20+ Tips on How to Have Anal Sex Without the Ouch!

Presenting the posterior for penetration is downright terrifying for some people.

It’s right up there with brown recluse spiders, heights, and holes (Trypophobia – yeah, it’s a thing). 

But I’ll let you in on a secret…

Anal sex doesn’t have to be unpleasant, and it doesn’t only exist in the realm of “lights, camera, action!”  

Let’s look at how.


Be really sure you want to try it (or at least, be curious enough about it). Talk to your partner about the prospect.

Whether bluntly or delicately depends on your relationship.

  • It’s completely acceptable to ask
  • It’s completely acceptable to say no

What is NEVER acceptable?

Pressuring someone into it if they aren’t convinced. It’s also not okay to ask them every damn time you’re naked.  Also, the “accidentally-slipping-it-in” move is an asshole thing to do. You can cause serious damage by pulling a stunt like that.


Anal sex has got a bum rap – the big one being that it’s FILTHY.

Considering the nightmare that can come out of there after a night at a Mexican buffet, I can see how people would think that.


The anal cavity is actually isn’t that dirty – there’s very little fecal matter left in there.


When we say “very little”, there’s still a bit in there (especially if you’re near a poop).

This is why it’s always a good idea to wrap up that willy. It makes clean-up that much easier.

There’s also the ever-present chance of STIs.


Once it’s stuck in the rear, it goes nowhere else – not in the vagoo or the mouth.

And forget what you’ve seen on porn!

To prep for a scene, pornstars clean things better than most of us clean… well… anything.

If you want to start dipping your stick into other orifices, switch condoms.

Remember, the vagina’s internal environment exists in a delicate balance. It only takes a little foreign matter to change things from hunky-dory to “JESUS CHRIST WHY WON’T THE BURNING STOP?!”


Up the butt is not fun when you are on the verge of a bowel movement (THAT’S when things could get messy).

Make sure there’s nothing in there, and give things a good soapy wash.

Antibacterial soap isn’t necessary but if you want to get into rim jobs (oral stimulation of the anus), going the extra mile won’t hurt.


This is mostly because of the lube you’ll be using, and that stuff can sometimes be a pain to get out of your blankets.


You can’t just grab anything off the shelf, pay for it with a blush, and then run out of the store.

There is a plethora of brands and styles out there, but you generally want to stick to ANAL lubes.


Because they are (or should be) formulated with a different PH to work with the PH of your anus. Whether it’s water based, silicone or “other” is up to you.

What you should NOT do…

Is keep using anything that STINGS! That is NOT normal and does not work for/with your body.

Oh, and stay the away from KY Jelly – that stuff is about a 4 where the average rectal PH is about a 6.

It also has a 10,300mOsm/kg in osmolality (which is bad). This hyper-osmotic nature of the lube can cause cell dehydration and cell death and make the surrounding tissue more susceptible to infections or diseases.

Everything you’ll ever need to know about sex lubes

The Best Lubes – A Comprehensive Guide on the Slick Stuff


You should be wearing so much of the slick stuff that your backside should look like it’s oozing something out of an Aliens movie.

Also, if you’re having trouble applying it, try a LUBE INJECTOR (they look like a big syringe without the needle). These are good if you have trouble getting lube in with your fingers, toys, or tool. Easy to use and less mess.


Things like warming, cooling, or DESENSITIZING.

They are evil, wretched liquids that should never go near the butt.

Whether we like it or not, pain is our friend. It tells us when shit *giggle* is going wrong.

Don’t dull your never endings with desensitizing lube. It can do more harm than good. Plus, the warming stuff often contains materials from things like chili peppers.



You hear so much of people being turned off from anal sex because of how much it hurts. NEWS FLASH – if it’s being done right, it shouldn’t hurt.

It might feel weird, but not painful.

The first step is lube, the second is talking your way through it, and the third is relaxing. Tensing up will not help things. Keep breathing.


Try a glass of wine. Hell, mediate if it helps.

