Consent is key.
I’m sure this will come as a surprise to approximately no one, but I'll say it anyway so that we can begin this article coming from a place of truth and understanding — I'm very into butt stuff. All things revolving around the derrière I find utterly fascinating. Just yesterday, while standing behind my partner in the shower, I found it literally impossible not to repeatedly smack his butt while he washed the shampoo from his hair.
I'm just into the butt. I was doing some light reading about the prostate the other night, as I often do, and it occurred to me that all of my personal anus exploration has been almost exclusively trial and error.
Sure, there are plenty of “how to have anal sex” guides to assist us through the conquering of our own butts, but I wanted a manual to guide me through the passageways of prostate stimulation.
Being no stranger to all things anal on my backend, I wanted to know more about how to finger a guy’s ass. I wanted to make a little “how to” for all you wayward butthole adventurers to have at the ready for the next time you want to go to town on your partner.
To help in this endeavor, I asked Amy Levine, sex coach and founder of Ignite Your Pleasure, to help me help you.
What Exactly Is A Prostate?
The prostate is a gland surrounding the bladder in people who were assigned male at birth. Its main function is to release prostate fluid, which is one of the elements of semen. This small, walnut-shaped gland is essential to the reproductive process. It's located just inside the rectum and can be reached through the anus.
Many people enjoy having their prostate stimulated. Levine simply explained, “It feels good.” To say the least, a penile orgasm might cause contractions between four and eight times, but a prostate orgasm can cause as many as 12.
Why Do Some Men Not Like Prostate Stimulation?
Some people are nervous or turned off by butt play, possibly because of internalized homophobia.
There can be a lot of stigma around this part of the body for men, but there shouldn’t be. As Levine puts it, “It stems from homophobia and what it may mean if they enjoy it. All it means is that they like their prostate touched -- it's not an indication of their sexual orientation.” The bottom line: Prostate stimulation can feel good no matter who someone’s attracted to.
Others might not enjoy it for the same reasons anyone might not gravitate toward specific bedroom activities: lack of interest, personal discomfort, and so on.
How Do I Have The Fingering Conversation?
The most important part of learning how to finger a man, Levine says, is starting a conversation about experimenting with prostate stimulation. You shouldn't just stick your finger in your boyfriend's butt without his consent.
Levine suggests making it about a larger discussion about anal sex. If you’re interested in receiving backdoor play, too, you might say, “It's a conversation starter about if he wants to try anal sex on you, and you can say, 'I'm open if you're open to anal exploration too.'"
Mostly, it's about being honest and open. Sex should be fun and explorative for all parties involved, not a high-pressure negotiation.
How Do I Actually Finger Him?
Even before you have the conversation about anal play, you can gauge your boyfriend's interest in butt stuff by asking to engage his perineum. Also known as the taint, the perineum is the space of skin between someone’s testicles and anus. It can feel really awesome to have it stimulated. You can stimulate it by using your index and middle fingertips together, gently stroking, rubbing, or pressing your fingers against it. Careful not to engage your nails. If they’re interested, see what works for them.
You can also try this the next time you're giving him a blow job. Reach up and press two knuckles against his taint and knead gently.
I also suggest trying prostate stimulation while you're in the reverse cowgirl position. You want to be able to easily reach the area without too much strain on your body. It's always not the easiest gland to reach during sex.
Perhaps it goes without saying, but prostate stimulation is much more exciting for the receiver when there’s already been foreplay of some kind, a sensual massage, or the like. Make them feel sexy and at ease. I also usually put a condom over my finger before insertion because I have long fingernails.
Levine gave us a solid breakdown on how to reach the prostate when you’re learning how to finger a guy:“When he's lying on his back, either of you can slide a well-lubed finger or toy slowly into his rectum along the belly button side of his body,” she says. Lube is indeed vital here, and a water or silicone-based lube in particular will make your anal adventure as smooth as possible. “The gland can be felt about an inch or two inches deep. [While] the prostate is actually on the other side of the tissue, this is how it gets stimulated.”
Once you get to the prostate, which according to NYU’s Langone Hospital has “a rubbery, soft feel and is symmetric with a smooth groove down the middle, separating the right side from the left,” you can gently touch it, moving your fingers upward, or hold a toy against it to increase stimulation. Ask what works for them as far as speed and intensity and adjust accordingly. If they’re really enjoying themselves, a white fluid might emerge--you may have heard the phrase “milking the prostate,” and this is where it comes from. It also means they’re close to having an orgasm, so stick with it. You may also want to go down on him or stroke his penis at the same time to give him an extra jolt.
If you're looking to use butt toys, again, always ask first, but Levine suggests The Hugo. I'm a big fan of Doc Johnson's butt toys. Just remember that butt toys need to have a flared bottom. Otherwise, you risk losing them in the anus and that could mean a trip to the ER. Do not put a regular vibrator or dildo up a butt. It can cause cross-contamination and result in infection and you run the risk of permanently tainting your toys with an unpleasant odor.
Now, who’s ready to explore?
Amy Levine, sex coach and founder of Ignite Your Pleasure
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