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July 21, 2009 12:32 PM   Subscribe

Help my partner and I finally have happy, safe, enjoyable sex (definitely NSFW)

Anonymous because I'm feeling pretty sexually incompetent and embarrassed over here.

My lover and I are in our early twenties. He is my first partner, he has had three partners before me. We've been sexually active in one way or another for around six months. Before him, I'd never had a sexual partner, so we started slow with lots of kissing and manual sex, then moved on to oral. He was very patient with me and attentive to my needs during this learning period, and we had a great time exploring together. We're both GREAT at oral sex, for example, and we bring each other to orgasm that way during every session. Anyway, around three months into our sexual relationship, we began to explore vaginal sex. This hasn't really worked out too well for us and we're both getting really frustrated.

As I've said before, we have been trying to have vaginal sex for around three months now but we have been "unsuccessful" ("success" here means him getting inside me and thrusting to orgasm) in all of our attempts. My partner’s penis is not huge, it’s really of an average size, but it seems like no matter what we do, we can’t get him inside me. At my insistence, we use copious amounts of lube every time we try to have sex (I insist that we put lube on me AND on him over the condom, he's not too keen on this because his previous partners apparently didn't use lube at all). Lube really hasn’t helped much.

I really think this has a lot to do with the positions we are choosing and our attitudes toward vaginal sex.

Here’s what ALWAYS happens: Foreplay is great for both of us, we’re really into it and it lasts for a pretty significant amount of time (I’d say 15-20 minutes usually). I’m really wet, he’s got an erection – we SHOULD be ready to go. We have to stop for him to find a condom and to apply lube, but this doesn't slow us down all that much. I think the missionary position is probably the best way to go for beginners, so he gets on top of me and everything usually turns into a huge mess at that point. A lot of stuff seems to happen all at once. He’s telling me, "put me in you! put me in you!" and he's holding my legs practically up over my head and sighing and jabbing around and I'm scrambling with my hands to try to get him inside me. It’s like he's too big and it's extremely painful, even with the copious amounts of lube that I insist we use. There’s a lot of movement and I’m twisted in weird shapes and I’m apparently not coordinated enough to even accomplish simple tasks when I’m like that. He then asks me to get on top, but I am equally unable to impale myself on him. We then try to switch to doggy, which I really rather like, but by then we’re both starting to get a little frustrated with one another and he usually backs away from me and I end up crying. This happens every single time we try. We switch positions trying to get him inside me at least three times and it always ends with tears and both of us a little bit miffed at each other, with one of us telling the other, “I think it’s time we just go to sleep.”

This has been going on for three months and yet we still keep trying. I really, really want to have vaginal sex. I know he really wants to as well. I would like to be able to accomplish vaginal sex. We have tried lube. A self examination with a hand mirror and pictures of hymens AND a trip to the gynecologist reveal that my hymen is already broken. I really think this has a lot to do with our attitudes toward each other during vaginal sex and the positions we are choosing, but it could be other things and that's why I'm turning to you guys.

This upcoming weekend, I'm renting a fancy hotel and taking him there. I would like to do everything I can to make happy enjoyable sex happen this weekend. So, here are my questions:

1. First of all, I think we’re really psyching each other out here. There’s a lot of pressure on for both of us to “perform” correctly and “succeed” and it’s really taking away from our ability to enjoy being together. Is there anything that will help us take the pressure off here? Help us both relax because if we don't, I think it might ruin our relationship!

2. My partner is way more experienced than me and seems to be choosing positions that maximize penetration. I think this has a lot to do with his experiences with his previous partners, none of which were virgins. I’m really not ready for very, very deep penetration. What variations of the missionary position are the most comfortable and easiest for beginners? For example, maybe it would be easier and more comfortable for me to wrap my legs around his waist instead of holding them straight up in the air or drawing them up towards my chest? Tell me what worked for you the first few times.

3. Spooning is a position that we haven’t tried yet. Should we scrap missionary and go with this instead?

4. Any advice at all would be appreciated. I'm losing my mind over here.

Throwaway e-mail: soyourdoinitwrong@gmail.com
posted by anonymous to Human Relations (51 answers total) 5 users marked this as a favorite

 
1. Agreed. Just realize that you're really into each other and you're having fun with other sexual stuff. It'll happen. It really will.

2. Yeah. Don't get your legs up that high. Tell him not to do that; it's counter-productive. You may not even want to wrap your legs around his waist. The first few times for me was legs down but open.

3. It's worth a try, sure.

4. Has he penetrated you with fingers yet? That might help a lot more than a penis at this point.
posted by cooker girl at 12:39 PM on July 21, 2009


Honestly, if you're worried about controlling the angle and depth of penetration, you can start off with you-on-top. Having the getting it in problem is not at all uncommon when you're just starting out, so don't worry about that. But if you kneel down over him, grasp him in your hand, and slowly lower yourself onto him, you can get used to the sensations and control how deep it goes and how fast you want to thrust.

You could also try starting out with doggy style, if you like the idea of that position, but I would warn that that allows for much deeper penetration.

You mention your gyno, but have you talked with your gyno about penetration being painful? There are some conditions that can make sex painful for women, so you might want to get examined.

