These issues are your boyfriends and he's taken things way too far.
I have a simple rule for my bf. I have made it quite clear to him that he should never ask questions that he doesn't want the answers to.
If I can be totally honest here. Your bf is an attention seeker. Full stop. He is clingy and needy and needs constant reassurance.
It is a fact of life that there will ALWAYS be people prettier than us and ALWAYS be people uglier than us. So too is it true with guys and anatomy.
He has incredibly low self esteem. And chances are, before he had even met you, he had doubts about his size.
As for you not disclosing who you had slept with, whilst I don't condone lying, he needs to consider this from YOUR perspective.
Nowhere did you indicate you enjoyed the one night stand. Nowhere did you indicate you were remotely happy about sleeping with the old man, and he needs to learn to put it into context. Flipping hell your bf had one night stands too!!! Talk about calling the kettle black.
You need to put up boundaries. He needs to know what is and isn't okay to continue to this day to harp on about. If I were you and he carries on with a rant about your past I'd simply say I'm not having this conversation and walk off
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