprehensive.
"Nothing, sorry. I was just wondering whether their IT team does actually have the organizational structure effective enough to appropriate the change you seem to imply."
I really had no idea, so I decided to stay silent and look inquisitive.
He frowned for a second and blushed. Then delved into a long and rather passionate defense of his plan, twitching his tie, or leaning forward towards me, or searching for words looking intently at the ceiling, or rhythmically tapping his long fingers on the table when enumerating the necessary steps to undertake. I smiled at him. He smiled back and relaxed. I thought briefly he might actually be even sexier right then, than in whatever situation I could try to visualize at that moment; but, as his attention was taken elsewhere, I flashed briefly to him jerking off in his office on a late evening when everyone had gone (his pants down to his loafers, his tie swung back over his shoulder), and decided otherwise.
And here I was now, within his most intimate space. The place he gets home to when he leaves the office. The place he walked into the previous night, after the office party, a little dazed and drunk and sweaty, with his top two buttons undone. The place he stepped out of when I picked him up this morning, casual and expectant and unshaven. These are the rooms where he lounges, sneezes, dozes, circles around as he talks on the phone, checks his private emails, dines and drinks.
The Jake Winfield who wasn't at work was still a furtive image; I saw him most relaxed when sharing a sandwich for lunch with his direct boss, a fatherly figure of 55, warm and caring with Jake. I saw him vacant and stern when absorbed by his work, loosening his elegant posture into a burly concentrating figure. I saw him sociable and pleasant when taking a break with me or receiving the politely flirtatious morning accolades of his assistant, a young wholesome girl who, to me, always seemed rattled by him. I also saw him commanding at times, when directing and motivating members of the staff, exuding a confidence which was undeniably sexy. But the private Jake Winfield, who'd walk in socked feet and sweatpants around his bachelor apartment was very much elusive.
I started to walk around his place, marking the locations where he'd be brewing coffee, snacking, cooking, where he'd be opening his mail, resting, watching television, where he'd be showering, toweling, grooming, where he'd be napping, sleeping, waking up with a morning erection. This is the door he'd open to nudge into his bedroom the women he'd take home, these are the sheets he'd pull or push, ruffle and soil.
I went back to the kitchen and drank some orange juice from the carton I'd bought. I noticed there were a lot of framed pictures everywhere around his apartment. He was on almost all of them, but never alone. They showed him at all ages, in all moods, in all sorts of company. A young Jake beaming with a sport trophy and teammates, or surrounded by his family at graduation, or smiling bravely, soaked by rain in what looked like Yosemite. I felt a pang of guilt and had to remind myself that he had himself asked me to spend a month amongst all his belongings, that everything I would see, touch or use was left there by him knowingly and willingly. I was not an intruder, I was not a stalker. But there was still something illicit, and erotically charged, in my presence and my unchecked curiosity.
I made some coffee and went outside to have a cigarette, stepping on the landing of a fire escape turned into a tiny balcony. Jake's apartment was on the fourth floor, there was a nice, urban view on the busy street, and on other similar buildings across. I thought about all these windows, all the people behind them who could watch or glimpse at Jake every night. What did they see?
I went back inside and decided to be more methodical in my drawing sketch of Jake. The magazines were unsurprising, if eclectic: The New Yorker, Sports Illustrated, Conde Nast Traveler, National Geographic, some alumni magazines from Cornell, a couple of fitness monthlies (whose covers all seemed to promise great abs and strong arms – is that something he is concerned about?). The books were an even mix of fiction and non-fiction (many of those about business negotiation, public speaking, and biographies of sport figures), with a few glossy volumes on architecture, sailing, and the Kennedys. A few DVDs were piled orderly next to the TV – they mostly turned out to be videogames on closer inspection, except for "Office Space", the "Lord of the Rings" trilogy, a "Sopranos" box-set and a couple of classic DeNiro movies.
I opened every cupboard in the kitchen, every drawer and wardrobe. He eats healthy, he dresses well and has a rather impressive collection of T-shirts and sneakers. I did find all these shirts, suits and ties in which I see him every day. My hand grazed the crisp, tight pale blue one I recognized. It felt tantalizing to touch the fabric, then creepy, then briefly idiotic, then beguiling again.
I found his stack of underwear, most of them white or grey Y-fronts, a bunch of boxers too. Without thinking, I undressed, almost mechanically, and put on one of his pair of briefs. They fitted perfectly. I put my jeans back, pulled a white t-shirt from his pile, and went back to the living room, to the couch, to catch my breath and enjoy the feeling of Jake's underwear on my skin. I felt incredibly, intensely aroused.
