As a trans-gendered person, I've always heard things in Paul's lyrics that sound like they come from the similar places as my own deeper, gender-oriented feelings.
I don't mean intentionally overt lyrics like in "Get Back' or "Ob-La-Di." If anything, those are too obvious. But many other songs have a vibe to them that speaks of close, identifying knowledge of the inner-feminine archetypes of personality. His mother was a Catholic nurse, traits that will tend to build a strong respect for feminine archetypes in a developing personality.
His key masterpiece songs in The Beatles all hinted at the existence of a 'spirit-woman' who brings relief and comfort, and the absence of who's presence brings melancholy and despair, which is exactly what cross-dressing means to those who are introverted and introspective, as Paul is. I'm talking about songs like "Let it Be," "Yesterday." and "Hey Jude."
But 'transvestite' means cross-dressing. Whether or not Paul ever actually 'dressed' in women's clothing, no one can say. If he did/does, it's in private. However, he was certainly well aware and acknowledging of his soul/anima/inner feminine side, which related through many of his songs.
Jung always said that confronting and relating with one's anima/inner feminine spirit, in an introspective way, is the key to spiritual depth and creative expression, and none would argue that Paul, when he is on-form, is one of the most deeply spiritual songwriters in popular culture history.
But none can say whether he actually 'cross-dresses' or not. He may well have found that songwriting was a more productive outlet for the same feelings. After all, who really needs to dress in trivial 'clothes' representing the inner feminine personality, when you can, "let her under your skin," which is what most transvestites are actually seeking?
Incedentally, George Harrison was strong in Vaishnavist Hinduist faith, which also recognizes, as part of their model of divinity, the feminine deity Radha, who equates to the Jungian concept of Anima, and without whom The Krishna is not considered complete. This can be seen as a direct correlation to the dual-gendered nature expressed in a lot of Paul's songwriting.
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