Also, if you are in charge of penetration, throw in a bit of a massage during things. Anything to help get the blood and arousal pumping.

I promise you, external stimulation goes a long way to making the process easier. 

One possibility is “rimming”. Don’t know what that is? Learn more here. I promise it’s not as bad as it first sounds.


Since you’re going to be all lubed up, using sex toys during your escapades is another great option. They help with arousal and lead to relaxation.

Just be careful of what kind of lubricant you’re using with what material.

EXAMPLE: Silicone toys are great for anal sex (they last a lot longer and are easier to clean). But you can NOT use it with silicone lube because it will degrade the quality of the material and eventually cause tears and other problems.

Also, make sure the toy isn’t porous. If it is, throw a condom over it.

Here are two anal toys worth checking out:

Hush – The World’s First Teledildonic Butt Plug

Edge – An Adjustable Prostate Massager with POWER


Don’t follow what the porn stars do (things like rubbing the tip against the opening for a few seconds then shoving it inside).

They have FAR more experience and their asses have become accustomed to it.

And when I say slowly, we’re talking TURTLE pace.

No. Scratch that.

Turtles will look like Formula One racers compared to how fast you should be moving. This also includes pulling out.


If things still aren’t working for you, or your partner has a dick the size of an elephant’s, consider Anal Trainers.

They look like butt plugs, but come in sets of 3 to five – most starting at the size of your finger and working their way up to something you can be proud of.


And, for the love of god, do not start with missionary.

For beginners, it’s damn near impossible to find things and maneuver your way around to the sweet spot without looking like a fumbling idiot.

  • Cowgirl if the person on top wants to control the speed.
  • Doggy Style is another winner.


Be ready for giggles, laughs, and red cheeks.

It’s not like defusing a bomb, nor should there be the same level of seriousness attached to it.

Also, don’t freak out on your partner if something goes wrong.

When mortification rears its head, the only acceptable thing to say is, “It’s okay, honey. Don’t worry.”


Not only should you be going to the bathroom beforehand, you should also go after.

Especially if you’re loosened up a lot.

The chances of you accidentally losing your bowels are next to none, but a seemingly innocent feeling of “gas” might not be.

Also, if your partner doesn’t wear a condom, and has ejaculated in you, things need to be cleared out.


The anal passage tissue is actually rather delicate – you can get small tears during a hard bowel movement. As long as it’s not a lot, you’ll be fine.

But if you keep seeing blood, talk to your doctor.


You will NOT end up like some over-pulled piece of play-doh.

Things will stretch out during sex, but, after a few minutes, things will go back to normal.

Trust me.

We can have bowel movements the size of an average dick anyways.

And as long as you’re being gentle and using lube, there should be no damage.


Anal sex has nothing to do with sexual orientation. It just means you like it in the ass.

There are TONS of nerve endings for around the anus for both men and women.

Gents also have the equivalent of a g-spot (the prostate). It reacts to stimulation whether you’re gay, straight, bi, undecided, or a damn inflatable doll.


  • Anal queefing is totally possible
  • The first time might just feel weird
  • Beginners might feel a bit sensitive in the anus afterward
  • A bit of smell is possible. Don’t worry
  • You don’t have to douche
  • There is an extremely small chance you might poop during
  • When a woman wears a strap-on on a man, it’s called pegging. 
  • Your butt has a mind of its own. Sometimes things work, sometimes they don’t

AND, after trying it, if you just don’t like it, you don’t ever have to do it again.

. . . . . . . . . . . . . . . . . . . . . 

After all this reading, I’m also sure you’ve figured out one other very important thing … Anal sex is not a spontaneous thing! It takes time and preparation to get to penetration.

So why go through it all?

  • Some men like the difference in the sensation 
  • It’s an erogenous zone capable of delivering immense pleasure
  • If you feel it’s taboo, it can be extra naughty and exciting

I hope this article has helped or enlightened you to pleasure in places where the sun doesn’t shine.

Have an anal-tastic day!

Anything you want to add? Share in the comments!

