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The First and Only Time

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About the First and Only time I watched another guy masturbate.


The first and only time I've watched another guy masturbate:

Although I've witnessed several girlfriends masturbate themselves to orgasm in front of me, almost always at my request, only once in my life have I witnessed another man take care of himself. The best part was he didn't know I was watching him at the time!

It happened three years ago. Back then, I was living in a two bedroom apartment near down town. I had a room-mate, but he was rarely around, and when this all occurred, he was out of town for the week.

It started Monday night. I was in my kitchen, I had made a late dinner, and was cleaning up, putting the dishes in the dishwasher, being late, and as far north as I am, it was already quite dark out. In the part of town that I live, the buildings are quite close together; consequently, the apartment building next to mine was only about ten feet away. The small window in my kitchen looked onto the side of that building. I realized as I was taking care of the dishes that I could see right into the bedroom window of the apartment directly across from me. The lights were on, and I could see a desk, a small dresser, the closed door, presumably to the rest of the apartment, and an open sliding closet door, the closet being stuffed to the gills with clothes. There was no bed visible, but I would know in a few moments it really was a bedroom.

In truth, I paid little attention to the window, and the room beyond it. I don't remember exactly, but my mind was elsewhere, paying little attention to what was around me. Then, suddenly, out of the corner of my eye, I saw motion. I looked up at the window and across into the next room.

A woman had walked in. I turned to watch. I realized that from where I stood, across the kitchen floor, out the window, through her window, she could be no more than fifteen or twenty feet apart from me. I also had a second thought, being that if I could see her this well, than she could certainly see me too. I back-pedalled a few feet behind me to the wall, reached for the light switch, and shut off the lights. There. I was in darkness, and now I took a moment to check out this sort-of neighbor.

I'm not an accurate judge of height, but I'd say it was average. She had long, thick blonde hair, several inches past her shoulders. She wasn't crazy thin, nor was she excessively overweight, just typical. In fact, at first glance, most of her seemed typical. She had her back to me most of the time, but I did get to check out her ass, which looked very nice-again, it didn't stand out as too round or too flat, just curvy enough to please me. She was wearing blue jeans, not too tight, but enough that I could tell she had long, well defined legs. At last she turned around; she was still talking on her phone. She was wearing a tight red turtle-neck, and her breasts, through the shirt, looked about average.

I had initially thought of turning on the lights again a moment later, but as I continued to watch, I became fascinated with her, and the fact that she appeared utterly unaware that I was only feet away from her at watching. I never considered turning them on after that; and the dishes were forgotten for the rest of the night. As I watched her, I realized she was engaged in domestic chores that night too: she was folding laundry and trying to stuff them in her closet. The whole time she kept talking on her phone, wedged between the side of her chin and her shoulder.

How long did I stand there? Probably a good half hour. At long last, she turned out the lights and the show was over. I was hooked. For the rest of the evening I kept returning in the dark to that window to see if she was back, but no dice.

Tuesday night, the next day. Same routine. Washing dishes again late, as soon as her room light went on, mine went off, and I stood in my kitchen watching. Again on her phone, she sat at her desk, and idly flipped through a book as she talked. Tonight she only talked for about five minutes, and then-jackpot! She walked over to her closet and pulled out some clothes that were on hangers and tossed them on what I assumed was her bed, but I couldn't quite see that far to that side. She peeled of her shirt and draped it on the desk chair. Holy sh**! Her breasts were larger than I initially thought, probably C's, but I'm not exactly the best guesser of all those letter sizes anyway. They were in a very lacy white bra, actually quite modest, but the thrill of it for me was enough that I could feel my penis hardening in my pants.

Then, with her back to me, she peeled off her pants, and wowee! She was wearing a red thong, and I could see her whole pale, yet shapely ass! Curvy, yet not too large. She proceeded to prance about her room for the next two minutes in this glorious state, and I soaked it in. She walked back to her desk, picked up the phone, talked on it a few moments-no answer?-and set it back on the desk. Then she walked over to the opposite side of the room, and was out of sight for a few seconds. Returning back into view, she was buttoning up a shirt, but her bare legs were still exposed. My penis was now as hard as it had ever been, and could feel my heart rate go up as I watched this beauty. Out of sight for a few more seconds, she appeared again, clad now in a pair of khakis. I realized my show was winding down. Walking out of the room, I saw my show was over.

She would come back! I told myself. I ran to the dining room, grabbed a chair, and placed it a few feet from the edge of my window. I sat in it and patiently waited for her to return. I don't think I lasted more than ten minutes before boredom overcame me, no doubt partly due to my heightened arousal. I slinked off to my bedroom, at watched TV for the next few hours, stealthily returning in the darkness of my kitchen to check and see if she was back every commercial break.

