10 Steps to Great First-Time Anal Sex

Many people believe that anal intercourse hurts and that it is always an uncomfortable experience. This is quite simply false. If it hurts, you’re doing it wrong. Actually, anal intercourse can provide a unique form of pleasure for both men and women. Anal sex is enjoyable for men because the tight anal sphincter rings provide strong sensations to a thrusting penis.

Generally, for women, the pleasure derived from anal intercourse is due to the shared nerve endings located between the rectal wall and the vagina, and/or from indirect stimulation of the G-spot. The anus contains many nerves as well, which can also react in a pleasurable manner when excited. My post Anal Sex from a Female Perspective describes what anal sex feels like for a woman. If you want to try anal sex with your wife or girlfriend, but are uncertain of her reaction, use the approach I recommend in How to Make Her Want Anal Sex.

If you follow the ten steps below, you can ensure that your first anal sex experience is pleasurable rather than painful.

1) Get clean. It goes without saying that if you’re sexually stimulating an area that’s usually devoted to elimination, you need to ensure that it’s squeaky clean. Have a relaxing bath or shower beforehand and thoroughly clean the area. If you’re self-conscious about your lover seeing your anus in full for the first time, why not gently shave or wax the skin between your butt cheeks? You’ll be surprised how much more relaxed and confident this will make you.

2) Don’t rush into it. Engaging in foreplay or even intercourse before trying anal sex for the first time can help you relax. Analingus (oral-anal contact) is another great way to “warm-up” the anus and can be very pleasurable in and of itself. Run your tongue over the anus, licking it in soft, wet strokes, or circle it, running your tongue around the edge of it slowly and delicately. Flick the tip of your tongue rapidly over the opening, or try inserting your tongue as far as it will go pushing and stroking it back and forth. Try brushing your lips over the spot or sucking hard on the anus.

3) Use lots of lubricant. Since the anal region is not self-lubricating, anal lubricants are extremely helpful for making penetration more comfortable and pleasurable. Water-based and silicone-based lubes work well with both latex and polyurethane condoms. Many couples prefer a thicker lube (a “gel” rather than a “liquid”) for anal sex. Use as much lubricant as possible. You really can’t use too much.

4) Fingers first. The sphincter muscles around the anus will not allow things to pass through easily unless you start small and take it slowly. Apply lube to one finger and gently insert it without moving it around in order to condition her to the sensation of something being in her anus. Once she is comfortable with being dilated, slowly start to move your finger in and out and around. Gently stretch her anus by pushing outward on her anal ring, as if it was the center of a clock face, pressing out towards 1, 2, 3 o’clock, etc. Once she has learned to enjoy the insertion of a single finger, try inserting a second. Always go very slowly and be sure she remains relaxed. Don’t forget to use lube on each finger you insert.

5) Get in position. Choosing the best position may make the difference between a painful or pleasurable experience. Though doggie-style may be the most popular anal sex position, it’s not necessarily the best one for beginners. Missionary position (man on top, woman on bottom) allows the woman to fully relax her anus, making penetration much easier. My article Which Anal Sex Positions Are Best for Beginners? describes several anal sex positions, and tells you which ones are best for beginners and why.

6) Enter slowly. When you’re ready for penetration, take one or both of your hands and use your fingers to pull your butt cheeks gently apart. This will help guide him into your anus without too much prodding, making it a lot easier for both of you. He should begin by slowly and gently inserting the tip of his penis into your anus. Remember that it’s normal to feel some discomfort or even slight pain because it’s your first time (just like with first-time vaginal sex) though if you’re in a great deal of pain or feel very uncomfortable, ask your partner to stop immediately.

7) Go deeper. Once your partner has inserted the tip of his penis, ask him to slowly penetrate your anus further, but at a gentle pace that you feel comfortable with. This means it could take anywhere from 30 seconds to five minutes before his penis is fully inserted. Breathing deeply and talking him through what you’re feeling will help keep you both stay relaxed. Continue like this until his penis is fully submerged.

8) Gradually build momentum. Once his penis is fully inserted, the key to great anal sex varying the angle, depth, and speed of thrusting and gradually building up momentum. Clenching your anus can enhance the sensation for your partner.

9) Don’t forget the rest of her body. Stimulating other parts of her body during anal sex can help make her feel more relaxed and provide a greater thrill for both of you. While thrusting in and out, reach around and finger her clitoris. While orgasm may occur purely from the anal sex, this added stimulation will lead to a more intense sexual experience.

10) At the end. Immediately following climax, she may become extremely sensitive to penetration. Thrusting or pulling out should be done very gently after orgasm. Also, remember that once your penis has been inside the rectum, don’t put it inside anywhere else until you have washed yourself.

These days more and more men are becoming interested in anal pleasure and comfortable with the idea of letting their female partners take control in bed, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It.

Anal sex is one of the most erotic and satisfying sexual practices you and your partner can enjoy. It may take some time to get it just right, but if you follow these 10 steps, you will both have lots of fun trying. The most important aspect of anal sex is communication, so be sure to talk to your partner about your anal desires before, during, and after your first session of anal sex.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here

189 Responses

  1. Another tip that was posted on thebeautifulkind.com, is to have her push out upon insertion. Pushing out relaxes the sphincter and I have found that it works very well.

  2. Unless you are 100% sure of your partner’s STD and HIV status you might also consider using a condom.

  3. I mentioned condoms in Step 3, but I hope that enough people have heard about STDs and AIDS by now that we can skip reciting the dutiful “use a condom” mantra occasionally.

