Portable, hand-held electronic devices for and methods to enabling a user to interact with a native operating system (OS) running on a host device and a virtual machine running on top of the native OS are presented. The host device includes a processor to communicate with an application having a target network address. The devices includes an onboard database that stores user credential information and a portable encryption and authentication service module (PPEASM) that allows to make a secure communication channel with the host device. The PPEASM configures the processor to negotiate authentication of the user with an application running on top of the native OS utilizing the user credential information, render an application running on top of the virtual machine, and pass data between the application running on top of the virtual machine and a second application running on top of the native OS.