How To Have Sex Like A Gentleman

I’m lucky enough to have many single female friends who are active on the dating scene, many of whom like to share stories about their dating exploits with me. It provides me with a window into a world that — as a man — I have limited experience with, and helps give a much-appreciated perspective on just how men’s behavior gets interpreted. And let me tell you: hearing some of my friends’ horror stories, whether from online dating or the bar scene is an eye-opening experience about men’s behavior when it comes to trying to get laid.

It also provides a great deal of insight into guys’ psyches. As I’ve written before, men have a complicated love/hate relationship with masculine sexuality. We’re defined by our sexual
conquests, but we’re limited in just who we’re supposed to be desiring; someone whose preference deviates from the culturally defined standards of beauty is less of a man. We’re supposed to want to

fuck many, many women but we’re also taught that the women who let us fuck them are to be seen with contempt. Moreover, we’re taught over and over again that women are the gatekeepers to sex because they want sex less, based on gender roles and misunderstandings about female sexuality, and this leads to the combative, antagonistic dating roles that are promoted by Pick-Up Artists and the various Red Pill blogs and forums.
As a result: what we’re supposed to want is in conflict with what we actually want and are into. We’re supposed to want to fuck women we don’t respect — or even like very much — and then shame them for letting us fuck them. We’re supposed to treat women as the obstacle in getting what we want, which is access to their bodies, to pride ourselves in being masterful lovers and desirable seducers, but to pay less concern to women’s desires except in as much as it lets us get our nuts off. Even guys who pride themselves in their ability to get women off treat it as a referendum on their skill rather than a genuine interest in women’s pleasure and enjoyment. And when men see women hooking up with jerks and assholes, it leads to them thinking that getting sex equals being a rude, pushy asshat.

But it doesn’t have to be that way. It’s possible to get the sex you want — whether a casual no-strings-attached hook up, a friends-with-benefits arrangement, or a committed relationship — without being a dick about it.

Or as I like to call it: how to fuck like a gentleman.

Why Fuck Like A Gentleman?

So an obvious question : why “like a gentleman?” After all, “gentleman” is something of a loaded term; it carries connotations alternately of old-fashioned chauvinistic values and men in fedoras and ill-advised facial hair who think the key to dating success is to treat women with a sort of benign sexism (in as much as denigrating someone for their gender can be benign) by treating them as objects instead of people.
Well… for one, “fuck like a gentleman” is funny and gets attention. And I am nothing if not an attention whore. Also, it conjures up mental images of porn involving sexy men in top hats, spats, and monocles — and everything is funnier with monocles. But also because I believe the term “gentleman” should refer to a person who matches its definition: a man of courtesy and honor, someone who treats others with politeness and consideration, and not be co-opted to mean “old-fashioned douchebag with poor taste in hats.”
I believe that being sexual and pursuing a sexual relationship — whether it be a one night stand, a casual hook-up, short-term dating or a long, committed relationship — doesn’t preclude being polite and respectful of others and encouraging a sex-positive outlook… and I find the word “gentleman” encompasses that nicely.
But also I really just want fan art of sexy men and women in top hats and monocles.

