in the community, we hear a lot about comfort - that self-confidence is comfort with oneself and you need to build comfort to get her clothes off.
first, no matter what you do, you cannot make her comfortable. she makes herself comfortable, so forget about making her comfortable.
but you can make yourself comfortable. so how do you make yourself comfortable? in the same way you make yourself comfortable in anything else you do, such as lying in a new bed or wearing a pair of new jeans - you get familiar with your surroundings. but to what extent? after all, in a bed, your head lies on the pillow and at the head, not the foot of the bed. there's no point resting your head at the bottom in order to "get familiar" with that bed. and with jeans, there's only one way to wear them. you don't wear them inside out in order to get familiar with them. they stretch and fit the way you use them. they adapt to you and your needs.
it's the same with women. do what you want to do. it sounds easy, because it is. think of it in terms of comfort zones. with something or someone new, your comfort zone is very small. to get more comfortable, you need to stretch your comfort zone.
stretch a little or stretch a lot, depending on how fragile you think something is. start by looking at her, next saying that little joke you want to say but aren't sure is appropriate. then move to touching, see how it feels. keep doing and saying things you'd say anyway, but aren't sure is okay because you are completely familiar with this person's sense of humor, sensibility, etc. you might stretch yourself into something sexual if you're feeling it, you might not. neither is right or wrong.
but you keep stretching your comfort zone until you are able to do exactly what you want when you want without questioning yourself. your bed doesn't judge you for sleeping the way you do. and neither should your woman. you don't adapt to her. she adapts to you.