Between 2 to 4 years ago I had several encounters with sex workers. (Around 6 or so) All of these encounters were limited to receiving unprotected oral. My previous sexual encounters were all monogamous relationships with protected sex and unprotected oral. 

A year ago I was tested by my doctor for Chlamydia and Gonorrhea which both came back negative. At the time I also had rashes on my back and legs, which my doctor diagnosed as folliculitis.  He prescribed me 500mg of Keflex for the folliculitis as well as a topical cream.  The back and leg rashes continue to be an issue however.  

I asked him about testing for HIV and Syphilis and he didn't recommend it. He stated that the syphilis rash would have been on my palms and soles. However, I have since read about that not being particularly true. I have never noticed a syphilis chancre but I am uncircumcised and have read that it can be easy to miss. I suffer from anxiety and have recently been worried that I may have had syphilis all along and that I now have latent stage syphilis. I'm worried about what effects this may have on me in the future. 

My question is should I go back and demand that my doctor test me for syphilis and hiv? Also, if I had syphilis or even latent syphilis, would the 500mg of Keflex had any effect on it?

Welcome to the Forum.  The chance that you acquired either syphilis or HIV from the exposures you describe are close to zero.  Several reasons:

1.  Both syphilis are relatively uncommon infections.

2.  Condoms are highly effective for prevention of acquisition of all STIs and rarely fail;  when they fail it is obvious because condoms break wide open.

3.  There has never been a case of HIV proven to have been acquired as the result of receipt of oral sex- not ever.

4.  Acquisition of syphilis from receipt of oral sex is very rare and when it occurs, it is usually the result of sex between men who have sex with other men.

5.  While there are not good formal studies, Keflex is active against syphilis and a week or more of Keflex would likely cure it.

Thus, I would be willing to make a substantial bet that you did not acquire either HIV or syphilis from the exposures you describe and I am not a betting person.  On the other hand, while I see no clinical need for testing, I see no reason why anyone should refuse to do these tests once to prove to you that you were not infected.  I hope this comment is helpful.  EWH

All of my protected intercourse partners had confirmed that they were negative for HIV and all were female. My only real concern was unprotected oral. 

With regards to the Keflex, I've read a couple of places that it could also disrupt a syphilis test from an accurate reading. Is this possible?

The Keflex didn't work too well on my folliculitis. Is there an antibiotic I can request from my Dr. that would deal with both folliculitis as well as deal with latent stage syphilis for sure? And just to confirm, there's no way that my current leg and back rashes could be related to syphilis with my last possible exposure being 2 years ago correct?

I have since married and had a child. My wife would've been tested in prenatal care but I'm just concerned I could have passed something on to her or my child while she was pregnant since she had that testing. 

These would be last questions on this matter. Thanks again. 

I'm not sure what you mean by the term, "disrupt".  IF you had acquired syphilis, Keflex probably would have cured it.  It would not have changed test results.

Your persistent rash is in no way consistent with syphilis.  The rash of syphilis would have persisted for a month or so and then resolved.  On the other hand, folliculitis is notoriously difficult to cure with antibiotics as folliculitis is primarily a matter of clogged pores in the skin.  Measures to keep pores open, such as regular use of a loofah sponge to help keep ores open, can be quite helpful in control of folliculitis. 

I really would not worry about syphilis but, if you continue to worry, I think a single blood test for syphilis will be negative, PROVING that you did not acquire syphilis from your exposures of concern.  Hope this helps.  EWH