I understand the attraction of this. There are a lot of offices near me with many hot female staff and I would love to fuck a hooker in my office with the blinds open with the chance that the women from offices saw what was happening.
Problem is in this climate you open yourself up to extortion and blackmail from a dodgy hooker. She could get annoyed with you for seeing other hookers (has happened to me a couple of times), or if you take a break from her she could get angry and start using your place of work as leverage.
To be honest, it isn't just hookers, any female that you are banging in secret be it hooker or civvie, is a potential nightmare if they know where you work.
I really want to live the fantasy though and only way I can think of doing so safely is making the hooker sign a confidentiality agreement drawn up professionally and getting her ID!
But clearly the chances of a hooker agreeing to the above is non existent so I'm afraid this one fantasy that has to remain a fantasy.
Definitely don't take the risk mate. Not worth it.