This isn't your fault. Good luck, keep screwing!
posted by Night_owl at 12:42 PM on July 21, 2009 [1 favorite]


1. When you psyche yourself, your ladyparts often contract. Psychologically and emotionally you might want to have fun sex, but when your internal monologue is going "fuckfuckfuck please let this time work," the vag will close for business until you relax.

and he's holding my legs practically up over my head and sighing and jabbing around and I'm scrambling with my hands to try to get him inside me. ... I’m twisted in weird shapes and I’m apparently not coordinated enough to even accomplish simple tasks when I’m like that. He then asks me to get on top, but I am equally unable to impale myself on him.

It sounds like your otherwise patient boyfriend is sacrificing your comfort and peace of mind by A) pressuring you unnecessarily when the moment of entry arises, and B) going way over the top with silly physical embellishments. You do not need your legs to be over your head to get him inside you (though this might later be a fun excursion), and he doesn't need to make you scramble or get all huffy.

The next time y'all have sex, don't make entry the goal. Read this article about lesbian sex that debunks the notion of fucking as the end-all and be-all of sexual intercourse.

2. I do think missionary is a good starting point for you, but it sounds like he's overthinking the position at the expense of your comfort. Again, you just have to make sure his hips to align with yours, wait for the ankles-on-his-shoulders flourishes for later. He might be more experienced, but he doesn't sound like he has a decent grasp of how virgin girl parts work.

Doggy style might very well work, but try it first rather than waiting til you're both miffed. He'll be more in charge of entry because he can see you better than with missionary, where you're both face to face and can't access the lower halves of your bodies as easily.

3. Spooning is great and is certainly less penetration-intensive than girl-on-top, but it requires a bit more coordination than missionary. I'd suggest holding off til you're successfully having vaginal sex.
posted by zoomorphic at 12:47 PM on July 21, 2009 [5 favorites]


Oof, three months? I'm sorry, and I hope you get this figured out.

Anyway, the position you're describing is NOT missionary, and can be really uncomfortable. I don't know why he thinks it's a good idea when you're not experienced. It's kind of inconsiderate of him, especially since it's obviously painful for you. Keep your legs down on the bed, on either side of his hips. Bend them if you want, whatever. Don't be contorted in any way. That should allow you to (physically) relax enough down there.

In terms of psyching yourselves out, this might have something to do with the fact that he seems to be assuming that such a contorted position is normal for your first time (I know, not technically your first any more, but whatever). He should be focusing on what's comfortable for you, and if he's really a good guy, he'll respond to your requests for a less strenuous position-- at least for the first few times, while you get used to it.

Good luck!
posted by oinopaponton at 12:47 PM on July 21, 2009 [1 favorite]


It’s like he's too big and it's extremely painful

This tells me your issue is Vaginismus. Doctors are good at treatment options.
posted by Ironmouth at 12:48 PM on July 21, 2009 [4 favorites]


4. Any advice at all would be appreciated. I'm losing my mind over here.

I'm really glad you gave us this out, because I don't even know where to start. Have you tried penetrating yourself using something other than your partner's penis? Your fingers? A, dildo or vibrator or other toy? Because this is just literally unbelievable unless a) your partner is completely out of his gourd or b) there is some physiological problem here. Vaginismus? Have you spoken to your gynecologist?
posted by Optimus Chyme at 12:50 PM on July 21, 2009 [4 favorites]


1. He's just going to have to continue to be patient. This huffiness and barking of orders needs to chill out. You're both working toward something that should ultimately be pleasurable, right? A little booze might be helpful here. Not a lot, because a.) you don't want to be sloppy drunk for what I'm presuming you want to be a memorable time and b.) if you're feeling pain, that means something is wrong, and alcohol will dull that response. Just a little booze might take off the edge of the nervousness and frustration.

2. You're absolutely on track here. The positions you've tried can very easily lead to pain. There's no need for him to hold your legs up like that; wrap your legs around his waist and he can insert his penis himself. (I don't know; for some reason the idea of a partner shouting at me to insert his penis into me when I'm likely to be in pain and/or nervous just seems like a turnoff.) Drawing your knees up to your chest is likely to cause pain at first, as well. And holy crap don't try to impale yourself on him! You being on top can wait.

4. You are absolutely right about the lube. Use it on you and on him. You might look into a silicone-based lube like Platinum Wet, rather than a water-based lube.

Really, you guys need to breathe and remember that you like each other, after all, and that you're trying to do something fun. If you don't succeed this weekend (and please consider whether staying at a fancy hotel might be a kind of pressure in itself), it's ok and good to take a break, go for a walk or whatever, then try again.
posted by runningwithscissors at 12:50 PM on July 21, 2009 [3 favorites]


kneel down over him, grasp him in your hand, and slowly lower yourself onto him, you can get used to the sensations and control how deep it goes and how fast you want to thrust.

This.
posted by All.star at 12:51 PM on July 21, 2009


A lot of stuff seems to happen all at once. He’s telling me, "put me in you! put me in you!" and he's holding my legs practically up over my head and sighing and jabbing around and I'm scrambling with my hands to try to get him inside me.

Don't do this.

