Questions encouraged! If you need privacy, Anon is on or you can specify in your ask to answer privately, if necessary.
Hmmm! I’m not entirely sure I understand what you’re squeamish about, Anon…? (And I’m sorry if my brain is just not quite comprehending, masturbation came for me fairly young and sometimes I have difficulty relating.) Are you uncomfortable touching yourself and beginning to masturbate, or are you having difficulty specifically reaching orgasm?
If it’s the first, I would suggest approaching yourself as if your body were someone new. Don’t focus specifically on masturbating or orgasm, focus on getting to know your body, and what kind of touches you find enjoyable. You could try stroking your arms, your shoulders, your back, your stomach… If you like to take bubble baths or give yourself pedicures, you might do that. If you have never looked at your own genitals, you might do that also.
Then you can move towards touching yourself in specifically erotic ways, if and when you feel like it. If you have a partner, you might want to think about them, or situations you find erotic long before you want to touch yourself. Some people find that squeezing their upper thighs together creates a pleasant sensation, especially while they are thinking erotic thoughts.
It may or may not help you to look at erotic materials, but I’m a really, really big fan of Clean Sheets. I personally like pornography but I find a lot of women (especially younger women) feel uncomfortable with images, but text-based erotica is easier to digest. I think the best way to get into masturbation is to get aroused as possible before you start trying to touch yourself, especially if you’re squeamish about doing so. So whatever does that for you, do it.
The more relaxed an environment you can create for yourself the better.If you know how to mediate, you can try entering a meditative state while laying down naked before exploring your body. If you have a partner, you could see if they can give you a massage to help you relax. You might also tell them about how you are feeling nervous or squeamish, and tell them that what you really need is just reassurance about your body and how it might respond. (That conversation might feel stilted, but if you just say the words, most people will try to understand and accommodate.)
Masturbation is about self-pleasure and exploration, and there’s no right or wrong way to do it. If you don’t find certain sensations enjoyable, then don’t do them. A lot of people find stroking the clitoris more pleasurable than penetration, especially when they’re by themselves, but not everyone. Some specific physical sensations to try: Stroking your fingers over your clothed genitals, it’s much softer and less direct. Rolling your fingers over the hood of the clitoris. Tugging gently on the hairs or stroking the outer lips and upper thighs. Tapping lightly on the hood of the clitoris with the pad of your finger. Find what feels good.
You might also consider the environment or situation you’re in when you’re trying to masturbate. If you are worried about people hearing you or knowing what you’re doing, that could make you nervous. If you’re worried about what your body might do, what sounds it might make or whatever, that could also make you feel uncomfortable.
You might try masturbating, if you feel up to it, in the bathtub/bathroom, when nobody else is around or at home, so as to minimize the number of things you might be subconsciously embarrassed about.
The last thing I want to tell you is that it’s okay if you don’t orgasm. Do what makes you feel good and that’s the only thing that matters. Maybe you orgasm and maybe you don’t. Whatever your body does, that’s okay. Not everybody finds their first orgasm, if they orgasm at all, through masturbation. Sometimes it is with a partner’s help and that’s okay too. Whatever your body does is okay.
If you are having difficulty specifically relaxing in the middle of masturbation or partnered sex in order to reach orgasm, I would give you slightly different advice. Sometimes cis women feel a very intense feeling like feeling they need to urinate when they are about to orgasm, and it’s often related to g-spot stimulation or an orgasm that is going to produce squirting. Many cis women get very self conscious about this, and so tense up in a way that prevents them from reaching orgasm. Again, you might want reassurance from your partner that whatever your body does is okay.
I really hope that helps, feel free to message me or come off anon and I can respond privately if you need more specific and personal advice.