penetrative adjective4 •That can or does physically penetrate something; piercing, penetrating.Would'st thou be window'd in great Rome, and see / Thy Master thus with pleacht Armes, bending downe / His corrigible necke, his face subdu'de / To penetratiue shame […] — 1606 •Pertaining to sexual activity involving penetration by the penis (or similar object).I've been in a relationship for nearly a year and we have an amazing sex life as is, but we've never managed penetrative sex. — 2013 •That can penetrate opposition defences. •Displaying insight or discrimination; acute; penetrating. formsmore penetrative · most penetrative