YOU SAID:

It's his first time on his own.

INTO JAPANESE

それは彼自身の彼の最初の時間です。

BACK INTO ENGLISH

It is he of his own for the first time.

INTO JAPANESE

彼自身の彼は初めてです。

BACK INTO ENGLISH

This is the first time he himself.

INTO JAPANESE

これは初めて彼自身。

BACK INTO ENGLISH

This is the first time his own.

INTO JAPANESE

これは初めて彼自身。

BACK INTO ENGLISH

This is the first time his own.