How to Get More Comfortable With Anal Sex
All bodies have holes with sensitive nerve endings, and they have things to put into holes. Sometimes it feels good, and some holes take more preparation than others do.
Such is the case with anal play, where concerns like cleanliness, self-consciousness, and physical vulnerability are potentially even more pressing.
There are, however, many internal structures that make butt stuff feel good. They include the legs of the internal clitoris or penis, the prostate or urethral sponge, and the densely packed nerve bundles in the anus itself.
The average Millennial knows what’s up — experimenting more with anal play than previous generations. If butt stuff has piqued your interest, but you don’t know where to begin, this post is for you.
Maybe you’re curious and squeamish
It’s totally understandable, considering the purpose of the rectal cavity. So before I even get into tips and toys for anal training, I want to address the topic of cleanliness.
Think of the colon as the living room and the rectum as the foyer.
Generally, poop stays in the colon and only drops down when it’s about ready to exit. A bowel movement and shower a half-hour before butt stuff is enough for many people to clear that area out.
If you’re still easily grossed out and want a deeper clean, I’ve written a separate guide to clean anal sex, with tips like:
- Adjustments to eating habits
- Resources for anal douching
- Items to keep on hand for easy prep and cleanup
In a nutshell, fiber supplements, a towel, and barriers (like latex or nitrile gloves, dental dams, and condoms) help stay clean.
Plus! If you have long nails and don’t want to trim them before fingering, you can stuff a glove’s fingertips with cotton balls for cushioning. And massaging with fingers is a great way to get started with butt stuff.
Before starting anal penetration
A key thing to keep in mind is that the anus has two sphincters.
The outer sphincter is easy to consciously relax, but the inner one takes a bit more finessing.
Mindset is vital, so take some time to wind down. Deep breathing and arousal help the pelvic floor relax. As with vaginal penetration, anal penetration is much easier when you’re already relaxed and aroused, so I suggest external stimulation first.
Personally, it’s hard to go wrong when starting with a few clitoral orgasms via a rechargeable wand.
An external flicking toy like the Fun Factory Volta or Fantasy For Her Ultimate Pleasure can also feel especially pleasurable at the anal opening. And, of course, rimjobs from a partner offer sensations that toys can’t quite replicate.
Personal lubricant is a must!
For butt stuff, I generally recommend water-based lube with a gel-like consistency.
Try Sliquid Sassy or Hathor/SUTIL. They're slippery while compatible with all materials, and you can “refresh” by spraying water on.
Oil-based and silicone-based lubes last longer, but you have to consider what you’re using them with.
Oil degrades rubber (think condoms, TPE, and TPR), and liquid silicone can degrade solid silicone. So if you plan on using silicone toys, stick to a water-based or oil-based lube.
Make sure you lubricate the anus and whatever’s being inserted.
Lube shooters are great for that. As an additional safety reminder, never use anal numbing creams. If your rectal area feels pain, it’s a signal to do something differently or stop, and that shouldn’t be ignored.
Things to try with toys and fingers
The area is packed with feel-good fine touch receptors. So, as mentioned before, it helps to pair external anal stimulation with another activity before even thinking about penetration. Think, for example, of oral while circling the opening with a finger or lightly textured plug.
When starting penetration, start slow, of course. By slow, I mean slooow. Slower than you think.
Like a millimeter per second as you relax and increase pressure. But once about an inch is in, hold it in place. Don’t start thrusting. Don’t put the rest of the object in. Just keep it there for a minute. Clench and relax around it to get comfortable with its presence.
Then slowly twist it or revolve it in circles while inside.
The circling motion “tricks” the anus into perceiving the object as a little wider than it actually is, helping to relax and get ready for more. Then press harder, add lube if there’s resistance, and insert more of the length.
From here, you can press against the front rectal wall to massage the G‑spot or prostate.
Think of it as massaging behind where the pubic bone is and a little bit deeper. Fingers are fantastic for this, as are curved toys like the nJoy Fun Wand.
(Looking for beginner butt toys? Read my guide to common characteristics of the best toys for anal play.)
The best positions for enjoying first-time anal sex
Many positions can be adapted for comfortable anal play—much of it varies with angling and leg positioning, so a sex pillow can make a big difference. Two types of positions stand out for beginners, though.
If the receiving partner is on top, they’re in control of the thrusting depth and speed.
And knowing that they can start super slow and shallow can go a long way in putting their mind at ease.
As well, it potentially leaves both partners’ hands free for external stimulation. There’s plenty of room to use a wand massager on the receiving partner. Still, if you’d prefer a petite and non-intrusive vibe, the Hot Octopuss Amo and Dame Pom are fantastic options.
Spooning and side-lying positions are also ideal for anal because much of the receiving partner’s weight is supported.
Think about it: if someone has mobility problems or is full-figured, it may be a bit harder to stay elevated and sustain shallow penetration when on top.
In any case, if you know you want to limit penetration depth, an Ohnut can take up room on a dildo or penis shaft and buffer some of the length.
Wrapping it up
Butt stuff is the great equalizer—everyone has a butt, and everyone has potentially sensational internal erogenous zones.
Exploring the area may take some time and effort, but many people of all genders find that it brings their pleasure to new heights.
[This is a repost of an article originally written by Super Smash Cache for Spectrum Boutique. This version has some modifications to fit my website's layout!]
As a transmasculine person, I sometimes get dysphoric when reading about prostate play. I really like how you grouped the prostate together with the urethral sponge, so I didn't feel like my body was missing something. 🙂
Thanks for this guide <3