I did this during a particularly boring part of my life were I was a traveling salesman. I was young and would be in hotels for a few nights. I'd bring my good stash with me or if I flew would just pick up some cheapies. I also experienced 95% dudes jerking off or wanting to jerk off in front of me.
But Omegle also led me to *depressing to think about* my only diaper experience with a woman where we both shared the love of diapers.
I was wearing some kind of high end printed diaper, this was maybe 2017ish, I had a bandana over my face and had the laptop on the bed in front of me while I had my legs crossed so I could easily pan down to show diap. It using a myriad of tags; diaper, diapers, abdl, pullups, goodnites and whatever else my horny brain could conjure up to increase the likelihood of another ABDL talking to me especially a cute girl.
So I finally match with a girl and we do some talking first. She says she can't really use diapers much but she had some kind of homemade one on. I don't believe she showed it too much, but it was either a towel with some plastic covering or more likely some kind of pad set up or a baby diaper inside underwear.
I just remember the time we spent together, we peed together, and we both masturbated. It was incredibly hot and probably what has kept me searching for another bio-female who actually loves diapers like I do.
Then like the horny little coward I am, as soon as I came I hit the "next button" and never saw her again. It's really a great allegory for how significantly and consistently I manage to fuck up a good thing.