I cuddled my kitties as much as I could when I first got them (rescued at 3 weeks old). They are now a bit over a year old. While Neo loves to be held and cuddled, Sapphire hates it. She will be very aggressive when she wants to be petted (rubbing against my hand over and over), but will not be held. Sometimes the personality of the cat gets in the way.
Just keep doing it frequently, but DON'T do it for any longer than he's willing to allow it. If you force him against his will, then he associates it with something he doesn't enjoy. If you just keep doing it and make it pleasant and allow him to come and go, then he'll get used to cuddling on your lap for longer and longer. That being said, some cats just never want to cuddle, no matter what. But just keep working on it and more than likely things will improve for you.
Abby loved to be cuddled when she was a kitten. But as a 7 year old adult she only cuddles on her terms... basically when she wants to. She doesn't like it when I tower over her and try and pick her up... I don't blame her. To a cat on the floor we're giants! Sometimes she will suffer herself to allow me to pick her up and hold her...but I can tell she's only tolerating it for my sake. I keep telling her that it's not fair that I can only get cuddles when she wants to, and that cuddles are a two way street, LOL.
Some cats just aren't cuddlers, just like some people aren't.
Never restrain a cat. If it wants to go let it go otherwise it will feel unsafe. The idea is to make your lap a place where kitty feels loved and safe.