Adventures in Anal (A beginner’s guide)

So did you know that August is anal sex month? Well, now you do! You’re welcome. I have no idea who comes up with these national months although in this case, my guess is someone who really likes anal…

I had a fun slumber party last weekend for my old college roomie’s bachelorette party. I miss a good old fashion slumber party. You know, the kind where you get in your jammies and roll around in glitter. All of the best conversations are to be had between 11 pm and 2 am, and since we’re now “adults,” we miss out on some prime conversations by not piling into bed with each other. What? You have a husband to go home to? Don’t care. It’s time to mute the TV and stare at Ryan Gosling while we tell the story about the time you hooked up with a guy wearing a dress in a Campus Cleaners van.

This past weekend, I got to give a midnight mini infomercial on anal sex. I’ve been meaning to do a quick “intro to anal” thing for a while, and Emily over at XOJane did a really great one in the beginning of the month. To read her full article, head over to XoJane. But before you do, I shall give you a few more! Because you can never have too much advice about anal sex. Note that because I’m a female currently in a hetero relationship, most–but not all–of my suggestions are coming from that angle, but they should still be helpful for everyone!

Get over the mental block
Let me start by saying I used to be really anti-anal. I was of the “exit only” party. But your butt is actually a really awesome (and underrated) pleasure point… You can thank your prostate for that. Anal sex is not “gross.” Poop is gross, but as you read on you will see that for the most part, anal sex doesn’t involve any poop. You’ve been misinformed. But the biggest mental block for women, I think, is the pain factor. My whole no anal campaign was based around the idea that I refused to do it unless it felt good. But I did a little research (my Google history is prime), and then I did a few studies in the field. So if you’re not into anal, man or woman, read the following and think about maybe, maybe changing your mind.

That “no pain, no gain” thing was NOT written about anal sex. Anal sex should never hurt. One bad experience with spit-for-lube and you’re scarred for life. Don’t do the whole “I’ll just get so drunk I can’t feel it,” thing. A lot of my friends say they tried it that way, and none of them had happy stories about the experience…You should never have sex when you “can’t feel.” Sex should feel good, and if it hurts, it should be the “hurt so good” type of pain. Like when you eat too much wasabi and your nose is burning. Or like when you have anal sex.

That being said, it will probably be uncomfortable for the first few seconds, but if you relax, it shouldn’t hurt. I know, you’re thinking that having a dick in your butt is not your idea of relaxing. But just chill out, focus on your breathing. All that clenching will just keep it from being pleasurable, and that’s the whole point.

So what will it feel like? It will give you an interesting “full” sensation, and it will be satisfying in a totally different way than regular P in V. Like if you had a really bad itch you’ve been meaning to scratch, and you finally got it. Like that.

Size matters
Sorry but in this case, the size of the partner does matter. As XoJane’s Emily said, “As far as I’m concerned, you get to have a really big dick or you get to have anal sex, but not both. EVERYBODY CAN’T HAVE EVERYTHING.” Amen. Have anal sex with a guy on the “normal” side of the dick pool, or be prepared not to sit down for a week. And if you must do it with a bigger dude? You just HAVE to? Well then there are always…

Treat it like a lady
Because your asshole wants to me romanced just as much as any other orifice. In fact, it requires more attention, because unlike its buddy the vagina, it doesn’t self lubricate (read on for more lube info…). So don’t just go for the gold right away. Take it to dinner, buy it some flowers, diddle it a little bit–flattery goes a long way! No really, make sure you’re fully aroused, and during foreplay, have your partner pay particular attention to your ass. Really commit to it, rub it down, and get it nice and (say it with me) relaxed. It IS a muscle after all, so massage does wonders. Aside from manual stimulation, you can always get a few…

You can prep yourself with a plug. Ewww, butt plugs? No. Ooooh, butt plugs! Butt plug IS a pretty awful name…I think the best Google search I ever saw on the backend of SexyTofu was “cat tail butt plug.” Does this exist, and if so, someone please direct me to it. Anyway, if a butt plug sounds like a good investment for you, try this Pop Plug, size small for starters. Then once that feels cozy, move on to a medium. You can keep the plug in while you fool around, or have standard vaginal sex, just to get your bod used to having something up there. Not into toys? Just keep it old school with a finger or two…

Not all lube is equal
Please don’t ever try to have anal sex without copious amounts of lube. Unlike with clitoral stimulation, when too much lube can make it hard to feel anything, you can’t have enough lube in anal. Lube was actually what started my anal sex sound-off at my slumber party.

