How To Have Anal Sex For The First Time

how to have anal sex, bad girls bible, sean jameson

After you try it a few times, you’ll find that anal sex can be just as pleasurable as regular sex.

If you have never had anal sex before, then you are in for a surprise. It’s very pleasurable when done right. Many couples have not tried anal sex for a variety of reasons or beliefs they have about it, like:

  • It’s too sore and painful.
  • It’s dirty.
  • It’s slutty.
The sad thing is that these things just aren’t true when anal sex is done right. But how do you have anal sex properly?

It’s About 2 People

Having anal sex with your man is perfectly normal and fun. But is it what both of you want? If your boyfriend is not very mature, he may think that having anal sex is really ‘cool’ and something to brag about to his friends. He may not be mature enough to see as something fun that you do together. So before you jump ahead and have anal sex with your man, you think about it first: Is anal sex something that we both want?
One of the coolest things about having anal sex with your man however is that it shows him that you are adventurous in the bedroom and are interested in trying new things with him, which is a major turn on for practically all guys.

Preparing Yourself For Anal Sex

Quick Note: If you want to learn my most powerful dirty talking phrases, tips & techniques, then you will learn a lot from this dirty talking tutorial video. Enjoy!

So if you’ve decided to have anal sex with your man, then there are a few things that you’ll need to do beforehand to make sure that it’s really pleasurable for both of you.

The first thing that I advise for your comfort is to make sure you don’t have any pubic hair around the outside of your anus. This is simply because as your man enters you, his penis can catch this hair and push it into your anus, which will make the whole experience of anal sex quite uncomfortable.

The next thing is to make sure you are really clean down there. Obviously this means making sure that you thoroughly clean yourself on the outside. Being clean on the outside is important, but so is being as clean as possible on the inside. So this means for about 24 hours before having anal sex with your man that you need to avoid any foods that will give you strong bowel movements. So avoid excessive caffeine, black liquorice, raisins, and all other foods that act as laxatives. This will help to prevent any nasty accidents or surprises during sex.

A Little Anal Practice Goes A Long Way

Far before actually having anal sex with your man, I advise that you do a little experimentation on yourself first. Put a small amount of lubricant on your finger and slowly try to insert it. You may notice that it feels a little sore initially when inserting your finger. This is to be expected. The pain is caused by your sphincter muscle. It’s just not used to having things to pushed inside. But once your finger is inside, then leave it there motionless for a few minutes. Your sphincter will almost totally relax making it a lot more comfortable.

Now try  gently taking your finger out and sliding it back in again. It should be a lot easier this time. Keep slowly pushing your finger in and out for a few minutes. 90% of girls find this action mildly arousing. If you enjoy it, then try something a little bigger, like a dildo or vibrator. Again, it may feel a little sore at first (especially if you insert something that is very cold). But if you leave it there motionless for a few minutes initially, your sphincter will relax and it will become a lot more pleasurable for you.
The more your practice, the less painful it will be each subsequent time.

How To Have Anal Sex With Your Man

If you have never practiced on yourself beforehand, then the first time you have anal sex with your man is probably going to be quite sore. This is because your sphincter muscle will have a serious problem trying to relax. But if you have first practiced on yourself, it will be much easier and very pleasurable.

The first thing you need is a good water based lubricant (also known as lube).

You absolutely must use a water based lubricant. Do not use an oil based lubricant as oil based lubricants can damage latex condoms making them degrade and more prone to breaking.

It’s always better to use a little bit more lubricant than you think you’ll need. Rub the lube over your man’s penis and around the outside of your anus. Before he enters you for the first time, I recommend that you first warm up on yourself by inserting a finger or even something slightly bigger. After warming up on yourself it’s time to take his penis and start having some anal sex!

The easiest position to be in when first trying anal sex is doggystyle. Here’s why: Your man can stay completely still on his knees, while you can slowly push backwards onto his cock. In other words you have complete control of how deep and how fast you take him.

Make sure to tell your man to stay still at first and explain to him why it hurts (the sphincter) so that he understands why you need to be in control. It may initially take a few minutes for you to fully take his dick in your ass. But once it’s in, make sure to stay still for a little while so that your sphincter can relax around it.

Once it’s relaxed, you can slowly start thrusting forwards and backwards or you may first want to take a little rest and get your man to pull out before trying it again.

The most important thing is for you is to be in control. Your man needs to know that it can hurt a little bit at first and that you need to control things at the start. Once you are comfortable, your man can take a more active role and start thrusting into you.

