My bare headed life started at age 12. My then older girlfriend - may she rest in peace - did not like my covered head and the extra folds at the end of the foreskin. Every time we were together, she made sure the skin was retracted. From there on, I stayed retracted longer and longer. Then there was a point in time I was fed up with the occasional flip backs of the skin over the head. The awkward sensation of the foreskin's end touching underwear or bed sheets did never feel good and the situation begged to be corrected. That was not always possible straight away. Putting your hand deep in the trousers to pull the skin back is not something you do in public - at least I don't. I remember driving in my car with an aunt. In that position, with the seat belt on, a corrective move was not an easy or quick thing to do, let alone with someone next to me who would notice. When the sensation of the foreskin-clothing contact got worse, enhanced by the constant awareness of it, I pointed to the right and said Look there, a heron! in the hope my aunt would look to the right and try to spot the bird which might take enough time to perform my planned action. That was a miscalculation. With my hand in my pants she turned around "I can't see any bird" directly followed by "What are you doing". I then uttered something like "fixing something". From that point on she stared straight forward ans did not say a word for the remainder of the trip. When arrived at the train station I was taking her, she got out and said "get circumcised" and off she went.
That was the point to investigate options to stay bare headed but without a circ. The solution was cutting my frenum which worked out fantastic and I'm the proud owner of a 24/7 bare head for the last 44 years.