This chapter proposes that extraordinarily generative psychic possibilities can sometimes inhere in perverse sexual practices. The set of propositions may allow analyst to conceptualize perverse clinical material not from within a state of alarm but with the readiness to identify that sexual transgressions can offer formidable access points to unrepresented psychic bits. For Cyra it is the transgressiveness of pain and the threading of skin to skin that crosses the line. Yet which acts will be experienced as transgressive varies widely across different individuals: for one person it may be the shame of oral sex, for another the pain of anal penetration, for a third the longing to be reduced to begging one's lover. When met by the responsive conscious as well as unconscious presence of an analyst, perversions can constitute a conduit towards the transformation of beta elements into alpha, of the enigmatic into the representable.