I don't understand why everything happens "all at once". Why can't things happen one bit at a time? One finger ... maybe two fingers...maybe a thumb...etc. You could go to a sex shop and buy a tiny dildo and try it with that. Fuck, you could try that without him just to see how that goes; or use your own fingers. There's no reason for anyone to panic or start "sighing and jabbing around".

This also doesn't make any sense: "I insist that we put lube on me AND on him over the condom, he's not too keen on this because his previous partners apparently didn't use lube at all." Why is he not keen on this? Putting lube on your dick isn't exactly the ninth circle of hell. Frankly, I don't believe for a second that he's had three partners before you; the man is a virgin.
posted by creasy boy at 12:52 PM on July 21, 2009 [24 favorites]


Good lord, please don't put your legs over your head. That's a position that's great for getting me off, but would completely turn me off if someone tried jumping into it without easing in to something less impacting first. Try missionary with your feet on the bed (or floor, or whatever), with your knees bent as if you were at the gynecologist's, feet-in-the-stirrups style.

Instead of yelling "Put me in you!" your partner should be helping with that too. He should be holding his penis at the base and helping to guide it into you. You should maybe hold the top of it and try to slide it into your vaginal opening. You, presumably, have no problems getting either your fingers or his fingers in there, right? If you're able to do that, and you use lots of lube and go slowly, there should be no problems fitting a penis where you can fit a couple of fingers.

You should also practice tilting your pelvis a bit towards him to help guide him in. That might be one of the problems you're having with you on top. But really, the best thing is using his hands and yours to guide him in. The penis doesn't have a vaginal-homing device implanted. Start by putting your fingers in, the pretend like the penis is just an extension of your hand.
posted by booknerd at 12:56 PM on July 21, 2009 [1 favorite]


MHO, he should stimulate you using fingers adding one at a time until the diameter of the fingers matches the diameter of the, ah, member. Three is pretty close I would guess.

Then, don't rush to the old in and out. Position doesn't matter at all, doggy might be easiest for balance. Put the tip of the penis against your entrance, and begin slow, steady, gentle pressure. Might take 5 minutes, might take a half hour, but keep up the gentle pressure long enough and you will get there. After everything is fully in there, stay still a while, until comfortable/excited. After all that, then try the in and out. Do this one or two times and you will be on your way.

Its all about not rushing it, and being sensitive to the needs of the inexperienced person. IMHO this guy isn't quite getting that. If he won't take it slow the first time or two, think about if you really want him in there at all.
posted by Antidisestablishmentarianist at 12:57 PM on July 21, 2009 [3 favorites]


Definitely consider playing by yourself with a dildo for a while -- just to get used to the feeling of having something inside you. I suggest doing it when you're alone so you'll feel absolutely no pressure to go fast or deep. Just take your time with it and once you're used to THAT go back to fooling around with the real thing. OR -- after you've mastered solo dildo use, get the boyfriend in on the action and then, when that's going well, switch over to his cock. Another benefit of playing by yourself will be that you'll have time to figure out what you like -- slow or fast? Deep or shallow? And, knowing that, you can tell your boyfriend how to best please you.
posted by rhartong at 1:01 PM on July 21, 2009


Try to slow things down a little bit when you're ready for penetration. During foreplay, ask him to insert one finger (and then two, if possible) and work on that for a while. When it comes to penetration, It's likely that he's jumping the gun and thinks that the sex he's used to is normal. That is, all women can handle the positions he has you in, virgin or not.

For example, I had a three-year sexual relationship with the man that deflowered me. It was quite difficult at first, but we eventually got used to the idea that slow can often be better in the long run.
Yet when I began a sexual relationship with my second partner, it was difficult and painful for me at the beginning every time we had sex. So, rather than twisting me into a position that is better suited to veterans, we went with pure vanilla at first and moved on to the positions you're describing. Once he penetrates you, you may find it helpful to tell him to "hold on" for a minute while you get used to it, and then tell him to go slowly at first, otherwise things may not work out so well for either of you.

As for lube, you may not need it, if the natural lubrication is doing its job. There's nothing wrong with using it, and he is getting uptight about nothing in that regard, but it may not be necessary. Just take things slow, relax and be open and honest about what you need.

Good luck!
posted by neewom at 1:05 PM on July 21, 2009


I think this has been happening long enough that you really need to be sure there is no physical problem. It's possible that it's all just a result of unfair and intense pressure being put on you, but I think that further medical investigation is probably warranted - if only for your own reassurance.

At the very least, your partner sounds pretty inconsiderate of how you're experiencing this - you might want to consider how much you're prepared to put yourself through for his benefit. Quite frankly, even when there is serious sexual dysfunction involved sex doesn't usually end in tears every single time - this guy doesn't sound like the ideal partner with whom to try working through this.
posted by Lolie at 1:07 PM on July 21, 2009 [2 favorites]


his barking orders might be related to the condom tango - for some guys it's really difficult to stay hard after the condom goes on and with adding lube everywhere, you're giving yourself a slicker surface to start with and removing all friction from him.

as far as your 'none shall pass' vagina - certainly check with your doctor about vaginismus. have you gotten a pap smear before? if so, chances are you'd already know if this is your problem. if you haven't, go get one now. i also can't suggest a toy fervently enough. get one for yourself. lay on the bed, legs spread, knees bent, and feet on the bed. condom and lube up the toy so it's like it will be when you guys try to have sex. then slowly, very slowly start pushing the toy inside of you. this will allow you to get use to the sensations before there's pressure and a penis that's quickly losing blood flow.

