Survey the District: How to Come Clean After Faking It

Dear Date the District,

I’ve been with my boyfriend for about 6 months now, and I’ve faked orgasms with him every time we’ve had sex. It’s not that he’s bad—I’ve just never had one before, and I’ve always been too embarrassed to tell the guys I’m with. I feel totally comfortable with my current boyfriend, and I’d really like to try coming for real with him. The problem is, how do I tell him I’ve been lying for the past six months?

Female orgasms are a sensitive subject. In the absence of any physical proof, guys are forced to rely on their partners for feedback, and fake orgasms are a huge blow to their egos.

Faking an orgasm is a huge breach of trust, because it’s betraying people in an area in which they usually feel pretty vulnerable: sex. Guys usually assume that women only fake it when it’s really bad, and girls sometimes feel like they have to fake it, even if they’re enjoying it, to make their partner feel adequate.

Coming clean can be embarrassing and difficult, and how you decide to do it depends on where you are in your relationship. If you think he’ll take it well, tell the truth. But if you’re worried it might make him feel incredibly sexually insecure (e.g., he seems to get a huge self-esteem boost from getting you off), there are still a few ways to work on orgasming without telling the whole truth.

If you’ve been faking it during penetration, tell him you’ve never had a clitoral orgasm, and ask him to work with you on that. Tell him he’ll need to be patient, but that it’s really important to you, and something you’ve been wondering about for years.

If you’re faking it when he goes down on you, tell him you want to find your g-spot.

If you’ve started taking medication, you could blame it on that. Tell him your new birth control means you’re going to need to work a little harder to get you back in the saddle, but that your doctor really wants you to try to make this brand work.

Because you’ve never come before, you’re probably best off having him spend more time eating you out. Tell him you want it to last longer than usual, and that you’re going to hold back and make him work harder to get you off.

You could also try something like this, “I always thought I was coming with you, but the other day in the shower, I was touching myself, and it was like this explosion. Like, with you, it always felt really good, but I think maybe this was my first ever orgasm—I was like squirting and everything. I want to get there again—and I want you to do it for me.”

At the end of the day, though, if you love and trust him, you should be able to come clean and work through your sexual exaggeration. He’s obviously doing something right if you’ve been together this long, and make sure he knows how good makes you feel in bed before you tell him your performances might have been a little less than authentic.

Cheating In Your 20s

Fidelity is always murky in the 20-something dating scene.

When you’re not quite sure if you’re together and even less certain that he’s the one, it’s tempting to see what else is out there.

But there’s a fine line between keeping an eye out and cheating—you don’t even necessarily have to kiss someone to betray your partner. We’re not going to spell it out, because sometimes you can have drunken makeouts that do less damage than a heart-to-heart.

The problem with cheating is not less that it hurts your partner, and more that it’s bad for you.

The difference between a cheater and someone who’s just found someone else, especially at our age, is that the cheater often still cares about the boyfriend she dicks over. If she were really just bored and ready to move on, she’d break things off, but she doesn’t, because she’s not.

This creates a situation where the cheater is consistently lying to one of the people in her life that she cares about the most. And this is going to fuck with you more in the long run.

When your closest relationships are mired by lies and deception, they start to be less fulfilling for you. You hate yourself for what you’re doing, the other person has no idea, and it just spirals downwards.

But cheating is often so easy to justify. You blame it on the other person’s busy work schedule, his snoring, whatever. It’s never about you.

But if you stop to think about it, you’re probably cheating to fill a void you feel your relationship. Maybe you feel like he’s not paying attention to you. Or you’re worried he won’t stick around and you feel like you’re hedging your bets.

It’s important to evaluate these concerns. Is he really neglecting you to the point that you always feel shitty? Or are your expectations unrealistic in light of a 60-hour workweek? Do you two seem to be drifting apart? Is the relationship salvageable?

Once you’ve figured it out, it’s time to take action. We’re not saying you should tell him, or even sit down and have a heart-to-heart. But you probably should either break up or stop cheating.

So many people think things will be different when they “find the one” or settle down. But if you only know how to be unfaithful in a relationship, how is the mere presence of one person going to undo a lifetime’s worth of bad habits?

To be clear: cheating is not a moral failure on your part. And though the guilt that comes with it often attaches itself to the person you’ve betrayed, the one who’s hurt most is the cheater.