93 thoughts on “20+ Tips on How to Have Anal Sex Without the Ouch!

  1. As a submissive man I really enjoy the feeling of being pegged by a dominant woman but definitely worked up to it and started on small toys before moving to bigger ones, it’s such a pleasurable feeling though.

  2. Ok so we got the hush and thought it would be a nice fun way to experiment. Theres just one main problem thr rings that are supposeto hold the excess lube feels like a cheese grater both when the toy is inserted and when it is removed. 3 days later my girlfriend is still bleeding. Any ideas?

  3. Omg I used to love my boyfriend doing it to me then it stopped in now I can take it what happened ugh things really change after a baby any special types of lube that work good I want the exciting sex to come back …

    1. I am a 29-year-old woman and my boyfriend puts shea butter on his penis, which allows him to bury all 11 inches when we have anal sex. Our sessions typically last about 90 minutes, during which he will ejaculate 5 or 6 times. It is so intimate and so intense.

  4. I have a dildo and have been practicing. However I can only get it in about 4 or 5 inches and then it starts to hurt as if it’s running into something. I have tried several times with the same result each time. Why does it hurt and wha5 is the pressure I am feeling?

  5. And to relax this part, it needs steps.
    So when a male thinks he can enter like that without time and steps into his female, he s just a stupid moron. And yes, We should do the same thing in his ass. So Mister porno ? You enjoy the feeling ? No ? Your female neither.

  6. Why people do not try first in their own body ? as a male, I wanted to know where is my prostate and how it is ? and except by touching it, there s no other way. So I noticed that your body position was important to help and after a certain time, your sphincter isnt contracted, you have control.

  7. my gf said it would never happen since im 8 and thick, i suggested she take some soma(muscle relaxer and a xanax) then used foreplay, licking fingering etc. communication. lube. slow. slow more communication. lube, slow, communication. now she loves it. now she wants to do me, yikes lol

  8. The #1 thing that transformed the experience (after 20 yrs of 1/2 ass trys), this bit of advice: penetrator stays still. completely still. The penetratee is in control! Depth/speed/insertion, until comfortable. If it takes 20 mins to get 2 s in, so be it. And BREATHE!!

  9. IIve tried anal sex with 3 partners and honestly, even though I love it, I still get nervous and it hurts initially. My boyfriend now is a lot more sensual and patient and this has been the best anal sex IIve ever had hands down. Analingus and fingering can make a huge difference.

  10. I feel like my boyfriend will leave me if I dont get into this. Weve tried several times, with lube, penetration, alcohol. Id like to know how you say it shouldnt hurt at all!?! Slow wont make the difference when the tips in it burns like its ripping to hell! Help

  11. I want to do Anal with my boyfriend, I like anal plugs, but hes rather large and I know the tip hurts. What can I do other than buying trainers to work up to it? (My plug is quite a bit smaller than he is.)

  12. I think its good to have it, because your partner really loves it…
    just wash yourself and be relaxed…

    1. I actually got it from within my company (moved from a diff position), BUT the skills were learned all in my free time. Read other blogs, other forms of digital communication, books, magazine, practice, research best practices etc.

  13. I just recd a 6 x one and a half suction cup butt plug it looks too big for me, but Ill try it with lots of lube. I think Ill loosen up with several fingers first.. If it will stick to the shower wall, Ill try it there first. Wish me luck..!!!

  14. Myhusbandis91/2inchesandprettythickimsmallandthefirsttimewediditheactuallygavemeahemroidandnowimpetrifiedtotryagainbutIreallywanttowhatshouldIdonexttimetoavoidthis?

  15. I love having anal sex.The 1st guy i use to do it with knew how to get me really aroused 1st and was of average size.The man I’m with now is much bigge.He has gotten it in but he says it’s not all the way.Most of the time i won’t let him. I have a hard enough time with him getting it in the front.

