Penis envy in Freudian psychoanalysis refers to the theorized reaction of a girl during her psychosexual development to the realization that she does not have a penis. Freud considered this realization a defining moment in the development of gender and sexual identity for women - the parallel reaction in boys to the realization that women do not have a penis being castration anxiety. In contemporary culture, the term sometimes refers inexactly or metaphorically to women who are presumed to wish they were men.
The psychoanalytical concept of penis envy is unrelated to the "small penis syndrome" which is the anxiety of thinking one's penis is too small, (though Otto Fenichel did explore the possibility of a boy's envy for the adult [paternal] penis).
Freud introduced the concept of interest in — and envy of — the penis in his 1908 article "On the Sexual Theories of Children": it was not mentioned in the first edition of Freud's earlier Three Contributions to the Theory of Sex (1905), but a synopsis of the 1908 article was added to the third edition in 1915. In On Narcissism (1914) he described how some women develop a masculine ideal as "a survival of the boyish nature that they themselves once possessed."
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