Hiya Alex,

Just a quick question but how do you make a girl feel confident enough to let you perform anal sex with her? And is there any particular way to do it, and can you do it wrong? This is something I have never tried so you could say that I’m as nervous as she is. I haven’t been with that many girls, and even though 1 or 2 of them may have been gagging for me to slip it up trap 2, I just didn’t have the confidence to ask them. For all I know it may have given them the wrong impression of me, or something worse I dunno. Any information you can give me on this rather delicate subject will be greatly appreciated.



I’ve got some great information to share that relates directly to your question– but before I get into it, I want to make two very important comments…

Personally I have played the field A LOT between relationships, and I’ve probably been with far too many women for my own emotional well being. In any case, I’ve been with enough women to know this: Relationships are better.

Right now I am in a relationship with a woman who is everything that I could ever dream of, and I very sincerely intend to do everything I can to make it last forever.

Intimacy beats novelty any day of the week, my friend. I’m not saying novelty isn’t fun…

I’m not saying there is anything wrong with being single or playing the field… it’s an important step in your development. But I like to hope that every guy gets past that, matures emotionally, and, if he’s lucky, meets the kind of woman that makes it worth investing the effort to stay monogamous.

When I give out my advice in these Newsletters for FREE…somewhere in the back of my head I’m always hoping that the guys who are really “getting” what I’m talking about and actually USING the information are in serious relationships and using my advice to increase the love and passion with their one special girl.

That’s what “good karma” would be for me.

So now let’s roll up our sleeves and see if I can answer your question.

I’ve actually gotten this question before, but I decided to answer YOUR email in particular because I really liked the way you said:

“How do you make a girl feel confident enough to let you perform anal sex with her?”

The way you phrased the question shows that you really have been paying attention to my Newsletters and that you really UNDERSTAND female sexuality in a deep way. Your girlfriend is very lucky… and I’ll BET that she KNOWS it, and brags about you to her friends.

Because MOST guys wouldn’t get that it is not an issue of how to “talk her into it”… and it’s not an issue of “making her want it”… and it’s not an issue of “getting her permission”…

It IS an issue of making her comfortable and CONFIDENT enough about herself, and about the TRUST she has in you and your sexual comfort with each other that is really the key here.

Let me start with a few very important basics:

1. BE CAREFUL The walls of the anus are much more delicate than the vagina. That means they can rip (gasp!) if you are too forceful, or if you don’t use enough lube. Start gently, and be aware of her comfort level before you start going faster or harder. If she says it hurts– stop, slow down, use more lube, don’t go as deep until she is ready.

2. USE A CONDOM I know that a lot of guys have seen all kinds of things in pornography… PLEASE remember that porn is not a good example of what YOU should do or what is right. There are legions of potentially harmful bacteria up there. There is a reason that the body is getting rid of that crap! And you can get all kinds of disgusting, potentially dangerous…even potentially deadly diseases from anal sex. Often there is some bleeding, and that opens the door to a bunch of other potential diseases.

Use a condom. And use a water-soluble lube (the kind that says it’s okay for use with condoms right on the package, like Astroglide or K-Y) to help ensure that the condom doesn’t break.

3. DON’T PUT YOUR COCK ANYWHERE ELSE AFTERWARDS Again, forget what you might have seen in some super exploitive porn flick on the Internet…this is a real girl that we’re talking about, and her safety is YOUR responsibility. Do not take your cock out of her ass and put it into her vagina or mouth or anywhere else.



Remove the condom and wash the area first. Then do whatever else you like.

4. RESPECT HER WISHES In this Newsletter I’m going to tell you exactly how to talk about anal sex and exactly how to get MOST women to agree to trying it out. The fact is, there are plenty of women who LOVE anal sex and just can’t get enough of it. But there are also some women who are just never going to agree to it. Usually this means that they have some issue that has nothing to do with you, and often nothing to do with sex at all that prevents them from going there.

If that’s the case with the girl you’re with, then don’t continue to push her for it all the time or eventually you will damage the relationship.

Most of the time, a woman will come around when she feels comfortable enough. Most women are very eager to please their man, and many are curious themselves about the experience. So most of the time, if you follow the guidelines below you’ll have no problems.

Okay, that’s the basics. Now let’s talk about how you actually get her to go for it.

Just as you said in your email: the key is getting HER confident enough to do it. So first let’s ask ourselves, ‘why would SHE need confidence to let me have anal sex with her?’

