This happened about 20 years ago before I even knew guys could cum from anal. And I say it was my “first time”, but there hasn’t been a second time, yet. The first time it happened for me there was no “mindset”. I don’t even remember if I had gone awhile since masturbating, it was so unremarkable it was just another day. I went into an adult book store/theater and watched a little porn and played with myself a little. There was a guy in a red had and I asked him if he’d like a blowjob. I got on my knees and started sucking him. He was a grower. It got stiff in my mouth and was an impressive 6-7”. He was fucking my mouth and looked down at me and said “can I fuck you?” With this nice girthy cock in my mouth I said “mmmffmmfff”, stood up and bent over for him. He flipped his hat backwards and started fucking my ass. This wasn’t the first time I had been fucked, but it was the first time I had been fucked by someone who knew what they were doing. I could feel the entire length of his cock going in and coming out, nice and steady, nice and slow. That’s when I felt the pressure welling up inside, slowly building its way from the base of my cock. He sped up his thrusting and it felt like he was going deeper and deeper with each fierce thrust of his cock. And then? BAM! I stated cumming all over the place. I was bucking back on his cock and squealing and squeezing my my ass and he started cumming deep inside me too. I collapsed in a shivering erotic daze literally in a puddle of my own cum as he stood over me with that backwards red had grinning a conquerer’s grin. I looked up at him and just licked the remaining drops of cum off his cock and whispered an exhausted “thank you”. He pulled up his pants and walked out of there and didn’t even close the door.