Exciting sex with women, transmasc and AFAB people: Happy f***ing!

This is the censored version of this post on having sex with women, transmasc and AFAB people. You can view its uncensored version with sexually explicit (NSFW) photos on Pillowfort.

A couple of lace panties, one pink and the other, black. Captions overlay the image and read, "This should be a guy pulling down his partner's undies right before some PIV fun. You get some racy panties instead." You can expect some different underwear than usual when you have sex with women and many transmasc and nonbinary folks!

This is the final part of a four-part miniseries on how to have sex with women, transmasc and AFAB folks. You can find part 1 here, part 2 here and part 3 here. In this last part, we look at f***ing, and at how to make sure everyone taking part in it has a great time.

Straight people have created heteronormative expectations on what sex with women should be like for men. These expectations put penis-in-vagina sex on a pedestal. They treat it like the be all, end all of sex. Yet as I’ve said in part 3, front hole penetration is just one sex act among many. Some people love it, some like it but prefer a different act, while others aren’t into it—and that’s okay. Because sex is about whatever makes everyone involved feel amazing, and you’re the ones making the rules.

Having the last part of the series focus on PiV kinda goes against what I’ve just said. Still, this is a guide on having sex with people who own a vagina or a bonus hole. There are more things to say about PiV penetration than about other sex acts. Pregnancy is a possibility. Of all the sexual activities I go over in this guide, it’s the one with the highest risk of HIV transmission too. Front hole f***ing can also be tricky. Because of heteronormativity once again, this act carries a lot of expectations about “performance.” So we’re going over all that here.

Avoiding a surprise baby when you have sex with women, transmasc and AFAB folks

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 have to think about it, though, whenever a flesh-and-blood penis gets close to a vagina, which is likely during sex with women or with a transmasc or AFAB person. So when making a baby isn’t part of the plan, keep semen away from the front hole. Also, precum sometimes contains sperm. So when penis-in-vagina sex is what you and your partner want, you will have to figure out a contraception method or two. Here’s a breakdown of methods you’re most likely to use.


Cisgender men who have sex with other men are often well-used to condoms. Still, these take on an extra contraceptive purpose when you have sex with women who are cis and with other AFAB folks.

Condoms are easier to get your hands on than other contraceptives. Many services hand them out for free. They’re great too at preventing infection with HIV and other STIs that body fluids can transmit. They also reduce the risk for STIs that spread though skin-to-skin contact, but 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. Condoms can be tricky to use too on the penis of someone who’s taking estrogen-based HRT.

While 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 when 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. Still, they don’t protect from STIs, and they can have side effects that are sometimes serious. Many methods—the pill especially—depend on the person respecting the schedule carefully for their prescription.


IUD stands for intrauterine device. It’s a 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 one 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.


These are surgeries that make someone 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 someone prefers hysterectomy—removing the uterus—like for some trans guys. Sterilization is extremely effective but permanent, though sometimes reversible. Recovery for most surgery is usually a matter of days.

Not ejaculating inside your partner

A geyser erupting, with a rainbow formed by the spray. There is snow on the ground, and the sky is blue with some clouds. There are tourists and tourism facilities in the background. Captions overlay the image and read, "This should be a guy ejaculating on his partner's belly. You get a lame geyser metaphor and a rainbow instead." Not coming inside your partner can be a good backup contraception method when you have sex with women or with a transmasc or AFAB person, but it shouldn't be your main method to rely on.

As a main method of contraception during sex with women, transmasc and AFAB people, the “pull-out” method is unreliable. You shouldn’t depend on it unless you and your partner can live with a moderate risk of an unplanned pregnancy. Ejaculation can happen by accident during penetration, and there can be sperm in precum. As a backup contraception method, though, not coming inside your partner can work well. Neither you nor your partner are likely at all to get pregnant when you use a condom and there’s no ejaculation anywhere near the front hole.

“What if I’m on T?”

Testosterone-based HRT for trans men and nonbinary folks isn’t a contraceptive method. It does decrease the odds of conception, and it sometimes causes temporary or permanent infertility. Still, some people on HRT do get pregnant, so it’s not a reliable for contraception.

