How Do I Enjoy Anal Sex?

By Kendra Holliday | October 15, 2015

Sex Positive St Louis is giving a talk on Anal Sex for Women Sunday at Shameless Grounds! Here is a relevant post you can read beforehand!

Dear Kendra,

My guy is an ass man. Which is great because he loves my ass. What’s not so great is that he also loves to fuck my ass. I do not enjoy anal sex, but it’s something I would like to be able to do happily for him. We do it twice a year, but I know he’d like it more even if he isn’t actively asking for it more. The reason he isn’t actively asking is because he knows I don’t enjoy it, which is a turn off for him. There are two things I’d like your advice on.

First, I really want to be a good partner for him and give him great anal sex, but that seems to require that I enjoy it. Though I willingly give it, the act itself is so unpleasant for me that I tend to go silent during it, which is a big, obvious difference from my usually vocal self and a huge clue that I’m not enjoying myself the way he would like. Frankly, when I’m quiet I’m just trying to keep it together (“relax, relax, breath, don’t breath too fast, relax, relax, etc”). We’re trying some things to make it more enjoyable/tolerable for me: he always makes me cum first, I enjoy it when he rims me, pot (helped me with the last guy, haven’t tried it here yet), I’ve used a vibe during (did nothing to help), him using fingers first (almost as weird/uncomfortable feeling as the real thing), and yes we use tons of lube. But at the end of the day, do I just have to buck up and moan for him?

Second, he believes that everyone is equally capable of enjoying anal sex. Therefore, I should be able to enjoy it as much as all the porn stars do in all the anal porn he watches. I do not believe this is true at all, and when he says things like this I get the impression that he thinks I’m simply not trying hard enough to enjoy it; which is bullshit and makes me feel like he doesn’t appreciate the fact that anal sex is highly uncomfortable for me and I’m basically doing it just to be a good partner (it certainly doesn’t do anything for me). It’s like “Duh! Of course I would like to enjoy it, right now it sucks!” Who’s right, is anal sex for everybody or can it simply not be for somebody?

Anal sex is really his only non-vanilla desire when it comes to sex, and he’s been so good about accommodating my kinks/desires that I hate that I can’t seem to give him exactly what he wants in this one arena. This isn’t threatening our relationship at all, it’s just highly disappointing when it comes up. I know that anal is something you’ve “struggled” with as well, so I hoped you’d have some advice for me.

My reply:

My butt has seen better days.

My butt has seen better days.

Time for a confession: I’m in the same anal boat as you. The only difference is, my man could take or leave anal sex.

For some men and women, getting fucked in the ass is easy, but not for me! Even Tristan Taormino’s anal sex guide didn’t help me out much. I truly believe that due to unique physiology and/or mental state, some people are not equipped for easy anal play. That’s not to say it’s impossible, however. As Toni Bentley pointed out in her memoir The Surrender, “The ass does not lie.”

I REALLY wanted to be a three hole slut, so over the course of a decade, I went from trying and failing a few yucky times to doing it once in a blue moon (big ordeal but successful) to doing it every couple months or so. I FINALLY got used to the sensation of a dick sliding in my ass, even pounding it. It took persistence and practice. But to be honest, after I achieved that goal, I put it on the back burner since it’s not a big deal for me.

Is it worth all the effort? Well, I’ve had some of my most intense orgasms via anal sex, so I say YES.

My friend offers these tips:

* Of course, use lots of lube (experiment with brands and types, some are more anal friendly).
* Give lots of stimulation in the general area first. Don’t go straight for insertion. Move lubed fingers around, and press and stroke rather than poking or prodding.
* Go slooooowly.
* When the head of the penis is in, just wait. Move in a gently rocking motion, rather than thrusting or pushing. Have him push his penis down, i.e. towards your vagina, instead of up towards your tailbone. Have him move his penis side to side a little bit.
* When you want it further in, push out like you’re (and there really isn’t a nice way to talk about doing a poo) going for a large dump. This makes the muscles on all the overlapping sphincter muscles relax in unison (it’s when they don’t relax that it hurts). This is a secret trick!