You’ll find that:
The more you have anal sex with your man, the more your will enjoy it.

At first it can be a little uncomfortable, but once you get used to it, you’ll find it as enjoyable as regular vaginal sex. Just give it time and make sure your boyfriend or man understands this.

4 Awesome Things About About Anal Sex

  1. It adds another way that you can have fun in the bedroom with your man which is crucial for keeping him satisfied.
  2. When you are having anal sex, it leaves you completely free to stimulate inside and outside of your vagina which can help you to have much more powerful orgasms.
  3. You can’t get pregnant from anal sex (but you can still catch diseases, so make sure that he wears a condom).
  4. You can use most of the sex positions you normally use when having vaginal sex.
If you enjoyed my tips in this article but want a true sex masterclass, then you may be interested in watching this blow job tutorial video where you'll learn my most powerful techniques & tips for giving your man incredible oral sex. Enjoy!

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  1. David Grubbs, RN says


    Ok, just hear me out… because I don’t want anyone thinking this is 100% birth control. No, your rectum does not connect you anything to cause pregnancy. Think about it like masturbating onto your partner’s vulva (the lips and stuff on the outside), this is because there is a SMALL chance that the little swimmers could swim all the way home. This is not very common, but it is possible.

    So when you have vaginal sex, and the man cums then (most of the time) pulls out. What happens then? (not sure how graphic I can be here…) Some of the semen comes back out and gets on the sheets, your panties, down your leg… you get the picture. Ever noticed that if stay still on your back or it comes out pretty quickly, that it runs down you to the bed… passing near / over / maybe even slightly in the anus.

    Now flip that over… You had anal sex. In my experience it comes back out pretty quick as I pull out. So where does it go? Straight down via gravity to the sheets… so similar to the above, it (quicker than you think) can come out and slide down to your vaginal opening. How close are the two? If you don’t already know, (CLEANLY WITHOUT TOUCHING EACH OTHER) slide a finger in each hole at the same time. What would you say, MAYBE a 1/4″ on average? GUYS Note: Gently squeezing this area with your thumb and finger can cause pleasure for her and works great during oral. :)

    So depending on the amount of semen, umm.. how “open” it is either from earlier sex or just being able to very easily take almost any man (was that a politically correct way to say that? lol), how you wipe (STILL FRONT TO BACK), or if you get dressed quick and it all spills into your panties and then your “lady parts” are rubbing all in it as you move and walk. It is possible for enough semen to get in the vagina to result in pregnancy.

    As you can see, while not real common, but it is possible through “splash conception”. A quick survey of about 10 Google “hits” is where I get that number. 8% failure rate.


    1. You can go from vaginal sex straight to anal. BUT DO NOT GO FROM ANAL SEX STRAIGHT TO VAGINAL SEX!!! It makes for an unpleasant experience, as infections are very common.

    2. If “cleanliness” is a concern, when I first started I preferred to wear a condom for anal to be “cleaner” not for birth control. This can actually decrease friction and make insertion easier and a little less uncomfortable the first couple times. (Use non-ribbed or texture free condoms.)

    3. Once you are both used to it, I find that often her lubrication coming out from vaginal sex and all over my penis when I pull out is all I need for anal penetration. (Tried the first time after 5-6 regular anal encounters.) Just warn her before you switch, or make sure you know her body enough before you try this without a warning. Depending on gravity and how excited she stays, I often find that she stays almost as wet in the back as the front… but she REALLY likes it as she can have multiples “back to back” in either entrance!!! Before we met, she was 35, she had tried anal once and hated it, and had only had 6 orgasms total during intercourse in her life, now she has 6 in a row or more just during the anal part of things.

    4. With that said, here is something she will LOVE!!! Note: this technique requires the ability to continue trusting through her orgasms without cumming yourself, but it can cause her orgasm to be longer, or even trigger her to have her first “back to back” multiple orgasms if she doesn’t already!!! Before trying this, you must know your partner, know she is ok with anal, and that it is relatively comfortable for her because it works best when she has NO IDEA it’s coming. HERE WE GO… Have sex in a position that allows you easy access to the area and the ability to grab your penis. I prefer her on her side with me straddling her lover leg. (btw, this position can give maximum penetration, so if she likes it then slam it hard, BUT if you are longer than she is, be careful because you can cause her severe pain. Even if you have never hurt her from penetration depth before, sometimes you will with this position.) Get her worked up by getting her close and backing off a couple times until she is ready to explode!!! Then as she begins to orgasm continue to fully thrust until she is well into her orgasm, then (preferably before she comes down from her current orgasm) as quickly as possible pull out of her, line it up and gently but quickly (again, know your partner) slide your penis inside her rectum and begin thrusting in whatever way she likes. I have NEVER have a complaint from this as it tends to hold that orgasm longer while throwing her into another, often stronger orgasm. Even if it takes a few seconds and the orgasm subsides, she will likely orgasm again very quickly. With this technique, I have been told many times that this caused the anal orgasm to be significantly more intense than the vaginal ones preceding it .

