The daughter of a surgeon father and a mother who worked in real estate investment, Prince's early life was one of privilege, with a family that was in her words "socially prominent".

Despite having been previously diagnosed with an unresolved Oedipus complex, Prince confided to her doctor, Karl Bowman, about her inclination of crossdressing, who in return advised her to "learn to accept [her]self... and enjoy it."

[14] After her marriage ended, Prince returned to the University of California, San Francisco and began working as a research assistant and lecturer in pharmacology.

[10] The exact time at which Prince took on the name Virginia is unclear, however one of her earliest known writings, the article "Homosexuality, Transvestism and Transsexualism: Reflections on Their Etiology and Difference" published in 1957, is credited to "C.V.

In 1963, the inside jacket of the magazine stated the publication as "dedicated to the needs of the sexually normal individual who has discovered the existance [sic] of his or her 'other side' and seeks to express it.

The magazine operated on three core objectives: These three objectives—education, entertainment, and expression—were promoted in order to "help... readers achieve understanding, self-acceptance, [and] peace of mind".

Virginia Prince recounts in her autobiographical issue that originally the cost of production was too high to be sustainable, due to its having been printed on mimeograph paper.

[24] A complete run of Transvestia, both physical and digital copies, is in the Transgender Archives at the University of Victoria in British Columbia, Canada.

[10] Her long history of literature surrounding issues of crossdressing and transvestism was rooted in her desire to fight against those who disagreed with liberal sexual ideology.

[10][27] Notably, in her 1967 "The Expression of Femininity in the Male" (under the pen name "Virginia Bruce"), Prince discusses the supposed psychiatric links between cross-dressing and sexual deviation that were commonly believed in at the time.

[28] In other works, Prince also helped popularize the term 'transgender', and erroneously[citation needed] asserted that she coined "transgenderist" and "transgenderism", words which she meant to be understood as describing people who live as full-time women, but have no intention of having genital surgery.

"[20] By the early 1970s, Prince and her approaches to crossdressing and transvestism were starting to gain criticism from transvestites and transsexuals, as well as sections of the gay and women's movements of the time.