Well, I have always had ic issues (never out of diapers) and recall real well starting school in Pampers (cloth at home) they actually did fit right with no "hacks" up until about 4th-5th grade (we are talking about the old plain white plastic backed fan-fold tape on ones).
BUT I don't think it was actually a diaper that had anything to do with it - more like a series of events in High school, involving a girl.
AB items around just because it made things much easier on everyone, including myself. They had more medical sounding names, and looked slightly different - but if you looked at the actual function...(example, while don't recall the term used now a bottle that was square instead of round, that sort of thing). Anyway, all through school it was no real secrete from anyone that I needed diapers, everything else though pretty much was, except for a small group of really close friends that were at my house all the time.
Fast forward to about 10th grade had this girl that we both seemed to click just fine (looking back I would say even if she didn't know at the time, young CG), came by the house, obviously expected to see diapers around, but spotted all that other stuff to. Started sort of friendly like teasing me about it, seemed like she was expecting me to get mad over it - and I likely would have if it was a guy doing it, or even a girl that I had no real attraction to, but her...It surprised me, but didn't really bother me.
Anyway, things just kept progressing from there. She even started doing some thing with the claim that I need the help anyway, nothing at all to hide from her anymore, and give mom a little break (actually more of an excuse to get some "alone time") - and that is when the playing REALLY started. At every step I'm pretty sure she expected me to object, but I never did (honest don't know why not, more and more she was treating me like an infant, and in a friendly way teasing me about it, but for some reason I just let it keep going).
Eventually Halloween was coming up, and she managed to convince me to go to a party with her dressed like a baby. At first I didn't want to do it, but she was VERY convincing - even pointing out that I already had most of what it would take to do that real well, just a few things to make it look extremely authentic, and it would be done really good. Finally I agreed.
Well, she was right, it was VERY good - I would say too good! EVERYONE took notice as soon as I walked in, but after about 5 minutes the guys just ignored it, but none of the girls would leave me alone all night! Well, that caused a BIG fight, I even pointed out that was her idea to start with, but she was fuming!
Fortunately after about two weeks, that was the end of it, not the last bit mad at me anymore, and things continued right where they left off, getting even more involved.