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.
When I first wrote Sex Ed for Bi Guys, I had in mind men whose sexual experiences had been mainly with cisgender women. As time went on, though, bi+ guys who had been mainly with other cis men started to contact me. They wanted to explore sex with women, with a trans dude or with an AFAB nonbinary person, and they wanted pointers. You may be one of those guys. Or maybe you just don’t have much sexual experience, and you’re wondering how sex with someone who owns a vulva works. Maybe you have those sex parts yourself, and you want to learn more about sex. If any of these are the case, then. . .
Welcome to this four-part miniseries about having sex with women, transmasc and AFAB folks. This first part introduces a few things that will get you in the right mindset to become a great partner. It talks about some preparations you should make too before you end up in bed with someone. Part 2 will talk about all the fun bits a clit and vulva owner has. Part 3 will cover a bunch of different sex acts you can enjoy with a partner. Finally, part 4 will focus on actual f***ing.
On words and gender
You’ve noticed my choice of words: “a clit and vulva owner.” I expect you’ll use the info in this guide mainly with cis women. Yet not everyone born with those genitals are women.
Many trans guys still have a clitoris and a vagina, and will never have gender affirmation surgery on their junk. Likewise, many nonbinary people were born with that sexual equipment. Trans women who’ve had gender affirmation surgery on their genitals also have a clitoris and a vagina; I’ll talk about them too. This guide applies to sex with anyone who owns that equipment, no matter their gender. So you will know how things work the day you end up having fun with a trans or nonbinary person.
Many trans guys don’t use terms like vulva, clitoris, vagina, or any typical slang terms for those sex parts. They avoid these words because of their association with female genders. They might refer to their “clit” as their d**k, and to their “vagina” as their front hole or bonus hole. I’ve seen the term boyp***y thrown around too. Some nonbinary people also dislike feminine terms.
Yet, some trans guys and nonbinary peeps are comfortable with the classic terms. So I go back and forth in this post between using the “female” terms and more neutral terms, like front hole or canal.
The golden rule of amazing sex: communicate
If you’re going to remember just one thing from this post and forget everything else, it should be this: communicate, communicate, communicate! That’s the key to sex that blows the socks off everyone involved. Get comfortable with the idea of saying what turns you on and what you don’t want.
Make your partner comfortable with expressing the same thing. Tell them you want to hear what works for them, and what doesn’t. Let them know too that when they want the two of you to slow down, to change what you’re doing, or to stop everything, you will respect that. Ask for permission before you try something new with them, and make it clear they can say no. Look for signs of enthusiastic consent.
Hopefully, the two of you—or three, or four—will agree on plenty of sexy things you can do together. Guide each other through doing these in the way that feels the best, and don’t waste time on stuff that doesn’t feel great for everyone.
This level of communication puts some people off. “Talking ruins the mood” is a hard-to-kill myth that Hollywood movies and television foster—and I hate to say it, porn too. But you know what really ruins the mood? When someone fingering you hurts like hell because you have vaginismus. Or when a lover insists on trying stuff you don’t want to do, or keeps doing the wrong way something you wanted. No one reads minds either, and good communication lets you go directly to the stuff the two of you find hot and exciting.
Partners who are trans or nonbinary
Communication matters too when you or your partner are nonbinary or trans. You need to talk about what’s dysphoric and what isn’t, and what each of you likes best in sex. You can also talk about which words are okay to use for each other’s sex parts and for dirty talk if they’re into that. It’ll help everyone have the best possible time, and minimize the risk something will go to s**t.
Sex with women, transmasc and AFAB folks: sexual health and contraception
Talking about each other’s sexual health will matter too at some point. You can discuss your HIV status, any other STI you or your partner may have, how you usually protect yourselves for various sex acts, and when you were each tested last. This is intimate information though that someone you’ve just met—or yourself—might not want to share, and that’s okay. Still, this conversation becomes important when someone becomes a regular lover and you want to relax your safer sex practices. You or your partner could have an STI without knowing, as HIV and many STIs often don’t have symptoms. So getting tested together helps keep everyone healthy.
Finally, talk about which contraception methods you’re using when one of you can get pregnant—trans dudes can get pregnant, FYI. Never assume a partner doesn’t have an STI, or that they’re using a contraception method, just because they’re open to have sex without a condom.
