Here’s Every Gory Detail You’ve Ever Wanted To Know About Anal Sex

I feel like a title should clue you in to the contents of the article, but I’m going to be as clear and literal as my words allow:

This is an article describing in extremely explicit terms aspects and frustrations of anal sex, including those that involve feces. Specifically, those elements of anal sex that I have rarely to never heard anyone talk about outside of the confines of extreme privacy, due to their uncomfortable nature.

I won’t be euphemistic.

This is your last warning.

Women often don’t like anal sex because they’re not prepared for it.

I have noticed in male-female relationships that there are two things Boyfriend Zero has fucked up for everyone: oral sex and anal sex. Oral sex is really easy to fix; anal sex isn’t. Convincing a woman to have anal sex is hard to begin with, and after endless goading they finally try it and it’s horrible because some idiot doesn’t know what he’s doing. No one will touch her asshole again for years.

Are you understanding the gravity of what I’m saying? Sophocles could have written this shit.

At some point there should be an ass-tribunal for these men and their crimes against sodomy. So here is a code: if you can’t take your own dick up your ass, you have no business putting it in anyone else’s. This applies even if you’re “straight.” Oh, you haven’t shoved anything up your butt yet? Then don’t shove something up a girl’s butt. Take it up the ass first to see how it feels, you fucking pussy. Once you’re confident that you could take your own dick, then you’re ready to convince a girl to do it. Until then, shut the fuck up.

Here are some more questions to ask yourself: can you stick a 6” dildo (or dick, but dildos are de facto dicks) up your ass period? For how many pumps before it’s unbearable? Can you insert and re-insert without pain, like you’d need to be able to do if you were being fucked?

Some women think that if they can simply get their boyfriend’s dick in then that’s sufficient. It’s not even close. Try this: 80% or less of the largest thing you can insert is what you can enjoyably have anal sex with. If you’re taking your boyfriend’s dick in your ass and your boyfriend’s dick is simultaneously the largest thing you’ve had inserted into your rectum, it’s probably going to feel like shit. If he’s 5”, you should be able to take 7” for a few pumps without dying. (I’m assuming length correlates with girth to simplify things.)

This is, how I imagine, most conversations about anal sex go:


guy: hey let’s try anal sex
girl: no

~ice age of convincing~

girl: okay fine once
guy: awesome

(Let’s assume this woman isn’t like the woman in Tucker Max’s anal sex story who doesn’t empty her ass and shits all over him.)

guy: *gets astroglide*
guy: *inserts a couple of fingers*
guy: okay I’m ready *inserts dick*
girl: holy fucking shit ow I don’t like anal
guy: :(

And anal is ruined forever.

Her asshole is unavailable to every subsequent boyfriend. Fuck that guy.

Here is how a realistic conversation about anal sex should go:


girl: I want to do anal (immediately it’s established that this is a fictional example)
guy: Harry-Potter-finding-Ollivanders-wand light shining down on existence
girl: *buys a small dildo*
girl: *buys a medium dildo*
girl: *buys a larger dildo*

(one month goes by of using these on the daily, working upward in size)

girl: okay I can use the large one now

And they had anal sex, and it felt really good, and everyone was happy and no one wrote in the comment section about how much they hate it.

It’s very difficult to convince someone that their previous attempt at anal sex was wrong. I mean, it probably was, but look: I can take a 9-inch dildo up my butt, because I’m an adult and I solve my own problems. But I didn’t start out that way. My index finger felt enormous at first. Virtually everyone I know who does this has used a hairbrush handle as a transition between their fingers and a cock. And eventually, you can start using a cock. Just not right away. It’ll take about a month of regular sticking-shit-up-your-ass. And once you get to the point where a regular-sized penis doesn’t feel big, it will feel really good. You have to believe.

But the moral of this story is that I believed in myself. If you believe in yourself, you can take a huge dick up your butt too.

If you’re going to take a dick in your ass, you have to take an enormous shit before you do it and finger out every remaining bit of feces after that.

