YOU SAID:
once i licked my cat and he liked it
INTO JAPANESE
私が私の猫をなめたら、そして彼はそれが好きだった
BACK INTO ENGLISH
If I licked my cat, then he liked it
INTO JAPANESE
私が私の猫をなめたら、それから彼はそれが好きだった
BACK INTO ENGLISH
If I licked my cat then he liked it
INTO JAPANESE
私が私の猫をなめた場合、彼はそれが好きだった
BACK INTO ENGLISH
He liked it if I licked my cat
INTO JAPANESE
私は私の猫をなめたら彼はそれが好きだった
BACK INTO ENGLISH
He liked it when I licked my cat
INTO JAPANESE
私は私の猫をなめたとき彼はそれが好きだった
BACK INTO ENGLISH
He liked it when I licked my cat
That didn't even make that much sense in English.