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Anal Sex: A Must-Read Beginner's Guide

Posted by Carolyn Eagle on

Anal sex is a topic that was pretty taboo even 10 years ago but has now become the hottest trend for adventurous folks who want to experience a new kind of pleasure. What used to be something you would only see in porn is now getting the mainstream treatment in movies and tv, which has plenty of folks wondering what all the fuss is about. 

Don't worry, we at Naughty North have your back (so to speak). We have put together a comprehensive guide to take you from anal curious to anal lover in no time. 

Before we get started though, we want to make it clear that anal sex is not for everybody and you should never feel pressured into trying something during sex that does not meet with your wholehearted enthusiasm.

Here's a breakdown of the guide to make it easier for you to navigate:

What Does Anal Sex Feel Like?

Anal sex has several stages of feelings from when you first get started to when you achieve full penetration. If you are starting small with a finger or small plug and plenty of lube (which is a MUST), then the teasing of the anal muscles can feel extremely pleasurable if a little strange. 

Anal penetration can feel like pooping in reverse or like you need to have a bowel movement when you don't. That is the stimulation and contraction of the anal muscles. This kind of feeling is what turns off a lot of folks from exploring further, but if you are well prepared, then you should try to relax into the feeling and embrace it because it can also feel incredibly pleasurable. Starting small can also get you used to this feeling before you move up to bigger things.

Without proper preparation, you may also feel some stinging and burning at the beginning stages of penetration. Our advice is to stop, back up, apply more lube and try again with something smaller. Anal sex should not hurt and "powering through the pain" is not safe and can lead to tears or fissures. 

Once you do manage to achieve comfortable penetration, anal sex can feel amazing. Of course, there is the sexual thrill of something new and taboo but there are also a huge number of sensitive nerve endings in the anal sphincter that give a lot of pleasure when stimulated. 

Prostate stimulation has been compared to the g-spot for females, and stimulation through anal penetration can lead so more intense and longer orgasms. For females, anal stimulation can also stimulate the vagina, since the rectum runs right alongside the vagina internally. Anal penetration can even stimulate the internal parts of the clitoris leading to a head to toe blended orgasm. 

It’s a process, we’re not going to lie about that. But you’d be surprised to discover how amazing it can feel with some practice and patience. So to help prep yourself up for it, let’s look into detailed guidelines of how to prepare for anal sex.


How To Prepare for Anal Sex?

Congratulations for reaching this far! Even if you’re not 100% decided on attempting anal sex, we know that the curiosity and interest is there. And sometimes, curiosity can take you as far as you let it--so let’s begin to satiate your thirst for information.

Pre-Game Prep:

1. Watch What You Eat

If you are attempting anal sex for the first time, then we recommend you plan for it in advance to ensure maximum comfort and enjoyment, whether you're going alone or with a partner. Avoid having a heavy meal beforehand, and steer clear of foods that may have given you gastrointestinal upset or loose stool in the past. Simply put, you may want to avoid anything that will make you gassy or give you loose stool before trying anal sex if you are at all worried about these things. 

We also recommend that you try anal sex for the first time sober. That goes for yourself and your partner. While alcohol may lower your inhibitions and help relax you, too much can hinder your ability to feel what is really going on. This is particularly important if you are experiencing anal with a partner who is going to penetrate you. The penetrating partner needs to be 100% in control of their movements and have the ability to go slow and stop if you require it. 

2. Clean Before You Go

    Anal sex does not actually require douching, but if you are at all squeamish about the thought of a little poop, then you can purchase simple, reusable, douche/enema bulbs that will help clean out your lower rectum. 

    In actuality, there is little to no feces in your lower rectum, so if you make sure you have had a recent bowel movement and clean your anus thoroughly in the shower beforehand, you should be fine. 

    3. Must-Have Condoms

    Even if you’re in a monogamous relationship, wearing condoms still comes highly recommended. This is to prevent infection and the spread of bacteria from the bowels into the urethra of the penetrating partner. If you are using a dildo, we also recommend putting a condom on it. Only silicone, glass, or metal sex toys can be thoroughly disinfected, so you should not use a dildo for anal sex that you will at some point also use for vaginal penetration, unless it is made of one of those materials. 

    Of course, lubricated condoms are going to be helpful during anal penetration but in reality, they do not have nearly enough lubrication to make anal penetration comfortable. And that leads us to...

    4. Choosing the Right Lube

    What you are looking for with anal sex is a thick, long lasting lubricant - and plenty of it. Silicone lubricant is fantastic because it is condom compatible and will not dry out, which means you don't have to keep reapplying and you are going to get a nice slide. The drawback of silicone lubricant is that it does not play well with silicone sex toys. If you are using a silicone butt plug or dildo, you may want to choose a water based lubricant made for anal play, or a silicone/water hybrid which has just enough silicone for extra slide but not enough to harm toys. 

    What you DO NOT want to use is any type of oil. That includes oil based lubricants, including the ever-popular Vaseline. Not only are they difficult to clean up, but they will break down the material of your condoms and cause them to tear. 

    Just remember, that there is not such thing as too much lubricant when it comes to anal sex. 

    5. To Sex Toy or Not to Sex Toy?

    Should you or should you not use sex toys? The answer to that question is: it’s up to you. Anal sex toys are beneficial when it comes to teasing and preparing the opening, especially since these are specially designed to fit and stimulate that part of our body. Surely you can also just use hands but if you do have the time for it and if you want to add some spice and some more fun into the whole experience, then you might as well go the extra mile with some helpful anal sex toys.

    It is incredibly important to remember that not every sex toy is made for anal play. Anal toys have a flared base which is there for safety. The sphincter muscles are incredibly strong and they will pull toys into the body which will get stuck and require a trip to the emergency room. The flared bases on anal toys are there to prevent this from happening. 


    Top 3 Essential Ingredients:

    1. Communication

      More than anything else, if you are having anal sex with a partner, communication will be the key to success. Being able to vocalize your apprehensions and expectations can help a lot to make the experience more enjoyable for the both of you. 

      During your sex play, good communication is going to allow you to let you partner know when to stop and start, how fast to go, and if you are feeling uncomfortable. This is particularly important if your partner is using a strap-on to penetrate you since it can be difficult to judge how much pressure to apply during penetration. 

      2. Lubrication

      We couldn’t stress enough how important lubrication is during anal sex. With no natural form of lubrication to work with, you will need to find something that works well for you and your partner. Even if you have used a lubricant before during vaginal penetration or for masturbation, it may not be the right formula for anal. 

      We recommend picking up a lubricant made specifically for anal and using that to start with. They are formulated thicker to make penetration easier. 

      Anal lubricant should not be mistaken for anal relaxant or numbing products, though. Those products will cause a temporary reduction in sensation around the anus and "relax" the muscles for penetration. The danger, however, is that if you are unable to feel what is going on, you are more likely to become injured. Anal fissures and tears are a real possibility if you can't feel any discomfort that may be happening. 

      Let’s get real, lubes are a small price to pay for the pleasure you can reach. We highly suggest you at least have two to three on hand that you can try out whether you’re just teasing or fingering or using toys onto actual penetration. I

      3. Relaxation

        The key to anal play is relaxation and the key to relaxation is plenty of foreplay. The more aroused you are, the more you are going to be able to relax your muscles and allow penetration. 

        So... How we start?

        Start small

          As we’ve said before, a big part of anal sex is the prep that comes before it. This includes use of fingers, tongue, and sex toys to help in easing into anal sex. If you really want to prepare for it, butt plugs would be a good start and you can use it during vaginal sex as well.

          Breathe and relax

            The sphincter muscles are incredibly strong and made to resist things entering rather than exiting your body. Deep, calming breaths will help as well as plenty of foreplay. If you are tensing up, that is a sign that you should back up and try again some other time or enjoy some more foreplay. 

            Enjoying anal sex has a lot to do with what is going on in your mind. If you are confident, willing, and prepared, you should have no problem enjoying this new experience.

            The tip is the hardest part

              If you are using a dildo for anal sex, then look for one that is slender at the tip for easier penetration. With your partner's penis, you don't have that option so the penetration of the tip of the penis will be the most challenging part. 

              You are going to feel stretching and pressure as the tip eases in, but if you bear down and your partner enters very slowly, you should be fine. Apply tons of lubricant both to your anus and the dildo or penis and try gently nudging it against your hole until bit by bit you will start to feel penetration. 

              No rapid fire movements

                Penetration is best done in a slow and steady motion, or with a gentle rocking of the hips, which is where communication with your partner really comes in. You need to let them know how you are feeling minute by minute and inch by inch to ensure your comfort. 

                This is particularly important if you are using a dildo to penetrate your partner, since you will have no way of really feeling how much pressure you are applying as you push in. 

                Stimulate in other parts

                Having an orgasm through anal sex alone can be difficult at first for the receiving partner. While prostate stimulation through anal sex is intensely pleasurable, it can take practice and patience to find just the right angle and spot that works for you both. The same applies to the female body. While anal penetration can stimulate the adjoining vaginal canal and even the deeper internal parts of the clitoris, many women need direct clitoral stimulation to achieve orgasm. 

