This is the SFW/censored version of this post. You can view the uncensored, sexually explicit version here on Pillowfort. All images are borrowed from the internet and are in the post because I like them. If you are the copyright owner or a person in the image, contact me: I’ll gladly credit you, or remove the image at your request.

This is the final part of a four-part series on how to have sex with the owner of a clitoris and vagina – or whichever terms a person prefers for their sex parts – whether they be cisgender women or nonbinary and trans folks. This week, we’ll conclude by looking at f***ing, and how to ensure everyone taking part in it is having a great time.

Heteronormativity – expectations straight people have created on what sex should be like – puts penis-in-vagina sex on a pedestal, treating it like the be all, end all of sex. But as I’ve said in part 3, front hole penetration is just one sex act among many. Some people love it; some people like it but prefer another act; and some other people are not into it – and that’s okay. Sex is about whatever makes everyone involved feel amazing, and you are the ones making the rules.

Having the final part of the series focus on PiV goes against what I’ve just said. But there are more things to say about that sex act than with most others in a guide on having sex with people who have a vagina. Pregnancy is a possibility. Of all the sex acts I go over in this guide, it’s also the one with the highest risk of HIV transmission. Front hole f***ing can also be tricky and because of heteronormativity once again, it carries a lot of expectations about “performance”. So we’ll be going over all that here.

Avoiding a surprise baby

When you’re used to having sex with people who lack a uterus, you don’t have to think about avoiding an unplanned pregnancy. You’ll have to think about it though whenever a penis gets close to a vagina. So when making a baby isn’t on the menu, keep semen away from the front hole or from inside the canal. Also, precum (pre-ejaculatory fluid, the liquid that oozes out of the penis when the person is turned on) sometimes contains sperms. So when penis-in-vagina sex is what your partner and yourself want, you will have to figure out a contraception method or two. Here’s a breakdown of methods you’re most likely to be using.

Condoms: Condoms are easier to get your hands on than other contraceptives, and many resources hand them out for free. They’re great too at preventing the transmission of HIV and other STIs that body fluids can transmit. They also reduce the risk for STIs that spread though skin-to-skin contact, although that protection is less effective. Some people dislike that condoms cut off direct body contact. Others (often with a latex kink) like the sensation of the material. Many people don’t mind either way. They can be tricky to use too for someone who’s taking estrogen-based HRT. Although condoms are great at preventing pregnancy when you use them perfectly, a lot of people don’t: in reality, 10 to 18% of people who use condoms as their only contraception method become pregnant every year. So if you absolutely want to prevent pregnancy, either get real good at using those condoms, or combine them with another method.

Hormonal methods: These are hormones taken by the person with the uterus to disrupt the cycle of ovulation. The most well-known is the pill, but there are others, like patches, vaginal rings, or injections. People interested in hormonal contraception should check with their doctor or a nurse which one is better for them, as well as possible side effects (even more so when they’re on HRT). Hormonal methods are very effective and as a bonus, some can help people with painful periods, but they don’t protect from STIs and they can have side effects (sometimes serious). Many methods (the pill especially) depend on the person being diligent in respecting the schedule for their prescription.

IUD: It stands for Intra-Uterine Device. An IUD is an contraceptive object (see above) that a doctor puts inside the uterus; it prevents a fertilized egg from implanting itself into the uterine wall. IUDs are very effective and can remain in place for years. They can have side effects though and on rare occasions, serious complications. They remain a good, long-term contraception method, without the permanence of sterilization.

Sterilization: These are surgeries that make owners of testicles or ovaries permanently unable to conceive. They include vasectomy (cutting the canal that takes sperms from the testicles to the seminal vesicle) and tubal ligation (blocking or removing the Fallopian tubes that take the eggs to the uterus). Sometimes hysterectomy (removing the uterus) is preferred, in particular for some trans guys. Sterilization is extremely effective, but permanent (although sometimes reversible). Recovery for most surgeries is usually a matter of days.

Not ejaculating inside your partner during penetration: As a main method of contraception, it is unreliable and you shouldn’t depend on it unless you and your partner can live with a moderate risk of unplanned pregnancy. Ejaculation can happen by accident during penetration, and sperms can be in precum. As a secondary contraception method though, it can work well: you or your partner is very unlikely to get pregnant when you use a condom and there is no ejaculation inside or near the front hole.

Testosterone-based HRT for trans men and nonbinary folks isn’t a contraceptive method. Although it decreases the odds of conception and sometimes causes infertility (temporary or permanent), some people on HRT do get pregnant.

If you’re comfortable, have the contraception conversation with your partner to see what methods you are each using (if any), and what odds of pregnancy you both find acceptable. Discussing what would happen in the case of a pregnancy can be a good idea also. Never assume that a partner who agrees to have sex without a condom is using another contraception method: sometimes a person’s horniness, intoxication, or need for a moment of close physical intimacy makes them take risks. In the best of worlds, have those conversations at a time when sex isn’t immediately on the table. But in doubt, consider using condoms.

