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Grey Areas: Wholesome Holiday Sex Edition

I’ve been following your tumblr for a long time but I’m embarrassed to post this under my name. What’s the best advice you have for someone who has never actually HAD sex but kind of done everything but? I mean this in terms of I’m with a person now (I’m a girl, he’s a guy) and he’s so much more experienced then I am and it kind of intimidates me. I want to reciprocate as much as possible but I want it to be enjoyable.


I’ll start off by talking about expertise. This dude you are with may have read all of the books on sex and may have had lots of sex in the course of his life, but he doesn’t know more about your body than you do. You are the expert. On what excites you, what pleases you, and what hurts you. Remember this ever single time you have sex. Your job is not to conform your sexual comfort to his sexual desire. You are there for you. For the physical and emotional pleasure that you can achieve together.

The second thing I’d like to talk about is education. You are now part of a global conversation made up of women talking about their bodies and their sexuality. This conversation takes sexual knowledge that in previous generations would have been shared in small, localized communities and makes it available to everyone. You should start to claim your rightful place in this conversation by reading about sex, reading what other people have to say about it. If the thing you’re reading starts throwing the word “duty” around, telling you it’s your “duty as a woman” to do something, stop reading it. Because the idea that it is your duty to do anything but be the expert on you treats sex like a debate about your body. What if you think it hurts and he thinks it doesn’t? Is it your “duty” to be miserable? NO.

Now a word about pain: pain might be a indicator that you are being hurt or the sex needs to stop. You might enjoy pain and welcome it in your sexual experience, you might not. This is for you to decide. But not all pain is the same. A few weeks ago Chloe Angyal wrote an excellent piece for Salon about pelvic pain. These are the sorts of articles that you should be reading, to inform all of these decisions you’ll be making. Even if you don’t experience pelvic pain, you will probably meet people in your life who do. Giving people healthy, safe information about their own bodies is what we do for each other to keep each other safe.

The one thing I regret about the start of my sexual history is the number of times I let other people hurt me and convince me that sex was one person being miserable and another person profiting from that misery. Once I started insisting on being the authority on what I wanted and what I could handle and what I didn’t like, I discovered that sex could be fun. For everyone!

Be the expert on your own body. Join the conversation and read what other women have to say. Go as slow as you want to. And come back with more questions, if you have them. Good luck.

Okay Beatdown, I know you are all doing holiday preparations, but feel free to share any resources or experiences you think might help this lady. As always, comments will be deleted if they are wrong or creepy or don’t pay due allegiance to the monolithic Feminist hivemind. Last week we had a lot of comments from people who hadn’t read the moderation policy, but still felt the need to criticize it. The picture below is an appendix to the written policy, in light of these criticisms.

The hills are alive with shut the fuck up

ILLUSTRATION: A picture of Julie Andrews with her arms outstretched atop a hill in The Sound of Music. Text reads "Look at all the fucks I give."


  1. Jenny North wrote:

    I think the first place to start is figuring out your own body and what gets you off. And what turns you on about your partner’s body? What turns him on? This should be exciting for YOU. I think it’s great that you want him to feel good and reciprocated, but you need to start with your pleasure and your wants first.

    If you live near a feminist sex shop, go there and check out their resources and supplies. Ask questions of the sales staff. If you a bit of cash, I strongly recommend getting yourself a good vibrator and playing around with it on your own, well before having partnered sex. It’s worth every penny. In Canada, we’ve got a couple of good shops called Come As You Are and Good Vibrations, and both have pretty good websites.

    Also, LUBE. I don’t think this can be over-emphasized. Have lube and condoms, waiting in your drawer. And get a nice lube, the kind that doesn’t smell weird or seem potentially toxic.

    I recommend the following sites and books:

    ** – especially the Sex Readiness Checklist and all the links. The site geared toward teens, but I’ve still found it incredibly relevant and supportive as an adult.

    *Cunt* (Inga Muscio) – Because it is awesome. Then make him read it.

    *Taking Charge of Your Fertility* (Toni Weschler) – although it’s more about fertility than sex and I strongly recommend other methods for contraception, I found this to be a pretty empowering book about lady anatomy and cycles, and especially for demystifying vaginal discharge (“normal” vs. maybe you should see your doctor pronto!). I wish I’d read this before I started having sex and worrying about STDs, etc.

    And on that note, go get tested. It doesn’t matter if you’ve never had penetrative sex yet – “everything but” is a good enough reason for a check-up. Make it a sexy romantic thing, go together, get the full pelvic exam and blood tests. First-time sex should be fun and exciting, not fraught with worries about pregnancy or STDs.

