Why do some gay men continue to engage in unsafe sexual practices despite the known and widely publicized risks of HIV infection? Dominant models of health promotion have been criticized for reducing this complex psychosocial issue to a question of instrumental technique - 'use a condom every time'. Accordingly, there has recently been an attempt to develop a deeper understanding of unsafe sexual practices by paying attention to the 'subjective meaning' manifest in gay men's own accounts of their behaviour. However, this paper argues that such studies have failed to develop an adequate understanding of the historical nature of such behaviours and the way in which they are embedded in a 'cultural psyche' that the individual gay man may not even be consciously aware of. Accordingly, using published autobiographical and fictional narratives written by gay men over three different periods of gay history (pre-AIDS, during AIDS and 'post'-AIDS), this paper aims to show that contemporary 'barebacking' behaviour may constitute one manifestation of a 'resistance' or 'transgressional' 'habitus' that has remained a consistent feature of gay men's individual and social psyche since the early days of gay liberation. The paper discusses the potentially health-damaging implications of this 'habitus' and the possibility and desirability of facilitating change.