I have been masturbating ever since I was 17 1/2. The first time I did it, I didn't cum. About two weeks later, after much trial and error, I finally had my first orgasm. I was home alone one afternoon and was surfing a site on masturbation techniques. I got so horny reading them. The one that led to my orgasm was a technique submitted by a woman who humped a stack of pillows with a small stuffed animal between her pussy lips.
Curious as to whether this would work for me, I got completely naked and stacked my three pillows on top of one another, climbed up on top, and put one of my beanbag animals between my pussy lips. I slowly began to hump my pillows, my clit grinding against the little beanbag animal. I rotated my wide hips back and forth until finally, I could feel a strong, tingling sensation beginning to build up inside of me. I kept going until boom, I came hard. I bucked up and down, moaning loudly (hopefully nobody outside heard me) as I released that good feeling. I leaned forward a few seconds later to feel it better. It must have lasted nearly 10 seconds. Best feeling I had ever felt in my life.
Later on that day, I grabbed my little massager and put it under me and rode the pillows again. Wonderful. After that, I experimented with penetration and began sticking things into my pussy, long candles, hairbrush handles, my fingers, etc. It felt good, but not as good as rubbing my clit.
Over the past few years, I've also tried other techniques, including pumping my pussy with my fingers or a hairbrush handle whilst rubbing my clit hard. I still hump my pillows on occasion, but it takes a while longer to cum that way. However, a good fantasy about riding a hard cock or doing it doggie style helps. Every now and then, I like to stick a finger inside my asshole when I masturbate. I absolutely love the feeling of fullness up my ass. It hurts sometimes when I do it, but I'm working on making it a little more comfortable.
My favorite masturbation technique is lying in bed naked with my legs wide open, using one hand to rub my clit and pussy while the other hand massages my nipples. I cum every time. I have a message for anyone out there who is ashamed to masturbate: don't be. It is healthy and safe. Much healthier and safer than going out there and catching an STD or getting pregnant. It took me a while to overcome the guilt and shame that so many people tack onto masturbating. I don't buy into the whole 'it's a sin' thing anymore, nor do I believe it causes hairy palms and blindness. That's ridiculous. My palms would be so hairy by now if that were true!!