I’m a 24-year old woman who considers herself rather “sexually stunted”; though I’ve had a few partners, masturbating makes me more uncomfortable than turned on and when I actually do have sex I find myself constantly second-guessing how much I’m actually enjoying it, or whether I’m “doing it right” (even with masturbation!). I honestly doubt that I’ve ever had a orgasm. Though it sounds like your mindset was very different, any advice on how to start exploring my sexuality?
My mindset is not as different as you think; the main difference is that I’m almost a quarter-century older than you are. When I was your age (in 1990) there was no internet to tell me what my sexuality “should” be like; of course we had women’s magazines, but I decided that those were dumb while I was still in high school, so I was blissfully unaware of people who would almost certainly have told me that I was doing it wrong. Almost from the beginning of my sexual experience, I thought of sex more as something I did for other people than something I did for myself, a way to have adventures, to manipulate men, and to trade for favors or presents or money; I reckon you could say I was a born whore, however much prohibitionists may deny that’s possible. As a teenager I masturbated about twice a week, and even that seemed like too much to me; in my twenties it decreased to about once a month (and then only during celibate periods), and the last time I did it spontaneously (i.e. not as a show for a client) was just before I became a stripper in the late ‘90s. As I’ve explained before, I rarely feel what most people think of as “lust”, so though I’m quite responsive I just don’t feel the need to masturbate, and even by my late teens I was dreadfully bored with it. As I’m sure you can imagine, I didn’t always orgasm from it, and like you I often wondered if what I felt was “really” an orgasm at all because it was usually nothing like what my sex partners (male or female) seemed to be experiencing. That’s why I learned to fake well at a relatively tender age; for me, the chief enjoyment of sex has always been about pleasing my partner (whether for love or money) than pleasing myself, and had I believed in Robin Morgan’s asinine statement that “rape exists any time sexual intercourse occurs when it has not been initiated by the woman, out of her own genuine affection and desire,” I’d have probably given up on sex at 17.
Fortunately for my relationships, for my bank account and for many men, I think Morgan and those like her are idiots, and kept at it in spite of not really getting much physical pleasure out of it. And soon after my 17th birthday I discovered that my chief erogenous zone was between the ears rather than between the legs, and that the right situation – in my case, being held down or tied up – did a helluva lot more for me than any combination of kissing, licking, rubbing, twiddling or other purely physical techniques (I later discovered that getting paid had a similar, though less pronounced, effect). Nor am I alone; the majority of women are far more aroused by mental and emotional factors than by physical ones, and the right situation has a far greater effect on sex drive, satisfaction and even orgasmicity than any mechanical or biochemical stimulus.
What this is all leading up to is, you probably just haven’t found your “trigger” yet. Ignore those who tell you that there’s something “wrong” with you for being functionally anorgasmic, semi-anorgasmic or quasi-anorgasmic; I’ve been that way for long stretches of time, and it only ever bothered me was when I listened to people telling me what I was supposedly missing. Orgasm isn’t only about “doing it right”, sexual satisfaction isn’t only about orgasm, and nobody has the right to define the parameters of “good sex” for you, or to tell you why you “should” or “shouldn’t” have sex. My advice to you is, first, to stop doing anything that makes you uncomfortable; if masturbation is in that category, don’t do it (trust me, you won’t shrivel up into a prune without it). Next, try to stop analyzing your sexual experiences; as long as they’re pleasant or otherwise rewarding (emotionally, socially, etc) it doesn’t matter “how much” you enjoy them in comparison with other women or some imaginary gold standard. Once you’ve done those things, a lot of the pressure will evaporate from your mind and you can start paying attention to things like, “What turns me on the most?” or “What situations or activities make sex better for me?” Don’t limit this to personal activities; a lot of my early sexual feelings came from watching TV shows like Star Trek which contained situations that most others wouldn’t view as sexual, but which made me feel “funny”. Even today I sometimes have idiosyncratic sexual reactions to things I see or read, so this isn’t something limited to childhood or relative sexual inexperience. Whenever you run into something that makes you feel sexy, or a sexual activity that turns you on more than others, follow up on it; don’t be afraid to ask a boyfriend or girlfriend for help, either. And don’t be in a rush about it; though most people understand that (in general) women need to take their time to warm up during a sexual encounter, few recognize that this is usually true of a woman’s entire sex life. I’m sure you’ve heard the claim that a woman’s sex drive peaks at 35; that isn’t because of any physiological factors, but rather because it just takes the better part of two decades for most women to get really comfortable with their sexuality and to learn what works best for them as sexual individuals. So you shouldn’t consider yourself “stunted”; a lot of women don’t even start thinking about this stuff until their late twenties, so in comparison with them you’re actually ahead of the curve.