How To Anal Fist Your BF: Guide For Beginners

Anal fisting or fist fucking - ff for you shorthanders out there - is an intense sexual act that a lot of gay men love. It’s the act of receiving your partner’s or man of choice’s hand into your anus. If you’re getting fisted, you’re simply the fistee, and if it’s your hand doing the penetration, you’re the fister.

Kind of contrary to the name, though, the hand won’t be in a fist shape! That would be next to impossible even for the most experienced fistee. Some guys like to go very, very deep, and others may choose to keep it just to the wrist.

It can provide some of the most intense pleasure for the fistee and gives the fister a strong sense of control. The most important thing though is communication! You shouldn’t experience pain, but it can border on an excruciating experience. The average dude’s hand is likely much larger than any dick you’ve ever seen let alone taken, so there are a lot of key things to consider.

Preparing for fisting

Anal fisting isn’t exactly for the faint of heart. It’s considered one of the most advanced anal experiences. So you will likely have to prepare quite a bit if you’re new to this. You’ll want to get very acquainted with your anus if you’re the fistee because it’s in for a big stretch so you’ll want to keep that in mind.

If you’re a size queen, that’s probably what led you to fisting, but if your new partner has raised the idea to you, you might be diving into the deep end from the get-go. Either way, you’ll most likely want to douche and make sure you’re very clean. I’d recommend a lengthy dildo to warm up and ensure everything is all clear.

At this point, I’d also like to bring up how big of a role diet can play in this. Seasoned bottoms know, some meals result in absolutely zero chance of sexy time post-meal. Fisting sets that bar a lot higher. You will be opened up in ways you might not have ever come close to experiencing, and the feeling of fullness combined with the motions of fisting... can lead to some really awkward times!

You can go the extra mile by warming up, with or without a partner, by fingering your hole or using toys. I’d recommend working up from your average girthy toy to something with a rather large head, like a tapered butt plug or a monster dong that really stretches you out. When you’re more experienced, it can be a lot of fun to have your hole worked open by a trusted fister, but if this is your first rodeo, make sure you know your limits.

You can buy a few toys to really help get you warmed up, but my biggest suggestion is LUBE!! You’re going to want a lot of lube, lots and lots of lube. This isn’t the time to skimp on quality either. I’d go with a creamy, thick lube, over the silky, runny lubes you might use for regular penetrative sex. The reason I like thick, creamy lubes for fisting is because it gives a great visual queue to the fister, that you’re running low and need to relube, you’ll thank me later when you don’t have a dry fist up your ass!

(Fisting Cream) 

Positions to get fisted in

Now that your hole is ready, it’s time to get comfortable. Seriously, you don’t want to be in an awkward position to get fisted in. Think about it, you could cramp, tip over, twist, whatever happens, it would be while you’ve got some guy wrist deep (or further) up inside you. That’s a recipe for anal fissures and that is for sure the wrong AF abbreviation for this blog.

So to avoid having an uncomfortable conversation with a physician, I can recommend three ideal positions for getting fisted whether you’re a seasoned fistee or it’s your first time. Whichever you choose, I would also recommend having something for your hands to grab. Whether that’s a third guy’s cock or a stress ball, trust me, you’re gonna want a distraction at some point to help you past a hurdle.

The first position I’d recommend is doggy-style, all fours or face down and ass up. This position gives the fistee the ability to move more freely so it’s my go-to. If you need to ease the pressure, you can, if you want to go deeper, you can. This position gives the fistee a lot of control making the process a lot easier, honestly. Being in control will help ease up some of the stress of getting fisted for the first time, it’s like the equivalent of the cow-boy position if it’s your first time bottoming. It. Just. Works.

The next position I’d recommend is laying on your back on a comfortable surface like a bed or sofa. When you’re comfortable you’re more relaxed, and when you’re getting fisted, you’ll want to be as relaxed as possible. This position gives the option for the fister to watch for facial expressions and helps them gauge how things are going between your moans - or screams - of pleasure. I find this position can get a little tiring if you’re keeping your legs in the air, but you could make use of restraints to help keep you in position.

Last, and personally my favourite, would be fisting by way of a sex swing. Now, this is, by and large, the biggest investment, but it’s honestly, the best position for fisting, in my opinion. I think the dedicated furniture for sex really sets the tone for what you’re about to do. It gets you in the mindset for kinkier, more advanced sex. Sex swings often have built-in restraints or rests for your legs, so you really just get to lie back and experience the fullness of getting fisted without worrying about bunching sheets or moving the wrong way. Plus, when things really get going, the swing aspect can give the fister a lot of options to pleasure the fistee.

