I'm 21 and I've always had difficulty with orgasm. I had my first orgasm at 15 after years of masturbation and clumsy teenaged experimentation—by myself with a vibrator. Since then, with the exception of random, spontaneous orgasms that occasionally surprise me in my sleep, I couldn't come any other way, no matter how hard a partner and I tried. I stopped hoping for those tingly feelings when I had sex and just whipped out the vibrator when I needed to relieve tension. It became mechanical, and then it became a bit of a nuisance. I didn't like being dependent on something so external, artificial, and completely sexless. My orgasms started becoming less and less satisfying. They felt remote, hollow and incomplete, and left me more frustrated than I was before. I also started to feel like they were becoming detached from my sexuality and the sexual experience.
Now I'm in a very secure, happy, loving, serious relationship with someone I trust, and we have a great sexual connection. Recently when I was fucking her with a strap-on, I was stunned to realize that I was having an orgasm—not only without a vibrator, but without any real stimulation at all. It's happened a couple of times since, and only when I fuck her with a dildo in a harness. I believe this orgasm problem of mine isn't physical, but mental. If I can come with no physical stimulation, something else must be blocking me from letting go. I think one of the helpful factors is that when I am fucking my partner, the focus is entirely on her and her pleasure, and I'm not thinking about myself and wondering where my orgasm is. It's almost a meditative state.
I can probably count on one hand the number of orgasms I've had in the past year. I've decided to forsake my vibrators (all six of them!) until I can train myself to do this myself and not just use a machine to force orgasms out of me like I'm a vending machine. Now I can get a lot closer to orgasm with skin-to-skin contact but there is still something blocking me. I still haven't figured out exactly what it is I need to be asking myself and working through so I can let this go. Can you help me figure out this mental block?
I should probably add that my first sexual relationship was extremely dysfunctional bordering on abusive and still troubles me even though it was six years ago. Also, I'm a bit of a control freak. I hope you can help me!
Do we need to look any deeper to find your block than the simple fear of losing control? For most of us, sex is a paradoxical realm that offers some of the most intense pleasure a human being can experience—along with some of the most severe penalties for daring to take that risk. It sounds like you have experienced being punished in at least one relationship for daring to reach out for intimacy. Add that to the cultural baggage all women get handed, and an individual personality that prefers to be in control, and you've got a recipe for blocked orgasms.
One important key to a solution is found in your letter where you refer to fucking your partner with a strap-on as a meditative state. Stress and anxiety about losing control can be turned aside by taking conscious time to focus within, breathe deeply, relax each muscle in the body, and focus on something other than negative self-talk. "I am safe here," "Nothing bad will happen to me if I lose control sexually," "It is okay to let go," "I want to stay in my body"—these are good alternatives.
I'm not sure if depriving yourself of vibrator use will help you or hurt. You certainly have been telling yourself some dismissive and cruel things about what it means to give yourself pleasure this way. You aren't a bad person because vibrators work for you. Nor does this mean that masturbation has to be mechanical or forced. Whether you are using your hand, a partner's body, or a toy, the idea is to slow down, stay with your physical body, allow excitement to build at its own pace, and validate your right to a sensual experience. If excitement builds but does not result in an orgasm, that's okay—you can choose to take a break, then build it up again.
During strap-on sex, you are thrusting your pelvis and you have some pressure from the base of the dildo or its straps. So you may be getting more physical stimulation than you think. What's missing is performance anxiety. You aren't always second-guessing yourself, asking what will happen, when will it happen, what if it doesn't happen, etc. There's also something very exciting about being inside of your partner, I would guess, that tips you over the edge.
Like many of us, it seems that you have made a hard-and-fast distinction between masturbation and partnered sex. Women who experience difficulty having orgasm with a partner often benefit from blurring that boundary. Combining touching oneself with receiving a partner's caresses can be exciting for her to watch as well as helping you get exactly what you need to come. I've often suggested taking both a lover and a vibrator to bed, if the partner can view this as a fun erotic game instead of competition.
I really hear that your ultimate goal is to be able to come from skin-on-skin touch, not from using a toy, and I think that if you keep on experimenting as you have been, you'll get there. But sometimes it can be discouraging to try and try, and if it doesn't work, eventually one quits. Instead, I recommend using a new technique, whether it's your partner's hand or oral sex or penetration, until you know that you need to come, then switching over to something that you know reliably will work. This means you get rewarded for feeling these new sensations. Sooner than you think, you'll be surprised by the ability to come with the new technique, and you won't need the reinforcement of the older, more reliable method.
You don't mention having any gender issues, but for the sake of other female-born readers who may be in a situation similar to your own, I want to acknowledge that this is another reason why partnered sex can be a problem. If you do have gender issues, having a partner touch or lick your genitals can be alienating. It focuses too much attention on a part of your body that doesn't look the way you wish it looked. But fucking with a strap-on is more gender-congruent, and so it can be possible to achieve orgasm this way. (Of course, those of us who are female-to-male transgendered men usually want more than this, as well, to feel that we have complete sex lives. We need partners who are able to validate our maleness while relating to bodies or sex orgasm that don't look conventionally male.)
Hope it's okay with you that I tacked on that paragraph—as I said, it doesn't apply to you; but I need to try to make each letter as helpful to as many readers as possible. Let me know how it goes! Best of luck with your quest for the Big O.