How to Do Anal Sex for the First Time

If you want to try anal sex for the first time with your man, search no more. We have all the answers you are looking for.

We’re taught from a young age that anything to do with our bottom is dirty, and we’re encouraged to be clean, which includes ‘clean thoughts’ – don’t talk about your toilet activities, especially in front of strangers!  No wonder the idea of anal sex sends us off on a private, guilty curiosity spree. Cultural baggage has a lot to answer for.

Personally, I think that every part of the human body deserves sexual exploration. Anal sex holds the potential for some thrilling and very intimate pleasurable discoveries. If you’re curious and want to know how, here are some useful things for you to consider on your journey…

Acquaint Yourself with Your Anus First!

First Time Anal

Most of us started our sexual journeys by fiddling with our clits, so why should anal sex be any different? There’s nothing to be squeamish about when it’s your own body and you’re doing it in private.

Have a nice soak in the bath to get yourself all clean and relaxed. Get some of those essential oils burning. Make sure you have some baby wipes, a water-based lubricant and any sex toys at hand, and that your nails are filed neatly. Then settle down for some very intimate self-exploration!

It’s important to be turned on before you start poking at your behind.  One girl I spoke to suggests watching some soft porn to get your juices flowing.  Or you may just want to have some music playing, close your eyes and fantasize.

Start out by playing with your nipples, clit and vagina… turn yourself on… you know how to do it, you secret little horny nymph.  Use your dildo for some penetration if you like, but don’t let yourself come! You want to get yourself into a tingly state of slowly built-up anticipation.

Lube, Lube

Then, using plenty of lube venture further south and start rimming your anus entrance slowly and gently with your finger.  It will feel very different.

Keep it going, and keep rubbing your clit or G spot with the other hand. (Never mix the hands up. It will lead to all sorts of unpleasant and very un-sexy after-effects that will put your sex life on hold for a good week or more!)

As you get more and more turned on, and everything starts to naturally ‘open up’ you may feel that pleasurable sensation you get when you go the toilet. This could be the time to rim a little deeper, making sure your finger is always lubed up.

The wonderful thing is that there is nobody watching, nobody pushing. You can literally go at your own pace and only do what feels good to you.

Once your finger has been fully inserted you can feel around and see what feels good. Poke in and out using plenty of that lube, and different depths and enjoy the feeling of your anus contracting and opening up.

You should be experiencing some amazing sensations, and a satisfied feeling of ‘fullness’ if you are still playing with your clit and/or inserting your other fingers or a dildo into your vagina at the same time.

Try using a vibrator around the anus for an intensely pleasurable G spot or clitoral orgasm!

Having Anal Sex For the First Time with Your Man

Having Anal Sex For the First Time with Your Man

Once you have thoroughly explored the area by yourself, many of the most common fears and insecurities will have been dealt with.  It’s not a dirty experience after all, is it?  Except in the kinky sense of the word.

And if you’ve taken the time to relax and turn yourself on, and you have used plenty of lubrication, it’s not painful either!  The idea of having Anal sex with your partner on the other hand may be leaving you feeling vulnerable… which is perfectly normal, and perhaps part of the fantasy for both of you.

Anal sex (especially anal sex for the first time) carries implications of domination and submission which can be very sexy when there is mutual trust and respect between you and your man.

Before you dive into having full-on Anal sex with him, start out by getting him to play with you. It will feel different having someone else touch you down there, and your body may not react in the same way as when you experimented alone.

Is it possible for a woman to reach orgasm through anal sex? Yes, it certainly is. Find out why, and how.

Sexy Build Up

Anal sex should always be a slow sexy build up, and you both need to be comfortable and familiar with your anus and how it reacts before his penis goes anywhere near it.  He has to appreciate and respect what it’s all about first – it’s not just a tight hole for devour like all the porn sites suggest!

Don’t forget to use plenty of heavy water-based lubrication.  Your vagina is self-lubricating, your anus is not.  It will be susceptible to tiny internal tears which will be painful and can cause infection.

Penetration for the first time will be a team effort. If he barges his way in it will hurt. Your anus has two sets of sphincter muscles; internal and external. The external ones you can control at will, so you may think you are relaxed and ready for penetration, but the internal sphincter muscle will contract like a reflex as soon as his penis tries to enter.

It’s like an automatic ‘no entry gate alarm system’  It is important for him to ease his penis in gradually by inserting inch by inch and pulling out each time until the muscles relax and ‘accept’ him. It can help if he is kissing you and playing with other parts of your body to keep up the stimulation.

