How To Fist Myself

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How To Fist Myself
Between sets at the gym, I explained to a friend what fisting is. He did not believe me. I demonstrated: my hand, balled in a fist, punched slowly through the air, a gentle six-inch thrust, turned slightly at the wrist, and pulled back. The last time I did this in a man’s hole, he roared into the pillow — that lovely, otherworldly animal growl of pleasure.
I’m not a “pro” or internationally famous fister. But I love it, and that’s why I’m writing this. Because you don’t have to be a pro. There’s no level that qualifies you to talk about or enjoy your fetish. In a kink that requires training and skill, practitioners sometimes get bogged down in a competition that doesn’t exist, in comparisons that idealize “pros.” Everyone starts somewhere. It’s great to be a beginner.
The only thing you need is the hunger — that can’t-look-away tremble when you watch fisting videos online. Ready to try? Click through for my best tips on taking a hand.
My name is Alexander Cheves, and I am known by friends in the kink and leather community as Beastly. I am a sex-positive writer and blogger. The views in this slideshow do not reflect those of The Advocate and are based solely off of my own experiences. Like everything I write, the intent of this piece is to break down the stigmas surrounding the sex lives of gay men.
Those who are sensitive to frank discussions about sex are invited to click elsewhere, but consider this: If you are outraged by content that address sex openly and honestly, I invite you to examine this outrage and ask yourself whether it should instead be directed at those who oppress us by policing our sexuality.
For all others, enjoy the slideshow. And feel free to leave your own suggestions of sex and dating topics in the comments.
Hungry for more? Follow me on Twitter @BadAlexCheves and visit my blog, The Beastly Ex-Boyfriend . Photo by Jon Dean.
You don’t learn how to fist by taking a fist. You learn with small butt plugs that gradually get you comfortable with the feeling of stretching your anal sphincter (your hole). 
You must get accustomed to this feeling and enjoy it before you work up to larger insertables. And then — and only then — can you start playing with fingers. You may find — as I did — that the stretching process can be more fun than the actual fisting. I found a massive love of toys (or a love of massive toys) along the way.
Pro tip: Purchase a small, smooth, teardrop-shaped (or rocket-shaped) butt plug no larger than an inch in diameter. Lube it up with tons of lube, slide it slowly in, get comfortable with the feeling, then pull it slowly out. In, and out. Again. Steadily build speed. This is way better with a playmate.
Being a good fister requires knowledge of different chemicals and compounds and how they interact with each other. Insertable toys can get very expensive, especially larger ones, and you want to pay for premium materials.
Smooth, soft, high-grade, premium silicone comes with a hefty price tag, but it’s worth it. You should avoid cheap, hard, plastic-feeling toys made out of materials like TPE.
Since you’re paying money for good toys, use lubes that won’t damage them or limit their longevity. Silicone compounds tend to bind or break each other down, so don’t use silicone lube with silicone toys unless the manufacturer explicitly states it’s safe to do so.
Do research! Find lubes explicitly made for toy play, contact the manufacturer, and always do a “spot test.” Rub a small amount of your desired lube on the base of your toy and leave it for a few hours to see how it reacts. If a chemical reaction happens — an eroded spot or bubbling up — that’s not the lube to use.
Pro tip: When in doubt, water-based lubes are best for toy play.
There’s the old-school classics like Crisco and J-Lube, but recent years have seen an increase in lubes made explicitly for fisting. Grunt Grease from Fort Troff, various lubes from the English brand FIST, and K-Lube — similar to J-Lube except that it’s made for humans (J-Lube is a veterinary lube used for birthing cattle) and way easier to clean — are all great options.
Pro tip: I use J-Lube. Different fisters enjoy different consistencies — I like my J-Lube thicker, less runny. Adding different compounds to the mixture produces different effects. Clove oil, for example, softens the skin and minimizes inflammation and irritation, and has a nice smell.
This is for everybody. Everyone with a kinky thing: Stop using porn as a the measuring stick for skill. This includes both “amateur” and professional porn.
Porn is wonderful, but it also skews to the advanced skill level. You don’t get in front of a camera to do something unless you know how to do it well. Which means we, the viewing public, rarely see the failed attempts or hours of training.