I knew that the motherlode of information would be on his computer. This is where, nowadays, all our life is stored, gigabytes of our most intimate longings and experiences. But I wasn't sure whether I actually wanted to know too much too fast. Jake was slowly morphing into a mirror image of my current horny self, my head was increasingly buzzing with images of his own masturbatory urges. It was enthralling enough to enjoy the slow shift of his apartment into a private retreat where he is able to undress, unwind, and unleash his urge for frantic jerking-off or languorous edging. I wasn't quite ready to be brought back to a reality of Jake having little porn on his computer, of him boringly watching overexposed pictures of straight websites with milfs, sluts and eager Eastern European tawdry blondes. The infinite possibilities of Jake's sexual habits would whither down to generic insignificance, and I would spend a month perfunctorily lusting about a fairly average, albeit good-looking, straight guy.
Watching his clothes, clean, ironed, folded, hanging in his closet, I had undressed him. Naked in front of me, around me, next to me, in the next room. His presence in the apartment was by now intensely sexual and his fidgety ghost longed to jerk off as much as I did.
Where would he do it? How? He might need or like some lube. Where would I hide it if I lived here and had to vacate the place for a while? I went straight to the first nightstand, on the right side of his bed. I was almost disappointed to be successful so fast. I did have to rummage a bit through Advil's, watches, or cufflinks, but there it was, at the rear of the drawer: a bottle of KY. So he sleeps on the right side of his bed. So he likes to have lube handy. So he probably sometimes jerks off lying on his bed.
The bottle was almost empty – which made me irritatingly aware that I couldn't be using it myself more than once or twice without making it possible that he notice it when he gets back. The thought occurred to me that I should actually use it, and use it all, to have him know that I jerked off here using his lube. I could picture the moment when he would be by his computer, his pants open and his dick out, getting hard, and he'd come to his nightstand and find the empty lube, realizing while gripping his hard cock that I had just been doing the same just some days before.
I felt a little dizzy. I went through all the picture frames again in his bedroom, until I found the one I knew I had noticed earlier: Jake on a beach, in swim trunks, standing next to a shorter, stockier blond surfer, flashing a big smile. His body was tan, his trunks hanging low, showcasing a young flat stomach and some protruding pubic hair. His chest was somewhat hairy, but whether he trimmed it slightly or the hair itself was short, I couldn't tell.
I lay on the left side of the bed, undressed completely but for Jake's underwear and started to slowly stroke my already hard cock. I held the frame with my hand, staring at Jake's dashing smile and body. Once it was burned in my brain, I put it back down and reached for the lube. The bottle was a little sticky, which brought back flashes of Jake jerking off on this very bed. I held on to that image, picturing him jerking off with me, right next to me, looking at me intensely, smiling warmly. Then I saw him cumming, I saw his sperm splatter all over his chest and I too reached climax, in somewhat violent shaking bursts.
I was panting, dizzy and flushed. I decided to stay still, not move, feel my cum dry on my body, trying to hold on to the image of Jake lying next to me, recovering from an equally intense orgasm. I closed my eyes and was filled with the bliss of realizing that this was just the beginning of the weekend, of the whole month I would be spending here. I fell deeply asleep, warmed by the autumnal setting sun through the window and the heater who seemed to be going full blast.
* * *
I woke up two hours later. It was dark outside already, the sun was almost down. I was starving. I hopped in the shower and, as I was looking for some clothes, decided to use Jake's. I snapped a couple of pictures of the inside of his drawers and wardrobe, to help me put everything back into place at the end of my stay here.
I put on a pair of his boxers and a Cornell Lacrosse t-shirt. I had bought a sandwich that morning and gulfed it down, sitting on the couch. I noticed that I had received some texts from friends I had made in Boston; Charlie (a girl) and Chuck were among my favorite people here and were trying to get me to join them at some party in Cambridge. Any evening with Charlie and Chuck was bound to be lovely, or fun, or wild, and Chuck was a very enthusiastic bisexual guy with whom I had ended up hooking up a few times.
Yet, I couldn't bring myself to set the motions needed to leave this apartment. Not tonight, possibly not this weekend at all. I ignored the texts and quickly cleaned up the plate I had used. I didn't want just yet for this apartment to display the visual evidence of my presence here.
I went back to his bedroom and sat at the desk. I took a deep breath. I had noticed that the laptop we all received from work and use wherever we go was missing; he had most likely taken it with him on his trip. A Mac was on his desk however, the one he must have gotten for private use. I opened it and turned it on slowly, aware that much of my fate was resting on whether I could actually access it. It blinked and I was facing the image of his desktop, cluttered with files and documents. A spark seemed to rush through my spine. This is it.
