To stretch or not to stretch!?

I've been seriously contemplating stretching my ears over the past year or so and need some reassurance. I put tapers in once, but it gave me a terrible headache and I didn't really have the necessary equipment, so I gave up that easily. Gauges and tapers and pretty expensive and I'm on a "no buying 'stuff'" ban, so there's another problem I'm having. I could always make my own, but I don't want to screw anything up. I have 14 piercings already, none too obvious, but I am always wanting more. I think stretching my ears will be a good way to keep things interesting without getting more and more holes in my body haha.

Does anyone have any advice for me? To stretch or not to stretch? Does it hurt as bad as I thought it did the first time? Where do you buy your gauges and tapers?

Hope your day is asastonishing as you are.<3