Here is a question someone asked me that’s like many I’ve been asked.
I am very inexperienced with anal play. I attempted to have anal sex with a very hot guy last night and was made ashamed because I had difficulty being penetrated.
Can you provide me with a lesson about the basics of anal sex?
In desperate need of your help.”
– Name withheld for privacy
Although modified slightly to protect privacy, this real inquiry taken from my inbox is an example of the thousands of questions I’ve received that ask pretty much the same thing about anal sex.
Here’s my response to this anal sex question
I’m glad you reached out, and the first thing I want to say is to offer a generous dose of friendly compassion (and if you might like, a hug) for that unfortunate experience of feeling shamed by this guy.
Start with self-compassion
If someone criticizes your inability or shames you, a good response is to have self-compassion.
Then, it’s often helpful to talk with them about what you need in order to enjoy anal erotic pleasure with them.
If your partner is not open to being reasonable in how they talk with you and in their expectations, then you may need to find someone else with whom to share anal pleasure.
Compassion for yourself and taking care of yourself emotionally is important.
Don’t let the fact that someone has a hot body get in the way of that.
Choose anal sex partners who are realistic
It’s normal and healthy if your partner has a feeling about your sexual abilities or inability, such as you’re the difficulty you had being penetrated.
Whether it’s an ongoing relationship or casual sex, hopefully your relationship with your partner includes enough emotional bonding and mutual respect that it’s OK for them to share their feelings with you – in a kind and respectful way – including about this.
However, it crosses the line when honestly sharing feelings is mainly about blaming or judging rather than bonding through emotional openness.
This applies whether it’s because you lack sexual experience, ability or even just had a bad butt day (something that happens to even the most experienced anal sex enthusiasts).
This points us to the importance of choosing sexual partners who you’ve got the sense know how to be compassionate and non-judgmental when things do not go perfectly. Just because someone looks hot does not mean they will be able or willing to do that.
Good anal sex takes time and practice
It’s very common for people to not be able to be penetrated when they first try, especially if they don’t have much experience with solo butt play.
Good anal sex is one of the most complex and time consuming of all sexual acts. It requires preparation, effective communication, slowing down, relaxation and communication, and an understanding of how the anatomy works.
The truth is that being comfortable being anally penetrated takes time and practice – including lots of solo practice.
Hardly anyone is very successful the first time they try to play the violin or go ice skating. The same goes for anal sex.
The good news is that if you pay attention to what feels good and go slowly, you can learn to enjoy anal touch and get a great deal of pleasure from being anally penetrated.
Porn is very misleading about good anal sex
When it comes to anal sex, porn will greatly mislead you. It’s made to look hot, not to teach.
Most porn videos, still photos and many erotic stories simply do not show the preparation, practice, communication, and effort that goes into pleasurable anal sex with a real person.
To be penetrated, many porn actors use drugs that block them from feeling their body. Aside from the many dangers to anal health, this blocks pleasure. This leaves one with only mental and visual pleasure. As valuable as those things can be are tiny compared to the transformative nature of physical pleasure possible from good anal touch.
A few porn stars might be skilled at anal sex from lots of practice. However, the priority in porn is a hot looking body, not sexual pleasure or ability. If you pay careful attention, you’ll see that often porn actors do not enjoy being penetrated.
A lot of anal sex in porn is simulated. Careful staging, cuts, simulated penetration, shooting from creative angles and other edits are used so that it looks like a large penis or toy was inserted fully and deeply and pleasurably.
While this is possible for some people, it’s not for many, even many porn actors. Careful examination of porn clips often reveals that it may not have been inserted at all, or only just a little.
Hookup sites don’t teach good anal sex
The photos and conversations on hookup sites often reinforce the idea that anal sex that feels great is effortless.
People only upload their best selfies. It’s hard to capture the preparation, communication and relaxation necessary for good anal sex in photos.
On many discussion forums or in their profiles, many people who talk about anal sex want to insert large penises or toys. Take this with a grain of salt, since many of these people have not actually done so successfully. Or they may have done so but only painfully.
Many even believe incorrectly that pain is a necessary part of bottoming for anal sex. It’s not.
Good anal sex might include a moment of mild discomfort, with an emphasis on brief and mild. It never needs to be painful.
Many anal sex tops have unrealistic expectations
Whether you are straight, bisexual or gay and whatever your gender, you will find plenty of tops (givers or insertive partners) with expectations about anal sex that are completely unrealistic. Usually this is due to ignorance and sometimes selfishness.
Often such people have never been on the receiving end of anal play. Their attitude would likely change quickly if they were.
Any anal sex top who has not learned to and personally enjoyed anal sex as a receptive partner (bottom) has no business criticizing you for not being up to their expectations.
Carefully note that I said “enjoyed.” Just because someone may have bottomed occasionally or once many years ago, does not make them a good choice for an insertive partner (top).
The bottom line is that tops who have not enjoyed receiving anal touch are usually less skilled at anally touching, pleasuring or teaching a bottom.
In certain communities, such as among gay men in many regions, there is a great shortage of tops. Thus, they often get away with being unrealistic. Due to the supply and demand issue they may not even realize how unrealistic their expectations are.
Enjoy anal sex more by learning to relax deeply and manage life stress
The better you are at managing stress, in all areas of your life, the more likely it is that you can enjoy receiving sexual touch anally.
A lot of the stress we experience in life shows up as muscular tension in the pelvis. There are many muscles that cross the buttocks region and connect near the anus and rectum.
Like all muscles, when you feel stressed they will tighten up. If you are chronically stressed they might become chronically tight.
This muscular tension will affect your ability to be anally penetrated and how much pleasure or pain you get from it.
The better you can learn to relax your whole body, and to be more relaxed about the challenges that life brings your way, the easier it will be for you to enjoy bottoming for anal sex.
Enjoy solo anal pleasure regularly
If you want to be the happy, receptive partner for anal sex, then you need to enjoy solo anal sex regularly.
Anyone who is going to run a marathon or play a competitive sport will tell you about the importance of practice. Musicians know the importance of practicing before giving a concert or recital.
The same concept applies to anal sex. If you want to enjoy it with a partner, you need to be able to enjoy it by yourself.
Get to know your body. A good place to start is with the simplest of self anal massage. Insert a finger when you’re in the shower. Psychologist Jack Morin, author of the book Anal Pleasure and Health: A Guide for Men, Women and Couples, recommended people do this every day.
Whether it’s anal massage or anal sex, only do what feels good
The key point in this simple anal massage (just like with any type of anal intercourse) is to only do what feels great.
Notice what you like. What feels great?
Explore more of that.
If it hurts that’s your body’s way of telling you that you’re doing something wrong. You need to slow down or stop, or trying something different.
If your partner is not on board with this pleasure based approach to anal sex, then it’s probably not worth your time and effort to engage in anal sex with them.
The bottom line on bottoming for anal sex
If you’re inexperienced and uncertain how you can enjoy being penetrated anally, the place to start is by having realistic expectations. Then, make sure the partners you choose for anal sex have realistic expectations as well.
There is a lot you can do to begin to enjoy receptive anal sex. First and foremost, assess and change the unconscious assumptions you’ve taken from porn and hookup websites. Work on developing ways to relax your whole body. Explore and enjoy solo anal touch on a regular basis.
As you focus on these foundations of healthy and pleasurable anal eroticism you will become more able and ready to enjoy anal sex with a partner.