Up the ass; around the rim; in and out the anus; shallow, deep, soft hard; behind, on top, beneath, beside; with fingers, hands, toes, tongue, toys, dildo, strap-on, cock: The ways to play in your own and your partner’s butt are limited only by your imagination and sense of adventure.
An anything-goes mentality seems to accompany anal play, perhaps more so than even pussy or cock play. Maybe that’s because just going “there” feels transgressive in itself, sparking the shadowy parts of our sexual selves and releasing our inhibitions. Or maybe it’s because, like opinions, everybody has an asshole. Double the pleasure – double the fun!
Before we dive into the medley of options for anal pleasure, let me remind you of the importance of communication in all sexual activities. Communication really matters where ass play is concerned because, if you’re not doing it right, it can hurt.
Knock before entering, asking permission to place anything, including your fingers, at or inside the back door. And remember, whether you’re the giver or the receiver, that our bodies differ from moment to moment, from hour to hour, and from week to week. What felt good last time might not, next time.
Once you’ve begun anal play, ask your partner frequently how they’re feeling. Are they enjoying themselves, or not? Do they want you to go softer, harder, more lightly, shallower, or deeper, or to stop altogether? As receiver, make sure to speak up at the least amount of discomfort so your partner can slow down, change their approach, or stop.
As giver, pay attention to non-verbal cues, as well. Does your partner’s body suddenly tense up? Do they suck in their breath? Is that a moan of pleasure or a groan of pain? When in even the slightest amount of doubt, ask. Even when you think you know: ask!
Preliminaries aside, here’s an exploration of the many ways – 28, not 50, but we wanted to leave something to your imagination – to enjoy that mysterious, nerve-ending-filled nether region that is the ass.
A world of pleasure
Fingering
Make sure the nails of any fingers involved in anal play are short and smooth, or wear a surgical glove. Wash your hands or remove the glove before touching any other area of the genitals.
1. A single finger stroking or pressing on the perineum, the small expanse of skin between vagina and anus
2. A well-lubricated finger (with short, smooth fingernails or wearing a surgical glove) circling the asshole
3. A single finger slipping just inside the hole to play with the many nerve endings at the opening
4. Two fingers slipping in and out of the anus, stimulating, relaxing and expanding it
5. A finger sliding deeply in, up to the second knuckle, to massage the prostate gland (men). We’ll provide a more detailed guide on prostate massage in a future post.
Rimming
This type of anal play can feel so exquisite, even orgasmic, to the receiver.
As the giver, if you’re squeamish about rimming or worried about bacteria, make sure your partner’s asshole is thoroughly washed and perhaps shaved before going in. In our experience, a little bacteria is OK: the stomach is pretty well able to kill off small amounts of e. coli or other germs, unless your immune system is low. But it never hurts to clean!
5. Licking the asshole with the tip of your tongue
6. Flicking the tip of your tongue around the edge of the asshole.
7. Sticking your tongue inside the asshole
8. Taking your partner’s ass in both hands and plunging into the asshole with your mouth and tongue, licking and teasing away.
Positions for rimming:
9. Doggy style, with their butt in the air and you behind them, perhaps playing with their cock or pussy as you dine
10. Up-and-over, their legs in the air and over toward their head as they lie on their back, with you kneeling between their legs
Anal plugging
The anal plug (here and here) can be a great show opener before the Big (pun intended) Event, be it pegging, anal dildo play, or butt-fucking. For the beginner, a smaller-size plug might work best; starting small and progressively opening up with larger sizes can be a delicious experience, in one session or over several. Consider investing in an assortment of sizes!
11. Placing a well-lubed plug into their ass to intensify their orgasm
12. Having them wear an anal plug as a part of dominant-submissive play
13. Putting in the plug about 20 minutes before moving on to dildo platy, pegging, or anal intercourse to relax the sphincter muscles
14. Inserting a small plug, then moving up to a larger one, and so forth until a dildo or penis just seems a natural next step
Anal beads
These little jewels can take the pleasure of the anal plug to the next level. Wearing them feels like a plug is going into your ass again and again, which can be delectable. come in different sizes and styles: some taper, starting small and graduating to quite a large size; others are consistently one size, smaller beads. All have a handle or loop at the end to keep them from slipping all the way into your intestine.
Douching is a good idea before engaging in anal-bead play, as they penetrate quite far up the rectum and can bring fecal matter or bacteria out with them.
15. Insert the beads one by one into your own asshole, using lots of lube, and breathing and relaxing after each bead. Masturbate, and pull them out just as you begin orgasming. They will stimulate your rectum in a delicious way!
16. Do the above for your partner, and fuck or masturbate them with the beads inside. Let them pull the beads out, if they desire.
