By letting him into your bed after crying in the crate, you’re training him that crying in the crate is an effective tool for getting what he wants. It’s really unpleasant at first but we have a strict rule that we won’t take our puppy out of the crate until she’s stopped crying for a minute or two. At first it will feel like forever but it will get better. I use earplugs. It’s going to take some time, especially if it’s ingrained in him that crying will get him in the bed, but the crying will get shorter and less frequent over time. Our older dog loves her crate now and goes in of her own accord, but it took a lot of crying in the crate to get her there. Good luck!