Well, you should be so lucky that's he is honest and has told you everything.
Clearly, his initial intentions were to just "vent" himself to an older woman on a continual basis, as she probably welcomed the conversations and he probably saw her as a Mother figure.
Somehow the "advantage" was taken.
Seems to me that you both care deeply about each other, but both were curious about the opposite sex, as you were 14 when you met him and he was broken up with you, over the fact that you cheated and left his heart behind for a while.
Fact is, it's not relevant if you want to make it work.. It's over, it happened.
Personally, if he only stated that she was 40, you still would have had a million questions... It doesn't matter that he gave you a blow to blow description, that she was a co-worker...
You are just going to have to accept that this all happened when you weren't together and concentrate on the now..
Living in the past will not make a great current or future relationship.
CW




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