YOU SAID:
It hurts to put my pants on.
INTO JAPANESE
ズボンをはいても痛い。
BACK INTO ENGLISH
It hurts even if I put on my pants.
INTO JAPANESE
ズボンをかぶっても痛い。
BACK INTO ENGLISH
It hurts to wear pants.
INTO JAPANESE
ズボンを着るのは痛い。
BACK INTO ENGLISH
It hurts to wear pants.
That didn't even make that much sense in English.