Headshot of writer wearing sunglasses and a hat with bananas on it

by Bobby Box

People tend to think that because I’m a sex educator and columnist I’m some pro-fucker and know-it-all. While I would love the confidence and delusion to describe myself in such a way, the fact of the matter is that sex is too subjective to make such a boastful claim. 

To describe yourself as an expert in this industry doesn’t make you some mythical oracle of orgasms. It merely means you’re a sex nerd who’s dedicated your career to studying sex, sexuality, anatomy, etc. so you can offer informed options and solutions to assist others in having the best sex of their lives.

While I am indeed a sex nerdwho recently received their certification to teach queer-inclusive sex ed (thank you so much!)I can say with certainty that my most valuable lessons come from my worst sexual experiences, as they force me to reflect on what went wrong and what could have gone better.

As someone who has been hospitalized after a particularly gruesome anal encounter, I’ve learned my lesson and now anal sex is a topic where I feel most adept. (Plus, gays are to anal as lesbians are to cunnilingus.) In that spirit, think of me as your gay best friend. A Judy who wants nothing but the best for your bum.

Now let’s talk butt stuff. 

Woman's butt seated on a patio chair with a small purple butt plug resting on the butt crack

No prostate? No problem!

More often than not, I need prostate stimulation to orgasm from partnered sex. Many gay men belong to this camp, which is why we compare our community to tupperware: The bottoms always outnumber the tops.

Individuals assigned male at birth have prostates, walnut-sized glands located roughly six to eight centimeters inside the rectum toward the belly button. The prostate has been coined the “P-Spot” and “male G-Spot” because it’s surrounded by nerve endings that feel oh-so-good when stimulated. 

Since those assigned female at birth don’t have prostates, there’s a misconception that anal stimulation is not pleasurable, but there are plenty of other erogenous zones in the area and orgasms from anal sex alone are indeed possible.

“Blended orgasms from this combo can be extremely delicious,” Kenneth Play (he/him), sex expert and educator, explains.

To help you relax into the feeling, use plenty of lube, enter slowly, and for those with vulvas, pair anal stimulation with another familiar sensation (i.e. clitoral, vaginal). 


Hit the G-spot from the back.

Good news, vulva-owners: The G-spot (and the elusive A-spot) can be accessed from the anus! In fact, most anal orgasms occur through indirect stimulation of the G-spot via the shared wall between vagina and rectum. 

If hitting the G-spot is your goal, use the same techniques you’d use when accessing it vaginally (the “come hither” motion is a fan-favorite). 

It’s more difficult to stimulate the G-spot through the anus with a penis, though some positions can better your odds. Play believes the best position is the “happy baby” yoga pose, placing a pillow under your hips to angle the pelvis for direct contact.   

Two hands with pink nails grabbing a woman's butt cheeks against lime green background

Get peachy clean. 

If sex is planned, you can eat for a cleaner colon a day or two prior. Gays tend to starve themselves silly in anticipation of a hook-up, but it’s completely unnecessary. Instead, eat right, opting for high-fiber foods like fruits, veggies, rice, and leafy greens. Flaxseeds will help regulate bowel movements and a spoonful of Metamucil before bed is *chef’s kiss* 

If you adhere to a fiber-friendly diet and have had a bowel movement 30 to 60 minutes prior to anal play, a gentle wash with antibacterial soap should suffice. But if you prefer to put in added steps to ensure no “mess,” you can douche. (But if there is mess, don’t freak! You’re dealing with the bum and we all know what bums do. Every gay has a painting story). 

Roughly 30 minutes to an hour prior to playtime, hop in the shower, fill your douche bulb with warm water to prevent cramping (do not use the solution found in most drug stores), lube the tip of the nozzle (silicone lube is waterproof), insert the nozzle, and gently squeeze the bulb. When the water is in, wait a few seconds and then empty your bowels into the toilet. Repeat this process until the water runs clear. 

Unfortunately, no technique ensures a mess-free experience, but eating right and douching are the most effective methods for prevention.


Let toys be your guide.

Solo exploration is the best way to start. Start with a finger (you have ten and they’re all free!) and work your way up to toys of graduated sizes. A great way to determine if you’re ready to upsize is to insert a finger alongside the current toy and make a judgement call.

Again, use a lot of lube (however, if your toys are silicone, do not use a silicone lube; the two don’t mix), applying to your hole, your toy/finger, and inside the bum. Your body will let you know when you’ve gone too far, so if you experience pain, ease off.  

Don’t be too concerned with penetration right away. Let your bum get used to being open and full. Butt plugs like the BOOTIE or a rumbling B BALL UNO are excellent for adjusting to this sensation. Go for a walk with one, I dare you! 

Whatever you do, make sure the toy has a stopper at the end, like the flat base at the end of a dildo. Without one, your bum will eat that thing right up and you will have to get it removed at the hospital. As someone who’s been hospitalized for an anal-related incident, I don’t recommend it. 

So let me, your new GBF, leave you with this: To make all your anal aspirations come true, do as I say and not as I do.


Bobby Box (he/him) is a freelance sex writer and educator who’s worked as Grindr’s sex columnist and Playboy’s resident male sex writer and advisor. Follow him on Instagram and Twitter @bybobbybox. 

This post was written by a guest blogger, and all opinions and ideas expressed are that of the author. All ideas included are for educational and entertainment value, and do not constitute medical advice.


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