I’m not exaggerating. You need to shit out every bit of feces from your rectum. Your ass needs to be completely empty. This seems like it would be intuitive, but a surprisingly large number of people do not do this. If I’m about to fuck someone in the ass and I feel a hard, dry, unreleased log of feces against the tip of my dick (this is an unmistakable feeling) I will simply stop there. We can have vaginal sex, or, if you’re a guy, I can get on top of you, because at least I am a responsible person who empties their rectum at the possibility of sodomy. But I’m not going to get that shit against my dick.

You probably read the second part correctly, by the way: you should get in a shower, grab some kind of petroleum jelly or lubricant or whatever, and finger out every remaining bit of feces from your rectum. Use a hook motion with your finger if you have to. But simply taking a huge shit will not expunge tiny fecal remnants. You need to get everything.

If you’ve never had anal sex before, you can probably deduce that spontaneous anal sex almost doesn’t exist. It can, but a lot of lucky things have to happen. Namely, you (or your partner) would have to be the kind of person who gives themselves an enema on a daily basis on the off-chance you meet someone you want to exchange asshole bacteria with. Then, you’d need to carry lubricant around with you, and be stretched-out enough that you could lubricate in a hurry without pain to your rectum. I have never met anyone dedicated enough to assfucking who actually does this.

There’s more to painlessness than “use lots of lube.”

Every anal guide ever says “use lots of lube.” No shit. Assholes don’t naturally lubricate themselves like vaginas do. But what I think most people take from this is that you should put a shit-ton of Astroglide on your dick and you’re solid.

That’s not how assholes work, asshole. The rectum is lubricated progressively. So for each insertion, more lubricant will spread throughout the rectal walls, but it’s not something you can do in one pump. If you’re sticking something in your ass or someone else’s ass, you will need to lubricate that thing, stick it in once, pull it out, obnoxiously re-lubricate it, stick it in again, obnoxiously re-lubricate it, stick it in again, obnoxiously re-lubricate it, and by the 4th or 5th time whoever’s ass this is should be sufficiently lubricated internally.

Any person who lubricates their dick once and sticks it inside of you without re-lubricating is a fucking idiot and an idiot at fucking. Don’t sleep with them.

Men are really horny after they take a huge shit.

You’ve probably heard that the “prostate is the male g-spot” and this is essentially true. The most intense orgasms I’ve had have been this way. However, what you might not know about men (unless you are one) is that enormous bowel movements press against the prostate and by the end of it, you’ve had enough prostate stimulation to make you want to fuck and badly.

This is my personal experience with this, but I’ve always found that there are three ‘waves’ to prostate stimulation: there is the first initial stimulation of purging all the feces from your ass. There is the second stimulation of actually inserting something in your ass. Then, if you wait for about fifteen or twenty minutes and do it again, the prostate is especially sensitive and the third wave is euphoria. It’s resulted in some of the most intense orgasms I’ve ever experienced. Full-body spasms, which seem like the kind of experience reserved for women when they talk about their most intense g-spot orgasms.

Think about the implications of what this means when bisexual or homosexual men go around looking to have casual sex with other men, and specifically at gay clubs known for this. A solid fraction of these men have not only made sure that their bowels are empty prior to going, but because of that they’re considerably more horny than they would be had they just been looking for pussy in a straight club.

There’s a good chance that this thought has never entered your brain, but that’s why I’m here. Also, if you’re a straight or bisexual woman, a great time to hound a man for sex is about 30 to 60 minutes after he’s taken a huge shit.

If you’re fucking a woman in her vagina, you can massage your dick through her asshole.

To this day, I have not heard anyone talk about this, nor have I seen it happen in porn. But maybe it’s time we broached the subject: if you’re a guy and her asshole is stretched out enough to take your penis, you can definitely insert a couple of fingers into her ass while you’re fucking her vagina. At the very least, you can insert two thumbs. And when you do this, you can actually push your fingers against her rectal wall and massage your dick as you’re thrusting into her vagina.

I don’t normally consider myself a genius, but when I first discovered this I felt like Leibniz developing Calculus.

To their credit, women already do the reverse of this: if they’re taking a shit and it’s too big, they can use their fingers to push the shit out through their vagina. Admittedly this is really cool, but I’ve been without this advantage for so long that if I suddenly woke up and had it I’d feel like my defecatory accomplishments were flushed down the toilet.