I tried to collect myself and concentrate on the things I should not be doing, for fear of him finding that I had been snooping in his things – he had given me the wifi code but hadn't mentioned I could use his computer. Do not open his emails. Do not save anything. If I did end up on the internet, which I would, erase all cookies and history. This was actually where I decided to start. I opened his Safari and went straight to his browsing history. Here again, as earlier in my search for his lube, I didn't have the time to think much before I found exactly what I was looking for. Last night, Jake Winfield had been watching gay porn.
The names of the sites did not leave any room for doubt. Most of them I didn't know, some I was turned on to notice were sites I often visited myself. I opened them one by one. Since I have learned from previous experience that you can never fully guess what kind of porn people you know or meet do watch in their own time, I was careful not to make too many assumptions as I went through the list. By the time I reached its end, I could establish that Jake had been wanking between 10:27pm (I remembered him leaving Kendrick's around 10) and 11:19pm. He had first gone to a site that showed a whole bunch of pictures of guys jerking off, then moved to a few sites dedicated to fucking (a couple of them bisexual), then spent the last ten minutes on a site that seemed to specialize in various kinds of athletes fucking each other's brains in locker rooms.
I paused for a second, to take it all in and reconcile my recollections of Jake and what I had just found. Jake is attracted to men, Jake is turned on by guys jerking off, guys fucking women together, guys having sex. Then, smiling, I said outloud "Jake Winfield likes cock".
I stood up, walked zombie-like to the living room and started pacing. I opened the window a little and smoked a cigarette, carefully blowing through the crack. I opened one of the beer left in the fridge. I sat on the couch, but quickly stood back up. I was restless, my mind cluttered by surprise, exhilaration, perplexity and lust.
I went back to the laptop and to the browsing history, and looked further back in time. Jake apparently jerks almost every night, typically around 10:30 for thirty minutes to an hour, sometimes he starts past midnight – probably when he's back from a night out. That pattern seemed to indicate that he didn't hook up much, at least in the past two weeks. I checked some other, different sites he visited; they confirmed he had fairly regular tastes – and very much similar to mine.
Browsing down, and just before reaching the point when I had seen enough for now, something did stand out. Two weeks ago, on a Sunday, he had spent five hours straight on gaydar, a hookup site. I tried to open it, but it asked for a username and password.
I was quite familiar myself with this site. It was one of the popular ones, which I had used quite intensively, even if sporadically. I would go through phases, usually lasting two weeks to a month, where I would somewhat obsessively spend hours on end chatting with guys and sometimes actually meeting up for a fairly anonymous one-night-stand. I knew the feeling of logging in, browsing profiles of users online, fielding lame, tiresome enquiries (Sup?, Stats?), looking at pictures of dicks and chests and muscles until they all start to blur into one. But I also knew the feeling of ultimately hitting it off with someone, shedding of lot of inhibitions by sharing intimate fantasies and dirty talk, unlocking private pictures for us to actually see each other's faces and letting the fantasy becoming a touch more real and very much more intense. I knew the feeling of spending five hours straight on this site, and usually ending them with a quick and at times abrupt disconnect right after you have finally released all the cum that had been building up.
It dawned on me that I may have been chatting once with Jake, if he had been visiting the site for a while. But I would have recognized him, as I would never spend too much time chatting with a guy if he didn't, at some point, show a picture of his face. But Jake definitely has a profile on the site and it felt suddenly urgent that I find it out. I went to fetch my own laptop, sat on the bed and turned it on. I opened gaydar, logged in and went to the search function. I filtered my search by location (Boston – downtown) and age (28 – 32, as Jake might be one of those guys who shed a couple of years on their profile). A bunch of profiles came back. The ones displaying a face were easy to go through and eliminate. The ones displaying a chest I had to scan through attentively, holding Jake's picture on the beach to make a more careful comparison whenever in doubt. The ones showing just an erect penis were, unfortunately, useless to me. Nothing seemed to match – which meant he probably was one of those "dickpic" profiles. My mounting, and irrational, resentment was quickly quashed down when I realized that, indeed, so was I (my profile was on the search results).
I closed my laptop and went back to the desk. I finished scanning through his web history, but it didn't go further back than three weeks. He did erase it at some point and probably had a good reason to do so. Yet his leaving for a month and letting his computer near a total stranger hadn't been enough of one to erase it again before he left.
