THIS ENTRY WAS POSTED ON December 12, 2023 BY Jamie Joy.
Why is anal enjoyable and for who?
Before we dive in deep, let’s consider why you or your partner(s) want to engage in anal. Some people want the sensation of being fucked. Others enjoy the feeling of being full. For many, it is about the intimacy of the interaction. Anal play can range anywhere from sweet and sensual to rough and dirty, which might mean different positions or techniques.
No matter your gender or body parts, anal play is a form of sex that can truly be enjoyed by all. Lola Jean defines pegging as an activity where one person is using a strap-on or dildo to penetrate another person in the ass. Anyone can wear a strap-on and all bodies can receive anal pleasure.
For people with penises, when the prostate is stimulated, it becomes engorged and can feel really good. For people with vulvas, when there is something inside the ass, it can change the shape of the vagina, causing sensations to feel different. There are so many wonderful reasons to explore anal play with your partner(s) or even yourself!
Preparation & Peace of Mind
It is common for people to avoid putting anything in their butt due to a lack of knowledge and understanding. Let’s overcome our fears so we can tap into the abundant pleasure of anal play and traverse this new terrain with confidence. Lola Jean identifies the most prevalent fears as the two P’s: Pain & Poop. Fortunately, both of these fears can be mitigated and do not need to happen with the right preparation and planning.
If you are afraid of poop, it is important to remember that sex is messy. Since mess is often a part of having sex, we can accept that poop might happen. However, if the sight or smell of poop is going to be an issue, there are ways to clean out.
It is not a requirement to do an enema before engaging in anal play. But if it makes you feel more comfortable, then do it! There are many different brands and types of enemas so check out your options here:
 |  b-Vibe Enema Bulb |  |
Important note: You do not need to change your diet a week leading up to anal play or douche multiple times beforehand. Cleaning out once before going into your butt is usually enough.
As the receiver starts to do more butt stuff, they will get to know their body better and will be able to tell if it is a good day for anal or not.
Another method that can help mitigate poop and mess is using barriers! Lola Jean recommends using barriers on as many things as you can, especially your toys. Not only does putting condoms on toys help with cleaning the toys afterwards, but also helps prevent the spread of STIs.
Laying down puppy pads, sex blankets, or towels can also help keep your anal play cleaner while providing peace of mind so there is less to worry about and more time to enjoy yourself.
Lastly, Lola Jean insists that gloves are an absolute must. Gloves are super beneficial for avoiding getting lube or mess in places you do not want - for example if you want to put your hands in your partner’s hair during sex. If you are stimulating someone with a vulva, switching out gloves can ensure that you are not cross contaminating between holes. Try using different colored gloves for different holes if that helps!
 Liberator Fascinator Throw |  Skyn Original Condoms |  Satin Dental Dams |
All of these options from enemas to barriers are meant to relax your mind so you can relax that sphincter in preparation for what’s to come next.
Lube, Lube, and more Lube!
Oftentimes when people talk about doing anal, the advice is “lube up and start slow” but there is so much more to know than that. Lubing up is just one step amongst many! So let’s talk about lube. Lube is a key aspect of making anal comfortable and knowing the type of lube to use is essential to having a good time.
Lola Jean recommends using a thick water-based lube without any glycerin. We want the thickest so that it can last longer. Water-based lubes do absorb into the rectum quicker, but are safe with silicone toys. If you are using glass or metal/steel toys, you can opt for a silicone-based lube instead. Silicone lube lasts longer because it does not absorb into the skin, which is great for anal.
Lola Jean’s favorite water-based lube for anal is Sutil Rich.
When in doubt, use more lube and continue to reapply as you go! There is nothing wrong with using too much lube, but there is a problem with not using enough.
 Sutil Rich Water-Based Lube |  Swiss Navy Silicone Lube |  Naked Silk Hybrid Lube |
Finding the Right Toy for You
One part of preparing for anal play is gathering the toys that you plan to use. In this next section, we will explore different products from harnesses to dildos to plugs. Let’s jump in!