One thirty a.m.: she was back. This time, she had a guy with her, whom I quickly found out to be her boyfriend. As soon as they were in the room, they hugged and began to kiss. I sat in my chair and began to watch. For what seemed like the longest time, they just seemed to stand there immobile, faces connected, and that was it. I started to look around a little more, and realized that she had her window open. Hmmm, I thought. This presents some possibilities. Slowly, and cautiously, I began to slide my window open as well, being careful to do it only when I wasn't in the line of sight of either of them. I figured that although I wasn't illuminated by anything in my apartment, the bright ceiling light of her room might make me stand out if I got to close to my window.

Then things progressed quickly. His hands began to roam up and down her back, and eventually he cupped her ass cheeks. She wasn't so frisky, but the kiss was finally broken. She said something to him quietly, but it only came as a mumble to me, and then he walked toward the bed out of sight, and she walked out of the room.

Would she come back? Oh yes! Less than two minutes later she came back into the room. She turned on a smaller lamp on the desk, and then killed the bright room light. In the lower lighting, she seemed to pace in and out of sight, but she was slowly stripping. Off came her shirt (a black bra tonight), and then her jeans (matching black undies, the kind of boy-shorts style, I think). I was hard again. Very hard. I saw her one last time, without the bra, but her bare back was to me. Wonderful! Then she was again out of sight in the other corner of her room. I waited, hoping to see her again. I was so aroused and excited. I waited a minute, then two. Now maybe three. Wanting to stay this happy, I stripped of my pants and boxers, pried my shirt off my head. Naked in the chair, I slowly began to tease my hard-on, slowly rubbing the head, once in a while giving it a full-handed stroke up and down. I could come at any second. And I still waited. I decided I would stay, slowly keeping my penis hard, until that little lamp was shut off. So I remained for another twenty minutes.

Then I heard her. She was making small little grunting sounds, sort of like, 'uh, uh, uh,...Uh!' That really got me going. She kept this up for another five minutes, at the same pace, until she stopped, and then started occasionally making long breathing sounds, that were like, 'uuuuuuuuuuuhhhh, ah...uuuuuuuuuuuuh, ah....,' and so forth. Now I was outright stroking myself, furiously masturbating, pumping my hand up and down along my penis. Then I heard him, a long, low, deep, guttural moan, which gradually got louder and faster. Wow! In a few seconds, her sounds ceased, and he his groans began to increase in pitch, and then there was one, last, long one, and it was all over. I guessed they were done, and, already right at the edge, brought myself over into orgasm-land, squeezing hard the base of my penis, my hips flexing forward, and my cum quickly spurting itself onto my lower stomach, my hand, my balls, and the front of the chair. Oh, what a satisfying orgasm!

One last delight: I sat motionless in the chair for another few minutes, basking in the aftershocks of a powerful cum. I only half glanced at the window, but then I saw her! She was completely naked! She walked to the window to close it, and I took her all in. Her breasts were fantastic, not too small, with small nipples that were nearly as pale as her. Her hips were well-defined and fairly wide, the kind that I always enjoy on a female. Her pubic hair was-oh her pubic hair! Untouched by scissors or razor, it was a blonde shade, slightly darker than her head, very thick, bushy, and curly. Her pussy was obscured by this tangle of luxurious hair, but I didn't mind. With the window shut, she turned, and I got one last look at that fantastic ass, before she shut off the desk lamp and all was dark once again. I sat in the chair, reliving in my mind all that I had saw. In what seemed like no time at all, my penis was hard again, and with my hand, using my own cum as lube this time, I pounded out another satisfying cum. Not quite the prodigious spray of semen this time, it bubbled out and ran down the shaft, over my fingers and balls onto the chair. I finally got up, cleaned myself (and the chair) off, and went to bed.

Wednesday. During the day, at work, I had to tell someone what I saw. I confided in the ardent lesbian in our office, Courtney. Although committed to women, she had in the past enjoyed relating the lurid details of her sexual exploits to me when we had quiet moments at work. I think she got a kick out of knowing I was turned on at work. She was also a proficient and frequent masturbator, as was I, and we had discovered this in a very whispered conversation the previous spring at a bar with us both far to drunk. When her conquests of women hit a dry spell, she would often start a private conversation to me with, 'Oh, man, I gave myself a whopper of an orgasm last night. Just soaked the sheets.' And then proceeded to describe every moment of it to me, watching me squirm and attempt to hide the obvious erection in my slacks.

As soon as we had a second alone, I related to her, in exactly the same level of detail as she had to me, what I had witnessed the night previous. I even used the crass words she so often enjoys, like 'pussy,' 'tits,' 'ass,' 'dick,' 'horny,' and 'jacked myself off.' In response, she responded with one sentence, in the manner that I often spoke of such things: 'Oh, If I had been there I would have had my pants down and rubbed my clitoris and masturbated!' We both laughed. 'So,...did you?' she asked. I lied and told her no. I was still a bit shy at this point.

