While prior studies have targeted street-based male sex workers as potential vectors of disease transmission, the number of men who work independently through Internet chat-rooms and other online endeavors has steadily increased. It is likely that these men differ substantially from their street-based counterparts in terms of sexual risk behaviors with their clients. The purpose of this study was to explore the ways in which the Internet has impacted the work of male escorts and their sexual practices with clients. Semi-structured qualitative interviews and quantitative surveys were administered to 46 such men. Less than half the men reported unprotected anal sex with clients. The qualitative data lend support to this finding, in that the majority talked about refusing any unsafe sex with clients, and many reported taking the extra step of educating their clients about the dangers of risky sex. Some of the escorts described the methods used to incorporate safer sex practices into sessions with their clients. Internet-based male escorts can play an important role as potential sex educators on the front lines of the fight against HIV and other sexually transmitted infections.