I was still convinced that there was more to be found. If Jake was such an avid consumer of online porn, he most likely had some sort of private collection. I surprised myself when I stood up and went to lift his mattress. Nothing there, of course, and I smiled at my old-school foolishness that made me think, just for a moment, that a single grown-up man would hide a stash of dirty magazines under his mattress, like a 1970s teenager. I went to the living room and rummaged through the area and pieces of furniture around his TV set, but I did not find any hidden DVDs. It had to be on his computer.
I sat down at the desk and started a careful examination of the different folders that were on his hard drive. I had started by the main pictures folder but knew beforehand nothing of a sexual nature would be stored there. I decided to keep the enjoyment of watching hundreds of pictures of Jake for a later time, a later day. He had many other folders, and had many sub-folders, and sub-sub-folders created and filled with various documents pertaining to work, academic interests, hobbies. I went through each, one by one.
I was started to feel a little numb when, four levels down some kind of accounting folder, I was faced with two new sub-folders that, finally, seemed promising. One was named "pics", another "vids". I had seen so many pictures already today, browsing through the websites Jake had been jacking off to last night, I opened the video folder first. I had a quick, shuddering startle as dozens (hundreds) of video files icons suddenly appeared on the screen. That was a lot of porn. I quickly scanned through their names and they seemed to fit with I had made out of Jake's tastes so far. Of course, to see whether Jake had more deviant or peculiar fetishes would require watching them all. I had a whole month ahead of me and I was, again after the tedious fifteen minutes opening boring folders, back to a level of frantic arousal and curiosity that led me to open the picture folder. It was neatly organized in various subfolders, most of them apparently describing the main attraction to the pics ("JO", "fuck", "oral"). Two others stood out: "me" and "gaydar". I noticed my hand shaking a bit when moving the mouse to the "me" folder" and double-clicking it.
This is where it all comes together, I thought, glancing at tiny icons of pictures apparently displaying Jake and his naked body in various forms. This was where this whole day has led me to. From the first drawer I opened, from the first stack of magazines I checked through, this was what I was always trying to find or get a sense of. This was how I was hoping my horny quest would be ending, in a fantasy world constructed since noon that day.
I quickly opened a bunch of the pictures, at random, to get an idea of what I had just found. The folder seemed to consist of sets of pictures of Jake taken with a web cam from the very place where I was sitting. It also had yet another folder, named with an apparently random sequence of numbers. Each series of pictures, obviously captured at different points over the last few months, showed Jake progressively undressing, jerking off, posing sexy, zooming on various parts of his body (including many shots of his cock in different stages of arousal), and cumming for the camera. In one series, he starts wearing a t-shirt and jeans, in another just wearing a robe (and looking like he just took a shower), in yet another wearing the kind of business attire I see him every day in. One caught my eyes too, where he looks like he's just back from a run: he's all sweaty and wearing the jogging attire in which I had once seen him leave the office building.
I did feel a certain shortness of breath, a shakiness that I rarely experienced. I was so horny, my dick was so hard it almost hurt a bit. I started stroking it, but the lightest touch seemed to be close to sending me over the edge. I couldn't go on much longer, I knew, so I decided to take one, or two, series of pictures and enjoy them, just those for today, instead of frantically opening all these pictures in no order.
I first picked the series with his shirt and tie. There were about fifteen pictures. In the first one, he was fully dressed and staring intensely at the webcam. In the next one, he had his shirt open with his tie still hanging loose and wearing only white briefs underneath. He was rubbing his chest. The next two were close ups of his dick, half hard, with his briefs slightly pulled downed. His cock was beautiful; it wasn't particularly thick, but it seemed very long, with a great smooth texture and a shiny bulbous head. Then he was jerking off, with his shirt wide open and no tie. Then, close-ups of his now hard dick, one clearly showing pre-cum dripping a bit. Then he was fully naked and the rest of the series showed him jacking off, closing his eyes, or staring at the cam, or looking up at the ceiling in some kind of ecstasy, or looking down at his own cock, at the blurred movement of his hand stroking it.
I started the series from the beginning again, watching them slowly while carefully jacking off. It was odd to recognize the room, every object in the background. I could see that, at some point, the lube bottle is on the night stand behind him; he must have stood up and helped himself.