There are a lot of different harnesses out there. Lola Jean advises you to find what is comfortable for you. Comfort over appearance! Since our weight fluctuates or what we wear changes, a harness that is adjustable is best. She recommends the Joque by SpareParts.
There are a lot of additions that can make the experience more pleasurable for the person wearing the harness such as a BumpHer that fits onto the base of the dildo and can be grinded on or adding a bullet vibrator into the pockets inside the harness.
 Lippi Silicone Base |  Shagger Silicone Base |
When it comes to placement, the mistake that most people make is that they put the dildo directly over their genitals. Lola Jean recommends wearing the strap-on higher for comfort and to increase range of motion.
Moving onto insertables! The first and most important rule for putting stuff in the butt is to ensure that there is a flared base. Without that crucial aspect, the toy can easily get sucked into the ass, which could lead to an embarrassing visit to the emergency room.
Often when people are picking out a dildo for anal, they look for something short in length. But in reality, more length on the toy going into the butt can be better so that there is the option to go in deeper. Having more length on your dildo can also help make more positions possible. The receiver is going to feel more of the width over the depth.
So what makes a dildo ideal for anal is medium length, smaller girth, with a curved head to stimulate all of the fun spots. Lola Jean’s favorite dildo for pegging is the Tantus Sport.
Dildos with texture that are ribbed or uniquely shaped can give the sphincter something to grab onto, which can add more sensations. Check out this dildo-plug combo for example.
Lastly, we will briefly discuss butt plugs. Plugs can be great for anal training, though that is not necessary to do before anal penetration. The sensation of a plug inside the ass is very different from a hand or a dildo. There are plugs designed specifically for prostate pleasure and others designed for rimming sensations.
Lola Jean enjoys using butt plugs because they help bring attention to the sphincter so the receiver can focus on that part of the body. This can be a great exercise in getting comfortable with the feeling of having something inside the butt.
We could go on and on about anal toys - there are truly so many different styles and options. Once you have acquired the supplies you need, you are ready to get into the action!
 Tantus Sport Dildo |  Dildo Plug Balls |  b-Vibe Rimming Plug Petite |
Starting Slow: Anal Massage & Hand Stuff
Lola Jean believes that all good anal play starts with an anal massage. An anal massage is specifically external with no penetration. Start with generously applying lube to your gloved hand and then ball your hand into a fist. Aim between the cheeks over the area of the anal opening and move the fist in a figure eight motion. Apply pressure as desired and use your knuckles to find out what feels good. This method will help relax the sphincter and warm up the receiver for more.
In general, using your hands is more tactile and can help you feel what you are stimulating whereas you cannot do the same with an apparatus. With your fingers, you can feel what’s going on inside and get a lot more information in order to find the exact spot inside your person.
When it is time for entry, start with small circles over the opening so that the hole can start to relax with the very tip of the finger nudging on the outside. A great position to start for the receiver is laying on their back with their legs up in the air also known as the happy baby. In this position, the pelvic canal shortens, making it easier for the giver to hit those sweet spots.
Important note: No matter what genitals the receiver has, the fingers should enter facing towards the belly button.
Lola Jean asks her bottom to breathe in sync with her to start. Breathing helps with initial insertion. On the inhale, the pelvic floor contracts and on the exhale, the pelvic floor elongates, which allows the anus to open and be more receptive. On the exhale, slowly push the first finger inside. At first, this might feel weird for the receiver to have something foreign inside their butt. Lola Jean advises waiting at this point before moving the finger around so that the person can adjust.
Once the person feels ready, press the one finger upwards searching around for the spot by moving the wrist. For people with penises, the spot will feel slightly firmer than the rest of the tissue. With prostate pleasure, you can add pressure, tap your finger, or move from side to side. Ask the receiver how it feels and get feedback as you go!
