I tried it once after seeing loads of memes like this. Admittedly, it felt pretty good. But then post-nut clarity kicked in and I realized I was left with a gross-ass sock and just ended up throwing it away. 0/10, would not recommend.
And even after doing it myself once, I've still never understood the "cum sock" that implies you do it multiple times in a single sock and keep said sock around... that's just fucking disgusting.
If it's a pleasure thing, Is it something that's performed more by those without foreskin, perhaps because they don't have the natural sleeve effect provided by the missing skin?