Monogamous relationships are practice for when you do want to settle down. Even if you think you never will, at the very least, they encourage healthy, mutually beneficial interpersonal relationships. 

Unwelcome Blasts from Your Sexual Past

When it comes to exes, there’s always one type you’re almost guaranteed to hear from in the future: the ones you never really dated in the first place.

These are the guys that blew you off. They’re the ones you hooked up with on Halloween, the ones who took you out for a few dinners, the ones who kept canceling plans or forgetting to call you back, and the ones who, when you look back, you can’t quite remember how or why it ended.

They always try to reenter your life at the most inopportune moments. Maybe you’re seeing someone new, having a bad week, or looking for a new job, and suddenly there’s a text, an email, or, in the rarest of cases, a phone call that hijacks all your focus.

First things first: you’re allowed to feel smug. You’re holding proof that he thought about you at least once, and he’s given you the upper hand.

But that’s probably because he’s 99 percent sure you’re going to throw it away.

You can still gloat, but realize that he’s almost certainly not texting you because he’s realized the error of his ways. If he’s left a voicemail apologizing profusely and begging for another chance, that’s one thing, but if you just got a text that said, “what up”, don’t start picking out your wedding dress.

So what should you do?

Nothing.

The temptation is to bitch him out or brag about your new (and potentially nonexistent) boyfriend, but the second you do that, he’s holding the power and you’re feeling like shit.

We know: you don’t want to be rude. But chances are, he probably didn’t bother much with manners with you. And besides, you don’t owe him anything.

As soon as you say, “Sorry, I have a boyfriend,” you’re giving him the chance not to respond. And then you’ll be checking your phone every 5 minutes, making your friends text you to make sure your texts are working, until finally you can’t take the suspense and text him something really eloquent, like “????”.

But if you don’t respond, he’ll be the one squirming, wondering if you got his message, and why you’re not answering.

So let it go.

It’s tempting to use this whole one-sided-on-his-part exchange to help you move on. And chances are, it’ll make you feel at least a little better.

But realize that the most effective path forward shouldn’t involve him. If you can’t get over a guy until he shows a little more interest, you’re going to waste a lot of time waiting for revenge from guys who are updateable to begin with.

The less you can care about the whole thing, the better.

Monday News Roundup: Where Have The Good Men Gone?

The Wall Street Journal recently ran an article about why a good man is hard to find.

We’ll let that one sink in for a second.

The point is basically that young adults are settling down later and later and that women tend to be more mature than men of the same age.

Profundity aside, the article finds its way to a scary answer to the question it lays out in the title. Today’s young men, the article argues, are lazy, immature, and directionless because their female counterparts are too successful.

It's been an almost universal rule of civilization that girls became women simply by reaching physical maturity, but boys had to pass a test. They needed to demonstrate courage, physical prowess or mastery of the necessary skills. The goal was to prove their competence as protectors and providers. Today, however, with women moving ahead in our advanced economy, husbands and fathers are now optional, and the qualities of character men once needed to play their roles—fortitude, stoicism, courage, fidelity—are obsolete, even a little embarrassing.

This conclusion comes after the author spends half the article arguing that today’s middle-class, college educated men and women spend their 20s adrift, trying to find their lives’ callings. Men, she argues, get stuck because of things like Comedy Central, which appeal to their childish urges and prevent them from moving on.

Sure, there’s no female equivalent of Judd Apatow. But to argue that his movies are creating an ethos rather than reflecting one is a little far-fetched. Her argument, taken to its logical conclusion, seems to suggest that the only reason women aren’t investing in 40-foot bongs is that pop culture has yet to idolize the character of the lazy woman.

Somehow, we doubt that’s all there is to it.

It’s hard to argue that the average 26-year-old man is as serious and career-oriented as a woman of his age. But what does that mean for the women?

The WSJ doesn’t offer an answer. The most obvious would probably be to encourage women to date older men. But guys don’t have a magical settle-down hormone that kicks in when they hit 30. And even if they did, it’s not always easy to know what maturity looks like.

A lot of otherwise smart, career-oriented men love movies like Stepbrothers, despite the fact the “best” scene is no more (or less) than a pair of balls.

And there are some fratty bros who can talk your ear off about Cormac McCarthy in a way that makes it seem like they’ve got more figured out than they actually do.

The fact of the matter is, a guy isn’t going to “settle down” until he finds a woman who behaves in a way that makes him want to lock it down. And if we could teach you how to do that in one blog post, we’d be rich.

