How to Have Anal Sex For the First Time

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Sex is complicated.  Anal sex is even more so – it can be dirty, painful, and scary especially if you have never tried it before.  Having anal sex for the first time isn’t easy, I know, but if done right, it is great!

I have written a lot of articles over the last couple of months about getting ready before sex, picking the right condoms, and what to do after.  These have all been popular with readers and I have gotten some great feedback (thank you, everyone).

This is the next step.  A comprehensive, one-stop resource for anyone who is starting out and give you a better idea of how to have anal sex for the first time.  I am constantly working to improve the site, and will be updating this article as I go to make it better.  If you have feedback or tips then join the discussion below!

Quick-Jump

 


Supplies:
 Lube
 Condoms
Preparation:
 Cleanup
 Douching
Practicing on Your Own:
 Sex Toys
Having Sex: The Real Thing
 Foreplay
 Rimming
 Go Slowly
 Communicate
After Sex
 Know When to Stop
 Blood After Sex
 Fissures and Hemorrhoids

 

How to Have Anal Sex for the First Time

 

Before we talk about sex, let’s start with your body.  If you are going to have good sex then you  first and foremost need to be in touch with both your mind and body.  Keeping both in sync and listening to them is the first step to having great sex.

Mental

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More than you may realize, sex is all about your state of mind.  Your brain is a powerful tool – It controls everything from your thoughts, feelings, movements and emotions.

The biggest fear for anyone who has never had anal sex is definitely the pain.  This doesn’t help when your absolute worst enemy when bottoming is to be nervous.  If you are not comfortable and mentally ready, it will cause your body to tense up – and that is a bad thing.

Put simply, if you are not in the right state of mind, then your body won’t be either.

Sex is never something that you should rush into or do on a whim.  You need to be comfortable and ready.

Only have sex because you want to.

Physical

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The simple most important piece of advice I can give to anyone starting out is to listen to what your body is telling you. Follow’s its cues and pay attention to what it is trying to tell you.

Bottoming should not hurt.  

In fact, it should be some of the best sex that you have ever had. Pain Is your body’s way of telling you that something is wrong. It can mean many things and the most important skill is learning how to read those signs.

Slow down, use more lube, relax.  It may be even saying “I’m not ready yet.”

If it hurts it is ok to say “no”.  Don’t have sex unless it feels good, and unless you are ready both mentally and physically.

 

Supplies

Anal-Sex-Starter-Kit-square

Before we dive into what to do before and during your first time on the playing field, you need the right equipment.

Unlike other types of sex, with anal, you have to buy your own lube.  Anal sex as you probably already know does not have natural lubrication.  That means you are going to need to get greased up beforehand and bring your own lube to the party.

 

Anal Lube

If you don’t have some kind of lube then having anal sex will be nearly impossible.  I know some people who have tried, but it is stupid, painful and just plain dangerous.

Yes, things like hand lotion work, but they are not designed for sex, and are not condom safe.

You can do a lot better, and you should.

If you want to be as safe and comfortable as possible you should get a lubricant designed for sex.

Even better, there are many lubricants on the market made specifically for anal sex and do the job better than almost anything out there. I have used Pjur Analyse Me! for years because it is super slippery, long-lasting, and has an anal relaxant to help loosen you up and prevent pain.

the-best-anal-lube-analyse-me

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Read More:

Best Lube for Anal Sex   Choosing the Best Anal Lube

 

Everyone has their different preferences, and I recommend choosing the lube that best suits you.

Lube Injectors

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Lube injectors are also an excellent tool to help make sex easier.   Lube injectors are a great way to get lots of lube inside without making a mess.  They work like a syringe and literally shoot lube deep inside.  They cost about $10 but are easier than trying to shove gobs in with a finger.

Condoms

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I believe in every person’s right to free choice.  But, the choices we make have real risks and trade-offs.  That is especially true when choosing to wear a condom.