I picked a second series, a longer one which had caught my eye. On the first few pictures, Jake was intently looking at his screen, never eyeing the camera itself. He wore an old, loose white t-shirt. Then, suddenly, the chair has pushed away from the camera frame and Jake is seated on the floor, his back against his bed, his legs spread wide and straight, both hands holding his cock, still wearing his t-shirt but naked from the waist-down. A large number of near identical pictures followed, all showing Jake highly focused on his dick, looking a little dazed and enthralled with his own erection. On one picture he seemed to lick precum, presumably, from his fingers. He then appeared lying on his back, splayed on the carpet, jerking off with one hand, pinching a nipple with the other. A few of these were followed by a succession of grainy and blurry pictures of Jake appearing to completely lose himself in his own lust. He raised his legs. He humped the carpet. He touched his hole. He kneeled on all fours, his hand reaching behind to pull his hard cock back. He curled backwards trying to suck himself (unsuccessfully). He raised his legs again, high and wide, his big white right foot appearing even bigger as it got closer towards the camera lens. He lay on the bed, his head dangling on the edge, his back bucked, his pelvis raised, his tongue manically darting out. He was back on the carpet, on a downward-dog like pause, his head flat against the floor, still furiously jacking himself. He was on his back, his knees raised close to his chest, fingering himself. The last picture showed him kneeling in front of the bed, his back to the camera, his face buried in the sheet. There was a quite distinctive white puddle on the floor, the tip of his long, semi-flaccid cock almost dipping into his cum.
I was enthralled and deeply shaken; the elegant beauty of everyday Jake was here transformed and channeled into a manic, sex-starved animal. I couldn't help but think too about why he would record these sessions and save into screen caps this psychedelic flip book of masturbatory abandon. I imagined him watching himself and I couldn't last longer; I pulled out my t-shirt, quickened my stroking pace and came all over my chest.
My vision was a little blurry, but when I recovered and could see clearly again, I quickly clicked back to the last picture of the first set. I was facing, on the screen, an image of Jake mirroring almost exactly my own situation: on this chair, facing a screen, chest full of fresh cum. I smiled.
I wiped myself off with Jake's t-shirt and took a deep breath. The release had been incredible and I needed to cool off, if I wanted to avoid being driven mad by lust. I quickly added a few layers of clothing, grabbed a beer in the fridge and went out on the balcony to smoke a cigarette. The evening was peaceful and the street was quiet, save for a couple of young women, already drunk and cheerful, stumbling on their high heels, one of them shouting "Never, ever" between giggles. I couldn't decide what to do next. I felt so fully affixed to Jake's apartment, nailed and clipped to its walls, furniture, and the musky undertones of Jake's raw intimacy. A part of me wanted to sit on his couch and watch one of his movies, another, with an admittedly increasingly stronger pull, wanted to take my clothes off again and venture back down the rabbit hole of Jake Winfield's solitary debauchery. Unable to fully tame my emerging addiction, I decided to take a brief look at the "gaydar" folder on his computer, to get a teasing preview of what my Sunday would most likely be made of.
The folder had about a hundred of pictures of different guys. Jake had obviously saved the profile and private pictures of guys he had chatted with – or just fancied. Most of them were at least decent-looking, but their types and ages varies widely. Scruffy and preppy, twinks and mature, nerds and bad boys, Jake seemed to be non-discriminating – and easily turned on. As I scrolled down and opened a few of them, I did recognize a small number of guys I had myself either noticed on the site or actually chatted with (none with whom I hooked up). Then I froze.
Towards the end of the list, I recognized my pictures. Pictures of my dick and body, which a lot of people could see by browsing the site. But also my private pictures (webcam shots of my face or flattering pictures taken at Central Park a couple of years ago). And one picture of the kind I almost never take, let alone send: a picture that shows both my face and my cock.
I could count on my hand the occasions on which, and against my better, cooler judgement, my lust had led me to snap cam pics of my jerking off; there were all when I had become enthralled in a very hot chat session. And this hadn't happened for a while; in fact, it had happened only once since I had moved to Boston. It was during my last spell on gaydar, the first half of June, a while back. I had started chatting with this guy Will and we had managed to quickly get past the usual banalities. Whereas I usually led the conversation and liked to push the other guy beyond his comfort sex zone, Will had managed to do the same to me. He succeeded in making me pour out fantasy scenarios I was barely aware I longed for, sharing past experiences I had forgotten about and driving me completely mad with lust. This happened only twice and the second time, he dared me to snap a picture of me at that very moment and email it to him. It was that picture at which I was staring right now, on Jake's computer, in Jake's room.
I could not make sense of any of it. Had Will and Jake met on gaydar and exchanged pictures of guys they previously chatted with? I felt angry, upset at my stupidity and at their callousness. But something was nagging at me. I went back to the "me" picture folder and opened the sub-folder with strange numbers in its name. I had neglected to look inside it earlier, the abundance of sex treasures in the main folder being captivating enough. This is where I worked out something that shook me even harder than anything I had found out about Jake in the last few hours. The folder contained all the pictures that Will had made available to me in our chat sessions. And that folder was in the "me" folder, not the "gaydar" folder where I, and a dozen of other, unsuspecting men, had all our intimate body parts and public appearance saved up for Jake's personal pleasure. Will was Jake and Jake was Will. Will never actually existed, the pictures used had probably been taken from anywhere on the web. Find a few pics of a guy and you can build on online profile.
