I was laying on my bed bored one night when I started getting in the mood. My sex drive had been very low, I had not masturbated for over a week, and I was losing interest in the usual things that turned me on. So I decided to try something different: rather than reaching for my cock I began gently fingering myself, then gradually going deeper until my thumb was all the way inside. I have experimented with this a little before but it often felt more physically uncomfortable than pleasurable. But on this particular night it was really turning me on and I began to get very hard.
Realizing that the anal pleasure wouldn't be enough to get me all the way off, I decided to indulge in a special talent of mine as well. I rolled onto my back so my legs were over my head, and braced my legs against the frame of my bed. From this position I am able to put the entire head of my cock into my mouth. This is not fictional: I am extremely flexible and am blessed with a nice large cock. I have sucked myself many times but never while fingering myself too. I discovered that this position made me more relaxed and able to go deeper and enjoy the penetration more.
I continued to suck my cock and work with my thumb, synchronizing the motions as much as possible until I reached an incredible orgasm. I came in my mouth and let it slide down the back of my throat, then rolled over and enjoyed the lingering euphoria.