Better sex – Part 3/4: For Men: How to Really Pleasure a Woman
A notice on gender and orientation
The following guide uses woman to indicate people who were born with (and still have) a vulva, and were raised “as a woman”, and man to indicate people who were born with (and still have) a penis, and were raised “as a man”. The author chose this wording because most people with this background identify as such. However, patriarchal behaviour patterns such as toxic masculinity, and its counterpart, toxic femininity, are deeply unconscious, and especially tenacious with sex and love: Queer and non-binary people often either keep much of the gender role in which they were raised, or switch to the opposite gender role, in the good and bad sense. This text is therefore applicable to people of all sexual and romantic orientations, and all genders, in that woman and man can mean “person who mostly acts in a way which most people expect from a woman / a man of their cultural background”.
Many straight or bisexual women who are in a straight relationship complain about the following:
“When my boyfriend/husband is inside me during sex, it feels as if he is just poking around. His movements do not feel bad or anything – it’s just that I don’t feel very much at all. I rarely / never have an orgasm during penetration. Other techniques, however, such as when I touch myself, or when he goes down on me, work much better.”
A man who is “poking around” is giving most women the impression that he is choosing his movements randomly or is only following his own desire. This inability, however, is most often a consequence of him being inexperienced with sexual intercourse. He has either had just a few times sex yet, or his past sexual experiences and/or former relationship(s) happened with women who were just as inexperienced and could not provide him guidance on how to do better.
As I have observed, the man’s erratic style is not given by nature, instead, he unconsciously follows a seemingly logical path. There are very few men actually who do not care at all whether they are giving the woman sexual pleasure. The reason is instead rooted in the fact, that most men are raised in the social role “man”, a set of behavioural rules that produce toxic masculinity in real life. One of these false beliefs of the social role “man” states:
“More is always better.”
Among other things, this belief is the origin of the obsession and the inferiority complex that many men feel about their penis’ size (“Bigger is always better”). Women are often baffled by the extent of such concerns, either because they have been raised in the social role “woman” which doesn’t contain such a belief, or because, as owner of a vagina, they know from their own experience that too big a penis can complicate intercourse or even cause them pain. As a consequence, the latter will see the man with the biggest penis as an interesting erotic experiment maybe, but will choose a man with a practical penis size for a long-term sexual involvement or a romantic relationship. Only a minority of women will actually prefer a very large size.
During all straight sexual activities, especially penis-in-vagina intercourse – but also cunnilingus, penetration with fingers or a dildo, and anal intercourse – the same belief causes another difficulty: The man thinks that the harder, faster or deeper he goes, the more the woman will enjoy the sex. This is the origin of two behaviours that so many women complain about, so that, among female friends, they have become a cliché when they tell the story of their last sexual encounter:
- At the beginning of penetration, the man goes as deep as he can, followed by fast thrusts, thinking that the woman will find the most pleasure in sex like a rocket launch.
- If the woman is showing signs of sexual enjoyment, he increases his speed (further) or thrusts her even more deeply. He thinks that if his movements are so good that she is undoubtedly enjoying them, then moving faster and deeper will give her even more pleasure.
Both techniques are, however, a misunderstanding: Most female bodies simply do not work in this way.
For a woman to experience pleasure out of movements inside her vagina, two conditions must be met:
- She must have a vaginal erection.
- She must be lubricated: Both the inside of her vagina and its entrance should offer a good glide.
1. Vaginal erection
Women, just like men, get an erection when they are aroused. A vagina that is erect adapts to the length, diameter and shape of an inserted penis, finger or object which is the basic requirement for pleasurable penetration. How long a vagina takes to adapt to a given size, however, differs by the individual – it can take a few seconds to some minutes. Both time spans are healthy and depend on how relaxed the woman feels, and how well the outside and inside of her vagina have been “turned on”, which is commonly known as foreplay. If she has had too little time to adjust herself to the “filling”, or has not enjoyed the kind of touch (or the lack thereof) that she has received, the penetration chafes in yet unprepared areas, which the woman experiences as an uncomfortable feeling.
If she is relaxed enough depends highly on whether the man ensures her wishes are met just as he pursues his own, in short, whether he values fairness. Unfortunately, there are always men who deem giving foreplay unnecessary. Therefore, they only offer it at the firm request of the woman, and even then they do it, visibly annoyed, in a “I’ll be glad when it’s over”-fashion. Ironically, a man of this type always gives himself sufficient foreplay, either with sexual fantasies, by watching porn, or by masturbation. When he feels ready for penetration, he addresses the woman, who is surprised by his desire, as she hasn’t done anything to get into the mood, and thus doesn’t have an erection of her own. Another version is that both start at the same time, with the man enjoying when the woman gives him head or offers a helping hand. As soon as he has a sufficient erection, he wants to start penetration – while he didn’t provide pleasant stimulation or simply didn’t allow the time for the woman to get a sufficient erection as well.