Dildo play
So many dildo types, only one asshole! What’s an anal aficionado to do?
17. Sliding a vibrating dildo into their ass and turning it on, then fucking them with it while they stroke their penis. This one is designed for asses, in a smaller size and with a flanged base.
18. Slipping in a vibrating dildo with an extension that rests on their clitoris or perineum, and turning it on. This is great for prostate massage, covered in our next post.
19. Fucking them gently with the narrow end of a glass dildo while squeezing or stroking their balls or pressing against their perineum
20. Placing a thrusting dildo into your own ass, turning it on, and letting the cartoons begin!
Pegging
For some men, there’s nothing sexier than getting pegged. It feels not only good, but maybe even transgressive. (And no, enjoying getting pegged does not make you gay!)
Before even putting on the harness, have the “talk.” Are you both comfortable, and ready for this? If the receiver is experienced with anal sex, ask: how fast and how deep should you, the giver, go?
Receiver: remember that the giver can’t feel the dildo strapped into the harness. It’s up to you to tell them what’s going on. If your butt clenches, say so. If you need more lube, speak up. Otherwise, they might not know.
Pegging is a more advanced form of anal play – not for beginners. You should have at least dabbled in other anal adventures, such as fingering and anal plugs, so that you’re both comfortable communicating and so that the receiver is absolutely certain that they like anal play.
Receivers should have fucked themselves with an anal dildo, too, so they know what feels good and can direct the giver.
Givers, make sure your harness is nice and snug. Put the dildo in and practice in advance. Be aware that you’ll be using muscles you might not normally use, so check to see how long you can thrust. Consider different positions, as well, and make sure the dildo points upward, for prostate or G-spot/urethral stimulation, instead of downward, which could press against the receiver’s backbone – not a great feeling.
Also think about how you might multitask: many men need penile stimulation during pegging to come. Ditto for women and clitoral stimulus. How can you do this while pegging them? In some positions, they may need to stroke themselves.
Use lots and lots of lube, before and during. Water-based is best with a silicone dildo: oil isn’t water-soluble and can degrade the silicone, as will silicone lube. But water-based lube dries out quickly so needs to be replenished very frequently. Err on the side of too much rather than too little!
And be patient. In our experience, pegging takes five practice runs to become an awesome experience. After each trial, debrief. What worked? What didn’t? What would you like to be different next time?
21. Strapping on a dildo and sliding on in, using lots of lube and communication.
22. Strapping on a dildo with a G-spot stimulator for a female giver’s pleasure. This one works well but only if you’re more experienced at pegging, as the dildo is not flexible.
Positions for pegging:
23. Doggy style: Receiver on hands and knees and giver behind.
24: Receiver on their back, legs up
25: Giver on their back, receiver on top
Butt-fucking
Men will be the givers in anal intercourse; receivers can be male or female.
Pretty much the same rules apply here as for pegging: Warm up and relax the ass beforehand with finger or fingers, anal plug, small dildo, etc. and use great heaping gobs of lube, again and again.
Warming up is super important. Perhaps plan an anal afternoon or even an entire day for this practice.
Giver: If your receiver is a novice to fucking, use fingers first and then maybe have them wear a butt plug, starting perhaps with a small one and then graduating upward as time goes on. Twenty minutes or so per plug ought to be enough.
Perhaps they could wear the plug while you give them oral sex or, if the receiver is a woman, fuck her pussy. So much the better if she comes – it could very well happen again while you’re in her ass, and the spasms will feel so good on your cock that you might come, as well. Double the fun!
A caveat: Anal intercourse can be super pleasurable for the receiver as well as the giver if done properly, but it also produces sensations that you might not be used to feeling. Expect pressure but not pain. Pressure can feel strange and your butt may clench – and that’s where the pain can start.
If you feel pressure but it’s overwhelming, tell your partner. Giver, if this happens, ask: should I slow down or stop? This might be the time to grab a vibrator and place it on her clit. This can relax her and also give her intense pleasure. Toys are your friends! If your receiver is male, try using a stroker or giving him a hand job.
Receiver, try to stay relaxed. This can mean pushing against the penis as if you’re having a bowel movement.
One time to be especially careful is during the receiver’s orgasm. The spasms will cause the sphincter to clench, which can be painful if the giver is still thrusting.
Receiver: Communicate! Tell your giver if you feel an orgasm coming on.
Giver, you may stop at this point and let the receiver enjoy – and, as mentioned above, it will be pleasurable for you, too.
Positions for butt-fucking:
26. Doggy-style, receiver behind
27. Receiver on their back, legs up or bent
28. Side-by-side, spooning (this lets the giver stroke the
receiver’s clit or penis, or penetrate the vagina, at the same time) You can find all of our anal exploration here. Happy Exploring Kinky Friends.
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