Transcripts of chat logs of naturally-occurring, sexually exploitative interactions between offenders and victims that took place via Internet communication platforms were analyzed. The aim of the study was to examine the modus operandi of offenders in such interactions, with particular focus on the specific strategies they use to engage victims, including discursive tactics. We also aimed to ascertain offenders’ underlying motivation and function of engagement in online interactions with children. Five cases, comprising 29 transcripts, were analyzed using qualitative thematic analysis with a discursive focus. In addition to this, police reports were reviewed for descriptive and case-specific information. Offenders were men aged between 27 and 52 years (M = 33.6, SD = 5.6), and the number of children they communicated with ranged from one to twelve (M = 4.6, SD = 4.5). Victims were aged between 11 and 15 (M = 13.00, SD = 1.2), and were both female and male. Three offenders committed online sexual offenses, and two offenders committed contact sexual offenses in addition to online sexual offenses. The analysis of transcripts revealed that interactions between offenders and victims were of a highly sexual nature, and that offenders employed a range of manipulative strategies to engage victims and achieve their compliance. It appeared that offenders engaged in such interactions for the purpose of sexual arousal and gratification, as well as fantasy fulfillment.