* Don’t feel like you have to do it! Don’t do it because somebody else wants to fuck you in the ass and you’re half-hearted!
* Only do it because you WANT to – you like how it feels (or think you will) or you love the naughty idea of it (etc) and would like to try it out.

If you’d like to warm up with toys, I suggest the Flexi Felix anal bead toy or a Crystal Delight butt plug – they come in various sizes and gorgeous designs. Glass is very easy to clean. You can also put a condom on your butt toys.

I did a fun podcast on anal sex with Life on the Swingset that’s worth a listen.

As for hygiene, it’s nice to be assured that you have a clear passage. Sometimes I’ll give myself an enema beforehand using one of those cheap disposable ones from any drugstore, but I replace the fluid it comes with with lukewarm tap water. More often though, I’ll stick a soapy finger in my ass in the shower or bath to check things out. Throw a towel down on the bed if you’re worried about leaving a mark. Experiment with different positions – some will work better than others.

Don’t give up if it’s important to you. Your body changes, evolves, matures. You may well find out someday that you can have anal sex easier with a different partner.

Most importantly, pay attention to your mental state. Just an observation, but the women I know who are anal easy tend to be laid back, and the women who are anal shy tend to be high strung (me).

I harbor fear in my ass, and it causes my muscles to tense and my ass to clamp down. With coaching from my partner, I have learned to overcome the psychological hang ups I have about anal. With his loving support, I’ve learned to relax, breathe deeply, and be open to the sensations. Like a reverse birth coach!

Please share your best anal tips. What works for you?

BONUS LINK: Ten Rules of Anal Sex, by Jack Morin, Ph.D.


Stephen 2011-06-29 13:11:33

I loves me some anal, and here is where my size matters!

Being Jewish and all that comes along with it, my cock ain’t Beast-sized at all. Hell, I can do you in the ear without lube and you won’t feel it (but you’ll hear me coming) >rimshot< (rimshot for 'rimshot,' double entendre). Seriously, tho, my penis is fine, but not big, not girthy, and therefore is a wonderful anal sex starter kit for the shy sphincter. Anal sex, however, like first orgasms, is mostly mental first, physiological second. And like first female orgasms, concentrating on it, discussing it and persevorating about it will become huge obstacles to actually letting go and doing it. Pot/booze can certainly help, but you don't wanna over-do it. Also, being clean will help - not for the guy, who pretty much doesn't care (he knows the potential and knows where the soap is), but more for you. Like women who have Aunt Flo oral hang-ups it's all about you. If a guy knows Flo is in town and still heads south, he's fine with it. Mature guys who go for the pacific rimjob will sexily invite you to shower with him if he finds you're a bit rank from a night out dancing. Gay guys know to chickity check themselves with a secret swipe-n-sniff and a follow-up trip to the powder room prior to intercourse. But with anal, discussion prior (not JUST prior, but during dinner or days before) really helps. You can tell your man what hang-ups you have and you can prevent the 'whoops it slipped' moments us guys are always trying. But once the discussion is over, no need to discuss further. You can just tell him you'll try it when you're ready (we're ALWAYS ready). Then, some night when you're lubed and it's lubed and you're clean and your mind is dirty, you can back dat ass up. YOU control the penetration. We're gonna be so fricking happy we'll be fine with it. You back up as much as you can take, but know it's a cycle for you: pain, pleasure PLEASURE OMG!! then pain pain GETTHEFUCKOUT. You do not need to stay there in pain trying to relax and breathe while studboy is pounding away if you aren't enjoying it. We want you to stop at this time, unless it's a one-night stand, because we want you to love it so much that it becomes a lifelong thing, not a cause for contention. Finally, practice. Anal beads with him. Small dildo during masturbation for you. Butt plug is up to you, but only use it first time when you haven't just eaten or need to take a number 2 soon. The purpose is to feel full in a place you haven't before and to stimulate the gabillion nerve endings along the rim and taint. During porn you tend to see the girls rubbing away at their clit during anal, but I recommend putting a dildo in the vagina and moving that. That feeling you'll get of double-full and the feeling he'll get of pressure from all sides should quicken his cum-pace. Good luck. Personally I know anal ain't for everyone, just like great deep BJs aren't inherent in every woman. God Bless you for trying, tho. And if push comes to shove, so to speak, buy yourself a tiny little strap-on and reverse roles. Let him feel the sensation of pain/pleasure/getitout so he'll know better what to offer you. And if you really need help, call me. I'll ship myself and my little Jewish anal sex starter kit right to you - just pay shipping and 'handling.' Steph


    Kendra 2011-07-04 08:31:07

    Ha! Great suggestions, Stephen! I love a dick I can do everything with! I’d love to create a parody porn site with ads that trumpet, “Reduce your penis size!” “Make girls happy with your average size cock!”


Hypocrite 2011-06-29 14:21:06

Going slow and the “push out” have worked for me, both giving and receiving.

As for the whole “he believes that everyone is equally capable of enjoying anal sex” time for his ass to cash the check his mouth wrote. Get a toy that is approximately the same size of his cock. And say to him “OK Mr. Expert, you go first.”


    Kendra 2011-07-04 08:31:55

    THANK YOU for saying what I wanted to say. Bend over, boyfriend!


    Belladonna 2011-08-04 22:46:47

    hehe I knew there would be words re: anal equality lol

    He actually admitted to doing quite a bit of self service anal penetration when he was younger, but he says he’s not interested now. There’s always the future though, I’d love to peg ;o)


Delia Dawns 2011-06-30 00:50:18

Kendra ~ Your advice is right on!

Experimenting with lube is essential – I like the Pur brand line, Uberlube, or Liquid Silk.

And Crystal Delights! I love my plug. Glass is the way to go for anal I think, no worries about using silicone lube with silicone toys, and it is still non-porous and fun for everyone! (and their toys are so gorgeous!!!)

I would also say that I recently gave myself an enema (warm water and a store bought Fleet bottle) and it was surprisingly NOT uncomfortable or gross, and gave me the extra assurance that everything was clean as a whistle – which in turn made me way more relaxed and able to enjoy everything.

But all in all, anal just is not for all people. Me? I cannot fathom having my toes sucked, but some people love it. Not loving anal does not make you any less an incredible lover.


    Kendra 2011-07-04 08:34:02

    An enema can be nice! And for sure everyone is different and has their preferences.


Kitty Calhoun 2011-06-30 02:07:27

I think this is on the horizon for me. Gulp.
My partners will appreciate your advice as much as I do.
Thanks for always knowing just what to say!


    Kendra 2011-07-04 08:34:40

    Can’t wait to discuss more in person later this month! Chicago, here we come!


dannyg 2011-06-30 20:57:42

I and my girlfriend enjoy anal sex, but we don’t do it all the time; typically once-a-month. A few weeks back we were sitting on the back patio grilling, drinking sangria, and talking about sexual chemistry. The conversation turned to anal sex (not surprisingly because we did it just that morning) and she asked me “what is so appealing about anal sex.”

My response isn’t important, but you may want to pose that question to your boyfriend and get his feedback. If it’s because of the anal-sex porn he watches you may want to ask yourself ‘what else is he into, what other fetishes will he ask of me.’

Please do not misconstrue my previous statement. I think that couples need to experiment in and out of the bedroom to keep it interesting, exciting, and fun. But like Delia wrote “anal is just not for all people.”


    Stephen 2011-07-02 09:38:05

    I have been asked that before – ‘what’s so appealing to you about anal sex?’ and I haven’t been able to answer.

    I should have approached this question when I was still in therapy, because I’m still not sure what the answer is…I don’t know if it’s cuz it’s taboo, or if there’s an ever-so-slight rape connotation there, or gay fantasy somehow, or what. I just know I really love it, and I just know it has very little to do with the actual feeling of it…it’s all mental for me.

    It has an excitement to it, a sortof ‘taking of virginity’ excitement. That first push in is the best part, then it’s the whole ‘omg, she’s letting me do her ass!’ followed by ‘OMG, she’s actually loving this!’

