Hi Roger!
Yes, I love Any Whitehouse doing 'Valerie'!
Hmm, well the two examples I gave (Dylan and Wainwright) are men singing from a female perspective. The other one that springs to mind is another from a folk song tradition. Bert Jansch singing 'Rosemary Lane'
https://www.youtube.com/watch?v=Y6ymZDtgV58
Rosemary Lane
When I was in service in Rosemary Lane
I won the goodwill of my master and did I
Till a sailor came there one night to lay
And that was the beginning of my misery
He called for a candle to light him to bed
And likewise a silk handkerchief to tie up his head
To tie up his head as sailors will do
And he said my Pretty Polly will you come too
Now this maid being young and foolish she thought it no harm
For to lie into bed to keep herself warm
And what was done there I will never disclose
But I wish that short night had been seven long years
Next morning this sailor so early arose
And into my apron three guineas did throw
Saying take this I will give and more I will do
If you'll be my Polly wherever I go
Now if it's a boy he will fight for the king
And if it's a girl she will wear a gold ring
She will wear a gold ring and a dress all aflame
And remember my service in Rosemary Lane
When I was in service in Rosemary Lane
I won the goodwill of my master and did I
Till a sailor came there one night to lay
And that was the beginning of my misery
Edit: It is harder to think of a song where a woman sings from a male pov...
Edit edit: OOH I've thought of one! Patti Smith doing Van Morrison's 'Gloria' with added sacrilegious poetry at the start! Now this kicks some ass/arse. Of course it's not
necessarily from a male perspective.
https://www.youtube.com/watch?v=bPO0bTaWcFQ