By Kenneth Play
The Ultimate Guide to Getting Your Girlfriend to Love Anal Sex
So you wanna do butt stuff?
You’ve come to the right place!
Here’s what most guys don’t get about anal sex: It can be really pleasurable for her. Even orgasmically pleasurable. But if she hasn’t experienced much pleasure from her booty yet, she’s probably gonna be reluctant.
The thing is, if anal is a sacrifice on her part, it might not feel good at all. It might even hurt. (It shouldn’t hurt!) You might get some pity anal on your birthday, but she won’t be doing it for pleasure. That’s not really what you want, is it?
My guess is, if you’re into anal sex, you don’t want to beg for it and maybe enjoy it once a year. You want to make it so mutually pleasurable that she begs you to enter through the back door… often.
FAQ:
Does anal sex hurt?
It shouldn't! The key is to go slow, use plenty of lube, and communicate with your partner. Make sure she’s fully aroused and comfortable. Take things at her pace and always prioritize her pleasure.
How can I make anal sex enjoyable for my girlfriend?
Earn her trust by creating a pressure-free environment and focusing on her pleasure. Start slowly with fingers or toys, explore her boundaries, and communicate openly. Begin with gentle touches, one finger, and plenty of lube. Let her lead the pace. You can incorporate familiar pleasures like clitoral stimulation to make her more comfortable and turned on.
Is anal sex messy?
It can be a bit messy, but a little prep goes a long way. Simple steps like using a dark towel and/or a puppy pad, showering before and after, and having wipes handy can help manage any mess. Be cool about it—poop happens, but don’t make it a big deal.
How do I keep anal sex hygienic?
Make sure to avoid cross-contamination by keeping anal and vaginal play separate. Use condoms for anal sex and wash up before switching between areas. Clean hands and gloves are essential.
Do we need to use lube?
Absolutely! The anus doesn’t produce its own lubrication, so using a high-quality lube is essential to avoid discomfort and protect delicate tissues.
Can anal sex lead to orgasm?
Yes, it can! Many people find anal stimulation, when done right, to be incredibly pleasurable, and it can even lead to orgasm. Finding the right angle and using proper technique are key.
How should I pull out after anal sex?
Ask your partner to push out as you slowly pull back, making the transition smoother.
What’s the 45-degree angle rule?
This technique involves angling your fingers or cock upward towards the belly button at about a 45-degree angle during penetration, which can help you hit the right spots inside her. It’s such a useful sex hack, I have a whole article on it!
What is aftercare, and why is it important?
Aftercare is about making your partner feel safe and cared for post-anal sex. Whether it’s cuddling, talking about the experience, or giving her space, aftercare is crucial for emotional and physical comfort.
Earn Her Anal Trust
The three biggest concerns people have about anal play are: Will it hurt? Is it gonna be gross? I don’t want to be pressured into it. If you have a strategy to handle the big three, then you’re halfway to earning her anal trust.
Begin with discussing boundaries, desires, and concerns. The concerns you both bring to the table will set the stage for your prepping.
First, and perhaps most important, she needs to know that you’re only going to do something if it feels good to her. If at any time, for any reason, she decides that anal is just not for her, assure her that you can take anal off the menu altogether, with no consequences. This pressure-free environment truly relaxes the anal sphincter!
Second, the concern about poop is real. (We’ll go over this in more depth in the Anal Hygiene section.) It’s a good idea to put down a puppy pad or a dark towel, and to shower before and immediately after.
Third, if she’s worried that it will hurt, let your partner know, “I want this to be pain-free and pleasurable for you,” so you’re going to take it slow, and go at her pace, and she can pause or stop the experience at any time, for any reason. And then make sure she knows how crucial her pleasure is to you, and how much you want to find the spot that feels absolutely amazing to her.
PRO TIP:
Here’s a best practice for the first time exploring anal sex with a partner. Demonstrate your willingness to go slowly and only do things that cater to her pleasure. Have a playdate session where you begin exploring anal play with just one finger, and you don’t put your cock in her ass for the entire experience. This is a type of long game, but honestly, it probably won’t be that long, because if you show her how pleasurable anal exploration can be, without any pressure, she’ll almost certainly want you to fuck her ass the next time!