as another tip, one that took me a couple years of sex to figure out. my inner lips are on the larger size and the part at the bottom of my vagina that connects them together seems to be higher than most girls. because of this, my lips can completely cover my opening, or (and OMG painful) one or both of my lips can be dragged inside of me with the beginning thrusts of sex. it's kind of an acrobatic act, but i had to figure out how to hold myself open for the first thrust or two to keep that from happening. everything went better after that. this little abnormality also means that the super deep penetration positions (ESPECIALLY ankles up on shoulders) doesn't really work for me, and for it to work even a little bit i have to warmed up into it.
posted by nadawi at 1:10 PM on July 21, 2009 [2 favorites]


I'm really glad you gave us this out, because I don't even know where to start. Have you tried penetrating yourself using something other than your partner's penis? Your fingers? A, dildo or vibrator or other toy? Because this is just literally unbelievable unless a) your partner is completely out of his gourd or b) there is some physiological problem here. Vaginismus? Have you spoken to your gynecologist?

Uh, having been there before, it's not literally unbelievable.

Everyone's right when they say that the positions you guys are trying are no good for beginner sex, and that his getting huffy and bossy and jabbing you (ow) are no good.

I would try having him sit on an armless chair and straddle him. This position is good because neither of you will be overly concerned about stuff like balance. Tell him not to thrust. You need to be in control of the motions here. I would do a lot of external rubbing before you even try to insert him. When you do, have him hold the base of his penis to guide it in. Meanwhile, take one hand and make your fore and middle finger into a v-shape; use these to pull your vulva out of the way. It might take a few movements of your hips (remember, your hips, not his) to get it fully in there. Definitely use lots of high quality lube--don't waste your time on KY jelly or anything like that.

Generally, I'm all for redefining one's notions of sex. But again, having been there before, I understand why you want to try successfully having vaginal. However, I do think that your particular definition of vaginal sex--hinging on him not only "taking the reins" so to speak but also ending on his orgasm are a little off-base. Focus right now on listening to one another's bodies and moving slowly, rather than one partner's movements or orgasm.
posted by PhoBWanKenobi at 1:11 PM on July 21, 2009


A gentle pelvic tilt will be a better position for you.
posted by pseudostrabismus at 1:13 PM on July 21, 2009


We then try to switch to doggy, which I really rather like

So why not start there?

but by then we’re both starting to get a little frustrated with one another and he usually backs away from me and I end up crying. This happens every single time we try.

No matter what happens in the hotel room, you need to stop before you reach this point. Even if you just say, "Let's take a break for a while." Do it while everyone's still happy.

Seconding trying this on your own with a dildo. For your hotel weekend, can you go have a long relaxing bath alone and play with yourself first for a while, it might make a big difference.
posted by hermitosis at 1:13 PM on July 21, 2009


Um, yeah-- that feet-over-the-head thing can be painful even for very experienced people. It's meant to increase the tightness of your vaginal grip, so it's exactly the opposite of what you want to be doing at this juncture.

If you're just starting out, penetrative sex can be kind of painful, even if you don't have vaginismus, and even after your hymen is broken. And once you've gotten used to doing it in one position, adding new positions to your repertoire can be sort of painful too. It's sort of like taking up running-- it feels really good, but it also wears you out and leaves you achey, until you've gotten yourself into sporting trim. Your boyfriend needs to understand this. With the jabbing and the demanding and the sighing, you're boyfriend's really not helping matters at all.

If it's the sort of thing you're both up for, a bit of light bondage might be therapeutic here-- consider tying him up spread-eagle and then taking complete charge of the penetration yourself-- give him a safe word, naturally, but other than that, no sighing, grabbing, or grousing allowed.

Good luck with this.
posted by palmcorder_yajna at 1:15 PM on July 21, 2009 [2 favorites]


Hate to ask but have you ever watched any porn? It's sort of gross and not really what I like sex to be like, but in a nuts and bolts (erm...) way it can kind of make things a little clearer. Just a thought.

Yeah, it's all pretty gross but it is effective sometimes.
posted by sully75 at 1:20 PM on July 21, 2009


I am going to put this a little mechanically, so forgive me.
You:
-On your back, with a pillow under your butt/lowerback
-Legs spread, bent at the knees, feet on the bed
-With one hand, spread your labia apart

Him:
-Thoroughly lubed and hard penis
-On his knees about a foot or 18" away from your slightly elevated butt (depending on his height)
-His non-dominant hand either on your knee or the bed next to your waist
-His dominant hand holding his penis while manually sliding its tip up and down your vulva
-With slight pressure near the bottom of that up and down, insertion should just happen

Key take aways:
Simple position, you each handle the parts you are familiar with, all of the angles are optimal, no one is stretched or contorted

If this does not work, one or more of you has a physical issue or the total absence of high motor control. This does not mean that there won't be pain, no one can promise that, but this should physically work.
posted by milqman at 1:26 PM on July 21, 2009 [7 favorites]


Extra note:
nthing what all the others said about foreplay... that helps immensely with mental and physical readiness.
posted by milqman at 1:31 PM on July 21, 2009


Stop doing the same thing every time! You've already figured out that it doesn't work. I don't know if you've talked to him outside of the bedroom about this, but you need to. And that conversation needs to tactfully communicate to him that hey, just because he's had sex before and you haven't doesn't mean that he knows what is best for your body--obviously he doesn't. I think you might need to tell him to back off and let you control the situation. I don't know why he's suddenly in a race once the condom goes on, and frankly that sounds obnoxious and like a total vagina-clencher. Try continuing to fool around after the condom is on. Rubbing him against your clit, labia, etc. without actually penetrating. Continue fooling around. And then, when you're ready, slide on top of him slowly.