  4. [...] For couples trying anal sex for the first time, choosing the best position may make the difference between a painful or pleasurable experience. Though doggie-style may be the most popular anal sex position, it’s not necessarily the best one for beginners. My article Which Anal Sex Positions Are Best for Beginners? describes several anal sex positions, and tells you which ones are best for beginners and why. To make your first anal sex experience a great one, follow my 10 Steps to Great First-Time Anal Sex. [...]

  5. hi. i’m about to try anal for the fisrt time with my boyfriend (neither of us have done it before). However we have only just started exploring the anal region and he was planning we do it for valentines day but i’m not sure if i will be able to insert it in. i’m not keen on butt plugs or anything but will well lubed fingers dialate me enough ffor the main event?…

  6. Congratulations on getting up the courage to try something new! Fingers will work, but take your time. Your boyfriend should insert one, and then two fingers, massaging slowly, but firmly, until the sphincter muscles relax.

    Also, be sure to engage in plenty of foreplay and/or vaginal intercourse before trying anal. Being very aroused will relax you and make penetration exciting even if it’s a little uncomfortable at first.

  7. [...] it spread over here?http://observer.guardian.co.uk/Lifeandhealth/health/story/0,,2249374,00.html10 Steps to Great First-Time Anal Sex ? Sex SecretsEngaging in foreplay or even intercourse before trying anal sex for the first time can help you [...]

  8. Does it matter how big a man’s penis is? I tried with my boyfriend once before, and yes, I mean, we weren’t lubed up or anything, and I realize that’s a necessity. But quite well-endowed. And i was wondering if that would make it harder for me not to be in pain when we try it again…

  9. It matters some, but less than you’d think, in my opinion. A vicious cycle can get started by thinking “He’s really big, and it’s really going to hurt,” which causes you to tense up, instead of relaxing, and then, sure enough, it does hurt. Lots of foreplay, lots of lubricant, and entering slowly make a lot of difference.

  10. Thank you so much. Me and my husband had tried anal sex many times before but it always hurt oh so bad. And i knew how much he really wanted it so i was looking for help and i wondered upon this page. As soon as i got done reading these 10 steps i got in the bath tub to experiment. And it worked, i was gradually able to stick 3 of my fingers in there. After i got out of the tub i decided to show my husband. And BINGO! it worked. And god did it fill good. im just wondering why i was having the sudden urge to have to pee as it was feeling good. but thank you oh so much.

  11. You’re welcome. The “urge to pee” was probably because your G-spot was being stimulated, which causes many women to think they need to pee – at least at first. Even though the G-spot is inside the vagina, anal sex often indirectly stimulates it.

  12. hi my bf and i tried anal sex for the fist time and it hurt really bad. at first he didn’t use lube, the n he used a lube comdom, but it still hurt! also i was wondering csn u get pregant from anal sex?

  13. Obviously, you didn’t follow the “10 Steps to Great First-Time Anal Sex.” If your boyfriend already caused pain by not using lube (and also, I suspect, not following steps 2, 4,,5, and 6), that pain will still be there even though you used lube later.

    You cannot get pregnant from anal sex unless semen is transferred to the vagina.

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  15. my bf n i had sex for the first time. it hurt. im 19 n he is 21, i bled a bit but not too much. he came. i didn;t . will i still bled agaib as my bf has a big penis. alsowhat happens if he doesn;t make me orgasm. he has tried head but i didn;t orgasm :)

  16. If you’re talking about vaginal sex, you are not likely to bleed the second time because your hymen is already broken.However, if your boyfriend has a big penis, you may need to use lubricant.

    Women take longer than men to orgasm even under the best of circumstances. We often need at least 20-30 minutes of foreplay prior to intercourse in order to be ready for penetration and have any chance of climaxing from thrusting.

    If you’re talking about anal sex, you may bleed every time if you’re not relaxed and don’t use lubricant. Follow the “10 Steps to Great First-Time Anal Sex.”

    Try reading other articles on my blog to learn some techniques that you and your boyfriend might try to make intercourse more pleasurable for you.

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  20. my bf has a big penis and i have tried going through with it but everytime i do it my skin breaks and i give up please help!

  21. Fanseet, be sure that you’re strictly following the 10 steps with special emphasis on:

    4) Fingers first. Don’t attempt penetration with his “big penis”until you’re comfortable with two fingers inserted.
    5) Position. I don’t know if it’s at the guys’ insistence, but a lot of couples seem determined to ignore my recommendation of missionary position or beginners. Try it.
    6) Enter slowly. Slowly doesn’t mean seconds for beginners; it may mean minutes.

  22. My guy and I have tried anal several times. He’s very wide, so we always make sure 3-4 fingers can go in comfortably before trying it with the real thing and use plenty of lube. We’ve always tried in the missionary position, but in trying that, my legs are nearly over my head (I’m a dancer of 23 years, so it isn’t horribly uncomfortable), but I’m wondering if that’s causing me to tense up. He tries to get the head in and I try to just relax and bear it, but the pain becomes so unbearable that we have to stop. I also experience bleeding afterwards, even though he hasn’t really entered me…any tips…?

  23. It sounds as if you’re doing everything right. If you think that missionary position is causing you to tense up, try another. My post Which Anal Sex Positions Are Best for Beginners? describes seven altogether. You could also try one of the variations of missionary position described in my post 3 Great Anal Sex Positions.