    Friday, December 24, 2010 at 2:35 pm | Permalink
  2. Jenny North wrote:

    Umm – I meant “pregnancy and STDs”. Oh boy. I just read the Pat Robertson thing and I think the conservative word association between sex and drugs just took over my mind. Anyway, I forgot to say, it should be fun! I’m happy for you.

    Friday, December 24, 2010 at 2:38 pm | Permalink
  3. Zooey wrote:

    Oh my, HAVE FUN! Have so much fun! Seriously, my own personal number one tip for fun sexytimes is to expect it to be fun. This sounds so… simple, but my experience has been a lot of women do not go in with this attitude (for various reasons), and thus wind up doing things that are not fun for them. Thinking ‘I am here to have fun’ rather than ‘I am here to do x sexual thing’ is a good rule of thumb for making the various sexual things you do low pressure and mutually enjoyable.

    Second, get the practicalities tidied away. This means a. birth control and/or protection against STDs, and a clearly stated mutual agreement about how that is all going to work, and b. an actual conversation where you both get to say a few basic things. Like, for example, ‘I have never had penetrative sex and I am a bit apprehensive’. Or, you know, ‘I am ticklish under my right arm and any attempt to touch me there will End Badly’. Whatever – you both know the things you kind of wish the other person could magically know and take account of without you needing to tell them. Actually TELLING them is an excellent backup plan with a much higher chance of success.

    Once the above is taken care of, let go of the idea of doing any particular act at a particular time. Just continue fooling around, having fun, knowing all the practical stuff is taken care of, and then go for it when it feels right. And if it all goes not exactly to plan, then what the hell. There will be other times. And if you never tick off every sexual act on your mental list of ‘this is what people are supposed to do’, that’s A-OK as long as you are both happy and having fun.

    In most cases, our bodies make it pretty easy to have sexy funtimes. It’s our heads that make it harder, so making the situation into something you personally will feel okay with helps a lot.


    Friday, December 24, 2010 at 2:46 pm | Permalink
  4. Garland wrote:

    @Jenny North I updated your comment, in the spirit of Holiday whatever.

    Friday, December 24, 2010 at 2:57 pm | Permalink
  5. Sooz wrote:

    My husband and I had a Serious Talk fairly early on in our dating relationship about sex and what we enjoyed/expected/were not into. It seems awkward and terrifying at first, but it really helps a lot when in the mood not to have to take a time out to ask about whether this-or-that is OK. Establishing expectations and desires up front before getting all hot and heavy is a pretty good plan, IME.

    Friday, December 24, 2010 at 4:21 pm | Permalink
  6. Carol the Long Winde wrote:

    My personal view is if you have done everything but…you have had sex. Vaginal/Penile intercourse is not the be all and end all of sex – heck you might not even like it that much but that doesn’t end your sexual career. And if you are serious about not getting pregnant – 2 forms of birth control.

    Friday, December 24, 2010 at 4:30 pm | Permalink
  7. Lorelei wrote:

    I like Emily Nagoski’s blog a lot:

    The penetration tag specifically has advice relating to PIV intercourse, including first-time experiences
    it’s all worth a read, though.

    And to echo Garland, you are the expert on your own body. There is no one right way to make everyone feel good during sex, different people like lots of different things (and the same person will like different things across time and situations). So while your partner may know a lot of techniques and be familiar with the preferences of multiple other people, you are the only one who can tell him what will feel good for *you.*

    In fact, his experience is likely to be most useful in the sense that he will be very familiar with what makes *him* feel good, and so you pleasing him will mainly be a matter of how well he communicates what he wants. Meanwhile, the two of you will both be learning what you enjoy. And if he’s a good sex partner, he’ll pay attention to your pleasure and be patient while you figure it out.

    Friday, December 24, 2010 at 4:33 pm | Permalink
  8. Maya wrote:

    Here’s the advice I wish I could go back in time and give myself: practice noticing whether you are happy or not. In any given situation pay attention to whether you actually are happy, instead of telling yourself that you really *should* be happy.

    Friday, December 24, 2010 at 5:56 pm | Permalink
  9. ozymandias wrote:

    A few tips:

    1) Make sure your boyfriend communicates his likes, dislikes and limits. The best way to be good in bed is to have someone who communicates and to listen to them.

    2) Know your own likes and dislikes. If you haven’t already, masturbate and fantasize. Don’t be afraid to tell your boyfriend if you don’t like something.

    3) Relax. It’s not that big a deal.

    4) LUBE. Use lube! It makes everything better. In particular, I’ve had good responses to a small dollop of lube in the condom.

    Friday, December 24, 2010 at 6:12 pm | Permalink
  10. Alithea wrote:

    Great advice everyone! I haven’t read it in a while but I remember getting good advice at when Is tarted having sex.

    I regards to lube; try to avoid lubes that have glycerin, especially if you’re prone to yeast infections. My sex life got waaaaay better when I learned that.

