Since 1989, Prague has become a major destination for gay tourists and for sex tourists of all orientations from Western countries. To date, relatively little attention from policy or social theory perspectives has focused on males involved in sex work in Czech Republic. Based on the author's fieldwork in the gay community in Prague during 1999-2002 with follow-up visits in 2004–2006, this article looks at the experiences of young men (especially gay-identified men) involved in homosexual sex work in Prague, describes their relationship to the mainstream gay scenes in Prague in several phases since the mid-1990s, and discusses problems they face. Findings include the following: 1) Transactional sex exists on a continuum - ranging from one-time explicit exchanges of sex for money, through flirting for drinks, to longer-term relationships strongly motivated by financial considerations. 2) The latter types provide both a potential point of entry to sex work and a point of contact or plausible deniability on the gay mainstream. 3) Young men involved in various forms of sex work provide one of the major encounter points between Western tourists and native Czechs and Slovaks; this has been aggressively marketed in Western Europe and North America since the mid-1990s by pornographers, both Czech and foreign. 4) Male sex work does not generally provide a long-term career in Czech Republic; many former sex workers appear to end up in jobs such as bartending or as tour guides, where they can use their language skills and customer service experience.