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.
This is part 3 of a four-part miniseries on how to have sex with women, transmasc and AFAB folks. You can find part 1 here and part 2 here. In this third part, we look at all kinds of ways you can play with the body of someone who owns a clit or a t-d**ck to make them feel amazing.
It’s not just “foreplay” when you have sex with women, transmasc and AFAB folks
When it comes to men having sex with women, our society—which pretends nonbinary and trans people don’t exist—glorifies penis-in-vagina sex, and penetration in general. As a result, it calls all other sex acts leading up to it “foreplay,” as if the goal of every sexual encounter was for a penis to f*** something. Some people even say they didn’t have sex when there was no penetration. Yet they worked hard to make orgasms happen!
Penetration is just one sex act among many. It only needs to happen when both partners want it. In fact, many people prefer other sex acts that get called “foreplay.” Sex is whatever you want it to be, as long as it’s safe, sane, and consensual.
Fingering
Many people call masturbating someone with a vulva or bonus hole “fingering.” Hands and fingers are a lot more precise than d**ks for stimulating someone the right way. It’s also one of the safest sexual activities that involve touching someone else’s sex parts.
In practice, people don’t get HIV, or other STIs that sexual fluids can pass on, from masturbating someone else. Transmission of skin-to-skin contact STIs—like herpes or HPV—can happen, but it’s rare. Still, you should leave open herpes sores and genital warts alone. You should wash your hands immediately when contact happens. For herpes, infecting a different body area of the infected person is a risk too.
Yet masturbating someone else is far safer to your health, and that of your partner, than a lot of day-to-day activities, like riding in a car or doing sports. Maybe even a very low risk makes you anxious, though. When that’s the case, it’s okay to tell your partner you’d rather use latex or nitrile gloves, if just for your peace of mind.
When having sex with women, transmasc and AFAB people, you should prepare considering fingering is on the menu. Keep your nails short and round; few people like having their most sensitive areas jabbed by sharp nails. Also, you can wash your hands before you put them inside someone’s body. Still, the actual risks of infecting a vagina with stray bacteria are very low. Yet your partner might feel more comfortable when your hands are clean. Having lube available is a good idea too: the skin from the vulva is sensitive, and friction can make the experience unpleasant.
Sex with women, transmasc and AFAB folks: learning how a partner likes to masturbate
The best way to learn how to masturbate another person [explicit drawings of mutual masturbation] is to watch them masturbate themselves. They might be happy to put on a show! Masturbating in front of someone else makes some people uncomfortable, though. Still it’s okay to ask a partner if you can watch them jerk off. You can explain that you want to learn what makes them feel good. This is especially relevant if you aren’t used to having sex with women, transmasc and AFAB people, since their sex parts may be unfamiliar.
As always, communicate with your partner while you masturbate them. Have them guide you, and give you feedback on what feels great and what doesn’t. Everyone likes different things. What worked with a previous partner might not with the person you’re with at the moment.
Masturbating someone who owns a clit
Some clit owners—no matter their gender—like jumping straight into the action. Yet, most take longer to get turned on than someone with a d**k. So kissing, fondling, playing with erogenous zones, and rubbing their crotch—clothed or bare—starts the fun well when you have sex with women, transmasc and AFAB people. Ask your partner if they prefer you masturbate them with lube. You can play with most areas of the vulva and make it feel good, as it’s very sensitive as a whole. But the clitoris is usually where it’s at.
Some people like the head of their clit stimulated directly, but many people find that too sensitive. You can rub the glans through the hood, or around it instead. Before you put your fingers in your partner’s front hole, ask if that’s okay. Don’t assume it’s cool just because they’ve enjoyed your handjob so far. You can have a hard time finding the front hole when you’re not used to it, so ask your partner to help you out with that.
You can start with two fingers, but some people prefer—or require—just one at first. Your partner can enjoy a simple in-and-out thrusting motion. Yet you can look for the G-spot [guide on G-spot play, some sex toy photos; page retrieved from the Internet Archive], or engorged internal clit. Feel up the front wall of the vagina, towards the navel, a couple of inches in. Rubbing that spot with a back-and-forth “come hither” motion works well for many people. Faster isn’t always better. Some people prefer slow and consistent stimulation, so communicate with your partner on that. Also, some people just aren’t into G-spot play.
Remember that A-spot?
Sex with women, or with transmasc and AFAB partners can lead to trying some anterior fornix play [guide on A-spot play, some anatomical drawings]. If you’re curious about it, ask your partner before you go ahead. Expect to have to explain what it is—most people with a fornix don’t know about it. It can be weird to them when you start reaching for the far end of their canal without bringing it up first. The idea will make some partners uncomfortable, and that’s okay. Some others will know about their fornix, though, and they might know how to play with it; they can guide you then.
