The Young Woman’s Guide to Getting Over Herself

This was a posting over at by yours truly. The blog owner there is Alexa, so this was a letter sent to Alexa, and Alexa asked me to answer it for her:

Hi, I’m Steff, and I’ll be your cruise director tonight.

I’m a Canadian girl, born & raised in Vancouver, and I run a site called [Smut & Steff]. One of Alexa’s friends said that being featured on NY Hotties was like being the featured slut in a bukkake-fest because so many people came. So after you shoot your tender lovin’ comments all over this post here, cum over to my site, fill me up and spray me down with even more hot comments. I’m a comment whore!

My specialty is sex advice, which is why I’m hijacking Alexa’s hot little site here per her request. She recently received an email from a young reader that went a little something like this…

Dear Alexa,
Let me start with the usual by saying that I absolutely love reading your blog!

By means of introduction, I am an 18-year-college student in Philadelphia. Freshman year, I had a boyfriend who took my virginity, about 9 months ago. I enjoyed sex with him but for some reason I could never orgasm. We would try oral and manual stimulation which felt great, but still nothing.

I now have a new boyfriend and everything is ten times more amazing, but still nothing. I scream, I moan, but every time I come close, I just want to throw his hand away or push his head away. The pleasure becomes so intense that it’s almost a pain, and then I don’t want it anymore. It’s stressful for my boyfriend because he believes that he’s not pleasing me. What is wrong with me? I try to let myself go and stop thinking about it, but then I worry, thinking that I have to urinate or I’ll get a UTI, if it’s too hard.

If you have any suggestions whatsoever, I’d love to hear them.


Ain’t Came, but Ready to Go

Alexa decided she’d ask me to weigh in on the topic, so I’ve put my little thinking cap on. Being brought up in a pretty repressed household with Catholic morality running rampant means that I have tremendous sympathy for this young woman, ‘cos god knows I had some overcoming to do before coming came ‘round for me.

First off, honey, you ain’t alone. One in five young sexually-active women has never had an orgasm, and I suspect that isn’t even high enough.

You need to realize that it doesn’t make you a freak, there’s nothing wrong with you, and it’s something you can overcome, if you’re willing to get past your inhibitions and try different approaches to resolving your issue. You’re already ahead of the game by admitting this and by wanting more information, because info’s most of what’s going to help you get past this.

First question is, do you masturbate yourself to orgasm?

That split moment before a woman experiences orgasm is often an uncomfortable, almost painful experience, but that’s what makes it all so heavenly when it’s finally broached. You need to let yourself go.

Unfortunately, that’s easier said than done — especially if you never masturbate!

Just so you know, when I first began masturbating in my mid-teens — which is exaggerating the truth since I never got comfortable with touching myself till I was around your present age and had already had sex — I was under the delusion, everytime I approached orgasm, that I had to pee. I can’t TELL you how much toilet paper I went through those first days of dry-humping pillows while lusting after George Michael posters on my wall. I kept running down the hall and trying to pee every time I felt myself getting excited, and then I’d get pissed off, thinking “I haven’t drank anything in two hours! What the hell?”

Know what? That’s how it’s supposed to feel. As for getting a UTI, no. Not the case. After you’ve had sex, go pee and clean up, and that’ll do a lot towards preventing a UTI. The threat isn’t as great as you perceive it to be, not even close, or why would chicks want to have sex as much as some of us do?

Now, for privacy reasons, I don’t have your email address as Alexa has kept that to herself, and rightly so. But as a result, I can’t ask you some of the important questions:

As I already asked, do you masturbate to orgasm? Do you really care about and trust him? Are you scared of the experience or do you have any apprehensions? Are you beating yourself up about your supposed inability to come? Have you ever been assaulted? Were you taught that sex was bad, that to enjoy it made you a whore? Were you raised is a religious household? Are you insecure about your body? Have you ever taken the time to read up on sex yourself? Do you like to touch yourself?

These are far-reaching questions and may even strike you as a little too psychologically-bent to apply to the very “simple” process of getting off when you’re getting hot.

Unfortunately, that’s not the case. Our mindsets are incredibly linked to our ability to orgasm. Particularly as females, we’re so bogged down with societal demands on our morality, with our parental teachings and social stigmas, that we have a lot of baggage we have to overcome before we can bloody well come, that’s more true than it has been in awhile, in this frickin’ uptight Religious Right-dominated political landscape we presently find ourselves under. Shame is the order of the day, and it’s on special two-for-one with a hefty side of guilt. You need to get past all that crap, too, and it’s hard.

Education is the best way to go about it, though, and it’s easier than it’s ever been, thanks to the internet. Honestly, the more you read about sexual dysfunction, the more you’ll learn just how common it really is. For example, I just did a very helpful websearch on Google using the following keywords: orgasm difficulties “young women” about resolutions. Read some of the results and that’ll give you a great headstart.

But you asked for help, so I would suggest a few ways to approach this problem of yours.

First, cut yourself slack, baby. Like I said, you’re in quite a number, what, with one out of five women claiming this problem, too, but that number’s probably higher in reality, considering the shame that surrounds admitting things like this. Hell, I can even tell you about women I’ve talked to who’ve never come alive sexually until they’re in their 40s.

