I was about 20 and my Top was probably in his 40's. (Note-I sucked my first cock at 14, and got a blow job the same year.)
I met my Top when he sat next to me on a bench at the Central Park Zoo in NYC. He invited me back to his apt on East 53 St. After a lot of sucking foreplay, he started fingering my hole which got me real excited. I think he assumed I had already been fucked. He tried to fuck me missionary style, but I was too inexperienced to know how to relax my hole. Every time he'd push his cock against my hole, I'd clench down on it, rather than opening up to him. And, of course, it hurt. After gobs of lube, and other positions, he finally settled on fucking me side by side. Although my hole was burning, somehow I was able to relax more in this position, and he eventually slowly worked his 7 inches into me.
At some point, I told him I was a virgin, at least anally. He got a lot gentler with me after that revelation.
So he slowly worked his cock in and out of my hole, and left it inside me until I got used to the feel.
Despite my asshole being on fire, I did enjoy the feeling of a man's cock balls deep up my fuckchute. He took me slowly, but eventually picked up the pace, and flooded my hole with his cum.
After his cock deflated, he slowly pulled out. Then, he gave me a half hour back and leg massage which felt wonderful, and helped me forget about by burning asshole.
He put some kind of numbing agent around my asslips, and mounted me again, and managed to shoot another load up me.
By this time, his roommate (lover?) came home. I felt awkward, but both put me at ease. George, the roommate, went to the kitchen and grilled some steaks in the oven, while my Top and I pawed each other, and eventually cleaned up.
We all had a cocktail, and, then a pleasant dinner. Thanks to my Top's consideration for me getting my cherry busted by him, it turned what could have been an unpleasant, painful experience for me, into something that I enjoyed.
While I did not get fucked again for about a year after that, I learned a lot from my first time. By the time I started hitting the baths, I knew I was a confirmed bottom, and had figured out how to relax my hole, and adjust to varying sizes of cocks. Unfortunately, because of the AIDS scare, I took few cumloads in my ass for 20 years or so. I turned off a lot of great looking guys because I insisted on them covering up.
Since I returned to bb sex a few years ago, though, I have made up for those lost years. While I still try to choose my Top, once I have, I don't ask any questions. I've learned it's just better to present my hole and go with the flow, so to speak.