1. The deriving of technological gratification, or the tendency to derive technological gratification, from being unskilled in or misusing technology.
2. The deriving of pleasure, or the tendency to derive pleasure, from causing and/or enduring technological problems.
3. A willingness or tendency to subject oneself to unpleasant or trying experiences, through the unintentional or intentional misuse of technology to the point at which it becomes inoperable or unusable.
Example: Billy is such a technomasochist that he fell for yet another phishing attempt and had his Yahoo account hacked for the seventeenth time this month.
(Source: @GeekShui, July 29, 2013)