How best encourage my cat to go outdoors?

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My cat is a 10-month-old neutered male. He came to us as a barn cat when he was 8 weeks old. He hid for weeks before learning to trust us. All summer and fall he refused to go out and now has learned to sit in an open window. His forays on the ground below the window are very short.

His reluctance surprises me as he is extremely frisky and can even be a bit aggressive. Personally I think his hunter nature (he is forever chasing after things) has gotten the better of him and at some level, he knows he could be hunted himself if he goes out into the open. We have a yard but live near a forest where there are cougars. Other cats in the neighbourhood go out all the time. When he sees one he tends to want to attack. He is quite alpha. I would like to see him go out during the day when the cougars are not an issue. How to encourage him? Someone in the family has a bee allergy so once spring really kicks in, I won't be able to leave the window open for very long anymore. Suggestions?
Unfortunately a cat flap is not an option as our doors are metallic. Last year we did take him out in our arms and the moment we let him down, he bee-lined for the house every time. Since he has been going out every day for a few minutes, I am hoping he will feel more secure when we are out there with him. I am worried though that he will startle, run far and not know how to get home. Walking him on a lead might be the way to go though I can imagine that he will freak out big time if we see other cats on the way. Also, one immediate neighbour often has a large, aggressive dog in their front yard that is not tied up. If my cat caught wind of this dog, he would head for the hills for sure.
Well, because my cat is so frisky, I imagine that he could have a lot of fun outside and given the independent nature of cats, I really want him to be able to go out, learn to navigate in the bigger world and have fun. Maybe it's just too scary for him. Maybe if he does not want to be outside, I should continue to give him safe opportunities to be outdoors but let it go if he chooses security over all else.
 
What about getting a screen for the window? That would allow interaction for the cat, but no bees inside (I sympathize, I have a bad allergy too).

Just to let you know, cats have very short lives when allowed to go outside, versus indoor-only kitties.

It sounds as if he would be getting into lots of fights ("Other cats in the neighborhood go out all the time. When he sees one he tends to want to attack"). He will develop many sores and abscesses due to fighting (you see them all the time in outdoor cats), and there is always the chance he can get rabies from another cat during fighting.

All in all, I would invest in a screen, in order to keep both the allergy-filled person and the kitty safe.
 
Well, you could get a cat flap, you will just need to learn him to use it though, that's not too hard, just show him how it works when he is looking and eventually he will start to learn that this is what leads to the big world, or you could close the door, then your outside and he is inside looking at you through the cat flap, and then call him or entise him with some treats through the cat flap to you, then he will realise that he can push through the cat flap. The other thing you could do is when you go outside take him out there with you in your arms, even if he hates it it will make him fell alot safer if your there, leave the door open so he can get inside when he runs away, and if you keep doing this he'll eventually know that its ok, thirdly when your family member with the allergy isn't home, leave the doors open, he may if he's a bit frisky and agressive may go and investigate the new smells and looks of the outside, and eventually, bit by bit may learn himself that the outside is fun, or go outside without him, and just leave the door open so he can see you outdoors, he may then look at you as if to say what are you doing? But eventually he may come and greet you outside and know that if your outside then it's safe. I hope this helps.

Edit: Also, if your cat looks like he wants to be outdoors, don't not let him out, even if he dosn't want to be outdoors, any cat should be given a chance to see if he or she likes it, cats going outside and having little "arguments" about teritories and running around, there will be much less cats about around your house as your cat will not want other cats around you or their home, also bringing in catches like birds, is their teenage years of their lifes like we have our teenage years. There's nothing cuter than seeing your kitten bring in a leaf and thinking she or he has caught something that is alive, when really it's jsut blowing about in the wind and want to show you when they have it clutched in their mouth.
 
Go out with him. Buy a lead line and keep him on it for the first few times. Tie it up and let him romp around in your yard a bit, first few days sit out with him, next few days let him be out on his own. He'll get to go out but will be safe at the same time. At least this way you'll be able to see how he'll react being out doors, he'll be able to get used to his surroundings. Take him on a walk (as cheesy as that sounds) So he learns the way home. This will also allow you to see how long he wants to be out doors at a time and what it will take to get him back inside. Being called? Simply the door being opened? or will you have to go find him.

Good luck
 
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