Author's note - This is a mostly true, if slightly abbreviated story. It may start a little slow but I wanted to make sure the scene was set appropriately on the lead up to this event. I hope you enjoy it.
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"Do you ever think about what it would be like to have a dick in your mouth?" At first I laughed when that message came through. I had never been with men and loved pussy but after the initial reaction I caught myself thinking that I wasn't as shocked at the thought as I would have guessed. I jokingly typed back, "Well we'll probably never know I guess, I could have been a natural cocksucker." I liked being the submissive and she liked to play off this conversation to make me describe what I would do if presented with the opportunity with another man or telling me to imagine it was another guy when she would tell me to push the plug in myself. The more she talked about it the more I realized that the thought didn't turn me off and that I really wanted to try. I also realized there was very little chance it would ever happen.
I had downloaded some chatting apps just to pass the time. I had a decent number of messages from women but also started getting more from guys, most of which I ignored but one came through from someone that was local to me and I decided to respond. It all started fairly innocent with generic conversation. I told myself I was just chatting and nothing else, but it didn't take long for the conversation to take on a more sexual nature. He told me that he was bi and I didn't try to hide anything and told him I had never done anything with another man but had become more curious about it and that I enjoyed being submissive. We had been chatting for several hours and I was becoming more turned on as we went when he asked if I would like to see his cock. I wasn't surprised that it happened but was surprised at how fast I answered yes. Within minutes I had several pictures waiting for me, a couple close ups and a couple full body shots with him holding it. It was a nice length, a little longer than mine and he had a very large head.
"Do you like seeing it?" he sent.
"Yes sir," I typed immediately.
"You think you would like to suck it?" he said.
I was more hesitant this time, even though it was just messaging through an app but nervously responded, "Yes I would."
He asked me to show him mine, but I told him I wasn't sure about that yet and that I had to go to bed but if he was around the next night we could talk about it some more. I laid there for quite a while after that reading back through the conversation and looking at the pictures. I ended up getting my lube out and stroking myself to those pictures until I shot a large load of cum on my stomach and chest. I used my finger to take some of that cum and put it in my mouth imagining it was his.
I thought about it the next day and decided if he told me to show it to him I would. I also caught myself looking at the chat several times throughout the day including the pictures. It was late evening when I logged in and had no new messages. I sent a simple, "Hey, how's it going?" and kept looking at my phone for a while. You could tell in this app when the other person looked at the message and I was hoping to see when he had opened it. I still hadn't heard anything a couple hours later and figured he assumed it would be a waste of time to keep messaging. I closed out, watched a movie and then went to bed. I woke up around 1am and looked at my phone and saw that I had a message, which I opened immediately. It said, "Hey, just sitting around working in my garage. You?"
"Just laying in bed," I sent and saw that it was opened almost immediately.