Being savvy about HIV

Of all the acts I’ve talked about in this series, penis-in-vagina sex (with a flesh-and-blood d**k) is the one that carries the highest risk of transmitting HIV (the AIDS virus) (penis-in-butthole sex carries a higher risk though). Vagina owners themselves are quite at risk (stats about HIV incidence in women who have heterosexual sex are quite high, and staggering in certain parts of the world; unfortunately, public health departments rarely track HIV incidence among nonbinary and trans folks who also own a vagina), as taking in the d**k is riskier than being the person inserting the penis, especially when there’s an ejaculation inside the canal. PiV without a condom is considered a high risk for HIV transmission when one of the partners is infected. Many people don’t know they have been infected, and might never have been tested. The virus is the most contagious in people who are not under treatment (effective treatment can reduce or prevent transmission completely). The virus is also more present in racialized and stigmatized communities (because social and structural factors affect its spread).

If HIV is a concern to you, using condoms consistently and properly grants a great protection against the virus. Wear a condom from a brand and a size that feels comfortable to you, as condoms that are too tight break more easily, and condoms that are too loose can slip off. As a bi, pan, or polysexual guy, you can also have access to PreP easily in many places, as public health authorities make it more available for men who have sex with other men. PreP is HIV medication that you can take everyday to protect yourself from HIV, or as needed when you don’t have sex regularly with partners whose HIV status you don’t know. PreP can be a good alternative when condoms don’t work for you, although it doesn’t protect from other STIs; it has side effects; and it doesn’t prevent pregnancy. If you believe you might have been exposed to HIV, you can also go to the hopital urgently to receive emergency HIV treatment and reduce the risk you’ll become infected. In that case, the faster you go, the better – ideally in the next few hours after the risky contact happened.

Finally, there is an idea that bi men are a bridge for infecting heterosexual women with HIV; this is a long-enduring and devastating myth. The vast majority of HIV infections in heterosexual women happen during sex with a heterosexual man. Still, we are more likely to become infected than men who only have sex with women. So I encourage you to protect you own health – you deserve to be healthy – and the health of your partner, and to get tested regularly for HIV and other STIs. But us bi, pan, and polysexual men are not to blame for the HIV epidemic. We have in fact been at the forefront of early AIDS activism.

But now let’s – finally – talk about the fun stuff.

Enjoying penetration

People tout f***ing as the main event of a sexual encounter, especially when a penis is involved. Yet sex is whatever the persons involved decide it is. Some folks love penetrating someone else; some others love taking someone or something inside their front hole; but many people don’t care that much – or at all – about these acts. It’s not because there are a vagina and a penis that the former will take in the latter. In fact, there are even heterosexual cis men who don’t care much for penetration, and who would rather focus on other sex acts they enjoy more. There are all kinds of reasons people could not be into penetration: maybe they don’t like it; maybe they worry about pregnancy, and that gets in the way of their enjoyment; maybe it’s dysphoric; maybe there’s trauma they associate with the act (which can be the case for any sex act); maybe they do penetration only in long-term relationships. Still, many people love f***ing and can’t get enough of it.

While people usually penetrate with a flesh-and-blood d**k, they can also use a sex toy, whether they use a harness (strap-on) or not; fingers and even a hand are also an option, as I’ve said in part 3. When the person doing the penetrating is a trans dude or a nonbinary person, that “toy” might be their actual penis (which is sometimes part of an assorted collection). But no matter what implement you will end up using, the basics are the same.

First off, when your main experience with penetration is anal sex (presumably with another dude), you’ll discover many differences. Angles and positions work differently. The sensitive spots inside the canal don’t work the same way either, even though the g-spot and prostate are similar. Vaginas self-lubricate also, and lube can be unnecessary when the person taking something in has been turned on for a while; but have it on hand still, especially when penetrating with something bigger than the average c**k (a reminder that it would be 13 cm in length and in girth when hard).

For actual penetration, make sure the person taking the c**k or toy is turned on enough – they’ll be inserting something bigger than the other things you have been putting in there so far. Choose a position you both believe will work well at first. For beginners, if you’re doing penetration with a flesh-and-blood c**k, missionary or cowgirl/boy/person is good starter. Missionary position helps prevent the penis from going too deep and hitting the cervix – which is painful for most people – and cowperson style allows the partner taking the c**k to control the pace and rhythm of the penetration. The front hole can be difficult to find, and it’s less obvious than the butthole (don’t get them mixed up, your partner won’t like the surprise). Ask your partner to guide your penis inside them (or vice versa when you have a front hole they’re penetrating); it helps, and it can be hot to do so. Start slow, and communicate with your partner to make sure everything is okay. Vaginal penetration shouldn’t hurt – even with an hymen in place in most cases. When there’s pain, do your best to help your partner feel relaxed and comfortable, take more time to get properly turned on, add lube, go slower, or try an easier position. Some folks will have unexplicable pain whenever they try vaginal penetration, and nothing you’ll do will allow painless penetration – it’s a situation in which they should see their doctor, as there could be a medical cause.

