A Bi-Sexual Man's First TimebyAmatoriuS©
My story starts with an adult dating site. I had a profile there looking for men for a while, but had no joy aside from the occasional man in his later years. Ideally, I was looking for a guy in his 30's or 40's to be a bit dominant with me. To cut to the chase, I forked out the extra cash to make my profile more noticeable and put up some pictures that I'd had in the Lit amateur section. That helped me to get a lot more contacts and finally one from a guy around 34 who lived really close and worked quite close by too. We sent text messages to each other every day for a few weeks just to break the ice a little, often talking about how much I wanted to suck him off and how much HE wanted me to suck him off. (It came about quite early that I was the bottom.).
Then one afternoon he said he was mere minutes from where I work and that we should meet up when I got off just to say hi with no pressure. I agreed but got some last minute jitters and almost didn't go, nevertheless I walked up to the place we'd agreed to meet. We'd sent a few text messages confirming what the other would be wearing so we could spot each other in the crowd. I looked for him and eventually spotted him dressed in his business suit--he looked quite nervous
I stood about for a while trying to work up the courage to go over to him as he hadn't spotted me yet, but eventually he did spot me and, with a big grin, started to walk over to me. We said our awkward hellos and laughed at how shy we both became in reality after our sordid text messaging. He suggested a local pub where we could get some booze to calm the nerves and I agreed. So we walked for a bit in more awkward silence that was unbroken aside from the occasional comment about something or other entirely unrelated to the reason for our meeting.
When we got to the pub, he bought me a drink or two and the ice starts to melt between us. We were at a corner table and he sat facing me with his legs spread in a real masculine pose. I was able to see that he was pretty damn aroused. Apparently, he was wearing some really loose boxers so his cock was totally free to roam--and roam it did. It was positioned against his thigh pointing straight at me. He knew I could see and that I was looking and he kept shooting me a really confident grin. I had to adjust myself more than once. The conversation got more and more daring the more drink we consumed and the busier the pub got so that our lurid discussion was drowned out.
There came a point in the discussion when I brought up that my flatmates were away and the conversation shot down a path suggesting that we make use of my empty flat. Before too long, we were grabbing our things and heading there to do just that. Outside the pub the conversation went less sexual again and a little awkward as the night air sobered us up but it was safe to say we were both still hard when I put the key in the door.
I had a quick run around the flat to make sure everyone was out and came back to see him sitting on the couch with that same grin though minus his trousers. All my nerves left me at that point but I went sat next to him anyway--immediately grabbing him through his boxers. He kissed me, which was a surprise as he'd mentioned nothing about that before. I'd kissed a couple of guys before but never while I had my hand around their cock--this was a whole new game.
He broke off and looked down at my hand as I pulled him free. I don't know how but he was a lot bigger than in his pictures--longer than me by a bit but quite substantially thicker and veiny. It's an understatement to say I was pleased. I started to stroke him and it was exactly how I imagined--there's a weird sense of power when you're gripping another guy's favourite appendage. I stroked him for a good few minutes and we made amusing conversation about how odd but good this all was.
I'd totally lost all interest in my own cock and my own pleasure but he reminded me he was after the same thing so we agreed to move to the bedroom and get totally naked. He already had his boxers off so I got to watch him walk in front of me with a lovely toned butt which I was tempted to slap. Although I refrained. He stripped off the rest of his clothes quite quickly and I saw he had a great physique. He'd mentioned earlier that he was a rower so he had a really good upper body definition. This made me feel a bit embarrassed, because while I'm not chubby, I'm not exactly toned either
He seemed quite pleased with me, though. And when I stripped off myself and pulled down my own boxers to let him get a good look at me, he reached forward and put his hand on my cock. A younger me would have shot off right then and there, but I stood my ground and we climbed onto the bed. He half jokingly, half dominantly said "Get to it then" and stretched out with his hands behind his head. It was quite a funny pose and if I hadn't been so turned on I think I might have broken into laughter, but I'd had this fantasy for about as long as I'd known what to do with my penis and here it was in front of me. So I reached down and gripped his cock in my hand and straightened it up--it was quite an imposing penis and if any body part could look angry it was this wide old fella.
Nothing had really prepared me for the feeling of that first moment you feel the sides of a cock on your lips, I think I must have held it there for a while savouring it. The taste was mostly what I expected--a little salty and almost a bit sweaty. That isn't the best sounding taste when written down but in the context it was good. I felt a hand on the back of my hand and knew it to be the universal signal for "deeper" so I tried to get a bit more in. Now I don't have the best gag reflex in the world, so I tried taking it in a more diagonal angle--pushing the head against the inside of my cheek. He was groaning now so I took that as a good signal and it felt good feeling his smooth head pushing out my cheek.
Once I'd found a happy depth I started to move my head up and down in the way I'd seen previous female partners do. I became aware of my own cock again and swiveled around a bit so he could get his hands on me, allowing him to start jerking me off. He had a nice upward curve to his cock and the angle I was at was working really well, REALLY WELL. The head of his cock had been getting some good friction from my cheek and the shaft a fair bit of tongue and lip action. He told me he was about to cum and before I had any chance to either move out of the way or point his cock down my throat he was cumming all over the inside of my mouth. I'd tasted my own cum before out of curiosity and his was pretty much the same though there was a lot more than just a drop on the end of a finger. I started as I meant to go on and knelt up and swallowed uncomfortably.