My first experience was back in the 70's (even before the advent of alternative newspapers - at least in my town). Took on the task of arranging "entertainment" for a bachelor party. Not an easy thing to do.
Choices were (1) - finding someone off the streets (with all the risks that entailed).
(2) - strip clubs - they weren't the glitzy places that are common today. Many, if not most, strippers doubled as prostitutes. And you had the advantage of being pretty sure the stripper wasn't a cop. But it wasn't easy to develop the level of trust needed to book an outside the club appointment - for a bachelor party no less - without at least being a regular at the club.
or (3) find a pimp.
It turned out that most people were only about 2 degrees of separation from a good pimp. In most workplaces there was someone who "knew somebody".
Good pimps had a stable of some pretty decent ladies - and a network of "publicists" in all walks of life. One of my coworkers introduced to a "publicist" who worked in my company - who, in turn, introduced me to the real life pimp (and also vouched for me).
The pimp met with me, showed me pictures of several ladies and told me a little bit about them. I made my choice and paid in advance (that was the only way he worked). He let me know that he would "hold me personally responsible" to keep my guests in line and that I was to call him immediately if things started to get out of hand or if she decided she wanted to leave (remember - there were no cell phones back then either). The "publicist" let me know that the pimp had the muscle to take care of his girls and that I would be wise to take that responsibility seriously.
He dropped a very attractive lady off at the appointed time. Everyone had a good time. We called him a couple of hours later and he was there to pick her up within a few minutes.
He did a great job - for us and for his lady.
But the advent of the internet has made things SO much easier.