Fisting for all

Fisting isn’t just a gay or bi man thing, I mean there are tons of articles out there on vaginal fisting, so we know the heteroes are doing it, too... well other lady friends of course, as well. Just because you might not like being the fistee, doesn’t mean you wouldn’t like being the fister. There’s no closer feeling of intimacy than literally touching his insides, am I right?!

Lube will really be your best friend on either end of the experience. It makes the whole thing much more manageable for the fistee, and for the fister, I feel it would be all but impossible to squeeze a hand inside someone’s anus on spit alone. It’s a whole different ball game than other forms of penetrative sex.

There are even specially designed fisting gloves that are thicker than your average rubber gloves. These can be especially great for newbies to fisting as they get a lot slicker than skin which can make inserting the fist a lot easier on everyone. They also don’t absorb lube the same way your skin does, so you get more out of the product you’re using. Bonus points if they’re textured for added pleasure, just picture ribbed fingers teasing your prostate!

(Master Series Stuffer Fisting Hand Dildo)

You’ll basically want to re-lube any time you’re reinserting so you don’t have to worry about drying up. This is kind of a foolproof way to keep things risk-free! You might also want to keep an extra bottle of lube around just in case. You definitely do not want to run out.

Will fisting hurt...

Size queens might be more familiar with the aftermath of taking something large up their rectum, but if it wasn’t enjoyable - at least for some - people wouldn’t do it. You’ll be sore after your first session, probably after your 100th, too, but that’s to be expected. Your hole is getting a workout like it’s never experienced before! But fisting, no pun intended, should walk that fine line between pleasure and pain.

Sharp pain is a surefire sign of a full stop on the session. Any blood is also a massive sign to stop fisting for the time being. You don’t want to end up with something irreparable, right? So it’s important to listen to your body. Go slow, and make sure if it’s your first time that you’re with someone you trust. Even better if they’re experienced with fisting.

Communication while fisting, either the fistee or fister, is basically constant. Start with fingers to really relax into the moment, then look to work past the knuckles. The hand should be shaped with the middle and ring fingers pointing straight, the pinky and index fingers pointing straight but under your middle and ring fingers almost making a joint point together, with the thumb tucked under in the empty space. This will get the hand in its smallest circumference for entry! This hand “position” is basically the “fist” that you’ll take initially.

Once past the knuckles, a lot of the intense stretch on your rectum will reduce. I mean your wrist is smaller than around your knuckles, but you can work your way deeper. If you do go deeper the fistee will actually feel the forearm muscles moving, so for you muscle daddies, you can really rock his world. With the “fist” inside, digits can move slowly to really intensify the experience. The fister can really work the fistee like a puppet at that point and every movement will cause insane sensations for the fistee.

Again, though, there really shouldn’t be any “pain” if things go smoothly. That said, it’s definitely not unheard of for full insertion to take more than one try, let alone a session or two. So enjoy the process of truly working the hole, or having yours worked. Even three fingers can give the fister a lot of literal leverage for stretching the fistee.

Beginners and the experienced can make use of both hands, too, either to stretch more or faster, it can really up the intensity while keeping things safe. A newbie is probably not gonna get double-fisted, but two fingers from each hand moving in different ways will blow the

fistee’s mind! Using both hands is a great way to de-escalate from attempting to take the full fist, while still keeping the hole open.

The first time wasn’t the charm...

Everyone’s first fisting experience is different, whether you’re the fistee or fister, fisting is completely different from cock-based penetration. A dick is designed to get inserted, your head is naturally tapered, and the glans is usually wider than the shaft, all things kind of pointing to more or less successful first attempts. A hand is largely very different, from shape and size alone to the inner workings. Your cock has more flexibility and, even rock hard isn’t as firm as your boney fingers.

So, if your first attempt to get fisted doesn’t go as planned, the odds are kind of against you anyway, don’t take it too hard... sorry I can’t resist! As the fister, listen to the fistee, if they’re calling it quits, don’t be disheartened from trying again another time. Both of you can think of it as a goal to work towards, which will honestly make it much more fun in the long run anyway.

(Pjur Analyze Me! Relaxing Anal Glide Silicone)

If you’re really struggling, you can look for anal training kits that are specially designed to get your rectum used to stretching larger. These are usually made up of various butt plugs that increase in size, so not only do you get used to the stretch on the rectum, but also retain the fullness from the penetrative end of the toy. Ultimately, they’ll make you more comfortable with the whole experience, so I would recommend them whether you’ve tried to get fisted already or you’re preparing for your first time.

At the end of the day, anal fisting is about communication, pleasure, and, most importantly, LUBE!