Aaron Gardner, 29, "derived pleasure" from "terrifying and humiliating" five women who he met and robbed in hotel rooms, a court heard.
Over the course of three months last summer, the court heard, Gardner "booked sexual services" and arranged to meet the women in London, Birmingham and Nottingham.
Judge Gregory Dickinson QC, sentencing, said Gardner had stolen cash - sometimes totalling thousands of pounds - and spent much of it on gambling.
Judge Dickinson, who said the offences were of "considerable violence and seriousness", also sentenced him to five years on extended licence.