1. To have rough, angry sex with a woman you find very attractive, but you hold back a little bit to ensure the integrity of the condom as insurance so you do not have to pay child support or spend any unnecessary time outside of the bedroom together.
2. To be brought unwillingly into a more serious phase of a relationship with a parter you would rather have as a causal sex buddy.
To Break the Trojan would mean the girl would become impregnated and you would either have to marry her, or pay child support for 18 years.
Ryan: Man Michelle is smoking hot. Would you hit that?
Erik: Shit yeah man, I'd hit that with a vengeance, but I wouldn't Break the Trojan.
Ryan: Word, I hear she's an alcoholic anyways.
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