This is an answer for a woman who has never had an orgasm. First,your boyfriend and you should be without any expectations at all. Of course,you should have at least some kind of attraction to each other at first, then to develop a real love. Men make a big mistake: they desperately want to cum, instead of just enjoying sex.You don't need any 'device' or any special pose, everything comes naturally. If your partner can make love for hours, with full control (it is not too hard,though many people think otherwise),to be really focused on pleasure, without any taboos, everything will be OK.
Every girl of mine was the same: totally non sensitive breasts (the solution: a man must play very roughly with them, so it will get A LOT of sensitivity in a very short time) and they couldn't have orgasm.
Man must be able to convey two messages: 'it is normal what you say' (whatever girl can say about anything, which means 'I accept you') and he must awake the child in her.
So, it is not so often to hear that 29 girl become multi orgasmic person in a month, that is, in 3 weekends, and the only limit is her heart, she couldn't stand more orgasms, she had all kind of them anal, vaginal,... just name it.
It is like a big furnace, when you have sex for hours. But, there is one thing: you can't have this by jumping from one bed to another. I had only four girls in my bed. Yes, only FOUR! But I can be a professor for many 'great' men, because I had a time to get know my girls and to go deep in their body and hearts. That's why I was able in a month or two to be somebody not special, but THE ONE. I had the time to spend with them.
So,find somebody special for you. With special pheromones, with special energy, compatible with yours and all Kama sutra books and dildo things will be just unnecessary. Your man will be deeply inside your body and heart.
Is there anything more simple than that? Men don't need to be Supermen, just to follow this advice: not to bed just to cum, but because of this wonderful pleasure. I can exhaust ten women, just because of that lack of pressure. And endurance is what women like the best. And a lot of love.