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How To Train Your Anus For Mind-Bending Gay Sex

Your new Sex Ed teacher is here, and I’m serving you a hole first lesson.
Bobby Box
&
Sex Columnist
May 27, 2020
June 15, 2024
7
min. read
man in boxers facing the bed
Table of Contents

I was on Grindr before I knew I was gay. I mean, I thought I was gay, but I’d never dated or been intimate with a man before. So one night after a few too many vodka-Gatorades (don’t judge), I created a Grindr profile, complete with one—just one—photo of my headless torso, as most questioning men in the suburbs do.

Now, many years later, the app that pushed me to explore my sexuality is giving me the opportunity to do the same for others and, honestly, I couldn’t be more thrilled. Welcome to Gay Sex Ed, Grindr’s sex column for responsible, credibly-sourced sexual information for men who have sex with men (MSM).

When I came out, something I noticed straight out of the closet was the lack of legitimate sexual resources for queer people. This, on top of a sex ed curriculum that ignores queer people, means many of us have had to learn about sex through experience or word of mouth, which can be both dangerous and traumatic.

For the column’s inaugural entry, I thought it wise to choose a subject applicable to our current circumstance. Since sex with partners outside the home is prohibited, now is the time to be productive and train for the fateful day when you’re able to take a real life dick again. Fetch the lube, sweetie, It’s time to get your hole some exercise.

How to train your anus

The sphincter, like a bicep, glute, or quad, is a muscle and needs to be exercised in order to improve function and prevent pain. Think of it like returning to the gym after considerable time off. Your muscles are rusty, but after sticking to a regular training schedule, things gradually start feeling more comfortable.

In addition to making anal penetration more pleasureable, anal training can also help the body work toward larger toys, cocks, and other pleasurable forms of butt play, like fisting or gaping.

Training schedule

While there is no official schedule for bottom training, consistency is key since our holes are used to being closed tight for the majority of the day. Zoe Ligon, the “Dildo Duchess” and CEO of Spectrum Boutique advises that when you start training, you listen to your body instead of adhering to a strict schedule.

“Don't pressure yourself into a schedule that doesn't match up with what your body wants,” she says. “Awareness of physical sensations as well as bodily tension are key, so if you feel any rawness or see any blood, hold off and let yourself heal. Even if we take it slow, the rectum is delicate, and irritation/tears happen.”

Seeing red

Yes, unfortunately, even when taking all preventative measures, injuries can happen. The hole is a sensitive water sign.

“Blood, friction-y feelings, tension, cramping or clenching, and even mild discomfort should be taken seriously,” Ligon says. “Remember that you can eventually reach the colon with a long enough toy, so you must be cautious and gentle. When I’ve injured myself, it felt like a small discomfort at first, but upon completion it was very, very painful.”

If you see blood or experience any of these above sensations, stop what you’re doing. If there’s discomfort, try taking a warm bath with epsom salts for 10 to 20 minutes several times throughout the day, or use a warm compress. Drink plenty of fluids and eat fibrous foods to help make bowel movements less painful as you heal.

If the pain persists or worsens, consult a (preferrably sex-positive, queer-friendly) doctor.  

Lube up

Because the anus isn’t self-lubricating and the tissue is thinner and more sensitive than the rest of your skin, a quality lubricant is important. Silicone lubes (or hybrid water/silicone lubes) are a great bum-friendly option because they’re long-lasting, won’t evaporate, and don’t get absorbed into the skin.

I personally prefer silicone-based lubes since they have a similar texture to oil and are body-safe, but I should mention that these lubes cannot be used on silicone toys (basically, it just tries to liquify the device). “People love to use oils for anal play, and coconut oil is great if you're lubeless and needing a household alternative––just keep in mind that no oils are condom-compatible,” Ligon adds.  

Water-based lubes don’t have that same slickness, but a thick lube with a gel-like texture is a solid choice as it’s compatible with everything and is less likely to stain the sheets.

Necessary tools

There are thousands of toys and devices to choose from when prepping your pucker, but why not start with your fingers? They’re free, come in five different sizes, and can help you gauge what size and shape work best for your body before spending any money.

You can use dilation kits, which let you work your way up a series of toys with graduated sizes, or invest in a longer-term device like a prostate massager (linking to my personal fave), a dildo, or a butt plug. Again, you need to find your preferences in shape and size through exploration, since we all experience pleasure differently.

Whatever you do, make sure you purchase the items from a credible retailer, that the toy is made from body-safe materials, and that the toy has a flared base so they don’t get lost inside you (because your bum is a vacuum). We don't need any dildo emergencies in the hospitals right now!

Open wide

There is no such thing as too much lube, so apply it generously to both your finger/toy and your hole (for optimal comfort, invest in a lube injector to reach deeper in the anus), then slowly insert your finger or device until you feel even the slightest resistance.

“Tipping-in works much better than trying to insert something at a perpendicular 90-degree angle,” Ligon says. “That way you aren't ramming something against your sphincter and you're able to massage it open more gently. Once you're a little in, gentle swirling or side-to-side, up-and-down motions can help relax you further.”

When starting out, keep the toy inserted for roughly five seconds, remove it, and repeat 10 times for three sets. This will help ease your anus into the sensation of penetration at a speed and depth your body is most comfortable with.

If penetration isn’t your preferred training method, you can wear a butt plug for an extended period of time to get accustomed to the fullness of penetrative anal sex. However, it won’t exercise your sphincter the same way that active play with a toy does, which is more similar to the sensations of anal sex with a penis.

“Just be gradual in everything you do,” Ligon advises. “Some people require less warm up than others, so noticing sensations and relaxing matter a lot more than the specific length of time you play for. The more you do any sex act, the more awareness you'll have over the nuances in sensation. That is a more important skill that will lead to more pleasure than being able to take the biggest toy ever and going for marathon anal play sessions.”

Upsizing

Your body will tell you when it wants a bigger toy, Ligon refers to this sensation as a bum’s “size craving.” To test for a possible upgrade, try inserting a nail-trimmed finger alongside your toy and gauge how that feels. If you take it easily, that’s your green light to size up, queen! But if your body is resisting, you’re still in the yellow and should stick with your current toy.

“I personally discourage people from using inflatable toys because that's a great way to over-do it and injure yourself,” Ligon cautions. “I have seen some large toys in my lifetime, and as a large toy enthusiast myself, I personally knew when I hit my limit because I immediately yelled, ‘get this thing out of me now!’”

Have fun

Whatever your reason for anal training––to take a bigger cock or just enjoy anal penetration more––the rules are simple: use caution, start small and slow, use more lube than you think, and be consistent. If you can do that, you’ll be a cock destroyer by the time we’re allowed  inside each other again.

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