With just one finger inserted, the rest of the fingers are curled up on the outside and adding pressure for added stimulation. If the receiver wants the feeling of being fucked, you can lightly punch the external area around the hole to mimic that feeling.
Doing some handiwork before dildo penetration can engorge those special spots and make it easier to hit them once you move into strap-on fucking. Understanding where the spot is will determine which dildo you want to use based on the depth of the spots.
And finally…Penetration & Pegging Positions!
Now that we have gotten past insertion, let’s get into different positions and techniques for strap-on sex and pegging. First thing to consider is height differentials. If there is a large height difference, utilize positions, furniture, and pillows to support both the giver and receiver in feeling comfortable.
Lola Jean’s favorite position for beginners is the receiver on top. The giver can lay back and the bottom can be in control of putting the dildo inside their butt at a pace that works best for their body. Moving the hips side to side and back and forth can help the receiver find their own spots. For the giver, they can penetrate from the bottom by simply engaging in pelvic thrusting, which is a lot easier than using quads or being on their knees. The giver can hold the person on top while bracing their feet into the ground for leverage.
Her second favorite position is the giver planking on top of the receiver. For this position, she recommends starting in doggy. When you are flipping over, remember that the dildo should be facing towards the belly button and needs to be turned upside down.
From doggy, both partners will work as a team to extend their legs at the same time to lay flat. It is important to move slowly to avoid the dildo popping out. This position is really nice for a lot of body to body contact. From the planking position, the giver can simply grind their hips or do up and down movements for a fucking sensation. This position can lead to deeper penetration so if that is not desired, try switching out the toy for something smaller.
Lola Jean is a fan of working smarter, not harder when it comes to choosing positions so that the giver does not burn out. Having different types of elevation will assist with hiking up the hips, changing the angle of the pelvic floor, and relieving the work on the one penetrating.
For the receiver, changing the position of their pelvic floor and focusing on breathing exercises will activate either the prostate or clitoris depending on the body. The pelvic floor is shaped like a bowl and controls 3 things: urination, defecation, and orgasm. One of the benefits of the pelvic floor is that we can engage it hands free. When we have better control of our pelvic floor muscles, we don’t have to necessarily worry about the amount of pressure being applied on it because the stimulation can happen internally. The more regularly you practice engaging your pelvic floor muscles, the stronger they will be, and the better your orgasms will feel!
Now go get some ASS!
So let’s summarize everything we have learned from our Anal for Anyone workshop:
Always use barriers, put condoms on all of your toys, wear gloves, re-apply lubrication, use the thickest lube possible, make sure your harness is comfortable and in the correct location, always start with anal massage, then start with your hands, figure out your person’s spot, have them figure out their spot, start dildo penetration with good entry level positions, have the person receiving on top, explore what feels good by moving your hips in all directions, discuss with your person why they like this and what they want from anal.
Ultimately, sex is about feelings over activities. Whatever you want to feel from anal play, you can achieve with imagination and creativity.
Lola Jean believes that, “world peace is going to happen through people’s butt holes,” so now go forth and make this world a better place, one booty at a time!
If you want to learn more, check out some of our books on anal pleasure:
 The Pegging Book |  Anal Pleasure and Health |  Ultimate Guide to Prostate Pleasure |
And if you want to stay in touch with Lola Jean, you can follow her on Instagram at @lolajeandotcom.
Jamie Joy (they/them) is a queer trans Jewish sex educator and hungry slut for freaky fantasies and kinky perversions. Their life and work is committed to spreading joy, pleasure, and consent through community organizing. As a triple fire sign Sagittarius, Jamie Joy is passionate about dancing while eating, playing sadistically with flaming floggers, and teaching people about the wonders of anal fisting. They are always excited to connect with new friends; you can find them on Instagram @badjewboy or email them at jamiejoyeducation@gmail.com.