CLEAN YOUR ASSHOLE.

Sure, I have read guides that say that washing your asshole with soap and water dries it out. And in my defense, I’m not saying you need to straight up grab a bar of soap and rub it on your anus. But it is fucking disgusting to think about eating someone’s asshole who has not soaped it. If you know someone is going to be coming in contact with your ass, soap up your hand and wash your anus with it beforehand. (Besides, if you’re about to have anal sex with lube, it would logically follow that your anus is not going to be dry for long.)

Not surprisingly, the women I have slept with who had the most disgusting anuses were consistently women who (A) were scared of anal sex and (B) did not clean their assholes because they were repulsed by them. Yeah, I’d think anal sex was disgusting too if all assholes looked like yours. Am I entitled if I don’t want to see dried chunks of feces hanging off of a woman’s anus when I’m 69ing her? I really don’t think this is an excessive request.

Also, if you’re a guy and aren’t meticulous about this already, there’s a strong chance you have hair around your asshole. Hair holds bacteria and feces and you probably have more of it on your ass than women do, so if you’re going to be doing anything with your ass, then clean extra-carefully. Arguably you should shave the hair around your asshole entirely, but this is considerably more time-consuming than merely shaving your dick and balls, so I understand if it’s not your preferred course of action.

Stop freaking out; your ass isn’t going to die.

I showed a draft of this article to a friend and she protested that she didn’t want to stretch her asshole out, that she has a great asshole as it is. To her credit, she does. But look: you naturally take the equivalent of a dick out of your ass when you take a shit. So after that, you’re already stretched out. I’m doubting that you’re walking around freaking out after you take a huge shit because your asshole is permanently fucked up. You understand on some level that it doesn’t work that way. And, yeah, you’re much more loose when you’ve just expunged feces from your ass and your rectum is lubricated with Astroglide, but then that’s why you’re not walking around like that all the time. The rectum’s default state is dry and very tight. You will not alter this state much.

Really, the only thing that changes when you can take a very large dildo up your ass is that maybe you might not feel like you’re going to die when you take a monster shit. Otherwise, your rectum is going to be pretty much the same. According to a scientific penis percentile chart, the top 1% of girth begins at 6 inches in circumference and the top 0.01 % at 6.75. Considering that 6.5” to 7” is on the upper end of doable for me and I’ve never had problems with my butt, I doubt you’d notice any rectal problems until you got to something bigger than 8” in circumference, which is like one-in-a-million level of girth. The only people I know for a fact who have experienced issues due to stretching are people who make enormous insertion videos where they stick things like footballs and liters of coke in their ass, and those things surpass 9” or even 10” in circumference.

Ask yourself: are you sticking a liter of coke in your ass? If not, then chill out.

Stop freaking out in general.

This isn’t really a key instruction so much as a request, but I wrote this article with frank language because many people I know are uncomfortable talking about anal sex, and it doesn’t have to be that way.

The level of frankness I’ve used here is the level of frankness with which you should be able to discuss anal sex, yet I’ve hardly known anyone who speaks openly about it. In general, it’s an uncomfortable subject. An asshole is “down there”, a dump is “number two”, the rectum is “the wrong hole”, and so on. No one should have to tiptoe around a statement like “I want to fuck you in the ass.” If you have to walk on eggshells when discussing anal sex, you can’t fully appreciate it with the person you’re shielding.

As far as I’m concerned, trying anal sex is like trying sushi. Lots of people have; it’s not a big deal in the 21st-century. We shouldn’t act like it is, because if everyone is still scared of it, there is substantially less chance that many people will do it right. Truly, the quirks of assfucking should be something you’re able to talk about, openly, with the same freedom that you’d use to talk about shaving your pubes. That’s a pretty touchy subject on its own, but no one gets their balls in a knot like they do when talking about anal.

And anyway, let’s be real: you just clicked on a 2500-word article about anal, where you were warned from the title onward what you’d be getting into. If you’ve read down to this point you’re beyond claiming some imaginary high ground, so don’t get butthurt about assfucking.

But really, clean your asshole. TC mark

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