Although every woman gets wet when she is sexually aroused, the amount of fluid differs by the individual. Some get so wet the juice is running down their thighs, while others produce only a few drops that become visible only after penetration has taken place. Both amounts are healthy and do not state anything about the kind of sex she wants to have right now: A very wet woman does not necessarily desire hard fucking, and an apparently dry woman can be nevertheless especially horny. Best way to find out: Ask her. If she is among the women who become little wet by their own fluid or if she has just a less wet day (maybe because she isn’t hydrated or due to stress) – use lubricant, spit, or any gliding product that is healthy for human membranes to provide the necessary glide (water alone doesn’t work because it doesn’t stick). This gliding effect must be given everywhere inside the vagina and at its entrance, otherwise the penetrating object adheres to the too dry area which generates an uncomfortable feeling.
Therefore, the first few movements inside the vagina have the purpose to allow her vagina to adapt to whatever is inside and to distribute fluid evenly over the parts of her vulva which are involved in penetration.
If, however, the man begins to insert his penis with great depth or speed, for most women, the penetration does not produce the intended effect of giving her pleasant feelings, but gives her a neutral, boring feeling or even unpleasant chafing instead. This is not quite the ideal beginning of an enjoyable sexual experience. For a sensitive woman or one who has just overcome a genital infection shortly before (like a urinary tract infection), this technique can even feel mainly painful and will most likely terminate her interest in further sexual interaction immediately.
More is not necessarily better
For a woman (or any receiving sex partner) to feel any sexual pleasure, she must allow herself to let go and follow the touch or movement of the giving partner. If she is showing signs of pleasure, she has found a good rhythm to follow – meaning, that she enjoys the man’s touches or movements, just how they are right now. If the man changes his touch or movement at this point, he is also changing the pattern the woman has adapted to, which causes her feelings of pleasure to drop or disappear suddenly. The woman will need some time to adjust herself to the changed pattern. But, as soon as she has relaxed sufficiently to enjoy the new pattern and shows signs of pleasure again, the man changes his technique again, or tries to speed up his movements, causing her pleasure to drop once more, etc.
While it would be simple to observe this linear dynamic, the situation is more complicated. No man is able to speed up his movements consistently like a fucking-machine. A man who is constantly trying to fuck harder, will therefore slow down suddenly and then speed up again, either because the fast thrusts exhaust him or excite him too much and put him close to his orgasm too soon.
This leads to total confusion of the woman. Every time when she is in a good rhythm and feels pleasure, the feeling drops suddenly. Furthermore, the man is not only abruptly moving faster, but is also abruptly slowing down, in a seemingly random order, and as a consequence, she does not know what to expect next and how to adjust herself. As a result, this requires the woman to concentrate excessively to feel constant pleasure during sexual intercourse, or she gives up and does not react to the man’s movements (any more), just waiting for him to come since the concentration exercise is (or has become) too exhausting compared to its pleasure gain.
All of this originated in the fact that the man was raised in the social role “man” and is therefore mostly unconscious and not chosen behaviour. Unfortunately, many men actively perpetuate their beliefs from there, in that they blame the woman for “not doing it right” or “not working as she should”, and silence, slutshame, or flat out ignore her whenever she communicates her “abnormal” desires and wishes before or during sex.
As a man, you can stop this dynamic by doing the following:
Start soft. Go slow. Allow for pauses. The logic behind this is that if you start slow, most women will like what you are doing, and you can still increase pressure, speed, depth, etc. later. If you, however, go in full speed, you will most likely irritate or hurt your woman. Moreover, if she wants you to fuck her hard, she only has to tell you once, which will most likely be a pleasant moment for both of you, whereas having to remind you several times to slow down will annoy the both of you.
Now to the details:
Before you go between her legs, make sure you have washed or disinfected your hands. Women can contract (and spread) many infections simply from getting germs from unwashed hands onto or inside their vagina. These infections make sex painful and life unpleasant, and usually require a week or longer to treat, in which time no penetration should occur. Pro tip: If your woman doesn’t like cold hands, here is how to avoid them: If you have access to warm water, let it rinse over your wrists for a few seconds. If not, put your hands between your thighs for a minute afterwards.