    Friday, December 24, 2010 at 8:33 pm | Permalink
  11. Isabel wrote:

    Seconding the recommendation for scarleteen – should be required reading for all teenagers, in my opinion. Great, informative, and totally nonjudgmental.

    Also, Garland’s advice is pretty spot-on, but I mean geez, when I started having sex I sure wasn’t an expert on my own body – and, before anyone blames the patriarchy, it wasn’t for lack of comfort & trying. I don’t know if that’s the case for you or not, but if it is – like Maya said: pay attention to what it is you like & don’t like. And don’t feel obligated to like any specific thing.

    The key to happy sex is communication – if he doesn’t know it’s your first time, you should probably tell him, and let him know where you’re heads at in terms of how fast or slow you want to go (or not go), if you’re nervous, etc. And if he’s a dick about it, he’s not worth sleeping with, sorry. Meanwhile, if you’re not sure what HE wants, ask him – I’m sure he’ll be more than happy to share 🙂

    Be prepared to have a sense of humor if things don’t go exactly as planned (“OUCH” “SHIT ARE YOU OKAY” “YEAH YEAH YOUR ELBOW IS ON MY HAIR OW”) – that’s okay, sex doesn’t have to be all 100% srs bsns soft-filtered art movie scenes all the time. Maybe the “first time” (because like Carol, I don’t think PIV sex is the only thing that counts – but you can define it how you want, and anyway it is *A* first time) will be super smooth, maybe it’ll be weird, yes maybe like a friend of mine you’ll have to put it off and give it a shot another day because it’ll hurt. Everyone’s sexual experiences are different – as long as yours are safe & consensual, that’s okay.

    & like Zooey said, have fun! breathe easy, educate yourself (SCARLETEEN IS SO GOOD), and remember that sex is a work in progress. do what feels good, stop when it doesn’t, & I hope you have many happy experiences ahead of you.

    Friday, December 24, 2010 at 9:09 pm | Permalink
  12. Anonymous Blogger wrote:

    Thanks so much for all the advice everyone! I really appreciate everyone being so lovely and helpful.

    I recently got a vibrator and I feel like it has made me more comfortable in my sexuality–I started masturbating at a young age but I never really knew what my real “buttoms” were until my teen/adult years. I feel like I am more comfortable with my body these days and hopefully I will be able to convey that in the bedroom.

    Thanks again, everyone.

    Saturday, December 25, 2010 at 1:19 am | Permalink
  13. I love everyone else’s recommendations, and am pleased to see that Scarleteen’s already been recommended, as that was going to me my first comment.

    One major thing – don’t necessarily expect it to be good the first time, or the second. Play around, aim for fun and experimentation, but it might not all work well, and if it doesn’t, then that’s not the end of the world. You get as many practice tries as you like. Penetrative sex was not at all easy for me early on, so my partner and I took it really slowly – like, work it out over a couple of months slowly – and I am so glad I found someone who understands that the first try doesn’t need to be perfect and magical.

    Sunday, December 26, 2010 at 7:26 pm | Permalink
  14. Pamcakes wrote:

    The worst it should be your first time is physically uncomfortable or only *very slightly* painful (anything more, and he is being too quick/rough with you, and needs to slow down – you should communicate this to him in clear terms), and generally awkward. If it is very painful, or you feel very uncomfortable about it, or for a second doubtful it’s what you want, STOP. Don’t wait until he’s done, not even if he’s about to come. STOP. The pair of you can always pick it up at another point, when you *both* want to.


    Sunday, December 26, 2010 at 9:41 pm | Permalink
  15. m wrote:

    I highly recommend the girl-sitting-on-top as a great first time hetero position. You basically slide on down at your own measured pace while he lies still, allowing you to control how deep and far his dick goes the whole time. You can change the feel by leaning forward (kisses!) or sitting straight up, or arching your back. Both of you can reach your clit with fingers. He can hold you hips to move you around at his pace.

    But yeah, controlling the pace of that first slide on in is really nice.

    Monday, December 27, 2010 at 2:23 am | Permalink
  16. bbjboo wrote:

    Re: masturbation vs. sex-together–you may find you have completely different buttons for each activity, and def. that your orgasms feel different when he’s helping than when he’s not. Don’t let this freak you out.

    Monday, December 27, 2010 at 5:14 pm | Permalink
  17. Amanda wrote:

    I kindof just want to send you guys a little heart. Or a big heart! You know what I mean. I know it should be basic and we should all have been taught so, but at the same time, in this world at THIS time- this article is … beautiful. I listened like you were talking to me, making me stronger in my convictions, self-confidence, and even my basic ability to say “I want to stop” without feeling guilty. It felt an awful lot like a hug I really needed.