I say all this assuming you've been penetrated with other things. If that's not the case, start by familiarizing yourself with fingers, then a dildo solo, then have him use it on you.
posted by Polychrome at 1:32 PM on July 21, 2009 [1 favorite]


I don't know why he's suddenly in a race once the condom goes on

Some guys have a difficult time maintaining an erection between putting on the condom and penetration. Trying different condoms can help this, or a different form of birth control if STDs aren't an issue.
posted by muddgirl at 1:36 PM on July 21, 2009


A little booze might be helpful here.
'twas my first thought upon the matter (seriously)

-- also you might want to try ditching the conventional lube and try small amounts of body oil (Burts Bees VitaminE!)
posted by mrmarley at 1:43 PM on July 21, 2009


You may want to try less foreplay. Or, at least, less foreplay that doesn't involve even partial penetration.

It's possible that you guys are just getting yourselves too worked up before you try penetration. Foreplay increases sexual excitation without giving much in the way of release. If you're going a long time, making yourselves all anxious to get some good feeling orgasm going on, then of course you're both going to be very frustrated if you can't get in immediately and satisfactorily.

So... Maybe try speeding up the foreplay before penetration so you can slow down the play after penetration. Get the condom on as soon as he's hard, and try having the ramping-up involve his penis near your vagina. Don't worry so much about getting penetration so he can thrust and you both can orgasm. Instead, just practice with gentle penetration, intending only to get some enjoyment out of it. Then, if it's too difficult or you're both getting frustrated, you can switch from penetration to something you guys know will successfully get you both to orgasm. See penetration as a way to explore, not just as a way to achieve orgasm.

Also, I'm nthing you should talk to a doctor. Just to be certain.
posted by Ms. Saint at 1:45 PM on July 21, 2009


(I am at work right now, shouldn't really be reading this here, and so if a lot of this is repeated above, count it as extra votes for the advice, I'm not going to preview thoroughly.)

* 15-20 minutes of foreplay isn't really that long. It's long, and nice, but as for getting you nice and relaxed, perhaps longer would be great.

* Do you ever orgasm first? Have him give you oral sex to the point of orgasm, whatever you like. You will be wet, very wet, and unlike the gentlemen, we ladies tend to be still ready to go after we come.

* Legs over your head? I would suggest a gyn-style feet in stirrups type thing, maybe legs slightly lower than that. Or from behind, first, although he has to be slow and not go too deep until you let him. He can either push into you, or he can hold still and you can sort of back onto him. You spread yourself apart, he guides himself in with your hand, there's no homing device or a way for it to find itself in without one or two of you putting it there!

* "put me in you! put me in you!" I am not sure what tone is intended here, but it comes across really harsh. I do not blame him at all for being a bit frustrated, and neither do I blame you, but he should be killing you with gentleness and kindness. If the tone is supposed to be "woo hoo I am excited! baby, yum, put me in you!" then that's a bit different, but if it's rushing and frustrated, then I know that would make me feel bad.

* Maybe the strategy shouldn't be penetrative sex until he comes, but rather penetrative sex for a few moments that you both feel ok with. Then he can withdraw and you can make each other come in whatever way you please. And then, next time, you can do it for a little longer. And then a little longer.

* Maybe take a month off. Reconnect physically in other ways, with the understanding that you will NOT try to have sex. And then, when the month is up, try again.

* As always, a few glasses of a nice red wine will go a long way in helping here! Not enough to get you super drinked, please, and perhaps less for him than for you, a trip to smushy town won't help.

* Show him this question and all of the answers. It may help you two communicate about this.

Relax. Breathe. Enjoy. It takes time. I know you know this, and I know it's hard anyway, but the goal is to enjoy each other's bodies, not to thrust thrust guycomes. Be very, very nice to each other. Good luck!
posted by teragram at 1:47 PM on July 21, 2009 [1 favorite]


I said I would suggest a gyn-style feet in stirrups type thing. I hope it was wildly obvious that I meant hold your body as if your feet were in stirrups, not actually get yourself some stirrups for the bed!!!
posted by teragram at 1:50 PM on July 21, 2009


> -- also you might want to try ditching the conventional lube and try small amounts of body oil (Burts Bees VitaminE!)

Do not use anything oil-based with condoms.
posted by pseudostrabismus at 1:53 PM on July 21, 2009 [4 favorites]


Hate to ask but have you ever watched any porn? It's sort of gross and not really what I like sex to be like, but in a nuts and bolts (erm...) way it can kind of make things a little clearer. Just a thought.

