I'm a 42 year old man and I frequently get pimple-like bumps high up on the inside of my thighs on one or both legs. They are soft and not firm, and are easily manipulated. They are not particularly tender or painful, but they are annoying and unsightly. I tend to try to squeeze them out like a pimple, but instead of being filled with pus, they are filled with blood. Sometimes they "Pop" on their own. Do you know what these are? Is there anything I can do to stop these from occurring?

They sound like folliculitis, which is an inflammation of hair follicles, or perhaps a rash caused by heat or friction of your thighs rubbing against clothing. You should go to the Doctor to rule out more serious skin-related problems like an STD or perhaps a fungus of some sort.