But maturity is more than just buying a ring. It’s about remembering to call and engaging in interesting conversation and maintaining friendships that don’t revolve around sex and/or partying. And these are things you can—and should—screen for.

A big indication, as much as we hate to say it, is how he spends his free time.

Guys who live for getting wasted on Friday and Saturday nights might be fun to be around, but they’re probably not as mature as the ones who get up for Sunday morning tennis lessons. And while there’s nothing wrong with the occasional Big Lebowski game, guys with daily drug habits probably have some growing up to do.

Excessive boys nights are a bad sign. Platonic female friends are a good one.

Part of it depends on where you are too. If you have a season pass to the Opera and he measures seasons in kickball, you’re probably on different developmental levels.

But the solution definitely isn’t for women to take a step backwards. It’s for us to keep an eye out for the men who have less growing up to do.

How to Be Sexy Part 2

Yesterday, we talked about ways to sex up your first impression. Today, we’re going to go over one simple tip for leaving a lasting impression on men: physical contact.

No one likes to have his personal space invaded, but a little strategic touching can amp up the sexual chemistry he feels whenever you’re in the room.

The key is subtlety. Don’t grab his crotch after you shake his hand. Start of slowly, and if you sense any discomfort, back off. If he pulls back, angles his body away from you, crosses his arms in front of him, or does anything else that seems designed to minimize physical contact, stop.

Start with his arm. When he says something funny, rest your hand on his forearm while you laugh, but pull it back as soon as you’re done. If you’re standing up and need to maneuver around him, put your hand on his back or shoulder to gently nudge him out of the way. If you’re introducing him to someone else, put your hand on his bicep when you say, “This is Mark.”

The goal is to work your way up to ONE thigh-grab towards the end of the night. But you can’t grab his upper leg, lower your voice, and say something like, “Wanna come back to my place?” You have to briefly rest your hand on his leg while saying something totally innocent and desexualized, like, “It was really great meeting you!” or “Let’s talk more about this next time.” Keep your tone naïve and earnest. Everything but the physical contact should be devoid of all sexual connotations. Don’t lean in close, arch your eyebrows, or pull out your best pouty face. Touch him for a second, and then pull back.

When it comes to touching, less is more, but the more physical contact you can make without his noticing, the more lasting the impression you’ll leave.

How to Be Sexy

It’s easy to stand in a mirror and criticize your looks. For the most part, you can’t change what you’re born with, and you only have to step outside to see women whose bone structures and skin seem proof that they won the ovarian lottery.

But sexual attraction often comes down to the difference between “hot” and “sexy.” A hot girl might have blonde hair, giant boobs, and a perfectly symmetrical face, but if she wears it all with bad posture and unflattering clothes, it’s going to negate a lot of what she has going for her. A sexy woman, on the other hand, might have a plain face, but she knows how to work it.

You can be hot without being sexy, and sexy without being hot. But, given the choice, most guys would pick sexy over Barbie.

Being sexy is, for the most part, intangible. It encompasses things like confidence and sexuality that are too complicated to spell out in a single blog post.

But there are things you can do to up your sexyness factor, no matter what you were born with.

The single most tangible factor that determines sex appeal is probably the body. This doesn’t mean an emaciated, skeletal frame buried in layers of baggy clothing, but it does mean a little bit of muscle definition in your legs and butt.

We’re not saying you all need to rush out and join a gym—it could be as simple as trying to use your legs as a method of transportation (walking and biking instead of taking the Metro) or taking a yoga class once a week. And, actually, the point of getting in shape is not to get down to your birth weight, but to give you more body confidence. Size matters a lot less than how you carry yourself—we’ve posted a million times about how guys can’t tell the difference between a size 2 and a size 6, and don’t care if you seem like you’re into it.

It’s also important to realize that curvy hips and thighs are like catnip to most guys. It’s probably a biological thing (it makes you look more fertile/better at bearing children). If you’ve got it, flaunt it with tight jeans (NOT leggings, which give even the most toned women camel toe) instead of covering it up with baggy sweaters.

Carry yourself well. That means good posture at all times—shoulders back, chin up, chest out. When you walk, let the movement emanate from your hips. Buy a good push-up bra, and wear it. Practice composure—don’t fidget with your fingers, bite your nails, or play with your hair.