Talking about contraception

If you’re comfortable, have the contraception talk with your partner to see what methods you are each using, if any. Figure out what odds of pregnancy you both find acceptable. Discussing what would happen in the case of a pregnancy can be a good idea too.

Never assume that a partner who agrees to have sex without a condom is using another contraception method. Sometimes, someone’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. When we have sex with women, transmasc and AFAB folks, it’s good to plan for the possibility of a baby happening.

Being savvy about HIV matters too for sex with women, transmasc and AFAB people

Three stylized silhouettes traced in yellow over a solid black background. They represent the saying, "see no evil, hear no evil, speak no evil." Each has an X on their torso. The first has its hands on its eyes, the next, on its hears; and the last, on its mouth. Below the silhouettes, the slogan "Silence equals death" of ACT UP—the AIDS Coalition to Unleash Power—is written in large, pink letters. We need to talk about HIV, including when we have sex with women, transmasc and AFAB people.

HIV still matters when we have sex with women or with a transmasc or AFAB person. 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 with the highest risk of spreading HIV. Still, penis-in-butthole sex has a higher risk. Yet vagina owners can be exposed even when they don’t have anal sex.

Stats on how HIV impacts women who have sex with men are quite high. These are even huge in some parts of the world. Sadly, public health services rarely track how often HIV happens among nonbinary and trans folks who are AFAB. Yet their risk of HIV infection is probably comparable or higher than for cis women. Taking a d**k is riskier than being the person who inserts the penis in, especially when an ejaculation happens inside the canal.

PiV without a condom has a high risk of spreading HIV when one of the partners is infected. Many people don’t know they’ve been infected, and might never have been tested. The virus is the most contagious in people who aren’t under treatment. Indeed, treatment that’s effective can reduce or prevent transmission completely. The virus is more present too in racialized and stigmatized communities, because social factors help it spread.

Preventing HIV

If HIV worries you, using condoms well and consistently gives a great protection against the virus. Wear a condom from a brand and size that’s comfortable to you. 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. Public health services make PreP more available for men who have sex with other men. PreP is HIV medication that you can take every day 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 is a good alternative when condoms don’t work for you, though it doesn’t protect from other STIs. It has side effects, and it doesn’t prevent pregnancy either.

Also, an HIV-positive partner can’t pass the virus on when their treatment is effective to the point we can’t detect the virus in their blood anymore. That’s called having an undetectable viral load.

Finally, if you believe you might have been exposed to HIV, you can go to the hospital urgently to receive emergency HIV treatment, and reduce the risk you’ll become infected. When that’s the case, the faster you go, the better—ideally in the next few hours after the risky contact happened.

Truth be told, most cis men who have sex with women don’t have all that information on preventing HIV, and neither do their partner. Us queers in general just tend to know more about that topic.

The lie that we make women sick

There’s an idea that bi men are a bridge for infecting heterosexual women with HIV. This is an enduring and devastating myth. The vast majority of HIV infections in heterosexual women happen during sex with a heterosexual man. Still, we’re more likely to become infected than men who only have sex with women. So I encourage you to protect your own health—you deserve to be healthy—and the health of your partner. Get tested regularly too for HIV and other STIs. But us bi+ men aren’t to blame for the HIV epidemic. We have in fact been on the frontlines of AIDS activism since the start.

But now let’s at last talk about the fun stuff.

Enjoying penetration during sex with women, transmasc and AFAB folks

A bed made from wooden logs. The bed cover, pillows and cushings have burgundy, dark green and tan lines. Captions overlay the image and read, "This should be a woman and a man in the missionary position. You get a rustic-looking bed instead." This position is a classic of sex with women.

People tout f***ing as the main event of a sexual encounter, especially when a penis is involved. Yet sex is whatever the partners involved decide it is. Some folks love penetrating someone else. Some others love taking someone or something inside their front hole. Yet 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 the latter in. 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. Some people only do penetration in long-term relationships. For some others, penetration is dysphoric, or there’s trauma they associate with the act—which can be the case for any sex act. 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 use a sex toy instead whether they use a strap-on or not. Fingers and even a hand are an option too, 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. Still, no matter what implement you end up using, the basics are the same.