I’ve worked on professional porn sets and can assure you all the preparation time, messes, stretching, and training still happen, even and especially at the “pro” level. It happens before, during, and after the action, and gets edited out of the final product.
Pro tip: Don’t watch too much porn when you’re starting off. Form your reality around your own experience first.
The kinkiest, most hardcore fister will be a beginner to a new kink. Because we’re all beginners to something we haven’t done.
Pro tip: Being a beginner and discovering a new sex practice is the best part of the journey, and one you’ll never live again.
The stigma against fisting is real. Guys who aren’t into it may be repulsed by it. In the kink community, fisting is not a divisive or uncommon practice. Kinksters (kinky people) may debate the ethics of kinks like “race play” or rape fantasy, but fisting? No one bats an eye.
That’s not true for the outside world — for guys you do not meet in kink-friendly spaces, guys you meet in bars, on Grindr, or at the gym. I’ve been blocked countless times by would-be hookups when I answered their question: “So what else are you into?”
Pro tip: Don’t seek fisting playmates on mainstream platforms like Grindr. Look up apps like Recon or, better yet, go to your nearest leather bar or fetish store and ask the people there if they recommend any local fisting gatherings or online communities.
You can’t immediately jump into Olympic diving without training. Consider fisting Olympic-style penetration. You don’t dive in overnight.
All sports have risks. As with all sports, there are necessary steps you must take to minimize risks. Stretching and training your body doesn’t come without risk, especially if you go too fast, but you’ll be surprised at how supple your skin is and how much you can do once your train your muscles to relax.
Pro tip: Fisting happens in the mind, not the body. We tend to tense our muscles when we experience new and uncomfortable sensations. The journey of fisting is training your body to breathe, relax, and enjoy the sensation of your body relaxing and opening. 
I was horrified of fisting when I first saw a video. That horror morphed into curiosity. Years later, I accepted the fact that I was into it, and had to try it. But that fear has never completely gone away, and that’s part of its eroticism. If something scares me a little bit, I know it’s an erotic trigger.
The feeling itself is overwhelming, uncomfortable, and can be very intimidating. That’s the whole point. The vulnerability of working and exploring the limits of your pleasure and your body with someone is powerful. On the other side of that nervous threshold is the most intense pleasure my body has ever felt.
Pro tip: Never be vague or dishonest about your experience level or how you’re feeling. If you’re scared but game to keep trying, tell that to the person you’re playing with. Fisting is a two-person job. If you’re playing with someone you like, they can help you through that fear if you have established trust with them.
While the infection potential of gloveless fisting is disputed among fisters, you should definitely start with gloves. Not only do gloves create a barrier blocking fluid contact, they also protect the bottom’s body from germs and other unpleasantries that may be on someone’s hand. That said, you should wash your hands and forearms thoroughly before every fist session.
Tops: Your fingernails must be shaved down to nubs. What might feel like a barely-there sliver of fingernail to you will feel sharp when your hand is inside your playmate. Fingernails can hurt — and even tear and injure — the delicate skin of the rectum and colon. This is why you must wear gloves.
Pro tip : Use gloves made of nitrile, which is just as strong and protective as latex. More people have latex allergies than you think, and you won’t know you’re allergic until your butt feels like it’s on fire. 
It took multiple attempts before I got a hand in.
Pro tip: Start with a good toy play session and see how big you can go. Don’t put “fisting” on the agenda or work to that goal in your initial sessions. You’ll know when you’re ready to try.
Seriously. Fisters love talking about fisting. Everyone claims to have the perfect lube formula (I’ve met many guys who are convinced their formula is the best — only one was good enough to adopt as my own). Everyone has toy recommendations, buddy referrals, and so on. We have a pretty tight-knit community.
Pro tip: If you’re in a small town, create a profile on Asspig.com .
Talk to him about your skill level. It’s perfectly acceptable to question someone’s skill level, ask for videos, ask for references (from guys he’s fisted), and so on. An amateur fister who claims to be a pro can hurt you. You want to build confidence and trust with this person.
Pro tip: Referrals might seem awkward, but if you want to do this, someone needs to train you. If someone can refer you to a good playmate, reach out to them. 
