I've done it a few times. The first time was a HUGE mistake. This was long before internet hookups were a thing. My best friend and I used to cruise the classified ads in the back of the gay magazines you would find in the bars. Being from a small town in the midwest, there was never any ads for somebody who lived within 100 miles.
One night, I found an ad for a guy, who lived in St Louis (about 150 miles away). His ad sounded really hot to me. I called him and we chatted for awhile. Being a broke college student who was horny all the time, I made the stupid decision to meet him. The huge mistake was I had enough gas money to get there, but I didn't have enough to get back. He promised he that he would help me fill my car up. So I drove there, he wasn't bad looking, but he didn't really match what his profile said, the sex was okay and when it came time to leave, he had like $4 to give me for gas money. Pretty sure I wouldn't make it very far. I did get lucky, I still had my last paycheck in my wallet and they had a local bank in St Louis. The bank wouldn't cash it at first because it was an out-of-state check, but after pleading with the cashier and manager for a while, they finally cashed it for me. I made it home and tried to erase that experience from my mind.
The other time that comes to mind was a great experience. After my dad died, he left me some money and I spent a year doing whatever I wanted. I had a fuckbuddy that I had been seeing for a few years whenever he was in town. He happened to stop by one weekend and I asked him about going to visit him in Milwaukee. He told me he had a weekend off the next month, so we made plans. I drove up to his place for that weekend. He took me around to different places in Milwaukee. We went shopping. We went out to eat. We visited some bars. And we had lots of sex. The most interesting time was he took me to a 10-story apartment building that was a block away from his place. His friend lived there and he had the elevator code to get up on the roof. We went up there, it was overlooking Lake Michigan and the place was empty. He jokingly pulled my dick out of my shorts and started sucking me. Of course, this lead to me fucking him on the roof while we watched the people and boats on the lake. Very fun experience. Now I am just glad nobody came up on the roof while we were there.