May I recommend the BVT Kitty Relocation service?
I ain't going to go there, and I ain't gonna go there!
Boston, I have three cats. One of them gets into this nighttime kneeding routine from time to time. I kick him off the bed. It's hard to get a good shot at him from under two blankets and a comforter, but he usually gets the idea.
Otherwise, the others are right. Indoor cats will outlast an outdoor by up to 15 years. If you insist on letting him out, though, wait till he's been in his present home for at least a month. Cats like the familiar, and if the outdoors where you are at is not familiar, Bossy is going to start looking for the old homestead.
Just in case he hasn't been neutered, get it done soon. An unneutered cat in the house, of either sex, is almost impossible to live with.