  24. oh you should try it slowly if you wanna ocean of pleasure.
    and don’t even try to push it bluntly.
    i’ve already has it and i know what i’m talkin about!

  25. [...] she does, be sure to follow the 10 Steps to Great First-Time Anal Sex unless you want the first time to be the last time. A bad experience can turn her off to anal sex [...]

  26. Anal sex hurt so bad I was just wishing i would pass out. He begged me to let it happen a bit more. I was so gratefull I did. I have never ever orgasmed so hard or often. Stick with it don’t try to stop. Trust me you will not be sorry. THANK YOU ADAM

  27. Are enemas required before anal sex?

  28. “Are enemas required before anal sex?”

    No.

  29. My Bf doesn’t really like the idea of anal sex …. how do i get him to like the idea!!! I want to try new thing in our sex life and he is verrrry big but i don’t think bout that like he does???? I’m the one who wants to do it anal not really him???

  30. Amy, it sounds as if your boyfriend is afraid of huring you with his “verrrry big” penis. That’s sweet, but, ultimately, it should be your choice if you want to try anal sex with him. With a willing woman, a patient man, and lots of lube, penis size is not really a problem.

    One possibility is taking matters into your own hands and inserting his penis into your anus, instead of your vagina, in the woman-on-top position. If you decide to do this, I highly recommend inserting a large butt plug (since you say he’s big) several hours before you expect to have sex. Then, when the time comes, remove the butt plug, insert his penis, and voila – you’re having anal sex.

    Your boyfriend will definitely like the idea of anal sex once his penis is buried deep inside you,

    Good luck!

  31. Well Okay, a few more things…. I read this on Monday and have been inserting a ( banana toy) =-) in me since than , 2 times a day!!! Is that okay??? It FEEEL REALLY GREAT!!! Its not as big as him,Is that ok? But i ‘m getting the feel of something going up my butt..I am younger then he… We have sex 3-4 time out of the week the most and its great.. But i feel as if we expand our sexuality with each other…. We met on a sex basis .. We been together for a year. The first time we tried anal sex it didn’t hurt me. It hurt him so we never try it again !!! But we r going to try it this weekend with all the tips u have gave me.

  32. One more thing, what is the BEST Lubricating jelly to get?? I really don’t want to get u know what all over his penis……. I don’t want to get a sticky one or greasy messy one, so what would you require for me to go get ???

  33. If it feels great, Amy, it’s probably okay. Two good lubricants that you can find at most pharmacies are KY Jelly and AstroGlide. Using a lot is more important than what kind.

  34. [...] A Guide for Men and Women, lists ten rules of anal sex. Once you learned the rules, my post 10 Steps to Great First-Time Anal Sex will guide to to a pleasurable anal sex experience. Anal Eroticism is surrounded by a powerful [...]

  35. My boyfriend and I just tried anal sex and he came in me… The next day it was still there and it was kinda dripping out …How can i solve this

  36. The only guaranteed way is to use a condom.

  37. [...] 10 Steps to Great First-Time Anal Sex If you follow the 10 steps below, you can ensure that your first anal sex experience is pleasurable rather than painful. [...]

  38. omg i tried your techniques with my gf (im a lesbian).. and they worked vey well.. she always complained it hurt every time we tried so id get frustrated and stop. my strap on is made of cyberskin, its the next best thing next to skin, and i had tried other techniques before. so we visited this site and the results from your steps were amazing!!! she loves anal sex now!!! i tried everything i read as soon as i got done reading your steps and she cant wait to do it again! thank you!!!!!

  39. Thanks for the feedback, Tiara. Anal sex is pleasurable for anyone – regardless of gender or sexual orientation – when it’s done right.

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  44. I didn’t read everyones comments, but I have attempted anal before with my boyfriend and we are never able to go through with it because I always feel like I have to use the bathroom.
    I just found these tips, so hopefully this will help us with our other poblems. I feel that not only should there be tips, but there needs to be info on how to prep yourself for anal. We have learned from experence and from the people at Hustler. But you need to detox your body because I have learned that if you don’t, you have the feeling of going to the bathroom a lot.
    No one ever seems to mention this for first timers and I feel it is important.

    Thanks for the advise!! I can’t wait to improve what we have been doing with these 10 steps.

  45. Some people may want to take an enema before anal sex, but that’s not a must for everybody.

  46. I’ve done anal sex with my wife for almost 30 years, at least weekly. She likes it best if I cum inside now, though we didn’t start out that way. She’s still as elegant and does it just as beautifully as when we started. I love her intensely, because she got used to it for me, and knows how much I like her that way too.

  47. During sex i usually feel like i need to pee alot . I have heard this is stimulation. Usually i hold this urge in . would you reccomend letting it come out or what should i do when i feel this . it usually distracts me from intercourse when i begin to feel i need to go to the rest room.

  48. If you don’t think logically that you really need to go to the rest room, the feeling is probably your G-spot being stimulated. My post The Secret to Female Ejaculation explains. Be sure to urinate before sex, and then don’t let yourself be distracted. Go with your feelings and let it come out. It will be amazing.

  49. I have anal sex with my long term gal 95% of the time… and it is still always great.

  50. would you please e-mail this to me.