Fingers are sometimes too short to reach a given person’s A-spot. It’s easier to access when your partner lies on their back and pulls their legs and feet up: it shortens the canal. Move to the end of the front wall, towards the bladder and pubic bone, just above the cervix. Go slowly at first and avoid bumping the cervix – most people find that painful. But once you find that spot – many people say its texture is different – try a slow “come hither” motion. This is like G-spot play, but at the deep end of the front hole.
The sensation will be different for your partner than G-spot play, and they might not be into it. They might not feel anything special either. Still they could end up loving it, and you can explore together a new way of having a great time.
Using toys during sex with women, transmasc and AFAB people
Many toys exist for sex with women, transmasc and AFAB folks, for using on their own or with a partner. There are vibrating bullets. Some are vibrators that gyrate. There are U-shaped vibrating toys too that stimulate both the clit head and the front hole. And of course, there’s the classic non-vibrating dildo. Toys aren’t for everyone. Still many people love them and own an extensive collection.
Which toys work best on a person is personal too. One partner might be in love with their vibrating egg or bullet. Another one might not care about that, and prefer a curved glass dildo for G-spot or A-spot play. Sex toys are a huge topic [sex ed comic with explicit drawings] that I can’t cover here entirely. Still, they exist and they’re an option. Your partner might own their faves already but if you shop together, a good sex shop will have knowledgeable staff. They can advise you.
HIV and STI transmission is possible too through sharing toys. Still, it’s less risky than penetration with a flesh-and-blood penis. You and your partner—or partners—might plan on using the same toy on more than one person. So put a condom on the toy and replace it when the toy switches partners. Many toys can be washed easily with warm water and gentle soap. Some can be sterilized too by boiling them for 20 minutes.
A toy’s care depends on the material, and on whether it’s motorized or not, or waterproof. You should ask how to clean it when you buy it, or look it up online. Finally, many toys are made from silicone, and using silicone lube will damage them – so use water-based lube for those.
Front hole fisting
When you have sex with women and with transmasc or AFAB partners, fisting [guide on the topic, no explicit images] can come up. Still, it’s a sex act that many people don’t do, even though it’s better known than A-spot play. Fisting is demanding, and it gives a very intense sensation. You can’t improvise it—usually—and it’s not everybody’s cup of tea. The suggestion might freak some partners out. This is the kinkiest thing I’m bringing up in all the hand and penetrative play.
For some, fisting is impossible because of a combination of a bigger hand and a smaller canal. Some people love taking a whole hand, though. They’ll be delighted to have a partner who is game for fisting, and who knows how to approach it. Always discuss this beforehand with your partner, to make sure they’re into that and consenting. But talk about it too because this act of penetration demands both people be active. You can’t just decide to fist someone, and that they’re going to lie there and take it. They must do things on their end to ease your hand in. It takes good communication to get there and not hurt your partner.
Getting the hand inside
As usual with it comes to prepping for sex with women, transmasc and AFAB folks, keep those nails short and without snaggy ends. Have lube on hand—fisting needs a lot of lubrication. Using a nitrile or non-powdered latex glove makes things slicker and penetration easier. Your partner should be relaxed and very turned on. If they’re multi-orgasmic, it will help if they’ve come already. Lube your hand very well, especially the widest part.
Despite the name of the act, don’t form a fist with your hand. Put all five of your fingertips together in the shape of a snake head—think kung fu snake stance—or duckbill. You want a shape that starts small and narrow and that progressively gets wider. You can warm up with fingering and adding one finger at a time until you reach that shape. Talk with your partner to make sure they’re comfortable throughout. The knuckles are the difficult part. On your end, try a left-right screwing lightbulb motion more than pushing in. On your partner’s end, they can squeeze their PC muscle, and release it along with a big exhale – it can get your hand further in.
Lying on their back, tilting their head back, and stretching can create more room in their canal (but some people experienced with fisting prefer different positioning). Be patient, and take things as slowly as required. Fisting might not work, and it’s important to stop rather than hurt your partner. Respect each other’s limits. The fistee could end up orgasming from the motion of trying to fit the hand in, and the muscle contraction could push the fister’s hand out. That’s okay – enjoy their orgasm, and decide together if you want to give it another go.
Once the hand is in there
Once the hand is all the way in, it will naturally shape itself like a fist. The fister should keep their thumb outside their fingers when possible. Orgasms might happen while their hand is in there and vaginal muscles could squeeze it tight; it will be better with the thumb outside. The fister should put up with any discomfort, and always let their partner know when they’ll start removing their hand. You must both do it slowly, and the fistee needs to do that stretching work they first had to do to get the hand in.
