YOU SAID:

I walked my dog down the street and it was fun.

INTO JAPANESE

私は犬を通りを歩いていて、それは楽しかったです。

BACK INTO ENGLISH

I was walking down the street with a dog and it was fun.

INTO JAPANESE

犬と一緒に道を歩いていて楽しかったです。

BACK INTO ENGLISH

I enjoyed walking down the road with my dog.

INTO JAPANESE

私は犬と一緒に道を歩いて楽しんだ。

BACK INTO ENGLISH

I enjoyed walking down the road with my dog.