Survey the District: How to Make Orgasms a Team Effort

Dear Date the District,

I read your post about how to climax/have good sex. While I think your take on this was helpful, I am relatively shy when it comes to speaking up about what I need in the bedroom. While I don't really have body-consciousness issues, I'm pretty self-conscious about the actual process of how things progress in the bedroom. Sadly, I have never achieved the "big O" with a guy before (I know I am capable of it because I've done it myself). For some reason, it just never gets there for me and I can't tell if I am the one with the issues or if it's whatever guy I'm with that doesn't know what he's doing. Either way, I feel totally weird about giving direction or taking direction. Advice on this? Do guys find it off-putting when a girl says "no, do it like this" to them??

No—in fact, it’s a major turn on!

The female body is a huge mystery to most guys. The male reproductive system is a little more straightforward—the target zone is a lot bigger, for one thing.

So a lot of guys have no clue what they’re doing and feel a little lost every time they’re confronted with a vagina. When they’re not 100 percent sure what to do, they start to worry that they’re doing something wrong, which detracts from their ability to enjoy the task at hand.

When you tell them what to do, they don’t have to worry about getting you off. They can follow your instructions and focus on the pleasurable sensations instead of worrying about getting everything right.

Like we’ve said before, guys get off on driving you wild. They can have an orgasm without having sex, and watching you get hot and bothered is a huge ego boost that’s hard to replicate outside of the bedroom.

It doesn’t matter if you had to lead the way—if you can come, they’ll be happy to take all the credit.

If you feel shy about telling a guy exactly what you want, spin it in a positive light. If he’s licking your bellybutton and seems to think he’s found the clitoris, you don’t have to say, “That’s not really working for me.” Instead, you can say, “You know, it feels really good when you do this,” and then take his hand to the right spot. Guide his fingers for the first few seconds, and then let him know when he gets it right. Soft moaning or words of encouragement will do the trick.

Attitude is everything when it comes to sex. Guys love it when girls take the lead, but you can pretty much get away with whatever you want if you act like what you’re doing is perfectly normal.

When guys have sex, they’re more worried about whether or not they’re doing something wrong. They don’t have enough energy left over to watch you with a critical eye, so if you project confidence, they’ll assume that you know what you’re doing.

Sometimes you really have to force yourself to take the plunge to see how this works though. If you’re too shy to ask him to do something outright, move his hand. When you see how willingly he follows your direction, that might give you the confidence you need to deliver verbal instruction.

But sometimes you just have to get over your shyness. It can help to disassociate from yourself. Pretend you’re playing a porn star in a Larry Flint special. In pornos, the women don’t lay there and hope he gets it right. Depending on the genre, they’ll nag, yell, boss, and generally take command.

Or try taking deep breaths and relaxing. The more comfortable you feel, the easier it’ll be for you to release some inhibitions.

But realize that coming isn’t as easy with a guy as it is when you’re by yourself. And the fact that you haven’t come with a guy before is nobody’s fault. There’s nothing wrong with you—it just takes practice!

Be patient and don’t put too much pressure on yourself to have an orgasm when you’re with a guy. You might have some moves you can use to get yourself off, but a guy might not be able to replicate those exactly.

It might take some work and collaboration on both of your parts. But remember, most guys are eager to work with you to achieve climax—no matter how long it takes. It might feel weird for you to make adjustments every few minutes, but the guy is probably so eager to get you off that he won’t notice.

Survey the District: When the Big O Turns Into "Oh No!"

Valentine’s Day is just around the corner, and summer flings that turned into something more are close to hitting the 6-month mark (because let’s be honest, no one’s going out and meeting guys when it’s 30 degrees out).

This can be a confusing time of year for love, so this week will be devoted to readers’ questions. Need advice or looking for answers on sex, dating, or relationships? Shoot us an e-mail at datethedistrict@gmail.com

i don't O in every position, esp missionary and i TOTALLY don't mind.
i.e. i like the intimacy of it and it still feels really good but i
can tell he feels terrible when i don't O and no matter what i say he
still apologizes and thinks it's his fault. even if i Oed earlier in
the night on top, he still feels bad.

