How to change how I have orgasms?

Dear Sex Educator,

I’m 40 years old, reasonably orgasmic, but there’s a catch: I can only come if I masturbate in a rather strange way. I must have learned it as a young child, but I can only reach orgasm if I kind of “hump” the end of a bed, sofa, or other kind of soft/kind of firm surface. It usually takes quite a while, too.

I am too embarassed to do this in front of my partner. His body size (large and soft) doesn’t allow me to reach orgasm by “rubbing off” on him, so I go without orgasms during and after sex.

I’ve tried vibrators, but I only get close to orgasm: only by flipping over and finishing off at the end of my bed can I achieve what I seek.

How can I “retrain” my body to reach orgasm via oral sex or vibrator use?

You ask a good question, and one that is not so uncommon. It’s one of the reasons why it would be better if all kids learned about a variety of ways to enjoy self-pleasure so that their systems don’t get stuck on one route to orgasm. I cannot promise that you will be able to shift this, but I can make some suggestions.

The best way to do this would be to start by incorporating a vibrator into your routine – the Hitachi Magic Wand is a very good choice because you can put it on a firm pillow or other surface and “ride” it. I’d suggest you start by arousing yourself using your hands and a bit of lubricant (not too much, just a bit to make it possible for you to feel the sensation a bit more) and get yourself as aroused as you can while lying on your back. When you’re ready to have an orgasm, flip up and start riding the vibrator. It will take a while to get the feel of it, but eventually the vibrator should become a part of how you get to orgasm.

The other advantage of the Magic Wand is that it offers a firm, broad surface with a fairly strong vibration, to replicate the broad and firm sensations you’ve gotten used to. If this works, eventually you can try using it while you are on your back, pressing it as hard against your whole clitoris (if you don’t know this already, the clitoris runs underneath your labia, and is actually quite long. What you’re doing when you ride to orgasm is stimulating the whole length of the clitoris – something it’s hard to do otherwise). Try doing this in different positions to see which work the best for you.

The other thing you can do with the Magic Wand is use it during intercourse, especially when/if you are being penetrated from behind, or if you are sitting on top of him. In fact, slipping the wand between you and him while you are riding him might allow you to have an orgasm during intercourse.

I also want to urge you to feel ok about getting to orgasm this way in front of your partner. I am sure he is very curious about what works for you, and he’d probably like to be a part of it in whatever way is possible. So maybe you can ride the object of your choice while he stimulates your breasts or other parts of your body at the same time. You can also explore using his leg as your object-to-be-ridden, and then you’re facing him and he’s involved in a very intimate way.

Given the intensity of stimulation that works for you, I am not sure about you being able to have orgasms from oral sex. Oral sex generally works best for those women who need mild-to-moderate stimulation of the clitoris in a small spot, rather than diffused and intense pressure/stimulation like you get from riding something firm. I’d suggest you use oral sex as part of your arousal process, and focus on enjoying the sensations without aiming at orgasm as your end goal. If the vibrator works, you can change positions and use it to climax, if you wish.

Start with these suggestions and work with them for a couple of months. Pay good attention to how your arousal works, what feels the best, and what is happening when you are getting to orgasm from riding something firm. You can always write back and we can work from there once you have learned even more about what does, and doesn’t work.

The Sex Educator