When you’re shopping, opt for flattering clothes over trendy styles. Throw away your Uggs and invest in a good pair of heels you can actually walk in. The heel should be thin, not chunky, and if you’re really teetering, go for boots—they’re easier.

Skirts and dresses always make you look more feminine and hide the areas where unwanted fat tends to hang out (like your lower abdomen). A good pair of black tights will elongate your legs and make them look thin (as will the heels).

Start taking care of your skin. This means investing in high-quality cleanser, toner, and moisturizer—probably a step up from what you’d find at a drug store. Get someone you trust to pick out the best makeup for your coloring. Your friend who always looks naturally flawless is probably the best option—chances are, she’s wearing three layers of foundation. If none of your friends has an entire closet devoted to beauty products, go to a makeup counter at a department store. Avoid Sephora—the “cosmetic specialists” there seem to have minimal training and maximal interest in blue eye shadow.

Get up early and start actually getting dressed in the morning. Shave your legs—even if no one’s going to see them. Put on makeup and floss. Again, this is less about how you look and more about how you carry yourself when you know your legs are a smooth as a newborn baby’s.

At the end of the day, looking sexy is a lot of work, and for some people, it might not be worth the investment.

But if you’re with us so far, come back tomorrow (and the day after) for more tips on projecting a sensual, sexual persona. 

How to Give a Great Handjob

First of all, we’d like to apologize to our loyal readers for our recent hiatus. We’ve been doing some traveling, but hopefully we’re back to a more normal schedule now. And to all of our Chinese readers, 新年快乐！

The handjob is the oft-undervalued cousin of the blowjob, which, as we’ve discussed in a previous post, is not complete without a well-lubricated handjob.

Most women don’t give enough handjobs. When the going gets soft, most girls are apt to reach for the problem with their mouths, and when it’s time for the warm up, we give what we want to receive.

But a well-placed handjob can be just as good, if not better, than a blowjob—mainly because both parties are more apt to be really into it. Your hands last a lot longer than your mouth, and you don’t have to worry about gagging.

Handjobs are great for couples that like to spice things up in more public places. Pull him into a bathroom or an alley and give him a taste of what’s going to happen when he gets back to your place. But they’re also great for foreplay, waking him up on a Saturday morning, or getting him to run out and get you Chipotle.

The best handjobs come from the women who give them for a living—happy-ending masseuses. (They have, after all, had the most practice.) We surveyed the men we met on our vacation to figure out what they’re doing right—and what you might be missing.

1. Lubrication. We can’t stress this enough. Use saliva, lube, lotion—whatever you can to grease your palms. The point of handjobs (and blowjobs) is to recreate the sensations of a warm, wet vagina, and dry hands will only hold you back in that department. The more lube, the better.

2. Consistency. A classic handjob mistake is rushing out of the gate. When you start pumping at 50 mph, you’re going to lose momentum after a few minutes. When you’re giving a handjob, you never want to loose speed. It’s a huge letdown for the guy, and if you have to stop, you’re basically restarting from scratch. It’s better to start slow and gradually accelerate. You actually don’t need to speed up until he’s about to come—it’s more important to maintain a consistent speed throughout. So start with something you can sustain, and amp it up at the end.

3. Firm grip. Your grip should be as tight as possible while still allowing you to move up and down the shaft. Squeeze his penis extra hard at the bottom. You’re creating a seal, and it should be as tight as possible. Don’t worry about hurting him—if it’s too much, he’ll tell you.

4. Build up to it. If you go straight into it, it won’t be as rewarding as if you create anticipation. For most guys, the inner thighs are particularly sensitive. Trace the inside of his legs with your tongue or fingers. Gently stroke the balls and taint. Don’t go on for too long, but the more you keep him guessing, the better.

5. Do things he can’t do to himself. Push his balls up between his shaft—take his balls in the heel of your palm with the tips of your fingers facing up. Gently push upwards so that his balls straddle his penis. Stroke his balls with the tips of your fingers. Rotate your grip so that your fingers are on the front of his shaft. Cup your hand and place it over the head of his penis so that when you’re thrusting up, it hits your palm—it recreates the sensation of hitting the tightest, deepest part of your vagina.

6. Aim carefully. Most guys don’t enjoy coming all over themselves, so when he’s about to blow, aim out. Don’t let him come all over his stomach, and minimize the amount of semen on his body. If you’re into it, tell him to come on your face—it’s not as bad as it sounds, it’s pretty easy to clean up, and it’ll be a huge turn-on for him.