Yes. I used to go cruising a lot when i was 18-21. When I was 19, I went one day as usual, only ever to suck as many cocks as possible, and maybe top on the rare occasion.
One guy, mid 40s, suggested we go to a slightly more secluded area of the woods. I was sucking him and really enjoying it, thinking he’d cum in my mouth like all the others. But he then picked me up, turned me around and pushed me so I was leaning on a tree. I then felt his huge cock rubbing my hole, which had only been fucked twice before.
I told him no. I said I was far too tight and it’d never get in. Then he just pushed so hard, and in it went. It hurt so much, with only my spit for lube. I was just in shock and pretty much paralysed. Then he started thrusting really hard, and the pain eased. It took him no more than a minute to cum and flood my ass. He remarked how I was his tightest ever fuck, he laughed a little after it was done, then walked off and left me standing there in shock half naked.
I was in pain for days afterwards. Walking, sitting, bending - anything was agony. But I still really enjoyed it. Technically it was rape, but it still turns me on so much.