For guys, sex and orgasms go hand in hand. Guys usually can’t orgasm without having or simulating intercourse, so they see climax as the goal of every sexual encounter.

It’s different for girls. Girls get off on clitoral stimulation, something that’s hard to achieve from intercourse alone. For most girls, it’s easier to come when you take penetration out of the equation.

That doesn’t mean that intercourse doesn’t feel good, and it doesn’t mean that we don’t like doing it. But it does mean that we approach sex differently.

It’s great that you’re able to achieve climax from sex alone—not every girl can do that. But he might not realize what an accomplishment this is.

So spell it out for him. The next time he starts pouting post-coitus, give him a lesson in female anatomy. Explain that all girls have trouble reaching orgasm from sex alone, and explain that the fact you’re able to come even sometimes is really an accomplishment. Tell him that it still feels good, but explain that, when he gets all huffy when you don’t come, it’s a major turnoff.

When he obsesses over your ability to climax, it probably puts pressure on you and makes it harder to come. So don’t phrase it as a “Don’t feel bad” thing, pitch it as something that’s keeping you from enjoying yourself and therefore making him a bad lover.

Guys want to feel like they’re the best you’ve ever had, and they’ll do anything to feel like a pleasure machine in bed. So say something like, “Look, sex and coming are two different things for girls. If I really want to come that badly, I’ll masturbate. I like sex for different reasons, and it feels really good in a way that’s totally different from orgasming. It’s just the way sex works for girls, and if I didn’t love having sex with you, I wouldn’t be doing it. But when you freak out every time I don’t come, it’s a major turnoff, and if you want it to feel really good for me, you’ll stop talking about.”

And make sure he knows how much you’re enjoying yourself. Make noises, talk dirty, and show him that you’re really into it. An orgasm is just reassurance that he’s great in bed, and there are other ways to show him that he’s amazing between the sheets.

Sex Tips: Eye Contact

Every girl wants to feel like she’s amazing in bed.

Even though we firmly believe that you’re there to please yourself, not your man, we understand that the competitive spirit that dominates our lives makes us want to feel like we’re number 1 at all times.

And because performance anxiety makes some girls so nervous that they can’t enjoy sex, we’re willing to share a few secrets to male pleasure so you can be so confident enough in the boudoir to enjoy yourself at all times.

Today’s tip: unexpected eye contact.

This is less of a go-to move and more of an icing-on-the-cake to pull out (no pun intended) every once in a while.

Guys see eye contact as a sign of enthusiasm, and, like we’ve said before, enthusiasm is the number one thing that turns guys on in bed. When you lock eyes mid-coitus, it makes it seem like you’re so focused on how good it feels that you’re not thinking about anything else.

This is especially effective with blowjobs. Most guys know that blowjobs aren’t a girl’s favorite pastime. But the more enthusiastic you seem, the more they enjoy it. It’s hard to moan when your mouth is focused on other things, but staring into his eyes is an easy way to make him feel like you’re getting off by getting him off.

Locking eyes is also a turn-on in unexpected positions. Try turning around and making eye contact during doggy style or reverse cowgirl. He won’t be expecting it, and that further validation will send him over the edge.

But be careful: this trick is easy to abuse. Too much eye contact gets creepy, especially in plain-vanilla positions where eye contact is kind of inevitable. Don’t stare at him too much if he’s on top (missionary-style) or if you’re on top in cowgirl. That kind of eye contact could make him feel uncomfortable, the way you start to squirm when someone stares directly at you throughout an entire two-hour meeting.

We’re taking off early for New Year’s. See you all next week!

The Girl's Guide to Getting Off: In Bed

Coming is easier for guys.

It’s not fair, but it’s true. It probably has something to do with social constructs: the fact that it’s more socially acceptable for guys to jerk off and to start masturbating at a younger age. It might also have something to do with the fact that a male orgasm is necessary from an evolutionary standpoint. A woman doesn’t have to come to make a baby. A guy does.

It often takes women longer to learn how to have an orgasm. And when they do finally figure out what gets them off, they can’t always climax during coitus.

Some girls expect to orgasm the first time they have sex. And some do, but, for the rest of us, it doesn’t come that easily.

