Complete Guide to First Time Anal Sex (2020)

If you rule out the possibility of anal sex in your life, then you might be underestimating the power of your rectum to provide you with the highest realms of pleasure.

Well, you are no longer living in a world where sex is considered a subject of taboo.

We talked to a lot of women about their anal sex experience and learned how they decided to embark this journey.

They welcomed the experience because it helped enhance their sexual repertoire.

first time anal sex

Many people surround anal sex with several myths, while there are tons of other people across the world who pleasure themselves with the same. For those who haven't tried anal sex, there could be some daunting thoughts going on in your mind.

But we suggest you come outside of your clean vanilla sex shelter and be a part of something new. We understand all your concerns related to what to do and how to do in the beginning, middle or the end.

This is why we are going to hand over you a complete guide to first time anal sex to make it easier for you.

The sensation of Anal Sex - Sensual than Regular Vaginal Sex or not?

Well, anal sex is something that ranges from taking in some pressure to dwindling around, ultimately resulting in an overwhelming climax. You might feel like you need to poop but trust me, you won't do it. Such feelings come up when the penis is inside you.

At the time of insertion, you might feel a little bit burning and stinging. No one will tell you the actual feeling, and we are obviously not here to scare you off, but this is the truth.

So, you must be wondering why do people do it then? Well, the answer to this question lies inon the fact that once you get used to these rough starts, it can be a lot of satisfying, stimulating and addicting.

Ask a Pornstar - My First time Anal Sex Experience

Do focus on the word "addicting" because it is unlike any other experienceinfact, it is more intense than your vaginal orgasm. One obvious thing about anal sex is that it might take more than one attempt to finally start feeling pleasurable.

Hence, always remain patient if you're starting fresh with anal sex.

We won't lie about the process, but you will be surprised when you actually discover that it could give such a fantastic feeling once you push through its details. You may need to prep yourself up, and you will be good to go then.

Let us take a look at the detailed guidelines which will help you in preparing for anal sex. 

Preparation for Anal Sex

Well, we totally appreciate if you have reached at this point because we know that you have some curiosity and interest in going for anal pleasure. This is a great thing because curiosity often lets you dive into the most incredible experiences. Let's get started. 

1. Be careful on your eating habits.

Mexican and spicy food must be avoided at all costs prior to the anal sex. 

If you do otherwise, it could seriously be an embarrassment because you will inevitably end up making a mess and we are talking about a shitty mess. You need to avoid foods such as spicy or Mexican food which would make you lose some stool.

Also, avoid eating some heavy food before any type of sex,; vaginal or anal, because you won't feel good throughout the sex.

What about drinks?

There has been a lot of debate about the drinks as some people say that it might help you calm your nerves while others say you have to be completely sober. Our recommendation depends on the circumstance.

If you are a "giver", then you need to stay sober all the time because you will then be able to control your movements better. However, if you are a "receiver", then a little liquid might help you gain some courage if this is your first time.

A small sip will relax your body as well as the mind, but a lot of quantity of drink is not at all recommended.   

2. Clean up is essential before the action.

There is no point in going extreme and then be called douche for not cleaning yourself up.

This is a good habit and certainly an essential step in preparing for the anal sex. Cleaning your portion is similarly like taking a shower, but you need to put more emphasis on your buttholes while you cleanse yourself up. 

No one will tell you about some things like the lower portion in your rectum always has some of the fecal matter. You need to go through a detailed cleanup on even the shallowest of portion;, and then you will be good to go. 

Cleaning Out for Anal Sex

3. Condoms are necessary.

Even if you follow the principle of soulmate with your special one, we recommend you wear condoms.

This helps you practice the methodology of safe sex which initiates the concept of preventing infection from bacterias or viruses. One essential things to consider is that condoms tend to offer some lubrication which ultimately helps you in easy insertion.

This is required because the rectum doesn't have the ability to self- lubricate as the vagina.

3. Condoms are necessary.

Even if you follow the principle of soulmate with your special one, we recommend you wear condoms.