Many women claim that they would need a long foreplay. However, for most women, this is not true. Instead, this claim is based on an unconscious countermeasure: Many men give foreplay in the form of too rough touches, or constantly change the technique before the woman can even adjust to it. A long foreplay, however, has the effect that he will slow down after his first “rush”, and the longer period of time increases the chance that he will repeat the techniques that the woman likes, or apply them longer, so that she is able to actually enjoy them.
Experienced men (and women!) therefore know that it is not about the duration of the foreplay, but rather about its efficiency:
Don’t “rush” immediately onto her genitals. Begin sex with touching other spots of her body. Choose movements and pressure as a rule of thumb half as firm as you originally wanted. Most women enjoy when you start further up (e. g. shoulders) or down (e. g. feet), and then move towards her vulva. Forget about your own body for the moment and instead focus on hers. Stay at least 30 seconds with the same technique (gentle touches, a massage, etc.), at the same speed. If you are not so good with time, count in your head from 20 to 50 – that’s about 30 seconds. Make one deliberate, dedicated touch after the other. Encourage her to touch herself in addition to your touches, thereby splitting the foreplay between the both of you.
Between two and five minutes of efficient foreplay can make the difference between good sex that she wants to do again, and yet another boring encounter. Then you can move on to penetration (regardless if you finger her, use a dildo, or fuck her).
No matter how urgently you desire to fuck her hard – if you want her to like it, her vagina needs to adapt to the shape and size of your penis first. Three techniques do the trick:
- Use your fingers to touch the entrance of her vagina, and then move slowly (!) inside, and feel how her vagina is widening, and how she gets wet. As soon as you can comfortably fit as many fingers as your penis is wide inside her, she is able to receive you with pleasure.
- Use your penis, and go fully inside, but then remain still or just do minimal movements to support your own erection, until her whole body visibly relaxes (or she starts to move, or tells you to get going).
- Use your penis, but go half as deep and half as fast as you would like it right now. If you wish to increase depth and/or speed, as a rule of thumb, do it after the fifth thrust at the earliest.
Exception to all these tricks: She tells you directly to skip foreplay, that she enjoys a completely different foreplay better, or that she wants you to fuck her harder.
If the woman starts showing signs of pleasure after this initial phase, meaning that she is suddenly taking deep breaths, moaning, or making affirmative sounds such as “Yes!”, “Ooh”, etc. continue your movements exactly as they are. It is by the way not relevant whether you are fucking her fast or slowly – the important part is to keep the rhythm the same! Therefore select a sufficiently comfortable position where you can apply depth and speed in such a way that you can carry on longer than a few seconds, without having to change your pattern. If you have trouble keeping a rhythm, play some music with the right tempo in the background, and just carry on. You will thrust to the music, even if you do not focus on it.
Change pressure, depth, speed, angle, or technique only if one of the following happens:
- She tells you directly that she likes it better faster or slower, deeper or less deeper.
- You want to try a specific move.
- You find that you do not gain sufficient pleasure from your own movements.
- You happen to lie/sit/stand uncomfortably and would like to change into a more comfortable position.
If you cannot tell whether she is (still) enjoying the sex, but very quietly, has dozed off, is writing the grocery list in her mind, or is watching the television running nearby, ask her to tell or show you what feels good for her – during foreplay and penetration. If she does not like to show loud signs of pleasure, such as moaning, she can simply say “Yes” as soon as what you are doing causes her sexual pleasure.
While male desire comes in an unbroken exponential curve, female desire moves in waves becoming larger over time. With much sexual experience, these waves change and meet in the middle. If the woman experiences something as rather neutral this does not mean that she does not enjoy the overall sex – the next pleasure wave may already be on its way and kick in mere seconds later. If she, however, shows that something feels neutral and does not get better over half of a minute – or shows any reaction that you do not understand – pause your movements, and ask her what she wants you to do right now. If she is not able to tell you because she does not know for sure either, encourage her to experiment a little with her body. A self-confident woman will begin to experiment by herself.
Give her some time and space: She will not (be able to) find the perfect position immediately, and may have to readjust the position of her arms, legs or pelvis several times, before she wants to continue penetration. She may even request you to continue your movements, only to signalize shortly afterwards that she needs a pause again because the position does not feel as good as she has thought.
If she is making little corrections to her position, these have their purpose: By moving away from you, she is probably correcting too much pressure, or too deep penetration. By moving towards you, or to the side, she adapts your stimulation to be most effective. When this happens, do not readjust your own body, as this confuses the situation again. Just continue whatever you were doing before, and feel how she is enjoying you.
Do not ask her immediately after a change, whether she finds it better – as her body must first adjust itself to the new conditions, she won’t be able to know that so quickly. Again, just continue: If the change was a good idea, you will recognise this by her renewed signs of pleasure. If you are unsure, you can ask her of course – but allow for some time delay.
