I am indebted to Roy D for reminding me of this splendid, rustic 'Wedge' by Stephen (aka Etienne). It's from his 'Hot Broncs' group of 6 cowboy pictures and is one of his better drawings with some excellent detail, like the tumbled heap of clothes and background scenery. The two bullies having a laugh at the young (and improbably cute) Sheriff's expense are also depicted rather well, showing a nice bit of male bonding.
I love the way the captive's feet are tied to the stretcher underneath to prevent escape, something similar happens in the Bound Gods examples I posted earlier. The nipple clamp/cock ring device naturally captures the viewer's attention but the little, spiky branchlet sticking out underneath hints at other discomforts Stephen might have profitably explored instead.
To make it easier to read these scattered posts I have added a new label 'riding the wedge', just click on it below to see the complete set of entries.