Best way to avoid injury? Respect your body’s natural limits by playing sober. Playing drunk or high masks your ability to detect pain and know when you’ve had enough, and you can wear out and even injure your body this way.
Many guys start fisting on drugs, because drugs make fisting easier. They mask the sensation of pain and relax your body. While drugs have understandable appeal for all kinds of sex (not just fisting), masking pain is problematic, since pain tells you when you need to stop.
When you’re new, it’s good to train sober so you know how it feels naturally. It will take more time and more effort without substances. That time and effort is worth it, at least until you build up some skill.
Pro tip: I don’t count poppers — those amber bottles of “video head cleaner” or “fingernail polish” (wink, wink) consisting of various alkyl nitrites (or whatever’s in them now) that became a gay sex staple in the ’80s.
Dildos are far from the best way to train your butt. They’re essentially cylinders that widen from a narrow taper. Cylinders open your hole and keep it open at the same dilation as they slide in and out, while a butt plug constantly forces your hole to close and open around a rounded object, which stretches and trains the muscles in your sphincter (think: kegel balls).
Pro tip: If you enjoy dildos and think they’re fun, don’t buy those “realistic” dildos found in novelty shops — the ones modeled after famous porn stars. Most of these are way too hard for ass play. Seek soft, spongy, cushiony dildos from manufacturers that specialize in anal toys.
You probably have a shit phobia. Ask most beginners what terrifies them the most and they’ll say how they are terrified of “not being clean.”
It’s a butt. You can clean for hours and will never eliminate all traces of fecal matter from your rectum, and you shouldn't try to. It’s not safe or healthy to overclean down there.
Talk about your body, your diet, and your cleaning regimen with other fisters. Talk about using the bathroom. Ask for tips, tricks, and suggestions. Everyone who fists must get comfortable around these more intimate, messy realities of our lives. Eventually, you will reach a point where you are less afraid of the body and how it works.
Pro tip: A daily fiber regimen like Metamucil will make your cleaning process easier. Trust me.
If you’re not enjoying your initial sessions, cool it. Even if you’ve been fisting for a while, it’s good to take frequent breaks — and sometimes necessary. Give your butt a rest.
Pro tip: I frequently go on sex breaks to recenter, rediscover what I like, and focus on parts of myself that need my attention. The journey of relearning fisting and retraining my body is different and rewarding every time.
No, you won’t become incontinent — not if you fist safely and correctly. No, you won’t be unable to have regular sex ever again. No, you won’t permanently “destroy your butt.” Skin is elastic and supple. It stretches. You might require some healing time, but your butt will shrink back up and work the same way it worked before. You won’t be reduced to diapers — unless, of course, you want to be and that’s your thing (it is for some people).
Yes, fisting over time does result in a degree of body modification, so if you want the tightest hole in America, don’t fist. Our culture tends to conflate tightness with virginity and virginity with desirability. I call bullshit on that antiquated “virgin glorification” ideology and think used, skilled, experienced bodies are incredibly sexy. If anyone is seeking an ultra-tight hole, they can seek someone else.
Don’t listen to the fisting myths made to scare you. Listen to real fisters.
Pro tip: You’re allowed to set your own limits. Not everyone is into deep fisting — I’m not. Not everyone is into punch fisting — but I am. I set a depth limit, because depth scares me, and because I don’t know how to do it yet. If I ever go to that point, that will require training with someone I trust deeply. Only do what you want to do, and don’t feel pressure to enjoy your kink any differently than the way that feels right to you.
Pro tip: Don’t spend hours. If it’s not happening, or if you can’t get clean, set a time limit after which point it’s time to stop. Clean up and go watch Netflix. Don’t force the body.
You can communicate wordlessly and show signs of fear and pain — and intense pleasure — through gaze. If he’s paying attention and keeping eye contact with you, he’ll likely know how you’re feeling even when you say nothing.
Communicate as much as you need to, but keep in mind that real, wonderful fisting happens when words stop, when you lock eyes, and when your bodies (and your body language) take over. A good fisting session tends to slip into silence, a mental and physical wonderland of gasps and moans and roars and breathing. This is when the pleasure and beauty of fisting happens.
