Very professional encounter, she did reiterate to me that she does not offer any unprotected services at all and gets tested when I asked her due to my worries over STI’s. Claims she’s also a mother and in the medical field. I understand it’s her word and not fact, but it did alleviate my fears momentarily.

My concern is that during the condom protected oral sex, I kept becoming soft due to me being intoxicated. I also had interruptions being that there were other people around in the place we were staying at and I kept jumping up and pulling my pants up with the condom still on. The condom at times rolled all the way up to the head and become very loose with space to spare at the tip. 

When it came time to penetrative sex, I asked to change the condom but she said it was not necessary. The condom was slid back and down and readjusted to fit snug at the tip. I do know that when sex was over (really only like 2min of penetrative sex), the condom was intact (water test) and seemed to cover my entire shaft.

I do not know if this counts as improper condom use and if it would still protect me. I ask because approx 2-3 days later I woke up with 2 tiny white head like pimples on the underside of my shaft that seem to have dissipated but very VERY slight redness persist in the spot. I’m nervous because I messed up and do have a steady partner. I also know my anxiety is not good and I could very be imagining a lot of symptoms down there. There’s no discharge, no smell. Just general itchiness and very very faint discomfort I’m attributing to my mind.

You describe a exceedingly low risk encounter. It sounds like your escort partner is knowledgeable and careful. Even among the highest risk persons (multiple partners without condoms), at any point in time most have no transmissible STI -- and your partner seems to be at lower risk than average. In addition, oral sex is low risk for all STIs, even without a condom -- and with condom protection there was no measurable risk. That your erection softened would not have increased the risk. And the pimple like spots you describe clearly were not due to any STI. And I also agree that the vague discomforts you describe are not worrisome, and that they probably indeed are anxiety driven.

I don't recommend STI/HIV testing on account of the events described. Do your best to move on without worry!

I hope these comments help relieve your concerns. Let me know if anything isn't clear.

HHH, MD

I just want to reiterate that you are aware that there was vaginal sex that took place, not just oral sex. 

My concern was with the condom becoming loose, with it rolling to the head and becoming very spacious at the tip, and rolling it back to fit loosely before the vaginal sex that I was concerned about. I was not sure if with the condom becoming all messed up, fitting very loosely at times and looking as if it was coming off and fitting it back on would reduce the effectiveness of the condom, or only if it broke would it be considered failure. 

Also, the redness and pimple-like marks seem to have gotten even smaller but the itchiness remains.

Appreciate your help!

Even without penile softening, during intercourse the penis may slide within the condom, carrying vaginal fluids under the condom. But protection is considered complete as long as the head of the penis and meatus (urethral opening) are covered. You're the only one who can judge whether this was likely in your case. In any case, it still sounds like your partner is at low risk for STIs, despite her profession. In addition, it also remains true that the symptoms you describe are not typical for any STI. Conceivably you have some skin irritation related to the exposure (e.g. inflammation from a spermicide or vaginal hygiene product?).

I still am not too concerned and don't see a clear need for STI testing. However, that's often a personal more than medical decision:  many persons are more reassured by negative lab test results than by professional opinion, no matter how expert and science-based. If you'll sleep better, feel free to have standard STI testing, i.e. gonorrhea/chlamydia testing (valid any time 4-5 days or more after exposure) and blood tests for HIV and syphilis after a few weeks. But I definitely would not recommend any other tests in this situation.

I do know for a fact that when penetrative vagina sex occurred, my penis was in fact fully covered upon entry and exit, and did in fact not fail. It was only the events leading up to protective vaginal sex that I was worried about reducing the effectiveness of the condom. 

As I’ve stated and you understand, the issue was before hand with the issues with the condom reducing the effectiveness of it which you commented on. 

I appreciate your help and will try my best to move past this.