The Most Difficult Part

The most difficult part will be pushing the head of his penis past your anus hole.  It can help if you squeeze your muscles when you breathe in, and relax them when you breathe out.  When you relax he can then slowly push the penis in a bit.  Sounds a bit like giving birth to a baby, but the opposite way around, doesn’t it?

Now there’s one thing to be prepared for. Once he gets the head of his penis past the sphincter he is going to feel a distinct difference. The sphincter will continue to constrict tightly around the shaft of his penis. But, inside the rectum there is a lot more room, and some men may find the sensation confusing.

It’s not unusual for a guy to lose his erection at this point.  But don’t freak out!  It doesn’t mean he has changed his mind,. I’s just a physical reaction to the change of environment. His penis simply needs to adjust to the sudden and perhaps unexpected change of sensation.

Once he’s in, make sure he knows that he can’t just go crazy on you!  Having Anal Sex in real life is not going to look like it does in the porn movies. Those girls are on all kinds of relaxants and numbing creams – which to be honest kind of defeats the point, don’t you want to feel the sensations?  So go slow, be sensual, communicate and have a good time.

Toys for Anal Sex Fun

Toys for Anal Sex Fun

Now that you have all the basic information, here are some extra tit-bits. They will  help you enjoy and get the most pleasure from your Anal sexual adventures…

Always use non-porous, easy-to-clean silicone toys; like butt plugs, vibrators and dildos. It’s probably best to develop a collection of toys specifically for anal play. Even the tiniest trace of feces will cause nasty infections if used on or around the vagina.

Think about whether using them for anal sex for the first time or not…choice is yours.

When using toys make sure they have a flared base.  Things can get sucked into that little black hole you know!  And you won’t be able to get them out yourself… just saying.

Best Positions

If you are nervous about having Anal sex with your man, make sure you do it positions where you can be in control of the depth of penetration… i.e. woman on top! Explore these sex positions specifically designed for painless anal sex.

Doggie-style is perfect for G Spot stimulation. The space between your vagina and rectum is so thin that the penis will press up against your G spot.  And your man can reach round and play with your breasts and clit too – who says Anal sex is only pleasurable for men?

Try double penetration for a very full feeling and extra G Spot stimulation. Do it by introducing your dildo or vibrator into the mix!

And last, but not least, the most important thing to enjoy anal sex is that you are completely comfortable with your body and that you feel sexy. The more a guy wants you, and the sexier you feel in your body, the more relaxed you can be and in tune with the pleasure you are feeling. That’s why it’s great that you build a bigger, better, firmer booty that you can be proud of and that all men will chase you for.

You see, anal sex for the first time doesn’t have to be a frustrating experience at all. .

Chime in, share your experiences and ask questions in the comment section below. Do you have any tips for our sexy community of readers?

About the author

Scarlett Robinson

I am inspired by the ways people interact. Human behaviour and emotions are wonderfully complex, and I want to dig deeper and understand more. This is why I explore intimate relationships in my writing. (I’m also ever so slightly kinky.)


Click here to post a comment

    • Why thank you very much Melanie :) I’m glad you found it useful. Let me know if there are any other topics you would like to see covered!


    • That’s great news! Congrats :) Let us know if there’s anything else you’d like tips and advice on…

      • Hi I want try anal sex w my husband since I’m pregnant n it’s hard to have regular. But I’m petrified that it will hurt n ill tear n he will get stuck in my bum. We tried it before twice and it’s painful…wat should I do since we r both wanting to explore

      • Hi my fiance wants anal so bad but i’m so scared of it. We have tried it once and it wasn’t bad but i’m afraid now. I am good with blow jobs he is my 3rd sex partner and i once finish him twice in 15mins. No jokes but really am afraid of anal now

  • i am little bit afraid because it is my first time with him .. i mean in a different hole. And just tell me that it wont b that much painful . I am really afraid.

    • If anyone can tell me how to take a real huge penis in the anal without pain but more pleasure,please help us. My husband and I have tried the oils and fingers but once his head is a inch penetrated i am kicking him off IMMEDIATELY…help

      • I would recommend that you try to stretch it out as much as you can with fingers and toys beforehand.

  • I had anal sex for the first time today I was really scared about it hurting but my guy was asewome he was kind and very slow in the end I was loving it shame we had to part now I am so loving anal and I can’t wait for the next time :)) thanks

    • Hi Kayleigh:
      I am trying to convince my wife to try anal sex but there is no way. Something happen I thing first time…
      How would you recommend me to help her to wish it?.

  • i want to do anal sex but i m afraid that if i end up hurting her.what kind of natural lubes can i use during anal plz tell.