Four Burmese punks standing side by side, presumably at an outdoors punk event. They're wearing battle jackets with studs and patches. The hair of each of them is colourful, and jacked up either into a mohawk or spikes. Captions overlay the image and read, "This should be two punk as fuck trans dudes snuggling naked. You get a Burmese punk posse instead!" Sure, we're talking a lot about sex with women in this miniseries, but a lot of folks with a bonus hole are guys.

It doesn’t work like anal sex

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 too, and you might not need lube when the person taking something in has been turned on for a while. Still, have it on hand, especially when penetrating with something bigger than the statistically average c**k—which would be 13 cm in length and 11.5 cm in girth when hard.

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 bad idea—it can cause vaginal infections. So clean that d**k or toy after butt sex, or put on a new condom.

Getting started

For actual penetration, make sure the person taking the c**k or toy is turned on enough, as they’ll be inserting something bigger than what you’ve 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 a good starter. Missionary position helps prevent the penis from going too deep and hitting the cervix, which is painful for most people. Cowperson style lets 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—and 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 a 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 inexplicable pain whenever they try vaginal penetration, and nothing you’ll do will allow painless penetration. This is a situation in which they should see their doctor, as the pain could have a medical cause.

Different positions for sex with women, transmasc and AFAB people

Drawings of a woman and a man in various sex positions

People talk about sex positions as if they were central to vaginal sex. Yet they’re more a matter of what allows both partners to be comfortable, and of what makes it easier to get the right stimulation. Many people might like too the visual aspect of the position, the kind of intimate contact it allows, or the erotic charge it has.

Still, 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. Yet the two of you can find out, and that’s part of what makes sex fun.

Ejaculation timing “issues”

A giant hourglass atop a cliff at sunset, when sand pouring through it. Captions overlay the image and read, "This should be a butt shot of a guy deeply engaged inside his partner. You get an epic hourglass instead."

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. All of these 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. Yet, can you take such a large portion of people and their sexual response, 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. There are others who would rather get f***ed hard for a long time. At this point, it’s a matter of whether the way that 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 puts down folks who don’t enjoy it, or who experience PiV in a way that’s outside the norm. Still, it’s just one sex act among an endless list of pleasurable things you can do with a partner.

Difficulties coming during sex with women, transmasc and AFAB folks

There can be unease too when you can’t ejaculate from front hole sex. You or your partner might feel inadequate that you couldn’t get off like that, yet 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 okay too. 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 a stigma because people see it as the be all, end all of sex. But it isn’t.

Splatter art of one of the symbols for bisexuality, the symbol for female and the symbol for male interlocked in an infinity loop. The art has the colours of the bisexual pride flags, the top part being pink, the middle, purple and the bottom, blue. The background is solid black. Captions overlay the image and read, "This should be a gif of a guy and a girl making out naked. You get this cool bi art instead!" Making out naked is a fun part too of sex with women, transmasc and AFAB folks!

Techniques to feel in better control

If it’s important to you, you can learn to have more control over when you ejaculate, and get your penis used to ejaculating to a broader range of stim too. Control comes from knowing your body well, and recognizing when you’ll reach the point where ejaculating becomes inevitable. That means slowing down or pausing to cool off at that point. Practise getting close to it, and stop before you ejaculate. Then lather, rinse, and repeat. 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. 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. 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 it can get off to.

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. You can be someone who comes super easily, or only by your own hand after lengthy and consistent stimulation. Still, none of these exercises are a substitute for learning to love your body, and how it works, just the way it is.

A rectangular rug on a wooden floor. There are drawing of leaves around its edge atop a brown border. The center look like a cracked tiled sprayed with an autumn colour palette. Captions overlay the image and read, "This should be two tattooed guys having front hole sex with each other. Instead you get a prettier rug than the one they're standing on."

Concluding the Sex with women, transmasc and AFAB people miniseries

So this wraps up the Sex with women, transmasc and AFAB people miniseries. If you have a t-dick or a clit yourself, I hope you had the chance 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.