    So… I hope that helps someone. If this thing lists how to contact me, you are welcome if I can help.


  2. Jason says

    Nice little post! A couple of things though, water based lubricant isn’t necessary. OIL based lubricants, like creams and such, can damage condoms but basically any silicone based lubricant that you can find at the stores these days are condom compatible. I personally prefer oil because it is SO much slicker than water based and doesn’t dry out.

    I also find the easiest way to take it is to lay on your side, spooning style. Because you are laying down your whole body is relaxed and as the receiver you can still push back on your man. You are more tense in doggy because you are holding your body up.

    Nice post though! I enjoyed it :)

    • David says

      What risk are you talking about? This is an example of why saying “all, always, every”, etc… can make you look stupid. Especially since one form of “safety measure” is abstinence… and if you follow that one I’m REALLY having trouble spotting the risk!!! Not trying to sound like an A$$, but it sounds like the biggest thing you are at risk of is a mundane sex life.

      Sure there is risk with any form of sexual contact… but at a point the risk becomes so minimal its basically non-existent. Ever heard the terms (am know the difference between) possibility and probability???

      Please explain the risk if you follow ALL safety measures (off the top of my head here are just a few of them to consider): Condom, lots of lube to help prevent condom breakage (and most women I know don’t like dry anal), go slow until things are “ready”, used a toy to stretch things a little bit first, both partners got tested, did your best not to “contaminate” the vagina, were on birth control (in case the condom broke & it was that time of the month & the sperm spread to the vagina), immediately cleaned up, both washed hands immediately and took showers immediately afterwards, cleaned the sheets properly, etc… So if you do all of that, what “very risky” issues are we talking about???

      I admit, I’m sure I missed something in my quick list there. Sure it is POSSIBLE that you could go to the local pool and swim in the water with a woman who just had unprotected anal sex and YOU (if you’re female) end up pregnant from it or there is a chance of either sex catching a disease… but let’s get real, what are the odds in that actually happening??? Sex is risky, it has been since before Christ was born. Refresh my memory, what is the “oldest profession”??? Ever since there were more than just Adam and Eve around, there has been a risk of catching a STD. (The new term STI was probable between just the two of them. Even with conventional sex, being safe, etc… it isn’t uncommon to get a UTI, yeast Infection, etc.. after having sex for several hours with a partner who you have been in a mutually monogamous relationship with for years.) {Note, that was not a religious comment… it was more sarcasm for those who don’t understand what BC actually means.}

      I am safe, I get tested, and I’m picky about my partners, but I’m not giving up sex because it is “still a very risky sex act” “even if all the safety measures is followed”!!!

  3. Allan says

    I’ve just acquired a 53 year old girl friend. She’d not tried anal sex before, but I was initially very slow and gentle fingering her and rimming her. She was utterly relaxed, and kept murmuring how nice it was. This is on her first time!

    So my middle finger goes deeper and deeper into her rear, and moves around inside and she loves it. So I think “Why not? She’s really relaxed and liking it” – so I add my forefinger and now she’s TWO fingers as deep as possible inside her anus on her first time – and still she’s saying how good it is! And there’s STILL no resistance….

    So I withdraw and push in a well lubed but pretty big thick black vibrating polyurethane offset rotating dildo, which once it’s five inches in I switch on and it’s buzzing gently and (invisibly) twirling around offset inside her anus – and STILL it’s her first time and now she’s bloody mad for it. I get the vibrations and the whirling to maximum – she’s almost babbling with pleasure. All on her first anal date!!

    I’m a lucky man to have such a woman as my lover. But the story is really to say that anal sex is horses for courses. She at NO time ever complained of pain or discomfort on her first trip down Sphincter Alley. I know I would have!! We went the full Monty next time and I got my cock really deep into her and man, she was just going wild! It was just slowness and patience and above all utter relaxation that gave her such an easy and joyous initiation. Take note.

