Wa `alaykum As-Salamu wa Rahmatullahi wa Barakatuh

 

If you friend is Muslim, then he first should know that is it a major sin and that he should repent from that immediately.

 

As to the question, it does not matter how he feels about himself, in Islam he is considered a male and should not be exposed to unveiled women unless they are of his Mahram like mother or sister.

 

Almighty Allah knows best.