This sounds like odd advice to me. Anonymous is perfectly clear on what a penis looks like and where it goes. She's even (frustratingly) well-acquainted with sexual acrobatics of the sort that pornstars get up to in front of the camera. What she and her man need to do is the opposite of porn sex — relax, slow down, get those feet out of the air, choose a comfortable, not-so-flashy position, and go gentle and friendly.

Honestly, Anonymous, it sounds like your partner is trying to Take Charge and Blow Your Mind with Explosive Sex, which is cool except that it's not so much working for you. It sounds, too, like you're letting him Take Charge etc. because he's the more experienced one. But really, that's backwards. You're the one who's trying something new, and that means he should be letting you set the pace. If you do it differently than he would, that's okay. If you take longer than he wants to get him inside you, that's okay too.

I'd have a conversation with him about the grabbing of ankles and the shouting of orders. Let him know that that shit is stressing you out and making it impossible to relax. Tell him to lie back and let you take the lead. And then fool around. Try things. Put him in different positions. Tell him what to do and what you want. If he gets too pushy or thrusty or grabby or whatever, remind him that you're running the show tonight. And if you start to get tired or frustrated, go back to what you know — blow jobs and big hugs all around and get a good night's sleep.
posted by nebulawindphone at 1:56 PM on July 21, 2009 [1 favorite]


Good lord. This sounds like a nightmare on so many levels I can't even comprehend this. The "legs over the head put it in put it in!" scenario is horrible. You're also getting some astoundingly crappy advice here. This is not an issue that is going to be fixed with vitamin E oil or with porn, nor is a trip to the gyn the next obvious thing to try.

First and foremost, your partner needs to SLOW THE FUCK DOWN.

The most conducive position for this is him laying on top of you, face to face, and you underneath him with your feet on the bed and your legs gently or fully splayed. We're looking for something like this [NSFW].

Notice that your hands are free, so you can guide him in at the pace that works for you. I wouldn't even initially try for full penetration; given your history, if you could perhaps just get the head in and massage the rest, you'd be on the right road here.

But really, he needs to slow down and frankly, shut up. If he loses his erection, it's FINE. It isn't the last erection on earth; there will be others.
posted by DarlingBri at 2:10 PM on July 21, 2009 [11 favorites]


Please, go get The Guide to Getting It On. Insist that the two of you read it together. This book is informative, descriptive, funny, and fun to read.

Your boyfriend is not experienced.
posted by Houstonian at 2:12 PM on July 21, 2009 [3 favorites]


It's his dick. Tell him to put it in his own damn self, because it sounds like you're doing enough as it is. You don't need to be grabbing and fumbling with it, especially when he should be in a much better position to see where it is going than you are. Your job is direction of dick placement (too far, not far enough, stop, slow down, etc.), not dick placement itself.

And definitely put the legs down. Sounds like this guy didn't learn much from his (real or imaginary) previous partners. Start simple, and for fuck's sake more lube is good, not bad. I don't understand that particular complaint on his part.
posted by caution live frogs at 2:17 PM on July 21, 2009 [2 favorites]


Lots of good comments. I will echo the things I feel are most important:

1) SLOW THE FUCK DOWN. Its not a fucking race and its not a porn where you just shove your cock in and start pounding.

2) HAVE SOME FUCKING PATIENTS AND KINDNESS. Your bf yelling at you 'put it in you' is really not cool, and not how, as a heterosexual man myself, would ever go about having sex with a girl for the first time, or the like the twenty times after that for that matter.

3) YES YOU ARE PSYCHING YOURSELF OUT. My guess is that the size of his dick, the size of your vagina, and the amount of lube your using have very little to do with this.

Good sex - or at least good sex when you're just starting out with someone, is usually (tough not always I suppose) the result of making sure that the woman involved is happy and having a good time. Most men are fucking thrilled just to be in close proximity to a naked woman and would fuck her armpit if she asked.

And no, your bf is not experienced. At all.
posted by Lutoslawski at 2:34 PM on July 21, 2009 [5 favorites]


And no, your bf is not experienced. At all.

This. I ran into similar problems with a guy who had had three partners (and had sex a total of four times) and was TERRIBLE at everything. Not being a virgin does not make you experienced.

You've gotten a lot of great advice about slowing down, putting your legs down, and telling him to be gentle and considerate and not a jackhammer.

Another thing - don't know how the pubic hair looks, but try getting a Brazilian. Will help with entry, location, etc.

But above all, tell him that this is a marathon, not a sprint!!!
posted by anniek at 2:58 PM on July 21, 2009


...but we have been "unsuccessful" ("success" here means him getting inside me and thrusting to orgasm)

You can't go into this thinking that vaginal sex is the only measure of success. Success should be you and your partner having a mutually enjoyable time. Vaginal sex is great, but if you approach is as something that must be done, it's really going to take a lot of the enjoyment out of it
posted by Midnight Rambler at 3:08 PM on July 21, 2009


getting a Brazilian. Will help with entry, location, etc.