    Tuesday, December 28, 2010 at 1:40 am | Permalink
  18. E wrote:

    A little belatedly…Some of the best sex advice I’ve ever heard, from my part-time sweetie to his younger brother (echoing weareallfromearth): Don’t expect to be crazy about sex your first time. Expansion from my fab roommate: Sex is like eating raw clams. The first time you hear about it you go, “People do that? For FUN?” and when you try it, it’s slimy, kind of salty, a little awkward and gooey, and you really don’t get it. But then you try it a few more times, and then before you know it, it is THE BEST THING EVER.

    I also definitely agree with Carol the Long Winde–if you’ve done everything but PIV, then you’ve had sex. Some of the most sexually experienced/satisfied/delighted people I know have never had PIV sex, and never intend to.

    Tuesday, December 28, 2010 at 4:05 pm | Permalink
  19. Jinian wrote:

    I’d suggest reading the Virgin Project comics if you can get your hands on them. You might want to be prepared for a lot of them to make you uncomfortable (they lead with incest! whoa!), but they’ll help you get an idea of the different things that people consider virginity and the range of experiences that people consider their firsts.

    Tuesday, December 28, 2010 at 7:15 pm | Permalink
  20. Eva wrote:

    “Some of the most sexually experienced/satisfied/delighted people I know have never had PIV sex, and never intend to.”

    Agreed. Although E, this kinda contradicts what you said above about pvi being “the best thing ever” 😉

    Anonymous Blogger’s probably already done it by this stage, but here’s my two cents: there’s the possibility that you may never really get into it, or understand what all the fuss is about. And that’s totally fine. I *still* prefer the “everything but” sex to pvi sex, which to my mind is pretty damn average!

    It’s very likely that you *will* enjoy it eventually. I’m just saying that in case it remains kinda tepid, then know that that’s perfectly normal too, and there’s loads of other fun kinds of sex that you may find much more enjoyable.

    Tuesday, December 28, 2010 at 8:33 pm | Permalink
  21. Dell wrote:

    While I agree that this feedback is on the right track I know from my own past that the “figure out what you like” advice was very personally exasperating because no matter how well-read I got (and my friends can cite my encyclopedic knowledge of sex toys and lubes, etc.) I still felt like I didn’t KNOW and that in turn made me feel like a defective sexual being and feminist for wishing I had a dude around to help me explore, because I sure as hell wasn’t getting any answers on my own.

    I felt immense empathy with the character of Sofia Lin on Shortbus for this reason; she’s a sex therapist who can’t reach orgasm. I was past the point of feeling her degree of frustration when I saw the film but I still got irritated reading the “figure out what YOU like” advice so obviously I’m not totally over this.

    (I should also mention, though, that I know that this advice comes from the place of most women experiencing sex with a partner who is more forceful with his sexual desires. My experience has been the opposite – all of my significant partners have been substantially less interested in sex than I am – so the idea of figuring out what I like hasn’t had the same empowering effect.)

    I guess it’s important to reframe this for those of us who may have some mental blocks figuring out what gets us off (due to our own internal chemistry, complications brought about by medications like anti-depressants or hormonal birth control, an obscure preference that we just haven’t discovered yet, etc.), have totally different preferences for solo versus partnered sex, or can’t put what we like in very precise terms. I’ve accepted that figuring out what I like is an ongoing journey and therefore putting my preferences in less explicit terms makes this sort of advice work for me. I like an enthusiastic partner who is open to helping me explore (or as Dan Savage would put it, GGG – Good, Giving and Game). I like treating my sexuality as a science experiment and noting the unexpected responses. I like being OK with who I am sexually, even if it’s not nicely defined or free of its complications. That said, I couldn’t for the life of me know a sure-fire way for getting myself aroused sans a dude in the flesh OR be able to give a partner any useful directions about how to get me off. That’s still totally a crapshoot for me, and accepting that about myself has been really difficult.

    To that end I think there’s still an aspect of this question which hasn’t been addressed, which is that worry about performance, especially if one’s partner is significantly less interested (which seems a lot more common among women than our male-gaze driven society would otherwise imply; I have many friends who share my experience of being the more enthusiastic partner). I think it’s legitimate to be worried about being a poor lover and scaring a partner off, especially if what you like is partner-dependent. To that degree the most important feedback I feel like I could give is: sex is complicated, and embracing that and not expecting rapturous perfection at all steps along the journey will lead to much healthier expectations and sexual self-esteem.

    Wednesday, December 29, 2010 at 1:34 am | Permalink
  22. canomia wrote:

    Thank you! Finally someone saying it’s ok to not know exactly what you want.

    Tuesday, January 4, 2011 at 11:18 am | Permalink