[Drawings of a woman and a man in various sex positions]

People talk about sex positions as if they were central to vaginal sex, but they’re more a matter of what allows both partners to be comfortable and what makes it easier to get the right stimulation. Many people also might like the visual aspect of the position, the kind of intimate contact it allows, or the erotic charge it holds. But sex positions aren’t a checklist you need to clear. Explore them naturally. Talk with your partner about what they’d like to try, and give it a go. Sometimes you can switch while the d**k is still inside, sometimes you need to pull out. Positioning and penetrating can be clumsy and awkward, but that’s okay. There’s a lot of clumsiness that comes with trying to line up two bodies to get each other off – embrace it, and learn to have a laugh together at the awkward moments. I can’t tell you what positions you and your lover will enjoy the most – it’s for the two of you to find out, but that’s part of the fun of sex.

Also, when both front hole and anal sex are on the menu, remember that putting something that’s been inside a butthole into a vagina is a terrible idea – it can cause vaginal infections. So clean that d**k or toy after butt sex, or put on a new condom.

Ejaculation timing “issues”

When you’re penetrating with a flesh-and-blood penis, timing your orgasm becomes part of the equation. Some people ejaculate quickly, some can’t come unless they use their own hand, and many fall somewhere in-between – and all are okay when you can be candid about how your d**k works and adapt the sex you’re having to how your body functions. So-called “premature ejaculation” applies to 25 to 40% of penis owners; but can you take the sexual response of such a large portion of people and label it a “dysfunction”? It’s ridiculous. It’s just the way their body works. If two minutes of vaginal sex pretty much guarantees you’ll ejaculate, be upfront about it. Focus on other things to help your partner come, and save penetration for a nice finish. Some people will find it hot that their partner can’t resist coming inside their p***y; others would rather get f***ed hard for a long time – sex acts function differently for each person. At this point, it’s a matter of whether the way front hole sex works for you is compatible with your partner’s sexual tastes. But because heteronormativity puts penis-in-vagina sex on a pedestal, society stigmatizes not enjoying it or having the experience of PiV unfold outside of certain norms and expectations. Yet its just one sex act among an endless list of pleasurable things you can do with a partner.

There can also be unease when you can’t ejaculate from front hole sex. You or your partner might feel inadequate that you couldn’t get off like that, but it’s just the way your body is wired. Vaginas don’t offer the most precise stimulation, and sometimes it takes a mouth or a hand to stimulate you just right. You can say the same of penises: they aren’t the most accurate tool to get someone off either, and many partners won’t come from PiV stimulation alone. That’s also okay. Both of your bodies work fine. It’s unrealistic to believe that everyone can orgasm from penis-in-vagina sex but once again, there’s stigma because it’s seen as the be-all, end-all of sex. But it isn’t.

If it’s important to you though, you can learn to have more control over when you ejaculate, just like you can get your penis used to ejaculating to a broader range of stim. Control comes from knowing your body well and recognizing when you’ll reach the point where ejaculating becomes inevitable – and that means slowing down or pausing to cool off a bit. Practice getting close to that point, and stop before you ejaculate; then lather, rinse, and repeat (not literally). Some folks do this for fun: it’s called edging. When you do that on a regular basis, your body gets used to being in that zone of sensation without triggering ejaculation, and you’ll gain better control. Then you can play with keeping yourself right on the edge of orgasm for as long as you can before stopping. You can make a game of it, whether by yourself or with a partner who’s in on it.

As for teaching your d**k to ejaculate from a wider range of stimulation, it involves varying your masturbation technique (Jackin’ World [some sexually-explicit drawings] has many suggestions) to find other ways of making yourself come. Avoid your usual go-to for a few weeks, and don’t ejaculate for a few days to have an easier time getting yourself off in a way that’s different from your usual. Keep at it, and your d**k will learn other sensations that can get it off. Doing this won’t guarantee that you’ll be able to come from PiV sex, but you’ll have an easier time coming in other ways besides your own hand. Still, whether you’re someone who comes super easily or only by your own hand after lengthy and consistent stimulation, none of these exercises are a substitute for learning to love your body and how it works, just the way it is.

So this wraps up the Sex with a clit owner miniseries. If you have a clit and front hole yourself, I hope you had the opportunity to learn more about your body, and that what you’ve read here will make sex more pleasurable for you. If you’re a d**k owner – like most guys who’ll read this series – having sex with someone who has a different anatomy than yours can be intimidating – more than most men care to admit. I hope you feel better equipped to approach this and share amazing moments with your partners. But as always, you and your partners are the ones who know the most about your bodies and your desires. Be present for each other, talk with each other about the sex you want, and you’ll be well on your way to having a great time together.

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Check out all Sex Ed for Bi Guys posts here, including articles such as ”Am I bi?”, Butt Sex 101, and Dating Men, Women, and Nonbinary Folks.