I lived out of state for a short while once and got pretty horny for a short while, decided to try my luck with craigslist a few times before getting burnt out, urge resurfaces, repeat
Met one did for non diaper related things, didn't really feel it pop off and ditched it, second person is into diapers, I meet him at a small cafe nearby, tells me to come diapered.
Meet pleasantly, etc, eventually he pops the question if I'm padded or not, talks about what he enjoys in domming, etc, really lays it all out since he gets I'm new to the kink scene
out of the blue just says afterwards to start peeing myself, obviously I oblige until he tells me 'stop'. He continues to play a little red light green light with me as I'm blushing crimson red pissing my pants away in this little cafe.
Eventually we scoot to the restroom, I sheepishly ask for a change, he takes a look in the stall, gives me a few squishes and admantly states he wont be doing it in a public bathroom (probably smart on his half, dude clearly had experience)
I'm struggling to think of a place to use since I had roomates and couldnt use my place, I forget his reason but his place was also off limits. My assblast of an idea was remembering a private, lockable bathroom in the shopping center near my work. Lo and behold he agrees and we climb into his truck
He drives the five or so miles all the way over, talking to me about stuff, occasionally reaching over to fondle me now and then, have me wet a bit more, the likes. Get to the shopping center and I'm practically skipping to the bathroom, we get in, lock the door, he has me drop my pants and gets to fondling me, has me rub myself in front of him, etc
Gets real close in, basically pinning me to the wall, eventually I beg to be able to masturbate by reaching my hand down the front and he lets me, I didn't last ten more seconds while whimpering things lewdly, he smiles, tells me good job, etc, and politely says I should get changed (honestly sad he didnt change me). I get into a clean change, we head back to his truck, he fondles me a bit more but gives me some basic advice on real life kink play and such, while I thought I'd have post-nut regret I rolled with it surprisingly well, even if being one-hand-groped wasnt as hot any more
He finally drops me off after being incredibly polite, which probably took all the 'creepy old man' factor off the situation with how respectably he handled it. And by god I will never forget the last thing he said to me, with a wink and fingergun, "never quit being kinky, kid"
I kind of regret not riding that train a bit more, the one other person I had met (non diaper related, I lost interest) made it at least somewhat obvious he was willing to 'sugar daddy' me, I'm sure if I applied myself and got out there more I could have landed a cozy dommy diaper daddy and not needing to work for at least a few years