I had successfully sucked not only my first cock, but several others since. I had discovered that I liked giving pleasure to the guys I met with, that I wasn't really interested in reciprocation, and that I had a preference for being in and out with no frills or small talk. Over the months since that first cock, I learned a lot about myself. But one of these visits had me thinking...he asked if I would be willing to bottom. I didn't bottom that night, had never really even thought about it before...but the thought lingered.
The lingering thought led to some reading which then led to some experimentation with toys. A couple of dildos and plugs later, starting small and gradually moving up in size, I found that I enjoyed jerking my cock with a toy inserted or that I sometimes just enjoyed the toy alone. Ultimately I decided that the lingering thought of bottoming could become more of reality...I wanted to not just experiment with sucking cock, but I wanted to experiment with being fucked by a cock.
I kept up with Craigslist and sucked the occasional guy off; happily swallowing their cocks and the cum that they would shoot into my throat. I started looking for an opportunity to bottom, but wasn't successful in getting anything worked out. Eventually I got up the nerve to post my own ad, looking for a guy that understood it was my first time and would top me anyway. I received a fair amount of responses, but most were either scams or never had a realistic chance of working out.
One message caught my attention, a guy who seemed understanding of what I was looking for. He wasn't in a rush to get together and we exchanged a significant amount of messages. Despite being significantly nervous, we eventually agreed to meet at his place and set a date and time.
The day came and I cleaned myself up as best I could inside and out. I even inserted a small plug that I had before driving to his place. I wanted to be ready when I got there; so just before I arrived, I stopped and pulled the plug out. When I got there, he met me at his side door; a taller, thin slightly older guy who was just as friendly in person as he was in our e-mail conversation. I followed him to a bedroom, where I saw that he already had a condom and lube laid out on a nightstand.
There wasn't much small talk and I followed his instruction. He turned on the TV and started a porn, though I couldn't tell you what kind of porn it was. We took our clothes off and I climbed onto the bed on my hands and knees. He took the lube from the nightstand and started feeling and then fingering my ass, first one finger and then a second. He asked me if I liked to be rimmed and when I told him that I had never been, I felt him start to rim my asshole. My nerves had already started to relax and I was enjoying the play, but when he started rimming my ass, I really relaxed and even moaned a little.