Internet of Medical Things is the internet connection of medical devices to perform services and processes to support the healthcare sector. Wearable Technology in Healthcare has seen tremendous growth in recent times. This is due to a global increase in the aging population, the need for disease management, and effective patient monitoring. The prevalent technology of wearable devices is Bluetooth technology due to its low cost, low energy, and size. Despite the growth recorded in the adoption of Bluetooth Wearable IoMT, there are concerns by users and other healthcare stakeholders about security and privacy issues with its adoption. Our paper presents a simulation of passive and active attacks on 3 wearable IoMT devices, followed by analysis and evaluation of the experiment outcomes. Thereafter, countermeasures for the identified weaknesses were provided. It was discovered that some of the standard security features of Bluetooth Technology to mitigate privacy and security issues were not implemented in some of the devices, which can result in data compromise in the devices. A security assessment framework was developed to assess the security of Bluetooth IoMT devices using the Bayesian Network model. This is used to rank devices, identify their vulnerabilities, and apply security measures on the identified vulnerabilities. Our paper further provides recommendations on improving the security of Bluetooth IoMT devices.