Responses
Well it depends on what was the dildo made of and how his asshole is stretched. I suppose that this dildo was made of "regular" rubber that isn't overly soft so yeah a wrong thrust would hurt. Also I don't think he is loose enough to take both of it, he barely fitted it after a looong period of time having sex...
This way of having sex looks too dangerous to me like the dildo could hurt the dick and the asshole at the same time, or a bad trust could make the dildo enter completely before the dick and the dick push the dildo further in.