                A sex toy such as a vibrating bullet held up against the clitoris or a vibrating cock ring on the penis can give the receiving partner that extra bit of needed stimulation to achieve orgasm. 


                Top 5 Best Anal Sex Positions

                While there are possibly an endless number of positions you can experiment with during sex, there are certain positions that are going to give you more control and comfort as an anal beginner. Here are ones we recommend and why:

                1. Missionary

                  Given some adjustments here and there, the missionary position can prove to be an amazing and optimal position for anal sex. The first thing to do is to prop the receiver’s hips with a pillow to get a better angle. Raising the legs or placing it on the shoulder of the partner would also help in smoother movements. 

                  What’s great about the missionary positions is how both you and your partner can easily gauge one another’s movements, responses, and feelings. And given the sensitive nature of trying out anal sex for the first time, it’d surely be helpful to have that open view of each other.

                  If you find the elevated hip position difficult to maintain, there are some great sex bolsters available that can help make you more comfortable. You can also scoot your bum to the edge of the bed and have your partner penetrate you while standing.

                  2. Doggy Style

                    Doggy style is the most basic position for anal sex and usually the starting point for a lot of couples. The control in this position completely relies on the partner who’s going to penetrate. It’s important that to just relax if you’re the receiver. You can never go wrong with starting slow to easily gauge the speed and depth that you’re both comfortable with. 

                    To make things even better, once you get the hang of it, have your partner reach out to your clit, breasts, or penis more stimulation. You can also go lower and have your chest and face laid out on the bed with your hips propped up. Again, it’s all about the position that gives you that smooth sailing rhythm.

                    3. Cowgirl / Cowboy

                      A lot of people prefer the cowboy position because of the control it gives them. All there is to it is to have your legs on the mattress, placed on both sides of your partner, and have your hands on their chest for your balance. You can go up and down or front and back, even sideways or going round and round. Remember that this position is all about you taking charge of the pace and depth. 

                      4. Reverse Cowgirl / Cowboy

                        It’s the cowboy but with a better view for your partner, with you facing away from them while straddling their hips. You still have control since you’re on top but they get to watch you being penetrated, which is incredibly erotic. If your partner sits up, they can reach around you for extra stimulation as well. 

                        5. Spooning

                          If shallow penetration and maximum contact appeals to you, spooning may be just what you need. Your partner will hold you close and enter from behind, maintaining a slow and sensual pace. As the receiver, you can also place your leg on top of your partner's to help create more leverage. This is a great position to allow your partner to reach around and stroke your chest, penis, or clitoris. 


                          Dealing with the Aftermath

                          While you may want nothing more than to cuddle after sex or nod off into post-coital slumber, anal sex requires a bit more after care. Let's face it, anal sex always has the potential for a bit of feces to become involved so a thorough clean up is in order for you, your partner, and your sex toys.

                          For the receiver (the person who was penetrated), you should give your anal area a gentle wash to make sure you remove any lubricant or fecal matter that may irritate your skin if left there. Be gentle, since the skin around your anus may be a bit sensitive.

                          For the person doing the penetrating, you should also give your genitals a gentle wash, even if you used a condom (which we really hope you did), to ensure no bacteria or fecal matter is left behind. If you chose not to use a condom, a thorough wash with soap and water is critical to prevent infection.

                          If you used a sex toy of any kind, you can clean it with warm water and soap, or a sex toy cleaner as soon as possible to avoid bacteria growth. Silicone, glass, or metal toys can usually be boiled or submerged in a 20/80 bleach/water solution before you use them again

                          Additional Safety Tips & Points to Ponder

                          • Smoothness is the best policy - Cut your nails, no ridges on sex toys, and so on. These are the basic golden rules regarding anything that you put inside the anus. Simply put, the smoother, the better, until you gain more experience.
                          • Cleanliness is next to godliness - Cleanliness before, during, and after must be strictly observed at all times. 
                          • Never do without the lube - We cannot stress the importance of lube enough! This applies when inserting just fingers, or sex toys, or a penis.
                          • Use the correct toys - Anal sex toys must have a flared base so they don't become lodged in the rectum. You don’t want to have a sudden trip to the emergency room. 
                          • No transfer allowed - Never transfer a toy or a penis from the rectum to the vagina. If you think you may want that kind of play, cover the penis or toy in a condom, then switch condoms when you switch holes. 

                          With all that said and done, we sincerely wish you a happy and pleasant experimenting! And for any assistance needed, you can check out our line of toys that would work well for anal sex such as lubricants, butt plugs, prostate massagers, dildos, condoms, and so on.  And if you need further advice you can always catch us on our live chat or send us an email. 


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