If you are going to have anal sex then I cannot stress how much greater your risk is for contracting an STD, especially HIV.   Having anal sex makes you are around 10 times more likely to transmit an STD compared to any other type of sex. The risk is real.  That is why it is so important to use a condom.

Picking the Right Condom for Anal Sex

The Best Anal Condoms

 

Luckily, wearing a condom doesn’t have to suck.  Today, condoms are thinner and stronger than ever before.  By having safer-sex you now make little compromise in terms of safety vs. comfort.

Additionally, most medical centers and clinics give out free condoms. Health services and safe-sex programs have gotten so wide-spread that if you know where to look, you could easily never pay for condoms.

If though, you feel like buying your own, then there are a great selection of condoms ideal for anal sex.  My top pick is Durex’s Extra Strength, Extra Lubricated condoms because you will NEVER worry about these breaking.

If safety is your number one priority, then theses are the way to go.  They are also super slippery which is a must if you want the sex to actually feel good.

View Full List:

   Best Condoms for Anal Sex

 

 

Preparation

Cleaning Up

Anal Sex For the First Time Shower

One of my biggest fears before having sex the first time was getting over my poop phobia.  This freaked me out and clawed in the back of my head for such a long time.  No one wants to lose their virginity only to be greeted by a poop dick.

I look back now and realize how silly I was.  Push your fears aside, because with the right steps, the whole “poop” thing is not a part of anal sex.

The easiest way to clean out your pipes is to limit what you eat 24 hours before having sex.

Then, simply use the bathroom normally, but take your time.  I give myself a good 20 minutes to let my body naturally flush everything out.

After, take a shower and clean your asshole. Yes, clean it!
Make sure to go about an inch inside with a little bit of soap and warm water.  Don’t use a too much soap or else your skin will get raw and make sex painful.

Lastly, make sure to wait about an hour before sex and you should be completely clean!

 

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Douching

Planning ahead is a lot of work I know, and sometimes sex is spontaneous.

The alternative if you are crunched for time or want to be extra thorough is douching using an enema.  Douching is simply using water to flush your bowels out completely.

The water helps to loosen up anything that might be lingering behind, and it makes everything empty out – fast.

Plus, douching with an enema will make sex more comfortable as a bottom and help set aside that first-timer anxiety.

I didn’t start to douche until about a year after I started having sex, but boy does it make a difference.  I have been using this Anal Douche for some time because it is comfortable, simple, and cheap.

cloud-9-fresh-deluxe-anal-enema-2

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Douching may sound a little strange when reading it for the first time, but using an enema is much more common than you might think.  Most people I know do douche, even if they are shy to talk about it. Just think –  porn stars don’t get that squeaky clean without a little help.

Read More:

Best Anal Enema
Enemas and Douching Before Anal Sex

 

Having Sex: The Real Thing

Foreplay

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As I mentioned in the beginning, being relaxed and in the right state-of-mind can make all the difference when having good sex.  Foreplay is a great way to set the mood, and make your body ready for the real thing.

Atmosphere is key.  Everyone has different preferences but be creative.  Try playing music to set the mood.   Light some candles or adjust the lighting.  Little things can help add to the experience and make you more relaxed.

Massages are also a wonderful tool to help you relax.   Go slow, get intimate, and give a massage that you would want to get.  Don’t forget to communicate with each other.   

Read More:

Rimming - How to Rim and Get Rimmed
Rimming – How to Rim and Get Rimmed

 

Rimming

Yes, that’s right, rimming, licking butt, eating ass, whatever you want to call it.  Think of it like a massage with your tongue – and man does it feel great.

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Now, I know what you are thinking, and I have one word for you – hygiene.  If you wash properly with soap and water before and make sure you clean about an inch inside, I promise you, you will be cleaner than a whistle.

I always say, never do something you don’t feel comfortable with.  But though, if you are feeling adventurous rimming is an exciting way to take foreplay to the next level.

Communication, Communication, Communication!

Sex is a two person game.  That means communication in both directions.  I know that this is a skill not everyone is great at, but it is essential if you are going to have great sex.  Talk to each other, and read each other’s body language.

Communication starts even before entering the bedroom.

If you are especially nervous, express your concerns before actually having sex.  Tell him your thoughts, worries, and expectations.  He is probably just as nervous as you are.  Making sure you are on the same page, and giving each other tips and expectations will make the whole experience go a lot smoother.

 

How to Have Anal Sex For the First Time-8

 

Talking during sex is just as important. If he is moving too fast, then say so.  If you need more lube, tell him.  If you ever need something then the best thing to do is to simply speak up.

On the other hand, be sure to ask him questions, and talk about how he is feeling.  Make sure that you are both in sync throughout the process.

 

Go Slowly

Tops, are not always the most considerate towards bottoms – usually because they are not the ones who are in pain.  I get it, they are horny, and they are about to get laid.  But god damn it slow down!

This is something you need to make clear the first time you have sex as a bottom.  Tell him he needs to go slowly and move when you  are comfortable.

Also, make sure to use plenty of lube inside and out.  Also, give him lots of lube for good measure too.

Now, have him enter slowly, starting with just the tip.  Remember, this is your first time.  Your body isn’t quite sure what’s happening and you need to give yourself time to get used to this new feeling.

Read More:

   Bottoming for the First Time

 

Once you are comfortable, let him move in small increments.  When I say small I am talking millimeters a time.

Next, wait a few seconds and have him pull out a little.  Then have him move back in, this time, a tiny bit more.  Wait, and pull out.

 

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Repeat this and listen to your body.  Give it time to relax, and it will.  Sometimes it takes 1 minute to get used to the feeling and sometimes it takes 10, but be patient. 

Eventually, you will be surprised how relaxed your anal muscles will be. Just remember, it should not hurt.

When he is fully in, it’s OK to have him wait inside while you adjust.  This might sound strange but I am totally serious.

Sex is NOT like porn and you won’t be pumping it out right after you start – especially on your first time.  You need time to work up to that point.

Move up slowly and soon enough you’ll be going at it.

 

 

Know When to Stop

 

You have come this far but always remember – It is OK to stop!

Anal sex is tricky business.  Not everyone gets it on their first try, and it is not worth having a painful, miserable first experience.

Your priority should be protecting yourself and making sure you don’t get hurt.

Also, don’t worry about disappointing the other person.  If he truly cares about you then he will understand.  If not, then he is probably not the best one to be spending your first time on.  And remember, you can always try again!

 

Blood After Sex

No matter how much you prepare, there is always a risk of getting fissures, or small tears from anal sex.  Fissures and hemorrhoids are not fun, and seeing blood after sex can be a very scary experience.  The best thing to do is treat your fissures quickly and follow a few simple steps to prevent them in the future.

How to Have Anal Sex For the First Time-2

 

 

The first thing to do is keep those fissures clean. This is the most important tip of all to make sure they heal quickly!

Right after sex, take a shower and push outward slightly to expose the cuts.  Rinse well with warm water.  It will hurt but you need to do this as soon as possible. Also, make sure to do this every time you go to the bathroom in the following days.  If you stay on top of it and keep the area clean then your fissures should clear up within a few days.

If they are especially painful, try using a little lube overtime before going to the bathroom.  It will sting, but it will help move things along.

 

Avoid Fissures and Hemorrhoids

Avoiding fissures and hemorrhoids is just as important and much better than getting them in the first place.  Simple things like drinking lots of water every day and staying properly hydrated can help keep your body lubricated which will, in turn, make your stool softer when going to the bathroom.

Also, eating a high fiber diet with fruits and vegetables will keep your digestive system in tip-top shape.  Try avoiding dairy as well as high acid foods, and especially spicy foods.

