Rembering that even the most sluggish cat is capable of eluding their owner at any given time, I think you need to make sure that the area is completely secure. Otherwise he may be chasing a bug, bird or squirrel and you won't be able to catch him.
As for his fear, I would say that he needs to approach going outside on his own, rather than having you carry him out. Leave the door open and you go stand outside to encourage him to come out. Maybe have some treats with you.
But be prepared...once he likes it outside, he is likely to become a door dasher.
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Holly, Misty & their friend, Jake, the dog.
Onyx, Callie May, Maggie & Kobi forever in my heart.
Yes, I know I need a new signature pic...someday...