Why Does Anal Sex Hurt? Common Mistakes and How to Avoid Them

Why Does Anal Sex Hurt? Common Mistakes and How to Avoid Them

The stigma around anal

There’s a pretty unfortunate misconception surrounding anal sex: that it’s supposed to hurt. Many people try it once or a few times, feel great pain and discomfort and come to the conclusion that anal play is simply not for them. Even worse is some push through that discomfort and pain in sake for their partner's pleasure.

I've had several partners that share the same story when I ask them about anal: “I tried it with my ex and I hated it” I ask why? “Hurt like hell”. The fact that this issue is so widespread shatters my heart because with some anal education many couples could be having the best sex of their lives. Instead they toss it to the side and say that anal is for the extremists of sex.

Unfortunately the majority of people's introduction to anal comes from porn or a partner that is uneducated on anal pleasure. The porn industry only shows the part where pornstars take the biggest of toy/dicks with aggression. They completely dismiss what it took for that pornstar to get to that level of pain free anal. Many guys believe that all they have to do is go slow with their penis and anal will be pleasurable for the receiver. I am here to help both men and women not only tolerate anal but love it.

The mission

My mission is to have those who had bad first experiences with anal to give anal another chance. To understand the prep, mindset, and discovery it takes to fall in admiration for anal play. I wish this guide’s knowledge is relayed to loving partners and friends with the same struggles. I've educated and helped many people in person on how to make anal painless and a great joy and now I am ready to share my personal tips and past mistakes on a platform that can reach more struggling people.

Different from other anal guides

Many guides tackle the common mistakes but fail to go into detail of the actual process of executing the tips they give. Here I'll provide a personal education from mistakes I've gone through and tips for making anal work after assuming it was supposed to hurt for years. Anal can be enjoyed by both men and women both autonomies support anal pleasure greatly.

A little background to how I discovered anal play

Around 10 years old was when I first started anal play. At the time I didn't even know what even masturbation meant. I had the same curious troublemaker mindset as any other 10 year old boy, except that curiosity started to leak into discovering my ass. I found myself in the bath unconsciously rubbing my anus lightly. I then thought what if I were to put a finger up there. It was uncomfortable but I was intrigued.
I thought about putting one of my room toys in my ass. First it was nerf bullets then it quickly spiralled to bouncy balls, hex bugs, and really any small object that wasn't sharp. I then would see how many of these small objects I could fit in my ass. This was my first experience of pleasure through anal stretching. I now see how fortunate I am to not have an embarrassing visit to the hospital since the ass can act as a blackhole for unflared based objects.

Next was klismaphilia, the pleasure of using enemas. I would squeeze 4-6 water bottles of warm water up my ass and see how much I could take. This is very dangerous as it can cause a big imbalance in your electrolytes.

I then wanted to see how much I could stretch my anus. I used different sized hairbrush handles and that's when I discovered prostate play. If I just hit this funny little spot it would feel really weird yet damn good. Using the hairbrush handles always came with both pain and pleasure, so I assumed that anal was supposed to be painful as well.

After years of putting the weirdest things up my ass, I was ready for a sex toy at 17 years old. The issue was I still lived with my parents and sending a sex toy to my house was too risky. I was too scared to buy a sex toy in person as well. The answer…Amazon Hub Lockers ;) My first toy I bought was “The swiss army knife of prostate toys”, had it sent to the locker and got a great high from the success heist. I thought I was buying a toy. Turns out, I was opening the door to an entirely new world. Since then I've bought 50+ sex toys, can stretch my ass to pornstar levels painfree, and had mindblowing orgasm from anal play.

Ready to rethink anal? Let’s get started

Many years of failed anal sessions,experimenting, and researching has led to finding what works. Here’s how you can take anal from a “not for me” thing to “anal is the taboo we can’t leave out of the bedroom”.