For some people, just having a hand inside is plenty of stimulation, and no movement is required. When the fister moves their hand, do it slowly, and don’t go for f***ing motions. Expand and contract the fist slowly; turn left or right gently; or try a subtle in-and-out motion. Once again, communicate with each other. Together, you’ll figure out what feels the best and what is a no-no.
“Eating out” during sex with women, transmasc and AFAB folks
Receiving cunnilingus [tips, no explicit photos], the clinical name for eating p***y, is the favourite sex act of a lot of people. It’s a classic of having sex with women and with transmasc or AFAB partners, who may often like it better than penetration. Many people are uncomfortable with their own vulva, however. The thought of a partner getting up, close, and personal with it—with their face, nose, and mouth at that—can be intimidating.
So as always, ask your partner how comfortable they are with you going down on them, and what you can do to help them feel more comfortable. Being considerate as well as excited at the prospect of eating out your partner can go a long way towards that. Make it obvious that you have the tastiest and most beautiful treat ever in your mouth, and that you’d do anything with it to make them feel good. Enthusiasm can take you a long way in itself.
Still, some people dislike receiving oral sex, just like some people dislike giving it—and that’s okay. A long-term sexual relationship will be under a strain though when it’s between someone who loves receiving oral sex and someone who dislikes giving it. Still, you’re both hopefully on the same page in that regard.
Explore what your partner likes
To begin, talk with your partner about what they like, and what to avoid. Then position yourself comfortably. Many women and transmasc or AFAB folks take a while to orgasm – sometimes 20 minutes or more. Having to reposition yourself at the moment your partner is getting close might cause some frustration. Don’t go straight for the glans – it’s super-sensitive. You’ll have to work your way there, and sometimes stimulating the head directly will never be an option.
The entire p***y is wired for pleasure. So start by exploring, and pay attention to what triggers a happy reaction. Your partner should let you know too whether you’re getting hot or cold. Each person is different, and what worked with a previous partner might not work with the person you’re with right now. Here are things you can try. Run your tongue all over slowly, either with the full tongue or just with the tip. Kiss and brush your lips against various spots. Don’t hesitate to suck on something, but don’t start too hard. Try using your nose or your chin—watch out for the stubble, although some people love that—if you want.
When you get to the head of the clit
Make your way to the hood of the clit, and explore that space. Tongue the hood and the area around it. Suck on the hood and indirectly, on the glans below. When your partner gets really turned on, you might even be able to feel the clit’s shaft below the surface, either by sucking or by rubbing the area with your fingers. Some people say that treating that area like you’re giving a blowjob works well for them. But start gently at first, and work your way up to stronger stimulation.
With a partner who enjoys getting fingered, get a couple of your digits in their front hole. Push on the internal clit doing that “come hither” motion I’ve mentioned before. Licking the front hole’s entrance or pushing your tongue in is also a possibility. If your partner is down for it, you can try teasing their glans directly or even sucking on it, but start gently and don’t overdo it, unless your partner is going nuts in a good way.
So explore, communicate well with your partner, and pay attention to their reactions – even to small changes in your touch. You might end up discovering a stroke that really gets them going. When that happens, stick to it – motion, pace, pressure, and all. There’s no guarantee your partner will orgasm from what you’re doing – and that’s okay. It takes very consistent stimulation to get there for many people. Still, with a bit of patience and an eagerness to pleasure and try things, you’ll learn what your partner loves when you give them head.
Cunnilingus, HIV and STIs
There’s safer sex stuff to consider when you give or receive cunnilingus. The risk of getting HIV from eating p***y is negligible. It is theoretically higher when there’s menstrual blood, though, so be careful especially when you have a cut or sore in your mouth. Still, other STIs spread that way though, either from the giver to the receiver or vice versa. STIs that pass on through skin contact in particular, like herpes—a person is sometimes contagious even when there are no noticeable sores—and HPV are a risk if one of you is infected.
You can protect each other’s health using a dental dam, which can be homemade [how-to, images of condoms]. Putting some lube on the side that’ll touch the vulva will improve the experience. The texture of the dam can be an interesting sensation to play with, especially when either one of you has a latex kink. But most people eat p***y without a barrier, and nothing dramatic happens to them. It’s good form to ask a partner if they prefer using a dam, though. Get tested for STIs every six months when your sexual practices include unprotected oral sex.
So this ends part 3. The final part of Sex with women, transmasc and AFAB people will be all about f***ing and PiV – something a lot of people care about.
