For our fourth secretary spanking, we have this piece by Homer (as he signed his work, although the signature is missing here). No caption, so we're not sure what the pretext for this spanking is, but the boss sure looks like he's having fun, and the secretary doesn't seem to mind too much. Homer didn't publish as many cartoons in men's humor mags as did Bill Ward or Kirk Styles, but we remember seeing perhaps 5 or 6 of his that were spanking-themed. Stylistically, he tended to draw flatter bottoms than Ward and the others, and his spankees' faces are always intelligent as well as pretty - you never have the impression that they've been duped by the spanker, as you sometimes do with Styles (see here, for example).

Next Entry

No discussion of secretary spanking could be complete without mentioning the movie Secretary (2002), destined to go down in spanking history as the first mainstream film that went beyond just featuring an incidental OTK whack or two and instead based its plot around a consensual D/S relationship. How healthy this relationship was is another matter, but while we don't have the space here to go into that subject in detail, we do think it's reasonable to conclude that given the two personalities involved were unlikely to change, their relationship was mutually beneficial and not exploitative - it wasn't a case of a vulnerable girl being used by her sadistic boss.

The movie poster at left is probably our all-time favorite (wonder why?), and was actually used to promote the film. A tamer version for timid retailers which was cropped above the knee also appeared and was used on the DVD box, for example. Unfortunately, the holding-ankles position was not used in the film itself, but you can't have everything.

In this scene, James Spader bends Maggie Gyllenhaal over the desk and spanks her by hand. This position really cries out for a nice wooden or leather paddle, but a fine scene nonetheless. The rationale for the spanking is that he's a stickler for perfect typing, and she has made some typing errors in the letter seen on the desk in front of her. What a fun idea! And it's a recurring motif among secretary spanking cartoons, as we will see.