Virtual reality systems may benefit from wearable (fingertip-mounted) haptic displays capable of rendering the softness of virtual objects. According to neurophysiological evidence, the easiest reliable way to render a virtual softness is to generate purely tactile (as opposed to kinaesthetic) feedback to be delivered via a finger-pulp-interfaced deformable surface. Moreover, it is necessary to control not only the skin indentation depth by applying quasi-static (non-vibratory) contact pressures, but also the skin contact area. This is typically impossible with available devices, even with those that can vary the contact area, because the latter cannot be controlled due to the complexity of sensing it at high resolutions. This causes indetermination on an important tactile cue to render softness. Here, we present a technology that allows the contact area to be open-loop controlled via personalised optical calibrations. We demonstrate the solution on a modified, pneumatic wearable tactile display of softness previously described by us, consisting of a small chamber containing a transparent membrane inflated against the finger pulp. A window on the device allowed for monitoring the skin contact area with a camera from an external unit to generate a calibration curve by processing photos of the skin membrane interface at different pressures. The solution was validated by comparisons with an ink-stain-based method. Moreover, to avoid manual calibrations, a preliminary automated procedure was developed. This calibration strategy may be applied also to other kinds of displays where finger pulps are in contact with transparent deformable structures.