Learning to Enjoy Anal Sex
First published March 20, 2014
© Max Private – All rights reserved

Image by Claudio_Scott


Learning to enjoy anal sex is an issue that comes up again and again. If you are not into anal you may be asking why should you? Those who are into anal are asking why not? Those who want to please or share this experience with their partner are asking how can I?

So far, I am yet to see this subject addressed effectively. I see a lot of quick advice that lack any explanatory depth and only deal with one aspect or another. Some focus on one practice technique or another or they provide blind pieces of advice saying use more lube, taking it slower and just relax. All of which are good pieces of advice but not helpful it you believe your are already doing these things. Furthermore, this type of advice is treating symptoms and not addressing the root cause of many people’s discomfort.

Many, including myself, provided advice to people in detail with the physical or mechanical issues of preparation, cleaning out (enemas or not), muscle control, technique and channel (colon) navigation (Anal numbing agents, Avoid the pain of anal penetration, Anal Sex Problems, et al), but what about mental preparedness and how to relax, or better yet, identifying when you are not relaxing? Let’s see if I can get to the crux of the issue right now.

Sexual pleasure not automatic

I don’t think there are many people left in the world that do not understand that a woman’s vulva and vagina is wired for pleasure. More specifically the bits called the clitoris and the G-spot. Despite the wiring to these pleasure centers, very few women experience an orgasm from their first penetration. In fact braking the hymen is down right painful for most. They are not likely to get the big O from their second or third penetration either. Sadly, there are women who never experience the big O at all, although that is becoming rarer and rarer thanks to the emancipation of women and the sealed section in Cosmo magazines (to wit: Why sex might hurt for you).

Despite all these hurdles, women keep having sex even if they don’t enjoy it. In some cases it is just social and peer pressure pushing women to it, but in most cases there is still a lot of pleasure to be gained from sexual intercourse with a partner as well as the ongoing hope of achieving the big O.

Why should anal sex be differnet?

So moving on to Anal. Make no mistake, bowl movements are wired to trigger your pleasure responses. This is why some people, men and women, have anal orgasms from straight forward anal penetration. Anyone can have better orgasms when they have their ass stimulated, but not if your mind is set against it. Nor can you expect that developing a love for anal sex will be easier than a woman’s quest to enjoy vagina sex. But that doesn’t mean you just have to put up with the pain or discomfort you might feel until you figure it out.

Women might be thinking, it still wasn’t this hard coming to terms with vaginal sex. “Why is it so hard to get started? “What’s causing all this pain and discomfort when I don’t have a hymen to worry about?

Arresting the fight or flight response

At the seat of everyone’s problem (men and women) is the human “Fight or Flight” response. The human Fight or Flight mechanism is wired directly to your ass (literally). Along with many other parts parts of your body. If you give someone a big enough fright they will literally shit themselves (as well as pissing themselves) uncontrollably. Hence the phrase. This is a very primal reaction designed to lighten the load and eliminate any distraction from your next reaction.  Either you’ll be running for you life or fighting to the death. Anything short of “oh shit, I am going to die” will make your ass shut tighter than Fort Knox.

Any trepidation, fear, concerns, anxiety, nervousness, stressed, etc., that is lurking in the back of your mind will tence the mucles in your anus. Even stress not related to the thought of having anal sex. Anytime you stretch or force a clenched muscle you will experience pain. Worst case, you will actually tare the muscle, resulting in aches and pain for days. This stress/anxiety issue is also why you will find anal was easy on pasts occasions and at other times it is impossible.

Any muscle will relax if massaged correctly, usually in conjunction with soothing our mind. Not always the case with anal massage. If someone or something touches your ass when you are not ready for it, your sphincters will clench. This is the Fight or Flight response. Your ass to pucker up and shut tighter than a vice before you even have a conscious thought on the matter. When you are use to having your ass touched, the right touch will relax and open your anus. The first step in learning to enjoy anal sex is for you (and your ass) to become use to being touched.

Being clean is a big advantage

Learning to enjoy anal sex or anal play of any kind usually starts with addressing the issues of cleanliness and hygiene. This does top most peoples list of issues with anal. But cleanliness and hygiene leads to quite a bit of discussion on its own and distracts us from dealing with the neurological issue and it is the neurological issue(s) that I do not see people addressing at all. So I will deal with cleanliness and hygiene separately.

So if we take the position that cleanliness and hygiene has been addressed because it is actually pretty easy and straight forward, and there can be no objection to anal play on these grounds then simply becoming accustom to having your ass touched turns out to be a bigger issue for most.

Accustomizing to the new sensations.

There are a lot of ways to start becoming accustom to having your anus touched. Not the least of which is the process of making it clean for further play. After that you need to become accustom to something being inserted something and something holding your ass open. Becoming accustomer to something thrusting in and out is sthe last step. All new sensations and all capable of triggering your Fight or Flight response.

Any new sensations in your ass can re-trigger the Fight or Flight response causing everything to tense up. Suddenly there is pain. After you have experienced pain your mind will go into Fight or Flight mode in anticipation of pain. So, the next time you try something it will seem harder than the last time. It will seem like you are going backwards.

So be ready for set backs. Its OK to push your boundaries a little each time you play. Buy don’t press on just because you reached some mile stone last time. Be prepared to back up a bit when needed. The idea is to get your mind and body accustom to these new experiences. The more you avoid hurting yourself the faster you will learn to enjoy the sensations, going bigger and deeper.

Anal is always easy with practice.

To wit, here is one person’s account of their journey after reading this advice.

“It didn’t hurt!”

“Every time my boyfriend and I have ever done anal it has always hurt at least a little bit (felt like burning) as I stretched to accommodate him. Last night was the first time he was able to slip in without any pain or discomfort at all.”

“It simply takes time and a willingness to keep trying. My partner and I shower together every night before we go to bed, and he began fingering me for a bit every time. We’ve been doing this for about two weeks now, but we have had anal sex maybe a half-dozen times before, roughly every three weeks for the last four months or so (no play or stretching in between at all).

At first one finger would barely fit comfortably, but with repeated stretching I was able to accommodate two, then three, and bam! We’re having sex in the shower and it was amazing! Two weeks seems like a short time, looking back on it, but we didn’t rush and just let it happen, so it worked for us. If someone is scared about trying anal, I really recommend this, or toys, to prepare. I never truly realized how much it helps.”

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