Pro tip: A lot of beginners start on all fours, doggy-style. Try a sling. Relax. Lie back. Eye contact is everything.
Meditation practices can help you train your breathing, “check in” with your body, relieve stress, and make yourself relax. Not only is meditation a great idea for juggling the stresses and pressures of daily life — it also helps in the handballing (fisting) department.
When I get fisted, I lock eyes on the man opening me up and retreat into my body. I shut off my head and scan down through my body, from the top of my head to the tips of my toes, relaxing my muscles and focusing on the sensation. I learned this through meditation.
Pro tip: Guided meditation apps can help you get those glorious 15 minutes of de-stressing you need.
I’ve had better sessions with less-experienced guys I liked than with seasoned pros who I simply didn’t click with. Fisting is one of the few kinks where experience level matters less than chemistry. You need to like him a little bit. He needs to like you a little bit.
Before you play, talk. Get to know each other. It’s hard to be more intimate, more vulnerable, with someone else than when their hand is inside your body. Fisting is extreme intimacy.
Pro tip: If you find someone who’s ready and willing to try fisting but has little experience, this isn’t a deal-breaker. You can learn to work together and build up to fisting by planning regular sessions, communicating, and going slow. I recommend reaching out to someone with experience to come over and coach you both through a session together.
There are various important organs and tissues down there. It helps to know the general map of your body.
Pro tip: Read the technical fisting books I recommend (see next slide).
There are some fantastic fisting how-to books written by true pros that I highly recommended. Here’s my top three:
Pro tip: All these are easily found on Amazon.
A big part of sex — particularly our “nontraditional,” kinky kind — involves handing over some control. Handing over control is beautiful and powerful and frightening to many people. When you’re the receptive partner in sex, the “surrender moment” comes when you get scared.
Your playmate is building speed, then suddenly a multitude of thoughts rush into your head: “Am I clean?” “Will I get hurt?” “Can I take it?” This tension in your mind will result in tension in your body, leading to immediate muscle tension in your ass. You’ll clench, which will result in true, legitimate discomfort, and this will make sex uncomfortable, and may even need to stop. 
Everyone comes to this moment. Don’t feel bad when you do — it’s part of the journey. When this moment comes, practice letting go. Your body is soft putty in your playmate’s arms. Your butt belongs to them.
You’ll come to many moments like this when you fist, moments when you get scared, where it feels like they can’t go any further. If they are good at what they’re doing, they will know where you are and guide you through these moments, but you have to trust them. You have to surrender.
Pro tip: You can practice this moment in sex years before you start training for a hand.
If you’ve never heard a fisting orgasm, I’ll describe it: A guttural roar from the lower world where your soul runs with the dogs at night. It is a sustained, drawn-out howl with peaks and valleys, generated from absolute surrender and pleasure. It’s a beautiful, almost frightening thing to witness.
Fisting rests on the delicate line between pain and intense pleasure, so the orgasms are appropriately intense and agonizing in the loveliest way possible. Once it’s over, that’s it — you’re done. It’s time to come out from that headspace, wrap your arms around the person who delivered you there, and rest.
I cannot get to that place without opening my mouth and letting the sounds come. Few people can. If you need help slipping into that headspace, roar. Moan. Respond in noise to everything you feel.
Pro tip: Turn on some music — classic fisting music has heavy, trance-like bass — if you don’t want the neighbors to think you’re being murdered.

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In today’s simultaneously sexual and sex-shaming culture, it can be hard to find clear, accurate information about sex and sex acts—particularly sex acts you do with yourself, like masturbating and fingering yourself! In this guide, we’ll provide clear, no-nonsense information on how to finger yourself. We’ll go over what it is, how to do it, and answer all the common fingering questions.
Note: this article is primarily aimed at those with vaginas/vulvas, although there is a section on anal fingering at the end of this article that of course applies to everyone. We acknowledge that not everyone who has a vagina/vulva identifies as a woman, so we have made an effort, where possible, to describe via genitals (i.e. “people with vulvas”) as opposed to gender (i.e. “woman”).
The term “fingering yourself” doesn’t necessarily mean the same thing to everyone. When most people say “fingering yourself,” they are referring to penetrating the vagina with one or
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