She should not have to pull out all her pubic hair just for him to figure out where it goes!
posted by Houstonian at 3:09 PM on July 21, 2009 [24 favorites]


Listen to Lutoslawski.
posted by whimsicalnymph at 3:13 PM on July 21, 2009


I would suggest putting off the hotel visit at this point. In my experience a hotel visit adds pressure rather than relieves it. It's the money and the implication that everything should work out perfectly. Work out your sexual difficulties first, THEN celebrate with a hotel visit.
posted by Sully at 3:42 PM on July 21, 2009 [2 favorites]


Echoing the other comments about your boyfriend doing completely the wrong things. It's way backwards that you're the one feeling badly here, or that you end up crying at all.

I had a similar problem. My husband and I were coincidentally (because it wasn't religiously/morally motivated) each others firsts. My husband is unusually well-endowed, and I've never been the type to masturbate using any sort of penetration. As you can imagine, this combination of factors caused me a LOT of pain the first several times we tried to have penetrative sex.

My husband was very sweet and patient, and would practically jump backwards the second I showed any signs of pain. If he had reacted like your boyfriend does, I wouldn't have had sex with him. Sorry to be harsh, but you need to recognize that your boyfriend is being a real ass and completely selfish; in particular, aside from the sighing and poking around and demanding you put him in you, the whole bit about being unenthusiastic to use lube on you is practically neanderthal behavior. No guy that makes a woman feel weird about needing to use lube is someone you need to be dating, and it breaks my heart that he treats you that way. I know you asked for help primarily with your sexual problem -- and I'm going to get to that -- but give serious thought to dumping this guy. The only real downside to your being a virgin is that I'm concerned you'll rationalize to yourself that his behavior is okay, or even normal.

His behavior is directly contributing to your sexual problem anyway -- if you're nervous or feeling so badly you end up crying, then of course sex is going to hurt a lot more. Please recognize that you're not the weird one just because you're a virgin, and this is NOT an inevitability of first-time vaginal sex -- regardless of the cause, the whole thing would not be the ordeal it's become if you only had a more sensitive partner. Depending on whether you have something like vaginismus, yeah, it might still hurt, but a different guy would handle that a lot more gracefully.

But if you insist on having sex with him even though he doesn't deserve it, here's what my husband and I did: months of fingering practice. And I do mean months. It took about three or so months, iirc, of just doing that instead of having vaginal sex, I think at least four times a week. When we started a single finger was painful for me, but it got gradually better. Lube as needed, of course. We filled in the gaps with oral. We both learned a lot from that, and it forced us to be more creative in developing other ways to please each other instead of "just ram it in the hole." This is not any less pleasurable or legitimate than penetrative sex, at least in my opinion.

Could you do it sooner than three months? Some people might be able to do it in a couple days, and it does depend somewhat on how big he is and just how much pain you're in and whether there's some medical cause for your pain. Is there any reason to rush, though? No, not unless you BOTH want to -- and not just because one has pressured the other and made him/her feel weird and sexually inadequate, either.
posted by Nattie at 4:24 PM on July 21, 2009 [11 favorites]


Oh, I should also add that the rec for "The Guide to Getting It On" is helpful. My husband is the type to read EVERYTHING there is about anything remotely mechanical, and he takes pride in being the best he can be at everything he attempts, and, well, I'm glad for it. Seriously, a virgin that takes the initiative to read that is in good condition, and there's a ton in there a non-virgin wouldn't necessarily know either.
posted by Nattie at 4:29 PM on July 21, 2009


-His dominant hand holding his penis while manually sliding its tip up and down your vulva
-With slight pressure near the bottom of that up and down, insertion should just happen


This.

I suggest that part of your foreplay becomes "masturbate each other with our naughty bits". This is the game where his job is to use his cock to rub and tickle your clit, and your job is to use the outside lips of your pussy to jerk off his cock.

This is about the funnest game you can play in bed, and to be honest you can just play it until you both come and call it a night.

But the bets part of this game is that when it gets really good, you can find yourself suddenly fucking without even realizing it.

The trick is: you are not trying to fuck! Just play the fun game.
posted by Meatbomb at 5:19 PM on July 21, 2009 [11 favorites]


I suspect your boyfriend is really the one who needs the advice, not you. From the little information you provided, he seems to be missing the point of this whole thing. As cliche'd as it sounds, he needs to be more preoccupied with you, where you are, what you like, etc., and completely in the moment.

Also, that he's had sex before doesn't matter. You mention that he's experienced, but he doesn't sound it (not a jab at him at all). I think he may think he's experienced because he's had vaginal intercourse, but experience is really more partner-specific than anything.

It might be useful to have a simple goal. I don't think that goal should at this point be vaginal sex, though. Rather, since penetration seems so elusive, I think the goal might just need to be that you and he manage it such that his penis is inside you. No thrusting, in other words. Maybe shoot a goal for "mere penetration" and resting like that. I think your body needs to gradually open up to him, but it sounds like in the heat of the passion, you're both trying to make it happen too fast.
posted by scunning at 5:36 PM on July 21, 2009 [1 favorite]


If he's in such a rush, is it because he lose his erection quickly? If so, a cockring can help with that. It doesn't have to be anything elaborate, there are flexible rubber ones that are really easy to handle and do the job of keeping things upright when you need to take a little more time.
posted by xingcat at 5:54 PM on July 21, 2009


Lots of great advice here.