Second, you’re on a completely different page from guys in your age category. They’re at their sexual peak right now — meaning they’re horny as hell and easy to please — and you, honey, you’ve got 10-15 years before you even reach that neck of the woods, which is the standard for all women. And you may think he’s a pro, but he’s probably a very clumsy lover and has as much to learn as you, since the female organs are far more complex than the male organ. By the time you hit your peak, around 30ish, with your being open about this already and wanting to learn more, I guarantee you’re gonna be a sexual goddess. Right now, for you, it’s all about discovering yourself, and that brings me to the next point.

Third, stop thinking that sex has to be all about the orgasm. It is, but it’s also not. Especially not at 18. It’s about learning all about a lover’s body and letting them learn about yours. Great sexual relationships start off slow and build as each partner learns more and more about what to do and what not to do. It’s not a race. For now, stop pursuing orgasms in the traditional sense of the word. This brings me to number four, a homework assignment.

Fourth, download the Divinyls’ masturbation classic, “When I Think About You, I Touch Myself,” and lighten up, considering how much of orgasms come from thought — which is FAR MORE TRUE FOR WOMEN than for men, and moreso today than ever, in this confused redrawing of the gender-lines that’s bringing us into a whole new ball of sexual confusion.

In case you’ve never really explored masturbation, let me give you a few tips. Vibrators are great, but for most women will not result in orgasm, and definitely not at your age — unless you’re using it on your clit. But fingers will do just fine, and are better for you at your age, since it’s about overcoming hesitancy. The happy-button is your clit, and you should be giving yourself a little cliteral massage. Trim your nails nice and short, and introduce yourself to your clit. The clit’s where it all happens, since maybe 10% of women can cum through just intercourse alone.

Massage your clit slowly and gently until you start to get thoroughly aroused, and try to bring yourself to orgasm. Don’t be ashamed of touching yourself or masturbating. Don’t balk when it starts to feel intense — that’s normal. It’s all normal. Hell, masturbating is a part of a nice Sunday in for me. Women who are truly comfortable with themselves sexually always get to know their vagina first-hand. At the same time, squeeze your tits, play with your nipples — this doesn’t make you weird, it makes you comfortable with your inner sex goddess — and believe me, she’s in there.

Make love to yourself. Because if you can’t do this, how can anyone else do it for you? Like Oscar Wilde once said, “To love yourself is the beginning of a life-long romance.” At 18, you’ve got a long road of romance ahead of you. Enjoy the ride.

Fifth, talk to your doctor and tell him/her what’s wrong. Maybe visit a free clinic and pose these questions and have an exam to make sure everything’s working fine or you don’t have any unusual developments. If you’re uncomfortable talking about it, write it out like you did for Alexa, seal it in an envelope, and give it to the doctor’s receptionist a day in advance of your appointment, and explain to the receptionist that you’re too shy to ask the enclosed question, and that you want your medical professional to read it well in advance of when they enter the exam room, so your pride can be spared.

The doc’ll appreciate it too, since their time is money and they’ll be happy you cut through the bullshit and brought up the real issue before the appointment. You should request that they gather helpful resources for you, which is doable if you give them leadtime before the appointment. (Important: Include the appointment time within the letter so the doc knows how much time they have to prepare for you. They’re as scattered as anyone, so don’t be intimidated about simplifying things for them.)

Sixth, tell your man it ain’t him. Tell him you’re working on the issues, that you need him to give you time and space. Learn how to deliver a great blow job. I’ve got a very helpful guide on both BJs and cunnilingus on my website. Read my “Good Girl’s Guide to Giving Great Head.” Explore. Bring him pleasure so he knows you’re breaking boundaries for yourself, but it’s all for him. Let him know that you’re learning to love yourself in every sense of the word. And let him know, that when you’re ready to, you will masturbate in front of him so he can see how you’ve learned to make yourself cum, and he can start things slowly by doing what you’re comfortable with. This is SO helpful for young couples. Have him masturbate himself as he watches you, and you should take notes on that, too. It’s a very arousing experience to share and teaches you both how each other likes to be touched.

Again, if words are difficult to say, then writing is the way to go.

Realize this: By coming to the brink so many times with orgasm, and stopping the process, your body’s dying to let go. The first few orgasms may be difficult to endure, but let it happen. You’ll be so happy and pleasantly spent afterwards that you’ll feel like a new woman in so many ways.

Finally, a last word about the society we live in and how screwed up it can make young women like you feel. As females, we’re taught that if we really enjoy sex and know what we’re doing, we’re whores. We’re taught that “good girls” get married and find nice men and never worry about orgasms, and the “sexual girls” only bond with Energizer batteries, not decent men.

And it’s bullshit. Own your sexuality, baby, because a life of pleasure and strength and power awaits you if you can please your man while loving yourself. There’s no shame in it. Men respect it and appreciate it — and you will, too.

This might well be a new start for you. But it might take a while. Most young women aren’t comfortable masturbating until their 20s, so bear that in mind, since it speaks volumes.

Good luck on your journey to sexual awakening. And enjoy the ride. It’s a long, but fun one.

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