Editor’s Note: This Playboy Advisor by Bobby Box featuring questions surrounding the prostate was originally published on Playboy.com in August 2020.
Q: I’m a 27-year-old woman in a heterosexual relationship, and I would like to bring up the topic of prostate play to my partner. He’s pretty sexually open-minded, and we’ve talked a few times about exploring beyond penis-in-vagina penetration. What’s the best way to communicate my curiosity in prostate play without scaring him or making him feel uncomfortable? —T.L., San Diego, California
You mention your man is sexually open-minded, so approach the conversation casually––don’t plan a speech or anything. It’s 2020, and butt stuff is finally being acknowledged in the mainstream as a legitimate source of sexual pleasure, even among heterosexual men who’ve been under the impression that anal play is “gay.” This belief system, of course, has homophobic roots, and it isn’t a cute look on anyone. The prostate is a gland, not a sexual orientation.
A survey from sex toy manufacturer LELO found that 71 percent of straight men in relationships have tried, or would like to try, prostate play, and 80 percent of women are open to sharing in that experience. Since men who incorporate prostate play into their sexual routine can experience orgasms up to 33 percent stronger, this has potential to be a total game changer and a fun way to mix up the dynamics in your sexual relationship. Of course, consent is what’s most important here, so whatever you do, do not shove a finger up his unexpecting ass. This will effectively diminish any future attempts at anal play. Instead, start by complimenting his bum. Playfully pinch or squeeze it when you’re together. His reaction will help you get a better sense of his comfort level.
The next time you’re chatting (in person or through text) and the conversation gets hot and heavy, throw out the idea that you’d like to try something––something you think he would really enjoy. (Knock on the back door before opening it, if you will.) Ask if he’d be open to butt play and tell him how hot you think it would be. If he knows the idea turns you on, he may be more receptive to being…receptive.
If his cues are positive, you can start by stimulating the prostate externally through the perineum—the swath of skin between the balls and the b-hole—the next time you’re intimate. Next time you’re giving him a blow job, gently rub the area (it will feel like a plum) in a circular motion and gauge his reaction. It’s a noninvasive way to test the waters and, provided he’s loving this new trick, will further open his mind and his cheeks to a well-lubed finger (trim your nails prior!) or a toy, such as a prostate massager.
If he’s not receptive, don’t force it on him. Sex is best when all parties are actively enthusiastic about what’s taking place.
Q: I’m a freshly out-of-the-closet gay male in my early 30s, and I’ve never experienced an anal orgasm or prostate orgasm. I would like to experiment alone before I engage with a partner, and I wanted to know if you had any tips for the best toys or lubes to use for stimulation? What is the safest way to go solo? ––S.P., Plano, Texas
As somebody who came out in his late 20s, I can totally relate to your experience. Truth be told, it took me some time before I was completely comfortable with anal sex––and it took even longer until I became confident.
I think it’s a great idea to experiment with anal sex toys before engaging in penetrative partnered sex. It helps you get to know your body at a rate you’re comfortable with without the pressure of rushing into anything.
The anal sex toy market is expansive and can be overwhelming, but the category can effectively be summed up in four parts: butt plugs, prostate massagers, anal beads and dilation kits. All have their own merits and only through trial and error can you decide which is best for you.
Before paying for a sex toy, however, I suggest you explore your prostate with your fingers and discover which sensations feel best. Enter about three or four inches in your rectum with a lubricated finger and gently play around in the area. The prostate has a distinct texture (like a soft walnut) and you’ll know when you’ve hit it. Many say prostate massage feels like the beginning of an orgasm. If you feel a sudden urge to urinate, you may be applying too much pressure. The sensations you enjoy during this time can offer valuable intel when purchasing a sex toy. Also, it’s free!Since you say you’ve never experienced an anal or prostate orgasm, I recommend you start with a dilation kit. These are a series of anal sex toys––often butt plugs––of graduated sizes designed to get your bum accustomed to anal play at a comfortable pace.
When you feel like moving to the next toy in the set (which is slightly larger), insert a finger alongside your current toy first. If the finger slides in without resistance, that’s your green light to upsize. If it’s uncomfortable, stick with the current toy for another day or two. Your body will let you know when it’s ready.
If your goal is to experience a prostate orgasm, prostate massagers have an intentional curve designed to directly stimulate the prostate. They also tend to have fun vibration settings for added stimulation. I recommend the LELO Hugo or LOKI Wave, the latter of which is the first prostate massager to offer the beloved “come hither” motion that’s largely favored for prostate play.
Now let’s talk lube, which is absolutely necessary when using sex toys. Water-based lubes are the most versatile of the bunch and can be used with a wide spectrum of materials. However, they don’t last as long as other lubricants and you will likely have to reapply, which can be a pain in the butt (wink). If you do opt for a water-based lube, choose a thick or gel-based formula, as they tend to last longer. Try Tush Cush by Cake, which is a water-based jelly made specifically for butt-stuff beginners.
Silicone-based lubes are longer-lasting and largely favored for anal sex because of their silky texture and glide. If you choose a silicone lube (Cake’s Backside Slide is my go-to) don’t use it with silicone sex toys, as it can deteriorate the material.
Hybrid lubes (see: Ride Silk Hybrid) are another fine option. These are largely water-based lubricants made with a small amount of silicone so you can get the desired texture that silicone lubes offer while being able to use them with silicone sex toys.
Lastly, you can also use an oil-based lube, which is the longest lasting but also the most difficult to clean. Though you may not be using barriers with your sex toys, it’s important to note that oil-based lubes are not condom compatible, nor should they be used with plastic or latex toys.
Q: I enjoy being a recipient of prostate play in my relationship, but I have yet to orgasm from it even though I find it highly pleasurable. Is it normal to never experience a p-orgasm despite being comfortable and aroused? Is there something I could be doing differently? ––G.G., Bellingham, Washington
What may be occurring here is that you are experiencing a prostate orgasm, but not seeing any “evidence” of it in the form of ejaculate. This is fairly common. Prostate orgasms can occur in the absence of ejaculation––some refer to these as “dry orgasms.” Another thing about prostate orgasms: They can happen over and over again with no grace period. Many have multiple orgasms without seeing any semen at all. Because you mention you’re comfortable and find the experience highly pleasurable, this could be what’s happening.
Beyond that, I want to emphasize that we should stop being so goal-oriented about sex. An orgasm does not a sexually gratifying experience make! When we approach sex with a goal in mind (e.g. orgasm) it can suck the fun out of the experience. As the saying goes, “Life is about the journey, not the destination.”
If an orgasm does happen, great. If it doesn’t, no biggie. Did you have fun? Did it feel good? That’s all that matters. We get so caught up in these arbitrary rules that it can take us out of the experience and leave us feeling guilty. Sex is about pleasure, not shame! That being said, if you think the issue could be that your prostate is not being stimulated in a way that brings you to orgasm, there are a few things you can try.
Try stimulating the prostate externally, then internally. Try both at the same time (though you will likely need a toy to do this). Some find it easier to experience a prostate orgasm while they’re stroking their shaft.
Next, play around with how you’re touching your prostate, applying different pressure. Try the “come hither” motion, then try some gentle taps. Try tracing around the entire gland in circles, and try a vibrator. You may find that one technique or a combination of many is what it takes to produce a prostate orgasm. You can even change your positioning: You can enter doggy style, on your back, lying on your side and so on. Lift your leg or place a pillow under your hips if it helps. There is no one universal way to have a prostate orgasm, but it can be a lot of fun finding out which techniques work best for you.