Deep Anal Play

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How can I achieve really deep anal penetration?
Ben Harrison, Young, gender noncomforming hetero-flexible male.
Answered 1 year ago · Author has 119 answers and 282.9K answer views
Go slowly. Warm up properly. Start small and shallow. USE LUBE. NO SUCH THING AS TOO MUCH. (but you wouodnt want to be excessive and wasteful either.)
At first, once you're all warmed up and ready to go deeper, maybe start with a flexible toy. Flared base only. (Dont want a trip to hospital cos you lost it inside you)
If it's too hard and stiff, you wont make it round the bend at the end of the anus and start of the intestines. That's where it gets “deep" as people call it. Be gentle, and try to let your body guide the toy around the bend. Be VERY gentle. If it's not working, relax, and try agai
Go slowly. Warm up properly. Start small and shallow. USE LUBE. NO SUCH THING AS TOO MUCH. (but you wouodnt want to be excessive and wasteful either.)
At first, once you're all warmed up and ready to go deeper, maybe start with a flexible toy. Flared base only. (Dont want a trip to hospital cos you lost it inside you)
If it's too hard and stiff, you wont make it round the bend at the end of the anus and start of the intestines. That's where it gets “deep" as people call it. Be gentle, and try to let your body guide the toy around the bend. Be VERY gentle. If it's not working, relax, and try again later. If you push for anything during anal you're far more likely to injure yourself. The anal lining is incredibly fragile so exercise caution. Once the toy is round the bend, you're doing it! (Or if youre a guy you may struggle to get past the prostate. It still feels amazing, but when you have a large mound in the way what can you do).
Tldr: soft toy, lube, patience, start way slower.
Over time (especially if your partner is well endowed) you may want to try it with them. Make sure you talk them through it, it's your body and you would know how to do it safely. By the time your partner is able to go deep (unless this is a major fantasy of theirs) they will have passed their hardest and their penis will have softened a little bit. So it will go around the bend.
Related Questions (More Answers Below)
What is the largest penis that I can take in my anus?
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Stign Goossens, Cam Model, Web Master for www.JoeSixPackCams.com (2019-present)
Answered 1 year ago · Author has 285 answers and 144.7K answer views
You have to train your asshole to stretch it so it can take a big dick.
Exercise your anus first with your fingers and then with a small dildo. You Gradually can use a bigger and bigger dildo until you can take a monster cock.
Don't forget to apply lube for easier sliding in and out.
Even better is to have your girlfriend help you do these exercises. Or one of your mates from football practice.
What is the largest penis that I can take in my anus?
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Anal Depth Training: How To Do Deep Anal Like A PRO
Dainis Graveris
Updated: March 3, 2021
If you want to go deep from behind then this comprehensive anal depth training guide is what you are looking for!
There are only two possible explanations as to why you clicked on this article.
The first one: you have done your fair share of anal training, anal stretching, and anal dildos — and you are now looking for a new challenge.
The second one: you are not quite sure what anal depth training even is, but you are curious to find out. Plus, it sounds like something that you might possibly enjoy.
In either case, you’ve landed on the right page. Let’s jump straight into it.
Anal depth training is a sexual practice that involves inserting objects as deep into the anal cavity as possible. The goal is to reach and then get past the sigmoid bend.
Unlike stretching or fisting, anal depth play is only concerned with the length rather than the girth of the inserted objects.
To be fair, most people don’t. Depth training is one of the most extreme forms of anal play and is definitely a niche fetish.
So keep this in mind when learning how to anally masturbate.
The people who are into deep anal generally fall under two categories. 
On the one hand, we have the anal aficionados who have seen and done it all and are now looking for new challenges. 
On the other hand, we have BDSM enthusiasts. You often hear about dominants who order their submissives to probe deeper and deeper into their anal canal as part of consensual humiliation or power play. 
One thing that these two groups have in common is that both get a powerful kick out of pushing their bodies to the limit.
So, have you decided to give anal depth training a try? 
You’ll need these to get started: lube and a few long anal toys (however, you can always start with just one and see how that goes before getting more).
Just like with any form of anal play, you want to stock up on lube, and you can’t ever have too much.
As you will be using a special tool such as a Slink, an anal snake, or a depth probe, make sure that your lube is compatible with the material of your toy.
Remember: you should use water-based lube with silicone toys. 
While there are many anal depth training products on the market, these are by far our top choices. As a rule of thumb, you want a toy that’s long, slim, bendable, and has a tapered tip.
This is our absolute favorite depth training dildo. It’s extra-long, super-squishy, and features a tapered tip that’s perfect for exploring far up the anal canal.
Plus, it comes in five different sizes ranging from 11.5 to 23.5 inches of insertable length that should fit most body types. 
If you need something longer than 23.5 inches, how about this not-so-little fella?
Its whopping 40 inches worth of insertable length make it a great choice for more advanced anal depth players. 
Measuring at 19.5 inches of insertable length, Doc Johnson’s Kink In Deep Silicone Anal Snake is an excellent mid-sized alternative.