I instantly shut off the laptop. I felt dizzy, upset. Jake had seen me naked, had read my wildest thoughts and fantasies, had had me jerk off for him, had made me take a picture to capture the moment. And since then, Jake had politely greeted me at work every day, shared a couple of smoking breaks with me, casually chatted in the hallways, and had offered me to housesit his place.
I stood up, went to take a jacket in Jake's drawer, and tried on one of his pairs of sneakers. His feet were obviously bigger than mine and I felt like I was wearing clown shoes. I kicked them off and put on my own old pair of Stan Smiths. I grabbed my ipod and the keys, and left the apartment in a hurry. I put on an old Tom Waits album, set the volume to very loud and started to walk, with no clear sense of direction or intent. I just needed to walk, to be on the street, with real people surrounding me, going about their business on a cool autumnal Saturday night in Boston.
I felt manic, I couldn't sort through all the conflicting emotions running through my cluttered brain. There was anger, a sense of betrayal, spite at his pathetic cowardly behavior. There was also lust, undeniably. Jake's own naked pictures kept flashing in my mind. Lust and anger must have converged at some point, as I found myself thinking about all the ways and positions I would angry-fuck him one day, debase and defile him as dirtily as I could.
None of this made me calmer – it only ended up making me slightly hard again. When I realized I must have been walking for almost an hour (the Tom Waits album had started back some tracks ago), I sat down on a bench, closed my eyes and for the umpteenth time that day, took a deep breath. This had been an insane day. I became aware that I hadn't eaten anything, apart from that sandwich a while ago. I had spent the whole day obsessing about a guy, sneaking on him, driven purely by lust and a not entirely healthy fascination for him. I had rummaged through his things, snooped in his computer, trying to construct his sexual identity, tastes and quirks. I was even wearing his own underwear and t-shirt.
I wasn't behaving much better or much worse than he had. There were differences, many of them that I could self-righteously bring up in my internal nagging monologue. But I suddenly felt too exhausted to think about it any longer and at peace enough with our awkward, messed up little dance. I just wanted to go home and sleep. Home was Jake's place, however comfortable I then felt about that, so Jake's place was where I dazedly walked back.
I took out my jacket, didn't shower, didn't eat. I just gulped half of a beer can, kicked off my shoes and lay down on the couch. I couldn't be in Jake's bedroom, not while it was night, while it was just as I'd left it, just as it appeared on Jake's pictures of him jerking off. I needed to be in the other room, the one with the New Yorker and Sports Illustrated, the one with the video games and "Raging Bull". I dozed off surprisingly quickly and slept like a log.
* * *
I woke up before dawn. My body ached a bit and I was starving. I took a long shower, which seemed to bring me back to life and to some degree of clarity. I went to Jake's bedroom to grab a pair of his underwear. I realized, first, that I was now doing this automatically and would probably be using them until I leave and, second, that being in Jake's bedroom didn't bring back any mixed or angry feelings similar to those of the previous night. I took some time to look again at all the objects, frames, pictures, and furniture, to bring back a fuller, more real picture of the actual Jake, the one I knew and liked, the one I saw at work and on whom I probably have had a crush on. I went for a walk, got a double expresso at Starbucks, and enjoyed the rising sun under a crisp dark blue sky. I loved this city, I felt energized and content.
I came back to Jake's, sat at the kitchen counter and turned on my computer. I looked online at the Globe, the NY Times, The Washington Post, and the Los Angeles Times. I thought about Jake, briefly, thinking he was now settled in Sydney, probably soon headed to bed as he was about 15 hours ahead over there. I was surprised and a little amazed that thinking about him was starting to make me feel horny again. Yet it was quite usual, actually, for me to feel horny on early weekend mornings, rested and jazzed up by two shots of espresso. A quick wank in the shower was a common start of such days. I had already taken a shower, though, but I felt a tugging inside that led me to log in to gaydar. The events of last night had, among other things, brought back some of the feelings of excitement that were part of my bouts on the site. It had been a while since June, and I felt curious to see if anything was happening so early on a hooking up site.
The site showed the number of guys online – that number was, as expected, much lower than when I usually logged in. It also showed whether guys whose profile you had bookmarked were online themselves. I bookmarked a lot of profiles, either because they caught my eyes and I may want to chat them up some day, or because I actually have chatted or hooked up with them. Three bookmarked guys were online. One of them was Will.