  51. me and my husband has tried anal sex a couple of times…why does it feel like i have to go poop..i am scared that i will..i liked it from what we have tried..i always make him stop cause i have that feeling..can you tell me why and what we can do to help that..i know i dont have to go when we try tho

  52. Hi Brittany,
    As your husband’s penis slides in and out of you, your anal sphincter relaxes as it does when you have a bowel movement. That’s why it feels the same to you. To reassure yourself that there is no possibility of feces entering the rectum during anal sex, either have a bowel movement three hours before (or less) or take an enema. Once you become accustomed to anal sex, neither will be necessary though having a bowel movement beforehand (if you can) is always a good idea.

  53. Hi svetlana,

    My bf and I had anal sex for the first time last night, after he finished I noticed that i was bleeding from that area, is that normal?

  54. It happens, but it’s not “normal.” Use more lube, and your bf needs to enter more slowly and not thrust hard until you’re opened up.

  55. how i can overcome the feeling that was not yet ready for anal sex? my BF really wanted to try on that but the 1st time we did it, it was nothing! i feel so hurt. but i really wanna try this. its just happened that i am afraid to be hurt again.

  56. If you’re talking about being physically hurt, following the ten steps should keep anal sex from hurting. Use lots of lube and go s-l-o-w-l-y.

  57. can you die of having anal sex?

  58. hey my name is Maria, I’m interesting in having butt sex, this will be my first time but I’m afraid of having any health risk, I’m afraid that my bf hurts me so badly and cause me death, so I would like to know if there is any risk of having anal sex, such as death or any disease, I need your opinion!

  59. If you follow the 10 steps, the risk is almost nil.

  60. Not if you follow the ten steps.

  61. I want to have sexual interourse with someone i’m still searching can u help me I’m frm india!

  62. How could I help you find someone to have sexual intercourse with in India?

  63. hello. my fiancee and i have tried this with lots of lube on one finger and i got the finger all the way in. i was licking her vagina while doing this and she had an orgasm and said it felt better with my finger up her anus while moving it around inside her. but as soon as i start taking it out even a tiny bit it really hurts her, even while i still lick her. there’s no way of doing anything without hurting her. if i can’t do it in and out really slowly with a finger how am i supposed to do it with my penis? I followed all your 10 steps and i really want to try anal sex but my girlfriend just can’t.she was relaxed and excited about it and everything but we still couldn’t do it. i thought any woman can have anal sex if she gets used to it?

  64. Moving in and out is not really feels good during anal sex, but it sounds odd that taking your finger out is what hurts your fiancee. Normally, it’s putting it in. My post How to Make Her Want Anal Sex goes into more detail about teaching a woman to associate anal play with pleasure. Putting a finger in during cunnilingus is an ideal start though. As I said, moving your finger in and out is not what feels pleasurable. Instead, try an anal massage. This not only feels better, but should also relax her.

  65. Sure I’ll try it!! n thnks fr d tip..

  66. me again :). But how am I supposed to have anal sex with my penis if it hurts her taking it out. I read your “how to mke her want anal sex” and used that aswell. She really wanted it. I just don’t know how to get her to not feel any pain with using my penis. Would numbing cream help if i were to still take it easy and slowly?

  67. I don’t recommend numbing cream because pain is information. If she really wants anal sex, she could try my recommendations in my post How to Have Anal Sex with a Big Penis.

  68. hii dis is sandy..i want anal sex with my gf.any experienced gal plzz tell me hw 2 do .09579802663

  69. Thanks I read through the steps im going to try it out tonight.

  70. http://www.utterpants.co.uk/news/sex/analscourge.html what do u hav to say abt this?? As much as male-desire dominated porn industry wants to make-believe that it is as much fun for women as men, articles like the above seem to clearly say that it’s no fun at all for women! Of course I luv it, but only if a woman can genuinely do so as well!! I am not someone who will ever do anything that my woman doesn’t like in sex. All the steps and description to great anal sex u hav r no different from any site discussing this today…but the real question is, can women genuinely luv it?? I somehow find it difficult to believe that most of the women can’t get these steps right leading to all the problems discussed in this article….

  71. http://www.utterpants.co.uk/news/sex/analscourge.html after reading this, it is difficult not to think that almost no woman enjoys this act! Since the steps you discuss are pretty much the same as what you find in myriads of anal sex sites, it is also difficult to believe that none of these women get it right! Make no mistake, I am someone who has naturally loved (heterosexual) anal sex more than everything else as the ultimate fantasy from my early teens when I started thinking about sex. But all the same I am someone who will not do anything that a woman does not like. So, it makes me wonder, with sadness of course, whether this should remain a fantasy forever?? If whatever you have discussed in your blogs go beyond business to honest and self-experienced facts, could you at least tell me how on earth one can figure out whether your woman genuinely likes it or is faking it for a man like me to attempt it?

  72. I had sent a comment yesterday, where did it vanish? Removed?

  73. Not removed, just not approved yet. However, if you spam my blog with that link again, all your comments will be removed.

  74. Thanks Svetlana! I know you have sounded nice all through your blog, and continue to do so. Feel free to delete duplicate content (my first one on that link) as well the further replies including this one. But I am waiting for an answer from you on “how to find out whether your girl REALLY loves it or is faking it”?? Given that women seem to know the art of adjusting to men’s demands without showing it, this is a genuine concern!