It is made out of soft, body-safe silicone and features a slightly ridged surface that ensures a secure grip and makes for some truly delicious friction.
Let’s bring in the heavyweights, shall we? SquarePeg’s Depth Probe Colon Snake is absolutely MASSIVE.
The largest of the three available sizes measures at 39.96 inches of insertable length! If you’ve got what it takes to get that up to your butt, you won’t be disappointed with this product.
When it comes to depth training, you should begin by following standard anal play protocol: give yourself an enema, sanitize your toys (learn how to clean anal toys), and make sure you are fully relaxed and warmed up. 
Don’t panic. The puborectalis sling1 is a powerful muscle that’s attached to the pubic bone and surrounds the rectum like a sling.
When you apply pressure on it, such as during anal sex, this muscle automatically contracts and closes the rectum.
Learning to relax the puborectalis sling through breathing exercises and repeated internal stimulation is the secret to effective anal depth training.
If you are a beginner, deep anal pressure is an unusual sensation that both your body and your brain are not accustomed to. At first, it might not even feel pleasurable but rather weird. 
Your goal with deep anal training is to learn to relax the body and breathe into the various internal sensations that you are experiencing.
Eventually, you will start to find this type of stimulation pleasant and even arousing. 
Once you get to your sigmoid bend, start applying gentle but persistent pressure — and don’t stop. It’s all very simple, but it requires quite a bit of time and patience.
It may take hours or even weeks before the sigmoid bend gives in and lets you pass through. 
Eventually, however, you will be able to not only get past the sigmoid bend but also start thrusting your toy (instead of just probing around with it). 
Always remember, though: be super gentle. Don’t force your way up, or you risk serious injuries. The key to success is persistence. 
Anal depth training is extreme. As such, it has more inherent health and safety risks than your standard anal practices. Here’s what you should know before starting your foray into depth play.
I will never get tired of repeating this one. Not only is your asshole more delicate than a vagina, but it also gets more and more delicate the farther up you go. 
That’s why you want to use obscene amounts of lube to make sure that you don’t end up with internal tears. 
You should expect some pressure and discomfort during your anal depth training. You might even get off on that. 
However, you should NOT be feeling any pain whatsoever. You will be going too far up your colon to take any risks.
Another thing to keep in mind is that while your intestines are very sensitive to pressure, they are not quite as good at sensing pain.
That means it’s possible to go a little too rough on them and not even realize it. So, keep things slow, steady, and gentle — and know when enough is enough.
A lot of the deep anal toys out there are made of porous materials such as jelly, PVC, TPE, and TPR. Stay away from those; they are impossible to fully sanitize.
You’ll be introducing your toy way too deep into your body to be taking any chances. 
The only 100% non-porous, body-safe, and bendable material is silicone. That’s what you want to stick with.
All anal toys should have a flared base to prevent them from being sucked up your butt.
However, this is particularly important when it comes to depth training. The toy will be going very far up, and the risk of sucking it in is real. 
“You want thin, soft, and extremely lubed toys. Buy a shower enema kit. […] Also, buy a lube shooter, […], and lube the hell out of yourself. Don’t be shy to get it d e e p inside of yourself.
Finally, lube the entire inner cheek of your asshole, I’ve found that sometimes when I’m ‘stuck,’ it’s because the toy is dragging on dry flesh, the damn inner cheek.
Have fun, and go slow. Try not to touch your dick if that’s what you’re working with, it might help you initially, but I find after I cum, I don’t want anything in there anymore, and it stops [the] play. If I delay that as long as possible, though, I can get up to 18’’ inside.”
“Wiggle: Because you’re trying to get a relatively firm rod into a curvaceous tunnel, you’re going to have to re-route the tunnel. Wiggling and rocking back and forth on toys can really help to get past that wall.
You’re basically trying to bend the toy (and yourself) just enough so that the head […] isn’t just ramming straight into a wall anymore. You’ll probably (and hopefully) get the most mileage out of this tip. Squirm, wiggly, rock, whatever it takes to bend yourself until it fits, but it should help.
The ecstasy trick: No drugs required! What I found from personal experience with depth training was that I was way more open (heh) to going deeper when I was really horny (especially so when I was right on the edge.) I’d take what I comfortably could inside of me, and as I got closer and closer, I would push just a bit harder, despite feeling like I couldn’t realistically take anymore.
Not only did it feel amazing going for those last few pushes, but in doing this, I could often take 1–2 more inches. The adrenaline really does help.”
Did you enjoy our guide on how to do deep anal? Let us know in the comments section! 
And, as always, feel free to share your personal tips and tricks on anal depth training, your all-time favorite anal depth probe, or anything else you think is relevant.
With over 2 year experience working in a local adult toy store Dainis has gathered quite a bit of experience about helping people find the best for their needs. He's also a top writer on Quora (7M views, 2.3K followers) and has written over 70+ guides on SexualAlpha. Read More
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“Pelvic floor with pubo-rectal sling”. Research Gate. https://www.researchgate.net/figure/Pelvic-fl-oor-with-pubo-rectal-sling_fig9_305726275.

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