    As you can tell, tho, I can’t really as a male spell it out. But I would LOVE to hear what some (all) of you have to say about why you love anal, if you’re one of those that do.


      The Bees Knees 2011-07-07 15:38:53

      Things I like about anal sex.

      Really if you can relax and just enjoy the physical sensations it just feels sooooooo freaking good.

      Getting to that point of just being able to relax is a huge turn on for me. To me it means I am with someone I trust. I trust them to not freak out if there is a mess. I trust them physically not to cause me harm since anal cavities are more fragile than others if you don’t approach it with love and sensitivity. Trusting your partner enough to cross boundaries with them is hot.

      And I love giving up that control. I’m a very private pooper. The thought of someone I am intimate with (strangers I don’t care)hearing me poop or gawd forbid if my shit stinks… it’s almost enough to cause an anxiety attack or for me not to poop for days if I don’t have the privacy I need… so during anal you’re always taking that chance. Messes happen, smells happen… you can’t be in control 100% so giving that up for me is a very erotic part of the whole anal sex process.

      And last who doesn’t enjoy being a filthy slut? πŸ˜‰

      For me when those factors are in place it’s very easy for me to open up physicaally for typical anal sex. I often do not use any lube or have to make an ordeal of going slow because I am just that relaxed and turned on.


    Belladonna 2011-08-04 22:49:01

    I have asked, and his reply has always been the taboo aspect and the simple variety of a different set of sensations.


EvanderS 2011-07-01 15:15:01

Anal muscles are mostly unconscious muscles… we haven’t learned how to use them. For most of us… they only relax (briefly) while we are on the toilet. Tristan did an awesome workshop where I learned how to receive anal… and here is the advice in a nutshell.

1) Use toys first
a) use only toys that feel good (I agree about the glass and greasy lube)
b) mix in sexual stuff that you like while (like receiving oral)
c) You may have to take the toy out from time to time to take a break. Work towards keeping it in for longer and longer periods of time.
d) When you are comfortable with a toy… move up in size. This may take weeks or months. Enjoy the journey.
e) after a while you will have a collection of toys sized from small to large (about the width of your partners penis… maybe bigger) Use them to gradually warm up going from small to big.
f) Resist fucking movements that will increase friction. Save your ass for your partner… no need to get raw before the action happens.
e) I’d resist the temptation to use alcohol or drugs as these can create states of openness that you will regret later…

That’s it. Like an Olympian you have to practice, practice, practice. Start small and gently expand your limits. In the end you’ll be glad that you did because you will have given your boyfriend a gift, he’ll want you more, and you will have overcome something that you were scared of… giving you more confidence.

Good luck!


    Kendra 2011-07-04 08:40:25

    Great summary! Yes, accomplishing anal sex can be empowering! It is very therapeutic for me, allows me to tap into deep emotions and I often have a cathartic cry, so intense and primal.


Buddha 2011-07-01 16:05:16

I just do whatever the doctor tells me. Sometimes he’s gentle. Sometimes not so much. It would help if he engaged me in a little conversation first… maybe asked me about my favorite movie. Oh, you’re talking ANAL anal… as in S-E-X. Huh. Tell him to go slow, work up to it, and whisper, “My cock in your ass reminds me that we need to fly TBK out here, book a room at the Surf & Sand in Laguna Beach, rub Nuru gel all over each other, and fuck out on the balcony while watching the waves crash against the shore.” I think it might help. I do. Really.


    Kendra 2011-07-04 08:41:29

    Did someone say Nuru gel? πŸ™‚


The Nerd 2011-07-02 13:58:43

Not that I think anyone’s stupid, but it bears reminding: anything that has been in the anus MUST be washed before exploring the vagina!

I have a question: does anyone have any experience with using a “female” condom in the anus to reduce friction?


    Kendra 2011-07-04 08:42:52

    Good reminder. Interesting question about female condom for anal sex! I’ve only used a female condom a couple times vaginally and found it awkward. Trying to imagine stuffing a plastic baggy up the poopchute…


Belladonna 2011-08-04 22:57:23

Update from the letter writer!

