If you’re in a long term relationship, chances are he’s at least “joked” with you about trying anal — after which you undoubtedly “joked” back “Yea, we totally should” while grinding your teeth and clenching your butthole.
Let’s face it, an anal expedition is scary and not for the faint of heart. But just because it takes some finesse to get right, doesn’t mean a trip down the proverbial Hershey Highway won’t be some of the best sex you’ve ever had.
PLEASE REMEMBER: Always use LOTS of lube and a condom. And never switch from back hole to front hole. And if it hurts too much, let him know!
If you’re a beginner at butt stuff, a side spooning position is as gentle as it gets. Lie on your side and let him play with your ass, rubbing, lubing it up and eventually sliding a finger in. Have him lube up your crack and rub the head of his penis between your cheeks and around your, ahem, hole, before slipping the tip in. It’s waaaaaaay better (and less likely to hurt) if he takes his time and gives you the space to relax into this one.
Look, anal is not the kind of sex that makes for a good quickie, but you can give it that kind of must-have-you-now passion with a standing pose. Push a chair against a wall and put a leg on the seat (or arm, depending on height). Brace yourself on the wall and have him enter from behind, thrusting slowly in and up. Toss your head back, arch your back and feel all romance novel-y — or as romance novel-y as one can feel mid-anal.
Lie on your stomach, putting a pillow under your pelvis for comfort and easier access. Have him rub your back, your legs, and your ass until you’re feeling fine. If he starts with a drizzle of lube down your crack and some gently probing and well-lubed fingers, it will help you feel 87 percent more enthusiastic about him going all in. And by all means, slip a hand or vibrator between your legs to give yourself the kind of stimulation you (and pretty much every other woman on the planet) probably need to come.
Start by assuming the typical reverse cowgirl position, which has charms for everyone, but for an ass man, well, let’s just say it’s good. Then, kink it up a little by letting him play with your back door with a (well-lubed!!!!!) finger or a thin curved vibrator. And, as long as you’ve gone this far, go for the trifecta by strapping a small wearable vibrator on your crotch. The triple stimulation will give you the most insane orgasm ever.
Try some role-play to get the butt sex happening. Get onto a sturdy table (a bed works too) and lie on your back, bending your knees and grasping onto your ankles (if you do yoga, it’s Happy Baby Pose). This open, vulnerable position lends itself to all kinds of scenarios: Spa visit with a masseuse who turns you on so much you beg for a happy ending? Alien abduction with requisite anal probe? Don’t worry if your idea seems crazy or weird — it’s fantasy, that’s kind of the point. P.S. It works best if he takes his sweet time examining/massaging/assessing you. Helps everyone relax, and delayed gratification always makes things hotter.
If you’re looking to add spanking to your repertoire, getting into doggy-style stance is a good gateway position. Have him get going with some thrusts from behind, with him mixing in some slaps to your butt as you both please. There should probably be some playful begging involved too — figure out your dynamic for the day and go from there. Be smart with a safe word and all that, but if you’re both into it, the pleasure/pain thing can be super intense for both of you. Don’t forget to be loud.
Sit him in a chair and give him a little strip tease, ending with your butt square in his eye-line. And if you feel like shaking it a little in his general direction, go ahead. Let him paw at it, kiss it, and tease him by rubbing it against his crotch but not quite letting him inside you until one or both or you can’t take it anymore.