    Thanks

  75. In my opinion, the best way to be sure that your woman really loved it and wasn’t just faking is how she behaves AFTERWARD. Is she affectionate and loving towards you – especially physically? If she is, she probably enjoyed it because she continues to want to touch you and be close to your body. If she doesn’t seem to want to be physically affectionate toward you afterward, she was probably faking it to get it over with. I hope that doesn’t touch a nerve, but it’s the truth.

  76. Hi…my bf has had anal sex before but I have not successfully (many failed attempts) and I would like for it to work with us. He tries with his fingers but my fingers feel more comfortable than his =/ I’m going to try your steps, they seem very helpful!! But my main concern is im pregnant, so what position is best or should anal be avoided during pregnancy?

  77. My wife loves it now that she is used to it. Takes some warm up. Guys, make sure your um “member” hits her um “front” wall some, this really stimulates her better. She tells me that she gets a massive full body big “O” from this when it’s right. girls-find a guy you can trust to take time and explore, not in a rush to satisfy himself. Then you can enjoy it, too. Suggestion-enema first. You’ll feel clean, and so will he.

  78. Oh-suggestion, girls. Use silicone lube (silk,etc.,check Ebay). Doesn’t dry as fast, and is very slippery. Not as good for “front ” work-higher risk of reactions, but works great around back.

  79. hi there 3 years ago i had my dawter and suffer from hemroids, im scared to even check to see if they are still there, but my partner is pressuirng me to do anal or he will leave.( bludy egg, like i care.)hahaha, weve been together for 5 years now, wat should i do? does it affect my ass hole,lol many thanks.

  80. I would think that if you still had hemorrhoids that you would know it. If you follow the ten steps, everything should go well.

  81. Iately I been stickng finger in my butt and all the sudden it itches and burning I didn’t use lube now it seems like my skin is solen should I go to Doc or what to do? Any help wodul great…thanx….

  82. The first thing to do is to quit sticking your finger in your butt without lube. If the problem doesn’t clear up, then see a doctor.

  83. Thanx Svetlana:)

  84. if you have hemorrhoids you should never have anal sex is it right?

  85. I wouldn’t think so, but I’ve never tried it. Hemorrhoids can be cured, I think.

  86. One of the foreplay techniques I’ve used with great success is spanking. She gets on her knees aside of me and leans over to take me in her mouth. This gives me full access to her beautiful ass. I start off with nice and gentle caresses that build up slowly to “love taps” and then more firm swats, all the while she keeps pleasuring me with her mouth. Every moan and groan feels great ;-)
    Then we progress to intercourse. Eventually doggie style where I keep up the spanking and by this time she wants nice firm swats alternating with furious pumping. All of this has set the stage for me effortlessly sliding into her ass.
    As you can see this works on several different levels; the spanking releases dopamine that both gives her pleasure, relaxes her and raises her pain threshold. The whole scene is very sexual; she always dresses in hot lingerie and high heels to enhance her feeling of sexuality, and there is the sense of the forbidden, both because of her wearing a sexy outfit, spanking and anal sex.

  87. I like this, too, but recommending mild BDSM to a beginning anal sex post might be confusing. Good technique for the experienced though.

  88. Maybe, but I’ve also used this trick on my new gf, and she had never tried either spanking or anal before and now she’s hooked ;-)

    But I did introduce the spanking several months before we added anal sex, so you are right that it could be confusing if they both were new to her and introduced at the same time.

  89. That’s what I meant. BTW, I haven’t updated this blog in over two years. I moved it to its own domain in July 2009: http://sexsecretsblog.com.

  90. can we have an anal sex and vaginal sex at the same time. Are there any chances of infection???

  91. You can have anal sex after vaginal sex, but not the other way around. Yes, infection is a possibility.

  92. Me and my boyfriend have tried anal sex a couple of times, but i always hurts so bad. He has a big penis and he lubes it up well, I feel relaxed until it starts to hurt when he puts the head in. I dont know what to do! I feel like I’m not meeting his sexual needs We have tried the fingers in the butt, but with just one, it feels so uncomfortable and makes me feel like I have to poop. HEEEELLLLLPPPPPPP!!!!!!!

  93. Try using a butt plug to prepare for anal sex. Put it in at least a half hour before and take it out (of course) before your boyfriend starts to put his penis in. He still should use lubricant and start slowly, but that should get you ready for him.

  94. Hi,
    I have read your post and the comments thoroughly.
    My boyfriend keeps pushing and pushing the subject of anal and I do want to try it but quite honestly, I’m simply scared. I want to do this for him but my fear of my unbearable hurting afterwards has me avoiding the situation altogether.
    Are there any tips you can give me?
    I know what you’ve said on relaxing and what not but I haven’t been able to over come this fear yet.
    Please help!

  95. If you have read this article and the comments, you have all the information you need to prevent pain during anal sex. Try using a butt plug prior to anal sex, along with the other recommendations. It will make a big difference and prove to you that anal penetration isn’t necessarily painful.

  96. Hi my wife and I have been tryin anal sex for a while but cannot seem to get any where we’ve done and tryed everything possible from the tips you have to more but still she feels a bit of pain when I insert the tip of my penis in what can I do so there’s no pain for her the next time we try.

  97. can u die if the pain hurts to much?

  98. It won’t hurt much if at all if you follow the ten steps..

  99. You don’t say that you have followed the ten steps. If you haven’t, you should. They work. Your wife can also try inserting a butt plug prior to having anal sex to open her up. (See my post How to Have Anal Sex with a Big Penis.) You can also try The Teasing Penetration Anal Sex Technique. The key for pain-free anal sex is preparation. Just turning her over and sticking it in doesn’t work very well.

