My first plugging experience was with an plug that I personally made on a lathe some (many) decades ago. We had this "tech class - workshop" in last year of elementary school were we learned all kind of tech things - some simple electrics (battery, lamp, switch, such things), mechanics (lever, sprocket, etc) and also woodworking. I remember loving it and lathe was a machine I really got a grip on. At that time I also found some porn and started exploring sexuality and of course, lathe was a perfect tool to make something dildo like (usually it came out like it even if you didn't want to - well on a lathe everything comes out at least cylindrical and then add some grooves and make a part of it thinner and voila - there's your dildo). I remember lacquering it and one day I brought it home, I had a few hours till parents would be home and of course got the porn and the "dick" out . Seeing what did they do with such things in the porn mag, I had to try the same. I remember that it was really hard getting it in my butt (nobody told me some preparation or lube would be nice... oh on the pics everything looks so smooth, easy and enjoyable) and then some of it was left sticking out of me (it was quite long, fortunately, so it didn't get "swallowed" up), I could see myself in a mirror and it seemed to me somewhat awkward with that pole sticking out. Not feeling anything special or even remotely like it seemed it would feel like in the mag, I removed it and of course it had some shit on it - doh... at first I thought how I'd get rid of it, cleaning shit wasn't something I was looking forward to and as it did not anything special to me, I thought maybe throwing it out of the window. On the second thought, I realized that it surely would be found and could be linked back to me, so I reluctantly washed it and put it in the drawer underneath some other stuff. Didn't use it again and after some time I eventually got rid of it.
I got my first "real" plug - a smallish jelly plug - quite a few years later in a shop out of my home town, and by then I knew the secrets of the trade so it was oh so much fun! When I learned about the dangers of materials such as jelly (although it held up so well I thought it was silicone, but when I did the flame test on it, it did burn) and it got replaced by silicone toys. I remember going out once with it and while it stayed in OK at first, it started slipping out after some time (to my absolute horror) and I remember turning my back against the wall on the street to try to "casually" push it back up in place with my hand. Thinking of that makes me blush even now, after all these years. But that little thingie started my obsession with plugs, having so much fun with them!