Like the title suggests, this is what happened during my first time with another guy. It's the first time, not the only time, so let me know how you liked the experience, and I'll tell you about some of the others I've had.
Several months ago, I finally conquered my fear of doing something I'd wanted to do for several years now, jerk off another guy. It happened in a local park, in one of the picnic shelters. I'd been 'instant messaging' with this man for about a week, and we both decided to meet in person once we felt comfortable enough to do so. We were both married and sexually neglected by our spouses, and most importantly, we were both curious to try mutual masturbation with another man.
I got there first, mainly because I just knew that if I had to approach him, I'd chicken out. This way, he'd have to make the move. After several minutes of battling the urge to turn and go home, I saw his car approaching in the distance. My heart began beating so fast and so hard, I started to get a bit light-headed. I also began to feel my cock starting to twitch in my shorts. He drove up and parked beside me, waving and motioning for me to join him in the shelter. We exited our vehicles and walked towards the shelter, barely able to make eye contact and making small talk. I could tell it was just as awkward a moment for him as it was for me. We found a darkened corner of the shelter with a window to the parking area, so as to keep tabs on others in the vicinity.
We chatted nervously for a minute, then began talking about how we were feeling about what we were about to do. He told me he'd been driving with a hard-on the whole way, and I reached over and felt how hard he was. It was a bold move, but one that broke the ice and got things rolling. He stood up and let me work his cock out of his fly. He wasn't wearing underwear, so it was easy to free his cock from his shorts. We talked very little, other than to say how great it felt to stroke him and how great a job I was doing. His cock did feel awesome in my hand! He was maybe seven inches long and was quite thick in the shaft, with a bulbous mushroom head on it that started drooling precum almost immediately. He told me how he liked to be stroked, and I was a quick learner. In fact, he was just like me when it came to masturbation, slow rhythm and gentle touch. I had him groaning in no time, but just as I was about to finish him off, some kids rode up towards us on their bikes. My friend quickly righted himself, and cursing the boys, he started to walk out of the shelter. He quietly asked me if I'd be interested in renting a room at a local motel so we could be left alone to do anything we wanted to each other. I told him I would join him, and we proceeded to get a room for a couple of hours.
Once in the motel room, we couldn't get our clothes off quickly enough! I could plainly see the rather obvious wet spot his precum had created in his pants. Once we got naked, I suggested we take it slow, to build up our orgasms to a fever pitch. After all, both of us liked a gentle touch. After some gentle massaging of each other's cocks to get them fully hard again, we knelt on the bed, facing each other. We let our legs rub up against each other. While we did this, we began gently stroking each other's nipples with our fingers. I knew how much this turned me on, but I didn't know until then that my friend loved doing that, also. In fact, he told me his nipples were so sensitive that he was able to bring himself off just from nipple play, and without any direct stimulation of his cock. I told him I'd done that several times, too! This guy was turning out to be just like me in the way he liked to masturbate.
After doing this for a while, we'd worked up quite a pool of our precum on the sheets. I was totally turned on by his dripping cock, and even tasted some of his precum. I asked him if he would be able to reach a no-hands orgasm, and he told me he had been fighting his climax for the past several minutes. I laid on my back and had him mount me so that he straddled my chest. He leaned his upper body forward and held onto the headboard, and I reached up and began tweaking his nipples once again. He closed his eyes and began moaning and gently bucking his hips. In about 30 seconds, I had him right on the edge of his orgasm, and he asked if I wanted his load on my face. I was so into it, I begged him to spray my face with his cum, and with that, he arched his back and growled that he was cumming.
His first three ropes of cum flew out of his cockhead with so much force, he plastered it across the headboard. His cock was flopping up and down with each spasm of his orgasm. The rest sprayed onto my face and neck. He collapsed on the bed beside me, all out of breath, and I popped up and assumed the mounted position over his face, thinking he'd do me the same service. I had hardly gotten into position, when the first globs of my cumload began oozing from my cock. I hadn't even started my orgasm, yet! I'd had this happen before, where I'd ejaculate some cum before ever reaching a climax, but never to this extreme.
He reached down and grabbed my shaft and began stroking it, and I couldn't hold back anymore. I closed my eyes and let the orgasm race through me. The feeling was so intensely strong, that I fell onto my friend and involuntarily began humping against him. Thirty seconds later, it subsided, finally, and I rolled off of him. The cum had been sandwiched between our bellies and cocks, and when I fell back, it formed bridges of white between us. I couldn't believe the mess! What an awesome orgasm! We even laughed in amazement.
He told me that this was the most fun he'd had sexually in his life, and I had to agree. To this day, I've never been as turned on as I was that afternoon. I had fantasized about what it would feel like to masturbate with another guy, but the real thing was far better than anything I'd imagined before. Since that day, the two of us have had several more masturbation sessions, and have even invited some other guys to join us. I'll tell you all about those sessions, if you want me to. Just let me know.