A few days ago I experienced awesomely successful anal sex! Woo! I’m still pumped about it. I feel like a winner lol

Thank you all for your suggestions! I basically surprised him the other night by initiating it myself without any pre-talking it out. I think taking control was a big factor, and also just going for it without any “dramatic” anxiety increasing hashing it out beforehand. I just went for it with no expectations or obligations. We used a different lube and I spent a long time just “massaging” my anus by pressing on the head of his cock. We were also going at it from a completely new position. The pushing out really worked! Also, and this surprised me, having him put his fingers inside my vagina while we were doing it was great! Now I’m a DP slut! πŸ˜€

We hadn’t done anything with toys yet, but now I’m excited about going there too!

Happy endings for all involved, yay! :heart:


The Nerd 2011-10-01 20:55:39

OK, I am so so so surprised I haven’t read this anywhere, especially here:


My boyfriend has tried putting various objects into my ass, even his tiniest finger, and it always irritates the shit out of me (er, wrong choice of words, hehe)! Then one day, he placed the Hitachi up against a dildo which was in my vagina, and I had to ask “is something in my ass?” No, there wasn’t, but the vibrations made it feel like something was stimulating it from within. “Go ahead, stick a finger in.” I couldn’t feel it – no irritation whatsoever. I was amazed.

Fast-forward to today. I have a couple blue extenders that pop on top of the Hitachi, with a dildo on the side (one straight, one curved). We put the straight one on, lubed up my asshole and I told him to rest it gently and then slowly apply pressure at my command. “Maybe try pressing it in now.” “I can’t – it’s already all the way inside you.” “WHAT?”

Now, I suppose for some people, “feeling it” is kinda the point. But for me, it was amazing. It was as enjoyable as feeling vibrations on the outside, plus I felt like I had accomplished something huge!

I hope you’ll spread the word to others out there who, like me, are terrified of anal play and who have only had bad experiences in the past. Perhaps this will be the trick which turns on the fun.


Michael 2011-10-10 17:05:12

For me, there are two big aspects to “why anal?” First is that it’s generally tighter, so there’s a different, somewhat increased physical sensation.

The second is that when I’m fucking a woman’s ass I feel like I _own_ her. Don’t get me wrong, I don’t want to control her life outside of bed (or even in it, most of the time). But there is that little impulse, usually counterbalanced, that just out then.


Mona 2014-09-15 16:13:18

I love it, but not with everyone.

A guy has to be a very sensitive lover and be able to go very, very slowly and stop the moment you say, “Stop.” He has to be in full control of himself.

I don’t care for rocking. I like a slow, firm, steady push, then stop when you hit the sphincter & let me relax. I don’t care for side to side movement, either. Just lots of foreplay, lots of lube, and very, very slow entry. When all the way in, stop and let me relax. Then slowly pull back just a little, and slowly back in, initiating the back and forth movement very slowly at first. Little by little, increase it.

Done poorly, it hurts like hell. Done well, it would make an atheist see God.

It is absolutely the most relaxing thing I’ve experienced. I think it’s because that internal sphincter is not a voluntarily controlled muscle. You have to be able to relax at a very deep level for it to open up. You really have to trust your top.

Size matters. Too thickly built and it just isn’t comfortable.

I love it. My biggest problem is finding good anal lovers. They are hard to find.


    Kendra Holliday 2014-09-15 16:15:00

    GREAT COMMENTS! I agree!!!


stephen 2015-10-17 19:37:06

i used to think I was open to anything, but I confess, anal penetration does nothing for me and yet, I love analingus. All the pleasure without the pain.
I guess we’re all different.


AlanK 2015-10-20 08:16:09

The wide variety of responses and the sheer number of responses suggests this is a topic that you might fruitfully write more about.


    Kendra Holliday 2015-10-20 17:19:11

    omg the anal sex talk was AMAZING! You always hear about the pain, but you don’t hear about the out of body experiences, spiritual awakenings, deep orgasms… some people had tears in their eyes listening to the powerful stories shared, as well as good tips!


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