Scarleteen

Basically, when I touch/rub my clitoris it feels nice instantly but then get really uncomfortable and my brain sorta forces me to stop. It’s not painful, it’s actually very hard to describe the sensation but I always make myself stop. If I masturbate with a pillow or a cushion is different and it actually works and feel comfortable and I’m not sure what the difference is because I touch the same thing though the pillow. I don’t stop myself out of guilt or as if it’s wrong to masturbate. I’ve actually been masturbate from a younger age than average (I think) I was 10 when I started. So to sum this up why do I always, without meaning, stop myself from rubbing my clitoris but only if it’s just my hand ?

It could be that touching your clitoris directly is causing a lot more intense sensation, since your hand or finger can deliver much more focused and targeted contact than something larger and softer, like a pillow, can. If that's the case, and the direct contact feels too intense, you might find that using a little bit of lubricant helps; that will cut down on friction and may make the feeling a little more comfortable.
Some people just don't like the feeling of direct clitoral sensation and prefer something like using a pillow, as you describe, or touching through the clitoral hood, rubbing at it from the side, etc. so they can have some slightly-indirect contact. Those things might be worth a try, if you haven't done so already.