We analyzed chat transcripts from 590 undercover Internet sex stings across the US, using the Linguistic Inquiry and Word Count software program to examine trends in sexual word usage, total word usage, and clout (a measure conveying social dominance) for convicted child sex offenders and undercover agents. Offenders and agents varied greatly in their scores in these word categories; however, generally, offenders used more words in each: 91% used more sexual words, 66% used more words overall, and 82% exhibited more clout than their respective agents. Linguistic analyses can provide the trier of fact with objective measures of psychometric properties that may help them assess the offender’s predisposition and appropriateness of government conduct. Additionally, our data-set shows the distribution of these language dimensions across a wide sample of offenders, providing a statistical context for linguistic evidence from individual cases. As language-based digital evidence become more prevalent, forensic linguistic analyses may prove invaluable in the courtroom.