How to Bottom Without Pain: Anal Sex in 8 Simple Steps

How to Bottom Without Pain: Anal Sex in 8 Simple Steps

 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!

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How to Bottom Without Pain

How to bottom without pain

How to Bottom in 8 Easy Steps

To Start: Bottoming Should Not Hurt

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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.

Preparation: Use An Anal Enema

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Before you start, make sure that you clean before having anal sex.
Douching is by far the easiest way to get the job done. It will make sex more comfortable and remove any worries you might have.

Enemas work by injecting water and flushing our any surprises you might haver lingering behind. You can check our more in-depth guide to using an Enema here.

Loosen Up: Practice on Your Own

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Before actually having sex you should first practice on your own and get used to the sensation. Your anal sphincter is a muscle like any other, and can be trained and stretched to prevent injury.

Anal trainer kits, anal plugs, or even a finger are a great way to train your anal muscles at your own pace and get used to the felling of bottoming before the real thing.

Learn To Relax Your Anal Sphincter Muscle

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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.

If you have ever gone number 2 then you already know how to relax this muscle. The key is to be able to do this same action but on command.

While pushing outward with you lower abdomen like you are going to the bathroom. Feel your anus relax and slowly insert a lubricated toy finger.  You should notice your inner muscles start to relax and open.

Get Used to the New Sensation

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

It is just your body’s natural reaction to an unfamiliar situation. We are training your body to learn the difference between sex and nature’s calling. With a few practice runs, this feeling should go away. Eventually, this should start to feel pleasurable.

Practice Inserting and Pushing Out

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As your body gets used to the feeling of having a finger or toy fully inside, it is time to move onto motion. We want to simulate the thrusting motion of sex.

With the toy fully inserted, push out and allow it to exit your body, but not fully. Slowly, try again to insert it, and repeat. Practice this motion faster and faster until you are at the full speed of sex.

Move Up in Thickness

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While learning how to bottom without pain, thickness more than anything is what will be your biggest hurdle. To avoid pain, you should continue to work up to more realistic sizes.

You can do this by using more fingers, larger plugs, or even a realistic dildo. Once you are comfortable with a more realistic size then we are ready for the real thing!

Anal Sex: It’s Time for the Real Thing!

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Once you are comfortable with the feeling, and have enough practice sessions, then it is time for the real thing!

Adopting the same principles, you should be ready for bottoming in real life. Remember to lube up, push out, relax, and start slowly.

Things to Keep in Mind

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A big part of anal sex is in comfort and trust. Put simply, if you are comfortable, relaxed, and communicate well, then learning how to bottom becomes much easier.

Remember to go slowly, communicate with your partner, and practice, practice practice!

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A Bottom Boy’s Essential Supply List

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Having the right supplies can help make preparing for, and having anal sex a heck of a lot easier. For everything from practice, prep, to the real thing, these are the supplies you should have to make anal sex more comfortable.


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Clean Up With an Anal Enema

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Shower Head Enemas let you spray water directly inside!

Enemas work by shooting water deep inside and removing any surprises you might still have after using the bathroom.

For most people, the pros is a great starter Enema.  It is made from medical-grade silicone and is simple and safe to use.  The majority of people choose the medium size.

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View Pros Enema on: MQ Store

$19.99 $14.99Add to cart

Use a Quality Anal Lube

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

Having a proper anal lube is the most important factor of how to bottom without pain. If you want to have comfortable and enjoyable anal sex, then you NEED to use anal lube. No questions.

Check Out Our Full Guide: Choosing the Best Anal Lube

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

Pjur Analyse Me! as the name suggests, it was designed specifically for anal play and includes an anal relaxant and mild numbing agent.

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

View on: MQ Store

$49.99 $36.71Add to cart


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Apply Plenty of Lube Deep Inside

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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View on: MQ Store

$17.99 $12.71Add to cart



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


Practice with an Anal Trainer Kit

Colt Anal Plug Dilator Starter Kit

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.

(BULK) COLT ANAL TRAINER KIT details

View on: MQ Store

$49.99 $43.87Add to cart

Use An Anal Dildo For a More Realistic Size

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Anal 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.

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View Boy With Balls Anal Dildo on: MQ Store

$45.99 $37.83Add to cart


Anal Sex Starter Kit Delux

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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:

Anal Sex Stater Kit Delux

View on: MQ Store

$199.99 $167.83Add to cart

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.

Read More:


Best Anal Lubes for Sex

Best Butt Plugs Anal Toys

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Best cock rings penis

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If you have any questions about how to bottom without pain or would rather ask us directly feel free to email us at [email protected], follow us on YouTube and Facebook. and write your thoughts down in the comments below!

Do you have any tips or suggestions for how to bottom without pain? We would love to hear. Share them with us and other readers in the comments below.

Mr. Q

I'm Mr. Q. I started MaleQ with the goal of answering the questions about sex, dating and relationships for people just getting stated. If you have a question, suggestion, or are just looking to chat, feel free to message us at: [email protected], check out our YouTube page or Facebook.