It startled me of course; I was not quite ready to plunge back into that Will/Jake mess. I cursed myself for logging in in the first place. Yet, I wanted to do something, I couldn't bring myself to just log off and get on with my day. I knew I didn't want to confront him either, not quite yet. So I chose to do nothing, to stay logged in, to force myself to wait at least fifteen minutes before doing anything. I cleaned up the apartment a bit; in less than 24 hours, they were already mugs, plates and beer cans, clothes and shoes scattered everywhere. I went to smoke a cigarette on the balcony. The sun was now fully up; it must have been 10:30pm in Australia. I was perplexed that Jake would already be logging in on gaydar on his very first night in Sydney. He was a horndog, I guessed, which yesterday had been a formidable turn-on.
I knew what I wanted to do. I took my computer to his bed, sat cross legged in front of it, and typed a message to "Will", just saying "Hey – how've you been?"
I got an instant reply. "Hey!! It's been a while".
After we'd established we've both been doing fine and that, yes, it was very hot chatting together earlier that summer, I asked him what he was up to so early in the morning.
"Not much. I'm just chilling. You?"
"You at home ?"
I had to try something. "Nice how overcast weather makes you want to snuggle at home, right? " The weather was bright and shiny.
I decided to quicken the pace a little. I told him I was housesitting a friend's place and was having a great time.
It seemed to take him a little while to answer. Maybe he was chatting with some other guy on a different screen, maybe he was taken a little aback.
"Oh yeah? How so?"
"I've been jerking off constantly since I got here yesterday. I haven't left the place, just constant wanking."
"Hot. You're making me hard," he typed back.
He had been, in our two previous sessions, more eloquent. More proactive too in steering the conversation towards questions and areas that seemed to get him off.
"Who's the friend?" he then asked.
"Someone from work. Nice guy. Hot"
"Nice. So what got you all worked up?"
"I dunno. Just being here i guess. Among his stuff."
"You into him?"
"I am now."
"But not before?"
"I feel like I know him more, staying here. Hard to explain."
"Let's say he has interesting porn on his computer."
There was a pause again. Was he thinking about what to say next? Deleting his first attempt at an answer? He couldn't possibly be chatting with someone else too at this point.
"You looked inside his computer." There no was question mark. I felt it was significant, but couldn't tell precisely why or how.
"He knows stuff about me, it only seemed fair"
"What does he know about you?"
"That I'm gay. I'm fairly open about it"
"He never said. But his jerking off habits have some story to tell."
Another pause followed, which irritated me as it dragged on. I wasn't sure exactly where I was heading and I guess I had been hoping that he would be steering me in some kind of direction. Instead, he only seemed to want to know how much I had learned and what my reaction was. I wasn't sure I had any reaction left at this point. I just wanted something to happen. Anything.
I decided to go smoke a cigarette outside. I could make him wait too, I wasn't going to give him any upper hand and just wait there, in front of my screen, for Jake to decide when he would grant me a response.
When I came back to my computer, three lines were blinking.
« So his porn made you into him ?
Are you still there ?"
"Yes," I replied. "Sorry. Just had a smoke in the other room."
« You smoke inside ? »
I smiled. He had told me on the drive to the airport to refrain from smoking inside and use the balcony instead.
"Yes. It shouldn't smell by the time he gets back."
"How many times have jerked off ?" he typed after a pause.
"Three times yesterday." I thought I should spice it up a bit by adding one orgasm to my list. Besides, I probably would have jerked off one last time before heading to bed – if I hadn't found the pictures of me.
"It's very hot that you jerked off in his room."
"It was. It was fucking awesome. I also jerked off to naked pics of him I found. Shot the biggest load."
Another pause on his end. I knew whatever he replied next would decide much of the rest of this conversation, possibly the nature of my future contacts with him.
"What were you thinking about ? when you jerked off"
"What I would do to him and with him."
"I would undress him, while I keep my clothes on. I would touch him, caress him, hold him. I would bring him to my crotch, pull my cock out of my pants and have him blow me."
"I would fuck his face. Then I would kiss him. For a long long time. I would bring him to the window, have him face the street, hugging him close and tight from behind."
"I would kiss his neck, pinch his nipples, hold him very tight."
"this is hot. U make me hard."
"Then whip your dick out and start stroking."
"done," he typed after a short pause.
"Then I would spit on my fingers and wet his hole. I would slowly push my hard dick inside him, just the head at first."
"I would slide out just a bit, then push back in. I'd repeat that a few times, until he is ready for me."