  100. Thank you so much for this! My fiance and I first tried anal about four years ago without lube or anything. Neither of us had any real knowledge of it and needless to say it was not a pleasant experience on my part. Recently he’s been wanting to try it again and, although I suspect I would enjoy it, I haven’t been able to dig up the courage to try again. Reading this gives me hope!

  101. oh i tried this once, its very painful. my husband is always playing rough and hates foreplay :(
    i never enjoy having sex with him, never get climax. when i had sex with another man who loves foreplay, it felt so good.

    well i only had anal sex once and it hurts me everytime i poo for the next 2 months. and my ass is bleeding a bit much

  102. Sorry to hear that. It doesn’t have to be that way, though.

  103. hi my gf and i tried anal sex for the fist time and i cannt insert my penis fully…at first we didn’t use lube and condom..and also dnt knw which position give more comfort..i am happy to read your tricks nd suggctn..can u sugeest a possition to insert easly..??we both 19 years old..

  104. hi since my last comment my wife and i have tryed the 10 steps and even brought but plugs but still she finds it a bit pain full to take my penis as she thinks its to big n thick what else can we try to make it less painful and could we shag while we both have butt plugs in us

  105. Hey, ok so my boyfriend has been nagging me about anal for a really long time. We have been dating for a few years now and we are both 17. I am scared about trying it but i really want to do it for him. The problem is i don’t have access to proper lube since the only time i go to the shops is with my family. Is there anything else we can use?? Is there also any suggestions of a particular favourite possition? Thanx

  106. The beginner position I suggest in the article is with the woman on her back and the man on top. The anus is more open and relaxed in this than in any other position.

  107. If she had a butt plug about the diameter of your penis and left it in a half-hour or more to open herself up, and the you used plenty of lube when you inserted your penis, how could it still hurt? Of course, she’s will still feel friction and pressure. That’s stimulation, not pain.

    If you’re not already using the position, I recommend with her on her back (most readers seem to ignore me about this), try that.

    Yes, you can have vaginal sex while wearing butt plugs.

  108. Petroleum jelly ad Crisco vegetable shortening are two old-timey anal lubricants. Start with the beginner sex position I recommend in the article – woman on back.

  109. today my bf tried to do 1st tym anal sex bt penis nt go inside nd i hurt a lot even there is bleeding too inside my anal

  110. Anal sex shouldn’t hurt. Be sure to follow the ten steps. Better luck next time.

  111. thanx for ur advice… i ll follow ur ten steps… this will be m first time having anal sex with m gf… if she starts bleeding then what to do… we both have talked about having anal sex and she is ready for it bt i am worried if she starts bleeding den what to do… cn u advice me…

  112. we both are 18yrs old so it make me worried more… plzzz help me…

  113. If she starts bleeding, stop. However, if you follow the ten steps, and go SLOWLY, chances are that she won’t. Make sure that she is highly aroused and, preferably, had an orgasm before you try penetration with your penis. Relaxation on her part is important. Also, remember that you don’t have to achieve penetration with your penis the very first time you try anal sex. Anal play – fingering, rimming, toys – is fun, too.

  114. thanks :)

  115. I read somewhere that you could use a syringe to apply the lube into the anus. Is this safe? And if so does it help alot?

  116. I wan to try it for the first time do you have any tips on how to relax?

  117. Trying to tell yourself to relax doesn’t work for many people if they’re untrained in relaxation techniques. Instead, have lots of foreplay beforehand to help you become sexually aroused and relaxed. Orgasm is an especially good relaxer :).

  118. It’s probably okay, but it’s not very sexy. Use a finger or two instead.

  119. what if i ejaculate inside the anus? will it lead to pregnancy?

  120. have you ever had it? wanna know your personal experience..if you dont mind….

  121. No.

  122. Read my post Anal Sex from a Female Perspective.

  123. Hello. I have always wanted to try anal sex, but have a few concerns I wonder if you could give me advice on. First, after having a child I have a mild rectocele. Will this make anal sex dangerous? Second, I’m worried about feces during. Will an enema solve this? Are there any other options? Do men care?
    Thank you.

  124. Only a doctor can answer your question, but it doesn’t sound good.

  125. Ok this is embarrassing bit me and my girl just started doing anal and the other nigh I stuck a finger in and felt something. I swear it was poo . Is this possible?

  126. Not likely, though possible, I guess.

  127. After anal sex 4 a long tyme abt 3yr it seems her hole not return to the normal what should we do

  128. See a doctor.

  129. my wife feels pain, what i do

  130. Make sure you’re following the ten steps and go slow-ly.

  131. I tried to have anal with my wife cuz she wanted to try, so I inserted my fingers while she was on top of me, i did it really slow, bu once my finger was inside she just froze and said her body weird, so I bought one of those butt plug and she tried on her own and said it hurt, so we tried together i ate pussy lubricated the butt plug and it went all the way and she said it doent hurt while in but if she try to pull it out and push it in thats when it hurt, my penis is bigger than the butt plug so i dont want try cuz it will hurt more.

