How to Train for Fisting

Hello! I’m Alexander Cheves, a sex writer, worker, and educator. Friends call me Beastly. My new book, My Love Is a Beast: Confessions — an erotic memoir — is available now everywhere books are sold.

On this blog, I answer sex questions, especially about topics you might not find covered in mainstream places. No fetish is too taboo and no question is off-limits. I focus on safety, sex-positivity, de-stigmatization, and risk reduction.

If you like what you read, please support this blog on Patreon — every dollar you donate helps me run this site. Thanks to censorship and sex panic, WordPress will not let me monetize this site directly with ads. This blog is 100% supported by donations from readers. Please help me keep Love, Beastly going strong.

Dear Beastly, do you have any tips for someone starting to get into fisting and anal stretching? I’ve already started to use butt plugs to start, what next?

Hi future fist pig,

I don’t know what most people do, but here’s what I did. After I could comfortably take medium-sized butt plugs, I hunted on hookup apps (Grindr and Scruff) for an experienced fist top to give me my first hand. This was unsuccessful. In Los Angeles, where I was living, few people seemed interested in playing with a first-timer. I promised myself then that I would be welcoming to beginners once I learned how to fist, and now I really enjoy ass-training and fisting beginners — these are some of my favorite client experiences as a sex worker.

In the end, I met someone at a gay club. Predictably, I needed in-person chemistry — not a spammy hookup app — to make my first fisting happen. I knew enough about fisting to have an idea of its risks, and I respected it, and I assumed I would need several sessions before I was able to take a hand. That’s not what happened — I was in the right headspace, he was skilled, and with the help of poppers, I got fisted that very night.

But I got lucky. In hindsight, I wish I had asked him more questions — I did not know his experience level or whether or not he was doing it safely. He fisted me with no injury and I really enjoyed it, but in hindsight, I was grateful to have gone home with the right person.

Don’t depend on luck. Beginners should be as informed about fisting as they can be, and they should seek playmates who are knowledgeable and experienced. It’s okay to ask how many years someone has been fisting. Every beginner fistee should make it their goal to meet an experienced fist top and should be rigorous in their questioning. The risk for injury is simply too great to do otherwise. Fisting is fun, but unsafe fisting can send someone to the Emergency Room and result in long-term — even permanent — injury. You must respect fisting in order to enjoy it. The same is true for beginner fist tops: they should first play with experienced bottoms (I know many skilled boys with big hungry cunts who love being a top’s first fisting). In all risky sex, from bondage to breath play, novices should learn from experts.

You are ready to start looking for someone. Your work from this point is simply finding people. In some big cities, you can find fisting parties that are friendly to beginners, and of course, the big kink events in the U.S. — Folsom Street Fair, Dore Alley, Pig Week, Fist Fest, IML, MAL, and so on — can be wonderful places to find playmates, make friends, and discover your community. These events are vital and must be protected at all costs because they connect people like you to others and keep our community safer. Traveling to a kink event can be expensive, but I think every kinkster should make an effort to visit their closest one more than once. I believe the same for kinksters across the world. If you’re in Europe, try to make it to Folsom Europe in Berlin or any other kink event in your country. (Visit fistrik.com to see if there are any fisting events happening in your part of Europe.)

There are also private fisting Facebook groups, fisting websites like AssPig.com, an active fisting community on Twitter, and smartphone apps like Reegür and Recon that can connect you to others, though I maintain that digital spaces (apps, social media, and so on) are not substitutes for in-person gathering. Leather bars are precious and imperiled, and they deserve your dollar more than Grindr, which is owned by a Chinese video game developer that doesn’t give a shit about the queer community beyond its ability to monetize us.

Once you can take plugs that are close to the size of your hand, your next step is to find a real person — someone who will be patient, take care of you, go slow, and gently stretch you out. When you get past his knuckles and the suction of your butt pulls his hand in, you will be very overwhelmed. Take deep breaths, try to slow your breathing, count to thirty, and in your mind, visualize your hole opening. Happy first fisting.

Love, Beastly

2 Comments

  1. Are you ok? The reason I ask is your column usually appears like clockwork, perhaps I’m missing something. I enjoy your blog, your thoughtfulness as well as how willing you are to share your knowledge. Hope all is well. Love

    Like

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