This Post Has 28 Comments

  1. Avatar
    stephenrichards

    How do I overcome my fears about what my boyfriend might do to my backside?

    1. Avatar
      Matthew Brown

      The most important piece of advice I can give to anyone with concerns about bottoming is to be relaxed. If you are not comfortable with your partner or you are nervous then it will be a very painful experience. If you mind is not relaxed, then your body will not be either. A great way to overcome your nerves is to set the mood. You can do this with music, foreplay, or one of my favorite things, giving a massage. YOu can check out one of my past articles here.

    2. Avatar
      James

      Me and my partner are going to bareback for the first time, is there a lube that will let me feel the moment he cums inside me.

  2. Avatar
    Donald Wallace

    I was a homophobe and I suppose bringing myself to these articles after some bi curious thoughts has helped me overcome this feeling of shame I’ve been caring and pushing away for so long.

    1. Loren Couse
      Loren Couse

      Hey Donald,

      Thanks for giving the site a look. I am glad it has been helpful to you. If you ever have any questions or just want to talk feel free to send me a message at [email protected] .

      All the best,

      Loren

  3. Avatar
    Dany

    My girl want anal sex. But i haven’t done it before. Can anybody help me in this part. How will i do this with her? I am not a virgin but i never go back before. How will i do? Will it easy to put my cock inside to her butt

    1. Avatar
      eric

      @danny it will go in easy if shes already had anal sex before. Try to slide it in but make sure its lubricated down there. Thats it lol.

  4. Avatar
    Krys

    I am a bottom. I have been in a relationship for 8 years we broke up. Well after maybe three years of not even looking for someone I met a really good man and I want to bottom for him but I am worried I haven’t have sex in three years should I treat my self like a first timer

    1. Loren Couse
      Loren Couse

      Hey Krys,

      Thanks for reading the site. I think it is a good idea to treat yourself like a first timer again. If it has been a few years like you said then it is better to be on the careful side of things. You probably already have a good idea of what to expect, but take it super slow the first few times and ease yourself back into the swing of things.

      Best of luck!

      Loren

      1. Avatar
        Krys

        I have been using an eight inch dildo with plenty of lube I have a hard time at first put it works out In any way I thought it would get easy but I feel like I am going have to use the dildo before I have sex

  5. Avatar
    Jack

    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?

    1. Loren Couse
      Loren Couse

      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!

      Loren

  6. Avatar
    Nate

    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?

  7. Avatar
    John

    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?

    1. Loren Couse
      Loren Couse

      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 [email protected] .

      Cheers!

      Loren

  8. Avatar
    Phillip

    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

  9. Avatar
    Bi-Louis

    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.

  10. Avatar
    Top2bottom

    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??

    1. Loren Couse
      Loren Couse

      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: [email protected].

      Best!

      Loren

  11. Avatar
    Carleton Morris

    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!

    1. Loren Couse
      Loren Couse

      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.

      Best,
      Loren

  12. Avatar
    Rene Tremblay

    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?

  13. Avatar
    Anonymous

    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

  14. Avatar
    Harry

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

  15. Avatar
    Sean

    Hi I experience small amounts of blood after using toys I live up very well and the blood goes away after
    I feel no pain and can’t understand why it happens?

  16. Avatar
    Tina Klaeger

    Small amounts of blood are normal. I an a 19-year-old woman, petite at 5’1”, and I have anal sex four or five times a week with my boyfriend, who is 6’4” and has an 11-inch cock. What is important is to use shea butter as an anal lube because it facilitates anal penetration and controls friction in order to limit any bleeding to a small amount. With shea butter, my boyfriend lubricates my anus, rectum, and sigmoid colon. The lube allows him to insert the full length of his 11-inch shaft inside of my asshole. It also allows him to thrust as hard, as deep, as fast, and as long as he wants while having anal sex with me, and I only experience small amounts of blood, which is normal and perfectly safe. In a one-hour anal sex session, he thrusts me anally about 3,600 times. Multiply that by five sessions, and I figure I receive 18,000 anal thrusts up my asshole every week, and I am a petite 98-pound woman. That is 936,000 anal thrusts per year. That means that over the past two-and-a-half years, I have received more than 2 million anal thrusts from my boyfriend. And I am a healthy 19-year-old woman. So, I don’t worry about small amounts of blood, and neither should you as it is perfectly normal.

  17. Avatar
    Pat

    Hi,
    I’m a bottom and I have had lots of lovers. I am a size Queen so big penises don’t scare me. But I’ve recently met a man who wants to have sex with me. He has an 11 inch penis. Girl isn’t any problem, but I’ve never had 11 inches. The biggest ever before is 9 inches and that one hurt at the bottom. I only had the 9 inches one time. The biggest before then was 8 and that seemed perfect. Is there anything I can do to get ready for 11 inches? I want it all. He says he’ll be patient. But they all say that until the heart of the moment.

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