  132. i wanna try anal but my gf is aware of it how do i tell her that its not hurt

  133. pleasr help me Svetlana

  134. Show her this article.

  135. I tried to have anal with my wife cuz she wanted to try, so I inserted my fingers while she was on top of me, i did it really slow, bu once my finger was inside she just froze and said her body weird, so I bought one of those butt plug and she tried on her own and said it hurt, so we tried together i ate pussy lubricated the butt plug and it went all the way and she said it doent hurt while in but if she try to pull it out and push it in thats when it hurt, my penis is bigger than the butt plug so i dont want try cuz it will hurt more, can you please tell what could i do?maybe some women dont enjoy anal?

  136. It sounds as if you did everything right. There’s a difference between feeling a little weird or uncomfortable and actually hurting, but if your wife says it hurt, I guess it did. She hasn’t really tried anal, so she doesn’t know if she likes it or not. Try again and see what happens.

  137. is there any alternative for lube ??? its not available where i live..any home material i can use ??

  138. Petroleum jelly works except not with condoms. I’ve heard that people used to use Crisco vegetable shortening for anal lube.

  139. I’m pregnant and have had a crazy increase in sexual arousal without any form of foreplay. I just wet n want to have sex. But my question is since this increase of sexuality, I’ve watched a lot of porn and wanted to know how safe it is for anal sex while pregnant and which positions work best for pregnant women?

  140. Anal sex is pretty safe. I think lying on your side would be most comfortable, but you would know best.

  141. it was really helpful. my girlfriend really enjoyed it

  142. my girlfriend enjeyed anal sex too. It was a great feeling. we did it the first time. I did slow and steady. keeping my girlfriend relaxed. I lv her very much. she looked into my eyes and I looked into her eyes. It was amazing. when I inserted my penis in her vagina she was in a lot of pain. So I did it slowly. Now we are married and have two children.

  143. is it too dangerous if we didn’t use a condom?

  144. My boyfriend and I have tried it but it was Extremely painful. Hes pretty large and is completely obsessed with anal. I am used to the butt plug but his cock is different. He keeps pushing me to do it and I don’t know what to do. What is the least painful position?

  145. As I said, on your back. Be sure that you’re following the ten steps. Anal sex should not be painful.

  146. If you have an STD, it is.

  147. Okay , you said the size won’t matter that much.But I have an anal toy…small and thin..which goes in with no problem.
    Having anal sex is a first for us both…so we want to know what to do so it won’t hurt….he is very big…9 inches and also very thick…and that scares the hell out of me.

  148. Be sure to follow the ten steps, and you might try the tips in my article How to Have Anal Sex with a Big Penis.

  149. My boyfriend really wants to try anal with me but I’m really nervous. The pain isnt so much what I’m worried about. I had heard in passing that sometimes a woman may defecate post-anal sex. Is this really the case? I’m hesitant because I dont think I’d be able to deal with that kind of embarrassment.

  150. If you have a bowel movement or take an enema beforehand, you won’t have anything to worry about.

  151. Hi me and my partner have indulged in a practice of anal sex but we may have don’t it a little wrong ,, we were at the point of penetration but it was hurting her and she asked me to stop so I did and now she feels like she’s a failure and she was noticeably disappointed ,,,, however we have talked about it in a serious and a joking manner and now after reading your tips and buying lots of lube were gonna both hopefully enjoy the pleasures of this extremely sexy way of making love ,,,,, thanks for the tips ,,,, chris and karen x

  152. Sorry I forgot to tick the box x

  153. Have fun!

  154. i would love to try anal sex with my boyfriend , but so terrified that it will hurt even if i go by the 10 steps . i just feel like with his big penis and my tight anus , it will not work.

  155. First time anal sex with my wife last night, she had always been against it. She had suggested it and following the 10 steps worked perfectly. She orgasmed within minutes and described it as mindblowing – can’t wait for the next time, or the time after, or the ……………..so on and so on.

  156. Great to hear. I hope you enjoyed it too :).

  157. My boyfriend expressed a desire to have anal sex awhile ago. At first, I was completely against it as I thought it was ‘dirty’. He accepted that and because he was so accepting I started thinking about it. I’ve done a lot of research online etc and I think I’m ready to try, but I’m not sure he is. I’ve mentioned it to him and I think he wants to do it, but I don’t think he knows enough about it to do it it without hurting me- which makes me nervous. He’s not the sort of man that talks much so communication is difficult. How can I get him to look at sites and information like this without pressuring him? I’m always the one pressuring him to have sex with me and I really want to have a positive first time. But how can I have that when it took over a year of me pressuring him before we went to a sex store?

  158. Hmmm. You can take charge yourself to some extent. Have lube handy and wait for a time when you are really ready. Lube yourself and him up and tell him you want it in your ass. Tell him to put it in you slow so you can enjoy it. Do things in your own style, of course, but it would be hard for most men to resist when their woman is begging him to take her ass.

  159. i tried analsex some time my wife enjoyed butt she do not give me permitton to do regular help me

  160. I’m not quite sure what you mean. What is “regular?”

  161. good advice i am goint to man to man anal sex for the frist looking forward to it

  162. My ex-boyfriend and I tried anal sex many times and it hurt everytime but once he was in all the way it felt better now Im with someone else and his penis is thicker than my ex we are about to try anal will it still hurt even though I have done it before?

  163. Follow the ten step, and you should not feel any pain.

  164. Hi my husband has been pressuring me for sometime for anal and i have been to scared to try it. We had a incident before where things got to wet and he accidently went there with the tip and hurt like hell and i wanted to cry so that didnt help.. Also right now since he has been pressuring more i am currently pregnant at almost 8 months and am wondering if that could play a factor into it being more painful or if it shouldnt matter i told him i think it something we should prob wait to try til after baby is born and i am fully healed and adjusted to normal sex again..

