How to Bottom Without Pain: Anal Sex for Beginners

    Categories: Anal SexHow toSexSex Toys

I am here to help make sure you are READY for anal sex and walk you through how to bottom without pain for the first time.

Having sex can be a scary, nerve-racking experience.  I can remember bottoming for the first time – I had absolutely no idea where to start.

As a result, it was painful, embarrassing and not very fun.  But that was because I wasn’t prepared.

Below we have put together a comprehensive guide to make sure that your first time bottoming is the best that it can be!

Check Out Our New, In-Depth Anal Sex Guide!

How to Bottom Without Pain

Bottoming Should Not Hurt

Bottoming is a strange and unfamiliar experience, especially if you are a first timer.  Remember, bottoming should not hurt.

In fact, it should feel great!

This is probably the biggest misconception surrounding how to bottom.

Pain is your body telling you that you are doing something wrong!

This is why understanding your body is the best way to prepare yourself.

Get Clean

This seems like a no-brainer but you must make sure that you clean out your colon before having sex.

Douching is by far the easiest and most thorough way to get the job done. Cleaning up beforehand will make sex more comfortable and remove any worries you might have.

The last thing you want is looming thought of a messy first time.

You can read a more in-depth guide about douching here.

Practice and Loosen Up

Before actually having sex you should first practice on your own a bit so you can get used to the sensation.

Find a private, comfortable place where you can relax.  Make sure your hands are clean and your fingernails are cut.

Remember, you want to be as comfortable and clean as possible.  Taking a nice, warm bath is also a great idea as it will help you relax which is what you are going for.


There are two major muscles at the entrance of the anal cavity.

The outer sphincter muscle, which for most people is relatively easy to control.

The inner sphincter is located about in inch inside that typically causes pain while bottoming. Learning to control this muscle is the key to making sex more enjoyable.

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Choosing the Best Lube for Anal Sex

The Best Anal Dildo for Beginners

If you have ever pooped before (which I know everyone reading this has) then you already know how to relax this muscle.

Most people are unaware that they are even doing it.  The key is to be able to do this same action but on command.

While pushing outward like you are going to the bathroom, slowly insert a lubricated finger.  You should notice your inner muscles start to relax and open.

Once you are in, you may have a strange feeling like you need to pee.  This is normal.

It is just your body’s natural reaction to an unfamiliar situation. With a few practice runs, this feeling should go away.

Once you are comfortable with one finger, try adding another finger and continue to work your way up.  Eventually, you will be able to move up to a comfortable size for sex.

Take It Slowly

If you are bottoming for the first time you need to take things slowly.  For most people having a finger, or anything up in there is a very strange and uncomfortable sensation.

Make sure you start out slowly and each time you will notice it gets a little easier.  Again, make sure that your finger still has plenty of lube and follow the steps above.

Once you become comfortable with this process then you should be more comfortable with real sex.

Get the Right Supplies

Anal Lube

You wouldn’t believe how many guys think you don’t need lube when having anal sex!

This is wrong and just plain stupid!

Having the right supplies is the most important factor of how to bottom without pain for the first time, and if you want to have comfortable and enjoyable anal sex, then you NEED to use lube. No questions.

Check Out Our Full Guide: Choosing the Best Anal Lube

Picking the right anal lube is probably the single most important aspect to having an enjoyable experience when learning how to bottom.

Luckily, there are some great lubes designed specifically for anal sex.  So do yourself a favor and invest in some good quality lube.

“Having the right lube will help to make entry smoother and greatly reduce pain.”

One of my personal favorites is Pjur Analyse Me!. As the name suggests, it was designed specifically for anal play and includes an anal relaxant and mild numbing agent.

This makes learning how to bottom much easier. It also has a great consistency and is extra slippery.

I have been using this lube for years and it is an ideal choice, especially if you are just starting out or have had problems with pain in the past.  If you haven’t already, be sure to check out my in-depth review.

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$39.99 $34.21

Read the full article on picking the Best Anal Lube here.

Use a Lube Injector

Lube injectors are another thing to consider as they are a really great way to get lubed up quickly and easily. They act like a syringe and allow you to apply lube consistently deep inside.

It took me a long time before I started to use one, but it really makes anal sex easier and more comfortable.

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Extra Training

To get a more realistic size for sex, you may also want to invest in a butt plug or a dildo.  Butt plugs often come in trainer sets that allow you to start at a comfortable size, then slowly work your way up.

Anal Trainer Kits are probably the quickest way to loosen up and give you a gradual ease into a larger size.

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$52.99 $46.87

Dildos are also great because they help you loosen up down there and give a much more realistic experience of what sex will actually feel like.  Just remember to use a condom over your toy and wash them well after use.

The Anal Sex Starter Kit

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$112.57 – $147.87

For those looking for everything you need in order to learn how to bottom, I recommend taking a look at the Anal Sex Starter Kit.

It has everything you need to practice on your own and get ready for the real thing including:

  • An Anal Trainer Kit
  • Enema
  • Toy Cleaner
  • Two Lube Injectors
  • Pour Analyse Me Comfort Anal Lube

Packaged together you will actually save you about $40 compared to buying each separately.

