As every person has already said upfront, there is always some risk to contracting some form of STD, including HIV, if you do nothing to protect yourself. Our point here is to not minimize or downplay the risk. Sucking the unprotected cock of any anonymous male puts you at risk ... period. If you don't know the other guy's health history, you are at risk.
Will the other guy be receptive to putting on a condom before letting you suck his cock? As a matter of gloryhole practice, probably not. But, you might find someone who will put on a condom. Are you patient and disciplined enough to find someone who will use a condom before letting you suck his cock? Just remember that you assume the burden of the risk for sucking the cock of an anonymous person.
As for using a cell phone with an earpiece to hear your Domme. It sounds like a novel approach, but has the potential to be misunderstood by others if you are discovered using one in this way. While it may be easy to conceal, the earpiece has the potential to cause others to misunderstand your intent. You are in an environment where very little if anything is ever said between a cocksucker and the man whose cock you are sucking. You are also in an environment where an cellphone earpiece might be viewed as a law enforcement attempt to entrap someone. Probably not a good idea for the more obvious reason. On a more humorous and less serious note, I'm sure your Domme would like to hear you slurping on somebody's cock through a gloryhole. This certainly raises phone sex to the next level when you are literally providing the appropriate sound effects -- slurping ... moaning ... etc.
I know that some Domme's can be very demanding these days. But, what you seem destined to do might have some unintended consequences that were never anticipated.
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Those who deny freedom to others deserve it not for themselves. And, under a just God, cannot long retain it.
-- Abraham Lincoln
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