I have no advice except on STD issues, which you don't have. I recommend you follow your doctors' advice in all respects and certainly a urological evaluation seems to make sense.
Thank you very much doctor. That puts my mind at ease. That said - should I still plan on visiting a urologist? Got any advice for treatment?
The opening comments were meant to say "condom protection for both vaginal and oral sex", not anal. Sorry for any confusion.
Another aspect is that STDs rarely if ever cause urinary retention is extremely rare, but is common with prostate infections.
Welcome to the forum.
Almost certainly you have no STD, and almost equally certainly your symptoms are unrelated to your non-marital sexual exposures. With condom protection for both vaginal and anal sex, there is no realistic chance you acquired a urethral/urinary STD; and in any case, those STDs primarily cause discharge; painful urination can occur with discharge, but usually not by itself. Also, urethral STDs generally do not cause frequent or urgent urination.
Rather, your symptoms and the lab findings are typical for a bacterial urinary tract infection. Although UTIs are relatively uncommon in most men, they are quite common in diabetics. Often there is a focus of infection in the prostate gland (with or without prostate-specific symptoms), and if that localized infeciton flares up, the infection spreads into the urinary tract, i.e. bladder etc. Based on your symptoms, the urinalysis findings, the treatment prescribed, and the plan for urology evaluation of your prostate, this is what your doctors believe is going on. And so do I. The only atypical feature is your apparently negative urine culture, but that could simply mean that the infection was still limited inside the prostate gland; and some cases of prostatitis are due to unknown bacteria.
There is no point in STD testing at this time. Even if you had been infected (which I do not believe at all), the ciprofloxacin would have cured it and at this point the tests would be negative.
I hope this helps. Best wishes-- HHH, MD