After Mahāprabhu’s return from Gaya, when He commenced His saṅkīrtana movement in the company of His devotees, He would sometimes hold His nightly kīrtanas in the house of Candraśekhara, just as He would in the house of Śrīvāsa Paṇḍita.

All the Vaiṣṇavas felt great enthusiasm when they heard that Mahāprabhu had begun His saṅkīrtana movement. Every night, these kīrtanas took place in the house of Śrīvāsa Paṇḍita, and on certain occasions, in the house of Candraśekhara Ācārya. (Caitanya Bhāgavata 2.8.110-1)

Jagāi and Mādhāi were two brothers who, though born in a high caste brāhmaṇa family, had nevertheless adopted robbery as their livelihood. By Mahāprabhu’s causeless mercy, all of their sins were cleansed and they were given the opportunity to engage in saṅkīrtana with the rest of His devotees. Candraśekhara Ācārya was amongst the associates of the Lord who witnessed these wonderful events. “Vakreśvara Paṇḍita and Candraśekhara Ācārya both know all the activities of Caitanya Mahāprabhu.” (Caitanya Bhāgavata 2.13.240)

Mahāprabhu put on a play about Vraja-līlā in the house of Candraśekhara Ācārya. This līlā has been described in great detail by Vṛndāvana Dāsa Ṭhākura in his Caitanya Bhāgavata, Madhya-khaṇḍa, Chapter 18. Kṛṣṇadāsa Kavirāja Gosvāmī has briefly mentioned the event in his Caitanya Caritāmṛta:

Then Mahāprabhu performed Kṛṣṇa-līlā in the house of Candraśekhara Ācārya. He Himself played the role of Rukmiṇī. He sometimes became Dūrgā, Lakṣmī or the Divine Energy. Then He sat down on the deity throne and distributed love of God to all the assembled devotees. (Caitanya Caritāmṛta 1.17.241-2)

Then Śacī’s son, completely absorbed in the kīrtana of the Lord’s Names, called out to Sadāśiva and Buddhimanta Khān. “Today I will go to Candraśekhara’s house where I will dance in the dress of Lakṣmī. Arrange for conch bracelets, saris, bodices, golden ornaments and other paraphernalia that will be suitable for our costumes.” Having so ordered him, Mahāprabhu and His companions went down the path to Candraśekhara’s house. (Bhakti-ratnākara 12.1949-52)

Here is a brief summary of the story as found in the Caitanya Bhāgavata: One day Mahāprabhu revealed His desire to put on a play with His devotees about His pastimes in Vṛndāvana. He told Sadāśiva and Buddhimanta Khān who would play which role and what they should wear.

According to His instruction, Buddhimanta then arranged for appropriate dress and makeup for those who would be in the play, pleasing Mahāprabhu immeasurably. Mahāprabhu announced that He would dance in the role of Lakṣmī, but that only those whose senses were controlled would be able to sit in the audience. Advaita Ācārya, Śrīvāsa Paṇḍita and others sadly said that since they had no control over their senses they would be ineligible to watch. Mahāprabhu laughed slightly at hearing this and said that everyone would become a great yogi and would not be bewildered by His performance.

Śacī Mātā and Viṣṇupriya Devī also came to see Mahāprabhu dance as Lakṣmī, and so did all the other devotees with their families. Advaita Ācārya took the role of the vidūṣaka or clown, while Haridāsa Ṭhākura played the role of the town constable and Śrīvāsa Paṇḍita dressed up as Nārada Muni. The performance began when Mukunda sang Kṛṣṇa-kīrtana. Haridāsa Ṭhākura came dancing in, twirling his baton, and he told everyone to watch the play and the Lord’s dancing attentively.

Śrīvāsa Paṇḍita in the role of Nārada Muni said, “I have been wandering through the universes hoping to get a glimpse of Kṛṣṇa. I went to Vaikuṇṭha, but found the door closed and the house empty. Then I heard that Kṛṣṇa had come to Nadia and had dressed up as Lakṣmī.” When Śacī saw Śrīvāsa in his identity as Nārada she fainted in her amazement, but the other women brought her back to consciousness by chanting the Name of Kṛṣṇa.

