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TUTORIAL: Skydevil’s Ass Fisting Basics

FISTING refers to the adventurous art of hands-on exploration – whether it’s the brachioproctal adventure in the booty or the brachiovaginal escapade in the vagina. Double the hands, double the fun, known as Double-Fisting! It’s an intense yet thrilling play, demanding patience and practice for maximum pleasure and safety.

Your Tutors

For this lesson, I’m thrilled to introduce Skydevil as our guest tutor – a seasoned expert in both theory and practice. Fisting takes on almost religious vibes for our guest. Together, we’ll navigate through this lesson with passion and expertise.


he/him | Gay | Switzerland


Fisting can be everything – tenderness, gentle indulgence, meditation, or even boundary-pushing ecstatic bliss. What it becomes is solely up to both of you!

Take your time, no rush! Set aside a few hours with an open ending; Fisting shouldn’t be a quickie or a stressful exercise. There’s no specific goal, except savouring each other. The aim isn’t solely to get a hand in the booty; if your partner is tighter or less relaxed, there are plenty of other hand-and-booty adventures to explore.

Always communicate with your partner from the start, before and during. Share your desires, thoughts, and sensations. Build trust – that’s the key to relaxation and soaring together.

Geography of the Booty

Before every journey, it’s wise to check the map ahead of time. I know, in the age of GPS, it’s considered old-fashioned, but for Fisting, there’s no navigation device. So, it’s not just about knowing your partner; familiarize yourself with booties and their anatomy for a smooth ride.

Fisting GPS

In the realm of Ass-Play and Fisting, we’re primarily engaging with the sphincters—yes, there are two rings—and the anus, the lower section of the rectum, which, in turn, is the final segment of the entire colon.

If we’re picturing this as a journey, check out this schematic of the colon; it’s not a straight, wide highway through the desert. The path is winding and full of folds. And even though everyone’s anatomy is similar, it’s not identical. So, take it slow, embark on the exploration, and feel your way through this vast tunnel.

Given that the colon is anchored to the back abdominal wall near the spine, the bottom’s position matters. The doggy style should really be called the pot-bellied piggy style. In this position, the colon has ample room to unfold. Conversely, lying on the back has gravity pressing the colon firmly, creating a more compact arrangement.

For beginners, starting in the doggy style is recommended. This way, the bottom can control penetration with gentle movements forward and backward. However, in general, we always suggest trying out various positions yourself. You’ll notice that lying on your back with knees to chest straightens the curve from the rectum to the sigmoid colon, facilitating a deeper entry into the pleasure cave.

Exploring the depths of caves is undoubtedly thrilling, but the stop sign we’ve set has an anatomical reason. Going further there compresses the diaphragm and displaces the lungs. It not only sounds unhealthy; it is!

You might wonder why Ass-Play and Fisting are so stimulating or why, as a bottom, you might struggle to hold back the urge to pee. Well, that has its anatomical reasons, among other factors.

Just look at how close the prostate and bladder are to the play cave, with only a small amount of soft tissue in between.

In general, it’s worth mentioning that the booty is much tighter than the vagina. Understandable, considering it’s an exit for the little brown ones, not babies. Also, it’s “drier.” So, using plenty of lubricant is highly recommended. Don’t skimp on lube! When you start teasing the booty, try incorporating a good amount of lube inside. And when you’re greasing up your hands, remember, it’s not the palm but the back of your hand, especially the knuckles, that will make contact with your play partner’s insides.

Safety & Risks

Even Fisting has its health risks. So, here are a few tips on how to minimize them.

Rough and forceful actions during Fisting can cause internal injuries in the anus, leading to severe pain. In extreme cases, it may even result in perforation of the colon, which can be life-threatening. Explore the pleasure cave with patience, gentleness, and ample lubrication.

Like many sexual practices, Fisting poses the risk of sexually transmitted infections. Infections such as gonorrhea, herpes, and genital warts can be transmitted through contact with skin and mucous membranes. Using gloves and ample lubrication significantly reduces the risk of infection! Infections with Hepatitis C and HIV are also theoretically possible.

We advise against using numbing lubricants, as pain can be a clear indicator that taking a break or discontinuing the activity would be better.

Once again, we’d like to emphasize the importance of being careful with the sphincters. Mechanical damage to the sphincters can lead to incontinence. Even if we have readers on Kinkfinity who are Diaper Lovers, it’s not everyone’s cup of tea. You can read more about it in our “You Ask – We Answer” article.

My Advices

for Fisting Tops

Address the bottom’s needs. Learn what they desire, their fears, preferred movements, and what you’d like to try on them. Discuss speed, pressure levels, and whether you both want to explore new things.

Start slowly with a gentle massage, warming up and relaxing the muscles. Massage around their opening, gently stretching with 2 + 2 fingers. Fill the opening with some lube. Take ample time for this foreplay.

It’s about enjoyment, not breaking records. It doesn’t always have to be the whole hand or fist. I often fist tight holes for an entire night with 2+2 or 3+3 fingers, stimulating the inner sphincters around three-quarters inside where most nerve endings are, making it highly sensitive. Evenings like these can be a lot of fun.

Being stimulated in the right place is the hottest, but everyone experiences differently. Explore your hotspots together.

If you’ve passed the knuckles at the sphincter, don’t stop; go 1.5-3 cm further. That’s the vestibule, the lower chamber. Let your partner relax briefly before proceeding.

For relaxation times, follow the rule of a minimum of 3 breaths.

Feel what your partner’s insides want and fulfill those desires. If they try to push you out, yield. Always play with the booty, not against it.

The fistee can also actively try to envelop your hand with their booty: Press your hand against/into their opening comfortably. Your partner takes a deep breath, slightly lifting their pelvis (almost automatic), and you follow their hand with the movement. Then, as they exhale, they push their booty onto/over your hand…

for Fistees

The sphincter, as the name suggests, is a muscle that can be trained, stretched, and controlled like any other muscle. In the beginning, it’s best to do this training with toys on your own.

Warming up is crucial, and it can be integrated into your dates. You can also engage in some self-play while cleaning and afterward.

For stretching, conical dildos and plugs work best. I recommend high-quality, soft silicone dildos.

Not everyone who calls themselves a “fister” can actually fist well from my experience. Try to find someone you truly trust, who enjoys playing and caters to your needs. Especially when it comes to making yourself fistable and accommodating a full hand for the first time, it’s advisable to play with a regular partner. Trust brings calmness to the game and to the body.

Hey, if you're cruising on KINKFINITY, you probably know I'm the master of this fetish blog. BDSM isn't just sex for me; it's a lifestyle I've embraced for over 25 years. Along the way, I've met some fantastic kinksters—some dropping by my massive 200m2 dungeon for parties, others for days or weeks, and a few as 24/7 long-term slaves. Swing by my Bluesky account for more:

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