When I got my anal cherry popped (I was in my 50's), and my rectum split by a cock for the very first time, it hurt a little more than I expected - especially at first. But the sensations of being inseminated were awesome! The guy who did the job told me about "anal silky seconds", and how after a hole has been stretched, fucked, and spermed, it's actually very pleasant to feel a cock slide in and take its pleasure. The bottom usually feels the stretching, fullness, and insemination without the flinch and grimace of getting the sphincter popped.
Is that how a bottom feels in a gangbang?
(The guy who devirginized my hole was very considerate, patient, and prepared me well for what had to be done. He was average length or maybe a little bit longer, but rather thick. He said it had been many years since he took a virgin hole by himself - it had always been a virgin much younger than me, and it was done by two or three guys. The thinnest cock always went first and finished fast. Then my partner would go in and administer an extended fuck. )