In the next act, Mahāprabhu came out dressed as Rukmiṇī. Totally absorbed in the mood of Rukmiṇī, He recited from Bhāgavatam the letter she wrote to Kṛṣṇa, and as He did so, He cried and wrote on the ground with His toes. When the Vaiṣṇavas saw this scene, they were overwhelmed by the ecstasy of divine love.

Later on in the evening, Śrīla Gadādhara Paṇḍita Gosvāmī came onto the stage dressed as a gopī and began to dance like a woman in love. Mahāprabhu and Nityānanda Prabhu then entered the stage area, Mahāprabhu in the dress of the ādyā-śakti and Nityānanda Prabhu as an old woman, Rādhā’s maternal grandmother. As the members of the audience looked at Mahāprabhu, each beheld Him according to his or her own mood: some as Kamalā, some as Lakṣmī, others as Sītā and yet others as Mahāmāyā. Even those who had known Nimāi since His birth, including Śacī, were unable to recognize Him. In the guise of playing the roles of all the different goddesses, Mahāprabhu revealed His divine energies and taught the proper respect due to each one of them. While the Lord was thus dancing as the ādyā-śakti, Nityānanda Prabhu fainted and all the other devotees began to cry loudly.

Then the Lord revealed another amazing pastime: He took on the mood of Mahālakṣmī, sat down on the deity throne and placed the Gopīnātha deity on His lap. When the devotees saw this they began to sing hymns of praise to Mahālakṣmī. As this was going on, day suddenly broke and the devotees were saddened to know that the wonderful night had come to an end. When the Lord saw their sadness, He took the form of the Mother of the Universe and one by one, took all the devotees on His lap and fed them with His breast milk. The devotees’ sadness disappeared in a moment.

By the Lord’s inconceivable potencies, there remained a divine light in Candraśekhara’s house for seven days and nights afterward. It was so bright that people were not able to open their eyes to look at it. When people asked what this light was, the Vaiṣṇavas would only smile in response.

Candraśekhara Ācārya was also present in the saṅkīrtana procession Mahāprabhu led through Navadvīpa to Cānda Kāzī’s house to deliver him. He was also present when Mahāprabhu took sannyāsa in Katwa, and he performed all the rituals on His behest at that time.

So saying, Keśava Bhāratī went to Katwa. Mahāprabhu followed later to take sannyāsa. Nityānanda Prabhu, Mukunda Datta and Candraśekhara Ācārya accompanied Him and performed all the rituals. (Caitanya Caritāmṛta 1.17.272-3)

Afterwards, Mahāprabhu became frantic to see Vṛndāvana and set off in that direction. However, Nityānanda Prabhu tricked Him into going to the bank of the Ganges opposite Śāntipura. Candraśekhara Ācārya gave the message of Mahāprabhu’s sannyāsa for the people of Navadvīpa and Śāntipura.

The children showed Mahāprabhu the way to the Ganges, and He set off in that direction, completely absorbed in the consciousness of Kṛṣṇa. Nityānanda Prabhu said to Candraśekhara, “Go immediately to Advaita Ācārya and tell Him that I am coming there with the Lord. Tell Him to wait for us with a boat at the bank. Then go to Navadvīpa and fetch Śacī Mātā and the devotees.” (Caitanya Caritāmṛta 2.3.19-22)

Candraśekhara Ācārya did as he was commanded and brought Śacī Mātā to Advaita Ācārya’s house in a palanquin. The Navadvīpa devotees also accompanied them.

In the morning, Ācāryaratna put Śacī in a palanquin and set off to Śāntipura in the company of the other devotees. (Caitanya Caritāmṛta 2.3.137)

Later, when Mahāprabhu came back from South India to Purī, He sent Kālā Kṛṣṇadāsa (whom He had rescued from the bhattahari women) with Nityānanda Prabhu and some other devotees to inform the Bengali Vaiṣṇavas of His return. Kālā Kṛṣṇadāsa met with Candraśekhara on that occasion. Candraśekhara also regularly accompanied the other devotees to Purī to spend cāturmāsya with Mahāprabhu. He participated with Him in all the pastimes there, such as cleaning the Guṇḍicā temple and playing water sports in Narendra Sarovara.