  165. Anal sex as an alternative to vaginal sex during pregnancy is an old tradition. It seems like you’re looking for reasons not to have anal sex. If you don’t want to try it, don’t. You don’t need excuses.

  166. Hi there thank you so much for this! My husband and I are about to try anal the right way for the first time !! I’m super excited and he couldn’t be more happier that I finally said yes to it. Thanks again!

  167. Have fun!

  168. This article is very helpful ima try it tomorrow

  169. I was stoked he other night, my wife knows ive wanted to try anal for ages she always said no no no never. but halfway through intercourse she said can you fuck me in the ass. I raced off and got the lube. I only got the head of my cock in before she said it was to painful but after reading this she said she will give it a go. I cant believe how good her ass felt when I was fingering it it will be awesome when I put my whole cock inside her I will keep you updated on how she liked it.

  170. Just remember to go slow, and it will feel good to you and her.

  171. My boyfriend really wants to try anal, but I’m not completely comfortable with it. :/
    I’m not exactly the smallest gal ever, considering I’m like 2″ taller than him and around 45-50 pounds heavier than him. I mean, we’ve tried doggie style and everything but the problem is me, he tries, but fails. This is kinda personal, lol. I have quite thick lips and I believe that is the main problem for him not being able to penetrate me properly. The only position that we can actually do is missionary. Any advice?

  172. Yes, do it missionary. It’s the best position for beginners especially because it naturally relaxes the anal muscles. Also, he can see your face and tell if he’s pushing in too fast or hard, and you can see him enjoying the tight feeling around his cock. Rear entry lets you both just focus on the physical sensations, but if you can’t do it, you can’t.

  173. My fiance and I have tried anal before and OMG it hurt so bad. Of course that was before reading this however, I do wonder if the product called Anal-Eaze is a bad idea and if it actually works. Can’t wait to find out and surprise him and do something new and interesting to spice up our love life.

  174. I don’t think using numbing products is a good idea. Pain is a signal that something is wrong, and you need to do stop and do something different. Anal sex done right should not hurt.

  175. Its always gud but I always feel pains aftrwards

  176. Does it matter if he’s really tall? My boyfriend is 6 foot 6, so positions where we “match up” comfortably are pretty much just doggy and cowgirl/reverse cowgirl. I’m 5 foot 2, by the way.

  177. Also, I’d like to add that I’m sorry for all the weird comments you’ve had to deal with from equally strange people.

  178. It doesn’t necessarily matter if he’s really tall, but you’re not, it sure does :).

  179. My boyfriend and I tried anal this weekend. We were spooning and started to have vaginal sex. He insisted on anal. Both our first time doing anal. Yeah it hurts at first but once it was fully inserted it felt AMAZING! I had sooo many orgasms. Im willing to try this all the time now

  180. Hello! My husband and I attempted to try anal for the first time but we were unsuccessful. He got his head in but even with the foreplay, lube and gentle stimulation the pain was ghastly! Is there any advice to help better my situation? I feel terrible because my husband is an “ass-man” and I’m intrigued by anal as well so I want us both to be pleasured… But the pain may be too intense for me to handle.

  181. Try opening yourself up prior to trying anal sex. Wear a butt plug for at least a half hour prior. If your husband has a big penis, work up to larger butt plugs.

  182. I’ve found this site and been curuious for a long time re anal sex. But – and this is so embarassing – I have a chronic anal fissure. It’s a tear in the passage and because its chornic it never goes away (they can operate but that makes it worse sometimes) so surgeon advised eating lots of soluble fibre and using a steroid cream if it flares up and bleeds – it bleeds A LOT when it flares up. I’d daren’t ask the doctor – do you know if it will ever be safe for me to try anal or will it always be a big risk. My other half is great and never pressures me but I nkow he’d love it.

  183. It sounds as if you should avoid anal sex.

  184. I have been wanting to try anal sex ever since I lost my virginity and I have tried to do it with several of my exs but no matter what lube or without it hurts really bad upto the point when I get watery eyes. I can’t even get the nob in. I’ve tried many possible positions aswell. I think it might be the tightness of my asshole but u said In most of ur replys that size doesn’t matter. even when I take a poo sometimes it hurts and in some occasions even just taking a poo I rip my anus. when I get aroused I get really really wet but all I want to do is just loosen it up a bit down there and yes I have been poking my butt hole, but noting seems to work at all I want to be able to try it with my next partner without looking like he hurt me really bad.

  185. i,d like try analsex,but there,s something in the rectum like hymen idont know what it,s ,,if i tried to push my penis deeply,,is it danger for her?..

  186. Rectums don’t have hymens.

  187. […] Advice 10 Steps to Great First-Time Anal Sex Catalina says Give Great […]

  188. I had a lot of pain after anal sex, and found that when I got on top I could control insertion and the penis “fit” better that way, also continual clitoral stimulation is the only I can stay loose enough.When we started I had ripped some, it was painful. However the on top position solved that, only problem with constant clitoral stimulation during anal sex is I come quickly. Once I do my anus snaps shut, play time over! But it is quite possibly the best sex ever!

  189. The on-top position can sometimes work really well, but for others, it creates muscular tension. You just have to experiment.

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