Anal Hygiene
The most obvious risk is that the ass is literally sometimes full of shit. As a result, it houses specific bacteria that are safe and healthy in the ass, but which can cause infection if they’re spread to other areas of the body. Poop is not the problem. Cross contamination is.
Of course, shit happens—literally. Porn often sets people up with an expectation that assholes are clean and smell like flowers. But porn stars often have enemas or colonics in addition to fasting the day before and the day of a shoot, so there is no chance of poop being in their colon in that moment.
Since most people don’t go to these lengths in real life, it’s important to be realistic: this is where poop comes out, and if you want to engage in anal sex, you have to develop a relationship with mess. Don’t shame your partner if your fingers or your cock come out with a little poop on them. Have a plan to handle it.
You can keep puppy pads, towels, gloves, condoms, and lube nearby, as well as a basket in which to throw anything that gets dirty. If shit happens, just clean it up. Deal with it like you don’t give a shit.
If I can tell my partner is embarrassed, I’ll often respond with a gentle joke like, “Would it make you feel better if I poop on myself?” Usually, my partner laughs and we go take a shower.
In short, if you don’t want to deal with shit at all, don’t do anal.
There are some things you can do to mitigate the shit though. You might consider timing anal sex for after she’s had a bowel movement. She could douche, do an enema, or just wash her anus with soap and water beforehand. She could also use a bidet.
Put a puppy pad and a dark towel down on the bed to make any messes easy to clean up. Have baby wipes at the ready.
If you want your ass to be porn-star clean, you can download this excellent guide by Blindjaw.
No matter what you do to prep, make sure you don’t cross-contaminate in the heat of the moment. Keep track of your hands. If you are going to switch from vaginal to anal stimulation, or vice versa, you might want to have one hand gloved and the other ungloved – this is a simple way to keep track of your hands. Then make sure you use the gloved hand for her butt and the ungloved one for her pussy. Or wear gloves for anal play and then remove them when you switch to playing with her pussy.
The bottom line is: You DO NOT want to bring any bacteria from her butt into her pussy. (Don’t go from eating her ass to eating her pussy either – trust me, it’s not a good idea.)
A Word on Lube
Lube is required! Another risk in anal sex is that while the vagina and the mouth create their own lubrication, the anus doesn’t. You need lube, not just to help toys and fingers and your cock slide more easily into your partner’s ass, but to protect those delicate tissues from tearing.
Stretching for Anal
The warm-up is everything!
Let’s get a little nerdy about butt anatomy for a second. Butts have two sphincters that act as gates to the rectum. One is external, and it’s possible to control it voluntarily when you clench or relax your anus, which is a helpful feature that keeps you from pooping unexpectedly. The second sphincter is internal, and its action is involuntary.1Kenneth Play, Beyond Satisfied: A Sex Hacker’s Guide to Endless Orgasms, Mind-Blowing Connection, and Lasting Confidence (Scribe Media, 2022). https://kennethplay.com/book/
The second sphincter is controlled by the autonomic nervous system, the same thing that controls your heartbeat, breathing, and digestion. You can control your heart rate and breathing voluntarily by learning to relax and calm yourself, but not directly like you would your arm or leg muscle. Similarly, you can’t force yourself to be sleepy. In order to sleep, you have to learn to relax in a dark, cold room, and your body naturally drifts off.
The same is true of the action of this second sphincter—the only way to control it is through indirectly relaxing it. These gates are right next to each other, one after the other. Don’t pry open either sphincter with too much force, or you can damage the tissues.
Here’s a secret about butt stuff: anal sphincters are tighter than vaginal muscles, but only at the opening. Past the sphincters, it’s actually roomier inside a butt than inside a vagina. PNF stretching deactivates the sphincter.
With gloves on, lubricate your hand and use your fingers to massage your partner’s anus around the opening. Let her get used to the sensation of your fingers and encourage her to finger her own clit while you stroke her anus.
