Try to remember the last time you were doing something completely new.

Maybe it was a guitar lesson or your first snowboard experience — it can even be something as simple as trying out a new makeup.

I’m pretty sure you screwed it up.

Your guitar gig probably had nothing to do with music, the snowboard most likely developed free will at the expense of your bruised behind, and your makeup looked inspired from a bar fight.

We’ve all been there. It is more likely to mess up than succeed. Anal sex is no different.

A bad anal sex experience is the equivalent of breaking your leg during your first snowboard lesson. In a nutshell, it hurts like hell, and you will not want to repeat it.

This post covers some of the reasons why you, just like most couples, fail at having anal sex. If you want a more in-depth view on the subject read the issue of my magazine dedicated to the Good, Bad, and Ugly of Anal Sex.

Lucy's Anal Sex Guide


Take it with humor if you want to succeed at anal sex. What I have learned from the couples I talked to during my amateur marriage counseling is that a long relationship is not necessarily a mature one.

Mutual respect, openness, trust, and your ability to be yourself and make fun of your flaws are more important than the years you are together.

In more practical terms, if you are comfortable enough to tell your partner the joke “How to Wipe Your Butt with One Sheet of Toilet Paper” (google it!) you are ready to engage in some high-quality anal sex ecstasy.

Let’s be blunt about it, you don’t have roses up your arse, and you need to be big enough to deal with the consequences.

Look on the bright side, if you fail, at least you too will have a new joke to tell.



Frankly, I believe that anal and oral sex are something to be done only with some designated few. It is my personal belief that these two activities are more pleasurable in a trustful relationship rather than on a street-corner.

Fucking around isn’t female emancipation.

Too many young girls use anal sex to be more appealing to men. They falsely assume that sexual promiscuity is what keeps a lover happy and loyal. This makes a bad sexual experience.

Ladies, you only have three holes. If you rely on them to keep yourself interesting, I’m afraid you will fail badly. No amount of anal sex, deep throating, or God knows what else you are willing to try out, will make you more desirable.

On the contrary, a decent man will feel repelled by the carelessness with which you offer your body to people who didn’t qualify to worship it.


On October 29, 1941, United Kingdom Prime Minister Winston Churchill visited Harrow School to hear the traditional songs he had sung there as a youth, as well as to speak to the students. This became one of his most quoted speeches, but I bet no one used it in an anal sex article before.

Never give in – never, never, never, never, in nothing great or small, large or petty, never give in except to convictions of honor and good sense.

Never yield to force; never yield to the apparently overwhelming might of the enemy.

Winston Churchill

Winston is a great guy and all, but he obviously has no clue about anal sex. He might have inspired Vince Lombardi, an American football player, coach, and executive to say “Winners never quit and quitters never win.”, but he shouldn’t inspire any woman trying to have anal sex.

If Winston Churchill had given a speech about anal sex, he would have said something differently. I imagine this.

Never push it too hard – never, never, never, never, in no butt, great or small, large or petty, never push too hard, not even if honor or good sense pushes you.

Never yield to force; never yield to the apparently overwhelming might of your desire to deliver anal sex because you promised you will.

In other words, if your body tells you to quit, QUIT! This is not Crossfit. Don’t force yourself just because you committed to it. This usually is a recipe for disaster.

The reason is simple: it is easy to underestimate the sensitivity of your anus and hard to understand just how painful it might get when you do.

Be prepared to quit if you must. Prepare your partner for it as well. Quitting is not for losers, it is for women who want to keep their asses intact, and leave a door open for trying it another time.

Even experienced gals don’t know for sure if they will enjoy every particular anal sex experience. A lot of things are at play – their mood, their partner, or something just as trivial as their diet. If they don’t feel comfortable they quit, hit the shower and try something less demanding – a hand job maybe…


Your ass knows some basic things about how the world works. One of it is the direction in which things move. It is usually from the inside to the outside. This been said, please forgive your ass for being a bit confused because – for a change – something is getting in, and not coming out.

You might be extremely hot and willing, however, your ass isn’t. Putting a cock inside is something that requires sneakiness.

There is a way to persuade your ass to open up. Distract your brain with a clitoral orgasm. Take out your vibrator, position it on your pink pearl, and start polishing it. This usually helps you relax and makes you more willing to welcome your partner through the back door.


If you look at anal sex as something you will try out once to see if you like it, you already failed. Chances are, the first time you decide doing it, you will not have anal sex in the first place.

You already saw how many things can go wrong. Be advised: this is a very short list. Anal pleasure needs a lot of consideration.


In anal sex, even the mere intention counts. Your partner will gladly wait for you to be ready, especially if he understands that when you will succeed, you will enjoy it as much as he does — or even more, if done correctly and with consideration.

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