For infusion sites, I was told to ONLY use the abdomen. The truth is that I find that to be the LEAST comfortable. After consulting with other pumpers, I started using other sites and I found that the absorption is JUST as good. My doctor still tells me to only use the abdomen (so I put the infusion set there before I go for my endo visits 
… ). The most important thing it to rotate the sites so that you don’t develop scar tissue.
Any other time, I use the upper buttocks, lower back (“love handles”), or upper thighs. I particularly like to use the Silhouette on the upper buttocks and upper thighs. I use the Quickset rather on the love handles and abdomen. I highly recommend testing out the other infusion sets and seeing which one you prefer. Minimed might send free samples of each if you ask.
As a general rule with the Silhouette, the less fat that I have in the area, the smaller the angle that I insert with (I insert by hand). Could it be painful because you are inserting it too deeply? In any case, your infusion set should not be painful (maximum when you insert and 30 minutes afterwards), in my opinion.
Here is a blog post about the pump holders that I use. You have to scroll down to see the one that I use on my calf. I’m not sure if the same one would fit around a man’s calf as well, but you could find something similar. Also, I know about a holder called “Invisapump”. I think it works for men, but not women. I ordered one and it didn’t work for me. In fact, I would be willing to mail it to you, as I will never use it. If you would like to try it out, then send me a private message with your mailing address and I will send it.