Herpes or Ingrown Hair/

Hello,
I am a 23 yo male who has had a few casual encounters over the past year, with most occuring between January and April.  I have not been very sexually active recently.  Whenever I seem to shave my genital area (which I do semi regularly) I see to develop razor burn and a few follicles begin to bleed, and then I have a habit of picking and trying to drain the follicle of blood.  Likely not a good habit, but this is what I have done.  I continue to pick these follices and now have 2 areas that look like they are infected to a degree.  One near the shaft of my penis the other higher up.  There are no clusters and I think that these areas come up after I shave and after I pick it them but with my anxiety over them I cannot be certain.  Earlier this year I also had a rash under my left armpit for a week or so which went away.  The areas do not hurt unless I pic at it and squeeze it.  Does this sound like Herpes or an infected hair follicle/ingrown hair?  Are Herpes painful on their own?
Also, what are the odds of contracting HIV during heterosexual sex (female to male) during which woman is menstruating?  
This has all just opened up a can of STD hypocondria...any help is appreciated :)