I have always known that you soldiers were all ugly, unlike we handsome sailors!  Nonetheless, when a woman decides to become an escort, she has to accept that she will be with men who are not featured in Gentleman's Quarterly ads.  That is part of the job.  As for age, well I am 64 and I have yet to be rejected.  

Worry not about your looks, but rather on treating her with respect.  She will love you for it in both senses of the word.

An old anchor clanker!