I doubt it, There are a number of Hadiths showing the prophet making jokes, smiling, and having fun. None are heavily at the expensive of the other person's feelings and it seems that it is not required to ask for permission (although I think if the person shows or expresses discomfort then it would be best to respect that). Here is a couple of examples:
Anas ibn Malik reports: “A man asked the Prophet to give him a mount. The Prophet said to him: ‘I will give you a she-camel’s son.’ The man said: ‘What use do I have for a she-camel’s son?’ The Prophet said: ‘What camel is not born to a she-camel?’” (Related by Ahmad, Al-Tirmidhi, Abu Dawood and Al-Bukhari in Al-Adab Al-Mufrad). Here we see the Prophet making a joke, as he tells the man who requests a mount that he would give him a she-camel’s son. The man takes it literally and thinks that the Prophet is giving him only a young camel that is not fit to travel any distance carrying a man on his back. But the Prophet explains that every camel is the son of a she-camel.
The Prophet even made practical jokes. Anas ibn Malik reports: “A Bedouin called Zahir ibn Haram used to visit the Prophet bringing him gifts from his desert area. When he was about to leave, the Prophet would give him a good supply. The Prophet once commented: ‘Zahir is our man from the desert and we are his urban people.’ The Prophet loved him, but Zahir was rather ugly in appearance. One day the Prophet came on him as he was selling his stuff. The Prophet held him from the rear, while Zahir could not see him. He said to him: ‘Let me go! Who are you?’ He then turned his head and recognized the Prophet. He tried his best not to press his back against the Prophet’s chest. The Prophet said loudly: ‘Who will buy this slave?’ Zahir said: ‘Messenger of God! You will find me unsaleable.’ The Prophet said to him: ‘But with God, you are not unsaleable. As God’s slave, you are highly valued.’” (Related by Ahmad, Al-Tirmidhi and Abd Al-Razzaq).
Here is a good example of it possibly being ok to make a joke, hurt someone's feelings, but make them feel better in the end:
On another occasion the Prophet joked with an old woman who asked him to pray for her to be admitted into heaven. The Prophet said: ‘No old woman will ever enter heaven.’ The woman turned away crying. The Prophet said to those nearby: ‘Tell her that no woman goes into heaven as an old woman.’ He then read the Qur’anic verses: ‘We shall have brought them into being in a life renewed, having resurrected them as virgins.’ (56: 35-36)
Here is a reference which provides a number of other examples: