The Beginner’s Guide to Anal Sex

I’ve read a lot of articles here on Medium written by women who are anxious about anal sex. Many have had bad experiences and don’t want a repeat. Many more are scared that it will hurt, it will be messy, and so forth.

So here, for what it may be worth, is a Beginner’s Guide for men and women.

For the sake of simplicity I’m going to write as if the man is doing the penetrating and the woman is being penetrated, but it’s equally applicable for men on the receiving end too.

First some background info on why anyone would even want to try anal sex.

There are thousands of nerve endings in the anus and rectum, and so when properly done penetration of the rectum can be extremely pleasurable. Many women I’ve known have told me their most intense orgasms happen during anal penetration. It’s also emotionally intense, as the receiving partner surrenders their most delicate opening to the other person. This requires trust, and that trust must be honored for a mutually pleasurable experience.

Anal sex isn’t usually dirty. The rectum is merely a passage through which fecal matter passes from the lower bowel on its way out of the body. To be on the safe side a brief enema with warm water is generally sufficient to ensure that everything is nice and clean. Never use salt water or scented water or alcohol or soapy water or any other addition, as this will harm the delicate rectal tissues.

After cleansing, a little lubrication inside and out is always a good idea. Some people like artificial lubrication (for my money, Liquid Silk is unbeatable) while others prefer natural options like olive oil.

As it’s difficult to go from no penetration to full penetration in one leap, especially if the thing to be inserted is quite large, it’s best to work up slowly. There are many options for butt plugs on the market today. Personally I recommend clear Pyrex or similar, and you can often find these in inexpensive three-packs. Start with the smallest and work your way up.

Assuming you’re an anal virgin or at least very inexperienced, start with the smallest plug. After cleansing and lubricating your rear passage, slowly insert the plug yourself. Take your time, breath gently, and don’t force anything. Periodically squeeze your sphincter muscle around the object, hold the squeeze for a couple of seconds, and then relax. This will help train your body to understand that it can control the intensity of the sensation. Many people simple freeze up with anxiety, which makes penetration painful and distressing. By learning and practicing the squeeze-and-relax technique over and over, your brain and anus will become accustomed to penetration without fear and it will begin to feel pleasurable.

Work your way up from smallest to largest butt plug over a period of a couple of weeks. Do try to practice with the plug every day, and work up to being able to keep it inside you for around 30 minutes. If you can masturbate with the plug inside, even better: this will encourage your body to associate anal penetration with pleasure, and that’s the whole point of the act in the first place!

If you can then proceed to masturbating while using a suitably-sized dildo for anal penetration, this is excellent preparation for anal sex with another human. If you can feel pleasure and perhaps even cum while fucking yourself in the ass with a dildo, you’re definitely ready for the next step.

But this is where things become a little more complicated. Up till now, you’ve been in control. Now, you’re handing over control to someone else.

This means they have to be trustworthy.

I recommend agreeing in advance that you’ll attempt to accept penetration but if at any time you call “time out” then the penetrator has to withdraw. If you’re worried about their feelings or sexual frustration or potential disappointment you can always offer alternatives post-withdrawal. Or, you can make a second or third attempt before stopping until next time.

Assuming you are able to let penetration occur, the essential next step is for the penetrator to hold still inside you, once a couple of inches are inside. This gives you plenty of time to squeeze-and-relax, which incidentally will also feel great for the cock buried in your ass and is therefore no hardship for the guy involved. Slowly move to full penetration, stopping and using the squeeze-relax technique as often as you need. Once you feel ready, you can ask for gentle rhythmic penetration. At this point, use the muscle-knowledge you’ve gained from the squeeze-relax exercises to relax completely and stay relaxed.

You want your partner to be even more focused on your reactions than usual. It’s essential your partner knows when to ease off or stop altogether. This is especially important if the penetration is being done by a strap-on dildo rather than a flesh-and-blood penis.

Over time many people come to adore anal sex as one of several go-to activities that are most likely to yield intense pleasure. Many become so comfortable with anal sex that they welcome a good hard fuck in the ass and rarely have to worry about being hurt. Everyone is different, so take your time and let your body tell you when you’re ready to move to the next stage.

As you embark on your journey your mind will likely keep saying “I’m not ready yet!” but that’s fear talking, just as fear tells us we aren’t ready to go to the dentist or ready to try skydiving or anything else that puts us outside of our daily comfort zone. Still the mind and listen to the body and go at the pace your body is comfortable with.

And then be prepared for a pleasant surprise!

Anyone who enjoys my articles here on Medium may be interested in my books Why Democracy Failed and The Praying Ape, both available from Amazon.

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