Maybe you’ve never had an orgasm before. Maybe you can only have one when it’s just you and your vibrator. Maybe you only come when a guy goes down on you. And maybe you come from just thinking about sex and have no idea what we’re talking about.

The fact is (and we know you’ve heard this a million times), it’s all normal. Orgasming is much more of a (for lack of a better word) skill that takes some women longer to learn.

And it really is something you have to teach yourself how to do. There’s no magic do-this-and-you-will-orgasm-every-time technique. It takes a lot of experimenting to find a way to reach climax with a partner. And it takes even more work to orgasm from plain vanilla penis-in-vagina sex.

Why do we bring this up? Because the more we talk to women about sex, the more we realize that there are a lot of post-pubescent women who’ve never even had an orgasm. Or they’re not sure if they have. Or they want to have them more regularly, or from sex, or on their own.

This is something that’s not always easy to talk about with friends. And it’s not something that’s easily cured by masturbation, no matter how many virgin sex columnists write their first column about how “outraged” they are that female masturbation is such a taboo subject, and the fact that they masturbate all the time (and are in fact probably masturbating to their own perceived profundity while writing said clichéd column), and how every girl’s sexual problems would all be solved if she simply had the courage to introduce herself to everyone she met by saying, “Hi, I’m Jane, and don’t worry about shaking my hand, because I always wash them after my frequent masturbation sessions.”

If that gets you off, great. But if it doesn’t, and you’re looking for ways to amp up your orgasms, read on. We’re going to talk a lot about orgasms a lot in the upcoming weeks, but today, we’re going to talk about girls who know how to orgasm but have trouble climaxing from intercourse alone.

First, figure out what does get you off. What’s the quickest, easiest way for you to come? Whatever that is, try to incorporate it into intercourse.

Maybe your nipples are the key to peak arousal. Maybe you get off when a guy strokes your inner thighs. Either stimulate those areas yourself during sex, or ask your partner to do it for you.

This is where some girls start to feel shy. They think a guy will be turned off if he finds out that they have foot fetishes or like getting a finger in their back doors.

But here’s what they don’t know: guys love it when their partners get off.

For guys, orgasms are a pretty regular occurrence. Most guys that we know jerk off at least a few times a week, some do it daily. They pretty much have a routine down and can get off fast. And while the sensation might be different in a mouth or a vagina, at the end of the day, an orgasm is an orgasm.

So why are guys obsessed with sex? For them, it’s less about the orgasm, which they can get whenever they want, and more about the other things that come with sex: namely, getting to see a real live naked girl, and feeling sexually desired.

Guys can’t make themselves feel sexually desired with their hands. And that’s why the love it when girls are really into doing them, because it’s the one part of sex you really can’t fake. Every guy wants to feel like he’s amazing in bed, and the louder you are, the more he can believe he’s a sex god.

So if you know something that’ll work for you, don’t be shy. Don’t say, “Um, so, I was wondering if you could, like, finger me while we’re doing it.” Instead, provide clear directions, and say something like, “You know, if you rub my clit while I’m fucking you, it’ll really make me scream.”

Of course, some of these conversations will feel more natural if you wait till you’re in the middle of the act. You’re both hot and bothered, your inhibitions are lowered, and most guys get turned on when women are assertive in bed.

But if you don’t know what works for you, here’s a hint: clitoral stimulation.

For most girls, the clitoris is the shortest path to orgasm. The problem is, standard positions (like missionary, girl on top, reverse cowgirl, etc.) usually don’t do anything for this sexual organ.

If you can find a way to stimulate your clitoris during penetration, you have a better chance of having an orgasm.

Women’s magazines always ntell you that if you rub your clitoris during sex, you’ll come. That works for some people, but it’s not a guarantee.

Here’s a trick one of our friends taught us: if you get on top and lean really far forward (so that you’re almost lying on top of your partner), you can rub your clitoris up against his penis as you’re moving up and down the shaft. It takes some positioning, and you may have to hold the lips of your vagina apart to make sure you’re getting full contact, but once you’re set up, the sensation is similar to what you’d feel if you were grinding up against him in a naked make-out (only more intense).

We’ll share a few more easy-to-orgasm positions later this week. But let us know if this one works for you at datethedistrict@gmail.com.