W

hen it comes to butt play for guys, it's normal to be a lil' intimidated. After all, heading around back is a mainstream enough act that you know it can feel pleasurable for men, and yet, actually trying it can be anxiety-inducing if you have no idea what you're doing back there.

In that case, here's everything you need to know about milking a guy's prostate, which is accessed through his bum, to give him a next-level orgasm.

    1. The prostate is highly sensitive. The prostate, which is located inside a man's rectum, has a ton of different nerves, says Dr. Michael Ingber, MD, a board certified urologist. There are small sensory nerves, parasympathetic nerves (that come into play with erections), and sympathetic nerves (that come into play with ejaculation), which make it incredibly sensitive and responsive to gentle touch... in the best way.

    2. Although it's rare, some men can orgasm through prostate play alone. This tends to be a learned technique, says Dr. Evan Goldstein, CEO and founder of Bespoke Surgical. What's more common is to combine prostate play with oral or manual sex for a more intense orgasm.

    3. It's probably a good idea for your guy to go to the bathroom and try to empty his bowels before diving into prostate play. Goldstein notes that if your partner has a regular bowel schedule and is eating a lot of fiber, they'd likely be ready for a prostate massage without much pre-planning. Since the prostate is located close to the opening of the rectum, this area is usually void of any stool, especially if someone is pretty regular. However, for extra peace of mind, Goldstein suggests having your partner hop in the shower and inserting a well lubed finger or toy into himself. If it comes out clean, you're good to go, otherwise, have him try to go to the bathroom or perhaps raincheck the prostate massage for another day.

    4. Cut your nails! Seriously, think about how nasty it is when dudes don't do this for you.

    5. You're gonna need to use plenty of lube. Unlike the vagina, the rectum doesn't self-lubricate, so you'll need lots of lube if you want to enter butthole territory. Goldstein recommends water-based lubricant since you can use it with toys and it doesn't stain fabric. But many people prefer silicone lube (which, note, is not compatible with silicone toys) as it tends to last longer and stay wetter than water-based lube.


    6. You'll know you've hit the prostate when you feel a "walnut." Insert one or two very lubricated fingers slowly into your partners rectum while facing them. You'll want to reach your fingers as if you're trying to touch their belly button with your fingers fully extended, says Goldstein. Try to touch for the prostate using your finger pads. It should feel like a walnut and your partner should feel increased sensitivity in the penis when you touch it.

    7. There are two lobes to keep in mind when giving a prostate massage. The prostate has a left lobe and a right lobe (hence the walnut analogy). "It’s best to start working the left lobe from left to right, deep to superficial, and then the do the same for the right lobe," says Goldstein. Repeat this as your partner wishes, but make sure you're not going for hours or really jamming your fingers up there as it'll obviously cause pain.

    8. It might take a few minutes. Just like how you can't be expected to orgasm after 30 seconds of oral, guys can't be expected to just magically orgasm after 30 seconds of prostate play. Every body is different, and while some might say that within seconds of starting a prostate massage they'll orgasm, know that it usually takes a few minutes before anything starts feeling good. Be patient, and communicate with your partner throughout to make sure they like it, of course.

    9. Don't stress if it doesn't seem like anything's happening on the first try. If you and your partner are comfy with trying again, try again! "There is for sure a steep learning [curve] to prostate massage," says Dr. Jamin Brahmbhatt, MD, a Urologist at Orlando Health. So don't stress if it's not the magic ejaculation button you thought it'd be in three seconds or less. Goldstein adds that since the sphincter is naturally tight, it makes sense that someone might take a few tries to fully relax and get comfortable with the idea before it becomes pleasurable.

    10. This move is called prostate "milking," but it's not because semen looks like milk. It more relates to the movement: Just like how milking a cow requires manual manipulation of the cow's udder, you're using your hand (or more specifically, finger) to stimulate a man's prostate, says Goldstein. Also, what you are actually milking from the prostate prostatic juices. Semen is just a small fraction of ejaculate, while the prostatic juices make up the majority.

    11. There can be health benefits to prostate play. When done correctly, prostate milking (or massage) can help decrease localized inflammation like prostatitis (picture a clogged drain with a ton of pressure building up behind it), says Goldstein. Dr. Brahmbhatt adds that doctors may sometimes perform prostate massages to obtain fluid samples when assessing for prostatitis.

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    Carina Hsieh
    Sex & Relationships Editor

    Carina Hsieh lives in NYC with her French Bulldog Bao Bao — follow her on Instagram and Twitter • Candace Bushnell once called her the Samantha Jones of Tinder • She enjoys hanging out in the candle aisle of TJ Maxx and getting lost in Amazon spirals.