Youngster doesn't like tail being brushed

FinkleyAlex

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My rising 5yo has decided he doesn't like his tail being brushed - I've no idea why as I've owned him since he was a yearling and he's never had an issue with it before. I've spent the last 8 months handling him as minimally as possible as he was over-handled during a period where he was briefly sold and bought back by me. Since doing that he's developed a real thing about his tail - he tenses when I lift it to put his fillet string under it and if I brush it he gets incredibly tense, will stop eating his hay and has tried lifting a foot to warn me that its a precursor to a kick. I make sure to tell him that's unacceptable behaviour and give him a good growl and in fairness to him he's never actually tried to kick, he just keeps his leg on the ground at a certain angle! I build up to it by giving him a good groom everywhere (which he enjoys) and I only take a little piece of his tail at a time to brush (tried using a body brush and a plastic curry comb - no difference) and I always make sure to hold it from the top so it doesn't pull at him while I brush. He lets me take little pieces like this but as soon as he feels I have his whole tail in my hands or if I try to brush his dock area he gets very tense and agitated. He won't eat his hay at all while I'm doing his tail so he's obviously not putting it on (biggest food motivated animal I've ever met!). I've tried doing little and often, I've tried persisting all in one go. He lets me do it but is not at all happy with it, and despite standing at a 90 degree angle to him I never quite trust him. Any ideas on how to get over this?
 
Sounds like a pain response to me if he has previously been fine to handle
I'd be tempted to get him checked by a vet.
 
Should probably have mentioned I had the vet out yesterday to do his jabs and I told her about it and she laughed it off saying he was just being a baby. He had the saddler today and his back was a bit twitchy so I'll be getting the back person out next
 
You say you hold the hair at the top, but do you try and brush the whole length at once, or do a couple of inches at a time? As a child with long hair I hated mother brushing it, but was happy wth father brushing as he was careful not to collect all the knots up and try and drag them out.
 
I only do a little bit at a time - like how a hairdresser would, bottom first and work up. I managed to get his whole tail done via little sections at a time but when I put him back in his stable he wouldn't let me near him after!
 
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