When I started out on my own sexual journey in life, I didn't care if anal sex hurt. Oh, it did hurt. A lot, especially my first time -- when a boy much older than me shoved his monstrously huge penis inside me without using lube, and then proceeded to fuck the shit out of me for an hour. But one I learned about lubricant, I didn't care about the pain.
Indeed, my attitude was that I wasn't a good lover unless I was taking another man's penis as deep, fast, and rough as he wanted to give it. I didn't really realize I was a bottom, not yet. I thought that bottoms were effeminate, queeny, and lazy, and I didn't want to be those things. Nevertheless, I REALLY enjoyed anal sex, especially with a man whose erect penis was extremely large, extremely long and extremely thick. I remember one blue-eyed, blond-haired muscle-boy (let's call him "Jed") had a cringe-inducing thick one that had significantly above-average length to it as well. We first fucked in the dark, me face-down on his bed and him supporting himself on locked elbows above me. It took him nearly 45 minutes of really brutal pounding to get enough stimulation to ejaculate inside me. (Big boys take time.) Afterward, we turned on the lights. He wanted me on my back, and I was happy to oblige. He knelt, stroking his still-erect penis, and gently fingered my hole to see how much of his semen could spill out of me. (A lot, since there was a really huge amount inside me.) Then he pulled back his foreskin, pushed his huge red knob against me, and violated me again.
"Jed" sort of continued kneeling, rocking back and forth and watching his obscenely thick monster slide in and out of my stretched-to-the-limit asshole. I whimpered, I was stretched so tightly.
And this time, "Jed" got off on seeing his huge club buried into a tightly-stretched anus. He came in under five minutes, asked if he could continue (I said yes), and he came again in under five minutes.
We had sex a lot with the lights on after that.
I remember watching gay adult film in my late teens and in my 20s, and seeing these 18 to 27 year old twinks and frat-boys riding cock the way I rode cock. They enjoyed it. The bigger the better! The more excited, the more physical, the more energetic the sex -- the better the film was. You might hear a sex worker shout "Oh fuck!!" as a really long or thick one slid into his sex worker's hole. But there wasn't any pretending that this was "his first time" or that it hurt. There was none of the "bottom's reach" -- that oh-too-common signal in modern gay adult film in which a bottom reaches to touch his top's thigh, the signal that the top should slow down, take it out, not fuck him as deep.
No, back then -- sex workers were sex workers. They knew what you wanted to see. They knew it wasn't going to work if they faked being in pain. And pain wasn't what got viewers off: Good, old, solid gay sex was. Happy gay sex. Ecstatic gay sex.
When John Davenport shoved his nine inches into Michael Gere's sex-worker asshole in Powertool, Gere whined and whimpered. Not because it hurt, but because it felt so good!
I often seek out twink porn today, to recapture some of that magic. Some of it (like the Staxus scene here), is good. Good, because the porn star knows that sex should be enjoyed and be energetic and not contain fake fake fake protestations of "it hurts" and "please stop".