THIS ENTRY WAS POSTED ON August 8, 2022 BY Kassandra.
Are you a booty beginner trying to master the basics? Here, NY Pleasure Chest Supervisor & Sex Educator Kassandra breaks down anal 101, from anatomy and toys to tips and tricks to ease your way into your anal odyssey!
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Bottoms Up: Butt Stuff 101
Anal play is something that many of us have at least dabbled with. Some of us have lightly prodded at our anuses while masturbating. Others have had a partner stick a thumb up our butts during intercourse. Regardless of what has you interested in penetrative anal sex, one thing is true for many of us.
Anal pleasure is real; anal stimulation feels good. And it makes sense that it would! Our anus participates with our genitals in the process of arousal, and the delicate anal tissue has a whole bunch of sensitive nerve endings that make stimulation enjoyable.
But many of us are stuck on how to begin our anal journey. I know some of you anal beginners out there are tempted to take a whole dick, dildo, or sex toy up your ass on the first go around. There are a few things that the anal virgin should know before taking such a plunge.
You may be a little disappointed to find that it takes time and patience to be able to take something big and phallic up your butt. But, the best part of getting to the top of the mountain is the journey, right?!
Let us discuss some things you should know about anal penetration before jumping into the deep end. I’ll try to keep it cute for y’all. We’ll start with talking about anal anatomy basics, then get into some things you can do to ease your anal muscles into the sex act.
Finally, we’ll talk about starter sex toys and find something that’s right for you :)
Anal Sex 101: Anatomy before Anal Play
While our anuses are accustomed to stretching and having things travel through them things get a little more complicated when your sexual acts result in putting stuff up your butt instead of pushing things out. Many of us don't know a thing about what is happening back there.
For instance, did you know that all of us have two anal sphincter muscles?
The outer sphincter muscle is the one we are better acquainted with. This sphincter is voluntary. The second inn er sphincter muscle is an inch or two inside of the anus and is involuntary. Beyond that is the rectum, which is about 6-8 inches long. This leads to our colon, where fecal matter is stored until it’s ready to be expelled.
If you have a prostate gland, it will be pretty much in the same area as the G-spot (sometimes stimulated during vaginal sex). The prostate is an organ that creates seminal fluid and is a firm mass about the size of a walnut. You can find it by entering your finger about two or three inches into the anus with your palm faced upwards.
Then, angle it towards the front of the body and feel around. The prostate responds well to the same kinds of stimulation as the G-spot (we are more alike than we are different). When you locate it, try doing some come hither motions, tapping, and simply applying pressure to it.
For those who do not have a prostate, the sexual act of anal play can still be super fun! The anus is rich in nerve endings and, since the wall in between the vaginal canal and the anal canal is so thin, it is possible to hit the G-spot with anal penetration. For a real treat, try playing with your ass and your external anatomy at the same time.
Anal Sex 101: Getting Started with Butt Play
Okay, so you have a basic understanding of your anatomy, and now you are ready to get the anal pleasure show on the road. I know some of you are still looking over at your favorite dildo. I implore you to chill on the sex toy fixation. We will get there with some anal sex training (and a sh!t ton of lube).
I suggest starting with your fingers. You probably won’t run into any poop unless you have to go right now. Remember, the colon is where poop is stored and it's released during a bowel movement. One would have to have fingers that extend up to 8 inches long to get to any backed-up feces. If you are still feeling nervous about potentially touching poo, throw some latex or nitrile gloves on.
Now that you are ready to start, I want you to go slower than slow. I would start with a familiar pleasure to kick start the arousal process. Arousal makes penetration easier and more pleasurable if that's your goal. There is no rush for that, though. Take your time here. No two anuses are exactly alike. Get to know yours with some external anal massage.
Start on the outer part with lots of lube (I recommend Sutil Rich or Sliquid Silk. More about this later!). Pay attention to your body and how it reacts to different types of touch. Try gently circling your butthole or doing light stroking motions. Breathe.
A good trick to remember is to exhale for longer than you inhale. With deep breaths, try bearing down with your pelvic floor muscles. This can help you inch a little deeper into your anal region. When you get further inside, stay there for a while and explore.
When you’re about two knuckles deep, see if you can feel your two sphincters contracting. This is totally normal. Remember to maintain a relaxed pace, keep deep breathing, and focus on what feels good. Experimenting with anal pleasure is fun to do alone, but also great to do with a partner! Don't be afraid to ask for a hand <3.
When you’ve gotten used to one finger, experiment with light in and out thrusting at your own pace. Try moving your finger in a circular motion. You can go on for as long as you want. You don’t even have to penetrate the anus! You can gently massage for more pleasure. Pleasure is the goal here. So, again, stick with what feels good.
Pain is a sign to pause and either slow down or take a step back. Don't expect anal orgasms on your first try.