Creating ideal conditions to getting started

The most common mistake to introducing anal sex/play into your life is deciding to introduce it with another person. Your first time is something that needs to be slow and takes practice. It requires you to go at your own pace and see what sizes you can handle. The majority of people will not be able to take a dick/full sized dildo without pain for their first time.

Cleaning: 50% diet 50% using the right amount of water

The rinse:

First before flushing out anything, go to the bathroom and empty yourself out naturally. Now that that is done, here's how to wash out. For most anal sessions you just need to clean out the rectum. which is the final 5 to 6 inches of the large intestine. Cleaning beyond that only makes sense if you are playing with massive toys or doing anal for multiple hours. Therefore you only need a little bit of water to clean out. Going beyond the rectum with water will disturb unformed waste in the large intestine and create an unwanted mess 10-20 minutes into your anal session. Due to the delicate walls of the rectum having any shit left in your rectum moved around quickly from toys or a dick will make anal painful. If you are dirty stop and rinse out a second time.

This is where enema bulbs come in, enema bulbs are cheap and often can be found with anal training kits. They hold the appropriate amount of water so you don't use too much water, I personally use 3/4th of a bulb. If you are going to use a plastic water bottle, fill with warm water all the way up so there are no air gaps, air in an enema will cause bloating. Push water into your rectum until you empty the bottle just above the top of the water bottle label.

After you fill your rectum with not too much water immediately empty yourself over the toilet. Stay there for at least 5 minutes as sometimes there's a delay to shooting out the last ounces of water. If you have a good diet where your shit is solid most of the time one flush is enough. If you have softer shit you may need a second flush out. Just make sure you got all the water out from the first flush to avoid having too much water.

Diet:

Having a good diet where your shits are solid is the quickest and easiest way to make sure you are clean for anal play. On the days I have solid shits I often don't even need to do an enema as the rectum does a good job of cleaning itself with the right amount of fiber in its system.

Step 1’s recap:
Introducing anal play should be done alone in your own time as a typical penis/dildo will be too large to take without pain for a first time

Go to the bathroom first, then flush 1 to 2 times out with warm water using a enema bulb or 1/5th of a plastic water bottle. Don’t use too much water!

Having solid shits is the quickest way to an easily clean out before anal

Your Body Sets the Pace

Setting the environment:
Like vaginal play, anal needs foreplay. You need to create an environment where you won’t be interrupted by others. In a comfortable position. Have all the toys, lubes, towels, and distractions/entertainment within arms reach.

My favorite way to start an anal session is by taking a bath and letting my muscles relax. Find your way of relaxing your body. Whether that's a hot shower, yoga/meditation, or in your bed with lots of fluffy blankets.

Once you’ve relaxed, pick your spot to have your anal session. Personally I like to put a towel/blanket against the bathtub wall and lay against the tub with knees bent. I recommend a carpeted floor with a towel laid down(to catch any excess lube) where you lean against a wall with a blanket on your back. I find anal play on myself in bed to be difficult since my ass sinks into the bed and it is hard to get the right angle. No matter what you’ll need your ass to be supported to some extent.

Nearby you’ll need lube, I recommend silicone based lubes for anal. I find water based lube to dry out way too quickly and have too much glide. I love using my x-lube for anal because I can make my lube as thick as I want it. If you don't have lube, grab olive oil or coconut oil. I used olive oil for nearly a decade and had no problems.

Next you’ll need a towel, small anal toys(not much bigger than your thumb) or smooth household objects you want to try out, your phone or tv, and a cup. The cup is just in case you need to suddenly pee from the pressure of anal, often applies if you're a guy stimulating the prostate since the bladder is close by.

Time to get touchy:

Once relaxed and have everything you need to go nearby, I highly recommend distracting yourself while you introduce yourself to anal play!!! Many beginners have this mindset that they need to get this anal thing done and get impatient with what their body isn’t accepting. To solve this I recommend you watch your favorite movie/show during your anal sessions. This will take your mind off of anal play having a timed agenda, the agenda is whatever your body is ready for. If you have any pain, never push through it. Stop where you are at and go to a smaller size, add more lube, or end the session if you made a tear in your anus. Discomfort is ok in moderation, that's how you initially push yourself to take bigger sizes.