If she’s feeling uncomfortable, it might help for her to put her own fingers in her ass while you play with her clit, and then swap. Wear gloves for anal play, so you can remove them when switching to the vulva and clit. Sometimes intense sensations can be more enjoyable when we feel in control of them and are aware of what’s going on.
PRO TIP:
Here’s a great hack for anal insertion used by doctors for medical purposes. When your partner wants you to insert a finger, ask her to try to gently push your finger out as you smoothly slide your finger in. While this hack may seem counterintuitive at first glance, think about what happens to the muscles of the anus when you’re pooping. As you push out, the muscles relax and open wider.
Always start with one finger only. Get plenty of lube on that finger. You might encourage her to stroke her clit. As she pleasures herself, let the pad of one gloved finger rest over the opening of her anus. Breathe, wait, and feel for her anus to pucker slightly as it relaxes. That’s how you know your partner’s body might be ready for insertion. That little pucker is the first gate opening.
If you’re more of a visual learner, I go over this stretching technique extensively in my Beyond Satisfied Pro course, so you can see anal PNF in action in real-time on my demo model.
PRO TIP:
In my past life as a personal trainer, I utilized PNF stretching technique with my clients (proprioceptive neuromuscular facilitation). This type of stretching was designed to relax muscle and increase tone or activity. As it turns out, butt stuff can benefit from PNF too! I love this technique because it helps your partner develop the distinction between a clenched and relaxed anus, while increasing flexibility.
Imagine you’re trying to stretch her anus in four directions – 3 o’clock, 6 o’clock, 9 o’clock, and 12 o’clock.
Insert your finger one knuckle deep and bend at the knuckle to create a hook. Ask your partner to tighten her asshole and squeeze your finger, while you gently stretch towards the 3 o’clock position. Have her squeeze for five to seven seconds or until she gets tired of holding the tension, and then ask her to relax. When she releases, you’ll maintain the same amount of tension towards that 3 o’clock position, and you’ll notice that the anus is able to stretch more.
This is also a Jedi mind trick, because most people don’t know how to relax their assholes! But if you squeeze it until you get tired, the asshold naturally relaxes. Repeat this for the rest of the three quadrants.
After you’ve stretched all four quadrants, she will have a heightened awareness and gain some voluntary control over her anus. Encourage her to take a breath and push your finger out again, then insert a finger fully.
With your finger fully inside, take time to feel the different textures of your partner’s anus and the gentle S-curve shape of her anus. You can flex your finger up to massage her P-spot and G-spot. Don’t slide your finger in and out; just flex up towards her G-spot. Calibrate to find the level of pressure that feels good to your partner.
What’s the P-spot? Check out my Advanced Fingering Techniques article for a run-down on the A-spot, P-spot, G-spot, and cervix as well as a finger stacking technique for easy entry when inserting more than one finger. (It’s one of my favorite sex hacks!) Most of the fingering techniques will work here – the only difference is that your finger is in her ass rather than her pussy.
As your partner relaxes, you’ll feel her anus relax, too. Continue to lube up your finger periodically. You don’t have to pull your finger out completely to lube up – pull out until you are only one knuckle deep, apply lube to the rest of the finger, and then slide it back in. After your partner gets used to the sensation of your finger in her anus, you can try other kinds of stimulation. Your partner might like more friction from moving your finger in and out, or she might like the sensation of twisting your finger back and forth.
PRO TIP:
Generally, anything inserted in the butt—whether fingers, a toy, or a penis— feels better when angled upward towards the belly button at a 45-ish-degree angle. It’s such a great sex hack that I wrote a whole article on it: The 45-Degree Angle Rule for Anal. (It also covers two S-tier anal fingering techniques.)
Level up your pull-out game! When your partner is ready for you to pull your finger out, ask her to push your finger out as you slide it out. Just like inserting your finger, when your partner bears down the muscles relax and open up, making it easier to slide your finger out.
It’s All About the Turn-On
Receiving anal sex without being turned on is like getting a prostate exam, without lubrication. Yeah, sure, a finger can fit, but unless you’re into medical play, it’s probably not gonna feel great.
