A wireless communications system comprising: a user-wearable device comprising a clasp having open and closed positions, a first wireless security circuit, and a first controller coupled to said clasp and said first wireless security circuit; and a mobile wireless communications device comprising a portable housing, at least one input device, a second wireless security circuit carried by said portable housing and configured to communicate with said first wireless security circuit when in close proximity therewith, and a second controller carried by said portable housing, coupled to said second wireless security circuit and said at least one input device and configured to upon a first initiation of communications between the first and second wireless security circuits, determine the position of the clasp and enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device, and upon subsequent occurrences of communications between the first and second wireless security circuits, bypass the manual entry requirement and enable at least one function based upon a communication from said user-wearable device and said clasp remaining in the closed position, else enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device. a user-wearable device comprising a clasp having open and closed positions, a first wireless security circuit, and a first controller coupled to said clasp and said first wireless security circuit; and a clasp having open and closed positions, a first wireless security circuit, and a first controller coupled to said clasp and said first wireless security circuit; and a mobile wireless communications device comprising a portable housing, at least one input device, a second wireless security circuit carried by said portable housing and configured to communicate with said first wireless security circuit when in close proximity therewith, and a second controller carried by said portable housing, coupled to said second wireless security circuit and said at least one input device and configured to upon a first initiation of communications between the first and second wireless security circuits, determine the position of the clasp and enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device, and upon subsequent occurrences of communications between the first and second wireless security circuits, bypass the manual entry requirement and enable at least one function based upon a communication from said user-wearable device and said clasp remaining in the closed position, else enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device. a portable housing, at least one input device, a second wireless security circuit carried by said portable housing and configured to communicate with said first wireless security circuit when in close proximity therewith, and a second controller carried by said portable housing, coupled to said second wireless security circuit and said at least one input device and configured to upon a first initiation of communications between the first and second wireless security circuits, determine the position of the clasp and enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device, and upon subsequent occurrences of communications between the first and second wireless security circuits, bypass the manual entry requirement and enable at least one function based upon a communication from said user-wearable device and said clasp remaining in the closed position, upon a first initiation of communications between the first and second wireless security circuits, determine the position of the clasp and enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device, and upon subsequent occurrences of communications between the first and second wireless security circuits, bypass the manual entry requirement and enable at least one function based upon a communication from said user-wearable device and said clasp remaining in the closed position, else enable at least one function of said mobile wireless communications device based upon a manual entry requirement of an authentication code via said at least one input device.