If you follow these steps and practice often, then you will be on your way towards amazing anal sex. Everyone will feel some discomfort starting out, but the payoff is well worth the time and effort.

Just keep at it and soon you will be ready for the real thing.

For a more in-depth step-by-step guide, check out my new, comprehensive guide to having anal sex for the first time.

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If you have any questions or would rather ask us directly feel free to email us at info@maleq.org or write them down in the comments below!

Do you have any tips or suggestions for how to bottom without pain? Let us know in the comments below.

This post was last modified on September 20, 2018, 12:13 pm

Loren Couse :I started MQ with the goal of answering all the questions I had about gay sex, dating and relationships when I was just starting out. If you have a question, suggestion, or are just looking to chat, feel free to message me at: info@maleq.org, check out our YouTube page, Facebook or Google+.

View Comments (25)

  • I have never tried anal and I want to. I've started with plug then moved into dildo (7 inches). I"ve been practicing and it doesnt hurt anymore. Do you think it will hurt the first time I have sex with a real person even if I've been practicing?

    • Hey Jack,

      As long as you take it slow and you use enough lube, I think it sounds loke you should be just fine! Practice makes perfect.

      Best of luck!


  • Hello everyone, I'm going to a trip with my bf and this is the first time we will have anal. I've had anal twice but let's say I want to play 3 days in a row, How do you stay clean during the whole weekend? Is it safe to douche before having sex back to back to back as douche Friday, Saturday, and Sunday before sex?

  • Hi there, I am a top that didn't have much sex but I know how ot feels. I recently met a guy and we both really wanna have sex, but it is his first time, so he never was bottom before. I'm super scared I won't make it a good experience (I'm well endowed too so i'm scared to hurt him). Any tip for it to be nice for both of us?

    • Hey John,

      I am still getting around to writing an article about "How to Be a Good Top", but I think a lot of the advice I would have is still pretty similar.

      To start, go slowly (like really slow, bit by bit), use lots and lots of lube, and communicate with each other. Remember, it might be a bit uncomfortable for him his first time, but it should not hurt. Try some foreplay to get started (rimming, fingering, massaging). Relax, and make sure he is too.

      As a top your biggest priority is to make sure your partner is comfortable, and do only what he is comfortable with doing. And remember, even if things don't work the first time, you can always keep practicing and move up to the real thing.

      I know this is a bit short, but if you want to chat a bit more in-depth, feel free to send me an email at themaleq@gmail.com .



  • I am in a long term relationship, and the sex has been rather infrequent of late. I am an early spurter, which is off putting. We actually have not had penetrative sex, but I would love to bottom for my partner, as I know he does not want to bottom. I thought that being a bottom would lessen the probability of spurting too soon., another reason why I would like to bottom. Would you recommend using a butt plug for a few hours prior to bottoming? And putting a condominium on with lots of lube prior to inserting it? I am hoping for a more active and regular sex l

  • I was young and worked in a soap factory during school holidays. One day the supervisor called me in his office and asked me if I would like to experience 'butt pleasure' I said yes because I was so shy to say 'no'. He had a big tool banana shape, I was a bit worried. He prepared my butt for about 30 minutes by inserting his finger and thumb inside my butt using lot of glycerine as lube. Then he positioned me doggy with my legs spread, he applied a warm towel on my butt for few minutes then after lubricating my butt he rub his tool in circular to my anus and slowly pushed his tool inside. Although it was a bit painful when the head got inside but it was also a good sensation, he did it so well that it was more pleasure than pain.

  • You mention putting a condom on a dildo. Is there a reason for it? What about butt plugs, should they be covered with a condom also??

    • Hello,

      You can think of condoms as an extra protective barrier to protect your toy from bacteria. Typically douching before and using a toy cleaner after are enough to protect your toy. Condoms just go that extra step. You can read more info in our full guide on How to Extend the Life of Your Sex Toy here.

      If you have any more questions feel free to e-mail us directly at: info@maleq.org.



  • I have been bi for about 10 years. I am totally straight acting but in bed I prefer and get turned on by playing the submissive role. I have experimented with everything successfully except anal sex. It always hurts and burns but I still crave it want to do it. Nothing turns me on more than the day I am being thrusted like a woman. I always spend a lot of time in foreplay, kissing, making out mutual oral and get rimmed etc but it walyas ends without anal penetration. . I want to do it missionary. Is this the best position? Please help!

    • Hey Carleton,

      The most comfortable position really comes down to what kind of dick and shape you are dealing with! As a bottom, your colon actually curves up and in towards your bellybutton. This means that if you have a guy with a dick that curves upward, then you two should both fit together like a lock and key!

      In this case, missionary position would be your most comfortable position. But you should really go by his shape and choose the path of least resistance.

      But really, after you relax and loosen up, then you can try anything you like!

      Hope this helps.


  • I am married and want to have anal sex with my wife. We both love it. I have been using butt plugs to ease into to the new adventure. I've increased in size to a new 5.5 inch wonderful item. How do I ease this in to our sessions?

  • My Man Wants To Have Anal Sex But I Never Did It Before And His Cock Is 10 inches long and very thick he’s a black man and I know it will
    Hurt besides I don’t wanna have any accident during the sex

  • Hi , I want yo anal for my man , this is embarrassing but I think I have developed heamroids , what must I do