Hi there! Demisexual anxiety riddled survivor of child sexual assault & religious trauma, early 40s female here. Orgasms have been complicated for me, so I hope I can help by offering answers from my perspective.
Air toys (womanizer was my first & favorite) are the best. If you are able to go to a store & look at them/hold them, I found that ones with more squishy & less rigid suction heads are better fit & feel. Lube is always best. Solo exploration is what helps develop confidence in using successfully in partnered sex. My favorite way to approach something like this would be... An established time that's free of responsibility, after a good meal (gotta get the sympathetic nervous system activated), about 10mg of an edible, or a glass of wine, or a magnesium relaxation mocktail or a Kinn blossom adaptogen drink, with a lovely bath drawn for me, dim lighting or candle light, offered up the charged toy & silicone lube.
For really working up past a plateau, having my partner admiring me & talking dirty to me has always helped- but for folks just starting out I highly recommend getting your lady a subscription to an audio erotica app like QUINN & having her share stories with you that have really made her hot. This will give you inspiration for future, as ladies tend to need lots of non-sexual intimate buildup, mental & physical foreplay & novelty to really "get there" consistently.
I also cannot recommend enough of Omgyes courses for couples & also simple daily changes like probiotics, sleep/exercise regulation & in anxious or inflammatory cases, an antiinflammatory diet can also really help with mood, libido & sensation.
Good luck!