D.P.
Why don't you try a sippy cup with handles first so he can feel for that first and get the idea. If that works, slowly move on. Maybe try a plastic coffee mug that has handles too. You'll be surprised how good he might actually be with a bigger cup then. My youngest will be 3 next month and thanks to her sisters, she caught on quickly (before I was ready!). A lot of times though I save the plastic cups from restaurants that have the lids and let her use those with straws because kids will be kids and do spill things and this makes things easier. Kids love straws! Just be patient and keep trying. You can also try using the kids juice box style first just to get him away from the sippy cup. Kids are thrilled with these too. Good luck.