The idea of video production company began as an offshoot of latex and fetish clothing company, WhiplashUSA. Robert Zak, the owner of Whiplash, met young filmmaker John Fitzgerald and, after sharing their passion for kink, decided to venture into fetish film production.
After teaming up with Isabella Sinclaire, the 3 collaborated on the idea of working together and dubbed GwenMedia after John Willie's Sweet Gwendoline, which was a favorite book of Isabella and John. The company began a trial project, "Part-Time", during a trip to AVN in Las Vegas. Though the process would prove to be challenging, it quickly became obvious that this was the type of film they wanted to make.
A few weeks later, The Ivy Manor series was born. Within the first two installments of this benchmark series, the Ivy Manor films quickly set an industry benchmark for visual and fetish style, garnering numerous accolades from publications such as Skin Two, AVN and Taboo.
In late 2002, after writing, directing and photographing GwenMedia's first eight videos, Fitzgerald left the company to pursue other interests. Zak and Isabella soldered on, producing a wide variety of titles, including the Crimson Mansion series, the Rubberella series and many more. After Robert Zak's untimely death in 2005, Isabella Sinclaire gained control of the company, and is now making GwenMedia shine once again.