A mode division multiplexing (MDM) chaotic encryption scheme based on key intertwining and accompanying transmission is proposed in this paper. Based on the weakly coupled few-mode fiber (FMF), data and time-varying keys can be accompanied by transmission in two modes, LP01 and LP11, respectively. In order to generate a new key, the current key is XORed with all of the keys from all the preceding moments, one by one. To implement chaotic masking in the digital domain, the three chaotic sequences corresponding to the new key are adopted to encrypt the data at the constellation phase, data symbol block, and subcarrier levels. An 8.89 Gb/s encrypted 16QAM-OFDM signal transmission over 1 km weakly-coupled FMF is experimentally demonstrated. The receiver with the correct key can recover the data normally, while the BER of the illegal receiver remains around 0.5. In the case of the key transmission bit rate of 1 Gb/s, the cracking efficiency threshold of the time-varying key encryption scheme is 5.21 × 106 times that of the time-invariant key encryption scheme, which suggests that the proposed work is a promising candidate for future physical layer security.