I don't see the term "prostitute's pupil" in AMBOSS or FA23 (I don't have FA24 so can't reference that - I doubt they'd add this term in FA24). A quick PubMed search didn't really reveal much, so it's not a term commonly used in the literature.
While it may be colloquial and has an alliteration, I don't think it's the most appropriate term since many patients who are not sex workers can become infected with syphilis. I don't have access to UW Step 2 or Step 3, so I don't know if the tagged QIDs have sex workers as the pt's social history.
If others disagree, I won't riot or anything. But in light of clinical practice and the increased rates of syphilis in the general public even without "risky" behaviors, I think this term is a little antiquated.
Linked AMBOSS article about syphilis with link to epidemiology with no mention of sex workers. Obviously they would be high-risk, but I can't find the term "prostitute's pupil" anywhere. https://next.amboss.com/us/article/sk0t6T#FcbgVs
Source: AMBOSS - https://next.amboss.com/us/article/sk0t6T#FcbgVs