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Hi, this is Dr. Gabby. Are you sure he is not straining to urinate? Urinary tract infections and inflammation are very common in male cats. They can also cause the cat to vomit due to pain and stress. So I would make sure he is urinating normally first.
I would not give a stool softener unless he is constipated. If he is constipated the stools will be very hard and dry. So check the stool he just passed.
If you are still sure you want to give something for constipation I would start with 1/2 a teaspoon of human Miralax powder mixed with food. You can also try a few spoonfuls of real canned pumpkin.
If he has an upset stomach, and is vomiting, then you can give him 1/4 of a human Pepcid Ac talet every 12 hours and feed him a bland diet of plain cooked chicken.
But again, check his urination because that sounds like that may be the cause. If his urinary tract becomes blocked and he is not able to pass any urine at all then he needs to see the emergency vet as once as it is a medical emergency and life threatening.
Does that help? Do you have any additional questions?