crop duster

I have a 1995 Chevy 1500 extended cab 4x4 pickup. It has 258,000 miles on it and it runs pretty well for what it is. The CEL does come and go multiple times while just cruising down the road but it does not seem to affect how it runs or drives.

But I'm having some problems with the transmission. Sometimes when I start the pickup and put it into drive it is a very hard firm shift and the pickup lurches and it goes into drive with my foot on the brake. This is my first clue that I'm going to have this issue. What happens next is that as I drive my shift from 1-2 is very delayed with RPMs around 2600 before it will shift. And when it does decide to shift it is very hard and firm. The 2-3 shift is also delayed but it is not quite as violent. Then then 3-4 is a bit better.

Now this problem is sporadic. If I shut the truck off and restart it there is a chance that it will go away and run and shift fine. So what I have started doing is when I put it in drive after starting and it has the lurch and hard shift into drive then I go back to park and shut it off. Sometimes it will take me doing that 3 or 4 times but it will eventually go into drive normally and smoothly. At that point I know it will shift fine and I go ahead and drive it. When it works normally the transmission shifts great and it's very smooth.

Any idea what could be going on? Thank you for any help.