So good communication is the golden rule of sex. It’ll prevent unpleasant things from happening, and it’ll put everyone on the right track for some great times! And frankly, knowing how to communicate will give you an edge over many heterosexual men…
Sexual roles and preferences when you have sex with women, transmasc and AFAB folks
Heteronormative expectations make their way into people’s heads when it comes to sex. These put pressure on folks to take on given sexual roles. This is even truer when the person you’re having sex with has a different gender or a different sexual equipment than yours. First off, bi+ guys often enjoy different sex acts depending on their partner’s gender. For example, you could be a bottom with cis men, but more dominant with cis women—a lot of bi guys describe that as their experience. Yet your gender, your partner’s gender, or your respective sex parts shouldn’t decide what must happen in bed.
It’s not because someone has a front hole or a p***y that they have to be the one taking a c**k. It’s not because you have a d**k that you have to be doing the penetrating either. In fact, some cis guys don’t like penetrative sex, but there’s pressure for them to do it, especially during man-woman sex. You can be a man having sex with a woman and be the submissive one. You can be a trans dude who tops exclusively—or who only likes when it’s nonbinary folks or women who penetrate you. Or oral sex can be your jam as you don’t care for penetration.
Still your preferences could change with a partner of a different gender. Maybe with someone of a certain gender you’re not interested in genital sex, but love roleplaying kinky scenarios. Or maybe you’re a power bottom with other guys, yet you dream of tender, vanilla sex in the missionary position with a woman. This is your sex life. You and your partner make the rules. It’s all about having an amazing time with each other, no matter what sexual activities you end up doing.
When the BS starts
Some partners will be put off when you want to do something that goes against heteronormative expectations, and this can creep into biphobia or cisnormativity. For example, some cis women will think you’re “secretly gay” when you ask them to peg you. Or a partner will expect you to take c**k because you have a front hole, and you wanting to be the top will weird them out.
It’s difficult to handle those situations. Sometimes a heart-to-heart about stereotypes and heteronormativity can work, but some partners will just be set in their views. This hurts when you’re emotionally attached to the person. On the other hand, many partners will find your attitude a refreshing change when they realize you’ve worked on overcoming heteronormative and cisnormative ideas. These get in the way of a lot of people enjoying a wholesome sex life.
Your perspective is unique
When someone’s sex parts are different than yours, you learn a lot from having sex with them. It’s an opportunity to have intimate discussions on how your respective bodies work, as well as on what you want and don’t want from sex. An exciting part of being a bi+ guy is that you can bond sexually with another man whose body is similar to yours. Yet you get to explore too with people whose gender and body might be uncharted territory to you.
You experience more than these individual adventures. These give you a perspective that change the sex you have with each person in ways monosexuals know nothing about. As they say, the whole is more than the sum of its parts.
The Scout Motto: be prepared
Prepare for sex – whether you expect it or not. In fact, it’s unexpected sex for which you should plan ahead most.
Keep your genitals clean, especially for sex with women, transmasc and AFAB folks
The first time a woman went down on me, her reaction was “thank God, you’re clean!” According to many people, sexual hygiene is a frequent problem with men. When necessary, excuse yourself to the bathroom and wash up your junk in the sink—it’ll often be enough.
Carry your brand of condoms with you at all times if using them matters to you
If using condoms for sex is important to you, carry them even when you’re not expecting sex to happen. Many people who care about safer sex often end up having unprotected sex when sex happens unexpectedly and there are no rubbers around.
If you have a penis, carry your own condoms to make sure they’ll be of a brand and a size you find comfortable. Sizes vary from one brand to another. For example, Durex condoms are much tighter than those from Lifestyle. A lot of people have a bad experience because they think they can just put on any condom. Just like you try shoes before you buy them, you should try on a brand or size of condom while you masturbate, before you use it for the first time during sex with a partner.
Also, don’t carry condoms in your pockets, wallet, or loose in a bag with other objects. Heat, pressure, friction, and pointy things are bad for condoms. A small cigarette case from the dollar store is the perfect size to carry a few condoms. You can carry dental dams or flavoured condoms too for protection for oral sex. Don’t put a flavoured condom inside a vagina, though: they increase the risk of a yeast infection. Latex or nitrile gloves can make fingering and fisting safer too. Many people don’t use protection for oral sex or penetration with their hands, but some people feel safer with them. It’s good form to ask a partner if they prefer that.
Keep lube handy, even for sex with women, transmasc and AFAB folks
Even if vaginas self-lubricate, having lube with you is a good idea. Not everyone lubricates easily, so putting on some extra lubrication helps make things slide in—and out, and in, and out… Lube is useful too when a larger than average penis is involved, when someone tries to fit in a larger sex toy, or when you’re giving vaginal fisting a go.
This is it for part 1. In part 2, we talk about all the naughty bits a woman, or a transmasc or AFAB person might end up sharing with you!
