confused about atypical symptoms

[confusedpremed 4]

Hi all, 

I've been looking at this forum for a while and was hoping to get some advice. I've had ongoing issues for about a month and it's not really clear what's going on. I'm gonna start from the beginning: 

I was drunk and had anal sex unprotected for a very brief period of time, less than a minute, before my wits came about me and we stopped having sex altogether. About a week after, I noticed a pinching pain on the right dorsal (upward) side of my glans penis. I began to suspect a herpes prodrome, since I've had a herpes scare in the past (HSV-1 -- came back negative). I started panicking and the pinching lasted for about 2 days, and no lesions or noticeable redness appeared, so eventually I figured it was nothing. ~1 week after this, I wake up for a tailgate and notice a small red patch, completely flat, with no lesions in the foreskin. I figured it was some kind of irritation and went about my business for the day. Then, the following day (so about 2 weeks out now), I'm laying down and notice a sudden sharp pain on the shaft of my penis. I notice a red jagged rash and monitor it throughout the day, it has a burning sensation. However, by the next morning (less than 24 hours later), the redness is completely gone; in the following days dry skin begins to develop in tiny circles, similar to how eczema resolves (definitely not raised scabs). I go to my university doctor, and he tests me for the normal STD panel, but says he doesn't notice anything abnormal about my penis (the dryness was very faint at this point and he didn't look very closely or use any viewing instrument). Test comes back positive for chlamydia, I begin treatment, and the symptoms for chlamydia start and end over the course of that week. I begin to develop a burning sensation in my scrotum and extending down the perineum to my anus (no contact occurred there) and notice a smell similar to a yeast infection/intertrigo (which I'm prone to). I also notice three raw "cuts) in the folds of my foreskin (I'm circumcised but have some excess skin), in addition to flat pin prick red dots along the rim of the glans with no fluid center, almost like fine point sharpie. I treated cuts with zinc oxide ointment and they dried up really fast, and the burning went away after a shower. I go home for the weekend preparing for spring break, and decide to start treating with gold bond spray and lotrimin, convinced that this is a fungal or yeast infection. That night I notice a small pinprick size raised white spot, doesn't really seem to contain fluid, but I panicked and made a second doctors appointment with my primary care. By the time I wake up like 7 hours later, the whitehead is gone aside from some very slight redness in a tiny pinprick spot, the doctor says it's nothing, but prescribes me Valtrex in case of emergency on vacation and orders HSV IgG test (now just under 4 weeks out). I didn't take valtrex and symptoms subsided but don't disappear altogether. I get a call from the doctor, HSV-1 and HSV-2 both negative, I'm aware that tests aren't fully accurate until ~12 weeks, but I take it as a good sign. However, towards the end of the following week, I begin to notice redness on ventral side of penis by the urethra. I treat it with fungal creams etc and it kind of comes and goes over the course of the week. At the end of the week I had a long travel day, and notice that it is significantly worse, there is raised skin and irritation but no fluid-filled lesions or scabs. I start taking the 3-day course of Valtrex, while still treating with fungal cream, which leads me to today. Fungal cream appears to be irritating the inflammation, so I just stopped, but I notice redness in my foreskin again near where it was before. Still no noticeable lesions, hardly any pain. When I urinate it passes over the inflammation on the glans and even then it doesn't really hurt at all. There is very slight burning in the red region. 

I'm sorry to give so much context but it's been a long and stressful journey. Has anyone had similar symptoms? The time frame is strange, the symptoms are strange, and I'm confused as to how to interpret the test results at 4 weeks. However, since I acquired chlamydia, it doesn't seem far off that I would acquire another STD, especially given this all began after that event. 

Thanks in advance for the help. 

EDIT: I also developed eczema during my trip (likely due to sun exposure or possibly stress) but this could be a potential confounder. Also, friction and masturbation both definitely appear to contribute to the inflammation.

Edited March 28 by confusedpremed