I'll do my best to "bottom line" this one, though I have a few things to say in addition.
You are asking if a condom for performing oral is "acceptable." Most men would say it is not; some will oblige you. What is "acceptable" is not cut and dry: there is no gay definition or mandate as to what type of behavior is allowed in any given circumstance. So the bottom line here is that if it is "acceptable" for YOUR personal level of comfort, then it is acceptable to make the attempt.
The worst that is going to happen is that you are going to have a guy remove his penis from a gloryhole and leave. There is a chance, albeit not a huge one, that if this guy happens to talk to other people in the bookstore or wherever it is that you are finding the gloryhole, he may tell them that you are putting condoms on dicks that appear through the hole. This may net you fewer visitors. Also, men leaving the opposite side of the hole on a frequent and swift basis may be enough to clue in the other guys that something isn't quite up to snuff with the cocksucker on the other end. But these are minor concerns.
Additionally, I'm simply curious -- if your dominant mistress is speaking to you via an earpiece, are you going to speak back to her at all? Or is she just going to talk the whole time? If you are speaking quietly to her, it may appear as though you're a nutjob talking to yourself. Men will give you a wide berth. But an even more important consideration -- communicating in this fashion, if caught, could very well get some guys really uptight. If anyone notices your earpiece, they could easily peg you for a vice cop, or someone doing surreptitious recording of events in a place that is not quite as "public" as it may seem to the casual observer. As an example, if you brought a camera of any sort into a bathhouse or bookstore, you'd be kicked the hell out in a flash -- and if you get someone pissed off, you could also get a solid punch in the gut.
I'd think this over carefully if I were you.
If you want an entire safe sex discussion about what is higher and lower risk, we can do that, but let's assume you know what's what. Everything GASlick said is also true, so pay heed to his admonishment.
I will SLIGHTLY disagree on one point, however. I don't think HIV + men are any more OR less likely to be in any particular location than HIV - men. The same applies for men with ANY potential STD, known to them or not. And let's not forget that LOTS of people HAVE STDs and have NO CLUE. They are able to spread STDs no matter WHERE they are. HIV+ men can simply keep their status undisclosed to a partner, a trick, a friend -- doesn't matter. HIV+ men can lie online, in person, at a bar, in a park, at the supermarket -- anywhere they meet someone. So it isn't always true that they have no one to have sex with and MUST seek out anonymous encounters. Besides, whatever the venue, there would be little to alleviate guilt through anonymity if a guy is THAT deceptive and hateful. It might be a little easier to stick his dick through a hole and say nothing in that fashion, avoiding only the physical act of lying to someone's face, but rest assured there are many low-lifes out there who will do BOTH of those things and sleep well at night.
Also, I find it JUST as likely, if not MORE likely, that bookstores and similar places for anonymous and private sex are FILLED with men just like you: married guys, straight guys with girlfriends, curious guys, bi guys, etc. Are they LESS likely to have an STD? Maybe. Maybe not.
So go ahead. Use a condom. See what happens. No one is going to be upset with you or DO anything to you because of it. They will simply walk away if this isn't their thing.
The earpiece deal -- well, I wouldn't talk if I were you. And I'd make SURE it cannot possibly be discovered.
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