Are these comments from my boyfriend inappropriate?

My boyfriend often comments to me about other women in a physical/sexual way. For example he will be telling me about his day, he works at a school, and will mention how short the girls skirts are and how one girl was dressed provocativly (it was non uniform day) and she asked him a question and suddenly there was a big pair of boobs in his face. He is in his fifties! He said he thought the school was not being strict enough and he was not merely gawking. He often mentions how revealing a woman’s top is that he just saw at the shops.

We used to work at the same company and some of the guys he worked with in the workshop tell me he was always commenting about female colleagues, usually in a sexual way. He would often say things to me as well like ‘did you see so and so was wearing a see through top’ etc. I find his comments disrespectful and hurtful but he says all men are the same and we end up arguing, he gets angry and says he's not the guy for me.

I've been in several relationships and been married before but have never experienced this at this level before.

We have been going out for some time and my feelings are strong but am I just being insecure and unreasonable? Maybe I’m out of touch. Surely he can talk like this to his heart’s content with his friends but I don’t see why he finds the need to say these things to me.

He has a lot of female friends, which is fine but seems to have a reputation as a ladies man. He is quite affectionate with others and I once saw him with his arms around another woman at a party. He said she has hurt her foot and he was steadying her. I guess his comments do make me feel a bit uneasy.
He has not, by his own admission, had much success with past relationships and his wife left him for another man. He says he’s not the best looking guy, which he isn’t, and always struggled to get the girls.

I would really appreciate any advice.

Are these comments from my boyfriend inappropriate?
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