It all depends on the experience level and needs of the client. The less experienced you are the more foreplay and lube you need.
Basically, I try to tease you until you are excited/relaxed enough you are, then I penetrate with my gloved finger and find your prostate. I massage it, watching your reaction to find out what kind of touch you respond to. Also, I stimulate the balls and penis a little to make the experience more erotic. From there on, anything can happen. I can finish you while on your hands and knees, or you can turn over and combine the finger play with the handjob.
Milking can include pretty rough play, but it is only for very experienced customers.