That night, at the appointed hour, I had my chair set up, I was naked, and waiting. But there was no show, at least not from her. I sat for an hour and waited to no avail. I was really bored. I considered going back in my room and watching TV again, and occasionally checking, as I had before, but then I realized something. Hers wasn't the only apartment with open windows and lights on that I could see. I looked around. Most were to far along the side that the angle just wasn't right, and a few were so many floors above me that all I could see were ceilings, and some had closed drapes and blinds. Maybe this wouldn't work so well. Then I looked down. In the apartment directly below that of the sexy mysterious woman, not only was the room visible, but I could see a desk and the entire bed. It was also at such an angle that I had more of a sort of 'birds-eye' view. And although the lights were on, no one was in the room that I could see. I decided to follow the same leave and check back procedure again. I diligently came back, checking the room directly across, and the one below it.

Then, at nearly eleven, I saw a guy sitting in the chair at the desk. He was reading on the computer. He had on dark blue jeans, a sweatshirt, and a Seattle Mariners baseball cap. From the high angle, the cap obscured the view of his face, nor could I get an idea of his height or size. But, I was still fascinated by it, and watched him intently for probably half an hour. Growing bored again, I returned to my room. Ten minutes later, I came back.

HOLY SH**! He had taken his penis out of his pants. It was huge. Well, I thought it was huge. It wasn't hard, only sticking out pointing toward the computer screen. His hand was underneath it, sort of cupping it, his thumb occasionally tapping the top of it. I think it was about seven or eight inches long, certainly almost twice as long as his hand wide, which for me, at the time, I thought was incredibly huge. My own member was five inches when fully hard, and so much less than that soft, and seeing his, at that size soft, I was fascinated. I pulled the chair closer to the window and watched intently.

He was watching something on his computer screen. I couldn't tell very well, but I think he was downloading porn movies from the internet, and it appeared he didn't have a very fast connection. He would slowly stroke his penis, his hand languishing up and down the length, as it slowly got harder. When a movie played, his hand would move up and down very quickly, much faster than I had ever tried to stroke my penis.

Speaking of which, I was very, very aroused. My own penis was stiff and ready again, my hand stroking it up and down with a regular pace. In a few minutes I knew I was close to cumming, so I focused on caressing the underside of my balls or occasionally just rubbed the head of my penis with the palm of my hand, just to keep me hard and close to the edge, but not actually go over until he had.

His penis, fully erect, really wasn't much longer than it was soft. I was thinker though, and a closer shade to pink than it had been before. He alternated between very fast, rigorous stroking, to pushing it down so it was parallel with the floor and slowly rub the underside of it with his palm.

I watched him, transfixed. How long exactly I can't say. An hour? Two hours? Maybe. To me, it was fascinating. I hadn't seen a grown-man's full-size penis since showers at the gym in college, and those were only fleeting glances, at a time when I thought I was clearly hetero and had no bi-curiosity yet. I was in a dream state almost, lusting after this guy, knowing nothing about him (for all I knew he was watching straight porn), wishing to be right there in that room next to him, side-by-side, stroking ourselves, and maybe I'd reach over and grasp that humongous penis and help him out, and he'd do the same and then....

Before long, still in my pre-orgasmic haze, I watched him finish. He began to pound his penis, up and down so quickly his hand was a blur. He sustained the action for maybe thirty or forty-five seconds and then abruptly stopped. I watched his warm, milky goo expound itself in four big globs, remarkably landing back on his hand and member. He quickly reached across his desk for some tissues, wiped himself up, and stuffed the monster back in his pants. I realized I had just ejaculated too, my arousal so built up and my pleasure so complete that drops of my cum had landed on my forehead, neck, left nipple, and stomach. Oh, what an orgasm! Oh, what a sight! More calm, satisfied than even the night before, I went to bed.

Courtney asked me at work if I had seen 'that hot chick frig herself again?' I told her no. Disappointed, she turned the conversation to other topics, and I never told her about watching that guy until some years later at a party at my apartment (but that, as they say, is a whole other story). I went home that night, and sure enough, he was there again, at his desk, playing with himself. I joined him for another wonderful orgasm that night, and again on Friday.

My roommate got home on Saturday. 'What's this chair doing in here?' He yelled from the kitchen. Thank god I had cleaned up my cum! I made some lame excuse about trying to retrieve an item from a high cupboard and returned the chair to its normal place. With him back, I certainly couldn't very well continue my nightly masturbatory activity in the kitchen, and had to confine them once again to my bedroom-alone. I never got to see either the woman or the guy in their naked or sexy glory again, but I did come away from that week with a new hunger.

A hunger for watching a guy in person jack himself off.



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