"so hrd right nw"
"Then I would push all the way in and start to pound him. I'm still hugging him tight, his face is pressed to the window."
"I would take him to his bed, have him lie on his back, raise his legs and hold his ankles. I would watch him while I slowly finally undress for him."
"Then I would start fucking him again. In and out. Real hard. Always staring at him while he stares at me."
His replies were getting shorter, a telling sign that he was jerking off. I was incredibly horny, thanks to the vivid fantasy I was describing, to the fact that it was turning him on and thanks to his jacking off with me all the way in Australia. My cock was really hard and I had to stroke it.
He wanted more. I was torn between bringing him to climax and jerking myself off, which would keep me from the keyboard. I decided to let him know of my dilemma.
"then jerk off w me", he typed. "i can picture u, i can picture u fucking. V HOT."
"I don't want to cum just now."
"I do. so fucking horny right now. j-o w me. CUM w me ».
"I'm jerking off. Thinking about you."
"about me or about ur friend?"
"I'm jerking off and it feels fantastic."
Nothing much then happened on the screen, as we were both jacking our dicks – quite furiously on my part. The naked pictures of him, his body, his dick, kept flashing and knowing that he was right there with me was quickly sending me over the edge.
"gonna cum soon," I managed to quickly type.
I erupted, spraying my t-shirt and gasping a bit. "I just came", I typed with one finger.
After a while came his reply : "Me too. That was great." This was when chats usually ended – often quite abruptly. I didn't know what to do. Post-climax, I didn't feel the energy for a confession, nor a continuation of this cat-and mouse game. Nothing came from his end, but he didn't sign off.
I just typed « Good night, Jake. Enjoy Sydney. xo », then slammed shut my computer.
The whole thing barely lasted twenty minutes. My previous two chats with « Will » had lasted close to two hours each. There had been intense build-up, elaborate stories or fantasies described minutely, pointed and piercing questions. This morning was, comparatively, a quickie. It felt like a let-down for a minute, but I came to think that this was the climax of six months' worth of foreplay between us. He had been fantasizing on his own about me and I had grown (albeit kept in check) an attraction towards him. We both had jerked off thinking about and engaging somewhat with the other, him as Will last June, me watching his pictures last night. Now we had jerked off together, finally – and a bit underwhelmingly.
I actually felt like I had gotten something heavy out of my system. I had no idea what would happen next, on my part or his. But my head felt clearer and my mind at peace. I texted Charlie and Chuck and we ended up spending the day together, walking and lounging in Franklin Park. I did tell them everything about the strange last 24 hours. Charlie was mesmerized, Chuck was giggling like a teenager. I promised to keep them abreast of any further developments.
There weren't many. It had occurred to me that Jake could choose to stay in denial. Pretend that Will was Will and Jake was Jake. And this is what exactly what he did. Having heard nothing from either personas after two days, I sent Jake an email casually asking him if he was settling ok in Australia, and I logged in on gaydar to check for any news. There was a message from Will, which said Hey there. Great chatting with you. Very hot. Hot for u 2 i guess, cos you sent off mixing my name !! is jake your friend ??? hope to chat some more soon. Jake replied to my email saying that indeed, all was well Down Under and that he was looking forward to four weeks of clearing his mind.
Charlie and Chuck seemed to be convinced that I had gotten things wrong. I myself wasn't sure any longer. But as the days passed and nothing else happened, I started to care less and less. I couldn't find in me to chat with Will and play Jake's game. In the end, he was a nice guy, confused and conflicted. Formerly straight, probably, but still slowly cracking open the door of an obfuscating closet. There is always collateral damage in these circumstances and I saw no joy in being part of that. I did wonder at how the pictures he had chosen for his fake Will profile showed someone who looked nothing like him, a short, bulky, blond guy. "Will" actually looked a bit like Jake's surfer friend on his beach picture. He was probably working through some issues ("He's on journey!" Charlie once quipped). And I did feel a pang of guilt and curiosity at the fact that I was more attracted to mystery Jake from work or to masturbation addict Jake, than to confused and repressed Jake.
Jake came back at the end of the month, we exchanged niceties. It was cordial; Jake, as before, displayed his strange mix of aloofness and flirtation. I, as before, kept my polite, smiling distance. We barely saw each other at work; he might have been avoiding me or I was paying less attention. I went to live with Charlie, who was ecstatic to have a roommate ("Just like in college!"), and happily stayed with her for eight months, until I left Boston.
I did, and still do, wish the best for Jake. It does turn me on to think about him from time to time, and I confess I've jerked off quite often to his pictures in the following years. I had copied them all from his computer on a flash key, just before deleting all of mine.
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