  • I’m a gay dude who’s just about to try this (or attempt this over the weekend) so thanks for some tips that can crossover (e.g. being calm, muscle control, plenty of lube etc). Feeling less worried now! :)

  • I have been married for 5 yrs. never had anal sex. My husband would love to do. I enjoy fingering at my vagina/anus but scared to sex at my anus. Could you tell me what kind of lubricant and butt plugs should I buy? Is it necessary to use condoms during anal sex. After reading so many blogs, I think I should have anal sex with my hubby.

    • Ok this might be a.weird question… but am scared im giving to fart or get p*op on his d*ck what this won’t happen.? Plzz help me!

  • I love anal sex with my girlfriend. I’m a girl so it doesn’t really work because she doesn’t have a penis. I still like it. I’ve never done it though.

  • I going to have anal sex the second time in my life.and the guy im dating about a month we were talk about sex so he was asking if I like anal I told him no because I had a bad experience with my ex bf he didn’t lubricate well so my ass hurted me :( I was in the hospital for a few days.very bad experience I had with that..anyways the guy im dating told me touch yourself and feel down below and feel ur but hole and told to use some lubrication and use one finger two finger’s and my thumb finger and told me to relax and I did. And Told me to use my vibrator to lubrication it too and take a deep breath which I did. It felt great I told him I never thought that sensation before and some really wonderful :) and I told him im looking forward to our candle light dinner and anal sex :) so I can’t wait for it wish me luck …… :)

    • Keep us supper excited to kno how it will turn out for you and your second chance of pleasure.

  • I got married 10years now and my hubby tried to do annal ws realli painfull and i got hurt.little bit blood came frm anas.m really scared now but my hubby alwais looking forward to do again.please any idea that shudnt be pain.i want to keep my hubby happy as i love him soo much.please tell me easy idea.thanks.

  • hey I’m a guy who loves anal but never have found a girl thats willing to try it every time i ask them if they like anal they say ew no so i hide it from them that i like it. How do i approach them and ask them to try it?

    • Well, in deed, anal is not any woman’s cup of tea. Meybe because they had bad experences in the past with it or maybe they’ve heard bad stories about it. Either way, the most important thing when it comes to anal is, i think, trust. Most women will not accept trying anal unless they are in a committed long term relationship with a man they truly love and completely trust because ultimately anal is about trust and closeness. So my suggestion is next time you ask someone to try it, think about these things. Also, approach them gently about it, and as suggested in the article, if she accepts, try some anal play sessions before actually doing it and be sure to discuss each and every aspect of it so that neither of you will have doubts. Good luck!

    • Take it slow get to know her talk about sex things she likes then stuff you like don’t be shy that you like anal tell them you never tried it that you would like to and explore more

  • Thanks for the tips me and my boyfriend have been talking about doing anal for awhe he have use toys fingers and lube but I always tense up when he starts to put it in but reading your tips I think might help thanks

  • My advice to any woman trying anal thr first time is lube up really good first then sit on his erected penis with your anus, that way you can control the depth and speed and it doesn’t hurt at all because your completley relaxed.It works i swear, I’ve been with the same guy for two years we tried anal sex for the first time the other night and when he had me bent over everytime he would gey an inch inside me i would get nervous because i was worried about the pain and i tensed& tightened up so much that we couldn’t go any farther so i thought maybe if i could control it it would be more pleasurable and i was right it wasn’t painful at all i actually went a little crazy rode his d*ck reverse cowgirl style while he was in my ass till he blew a huge load then i kept riding until he got off multiple times :) lets just say my man was very satisfied and so was i ill deffinatley be treating him to a f*cking like that really soon !

  • Thanks for the tips me and my boyfriend have been talking about doing anal for awhe he have use toys fingers and lube but I always tense up when he starts to put it in but reading your tips I think might help thanks

  • Hi, I have attempted anal before but the guy was too impatient. I’m now having my 2nd child with my long-term partner..normal sex has become uncomfortable because I became pregnant with my 2nd a month after my 1st child, so my body hasn’t really got back to normal…are there any tips?Im about 5 months gone. xx

    • H, I have been in your situation before and anal sex was a saving grace. Firstly, this article is AMAZING, it really gives you a lot of information that you need to know. I just want to stress that you have to be patient and you have to give yourself plenty of time. The first time you try it I recommend you use the spooning position, it is perfect for when you are pregnant and we kept on using the position (with a pillow under my belly) up until my due date. Try bringing your knees up to your chest as much as it is comfortable that should make it even better. Then, with regard to penetration a trick that I found works really well is to push out as if you are trying to have a bowel movement as your husband is inserting. It sounds weird, but trust me it makes a huge difference. When I was pregnant I was often very gassy and I would often pass gas during anal sex especially during the initial penetration, but it is a small price to pay for intimacy. Also I do not think the article mentions it, but initial penetration feels a lot like you are having a bowel movement. Do not be frightened, you won’t actually have an accident, it just a sensation. Good luck, I hope you enjoy it.