Similarly, even if their rectum can fit a cock, anal sex is no good unless your partner is really turned on. The secret sauce to all good sex is arousal. Since she needs to be really turned on, that means psychological arousal is crucial.
A rim job is an excellent way to warm your partner up to anal touch because it prepares her psychologically for anal play. If you show you’re willing to lick her anus and put your face on it, she can relax knowing you’re comfortable playing down there.
Beyond warming your partner up, you want to help her create positive associations, both with sensation on her anus and with how she feels about the experience emotionally. The ass is a vulnerable body part for most people, so show your love and admiration for your partner’s butt. I have literally said, “You have such an elegant butthole.” Sometimes they chuckle and sometimes they go “aww.” Either way, it’s a fun way to flirt and it diffuses tension.
PRO TIP:
If your partner is a newbie to anal stimulation, don’t start with it straightaway. Begin with the stimulation that most reliably gets her off. (For example, rubbing her clit.) Arousal brings her pleasure centers online, and the brain is a pattern-making machine. Use her favorite stimulation to get her close to the edge, and then add in the new stimulation. You’ll be helping her create pleasurable associations between her butt and sex.
For instance, if clit stimulation is the star player on the team, the one that scores every time, anal might be a rookie player. So you want to begin the game with your star player, take the ball all the way down the court, and then pass the ball to your rookie, anal, to score.
This way, your anal rookie gains some confidence, by scoring the game-winning goal! (And the crowd goes wild.)
Edging
You know how when you’re about to cum, the stimulation feels amazing? We’re going to leverage this phenomenon.
Edging is a sex technique in which you get very close to cumming but don’t cum yet. Instead, you lower the intensity of the stimulation so that you can ramp it back up again. By bringing her close to orgasm and then pulling back, you’ve increased the blood flow to the area, engorging her genitals.
You’re essentially revving her arousal engine and priming her body for more pleasure.
PRO TIP:
If your partner isn’t ready to try having your cock in her ass, invest in toys. You can get anal training kits with different-sized butt plugs from small to large. Always make sure to buy toys with flared bases for anal play, to make sure you don’t accidentally get a toy stuck in the anus. Your partner can wear a butt plug in her anus during vaginal sex to get used to the sensation. Silicone lube can’t be used with silicone toys, so be sure to buy the appropriate lube. Consider buying a dildo that’s the size of your cock and give it to your partner to masturbate and practice with on her own. When she’s able to fit the toy cock in her butt, she’ll be able to look at your cock and think, Game on.
Enter Through the Back Door
When you and your partner are ready to have penetrative anal sex, be sure to warm her up just as thoroughly as you did for the exploratory exercises. She may not need you to help stretch the tissues, but she’ll benefit from stimulating her clit with her hand or a vibrator while you finger her anus and get her aroused and more familiar with anal sensations.
Wearing a condom is helpful for reducing cross-contamination, and the chance of either of you getting a UTI. Be sure to lube up your cock and condom from the head all the way down the shaft. Silicone lube lasts longer for anal sex, and it provides a slicker, smoother sensation.
Position your partner lying on her side with her bottom leg straight and her top leg bent at the knee. This makes for an easy, straight line to enter her anus, and it also ensures that when you lube up, the lube doesn’t drip down to cross-contaminate your partner’s vulva.
Don’t do anal in the dark. Be sure you can clearly see your partner’s anus so you can confidently slide your cock in. You also want to make sure you’re fully aroused and hard; it won’t be as comfortable to try to put your penis in your partner’s anus if it’s soft.
Hold the head of your cock and align the angle so your pee hole is in a straight line with your partner’s anus. This is like threading the eye of a needle—alignment matters. You don’t want to angle your cock up or down as that will likely be uncomfortable for your partner. Ask your partner to push out as you slowly slide in, and check with her to see if it feels comfortable. Don’t fuck vigorously right away; stay still as your partner pleasures her clit and gets used to the sensation of your cock inside her.
