Growing up in the 50's and 60's, I knew early on I was "bi", but didn't have much opportunity to act on my feelings through my college years. Just after that, Uncle Sam invited me to a little police action in SE Asia-not a good time to be looking for other bi males.
Fast forward four years and a new job contracting to the military for support also stifled my searching. By 1980 I was getting married to a very vanilla girl who took a dim view of anything anal. Kids arrived four years later, and my time for looking for male playmates took a 25 year hiatus again.
While I've been "late to the party" for a few things in life, my search struck pay dirt this past October when I was contacted by what turned out to be a doctor. After several emails confirming our general compatibility, we elected to meet. This was my initiation into anal sex and it was everything I had hoped for and beyond. He used a condom while I lay on my back and he entered me.
I have been doing "anal training" over the years with my 1.75" butt-plug and that allowed insertion of a firm 6.5" long/1.5" diameter hard penis without pain. He started thrusting and came to a climax very soon as I gripped his shaft with my anal sphincter. While I didn't plan to seek him out for a reason, my introduction to anal was first rate by any standard.
We parted on great terms with each other. Out of the blue, two days ago, I received another email from him to se if we might get together again as he could host. Today was that day to meet, and he left two separate loads of semen in my rectum. (He is HIV- per US Gov't. military testing in October and doesn't practice un-protected sex).
I have no regrets and have enjoyed both meets.