This very likely was my fate as a young child, before I had many memories. My mom was a stickler for hygiene, and I was left uncut because I was born very prematurely. I've written a number of posts saying that had I been carried to normal term, there is zero doubt I would have been circumcised, given the prevalent medical advice in the USA at the time. This is despite my parents emigrating from a decidedly non-cutting culture! Following that advice, subsequently, also meant that there would have been efforts made to make sure I was retractable and cleaned underneath at diaper changes, etc.
As such, my penis had a quite retractable foreskin at a young age. The entire glans could be revealed when flaccid, at ages 4-5, the earliest I can recall anything dealing with my genitals. I do remember my mother making sure in no uncertain terms I washed underneath my foreskin in the bath/shower, to the point of her checking by gently squeezing my glans to make sure nothing came out of the meatus. (On the other hand, my dad, who is either cut really loosely or has an extremely short foreskin, just said that being clean underneath was all that was necessary and sufficient.) Through childhood, my mom was concerned that I had too much foreskin and extended an offer to pay for circumcision should I decide to undergo it, because it was more hygienic and very likely more preferred among female partners in my future. This led me to a slight mental complex regarding the topic that persists to this day, hence my activity on this sub-forum.
Thanks to the wonders of the internet, I now know that my foreskin definitely is on the longer side of average. When younger and erect, I could pull the skin down to about the corona (definitely not past it). This state persisted until I was finished with puberty, at which point frequent “further activities” showed I could pull it back further, but would cause discomfort. My frenulum is quite prominent as well, and was short - I resolved the frenulum breve by manual stretching over a few more years' time, and would consider myself completely retractable by now.
All that said, I pretty much had just a couple penis-related issues in my life - two infections down there as a boy that each resolved quickly + cleanly, and discovering a latex allergy later in life (that also affects my hands and is related to my line of work). Regarding the popularity of foreskin among sexual partners, I've written about that too, and my conclusion is that any ignorance is typically due to unfamiliarity and cultural norms rather than any particular malice, and that it's not a big deal either way once “in the flesh," so to speak. Because any woman seeing a guy's penis in person is probably attracted to him at some level, and a bit of skin ought not to be a deal-breaker at that point. When I've brought up the topic of circumcision with a number of American women aged 20-60, their reactions spanned the entire range from “it's a terrible practice" on one end, a lot of “I don't really know, isn't being circumcised supposed to be a good thing for hygiene and that's all I've experienced", a few “it doesn't matter at all,” all the way to those who think foreskin is gross and would cut any sons for sure. The last group, by the way, includes some people who are immigrants or whose families are from non-cutting cultures. So that's how strong the American cultural mores are! (And the anti-circumcision women include some that you'd think as ‘typical’ white Americans, so go figure…)