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I haven't had anything like what you did with your 20yo concerning clothes, but have had fun memories from prior spankings with my boys.
Also my sister and I on many occasions while talking with mom and each other on Face time then Zoom have reminisced on past and present spankings, the worst, different stories and laughed at times.
This, what I am going to share has happened a few times with my boys, Zach, Mason and Tommy. I remember the first time I heard them on this subject, it was during one of our campout sleepovers, the older boys were 12, we were all sitting on the back porch talking. I don’t remember how it came up but they got onto the subject of spankings from me, maybe I had recently spanked, ‘worst spankings ever’ things they did to get a spanking, ones they will never forget, I do believe it was also 'badge of honor time' with 10 and 12 year olds.
They all agreed my spankings were/are the worst ever and have told me many times I have to be the best spanker ever. Bobby brought up he loves the cuddling after, they agreed and have said that since, I know they need the personal physical aspect of the bonding of the bare bottom spankings over my lap, that skin to skin contact, holding them tight, even if they can't articulate that yet, I do believe they know that.
It also has to do with knowing my spankings are given with and out of love, they do feel safe as you said.
They have over the years had these same conversations and remembered some spankings I had given them that I had forgot.