First Time Watching

The first time to explore my sexuality with a guy came when I watched someone … looking on a dating site for a meetup that would be erotic but not necessarily sexual wasn’t easy.

But after some searching, I came across something new to me: a guy who offered to let someone come by and watch him masturbate. He had several photos of him stroking away in different poses: totally nude, totally hard, and totally huge. I liked the ad because he wasn't looking for sex or even suggesting it. I just wanted to watch, as a voyeur, I guess, without realizing it. So I sent him a message. I explained what I was interested in, and that, specifically, I was intrigued by someone slim like him (and me), who was well endowed (not like me). "Yep, that's me," he wrote back. He was also a book editor, so adept with words too. We made an appointment.

We arranged to meet one evening. I went over to his neighborhood, and he was there waiting in front of a store just as he said. We introduced ourselves, and he invited me up to his apartment. He had told me he wasn't much for getting a coffee/beer/drink in advance, and that was OK with me. I was plenty nervous, never having seen a guy naked and aroused before. I mean, I've been in locker rooms regularly, around naked guys every time I go to a workout.

But never had I seen a guy hard in person, and certainly not a guy whose pictures showed he was truly hung.

So we got to his place and he quickly showed me around. He was indeed tall and slim, like me, about 6', with a 30" waist, fair hair and glasses like me too. Reserved, but like a lot of reserved guys, wicked smart.

He was great at putting me at ease with a little small talk. He took my coat, took off his, and offered me a glass of water. Then he took  off his shirt and ski pants, and was in nothing but his white boxers. He said he liked to get a little hard before getting naked. I just nodded.

I sat down on his sofa as he started stroking over his underwear. Soon enough a bulge grew, and then he slid off that last layer of cotton to reveal a plump cock. It was still pointing down, but thoroughly tumescent, and he caught me staring. "That's OK, it's what you're here for," he told me.

He kept working his cock and within minutes it was at full size: easily 9", as thick as my wrist and pointed straight out. He walkedover to me so I could see it up close ... transfixed, all I could think of to say was something like "Man, that's really big." Original, huh? But he was totally cool. He's probably used to jaws dropping and words failing.

"Do you want to feel it?" he asked, and I said I did. He put his hand to his side and let me have a go.

The first thing I remember thinking was how warm it was—which is strange, right? I mean, I had stroked myself plenty and knew what to expect in that sense. But feeling another guy's cock just made the experience more real, I guess.

Next I noticed how hard he was. There was a lot to grasp, thanks to his girth—with my fingers wrapped around him my thumb barely touched my index finger. He was just solid, like most young guys' cocks, I would guess, but it was more noticeable with a big one. I started tugging, then worked him a little harder. I put my other hand on the rest of his cock to stroke more of him, but still there was an inch or two free.

I couldn't take my eyes off that thing. It's like a salami, I thought to myself. He noticed I was lost in my thoughts. "Do you want to undress?" He asked, but I declined as politely as I could. Never having done this before I was fairly petrified.

I relinquished his cock so he could give it the attention it deserved. He stood in front of me, and walked around a bit, then askedagain if I wanted to take my clothes off. Again I thanked him for the offer but said no.

One of the images in my mind is how disproportionate he looked. He was as lean and fit as I was, but his cock was as large as a beefy porn star's. I completely admired him for that, though I don't think I'd want one nearly that size myself.

"When did you first realize it was so big?" I wanted to know. He looked at me and sorta shrugged. "It's just always been there," he told me.

After a while he was getting close. "Are you ready for me to cum?" Of course I was, so he sped up his stroking and within a minute exploded several nice bursts of cum all over the floor. When he caught his breath I told him how excited it had been. He was nonchalant: "I've never had a bad orgasm."

I forget how we ended the evening, but I remember that I went from his place to my girlfriend's. Too nervous to mention the show I'd just seen, I did ask her about her boyfriends' sizes. She was very open about sex and thought nothing of the question. She'd had one guy who was 9" long, "but it was painful," she admitted. She and I had great sex together, and we did that night too.

Within a few days the Big Boy emailed me and asked me to come over again. I was up for it, so I went to his apartment. But this time I knew I was ready for a little more.

He invited me in, took my coat, and asked if I wanted some water. I did, and as he was getting it I took my jeans off. The chance to show off, for the first time to a guy, had me so excited that when he turned around with the glass he could see I was already fully hard. Two-thirds his size, but still.

He undressed to his boxers, and I took my shirt off. We sat down next to each other. He pulled my tight boxerbrief down and started stroking me. It was an amazing feeling. Not just the handjob. Girls had given me those before, and I'd never had a bad one. Having a cool guy with an astounding attribute do it for me was incredibly erotic. So erotic, in fact, that I lasted an embarrassingly brief time before making a mess of the two of us.

But the release was an opening for me: I had shared an intense and vulnerable physical moment with a man. It was a direction that I would soon explore regularly.

After I helped him climax, we said our good-nights. Remember, I was still so new to this that I was more nervous than anything. Looking back I wonder what would have happened if I'd just told him how anxious I was and explained that he was the first guy I'd j/o'd with. But I didn't, and soon I would be stroking with others ...