A few glasses of wine in, I forced the bride-to-be to try out one of the gifts I got her, Sliquid Sassy Booty lube. I mean, I just had her put it on her fingers and rub it around a bit to feel the pure superiority that is (vegan!) anal lube. You don’t have to love anal to love anal lube. It stays in place better than any other variety, and has a thick consistency like hair gel. I use it in every sexy situation I can. But I originally bought it because I was nervous about anal sex and did a bit of research on lubes…until then, I didn’t even know there was such thing as anal lube!

Aside form Sassy Booty, I love Maximus. It’s also vegan, and made with anal in mind. I don’t talk about my boyfriend’s sex habits on here, so I am NOT going to tell you that Maximus is his lube of choice.

Not all positions are equal
When most people hear “anal” they think about traditional doggie-style. I don’t suggest this position for anyone who is not already an anal sex ninja. While it may seem sexy in that “dominate me you bad bad boy” way, it gives you the least amount of control over depth and rhythm. And if you’re just starting off, trust me, you want control of depth and rhythm.

I suggest laying on your back with your knees bent, pressed together, and laying to the side so you’re shaped like an L. It’s sort of like a lopsided missionary position, but allows you to make eye contact which will help you feel connected if you’re nervous. It will also allow you more control. Another option is regular missionary (try it with a pillow under the hips for an easier entry) or spooning.

The poop factor
Both men and women get freaked out about the poop factor. I have never had a poop experience with anal sex. Not saying it doesn’t happen, but I think that fear that your dude is gonna pull out looking like the inside of a porta potty is an irrational one. In the XoJane piece, my favorite Emily words of wisdom were on poop:

“Anal sex is rarely messy. Your bowels are generally empty until you’re ready to go. That said, if your partner is completely uncomfortable with the possibility of poop, anal sex is maybe not for him. After all, it’s not like he’s fucking you in the ear and there’s poop in it. It’s a butt. It’s where poop lives. He’s the one who’s out of place. It’s like going to the zoo and then being surprised to see some animals.”

The zoo! Hah. I’m not into zoos but I sure am into that metaphor. That said, if you’re nervous about poop, be in charge of cleaning duty. Use a condom and dispose of it yourself after. Not using a condom? (You should if you’re not monogamous! Preach preach preach). Give your guy a wipe down before you let him head to the bathroom for a pee.

And guys…if you do find a little surprise waiting for you, PLEASE don’t make a big deal out of it. Your partner is already probably horrified, so make like a gentleman and clean up without having a hissy. No one likes a whiner, especially a post-coital whiner. Ugh.

For more tips (she talks a lot about the dangers of “reluctant anal,”) read Emily’s anal piece, because she is hilarious…And share your tips with me below, please!

About the author  ⁄ Zoe

Zoe Eisenberg is an author, editor and filmmaker living on the big island of Hawaii. For more from Zoe, find her on Instagram @zoahu, Twitter @Sexytofublog, or check out her book, The Lusty Vegan, available on Amazon and wherever books are sold.


  • Reply
    August 28, 2012

    It’s a butt, it’s where poop lives… OMG YOU CRACK ME UP!!! Btw.. I am all for anal sex..

    • Reply
      August 28, 2012

      Also.. I cannot stress enough.. you gotta prime the holyland before you just invade it. There’s been more then once my man has tried to just put a lil lube on and slide it in.. the muscles aren’t ready for that straight away.. tease it, use a finger or two, massage the area.. it’s called foreplay.. you’ll be amazed at how into it she’ll become if you take your time.

  • Reply
    August 29, 2012

    Oh wow, loved this post! Thanks for writing! I am so not afraid to say that this did turn me and made me wanna give it a try with my partner. :) We tried it like… 5 years ago, but neither of us were into it. But after reading this, I wanna try and convince him to give it a try, when we are in our new home after the move. Thanks again for the great post! <3

  • Reply
    August 5, 2013

    I’m interested in anal sex and I only had two barriers to it, you addressed one. The other is loosening of the sphincter, I was taught that anal sex loosens your sphincter to the point where it becomes unhealthy and you can’t control your bowel movements? I’m not trying to discredit you I’m just seeking information. I really a fear-free sex life but I won’t sacrifice my ability to hold my poop, lol.

    • Reply
      August 9, 2013

      Anal sex does not loosen the sphincter. The human body is amazing, and our muscles are resilient. Go!

  • Reply
    August 19, 2014

    i love it so much! just start it slowly..hmmmm

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