"More men should get their bootyhole played with." That's a word to a good friend during a candid girl talk. And though the language is probably not the best for introducing your partner to the idea of giving him a prostate massage, as a cishet woman, I have also come to realize it's sometimes our own colonial ideas around masculinity that keep us from opening the floor for discussions around acts such as giving prostate massages. Or, in some cases, what makes it a difficult topic for men to broach within their partnerships.
For everything men are open to trying during sex, it's very rarely "butt stuff", especially when it comes to their own anus or that vicinity. Despite the fact that their version of the G-spot, called the P-spot, is located in their anus, the approach that most men take is: so what if the prostate massage is the golden gate that unlocks potentially better orgasms?
But I imagine that there are more than enough men who have expressed (whether internally or externally) some curiosity along with their uncertainty, whether it be through sharing fantasies or not totally shutting down when put on the table. At least that it what I have found in my observations during my brief time as a sex educator. I've also noticed that when Black and brown men reach a certain tax bracket, they are less afraid to express fantasies and desires that might otherwise stray from the typical ideals of masculinity. Which makes sense (but is also a different topic for a different day). Nevertheless, where's the fun in life if we're waiting to become the next 50 Cent before we begin to explore our sexuality through new experiences?
So, the only question that remains is, how do you put all your cards on the table while providing a comfortable and safe space for introducing the topic and act of prostate massages?
We spoke with Sex and Pleasure Educator, Luna Matatas for the specifics on prostate massages for Black and brown men who in many instances hold hegemonic views regarding their masculinity and thus their sexuality. While a guide like this might normally dive right in and give you the steps to the actual massage, any sex educator will tell you the communication and consent around any act is the very first step in all actuality. You want to create a safe space because men are deserving of that respect. And ladies, from our own experiences, we know all too well what a difference it makes when comfort and communicativeness are standards held in the bedroom.
Matatas provides a number of ways we can hold space for any and all feelings that might come up while introducing the idea of prostate massages with your partner.
How Can I Introduce A Prostate Massage To My Partner?
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- Talking about prostate pleasure in a way that is curious, exploratory and doesn't have an end goal, like penetration, can be a good way to hold space for any feelings like shame or guilt we have when talking about pleasure.
- Bring up prostate pleasure when talking about other fantasies or sexy things, like G-spots, kissing, massages, sex toys, is a great way to talk about overall erogenous zones on the body. You can talk about ones that are under-explored, like the prostate and erogenous zones that are under-serviced like earlobes and necks or backs. Create a pleasure exploration package of the erogenous zones you might be interested in exploring. Talk about each one in terms of what makes you excited and what makes you anxious or insecure.
- Look at sex toys online together and make a list of the toys you're both curious about using on yourselves and each other.
- Be upfront, own your uneasiness — we ALL have uneasiness around aspects of sex — body shame, performance anxiety, guilty fantasies. Putting it out there can be an opportunity for a partner to be empathetic, reassuring and share their own uneasiness.
- Playing with knuckles and massaging the perineum is a great way to give a gentle massage to the prostate without penetration. This can be done while pleasure is happening to other parts of the body like the penis or testicles.
- Last but not least, for the men who might be reading along, playing with your prostate on your own during masturbation is also a great way to get comfortable with what your body does during prostate pleasure, what pressure or stimulation feels good and what doesn't.
How To: Your Ultimate Guide To Giving Someone A Prostate Massage
Now that all the formalities are out the way, let's get into how to give a prostate massage. All of our teenage lives we mastered the art of handjobs and as young adults we've all but been trained up for the blowjob olympics. So how do we weave all of the gems dropped here to deliver on a fire ass (no pun intended) prostate massage? Step by step, Luna Matatas breaks it down for us, here:
Step 1: Get into a comfortable position - try lying on your stomach with a pillow under your pelvis. If you want to be able to watch your partner, lie on your back and prop up your pelvis with a pillow to give a better angle.
Step 2: Stimulate the butthole first - warm up the external nerve endings to relax the anus and the person
Step 3: Go slow, use lots of lube and check in with each other - faster, slower? Harder, softer?
Step 4: Add pleasure to parts of the body that you know enjoy stimulation. (Not all penises get erect during prostate pleasure and not all prostate massages result in ejaculation. It's OK to just enjoy the relaxing sensation, a new way to explore pleasure or prostate play on the way to other types of sexy things.)
Step 5: Use lube and massage the butthole with your thumb or knuckles as if you were pressing it like a doorbell, no pressure to penetrate at this point.
Step 6: When your partner is ready, you can gently slide the tip of the finger in at an angle towards the front of the body (towards the belly button). Straight up penetration can feel jarring, so we want to creep into the butthole from the bottom and then inwards. Picture having your thumb against the butthole and gently bending it inwards with lots of lube.
Step 7: Once inside, you can circle the anal canal gently, check in with your partner, add more lube.
Step 8: Then start to bend your finger towards the anterior part of the anus (think about heading towards the back of the testicles) and gently massage back and forth or in circles until you find an area that feels more sensitive for your partner. For your finger, it might feel firmer. Curve your finger tip towards the front of the body and increase pressure to find the right spot.
Step 9: Prostates like firm and continuous pleasure, so try circles, swiping side to side or light tapping — all in small movements and see which one your partner's body enjoys. Experiment with speed, slow it down and pair it with eye contact, dirty talk or using your other hand to add pleasure somewhere else if that feels good.
The Best Lube For Prostate Massages
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Once you've had the dialogue and consent has been provided, you want to put more emphasis on the physical comfort. This is where ensuring that you and your partner are using lubricant comes in.
If you've ever tried anal play without lube, you're well aware that it can be easy to write it off afterwards (understandably so). Anal play without lube can cause the skin to break or tear. And to this Matatas further elaborates by explaining, "The anus isn't self-lubricating, like the vagina, so lube is a must." If you're normal, you might feel overwhelmed by the world of lube readily available on the shelves of the internet (without the guidance of a salesperson), but don't worry Matatas has you covered there as well. She adds, "You want to use a thick and long-lasting lube; silicone lubes are great and so are thick water-based lubes. Don't forget to re-apply during penetration, sometimes we lubricate at the start, but forget to re-apply once we get going! Using lube creates a silky smooth texture in the rectum that makes penetration more pleasureable and less likely to cause damage to the anal tissue."
Now, should you be using toys at any point during the prostate massage, Luna recommends using a water-based lube for silicone toys. However, "If they have a favorite silicone toy and like silicone lube, throw a condom on the toy." I will also add that if you're planning on taking this to the shower at any point, water lube should be switched out for a silicone lube.
Sex Toys For Prostate Massages
If you are, in fact, looking to incorporate toys into the prostate massage that you're providing, according to Matatas, "Check out prostate sex toys — with or without vibration, they are shaped in a way that makes it easy for you or a partner to reach the prostate."
In fact, this might actually be a nice change of pace as she further states, "Prostates also like firm and continuous stimulation - and sometimes fingers can't provide enough firmness or they get tired." Matatas adds, "Smaller, smooth, rounded tip butt plugs with flared bases are great for anyone who is just started to explore anal penetration and can help train the anus to take penetration more easily over time. You can put in a butt plug while your partner is doing other sexy things you already are familiar with like oral or kissing, and this will warm up the anus for more direct prostate play later on."
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The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak