I have never had an orgasm. I've used toys, tried many different positions, and been with both males and females who had different levels of experience. Nothing feels really good. Like, imagine what penetration would feel like if there was no pleasure building up to a strong feeling of release. That's what it's like. But I still enjoy doing sex. I just really wish I knew what an orgasm felt like for me. Sometimes it will feel good for a split second, and I get a rush all over my body, but a small one, like a shiver up your spine. I think that maybe I just react to orgasms differently, and that I don't actually enjoy them as much as other people. I'm not really sure. If you could help, that would be great.
When men or women are experiencing difficulty having an orgasm, I always recommend that they see a doctor for a checkup. Chances are there's no physical reason why you can't come, but it's a good idea to just make sure your body is functioning okay. You should also ask questions about any medications you are taking: anti-depressants, blood pressure medication, diabetes and several other families of drugs (as well as the conditions they treat) can make it hard to climax.
If physical factors are not an obstacle, you should focus on self-stimulation rather than expecting a partner, no matter how experienced, to provide you with an orgasm. If you like reading erotic stories or watching X-rated videos, gather your favorite ones together and let them enhance your fantasies. Sex begins in the brain, so you want your imagination to tell your body that it's time to get turned on. If you are not the kind of person who has a lot of sexual fantasies, it's okay to just listen to some relaxing music, dress up in sexy lingerie or other erotic apparel, burn some incense that you like, or do some other thoughtful thing to make the environment special.
Do a relaxation exercise. Perhaps you want to start with your toes, allowing them to shed all their tension, and continue up your body, identifying each muscle and letting it soften and relax. Pay attention to your breath. Breathe in through your nose and out through your mouth. Let your stomach rise and fall with each breath. As you breathe in, take in serenity and tranquility. As you breathe out, release anything upsetting or annoying that is keeping you from being fully present in your own body.
Then begin to stimulate yourself. You may want to use some massage oil. You can touch your own breasts, run your hands down your ribcage and your thighs, massage your own feet, or tickle yourself gently with a feather or the tips of your fingers. Don't focus on genital stimulation until your whole body feels ready. And don't expect to be able to have an orgasm the first time you try this. You're learning how your own body works, and you are also teaching your body to do something brand new. So be patient, not blaming or shaming.
Some women like to come with nothing but clitoral stimulation. Try doing this with and without lubricant, so you can see what each caress feels like. You may want pressure above your clitoris, below it, or on the sides. Some women like direct stimulation on the glans or head of the clit. Tugging on your labia or running your finger down the groove between outer and inner lips can feel very good. Some women like to feel even pressure on the whole genital area, so they press a pillow between their legs.
If you think that penetration would add something to your experience, it's nice to have an insertable object within reach. I find that butt plugs can make excellent vaginal stimulators during masturbation because they stay in place on their own, leaving you the use of both hands. Put a condom on the insertable toy to make it easier to clean it later. Use water-based lubricant. An oily lube like baby lotion or massage oil can cause vaginal infections because it's hard for your body to get rid of it.
Keep caressing your whole body, your vulva, and teasing yourself with new fantasies. Build up to a peak, take things as far as they can go, then allow yourself some time to ease off and cool down. If you weren't able to come, do some journaling about what your fears were. Some women are too self-conscious to be able to come. They imagine that they will look strange when they lose control. Maybe your fantasies are upsetting; they may differ radically from the kind of sex you would really like to have. What would help you to ease your fears? Do you need to masturbate in the dark? At a different time of day? With a different fantasy?
If you've tried several times to masturbate to orgasm with your hand, and it doesn't work, try using a vibrator. You may need to use it over clothing to prevent your genitals from getting numb. Or you can use it then take short breaks, alternating vibrations with hand stimulation. Some women are concerned about using a vibrator for masturbation because they are afraid a partner won't be able to duplicate the intense sensations it provides. My feeling is that once you've learned to have an orgasm with one technique, it's easier to learn to have an orgasm with other kinds of touching. And there's no law that says you can't bring out the vibrator during lovemaking and share it as a helpful sex assistant.
When you are working on having your first orgasm, it's also a good idea to exercise the muscle that controls the vaginal and urethral openings. It's the muscle that you contract if you stop peeing in mid-stream. Deliberately contract that muscle as you wait for the green light to cross the street, stand in the grocery store line, or fantasize about a handsome stranger. The stronger the PC muscle, the stronger your orgasm will be.