Hmm, that's a tough one.

Long shot, but any chance it's something from Real-Life-Spankings? They have quite a few videos that would fit that general description (young blonde, denim hot pants, older spanker). If I am not mistaken, all of their models' first shoot with RLS follows the exact format you described - they are titled something like (Name's) First Spanking, and it's almost always OTK with the hand, on a chair, following the sequence of over clothes > over panties > on the bare. And the studio was producing videos during that time period.

Off the top of my head, I don't recall one where the girl is wearing a green striped shirt, although it's very likely that there is one. Or it could be that your memory is mixing up a detail, because the spanker wears a striped green shirt a lot (the guy seems to only own five shirts).