This helps you practice the methodology of safe sex which initiates the concept of preventing infection from bacterias or viruses. One essential things to consider is that condoms tend to offer some lubrication which ultimately helps you in easy insertion.

This is required because the rectum doesn't have the ability to self- lubricate as the vagina.

4. Selecting the right lube.

If you don't have any idea about lubes and other associated materials, then silicone based lubes will be a great choice for you as it tends to work well with the condoms and is quite safe for your skin.

If you are using water-based lubes, then it may easily get dried up, and oil-based lubes tend to break off the condoms. This is why we suggest you try the silicone lubes to ease a good deal of penetration. Remember the fact that there is a myth about "a lot of lubrication".

There's no such thing as "a lot of lube"; just start with a good amount of lube and lubricate more if you feel it is necessary.

5. Sex Toy or Not?

It is totally up to you if you want to use sex toys. Anal toys can prove to be a great deal of help when it comes to preparing the opening. The sex toys come in many shapes, sizes, colours and functionalities. Since you are a beginner, you can get your hands on the starter toys.

However, if you have a dreaded thought of using a toy, then let your fingers do the job for you. You can go ahead in trying a comprehensive sex toy to add a little spice in your anal sex life and have some fun.

Once you become used to the anal sex, you can use these toys for going a little extra mile on your sexual journey.

Doc Johnson Triple Anal Butt Plug Set

A set of butt plugs.

One excellent category of sex toys for anal play are Butt Plugs.

Butt Plugs put pressure on the inner wall of your anal canal to provide you with utmost pleasure. After getting around and talking to some people, we got to know that many women and men use butt plugs while playing solo?

Some people also suggest warming up your butt hole before engaging in anal sex.

However, choosing an excellent butt plug holds great importance, and if you found a suitable butt plug along with a good lube which works well for you, then you should consider yourself lucky.

There are a lot of butt plugs present in the market, but it is up to you to choose the best butt plug for yourself as these come in different shapes, sizes and colours. You should give yourself a butt plug which works well for a beginner.

If we put simply it should be narrow in the front, wider in the middle and again with a slim neck to give you the necessary pleasure which you deserve.  

How can you select your first butt plug?

There are some do's and don'ts to do a particular task. If you are getting on to buy a butt plug for yourself the very first time, you should consider the things given below:


  • As a beginner, you should always start with a toy which is small in size and which doesn't have any textures i.e. which is smooth.
  • These toys come with different bases, but we recommend you try it out with a butt plug which has a safe flared base.
  • These toys come within different bases, but we recommend you try it out with a butt plug which has a safe flared base.
  • However, before buying the butt plug, make sure you purchase some lubricants as well to enhance your pleasure.
  • You need to keep calm and start slow, otherwise, things may get rough, and you might end up in an unpleasant situation.
  • Do remember to clean and sanitize the butt plug once you are finished using it. 


Don’t overestimate your butthole's capability and buy some large butt plug with a gigantic diameter / insertable length.

You should never force your body by doing something which might get messed up later on.

  • You should not ignore the pain if you experience it at some point in the act. After removing the toy, if the pain still persists, you should consult a doctor immediately.
  • Stay away from the butt plugs, which are textured in design or use some low-quality materials.
  • You should not trust a fancy butt plug that doesn't have any base / small base.
  • You should not buy your butt plugs from eBay, Amazon or other third party unreliable websites. You should always consider buying them from established agencies. 

Choosing a butt plug must be a crucial concern; if you don't want to visit the ER. So, choose wisely otherwise try talking up to your partner about it, which is an essential ingredient of the anal sex. Want to know about it? Well, scroll below.

Essential Ingredients of anal sex

Ingredients are the small components which can impact the whole process as well as the end result if not taken seriously.

Similarly, for a healthy sexual life, you need to consider essential ingredients that make it spicy and content. We are listing the top three essential elements leading to amazing anal sex.


Even though you have done all the preparations before the anal sex, it becomes necessary to communicate with your partner about what you want or what he wants.

You both need to take full responsibility for the apprehensions, worries, expectations and even the complications. This can help to make it an enjoyable experience for both of you. If you are the receiver, then you need to keep calm and maintain a state of Zen.

If you haven't been communicating about your thoughts and feelings, then you might end up in pain.

You might even struggle to get things sorted out. Get the necessary talk beforehand so that you both come out as winners as well as satisfied.   


We cannot stress enough on the importance of lubrication during anal sex.

Unlike the vagina, your rectum can't lubricate itself, and this is where a lube plays its crucial role. Finding the right lubrication can be a tricky subject but some recommendations from the expert can prove a lot more helpful. It’ll help ease the process and make it pleasurable for you. ​

Keep two to three kinds of lubes handy and use the one which suits your needs the best.


Once you have communicated your thoughts to your partner and have found the perfect lube, is it a good time to dive into the action now? The next ingredient is just relaxing and feeling good.

There can be no other way to relax and enter a Zen state of mind than having a gift from your partner. This is something incredible and the best possible way for a pleasurable sexual experience.

If everything goes well, it is the time to act, but you need to start slow and don't rush into things; otherwise, things may get wrong. Therefore, we recommend you take a stride. To work things out, you and your partner need to be in complete alignment.

In the later section, we will be guiding you to each and every step of the process.   

First Time Anal Sex - Let's Start the process

You might not remember your first walk as that was during the time of your childhood, but you will never forget having your first anal sex.

We know that you want everything to go normal otherwise it would be a bit disappointing, wouldn't it?. Now, there must be few dangerous thoughts going on in your head, and we suggest you take a deep breath. Don't worry as we will be here talking about the whole process bit by bit. Let's go.

Start with one thing at a time

As we already discussed before, an essential element of anal sex is preparing for it.

You can get yourself into some action with your fingers and sex toys which will help you ease through the anal sex. You might be considering using butt plugs (which we discussed in the earlier sections). We recommend you to let it stay during vaginal sex as well to experience more pleasure.

Breathing and Relaxing   

An important thing for a successful penetration is relaxing your sphincter muscle as this sensitive muscle is involved in opening and closing up your buttholee. This is why we keep on emphasizing relaxing because if you feel anxious, then it might get tighten up quickly.

There is a possibility that it might take a long time to relax the muscle, but once it does, you may be able to stretch it as wide as you can without any trouble. You can think of happy moments or some fabulous vacations which will give a boost in relaxing your sphincter. 

The beginning part

If you talk to some people who have already done anal sex before, they will tell you that the beginning point is the phase where you will experience some pain. This is true as the penis' tip has a wide girth which is something you need to get over with before you start experiencing some pleasure.

This is the point where communication and lubrication come into play. It's quite a weird combination but is undoubtedly a key to successful anal penetration. If you have the right lube and the right partner by your side, then there cannot be anything outstanding than this.  

Anal Sex Prep - To Prevent Embarrassing Accidents

No rush movements

You might have to control yourself before you feel the urge to rush in.

Sure, it is the heat of the moment which makes you go wild on each other, but this is something which can work for the vagina but can be dangerous for the anus. You cannot do any harm if you go slow and steady.Keep your movements constant and gradually increase your pace by aligning with your partner.

A pleasuring stimulation 

There is a question that people often wonder about - Do women orgasm in anal sex? Well, some answer yes to this question while others think "how come?" The best answer is orgasm can happen in anal sex if you do not try to take shortcuts and allow things to unfold.

The best way to get your partner an orgasm is by stimulating her other body parts, especially the vagina or clit.

If you think this is a lot of multitasking, considering the option of fingers and at the same time controlling your pace in the anal penetration, then we advise you to use a vibrator, which functions explicitly through a remote.  

The 5 Best Anal Sex Positions

Being completely honest, the positions for anal and vaginal sex are often the. The ideology of sex positions is to give people the best pleasure, and we will be listing out the top 5 positions to try anal sex in.


If you emphasize over reading the terrain, then the missionary position would be an optimal position to have soothing anal sex.

Reading the terrain here means to carefully observe the partner's reactions and adjust your actions accordingly.

To try this, elevate the receiver's hips by means of a small pillow which will help you get a better angle.

If you consider raising the legs or sometimes placing it on your shoulder, it would be of immense help in smooth movements.

The best thing about missionary position is that both you and your partner can see each other and gauge each other's movements, responses as well as the feelings.

Considering the sensitivity of anal sex, this position makes more sense to have a relatively better view of each other.

anal sex missionary


Ah! This dominating female position is loved by many females because it lets them take charge of the situation.

You need to place your legs on both sides of your partner on the mattress and then place your hands on his chest to maintain balance.

This position gives girls the freedom to go front and back or up and down or sometimes even sideways swirling round and round.

You can decide your own pace and of course the depth as well. This is the best way to stimulate your partner.

anal sex cowgirl

Doggy Style

Doggy Style is a famous and basic position to perform anal sex.

It is the first and sometimes the starting position among many couples out there. 

This position gives control to the partner who penetrates. It becomes important to relax if you are at the receiving end.

You can always start slowly to see if everything goes right and then increase the speed once you become comfortable.

To create more stimulation, the male partner can press his partner's boobs or reach out to her vaginal area.  

anal sex doggy 2

Reverse Cowgirl

The cowgirl position involves taking a better view of your partner.

Reverse cowgirl position is the same as the cowgirl position with just a minor difference that the receiver here flips 180 degrees and her back faces the giver.  

As we say that men are visual lovers, and when men see their partners from back getting on top of them, they might go wild.

The best part of such a position is that the girls enjoy their control at the top while you have some fun and move your butt as per your pleasure.

You have the option of switching up your pace as well. 

anal sex cowgirl


If you are feeling a bit lazy and want to introduce some cuddling into your anal sex, then this position could be a great way to kick things out.

To be in this position, your partner gets inside you from behind, and you need to place your leg against his to create more room.

While you are diving into the position, you can use a vibrator for some vaginal fun.

However, if things get complicated, then adjust your position as per your partner and get ahead with a plank position where you lay flat on the bed and have your partner on top of yourself.

anal sex spooning

After the Action

Now that you are done with your anal sex, what will you do next? Well, if you had a great anal sex, wipe off the bodily fluids and get ahead by throwing out the condom, and then you can go right back to bed and cuddle with your partner.

Cuddling is a great activity after sex which strengthens your relationship with each other.

You should give yourself a gentle wash with some lukewarm water which would surely be loved by your butthole because warm water tends to bring a lot of relaxation. Always ensure to use gentle products and avoid using harsh ingredients at your sensitive place.

If you are the giver and wearing a condom (as you should be wearing it during sex), then you should give your penis a nice wash.

Some Additional Safety Tips and Important Points to Remember   

Let us take a closer look at some of the safety tips and important points to remember while you have a tremendous anal sex experience.

  • Smoothness will help you a lot - You need a cleanliness check before you dive into the action. Make sure you cut your nails, and your sex toys are smooth. There are some golden rules where you need to take some preventive steps while putting anything inside of the anus. If we simply put it togetherthe smoother will be your area, the lesser pain you'd experience.
  • Cleanliness prevents infection - There is a need for practising sanitation before, during as well as after the sex. It should be observed every single time because you might lose your inhibitions out in the heat of the moment and start playing risky, which you might have to pay for it afterwards. Therefore, cleanliness can save you as well as your partner.
  • Lubrication is necessary - We have emphasized a lot about using lubricants as it will help you in easy penetration. Lubrication is essential even if you insert your fingers, use some sex toys or start out with the actual penis.
  • Sex toys should be handled with care - Your toys must have some base if you are inserting it in your anus otherwise you might end up landing in an emergency room of a hospital. There are some do's and don'ts which are followed while purchasing an anal toy/butt plug (which we have discussed in the earlier section).
  • No transfer at all - You should not transfer from your butt to your vagina in one sitting. This is again a concern of bacterial infection, and you may want to consider some cleaning before you shift your focus to the other hole. And, a condom is a must.    

How to Have Anal Sex Safely

With a lot being already said, we wish you a lifetime of happiness and a perfect humping!

If you need any suggestions regarding sex toys or lubricants, then go ahead and send your queries to us. We will surely be assisting you. We hope you have a good time and we will see you next time.

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