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Thank you all for your replies!
I've got some good ideas now.
I'm going to go shopping and see if I can buy seemless socks, didn't even know there was such a thing!
Going to my local book shop to see if they have the books mentioned.
I'm going to file his toe nails so there isn't any sharp bits.
And then, when he comes home from school, I will show him this post so he knows that he isn't alone.

Had a bit of luck this morning, I massaged his toes with lotion just before I put his socks on. He actually said it felt nice, for 2 minutes, then he took his shoe on and off whilst he screamed that 'it's gone wrong'.
But, he kept the sock on! this is a first.

Thanks again for all the suggestions, it really is appreciated.
x

ICK! that would be the worst EVER in our world. Have you seen all the crap that comes in through those holes...ick! little pebbles, bits of sand, dirts, etc! I have seen kids feet after wearing those and man! those are filthy! It would make me WANT to wear socks!! !! !!

Not to mention how unattractive I find them...*shakes head*

Have you ever tried having him wear different kinds of socks? When I was a kid my mom could never get me to wear a pair of socks no matter what she did. Punishment or rewards didn't work on me at all. Then one day I was at my cousin's house and my aunt was getting us ready to go home. I noticed my cousin was wearing a pair of socks that went over her ankles and I asked her if I could try them on. My mom had only bought me ankle socks before but I immediantly loved the higher socks. I now have quite a collection of socks all above my ankles. I particularly love knee socks.

Try dress socks, one made of a silk blend, they are smoother and softer than cotton.

I hate wearing socks, mostly because when I do it makes my entire leg hurt, whenever I do I try to make then short socks a size or two too large. My husband on the other hand likes knee highs so tight they leave a centemeter deep impression in his skin ((ouch!))