I first discovered the glory holes at the college campus. I was scared shitless the first time I noticed the glory hole and when I looked through the hole, I was greeted with a pair of eyes of an older college professor. I ran out of the bathroom that day, but the next day I was back and this time I wasn't scared. While I was in college, I visited those glory holes pretty much everyday. I sucked many dicks and got sucked many times.
A few years later, my best friend took me to my first adult bookstore. I was hooked! A few years later, I started working at one of the local adult bookstores. The first time I worked there, I worked by myself at nights and I sucked plenty of dick. The second time I worked there was a few years later and I worked there for another 2 years. This time, they had 2 guys working each night. There was one other gay man that worked there and he was as big of a cocksucker as I was. He was also the manager's pet, so he could do nothing wrong. The nights him and I worked together, it was always a race to get to the back to suck dick. But the other nights I worked, the 5 other guys were all straight and they hated going back there. So we had an agreement, I go play in the back all I wanted (during the shift and my off nights) and they didn't care what I did as long as I cleaned the booth area on the nights I worked. This was the time I started getting into anal too. So I was now I was sucking lots of dick and getting fucked occasionally too.
When I stopped working there, I started working another night job. So I would hang out in the adult bookstores during the day and work at night. I was amazed by the crowd during the day. Lots of straight guys, married guys and some really hot college students. I was hanging out at the bookstore pretty much every day. Eventually the bookstore with the best glory holes closed down. And the bookstore I used to work at was sold to a corporation that tore down all the walls in the building and rebuilt everything. The new booth area was smaller and had no glory holes. They did add 1 glory hole a few years later, but it is very small and low to the ground, so it makes it hard to use. With no glory holes in the area, this led me to start my own glory hole at my place. I did very well when Craigslist was still around. But when they stopped the personal ads, I started advertising on different websites. It is very hit and miss. I do have some regular guys that stop by. They are always fun. I do get some hot guys that will stop by, I love servicing them.
I've been hosting at my own glory hole for 8 years now and I've had a few small problems. Most of the time, the problem is guys not showing up after they ask to come over. No big deal, I just invite another guy over. But twice, I did that and ended up with both guys showing up at the same time. The first time, the both guys were okay with it. They both took turns being sucked by me. The second time, the one guy wasn't okay with it, but he was cool about it. He just zipped up and left.
The only big problems I have had was two different times I had a guy come over and he was drunk. He got super aggressive and ripped the glory hole down. Turns out both times was the same guy (I didn't realize it at first), but they happened 5 years apart.
I've been playing through glory holes for 30 years now. Anonymous sex through a glory hole is the hottest thing for me. Nothing is completely anonymous, I always have a very good idea who the guy on the other side is. I've never caught a STI. Sex through a glory hole is not any riskier than any other type of sex with another person. You NEVER know if they have something or not. And in those 30 years, I have never seen or heard of somebody getting their dick cut or stabbed or poked with a needle.