Start by lightly touching the outside of your anus with the pad of your finger circling it, going up and down and whatever motion you feel like. Next apply lube on your finger, warm up your lube with warm water if it's cold. Anything cold will tense up your rectum. While distracted by your phone/show/movie slowly go partially in with your lubed up finger. Work your way up until you can fully press your finger in. Don’t worry about it not feeling amazing as the pleasure of anal comes from heat, vibration, being filled, and hitting the right angles(all of these we will get to soon).

Once you can handle a single finger, try two fingers or use your small anal toy. Experiment with rhythms and angles. The more you play the more you’ll figure out what tempos are pleasurable.

Now We Turn Up the Experience:
So now you are able to put a finger or small anal toy in your ass without discomfort. It's time to give yourself options by getting to the size of an actual dick/full sized dildo/larger prostate toy. Buying an anal kit is very cheap, they provide you with a gradual way to stretch out your anus. Anal plugs are good for getting your ass used to having something in them but keeping them in your ass without movement will not stretch and train your ass to take bigger toys. Stretching your ass to take larger toys requires movement, always go slowly in and out to stretch. If something is too large for you initially, then pause where you are at until you can add the required movement. Always apply tons of lube for anal, it's far more difficult to run into the problem of too much lube than too little.

Tip before your first anal sex session: Make sure you build up to the size of your partner. Find a dildo similar in size and work your way to the point you can go in and out at a good pace. An hour before your anal sex meet up, clean out and stretch so you can get to the action faster.

Where the pleasures at:

There are countless anal toys and gadgets for anal pleasure. Vibration and heat are my favorite features in an anal toy. Some like crazy shapes, some like fast thrusting, some like unique textures. It's up to you to find what gives you that anal thrill.

For women: anal can be pleasurable because the pudendal nerve runs through the pelvic region, supplying sensation to the anus, vagina, clitoris, and perineum.
Stimulating the anal area can send arousal signals along these shared neural pathways, heightening overall sensation
For men: Prostate Stimulation: The prostate gland is often called the male G-spot. It is very sensitive and can trigger intense orgasms when stimulated.
Dense Nerve Endings: The skin and tissues around and inside the anus contain many nerve endings (such as branches of the pudendal nerve) that react strongly to touch, pressure, and fullness

For guys you can find the prostate by pushing your finger/sex toy in about 3-4 inches in to find a walnut sized gland when you go in the direction of your belly button. Lightly do a come hither motion in the rivet of the gland, often light to medium pleasure is best. I've personally found I get the best prostate orgasms by lightly playing with the prostate for 30-45 minutes then going really aggressive with a come hither motion on my prostate, making me shoot prostatic fluid.
Clean up
With the amount of lube required for anal hopefully you had a towel nearby/down to easily wrap up. For cleaning toys: run hot not cold water for silicone/oil based lube because heat lowers oil viscosity and helps break down grease. Companies do sell specific anal cleaning foam for anal toys, but hand soap will do the job just fine.

Quick summary:
Your first anal session should be alone so you can introduce yourself to anal properly

Get familiar with the great potential anal sex/play can give, well beyond traditional vaginal/penis stimulation

Clean out using an enema bulb, avoid using too much water. Having a good diet where your shits are solid will speed up this process immensely

Set up a comfy environment where there will be no distractions and you have everything you need in arms reach

Start slow with your hands while distracting yourself with your favorite show/movie to avoid rushing the process

Buy an anal kit to build size tolerance and learn the proper techniques

Explore the amazing pleasures of vibration, heat, thrusting, texture and much more

Anal is something should never be painful and should be given another chance if your first attempts did not involve the proper preparation and gradual progression anal requires

Check out my favorite anal and prostate toys here!
B-Vibe 360 prostate massager
B-Vibe remote control rimming p-spot plug