All perfect praise be to Allah, The Lord of the worlds. I testify that there is none worthy of worship except Allah and that Muhammad, sallallahu ‘alayhi wa sallam, is His slave and Messenger.
What you mentioned is possible; the grace of Allah is without limits, and the woes and griefs expiate sins. So if the sins of a person are expiated, it is hoped that he would be relieved from the griefs caused by the sins. However, the Muslim should beware of indulging in committing sins; feeling secure against the Plan of Allah, The Almighty; and arrogantly be deluded by His Forbearance and Forgiveness. The believer should fear Allah, The Exalted, as due, and the true fear of Allah is the one that deters the person from doing whatever does not please Allah.
Allah, The Exalted, says about the People of Paradise (what means): {And they will approach one another, inquiring of each other. They will say: Indeed, we were previously among our people fearful (of displeasing Allah). So, Allah conferred favor upon us and protected us from the punishment of the Scorching Fire.} [Quran 52:25-27]
Allah knows best.