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I can definatly understand where you are coming from. My situation is similar but I do trust my boyfriend and the only problem is that I'm a naturally jealous person no matter how hard I try to change it. The only way I was able to trust him was by talking with him. He needed to be completly honest with me and I had to be completly honest with him in return and not worry about what would happen.
I think the biggest red flag with this came up when you tried to talk to him about it he didn't seem to care about your feelings. No matter what your situation is at the moment, how is your relationship going to work or progress if he is not worried about your feelings?
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