  4. Ella says

    I think that person was referring to it being dangerous by unnatural orientation. The anus isn’t “meant” to be penetrated and sometimes it can cause injury, especially if the receiver doesn’t take proper hygienic precautions. As usual, first-timers are prone to bleeding just as they would with first-time vaginal sex. This leaves them vulnerable to more bacterial infection than they would be with vaginal sex.

    I personally have just started experimenting with anal sex and from my experience, it sounds worse of a painful experience than it really is. My misconception about it, that I think a lot of other girls have too, is that the initial pain of… insertion… lasts through the entire insertion process, or in more blunt terms, that the pain you feel when a guy first inserts his penis “head” in lasts throughout the entire time he continues to push inward. This was not the case at all, for me at least. I’m not sure if that is what the term “rimming” is, but once my partner and I got past that initial step (which did take some practice and patience, as described in the article), it was smooth sailing.

    It really is a new, fun experience if you and your sexual partner are ready to take the next step in being intimate with each other. I do agree that it is something that needs commitment especially since it can be quite painful at first I used to think it was dirty and unappealing, but if my opinion on this can be changed I am sire it can be for anyone else.

  5. Candy says

    I am interested in anal stimulatIon for my boyfriend. He has penetrated me anally and has now expressed an interest in me stimulating him anally. Any tips on that subject?

    • says

      Hi Candy,

      You just need to use the same techniques as he uses when having anal sex with you, although you will obviously need to use a strapon or butt plug in this case.


  6. Cherise says

    For comfort in entering anally, it works to be really turned on before anal entry. Deep kissing, squeezing nipples, rubbing the vulva and having vaginal sex for a few minutes first really helps to relax the anal muscles. Using lots of lubricant, the penis can push slowly, and if there is any tightness at all, withdraw and wait until the woman feels ready to do it again. The second time again entering slowly will be more relaxed and ready. If the woman rubs her vulva hard as entry happens it will more likely be pleasurable . If not, withdraw and try again when ready. Certainly it helps to have a caring partner who you can trust to be gentle. Once you are warmed up you can go pretty hard and it’s likely to give you a really great orgasm, more than you get vaginally.

  7. Stacey says

    I’ve always enjoyed anal sex, it usually came doggy style. I haven’t dated in many years, but a male friend recently sent me a dildo, well, superb. He wanted to watch me, so I videoed everything for him. This was the first time I ever got into different positions for anal. Including laying on my side as mentioned previously. I just love anal, and when you’re doing for yourself, positions are key, I can get doggy style in but it strains my arms, the easiest, most comfortable, with less arm straining I’ve found for myself is to lie on back, knees to chest, spread or not. I love anal either way, and men who actually know what they are doing in bed are superb. I’ve recently got completely involved with a bodacious beautiful man I grew up with. WE haven’t had sex yet, I’ve been saving myself for my perfect man, the last man I’ll ever be with. He will enjoy me completely, my sexual appetite and desires have only increased over the years. Wow, it’ll be intensely awesome. I’ve noticed though, reading your bad girl bible, I was doing everything right from the beginning and I’ve learned so much as well. (Its been about 7 yrs now since I let a man touch me) And I’m ecstatic that I’m giving myself to my “Perfect Man”., and what I have in-store for him. WOW!!!
    So a super thanks to you Sean and all them guys that actually made some really great and reinforcing comments about their experiences. I don’t understand why women aren’t more giving to their own men, no wonder stuff happens in relationships bc of sexuality.

    • says

      It’s not. It could be nervousness, but if it’s very painful, that your body telling you that something isn’t quite right. Listen to your body and talk to a doctor if it’s quite severe.

  8. anonymous says

    I know this is a rough subject to bring up, but i was raped through anal sex several years ago – it caused some physical damage inside me in addition to a temporary sickness.

    However, now I’m dating someone that i love and trust, and i know he would like to explore anal sex with me. Once i told him my situation, thankfully he respected my initial boundary of not wanting to do that.

    Now i wonder if i should try it with him, but I’m afraid it may be more difficult than trying to get the sphincter muscle to relax. Any ideas?

  9. Honeybee says

    I am curious if anal sex is okay during pregnancy? I am six months pregnant. My husband and I tried it once before and while it wasn’t painful, I didn’t find it pleasant either. I think if we took it slower and tried your tips I might enjoy it more. I just want to make sure that I am not doing anything I shouldn’t be during my pregnancy, or that pregnancy might somehow effect how it feels.

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