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.
If you want a complete guide to making anal sex the fun, pleasurable experience it should be, Arouse Her Anal Ecstasy focuses on how to introduce a woman to anal sexuality with a pleasurable and painless detailed step-by-step system. This book teaches exactly what to do and how to do it. You will give her incredible orgasms by stimulating multiple erogenous zones, and she will love it!
Tags: anal intercourse, Anal Sex, anal sex advice, anal sex for beginners, anal sex for the first time, anal sex positions, anal sex secrets, anal sex steps, anal sex tips, analingus, first anal sex, first-time anal sex, steps to anal sex
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. My sexual history and preferences are detailed in my post 
January 2nd, 2008 at 5:22 pm
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.
January 8th, 2008 at 7:04 am
Unless you are 100% sure of your partner’s STD and HIV status you might also consider using a condom.
January 8th, 2008 at 7:39 am
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.
January 20th, 2008 at 7:47 am
[...] 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. [...]
February 6th, 2008 at 6:27 am
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?…
February 6th, 2008 at 8:01 am
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.
April 7th, 2008 at 4:17 pm
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April 29th, 2008 at 2:20 pm
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…
April 29th, 2008 at 2:37 pm
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.
May 20th, 2008 at 11:25 pm
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.
May 21st, 2008 at 5:26 am
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.
May 22nd, 2008 at 8:12 am
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?
May 22nd, 2008 at 8:34 am
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.
May 23rd, 2008 at 1:01 pm
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May 29th, 2008 at 11:06 pm
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 :)
May 30th, 2008 at 7:55 am
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.
June 2nd, 2008 at 1:02 am
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June 13th, 2008 at 7:01 am
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June 15th, 2008 at 1:01 am
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June 20th, 2008 at 10:49 am
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!
June 20th, 2008 at 7:56 pm
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.
June 22nd, 2008 at 11:23 am
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…?
June 22nd, 2008 at 12:17 pm
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.
June 25th, 2008 at 6:44 am
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!
July 12th, 2008 at 1:01 pm
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July 13th, 2008 at 9:44 am
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
July 22nd, 2008 at 12:49 am
Are enemas required before anal sex?
July 22nd, 2008 at 5:39 am
“Are enemas required before anal sex?”
No.
September 11th, 2008 at 3:37 pm
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???
September 11th, 2008 at 6:27 pm
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!
September 12th, 2008 at 11:33 am
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.
September 12th, 2008 at 11:49 am
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 ???
September 12th, 2008 at 12:14 pm
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.
September 25th, 2008 at 1:01 am
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October 1st, 2008 at 5:23 pm
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
October 1st, 2008 at 6:45 pm
The only guaranteed way is to use a condom.
October 25th, 2008 at 1:01 am
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November 4th, 2008 at 5:59 pm
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!!!!!
November 4th, 2008 at 6:51 pm
Thanks for the feedback, Tiara. Anal sex is pleasurable for anyone – regardless of gender or sexual orientation – when it’s done right.
November 13th, 2008 at 6:54 am
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December 23rd, 2008 at 6:28 am
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June 29th, 2009 at 6:04 am
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July 1st, 2009 at 7:28 am
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July 1st, 2009 at 7:31 am
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July 5th, 2009 at 1:54 pm
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July 6th, 2009 at 7:29 am
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July 31st, 2009 at 6:08 pm
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August 1st, 2009 at 8:10 am
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August 29th, 2009 at 4:13 pm
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!!!
August 30th, 2009 at 12:16 pm
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.
May 13th, 2010 at 1:49 am
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!
June 10th, 2010 at 6:07 am
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July 1st, 2010 at 5:02 am
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February 19th, 2011 at 1:10 am
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.
February 21st, 2011 at 4:53 am
Anal is absolutely not for me; nor has any of my lovers ever suggested it. If they had I’d have declined. The idea is the biggest turn-off I can imagine.
March 7th, 2011 at 12:34 pm
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?
March 7th, 2011 at 6:51 pm
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.
May 4th, 2011 at 11:58 pm
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
July 16th, 2011 at 12:32 pm
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”…
December 12th, 2011 at 8:23 am
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
December 12th, 2011 at 11:01 am
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.
October 12th, 2012 at 10:44 am
when My wife was pregnant with my son..we had sex then anal sex….