Vice Guide to Anal Sex

Back in University, while having sex with my 32 year-old militant feminist girlfriend, a phrase slipped out of my mouth. We were in that primal mode-in auto-pilot when weird sounds come out like “goood” and “do it -fucker.” This time however, out of nowhere I go, “I love hurting you.”

Instead of getting angry or disturbed, her eyes lit up and she said “I love it when you hurt me.”

That was the first time I totally understood what it’s all about. Love hurts and sex is hostile. As Robert J. Stoller writes in Sexual Excitement: “the absence of hostility leads to sexual indifference and boredom. Humans are not a very loving species especially when they make love.” In a time when everything is about egalitarianism and feeling good we are forgetting the merits of pain. What about the joy of dirty smells and helplessness? The joy of taking over someone’s body like snake with a frog in its mouth. I love that shit.

So without further ado, here is the VICE guide to the cruelest of lovemaking. The only sexual taboo left: getting reamed up the cake.

FAGS GO HOME

Before we get started. We have to zero in on who we are talking about. This article is not for fags. Telling fags how to have anal sex is like telling Puerto Ricans how to have babies. Fags are so over it they could wake up in a sea of blood and poo, with a hangover and say, “that didn’t work out so well. Let’s go get some Amyl Nitrate and try it again.” They are the masters of the sport and have all kinds of great tips on how to use crack and other drugs but, I don’t know, that’s just not the hetero way.

This instructional guide is for heterosexual couples who want to put the boy’s dink in the girl’s bum. There is a side bar on how to nail hetero guys but it’s so easy it only deserves a few words.

The “no way in hell” girls have two distinct characteristics. One, they hate bands with female singers and two, they shake their heads when you ask them if they liked the first try and then go “it felt like I had to go poo.” If you’re girl is like this stop reading now and try to get over it.

GIRLS DOWN WITH THE BROWN

There are several types of ladies that are perfect for sodomy. First generation immigrants are great because, after being bombarded with all kinds of new experiences (baseball, MTV, spaceship cars) she is ready to try anything. Virgins are good too. They just figured out how to work their vagina so adding another one next to it isn’t so absurd. It’s like someone coming over with an extra cup when you’re doing the dishes. You’re just like, “oh that too? Oh OK let’s get it soaped up.” The ultimate catch as far as willingness goes would have to be Catholic schoolgirls. Thanks to oppressive fathers insisting their hymen stays intact, every other orifice gets a rigorous workout before graduation. In fact, nine times out of ten it’s the Catholic schoolgirl that introduces it to the boy. “You don’t need a condom,” she’ll say,”we can bungi” (that’s their special word for it) and then that spoiled little boy is ruined forever.

Odds are, you’re in a relationship with someone in between. She’s not totally against or totally into it. If so, you should be reading this, which you are, so, good.

Oh wait there’s more shit we have to clear up. Before you start hurting someone, let’s make it clear what kind of pain we are talking about. There is good pain and bad pain. Good pain is dull and all-consuming and bad pain is sharp and very localized. If you’ve ever put a girl’s legs behind her head and had your boner ram her cervix during sex that’s what bad pain is like. You can tell because she gets up fast like your dink’s an electric eel and it makes her so mad the lay is usually over. A well-lubed, slow and careful intrusion is a good pain like being sat on by a fat person you love. The bad pain of an unlubed and rushed anal intrusion cuts her ass, pisses her off and kills the whole thing forever.

GETTING IN THE DOOR

She won’t like anal sex until her 17th time. It’s an acquired taste. But you have to get her to want to go through that good pain, 17 times. To get that response, you must employ the “Pavlov’s Dog” technique. When you’re eating her out, occasionally touch around the asshole. Give it small and swirling “hellos” like if you were trying to pet a newborn squirrel without scaring it too much. It’s best to try this when she’s totally horned up out of her mind and plastered. If you take it slow and easy and smart you’re looking at a total time of five months. Don’t be afraid to lick it sometimes. Salad tossing is not gross with women because they shit roses. Put your finger in there and smell you finger. See? Roses.

After you’ve got through the taboo front gate you can start being more and more friendly with the baby squirrel.

If things are going too slow you should skip to the “Turning Him Over” sidebar and have her try it on you. Once you’ve gone through it her curiosity is awoken. She’ll be like “didn’t it feel like you had to go poo?” And you can be like “no, I loved it.” Then she’ll be like “really?”
Nice save.

THE BROWN CAVE

After massaging becomes totally commonplace you can occasionally inject a well-lubed pinkie in there when she’s cumming. This is called the Trojan Pinkie Pavlov Horse or “TPPH” for short (pronounced by making a fart sound with your mouth).

You are going to notice some weird things in there. First of all there’s a lot more room, than you expected. Once you get past the bouncers, it’s a roomy club. That’s why butt plugs are cinched where the anus goes but are all big where the rectum is. You may also notice a very prominent pulsating vein. I have no idea what the fuck that is. It’s a vein. Probably a good way to check someone’s pulse if they have fat wrists because the thing is like “bong, bong, bong, bong.” Don’t worry about the vein.

The third thing you may or may not notice is a little soft finger poking back at you. Like a squishy little Turkish ET. That is a piece of poo. Don’t tell her you felt that or she’ll be all grossed out. Just treat it like a pussy fart and pretend it never happened. Incidentally, the poo finger means you are going to get some shit on your cock. You’re probably wearing a condom anyway but if you aren’t, get to the bathroom the second you are done. DO NOT PASS OUT! Waking up hungover with a shit encrusted foreskin is a dangerous way to hit the showers. The hot water reactivates the stench and your already delicate stomach will kick food out of your body like a shovel throwing dirt.