When your partner is ready for you to add a bit of movement, keep your cock straight and gently move in and out. Lube up your cock by dripping lube on the shaft as you pull your cock out, and then you can seamlessly slide your cock back in. (Porn stars use a lube shooter to squirt lube into the anus to make lubing up easier.) Have a wet wipe handy for lube overflow. And this is important: Wipe toward her anus! Make sure the lube doesn’t drip down from your partner’s anus to her vulva—this is a particular consideration when you’re fucking her ass doggy style.
If you’re switching back and forth between anal and vaginal sex, wash your cock and pelvis with soap and water in between. If you are fluid-bonded with your partner (i.e. you agree to do it raw), you can make the transition faster by wearing a condom for anal sex, and take off the condom when you want to go back to vaginal sex. Wipe your pubic bone down with a baby wipe before pressing yourself up against your partner’s vulva.
Double Penetration
Another reason to gift your partner a dildo to masturbate with is that you can use it for double penetration. She can insert the dildo inside her vagina while you fuck her butt, and you can both experience a new range of sensations.
You can also hold the dildo against your pelvis while you fuck her with your dick, turning you into an anime tentacle porn fantasy with multiple penises.
I love the feeling of double penetration, because the toy creates more pressure against my partner’s anus. Many people like the “full” feeling that comes from having a toy and a cock in them at the same time.
PRO TIP:
Did you know there is such a thing as a vaginal plug? It’s a fun toy to use during anal penetration because it increases internal pressure and intensifies the sensation for both of you.
Pulling Out
The head of the cock is usually the biggest part, so getting it in and out of the external sphincter is usually the most intense part for women. Communication around pulling out matters. In the same way that you checked in with your partner to see how far to advance, check in with her again when you’re ready to pull out. Ask if she’s ready, and if she is, tell her to push you out with her muscles as you pull back. If you notice a little poop on the condom, handle it right away. Use baby wipes to clean your partner (and yourself off), making sure to wipe from pussy to anus, not the other way around. Take off the condom, and wash your hands and your cock with soapy water.
Don’t stay in bed after anal sex; get up and shower. Offer to shower together or give your partner space to shower or use the bathroom alone. If your bathroom is close to your bedroom, go into the other room, tell her you’re going to get her some water and make her a snack, and give her some space to clean up or use the toilet alone. Tell her to meet you in the kitchen afterwards. Sometimes anal will make her have to poop or fart and she might want some private time. Both partners should pee after sex to lessen the chance of getting a urinary tract infection.
Give her some private time if she’d like, but don’t forget aftercare! This is a great time to snuggle up and thank her for trusting you with her ass. You can debrief, and discuss what was really hot about the experience and what you would like to adjust the next time you try it.
Make Her Go “AHA!”
To conclude: Your cock in her ass will be much more welcome if you can show her the potential for pleasure and orgasm.
Aim to give her 3 aha moments:
- Aha! Rear entry doesn’t have to be painful.
- Aha! When you find the right angle and you’re stimulating the right spot then anal penetration feels good (ringing the doorbell) &
- Aha! Ringing that doorbell can lead to an orgasm.
Also, squirting orgasms via anal are totally possible – since you’re stimulating the same erogenous zones, through the back door. Learn the advanced technique I call “Release the Kraken!” here.
To review: When introducing a partner to anal, begin with familiar pleasures. Once she is fully aroused, explore her butt to find the most pleasurable spot with your fingers or a toy, and then stimulate that spot while you give her the sensations that reliably bring her to orgasm. When she is close to cumming, you can continue with both types of stimulation to bring her all the way across the finish line, or you can ease off of the star player and continue with the rookie all the way through orgasm, so that her brain makes the association between anal and cumming really hard.
If you master this, Sex Hacker, she’ll be asking you for anal… and not just on her birthday.
Sources
is an internationally-recognized sexpert focused on female pleasure, sexual performance, & rapid skill acquisition. Named the “World’s Greatest Sex Hacker” by GQ, his pleasure technique videos have been viewed over 16M times. He is the Author of "Beyond Satisfied," and his uncensored video course, designed to teach men how to please women, is endorsed by sex educators, therapists, and women worldwide.