    1. I feel you girl I went from 4” to 8”and big difference in girth the first time he tipped my ass I flew to the moon I’m creamy as soo as he’s in

  16. I have a question.if you get it half way in and suddenly it stops like it hit a wall or something and it wont go any further what shappening? am i not relaxed enough or something, because i got it half way in.please help…….

    1. We have two sphincters. One outside that we can control & one inside a little further up that we actually connot. Getting relaxed can help but is not a guarantee. I dare to say that your second inner sphincter was closed and would/did not open. DO NOT ever have him force as this could damage tissues

  17. The key tip is to only put the head in for the first few times. You have to keep pushing back, even if it hurts. Most women actually like anal, but it takes time for anyone to get used to it.

    1. Actually, “just keep pushing back even if it hurts” is NOT a good idea. Pain is your body telling you there is a problem. You can 100% have anal sex without any pain whatsoever.

  18. If we use the desensitizing gel, should my partner wear a condom to avoid it from desensitizing him?!

    1. Actually, when doing anal, desensitizing gel is NOT a good idea. Pain is your friend and will tell you if something is wrong. It’s better to go slow and use lots of lube. Plus, the cooling and warming stuff won’t be good for the delicate membranes/tissue in your bum.

    1. Everyone is different. Even for me, sometimes I can do it, and sometimes the stars just don’t align. This sex act won’t benefit from rushing or being impatient. Take it slow (like REALLY slow) and relax. You can also try anal trainers if you’re having significant problems. Good luck!

  19. I have tried different lubes and it still hurts ! Feels like sharp knives sliding in and out! Help! I want to like it… but the pain is too much

    1. Girl u shall do what I did buy a butt opener that’s so helpful cuz It feels so good Believe me I used to hate it but I love it, and our mans love it to.

      1. Ok my man wants this i have tried it once in another relationship and it felt like i was gonna puke i got so sick to my stomach and no matter how slow or relaxed i was it hurt so bad and made me sick i want to do this for him because he feels that this will mean im truly giving myself lf to him help

  20. Before i had my baby all i wanted was anal but it seems since i had her its nust painful want can i do i know my husband likes it but its uncomfortable for me.

    1. Do you by chance have any hemorrhoids since giving birth? If you arent sure you can have your gyno check and request any to be removed. This is my problem, I used to enjoy anal play but now its uncomfortable and painful, waiting to have it removed before trying again.

  21. I find that i have to have nipple stimulation from my husband during anal sex. Orgasms are just as great through anal as well. There is an HBO special on anal sex that I think would help a lot of couples. Cant remember the name though. Sorry

    1. It’s not just your anus, but more “you” as a whole. Dont hold your breath, actively try to relax your body, keep breathing. if you fee your anus tensing, have your partner stop and pull back a little until you can calm down again. If all else fails, try anal trainers.

  22. My husband and I tried.. We even tried lube but it wouldn’t happen? What can we do for it to work?

    1. Maybe try anal trainers first (start on the smaller ones) and then see how things go from there?

  23. I love anal sex but my bf wont do it. I’ve tried to get him to read this but he still wont stick it in my ass no matter how much I beg. Guess its up to myself and my toys. Sucks. I like anal better than vaginal sometimes cuz the orgasm is off the chain!!

    1. That man doesnt know how extremely lucky he is…hes missing out on some really great sex…id give an organ to have a woman that loves getting buttfucked…

    2. If my girlfriend begged for it I wouldn’t even think twice because she does things to make me happy and I do things to make her happy because we love each other

  24. I like it,I liked it off and on sence I was14I tried it once with my boyfriend.I some times let him finger me while he goes down on me and he likes it as well.My boyfriend said it feels the same and he could not feel any different say all. But sometimes I get scars 2tell him or telling him I want it

  25. My wife said she doesn’t like it but she lets me in and after easing in and pumping away she said
    “God I love you” so does she like it or what. All I can say is it’s great on my end.

    1. “She just wants to make you happy”. My wife is the same way. I asked her and that is what she told me

      1. No. This kind of thinking is why so many women hate sex. I felt guilty telling him to stop, I didnt want him to get angry/upset/frustrated and I dont really like sex anyway so whats one more uncomfortable/painful/humiliating thing?. For many women, these phrases cover their entire sex life.