For starters, she may be afraid that it’s going to hurt.

And she may be afraid that you will go too hard (she’s probably afraid you will be just as aggressive as you are when you are really pounding her vaginally). And she may be afraid that once you start, if you are really excited, it may be difficult to get you to stop if she doesn’t like it.

There’s a lot of content in the above paragraph, and you just might want to read it again.

Here’s a VERY IMPORTANT thing to remember about all sex you will ever have with a woman:

It is very different for her than it is for you… Because while you are naturally sexually attracted to soft, delicate, feminine women…SHE is naturally sexually attracted to someone who is MUCH stronger, and almost certainly bigger and more aggressive than she is.

Sex really IS dangerous for women. And men, at any time, might use their superior strength to make her do things she doesn’t want to do.

And that, my friend, can be very scary for her. Of course, you are in a relationship, and she trusts you… but still, once you are really “into it” is she positive that she can get you to stop? Well, she might be, if, based on your sexual history with each other you’ve demonstrated time and again that you can be sexually TRUSTED.

This may sound crazy, but if she’s “not in the mood” some night and you are kind of pushy, and then sort of angry with her afterwards if you don’t get your way… guess what?

You have one strike against you in the game of getting into her ass.

Not a big deal… but things like that add up in the game of sexual trust.

So one thing you might want to do if you are talking to your woman about anal sex for the first time:

Reassure her BEFORE SHE BRINGS IT UP, that you will be very gentle, and that you will stop instantly if she asks you to.

By saying it BEFORE she brings it up you will get huge bonus points for understanding her feelings…

But also, she will not feel like “oh, he only said that because he’d say ANYTHING to get me to do it.”

Reassure her that she, as a person, is much more important to you than anal sex.

Most of this reassurance will probably have to happen in your daily interactions with her, but it can’t hurt to mention it when actually discussing anal sex.

Now obviously none of this is going to be a huge issue if she’s done it before and enjoyed it.

But what else might she need “confidence” for when it comes to anal sex?

If you said, “embarrassment” or “the smell” you win the prize for figuring out the obvious.

Most normal women like being pretty, soft, and sweet smelling.

There is a world of ads and commercials, movies and romantic books all telling them that this is what being a woman is all about.

She has probably, from time to time, noticed that her ass is not always as sweet smelling as the rest of her body.

She might be afraid that when you pull your penis out of her, that something might be on the condom that will humiliate her to tears.

This is the biggest hurdle for most women when it comes to back door sex, and it’s a hard one to get over.

So, how do you do it? Well, there are two issues here that must be dealt with– the first is to reassure her that her ass turns you on, that it does not gross you out in any way. The second is to ENSURE that she knows and trusts that, no matter what, you are not going to humiliate her.

To deal with the first issue is fairly easy…

When you are having regular sex from behind, you should say to her how much her ass turns you on. You should even say, specifically, that her anus or ass-HOLE is the most perfect you’ve ever seen.

Yes, it will be weird to say.

Yes, it will be a little weird for her to hear. She may even laugh for a minute.

Then tell her how much it turns you on and let her feel your passion in your love making. Give her positive positive EMOTIONS and FEELINGS to go along with the words.

By the second time you do this, she will have a strong connection in her mind– “my anus actually DOES turn him on.”

She might even feel a bit of satisfaction or pride about it.

Next time try gently stroking it with your thumb and making an appreciative noise or telling her exactly how much it turns you on.

The good news here is that it is almost certain to really turn HER on too. It will feel VERY exciting to her.

And now her brain will have both emotional and physical connections between her ass and her erotic desires.

If she is really enjoying this stage, go ahead and try inserting a finger during sex. She might LOVE it. Either way, make sure she knows that it really turns YOU on.

Okay… now let’s look at the second part of the issue– Ensuring that she knows and trusts that, no matter what, you will not humiliate her.

This is more complex and more important than anything else in this Newsletter. And it is also one of the most important things to learn if you want to be an amazing lover that consistently rocks her world.

At the core of this is what I often refer to as “Sexual Trust” and it is something that you can establish very quickly…

But if you’ve already screwed up, it can take a very long time to win it back.

Sexual Trust is a complex issue that, all by itself, can make you the best lover she has ever been with– and it can ruin everything for her even if you know all of the “techniques and tricks” in the world.