1) Own Your Desire

The first step in fucking like a gentleman is to, quite simply, own your sexuality.
This can seem somewhat contradictory; after all, men are encouraged to be sexual, where women are taught to be less overtly interested. But it’s part of the great paradox of male sexuality: we’re supposed to want sex, but at the same time we live in a sex negative culture and being overly interested in sex marks you as being immature, predatory or dumb. Even among male characters who are lionized for their sexual conquests, media portrayals of men who have a strong interest in sex either show them as damaged or otherwise being lesser than the guy who wants strict vanilla monogamy. Joey Tribbiani is an idiot. Barney Stinson is sexist, self-absorbed, and downright evil. Hank Moody is a perpetual fuck-up, a barely functioning alcoholic who can’t keep his dick in his pants for longer than five minutes. Sterling Archer is a great secret agent but an otherwise all-around horrible human being. Crazy Stupid Love‘s Jacob Palmer’s only a womanizer because of an early heartbreak and Don Jon needs to be taught that intimacy comes through monogamy and is cured of his womanizing, porn-watching ways.
Now, is monogamy bad? No. But treating it as the only correct state for intimacy and sex has the effect of demonizing desire, and leaving many men feeling as though they are somehow wrong for wanting sex, or for wanting to have more than one partner.
At the same time, however, guys get the equal and competing message that settling down is for suckers, that tying yourself down to one woman is tantamount to suicide and that real men are rock hard and ready to fuck at all times. Someone who might be a serial monogamist, or who isn’t interested in casual sex or just wants to find the right woman and settle down is often portrayed as an emasculated sad-sack who’s lost track of his manhood.
Dudes can’t win for losing sometimes.
The core of being a gentleman is to reject the idea that your being sexual — in whatever form your sexuality takes shape — is wrong or shameful. You want to embrace it, own it and wear it with pride. Want to have lots of sex partners? Excellent! Prefer to have a monogamous relationship? Awesome! You do your thing and be happy about it. Just recognize that it’s your choice and it doesn’t make you more or less manly, enlightened or otherwise better than anyone else.
You see, when you don’t own your sexuality, when you feel that your desires are shameful or that being one way or the other makes you a superior person (especially if it’s the opposite of your actual interests) you end up in relationships under false pretenses. You pretend to be interested in something you’re not because it’s what you’re “supposed” to want. Except it doesn’t actually make you happy. If anything you feel trapped, lost, confused… and it has the added effect of making your partner miserable too; after all: she wants someone who’s on the same page, relationship-wise.
This, by the way, goes for owning your “type” as well. There’s a lot of pressure on guys to only like the “approved” standards of beauty, and other men will be quick to enforce those standards. If you like amazonian women, petite women, big beautiful women or just about any other “deviation” from the accepted norm… own it. Be proud of it. If you like big women, don’t be the guy who will only date her on the down-low for fear of what his friends may say, be the grown-ass gentleman who is proud to like what he likes and doesn’t give a damn what others think.
Is it easy? No. Society pushes back hard against people who embrace their own desires outside of the standard manliness package. But part of being a gentleman is the willingness to tell society to fuck itself. You have an obligation to your own happiness; meddlers and strangers don’t get a vote.

2) Accept That Women Are Sexual Beings Too

Just as you have to be willing to own your own sexuality, you have to accept women’s sexuality as well.
It’s all too easy to buy into the myth that women “don’t like sex as much as men”. After all, it’s a narrative that we’ve been fed as a society since the 19th century; men are beasts, women are pure, etc. The problem with this attitude (and there are many) is that not only does it deny women agency or ownership over their own desires, but it encourages men to treat women with contempt. After all, if women are “pure” and “innocent” and just “don’t like sex,” then it follows that the women who do want to have sex with you are somehow “defective” or just “wrong.” It creates a double standard where men are taught to desire women, to try to coax them into bed and then to turn right around and punish them for doing so.
Moreover, the idea that women are less sexual than men leads to the commodity mindset of sex and relationships; since women supposedly care less, they’re able to set “the price” for access to their bodies. This attitude automatically puts men and women into a combative relationship; by its very nature, sex becomes a matter of competing interests. Men are supposed to get what they want for as cheap a price as possible while women are supposed to hold out for as much as they can get, whether it’s marriage, financial outlays (i.e. dates, presents etc.) or some other nebulous value. As a result: you are unable to actually connect; sex isn’t something to be enjoyed, it’s something to be bargained for. It puts you in a position of one person being a winner and the other a loser, which is the worst possible way to treat something as important as sex. It’s impossible to have a satisfying relationship with someone when your relationship is predicated one one or the other being cheated somehow (Incidentally, this led me to a realization about the subtext of Catwoman. Because I am nothing if not a nerd. )
It also means that no matter how much you care for her, you’re not supposed to trust her because those darn hypergamous women are always looking for the next opportunity to trade up.
Straight talk time: women like to fuck. Same as guys do. Yes, there are women who are less interested in sex. There are also women who are interested in casual, no-strings hook-ups, some who prefer to have a series of boyfriends and some who prefer to wait until marriage. Just like men. Accepting that women like sex too means giving up the antagonistic paradigm of the commodity model of sex and adopting a collaborative model of sex instead. Sex isn’t something that you have to bargain for, where there’s a winner and a loser, it’s a partnership. You aren’t looking to get someone to “give it up”, you’re offering something fun that you share together.
The quicker you can process this, the more success you’ll have with your future partners.
Speaking of which:

3) Be Non-Judgmental

Tied into #2 is the idea of being non-judgmental. Women, by virtue of biology, already bear disproportionate physical risk when it comes to sex; the added social risk makes sex even less desirable — especially if you’re both looking for a casual fling rather than a relationship. Just as men are lionized for the number of sex partners they have, women are disparaged for it. After all, in a commodity mindset of sex, a woman who’s had many sex partners has, by definition, devalued herself. Moreover, we still live in a society where a woman who is sexual in a way we (by which I mean men) disapprove of is seen as damaged; as always, I like to point to the continual pearl-clutching over Miley Cyrus’ photo shoots and sexualized performances.

A woman who might be open to having sex with someone new — either as a casual hook-up or with an eye towards a committed relationship, or any combination in between — is going to be less interested if she feels that she’s going to be punished or shamed for following her desires. As studies have shown, women are far more likely to be receptive to casual sex if they see it being worth the risk. So not only do you want to make sure that you show that you’re likely to be offering a pleasurable night, you also want to signal that you’re not a risk to her — either physically or socially.
But this isn’t just about putting up a sex-positive facade in order to trick women. Women aren’t stupid; they’re going to notice very quickly when you’re saying one thing in hopes of getting laid and acting an entirely different way when you think they don’t notice. It’s about internalizing the belief that women who are sexual aren’t deviant, shameful or otherwise worth less.
One of the most common issues, for example, is number of sex partners. Women routinely round the number of partners they’ve had down because people — men especially — will judge them for having “too many”, where “too many” is “any number I feel uncomfortable with”. Except: what exactly does a number tell you?
Answer: Not very much. Having slept with, say, 20 men doesn’t tell you anything about how she feels about you or whether you’re “special” or not. Someone who has had many partners isn’t somehow less choosey or incapable of valuing her partners. Just because someone likes sex doesn’t mean that they’re going to take Johnny AnyCock who happens to wander by. By the same token, someone who’s only had three partners isn’t more likely to commit nor is it a sign that she has high standards that you just happen to meet. She may have had fewer opportunities until now. She may have had a complicated relationship with sex and is only now starting to come into her own, sexually. It doesn’t tell you anything about their sexual health; a person who’s had 14 partners who were rigorous about condoms and getting tested is less likely to have an STI than someone who’s only had three partners, but went bareback on occasion and has never even had a conversation about STIs. It doesn’t tell you anything about her values, her past or anything else. A high number of partners doesn’t mean that she’s sexually adventurous, nor does a low number of partners mean that she’s a boring lay.
All that it tells you is the number of people she’s slept with. Period. The rest are conclusions you’re attempting to draw from it, assuming facts not in evidence. Conclusions I might add, which have far less to do with reality and far more to do with your own personal hang-ups.
A gentleman is nonjudgmental he thinks it’s how he’s going to get laid but because he respects women and treats them as individuals. A gentleman doesn’t judge a woman’s value as a person based on her sexuality. If she has interests that he doesn’t share, or expresses her sexuality in ways that don’t work for him, then it’s not an indication of her being a bad person, just a sign that they’re not compatible; no harm, no foul and hopefully they can part as friends.
A person’s past is a person’s past; everyone has one and most of the time it doesn’t have anything to do with you. Similarly, a person’s interests are a person’s interests. Hopefully they align with yours. If not, then you shrug and move on.