  • i read this article n never thought I could do it 2 my new girlfriend… then i started fingering her ass hole without actually askin to slide my d*ck in it, she reacted so well, i felt her squeezing her butt n my finger at the epicenter of her excitement. I wud have liked the same to happen to my d*ck so i got harder n hornier. she said she’d never felt that sweet!! it really made me be the man. Then she asked me to try my d*ck, it was painful to her even after lubin bt she promised to let me in samday soon! thnx 4 d article.

  • I wanna try anal but I’m scared because of all the stuff it says on here like I have to think it through its to much to take in but can I jus stay calm and relaxe when he puts it in tips on how to do and think it out easyer

  • I am 17. I do lost masturbation.
    Bt i want more pleasure with that.. So can tell me some techniques

  • is everyone on here 12 yrs old or what? wow i have never read so much bad grammer!!
    great article, might have to implicate a few of these pointers, everytime my hubby tries, it just hurts….i know i enjoy it because i have done it before, but with this one, it is just painful every time….

  • It is unhealthy and it is never meant to be as such and the biggest thing about it is that the male becomes impotent finally and both get multiple STD’s as a result. What a pitty!

  • Im tried it for the first time with my man im sooooooo super nervous and also suggest some good position to insert

  • Two things:
    Can you get STD’s from anal sex if neither you or your guy has an STD?
    And I’m a little nervous that some faeces might get on my man’s penis, is there something I can do to stop this from happening?
    Many thanks!

  • Its best to have passed your last stool a couple of hours or more before.
    Lube up properly, both the anus and the penis and fingers. Use lube and 1 finger to start to get the anus used to the invasion. Knock on the door by rimming for a while first, (tongue or finger) then push the finger in slowly and gradually, be gentle and take your time and allow the finger to introduce more lube internally. tbc…

  • Then use two fingers and again be gentle and take your time. Add more lube. When the fingers are in stretch them apart and/or pull them to the sides and all around a little to get the sphincter to relax more and accept the intrusion. When its time for the penis to enter, make sure it’s fully lubed and take it really slow. When there is resistance, stop pushing but keep up the pressure a bit before trying again. tbc…
    For the next slow and gradual push, the receiver can help the opening up by bearing down, as if pushing something out. This will open the inner sphincter a little and allow the penis to gain some headway. Stop. Then do the same again. After a few times, When the penis has pushed all the way through, stop and wait, let the sphincter get used to it. Slow short and gentle strokes at first folks! If at any time there is sharp pain, something is overstressed and about to tear or has torn and and it’s your body telling you to go no further and to withdraw. Also, withdraw slowly. Good luck and above all, Relax and Enjoy!

  • I’m going to try analysis sex for the first time with my boyfriend, thank you so much for the tips!

    • I had anal sex yesterday for the first time I enjoyed it… it was the first time for my boyfriend too… its anal sex is against our religion and rules but for I said him u want to try it… than he slowly put his funger into my b*tthole and lose it I loved that feeling I had little pain and it was like p*oping… hehe

      Well I have a question… what may happen if the fingers you used in the ass hole is being inserted to vagina without cleaning??…

  • My boyfriend and I have been together since 3 years and are having vaginal and oral sex from the last two years. And now my boyfriend wants to have anal sex and I do wanna try it too but I’m scared it might hurt. To make me feel comfortable he sometimes fingers me in the ass when we’re in the mood but I always stop him thinking it might not go well. I really want to do it too but just don’t know how to let the fear go away. Are there any tips or advice you can give that me and my boyfriend can try so that I can get comfortable and get rid of the fear I have in my mind and enjoy it too ??

  • well, this is the info i was looking for, but i was hoping to feel more at ease, but i think im more afraid!! but i guess thats kind of exciting too!! thanks for the article!

  • Me and my girlfreind we want try anul sex but she is afraid becouse she never done it before and my penis big what can help us do anul sex and enjoy it without any pain to her?

  • The ONE unanswered question in the whole thread is…. “Once they get it, they don’t want anything else… why??”

  • Iv never done anal sex yet but Id love to try it with my new girl friend we are both in our 50s she has done this with her ex years ago Iv never done this but my question is am uncut and my fore skin is very tight and will not go over the head of my penis I’ll be using condoms for safe sex but I need to know If I do anal sex with my girl friend will my fore skin split with a condom on me yes I can get water based anal lube