Bump and Rash on shaft (seperate occurances)

About 5 months ago i shaved the shaft of my penis and had unprotected sex shortly afterwards, within the next couple of days i noticed a small bump, about the diameter of an eraser from a pencil, form at the base of my penis. I have been to the doctors twice and both times they determined that it was not Sexually transmitted but rather an infection of an ingrown hair.  I was prescribed 2 different medications(AMOX/CLAV 875/125),(CIPROFLOXACIN, 500MG), neither have worked.  The bump has since grown to the diameter of about a dime, and it pops like a pimple with yellow discharge, occasionally blood.  
The second issue im having is that this last weekend i had sex 5 times in about 24 hours, occasionally my girlfriends vagina was dry, the day after sex i noticed a particularly painful area of skin on the left side of my shaft, its hardly visible but i can clearly feel the pain.  It itches occasionally but mostly hurts to the touch...Is this a friction rash from too much rough sex, or could it be a sexually transmitted disease...the area in question is partially covered with pubic hair and the bumps appear to be hair follicles...Any information would be helpful.  Thanks.
alilconcerned

[H. Hunter Handsfield, M.D.]

As to the first problem, you may have a sebaceous cyst that is getting reinfected periodically.  See a dermatologist; it may need to be excised (surgically removed) to prevent recurrences.

The other sounds like physical irritation, as you suspect.  It doesn't sound like an STD, and came on too fact; no STD causes pain or discomfort within 24 hours.  I would sit tight and consider seeing a health care provider if it doesn't clear up in a few days.

Good luck--  HHH, MD

[alilconcerned]

The itching has increased since i posted the first thread.  I took my trimmer to the area and have noticed small rash like bumps.  They do not appear to be filled with anything, they look like hair follicles that are inflamed for some reason.  I did some research on herpes and im not sure if this could be an early stage or if its something completely different.  Thanks.
alilconcerned

[H. Hunter Handsfield, M.D.]

Red bumps and pimples (folliculitis) often occur in areas of shaving--a very common problem these days.  Still doesn't sound like herpes or any other STD.

HHH, MD

[alilconcerned]

Just wanted to thank you.  I appreciate you taking the time to answer my questions.  Makes me feel a lot better about this.  Thanks again,
alilconcerned