Matthew Windsor shot his first ever porn video in 1989. The actor was credited in a total of 165 titles until his retirement in 2009. Matthew worked in a masturbation video for his first video project produced by Vivid titled Air Male. In 1990, he was featured in Carnival Tails along with Robert Reyn, Steve Kennedy and Tony Davis. Matthew Windsor also teamed up with Rebel Video in the 1998 film Hot Leather, Hard Men. Meanwhile, Totally Tight Video gave him a perfect role in their 1998 erotic video Working Man's Blues under the direction of William Hunter. He also played a bottom role in Extra Sex which was under the direction of Jeff Lawrence. Catch more of Matthew Windsor in the impressive roles he played in Fast Fuck Nation, Gay Ass Worship, Hungry Manholes and Butthole Bonanza.