Being completely serious here, it sounds as if you need a trainer AND a good therapist. A trainer-slash-escort is not going to fix you.
Insecurity around people you perceive as 'better looking' won't go away with gym time or having a good-looking guy working with you. This feels like an issue you need to talk about with someone who is familiar with it and can work you through these feelings in a healthy, professional way.
Physical motivation and body reform is awesome, but a trainer's place is to stick to form, diet and weights.
I'd say leave the heavier lifting to a licensed mental health professional. I wish you well sir