Some may disagree with this, but if you feeling nervous about nookie, it never hurts to get a few under your belt, lets the inhibition slide away that little bit extra.

Don't drink too much, of course - a few is just that - but it can help with letting go a bit.

And don't stress it too much either way, it's a journey, not a destination.
posted by smoke at 6:38 PM on July 21, 2009


anonymous posted">> I think the missionary position is probably the best way to go for beginners...

I think this is probably a mistake. Have him lie on his back and tell him just to lie there, enjoy the view and not interfere. You straddle him and take charge. You don't need to rush to get it in there; there is much fun to be had with rubbing and whatnot. When you're ready you will achieve penetration, as long as you're relaxed and enjoying the rest of the experience anyway. There is no need to worry about it being too deep or aggressive, because you're in control. Just do what feels good for you; he'll be enjoying the experience whatever you do.
On preview, this is basically a variation on the same advice as PhoBWan, milqman and meatbomb, but to reiterate: your partner seems to be doing it wrong; you need to take control of the mechanics in a way that keeps you both relaxed.
posted by nowonmai at 10:29 PM on July 21, 2009


This stuff is supposed to be fun. :) You shouldn't be in a uncomfortable position, much less one that's contorted; it should be relaxed, not loud and confusing. Go at your tempo, not his. Try those positions that seem natural to you. The spooning position can definitely be nice.

It may help if you switch around expectations about foreplay vs. sex. You know you can both enjoy yourselves and get off with oral sex, so consider that the main dish, and vaginal penetration as foreplay, not something that Has To Be Done Right.
posted by zompist at 12:35 AM on July 22, 2009


Oh, honey! I'm cringing for you over here!

If part of the rush is because he's worried about losing his erection after he puts the condom on, how about a female condom? You insert it before you even start messing around. It has a big ring on the outside that stays outside your vagina, and the rest of it sits inside you. Since it's inside you before you start having sex, it'll be the same temperature as you, and you can lube it up and it'll feel practically the same as condom-less sex, and you won't need to switch into condom-mode — it'll be there already. He won't need to worry about the erection issue at all.

And, lucky duck that you are, you live in a time when there are plenty of diagrams and instructional websites and even youtube videos on how to use them.

As other people have mentioned, definitely ask your doctor about vulvodynia or other conditions that might be causing you pain, and work your way up from fingering to fucking. You're right about the lube. You're right about the position being crazy. Others here are right about starting with him getting you off -- he is not the only one who changes shape, you know! After you've had an orgasm or three, your vagina is MUCH more accommodating to visitors. As for being on top, maybe lower your goals for a while. Be on top, but don't try for full penetration just yet. Get used to balancing yourself up there. Show off your boobs. Kiss him. Rub your vulva on the head of his penis. He will enjoy this, I promise, so feel free to take your time. Play with the head in a way that is fun for you, experimenting with pressure and getting the mouth of your vagina around just the head. See what angles work for you. Part of the problem with the "get me in you!" is not just the barky tone and the panic, but also the question of how exactly to guide him in you -- where to aim, what angle works best. Play around and get a feel for it.
posted by heatherann at 8:03 PM on July 22, 2009


This sounds rather familiar - the first guy I had sex with and I were about the same ages as you and your partner, and he said he was experienced, but in retrospect...maybe not so much. I wasn't, in intercourse, and wanted him to take the lead because I thought I didn't know what I was doing. We were only trying missionary, but it just wasn't working - awkward positioning, bits not fitting together, and pretty serious discomfort on my part, which of course we both found frustrating.

What ended up working for us was having me on top, either with him lying down or sitting up. Being able to control the speed and angle of penetration made a significant difference for me, and I think taking some of the pressure off my partner's performance was better for him, as well. As for not knowing what I was doing - well, if you're taking it slow, it's really not that hard to figure out. And even once we cleared the initial hurdle, it still took awhile before I felt like penetration was comfortable - as in, it was at least a month before penetrative sex was something we accomplished easily.

Add my votes for 1) woman on top and 2) man being a lot more patient. Going slowly was really critical for me, as was my partner being very understanding. Oh, and using thinner condoms made a significant difference. Kimonocondoms were my favorites, but they're not always the easiest to find in stores (I've seen them in Whole Foods, but not a lot of other retail outlets) - both Trojan and Durex make "extra sensitive" condoms that made penetrative sex much easier and more fun for both of us.
posted by EvaDestruction at 10:13 PM on July 22, 2009


so he gets on top of me and everything usually turns into a huge mess at that point. A lot of stuff seems to happen all at once. He’s telling me, "put me in you! put me in you!" and he's holding my legs practically up over my head and sighing and jabbing around and I'm scrambling with my hands to try to get him inside me.

Whoa, too much going on! If he can finger you and you know your vagina is 'working' then get on top of him and don't let him hold your legs or jab or tell you to put him in you. Just get on top and grab it and guide it inside. Slowly. Holding your legs and jabbing you seems like a jerky thing to do that won't help.
posted by KateHasQuestions at 3:18 PM on July 24, 2009


I have to know -- how'd it go??
posted by runningwithscissors at 10:54 AM on August 5, 2009


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