The following solutions are frequent:
- To shift the position slightly
- To apply or reapply additional lubrication
- To wipe over parts that are too wet (as this is causing insufficient stimulation)
- To change speed
- To change depth
- To change entirely into another sex position
- To alter the position so she can touch herself to enhance pleasure.
A likely result of her experimenting will be that she will touch her clitoris, use a toy, or rub against something in order to come. This can increase pleasure for her before, during and after penetration. She may not be able to come through your penetration alone. If this is a surprise to you because you have seen women come by penetration many times in movies or porn and you wonder whether something is wrong with her or with you, don’t worry, as you have fallen prey to a very common sex myth:
Women do not orgasm with their vagina, but with their clitoris. The most sensitive parts of the clitoris lie outside the vagina, around and below the visible clitoral head. Only a minority of women is able to orgasm just by penetration, because an inner part of her clitoris has grown into a lucky position and is reached by penetration. According to a study from 2017, that minority is one out of five, although in my personal experience, the number is significantly lower. So, if you had 3 ex-girlfriends, and 2 hook-ups before now, and all of them came just by penetration, or at least claimed to, then, in all probability, at least four of them were faking it, and maybe one was telling the truth.
All these behaviours are healthy and form an essential part of good sex since they make it possible to find the best conditions under which all individuals involved get the most pleasure out of what’s happening.
Should you find the results of her experimentation “weird” or disconcerting at some point, be careful, as this is your internalized toxic masculinity speaking. Your sex partner was raised in the social role “woman”, which means that she has been shamed for her sexual desires by the majority of her social environment, for her whole life. To feel her body and sexuality with you watching, and, especially, to experiment with that, has already required quite some courage. If you get impatient, unnerved or derogatory about what she is doing now and show it openly or comment accordingly (“You look strange”, “Ugh, what are you doing now?!”, “Are you a slut, or what?”, etc.), this can mean that:
- This is the last time she has sex with you.
- Annoyed, she breaks off sex, and confronts your unfair behaviour.
- She stops experimenting, and just goes through the motions of what you want. This can last for weeks or months, with boring formulaic sex – or no sex at all while she gets creative on excuses (every time you try to initiate sex, she is suddenly suffering from “migraine”). By unconsciously continuing toxic masculinity, you encouraged her to unconsciously drop back into toxic femininity.
You can rectify this by treating her “weird” sexual desires as a natural part of her: Stop slutshaming, and stop being mean, even as a joke. You wouldn’t want her to make a disgusted face after seeing your o-face, either. The sooner you change this for good, the more likely she will trust you again, so that you can resume your quest for good sex.
The best strategy is simply watching her experimentation without comment, and being helpful (by adjusting cushions, handing lubricant or sex toys, etc.). If you notice that you are becoming impatient, relax, and remind yourself that sex will not always be like that, but that she is finding techniques right now which she will be able to apply much faster in a few months, because she is developing a better feeling for her own body, her sexual desires, and you as sexual partner. What you can and even should tell her, are compliments (“You look so hot!”), or if sex acts she is performing on you become physically unpleasant (“Ow! This doesn’t work, could you try … ?”)
At first glance, a sexually inexperienced woman, who would like to enjoy the sex with you, but simply does not know how yet, looks the same as an intentionally ignorant woman, who has no interest in mutual pleasure, but uses sexual intercourse as a sort of currency instead, in order to obtain romantic attention, gifts or financial support (“a kept woman”). If you apply all these measures, you will be able to recognize without doubt which of these two types you have encountered.
You have met an intentionally ignorant woman, if she:
- Does not react to your requests to tell you what she likes or dislikes – both during sex, and in discussions afterwards.
- Claims that she would like to be more interactive during sex, but then freezes and does nothing, and never addresses the topic by herself again.
- Snaps at you when you pause during sex to ask her what she wants.
- Tells you that your discussion attempts would be “unnerving” or “immature”, and that “a real man” would know what she wants without asking – or, that a former sex partner would have known it all by himself.
Should she show one of these reactions, best break off sex and demand fair behaviour. If she is honestly confused about what’s going on, she has probably reacted destructively as a pre-emptive strike because she has hastily assumed that you will shame her as soon as she shows sexual initiative, like other men before you. In this case try to be very friendly and ensure her that you will enable her sexual wishes just as you pursue yours, in other words, that you will be fair. Should she, however, show no willingness to learn and tries to put up a fight instead, get up and out, even if the sex partner is your girlfriend or wife. Better an open conflict, that forces her to drop her game and communicate so that you might have better sex afterwards, than the prospect of lifelong bad sex.