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How to explain: he needs his Boots and Bar

Last night I opened up about how hard I'm finding Hugo's Boots & Bar at the moment he's 19 months old & finding his voice. He can tell me now when he's unhappy & he's determined that at this present time he doesn't love or even like to wear his boots especially the metal bar. I took last night really hard, after I had a good cry (Hugo didn't see me express any sought of emotion) I hadn't really thought what the next nights would be like... 
Well tonight went something like this: 
We arrived In Norfolk; we are staying with my gran (the babies great gran) they both love it here & although its almost 5 hours away in the car it most definitely feels like their second home. We had dinner late so I let Hugo have an extra hour feet free time. By 7pm I thought it was about time to put his BnB on well Hugo had totally different idea & after chasing him round for 10 minutes I tried to put him in his high chair (normally a good place to put BnB on) but he screams as I tried to put him in.  Then gave him to his grandad to hold him he happily sat on grandad's lap until I showed him his socks & BnB then a tantrum escalated ... Humph. 
It's the most heart breaking thing, how do you explain to a 1 year old your only trying to help? 
I had a good look at his feet & they are covered in sores (new boots longer bar) it happens. Typically though I have no compeed plasters with me... A trip to the pharmacy tomorrow. No wonder he's been kicking up such a fuss. It feels like child abuse forcing his feet into a boot that's actually causing him pain. 
You know on a night out when your in heels & your feet are so cut up all you want to do is live in slippers for the following week? Well that. My poor poppet. 
We managed to get his BnB on with a joint effort from my Mum & I... Mum had finger puppets trying her best to distract him... 
The next few hours went by is a screaming blur (Hugo screaming not me) just making that clear... 
& now here I am it's 9:50pm Hugo is on my chest fast asleep he's not slept on me like this since he was a tiny baby. He must of needed Mummy comfort. 
I'm in two minds whether to put him in his cot or not? 
I knew when I found out Hugo had talipes that we will have a roller coaster ride but I'm stumped with what the best way to go with this at the moment. 
It's a definite NO NO to wait till he's asleep & then put them on I know that so I won't even attempt that... 

I'm just going to pray that it gets better. Heck I've got the next 4 years with his boots & bar we need to find something that makes him love them.
Negativity will get us no where. 
Positivity is the key!