Lastly, you should try to poop at least once a day, every day, if not more.  Make it a habit.  This will really help, I promise.   Using the bathroom regularly helps to make sure your stool stays soft and easy to pass.

Read More:

Anal Sex For the First Time   Blood After Anal Sex – Hemorrhoids and Fissures 

 

Avoiding Pain in the Future

For some people no matter what they do, bottoming still hurts.  The best thing to do is to continue practicing on your own and learning to relax your sphincter muscles.  Remember to breathe deeply and not to tense up.

If you are still having problems then anal relaxants are a great way to get that extra help to loosen up a bit and make anal sex pain free.  Anal Eze is one of the more famous products and is applied in the form of a gel.  You can use this along with any standard lubrication to help get the relaxing effects.

Some products like Pjur Backdoor have a relaxant built in as well as a numbing agent to help with mild pain.  There are some drawbacks to this kind of product though because the numbing agent can make who ever’s topping less sensitive too which may get in the way of the fun.

Read More:

MaleQ&A-Very-painful-fissures-and-afraid-to-have-sex-again
 Taking the Pain Out of Anal Sex

 

Also, you have to be careful that you aren’t doing yourself more damage than you realize because you are less likely to notice the pain (remember that is your body’s way of telling you something is wrong).

But if used responsibly, then anal relaxants are a great way to ease your way into anal and combat some of the discomfort.

 

Practicing Anal on Your Own

You can’t ride a bicycle without first learning with training wheels. That is unless you want to fall on the pavement and skid your knees.

How to Have Anal Sex For the First Time-13

Sex is no different.  If you jump in without practicing on your own, then your first time will hurt.

Practicing can be a range of things from fingering yourself to using a sex toy.  The important thing though is  to do something to prepare yourself.  The more you practice beforehand, the easier the real thing will be.

 

Sex Toys

Butt-Plugs

Sex toys like dildos and butt plugs are one of the best ways for you to get ready for sex on your own.

There are a large variety of anal dildos and butt plugs which are designed for anal sex.  These offer a more realistic size and shape to give you a better idea of what to expect.

More importantly, they let you move at your own pace because you are in control.  Think of a dildo as a stepping stone where you don’t have to worry about making mistakes or juggling that extra anxiety of having someone else there.

Like stretching out before going to the gym, using a toy on your own will help you to loosen up and make you better prepared and more comfortable when you have anal sex.

 

Read Full Guide:

The Best Anal Dildo American Whopper   Choosing the Best Anal Dildo

 

If you are especially tight (which most anal virgins are) then an anal trainer kit is a great tool to help you loosen up.  These are essentially graduated butt plugs which come in sets of different sizes.  These let you stretch out over multiple sessions and move up gradually.

Joel Kaplan Anal Dilator Kit

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It may be uncomfortable the first few times, but the more you try, the more your body will become accustomed to the feeling.

For men, you can also look into using a prostate stimulator.  These are specifically designed to hit the P-Spot (male G-spot) and re a great way to practice anal on your own.  Using one will increase sensation and can give you one of the biggest orgasms of your life.

Read More:

The-Best-Prostate-Stimulators-and-MassagersThe Best Prostate Simulators

 

 

Keep at It

Like anything in life, the more you do it, the better you will get – sex is no different. Everyone is going to be a little nervous and inexperienced their first time.  And that’s OK!  The important thing is to make your best effort and keep trying.

If you are still nervous then practice more on your own and move at a pace that is comfortable for you.

If you have any tips about how to have anal sex for the first time or would like to share your own stories then please leave them in the comments below!

2 Comments

  1. Patrick
    February 01, 2015 12:36 am Reply

    Great article. I used similar steps and patience with a friend two weeks ago. We’ve been seeing each other for three years off and on but had never gone “all the way”. He enjoyed it and now wants more

  2. steve flynn
    May 20, 2016 5:41 pm Reply

    very helpful thank you

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