Have you considered a harness and leash training him? I am a FIRM indoor kitty person too, but it CAN be done if you have one that is adamant about going outside once in awhile. (Like mine
)
My "girls" were raised indoors and were terrified anytime they had to leave the house. But my boy was an outdoor kitty who was abandoned. He is now almost 5 years old and he still loves his "outside time"
The girls would always watch him from inside like he was crazy!
He goes out for a short time several times a day in his harness on a 15ft lead attached to my door. We have a fenced yard and I always
ALWAYS leave the doors and windows open so I can hear if another animal gets in the yard. (It has only happened once and I think that poor dog was permanently traumatized by the screaming cat and the crazy lady who flew out the door screaming louder than the cat!!
)
I made sure that there is nothing he can get tangled in, or jump over. When I have the time I just take him for a walk (just like a dog.
) He loves it and I don't have to listen to his non-stop complaining!
One happy but SAFE kitty:
http://i61.photobucket.com/albums/h61/jimeezlady/toes1.jpg (broken link)
Notice the tongue hanging out...pure bliss!
http://i61.photobucket.com/albums/h61/jimeezlady/toes3.jpg (broken link)
Yes, he has to be brushed before he comes back in!
http://i61.photobucket.com/albums/h61/jimeezlady/toes2.jpg (broken link)
Harness training takes time and patience...start with very short periods and take him outside EVERY time you put it on him... pretty soon he will learn that if he wants out he has to put on the harness.
Mine walks to the door now and yowls to go out, when I slip the harness over his head he steps into the leg section on his own and waits for me to snap it.
Never leave him outdoors attached to a lead unsupervised! If anything happens he would be trapped and unable to run away.