Recently, remote meetings and work-from-home have become more common, reducing the opportunities for face-to-face communication. To facilitate communication among remote workers, researchers have focused on virtual space technology and spatial augmented reality technology. Although these technologies can enhance immersiveness in collaborative work, they face the challenge of fostering a sense of physical contact. In this work, we aimed to foster a sense of presence through haptic stimulation using pneumatic actuators. Specifically, we developed a choker-type wearable device that presents various pressure patterns around the neck; the pattern presented depends on the message the device must convey. Various combinations of haptic presentation are achieved by pumping air to the multiple pneumatic actuators attached to the choker. In addition, we conducted experiments involving actuators of different shapes to optimize the haptic presentation. When linked with a smartphone, the proposed device can present pressure patterns to indicate incoming calls and notifications, to give warning about an obstacle that one who is texting might miss while walking, and to provide direction to a pedestrian. Furthermore, the device can be used in a wide range of applications, from those necessary in daily living to those that enhance one’s experience in the realm of entertainment. For example, haptic feedback that synchronizes with the presence of a singer or with the rhythm of a song one listens to or with a performer’s movements during a stage performance will immerse users in an enjoyable experience.