Anal Sex 101: Use lube!
Okay, you’ve finger-f*cked your ass a few times and now you’re getting bored! The time has come to expand your practice and add some toys to the party. For me, it’s impossible to talk about anal without talking about lube first.
Lube Recommendations: Silicone
I recommend something thick with lots of staying power. Silicone lube is great for this! Those who have used silicone based lube know that it’s hard to wash away and can last for an entire session. There is no such thing as too much lube for first timers.
The only issue is that if you’re planning on using a silicone toy, you should stay away from a silicone-based lubricant. Silicone toys and silicone lube don't get along; the lube will stick to the toy and degrade its quality over time.
However, if you’re using glass or metal toys, give silicone lube a try. My favorite ones are Uberlube and Sliquid Silver.
Sliquid Silver
Sliquid Silver Studio Collection / Sliquid Silver
Uberlube
Uberlube 100ml & 50ml / Good to Go Traveler / Traveler Refill
Lube Recommendations: Water & Hybrid
Oil-based lube is similar to silicone in that it is long-lasting. However, oil traps bacteria and can break down latex condoms, which can be a problem. Water-based lube is super safe to use with all types of materials. Also, it’s the wettest lubricant. Your silicone and oil based lube can feel slick, but either usually isn't very wet.
The issue with water-based lubes is that they can dry out.
When this happens you can either apply more lube, or you can reactivate it with a little bit of water. Thicker lubes will sit on top of the skin for longer, making them a good choice for applying to your butt plug, and for when it comes to anal sex, you'll find thicker lubes are better for anal intercourse too.
I personally like Sutil Rich. It’s a very thick gel, with a formula that includes hyaluronic acid.
Sutil Rich
My favorite lube for all types of penetration is Sliquid Silk. It’s a hybrid lube, which means it’s a blend of silicone and water. This makes it super long-lasting and wet. This lube has a low concentration of silicone, so it might be okay to use with some silicone toys. I’d spot test a little before going for a whole session.
Sliquid Silk
Anal Sex 101: Toys for Anal Penetration
Aneros MGX Trident
Okay, now that lube is out the way, we can start thinking about our first anal toy <3. I would recommend the Aneros MGX Trident to those interested in prostate stimulation. Aneros creates medical-grade prostate toys. The MGX Trident is a good toy for beginners.
It has a little more surface area than some of Aneros’ other toys, which makes prostate stimulation a little easier. Aneros’ toys are designed to kind of anchor in place and rock back and forth. You can simply pop it in and wear it around while it works its magic.
If you don’t have a prostate, that's totally fine. you can still enjoy some G-spot stimulation from an Aneros plug.
We-Vibe Ditto
If you're not interested in prostate stimulation, you can try the Ditto by We-Vibe. It's a great little remote-controlled vibrating plug that's easy to wear. It also has an app that makes it super easy to change settings while you're wearing the plug. I honestly wish every vibrating butt plug came with at least a remote. Vibration can be a nice addition to anal because it can help increase blood flow and promotes relaxation. A vibrating plug might be helpful if your goal is anal sex with something phallic.
Njoy Pure Plugs
If vibration isn’t your thing, I might suggest the Njoy Plug in size S or M. If you’re accustomed to a few fingers, you can start at M. It’s a super wearable stainless steel plug. Stainless steel is a heavier material, which makes it suitable for putting pressure on sensitive spots. Njoy plugs come in a variety of sizes, making sizing up and anal training easy.
Kink 3-Piece Anal Trainer Set
Kink by Doc Johnson also has an Anal Training Kit made of silicone. If you'd prefer a soft silicone plug set to a weighted metal set, this is a great option. The plugs are very gradually tapered for easy insertion and compatible with water-based lube.
Tantus Silk
If you are a beginner looking to experiment with in and out sensations, you can try a small dildo. Tantus Silk in small is .75” wide and is appropriate for those who are new beginners. However, you'll probably grow out of this quickly. It might be worth it to jump to a medium if you are used to fingers. If you’re looking for a more realistic dildo, the VixSkin Spur is so cute and great for beginners!
VixSkin Spur
I wish you luck in all of your anal sex endeavors. Remember to take it a step at a time. Your asshole ain’t going nowhere! The golden rule should always be to explore with pleasure as your goal, and honor your body, its limits, and what makes your little flesh temple feel good. Who knows, maybe one day you’ll be happily taking a whole fist up your ass! The anal world is your oyster, babe <3
she/her
Kassandra is a Sex Educator at The Pleasure Chest and a student majoring in Women and Gender Studies at Hunter College. She’s working towards being a mental health counselor and, eventually, a sex and trauma therapist. Right now, she is the supervisor of The Pleasure Chest New York stores, and is having a great time.
You can find her on Instagram @x.r8ed!