I have been in a steady monogamous relationship for a little over a year now with the love of my life. He is amazing and our sex is often very good, but he has never experienced an orgasm in all our time together... ☹️

He does take an anti-depressant, and he is also somewhat shy when it comes to sex (I am the first person he has had successful penetration with). In the past he has had difficulty maintaining an erection with other women. However with me he is able to keep one the entire time, it just never comes to fruition.

I thought that once he became more comfortable, then he would be able to have one, but now it has been over a year and I am still the only one coming. He is still uncomfortable with the idea of us trying other types of things to make him finish. Any advice?