Slowly increase the size of jewelry you wear in your ear. Most ears are pierced with an 18-gauge piercing gun or needle. This smaller size is easy to manage and does not require much tissue removal. If you wish to increase the size of the hole, you can buy and insert the next-size-up jewelry carefully into your ear. You can get larger jewelry online or at your local piercing shop. If you have an 18-gauge piece in your ear, buy a 16-gauge earring to slowly open the hole. As you get bigger and bigger, keep the existing jewelry in your ear for at least a week, if not a month, to get your skin to adjust to the stretching process. The advantage of this process is that you can stop at any size and compare sizes as they are in your ear.
Use a tapered needle or ring to increase the size of your ear hole. This is a safe way of increasing the size of your hole yourself without doing any permanent damage. If you do not feel confident doing this at home, go to a professionally-licensed piercer in your area. Insert the needle into your existing hole and gradually push the needle to the desired size. Be careful to not go too far or increase your hole too much in one sitting as it can cause damage as well as an accumulation of scar tissue.
Go to a piercing shop in your area to get the work you are interested done on your ear. There are licensed professionals at these shops who know the ins and outs of piercing and can evaluate the current state of your ear and make a recommendation based on that. He may be inclined to use a tapered needle or see if you can have larger jewelry inserted over time. Although it will cost more to have it professionally stretched, this action may prevent damage from lack of expertise in this area.