Guys always get confused when I talk about Sexual Trust and mix it up with being “nice.”

Nice has nothing to do with it.

Imagine you are going in for dangerous brain surgery…

Which doctor do you trust to go inside your head with a knife?

The “nice” doctor?

Or the doctor who looks you in the eye and says, “I know what I’m doing. I was the top of my class, this procedure is easy for me and you will be fine, Mr. Smith.”

…And the thing is… your name ISN’T Smith… he got your name wrong. And the guy seems like an arrogant prick… But you can feel that he is completely confident about his work.

So which guy do you go with? The nice guy who remembers your name? …or the guy who really seems to know exactly what he’s doing and can get the job done?

You set up Sexual Trust by being sexually confident, by knowing exactly what you want and what you like, and not being shy or tentative about it.

You set up Sexual Trust by always making her feel like whatever she does and whatever happens during love making, you are never judgmental about it, you never make her feel weird, you never let YOUR insecurities make HER feel awkward.

You set up Sexual Trust by knowing EXACTLY what you are doing in the bedroom. (In other words, keep reading these Newsletters).

Okay, now you have the IMPORTANT information, I’ll go ahead and tell you exactly HOW you should go about having anal sex with her for the first time.

To begin with, and I hate to mention something kind of unpleasant… but make sure that she uses the bathroom first.

That’s right. You don’t want any strange surprises.

Second, a nice shower or bath might be a good idea.

As far as I’m concerned, this is a great way to begin for any kind of sex.

Once you have gotten her good and ready with foreplay, you’re going to want to begin by using your finger.

Either during oral sex or during sex from behind (doggy position), squeeze some lube onto your finger and gently insert it.

The more gentle you are now, the more easily you will be able to convince her that you are going to be gentle later. Patience is key.

Then, when you are ready, make sure the condom is secure and not torn, use plenty of lube, and then TELL her that you are going to stay still, that you will NOT THRUST AT ALL…

And then have HER gently back herself onto your erection.

This is such a good tip that I can’t believe I’m giving it away for free.

No matter how gentle you are– if YOU are controlling the motion, she is going to clench up, which will make it hurt for her.

But when SHE controls the motion, it is so much easier for her to remain calm and not clench that you will be all the way in in no time.

REMEMBER: When you tell her that you are not going to thrust, you have to be good on your word.

You can help guide it in, but no thrusting at all, no matter how frustrated you might get. Let her do it at her own pace.

Once she’s gotten all the way in and has experimented a bit with the in-and-out motion, you can then ASK HER if you can gently take over the motion.

And that’s all there is to it.

Congratulations, you have just introduced a woman to the pleasures of anal sex in an expert and confident way that she will always remember.

There is, as always, more I’d like to share with you because there are some more advanced ideas relating to anal sex that could actually get her HOOKED on it…

Including a position that, for some reason, almost always makes women come so hard that they vaginally squirt (female ejaculation).

Also, there is the entire subject of Sexual Trust– I glossed over it here because it is so important to this topic, but there is much more to it, and to really understand it is so crucial to learning the kind of sexual confidence that lets any woman know immediately that she is safe in your hands.

And that will allow her to have the most intense orgasms of her life.

This is also the key to bringing up any other sexual fantasies or fetishes that you want to try out, but that you are worried that she might think it’s weird or “get the wrong idea.”

When you know how to communicate sexually with a woman, none of those things are ever a problem….Unless you get off on something really freaky like watching women crush live animals beneath their heels (yes, there are guys that are into that)…

Other than that, chances are she is going to be very enthusiastic about whatever it is that turns you on if you understand Sexual Trust.

So, first of all, I hope that you will go out and actually try the things that I have talked about in this Newsletter.

They work. And they work well. But also I hope that you’ll continue to grow and learn and that your success with the ideas in this Newsletter will get you interested in learning the more advanced material that will make you a master lover.

Last thing I’d like to mention is that anal sex is not for everyone. If you are not into it, do not feel weird or like you HAVE TO try it.

You should do only the things that you really enjoy when you are making love.

Don’t worry that she might need something else to please her. She doesn’t.

If you are doing what you really enjoy, and you do it right, I promise that she’ll get off on it too.

Have fun, and play safe.


I have been fortunate enough to have been able to present a lot of great material in the cliff’s list newsletters and now on the website that have made a significant difference in many guy’s lives.

Leave a Reply