This Article demonstrates that the execution and design of gay sting operations are constitutionally suspect. I posit that law enforcement officials are punishing men for constitutionally permissible expressive conduct conveying messages of sexual attraction and desire, and are therefore executing gay sting operations in ways that violate First Amendment free speech guarantees. Moreover, despite the fact that people of all sexual orientations have public sex, gay sting operations are only being targeted against men who have sex with other men. Thus, I argue that the selective enforcement of lewd conduct laws raises doubts about the legality of gay sting operations under the Equal Protection Clause of the Fourteenth Amendment. I also critique the accessibility and effectiveness of the entrapment defense, which is the primary legal defense available to male victims of illegitimate gay sting operations. More specifically, I posit that the entrapment defense is inadequate because many victims of illegitimate gay sting operations waive their right to invoke the defense by accepting plea bargains due to fears of losing their jobs, being registered as sex offenders, and facing ostracism from the public, their families, and communities. Men from disadvantaged economic backgrounds are especially unable to invoke the entrapment defense because litigants must fully pursue claims against law enforcement in order to raise the defense, which often results in lengthy and expensive litigation.