4) Flirt The Right Way

Everyone has their flirting styles. Some people are very sexual up front. Some people like to be more playful and are very touchy-feely. I like to be a bit more teasing and to banter with the women I’m attracted to. Regardless of your personal style, when you’re flirting with someone you have to do it right… and that means maintaining a certain level of restraint. Far too many people push too hard, too quickly and end up ruining their chances. Going slow and taking your time is the key.
Take touching, for example. Touch is an important part of flirting and attraction; being willing to break the touch barrier is part of what makes the difference between a possible hook-up and being seen as a platonic friend. We don’t touch friends the same way we touch potential lovers. However, touching can also be disturbing, uncomfortable or even threatening for someone who doesn’t welcome it. This is why showing restraint is important. Someone who is okay with your touching their upper arm with the back of your hand — generally considered a more acceptable and less intimate form of touch between relative strangers — may not be comfortable with your putting your hand on the small of their back. Plus: when you’re more concerned with trying to push the limits, you miss the real opportunities. A woman placing her thigh alongside yours is a far more positive sign than someone just not resisting when you put your hand on their knee.
This is why you wait for reciprocation. Someone who is interested in you touching them will indicate it by touching you back. 
To use a previous example: if you touch someone on the arm with the back of your hand during an emotional high point in your flirting and they touch you back — most likely in the same way, or even with the palm of their hand — they are indicating that they’re ok with you touching them and you can (gradually) find more reasons to make physical contact with playful pushes, linking arms, high-fives, even taking her hand. If they don’t reciprocate, they’re not interested and you dial it back.
The same with flirty teases and jokes — you watch them for signs for interest. If she starts to indicate that she’s not comfortable with the direction things are going — her smile no longer reaches her eyes, she moves back slightly to less intimate personal space, she folds her arms across herself — then you recognize that you’ve pushed too far and dial things back a little. Letting the other person set the pace of the flirting, at least initially, lets them warm up to you and gives you more time to sell yourself as someone they’re going to want to potentially spend naked time with.
Even someone who is not just open to sleeping with you but is actively interested in it can be turned off by someone pushing too hard. It doesn’t show emotional intelligence and it’s a pretty good indicator that you’re not interested in them so much as getting your rocks off… and a gentleman is very interested in his potential partner’s comfort and pleasure. As long as things are moving forward, you don’t lose points for showing restraint and letting things build slowly. And besides: the buildup of sexual tension is the most delicious part of flirting.

5) Indicate Your Interest… Politely

Not only is it okay to want sex, it’s okay to let her know that’s what you’re looking for… provided you do it the right way. It’s difficult for a lot of guys to admit that they want sex; we’re worried about coming off as boorish or being a pig. We have all the societal lessons about how “everyone” knows guys only want one thing… and we worry that if women think we want them, they’ll reject us. Except… that’s exactly what you should want. If you’re not on the same page in terms of what you’re looking for, then all you’re doing by concealing your interest — or lying about it — is wasting each other’s time. Plus, you’re making yourself look worse and confirming that yes, that is the only thing you wanted and leaving her feeling hurt and used… not to mention making it harder to find the women who do want to sleep with you. If you’re looking for hook-up that night, then being up front about this saves you time. Someone who doesn’t want the same things you do and responds negatively to your interest is self-filtering out of your potential pool, doing you both a favor.
The key to indicating interest in a polite and positive manner is to be honest, but gentle. You give them the triangle gaze — looking from eye, to eye, to her mouth. You close the distance from personal space to intimate space, perhaps lowering your voice or whispering softly in her ear. You bring the touching to a more intimate level — brushing the neck with your fingers or putting your hands on her waist as you step in. You give a more overtly sexual — but not aggressive — tone to your flirting, bringing up the topic of the two of you together alone or even a joking role-play about how you two would never work out as friends because of the attraction. It’s slow, deliberate and above all else, delivered with a friendly, if seductive smile.
All the while, you want to be watching carefully for signs of discomfort. If she indicates at all that she’s not cool with you: she stiffens up, looks away sharply or tries to change the subject, you take a step back (literally) to give her space and dial back the intensity… and all the while you never stop smiling because you’re not angry, you’re not disappointed and it’s not a big deal. You simply don’t want the same things. Better to leave on a positive note — she’s an awesome person, you’re just not on the same page — than to fuss, whine, or pout like a child who’s being told it’s time to turn off the Xbox. By being a gentleman about it, you’re letting her know that you respect her and her boundaries and you prioritize her comfort over your desire to get off. And this will work to your benefit; women talk after all, and having a reputation as somebody who respects a woman and can back off without making a production is a good thing. And besides: leaving on a positive note means she’s more likely to think well of you… and she’ll remember your sterling behavior if she does change her mind.