About Me
I came to the U.S. at age of 12 with my mother. We settled in sunny Florida, which was quite a contrast to Minsk. I have always been fascinated by sex and relationships. Sex Secrets is where I share sex advice, experiences, news, and sometimes a little humor. If you have a question about sex that you prefer not to post in the comments, you can email me at svetlanaivano(at)yahoo.com.
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10 Steps to Great First-Time Anal Sex

bed-coupleMany 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.

49 Responses to 10 Steps to Great First-Time Anal Sex

  • James says:

    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.

  • Ell says:

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

  • Svetlana Ivanova says:

    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.

  • kindra says:

    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?…

  • Svetlana Ivanova says:

    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.

  • Gretchen says:

    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…

  • Svetlana Ivanova says:

    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.

  • yalanda smith says:

    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.

  • Svetlana Ivanova says:

    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.

  • SALLY says:

    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?

  • Svetlana Ivanova says:

    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.

  • renee says:

    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 :)

  • Svetlana Ivanova says:

    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.

  • fanseet says:

    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!

  • Svetlana Ivanova says:

    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.

  • Mimi says:

    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…?

  • Svetlana Ivanova says:

    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.

  • lilmissy says:

    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!

  • KAtie says:

    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

  • Steve says:

    Are enemas required before anal sex?

  • Svetlana Ivanova says:

    “Are enemas required before anal sex?”


  • Amy says:

    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???

  • Svetlana Ivanova says:

    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!

  • AMY says:

    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.

  • AMY says:

    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 ???

  • Svetlana Ivanova says:

    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.

  • Lindsey says:

    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

  • Svetlana Ivanova says:

    The only guaranteed way is to use a condom.

  • tiara says:

    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!!!!!

  • Svetlana Ivanova says:

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

  • sadia says:

    name sadia
    quallification bsc
    city multan
    age 21
    searching sincear friend
    if you like then message me at this number
    at this time no is off i wil on after 12am
    number 0 3 4 4 6 4 3 7 2 5 3
    please dont send me poetry

  • is says:

    I reallllly want to do full anal sex with my partner – I can’t tell you how much. I have had three ops for heamarrhoids and my ass is now in the right condition – physically and mentally – for me to want to do it. I can take a finger or a small finger size dildo and I now have a butt plug but i can only take some of it. I can deal with a finger and a tapered end dildo but anything wider then a couple of centimetres, my ass just willl NOT relax and open. I am very frustrated but dont’ want to use poppers as I have arrythmia and don’;t think it woudl be sensible but judt cant get my anus to relax. Even if I fuck myself with the butt plug it won’t open up to take the full width. a ‘bluntv ended’ cock has no chance. Heeeeelllp!!!

  • Svetlana Ivanova says:

    First of all, make sure you’re using plenty of lube. You can’t use too much. Here are a few things to try.:

    1) Breathe slowly and deeply during penetration. Take 5 seconds to inhale and 5 seconds to exhale, and be sure that your stomach is relaxed. Deep breathing has to relax you.

    3) Many people find that pushing their anal muscles out as if having a bowel movement makes penetration easier. As you push your anal muscles out slightly, push the object in.

    3) During penetration, try clenching your anal muscles around the object. Hold for as long as you can, and then release. Again, tensing and releasing has to relax the muscles. Each time you relax, push the object in a little deeper. Maintain your deep, slow breathing. I would push the object in on the exhale, but you may want to experiment with that.

    Good luck! Be assured, the effort is worth it.

  • I truly enjoyed reading your blog. It was well written and simple to undertand. Unlike additional blogs I have read. I also found it very interesting. Actually after reading, I had to go show the spouse and she ejoyed it as well!

  • Lailah says:

    Hi, thanks so much for the post, I have tried anal sex and did not enjoy it, however I very interested in finding the pleasure in anal sex. My biggest issue has been, that “pooping” feeling.Noth sure if you or anyone here knows what I mean, but if feels like I’m taking a poop when the penis is inside during thrusting making anal sex uncomfortable. I’m not sure how to avoid it, maybe I need to be more relaxed or maybe its the trusting shouldn’t be long, maybe deep and soft, not sure…any advice? Have u encountered this issue? If so how have you overcome? Look forward to hearing from you soon.

  • Prettygal9 says:

    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?

  • Svetlana Ivanova says:

    If you’re able to have vaginal sex, anal sex should be all right. Try the spoon/side anal position, which should be comfortable for you.

  • Lailah says:

    ok, I guess no1 has experience what I’m talking about, I was hoping to get some advice but maybe it has to do with positioning

  • Lucky or Not says:

    An advantage of beeing under-endowed is that I never had to go through such a steeple chase … On the contrary it was always my partners who have straightforwardly directed me to that entry ….
    When I was still inexperienced I even embarassed myself in 2 occasions by not noticing the change of orifice (as it was happening in the dark and they were handling the thing) and thus disappointing the ladies when they later asked if I enjoyed it by not knowing what they were talking about …
    So I hope that this contribution will help breaking such stereotypes as : “Big ones are and have all the fun” as well as : “you have to beg women for anal sex”…

  • billy oarker says:

    My penis is a little over 11 inches long. How much penis is safe to push into imy gfs rectum, and is it normal
    for my gf too shit right after I pull my penis from her butthole

  • Svetlana Ivanova says:

    You can find out by SLOWLY pushing in until you feel resistance, or it hurts her. Then stop. That’s how much. Your girlfriend may want to try an enema before anal sex. It’s usually not necessary, but sometimes it’s a good idea.

  • danny says:

    when My wife was pregnant with my son..we had sex then anal sex….

  • Laura says:

    If you have hemorrhoids, how can you go about anal without them flairing?

  • Svetlana Ivanova says:

    Don’t have anal sex with hemorrhoids. cure the hemorrhoids first.

  • Abby says:

    Hi, i haf anal dex for the first time with my BF then had vaginal. Is there a risk of getting and STD even though we are a monagomous couple!
    It was a rookie mistake!

  • Svetlana Ivanova says:

    Not STD so much as just disease in general because the vagina is a good incubator for bacteria. Don’t do it again without washing thoroughly between.

  • Jack says:

    “Not STD so much as just disease in general because the vagina is a good incubator for bacteria. Don’t do it again without washing thoroughly between.”

    If you follow Step 1 in the article, it should be clean enough for Step 2, right? So if its clean enough to push the tongue in as far as you can, there shouldn’t be any need to wash the area after anal sex and before vaginal sex. After all, oral hygiene is just as important vaginal hygiene. But if, as you suggest, there’s a danger that the vagina can harbour bacteriar carried over from the anus, does that mean we can expect bacteria in the mouth too?


    i love it in my arse..frankie doyley and loads of men shag my arse


    frankie my lover fucks my arse so hard i squirt

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