I feel like this question HAS to have been asked before, but I went through the education tags, as well as Victorian era tags looking to see if anyone has asked anything similar and didn't find anything helpful...
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Question under cut because it could be potentially triggering )
If your man hasn't done caning before, I'm quite sure he won't be able to deliver really heave strokes right way. It's quite easy with the cane to get the aim wrong - especially when sweeping it from far away, to gather a lot of motion energy for the hit - and hit too high (lower back, kidney area) or too far below (corner between ass and upper thighs, or upper thighs). So either he risks the first blows to come down quite wrong in place, or he's a bit more tentative with the first ones.
It takes a bit of practice to deliver them really to the point, so I'd expect them to cover a range on the ass anyway, which makes it possibly less painful for the kid.
If the strokes hit all the same small area, the most prominent areas can easily get very hard and gain that leather feel. But when it's a range, you're likely to see more of the single cane strokes. It's quite painful during the caning, as the young man isn't in any way prepared, so all strokes will bite. He'll likely cry out (unless he's the kind of man to bite it down, many men are very quiet). There may be (silent) tears. There also may be a lot of anger and resistance against the punishment and the man who delivers it. In your setting the humiliation aspect might actually 'bite' a lot more than the caning.
Afterwards, it's a heated/pulsing feeling. People are usually able to sit down soon afterwards. I'd say this picture would be resonable for 15 strokes:
spankingtube.com.ar/videos/wp-content/uploads/2011/07/Gorgeous-Caned-Ass.jpg
This would need probably more strokes, so it's kind of upper limit I'd assume in your scenario:
lh5.googleusercontent.com/-k_s8SC_xUa0/TXeQUHV1BjI/AAAAAAAABaU/CF8kytE4r4A/red+bottom+caned_07.jpg
There might be a bit of blood but usually only punctual, because often the skin has some small pimples that can open under the caning.
As for permanent damage, I think not, unless he'd receive very heavy strokes on the kidneys. There will be bruises that can turn very colorful but I only knew one person with clotting problems, and she had a gigantic medical backstory regarding that subject. There's a reason why punishing was often restricted to the ass, it's one of the most padded areas with no nerves to damage easily.
If you've got any more questions, ask ahead :)
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When a caning is done as a punishment, humiliation is the greater bite than the cane itself. Some of the humiliation comes from the knowledge that one put oneself in the postition of requiring a punishment caning.
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