        1. umm so many woman do not hate sex, my girlfriend loves sex just as much if not more than i do. so i dont know who you have been having sex with, but dont assume most woman feel the way you do because ive never been forceful or pushy about sex only if they r just as excited as me

        2. If you arent ready to tell your lover no than you are not ready for an relationship at all

  26. first time try and it just did not go right at all. All i wanted to do is poop. It was extremely painful which caused me to be in tears.

    1. Jess- i hear you completly i was in tears as well i felt like i had to poop very embarassing. But it hurts once they try and put it in but once its in all the way it doesn’t feel so bad. They have to make sure they go very slow. That and i hate to say it but yes you have to be able to calm yourself

  27. Your not out of luck !
    That’s your wife and lover ,communication is the secret in a marriage .
    It’s like almost anything else you’ve tried, doesn’t go as well as you hoped sometimes go very very slow and gentle.
    Sex with your wife is not a timed event

  28. Great article! Just wish I read it sooner. My wife was willing to try it, but I went in too fast. Now she’s scared to try it again. Any suggestions, or am I out of luck?

    1. Give her time. Maybe have her read the article too? Also, she can try on her own with toys or anal trainers.

  29. I guess ill try with lube. My bf be asking me for it but we done it before but it hurts. So ill try playing with it to loosen it up. Maybe buy some anal beads. Its just uncomfortable to me. But if he’s willing to leave me over that then he can go.

    1. Hi I recommend stretching urself to fit ur whole hand then if his peckrr still hurts u try stretching ur hole further. Go slow one two three four fingers then a thumb in ur bum. Show him what a girl can do or shouldnt do to there hole(s). Also I saw a guy get his hole arm up there on one porno.

    2. Getting deep is next step… I love it except only can feel whats up there with my fingers. My hand usually gets too sore as Im too tight to get hand all the way up my ass. Great to wank off while up there too. Epic orgasms makes my ass flap open then shut.

  30. My man has been asking for it, i only let him put the tip but it hurt a lot & well after reading this I’m going to try it out. Is Vaseline good to use?

      1. I tried anal it was very painful even though the guy was going slow it hurt like hell. I didnt bleed or nothing it hurt what should i have done better

    1. Easier to do if you have dual stimulation vibrator on your clotoris relaxes your muscles and slightly distracts you from insertion in the anal cavity

  31. Great work…clearly more to it than the average dude wanting to get crazy with the wife on a drinking night.

    1. Nick – Mostly yeah. Although some girls have that magical porn star butt that can take anything.

    2. My bf and me wished to have anal sex… He kept telling me to calm down… I mightve kinda gotten scared and moved.. Now it wont stop hurting…. I told him to stop but he didnt…. And I dont know what went wrong

        1. Maybe it felt so good and he didn’t hear anything. If she screamed or yelled maybe. A lot of people lives are ruined because people like you start rumors. Unless you are an ear on his body,and know he heard what she said don’t confusion.

      1. To fast just go slow you can’t suppress the booty you must ease into the first injection of the pleasure cane or really relax in the beginning

      2. I think your boyfriend should allow you to try it on him so that he can experience the sensation, especially if he goes to fast. By doing this, he will understand how much it can hurt if not done correctly. It cant hurt to try this (no pun intended).

      3. What went wrong is that he didnt stop when you asked him to. Like Robyn said, butts have a mind of their own. Sometimes it works and sometimes it doesnt. He should have stopped. Im sorry that happened to you. Thats very upsetting.

      4. Im so sorry he didnt stop! How are u feeling after all that? If dont right and both willing it can feel really good. I discovered i squrit with anal.

      5. Yeah that is exactly rape. Nobody is entitled to ANY penetration. I hope you’re in a healthier relationship by now.

    3. My anus bleeds every time after sex, But when I poop, there’s no blood. Should I be worried?

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