Jay Crosses The Line: The First Time

Despite my determination and progress, it wasn't until a couple of weeks after The First Move that I finally got to have my first time with a man. I had written several posts about my deliberations, my attempts, and my failures. I remember one or two readers commented something like, "Come on, just do it already!". And I mirrored their sentiments, I was beyond anxious to finally do what I had set out to do. But, as you can imagine, I was a bit scared as well.

 

With all the planning and thought that went into it, I was surprised by how spontaneous my first time actually was. I had thought about it for years. I spent more time than I am willing to admit planning and debating over the last few weeks and months. I had made several attempts, but failed each time to follow through. Then one morning in July, I received a text asking when was I going to come over, and I realized then and there that the only way to make this happen was to just do it. Don't worry if everything is planned out right, just do it.

I responded to the text with "When do you want me?". This was a guy that I had been texting with for a week or so. I first found him on Grindr. I knew he was a bit older than me. I didn't know a whole lot about what he looked like, but I didn't care. All I cared about was playing with his dick, and him playing with mine. His response back was "Now!".

Now didn't work. But I wasn't going to let this sudden burst of courage go, so I suggested lunch time. At first, I don't think he believed me. Then he happily agreed. My heart started pounding, and it didn't stop until later that afternoon.

 

The whole experience, and the sex, had such an impact on me that it took 4 long blog posts to describe it even somewhat accurately. I had to write about my fear. My fear when I was driving over was so great that I had to circle the block several times before finally parking in front of his house. My fear when I was walking around the side of his house was so great that I was panicked this was all a hoax, or that I was at the wrong house and was about to get arrested for trespassing. I even, for a moment, thought about those "To Catch a Predator" shows, where a guy gets ambushed as he walks through the door. I knew I wasn't a predator, but the fear of anything remotely like that happening was almost overwhelming, almost.

When I reached out my hand to grab the handle of sliding glass door in the back of the house, I know longer felt in control of my own actions. I was in this surreal mode, where I was hovering just outside myself, watching my actions, hearing what was going on, but from a 3rd person perspective. I opened the door, still couldn't see inside because the blinds were drawn, but heard my name being called out.

I wrote 4 long posts about the experience, my fear going into it. How that fear melted away once I saw his cock. How his cock felt in my hand, it was the first time I had touched another man's cock. How his cock smelled, how it tasted, how it felt sliding across my tongue. This was almost two years ago, but just thinking about it now has me horned up and rearing to go. I wrote about my attempts to deep throat him, and how I discovered my own gag reflex. His cock was thick and long, hot to the touch, and like a steel rod covered in soft silk. It curved upwards, so I didn't slide down my throat the way I had imagined. I also learned that I needed a lot of practice giving head, I had no where near the stamina it takes to do it properly. I kept having to resort to using my hands.

I also wrote about having his mouth envelop my cock. That was not my first blow job, but it was the first from a man. Everything I had heard about men doing it better than women was proven in the first few moments. He expertly brought me to orgasm, let me come in his mouth, and sent electric shocks throughout my body when he didn't pull off right away. Even today, I am still not at his level in giving blow jobs. Now that I had passed this threshold, that I had "crossed the line", I knew that I was going to get plenty of practice in the future.