THE SECOND DINK

Once she’s kind of into finger cameos, start incorporating the lubed finger during fucking. Now you can start going from pinkies to index to a thumb. Then maybe even two fingers. You are at the point now where the anus has become a baby vagina.

Now she actually looks forward to her daily anal penetration. Don’t underestimate how far you’ve come. This is as exciting as the first time you got a girls pants off and was able to finger her properly. If things keep going this well she may eventually learn to cum from it.

Just kidding only God gets that.

Before moving on to dink town you can pull butt plugs into the equation and other fun toys. Your basic dildo is a good way to stretch out a rookie ring piece because it has no ridges or things to trigger a cut.

PROM NIGHT

Don’t get too excited you fuckers. You’re not there yet. Lube the shit out of her ass and your dink and place your dink’s face right at the anus. Then go “It’s going to go in your ass.” Make doubly sure it’s lined up and say “push back.” Unless you’re a 14 year-old on Viagra, things may get a bit bendy here. Hold your dick solid by grabbing it just behind the head the way you would a deadly snake.

It’s important that she relaxes and doesn’t freak out or it’s going to hurt and then you’re back to step one again. One good way to keep it sexual and relaxed is to be rubbing her pussy as she pushes back on it and even throw in some gentle verbal coaxing.

If she’s not into it or it hurts too much give up and try again in three days. Don’t worry it’s not over. If you’re really eager to try again you can put it back there just as you cum (assuming you take the condom off like I know you would you dirty bastard) and all the lube of blowing your load will sloop it in. Not exactly a reaming but it’s a good first try.

Once you get it all the way in and there’s no cuts or damage, start going at it at a reasonable pace right away. If you’re too slow it’s going to hurt her more so get that bad part out of the way ASAP.

The word is a magical four-letter word that sounds like “ungh” but is not to be confused with “uh” or “unh.” “Ungh” is a deep-throated “uuunnngh” that sounds like the person saying it is not the person saying it. Like a demonic possession made her roll her eyes back into her head and replaced her voice with Barry White getting kicked in the stomach. Seriously, it’s almost scary. It’s so Exorcist guttural you expect her head to rotate 360º and projectile vomit to blast into your face followed by the words “mea culpa lorem ipsum nosferatu.”

Don’t get too proud of yourself partner. You may have made it but now it’s time to run with the ball like Satan would want you to. Keep rubbing that pussy and up the anti with a bit of dirty talk. Getting her to say “you are fucking me in my ass” is really good for some reason and of course “I love your cock in my ass” is great too.

After you cum take the condom off and throw it far away in case there’s poo on it. If you weren’t wearing a condom then go “pee” and, when you’re in the bathroom, wash it off.

Now that it’s over let’s have a bit of affection. While your red knob throbs down to its original size and jiz seeps out of her ass show her that Dr. Jekyll is back and he still has a huge crunch on her. Try spooning her and singing the following:

“Snuggle frog, snuggle frog, I love you. I got a snuggle frog how about you?”

Now sleep.

Guess who’s a dirty little bitch. Guess who’s going to get it like a dirty little whore. He is. That’s who. He’s going to get it for a change. Here’s what you do girls.

I know this is starting to sound repetitive but the “no nicking” thing applies to women, especially. If you have any kind of fingernails put a condom over your poo finger. I mean it.

Guys who wear overalls, like R&B, and plea feminist causes at the MTV Music Awards just because their girlfriend was in a bad mood, are pretty simple to lay in the ass. Just reread the main article and change every “she” to a “he.” Replace the “rubbing the clit” part with a reach-around while you’re at it.

If you’ve got Wet Wipes around you could even do a little salad tossing but if you’re down with that you probably don’t need to be reading this. After a while you can get it to the point where a finger in his rear during a blowjob is “de rigeur.” Men’s asses are nine times more disgusting than women’s, though, so take Margaret Cho’s advice and don’t let that finger touch your steering wheel on the drive home. Keep it up like you’re saying “hey” to a fellow driver.

BUT WAIT THERE’S MORE

Once you’ve gotten even a finger in there, the sky’s the limit. Now you can move up to butt plugs, strap-on butt plugs and even strap-on real dongs (good luck). We highly recommend you start with the jelly butt plugs because they have a little more play and will hurt less. It’s funnest to sodomize girls while they’re on all fours. If you’re reaming a man with a strap-on, butt plug however it’s actually better to have him on his back with his legs up. Now he can wank while you do your thing and it’s more freaky.

Oh yeah, don’t let him look at you with a strap-on. That is going to freak the shit out of him and it may blow everything. Lights out and heads averted above the waist is best.

There is a weird thing that happens to men after the strap-on thing. They behave differently the next day. They seem to come to a kind of realization that being a bottom isn’t as subservient as it sounds. They finally understand that you have to be kind of brave to let someone put a bit of their body inside yours. The next day you’re going to hear him say things like, “yeah, that’s a good idea. I should put that picture there.” That’s because, instead of hearing “meow meow meow, blah, blah blah meow” everytime you talk he’s hearing “hey that’s the guy that served as Scientific Director of the DOD Navigation Satellite Program Executive Director of the Four Service Group which initiated the Navstar GPS program in the early 70s.”

THE BIG GUNS

Unlike fucking women’s bums, where you have to keep going until you get to the “ungh” stage, sodomizing heterosexual men is far less ambitious. You can stop at each level, indefinitely, and not go any further. Many women are satisfied simply putting a finger in his bum during blowjobs. Some stop at the odd butt plug in there. Don’t feel bad if you stop at an early stage.

You’re not going to get an “ungh” out of him from the butt plug (even though, for a guy it feels like you just put an Encyclopedia in there). The only way you are going to get the “ungh” out of a him is to get something penis sized in there.

For information on that you are going to have to consult the gays because you have now gone into some Jedi knight shit that is way over our heads.