What to Expect When You’re Expecting Butt Sex

06/09/2009 1:07 PM |

In this week’s diary of a sex-store counterwoman, Lauren Wilkinson goes back door.

I like talking about anal for two reasons. The first is because butts are funny. Yeah, I said it. My favorite conversations with customers are always ass related. Like last month, when a woman worked herself into a lather over the butt plugs.

“Who would need those?” she demanded. After I explained their function she said, “Oh! Ok. I thought it was, you know, like a regular plug. To prevent spillage.” Spillage! Friends, you haven’t lived until you’ve heard the word “spillage” uttered in the context of a sex store.

More importantly though, I like talking publicly about anal, because it’s my way of calling bullshit on societal bottom shaming. For a plethora of social and psychosexual reasons, a lot of people still consider anal taboo.

But the way I see it, yeah, I’ve had a dick in my butt. So what?


What We Talk About When We Talk About Pain

I get asked two types of questions about pain. The first is from ass-virgins who want to know if it’s going to hurt a lot. The second is from people who’ve done it, found that it did hurt a lot and want to know if it’s supposed to.

Hopefully, everyone reading this is aware of the difference between sexy-pain and painful-pain. Painful-pain is show -stopping pain, like when a guy bangs you in the cervix with his penis or if your balls get into a spicy situation when you’re switching positions.

If you don’t use lube, you’ll feel painful-pain. It’ll feel like you’re getting an Indian burn* in your ass. A silicone lube (we like System JO Anal) is generally considered your best bet for anal intercourse, because it stays slick a long time.

I think it hurts a little at first. The key is, if you’re turned on enough, it’s the kind of pain you’ll like. It’s dull pain, not tearing pain. To put it in context, I found losing my vaginal virginity (which, for me, was a tearing pain) far more painful than losing my anal one.

Assistant Manager, Brandon B., thinks it shouldn’t hurt at all. His personal philosophy is that anal should be 90% foreplay. He likes rimming, “because it feels good and relaxes you really well. Some people think it’s gross. That’s understandable, but silly. I haven’t met anyone who’s had a tongue in their ass and not liked it.”

I rimmed someone once when I was younger, kind of by accident. I felt weird about it afterwards and that’s a feeling I still can’t quite shake. So obviously, like most sex acts, to rim or not to rim is a question of personal preference.


What’s it feel like?

To me, anal feels (as I’ve said) like pooping in reverse. Brandon thinks it feels more like, “having to poop and then pinching the loaf.” After my first time, I felt like my butt hole was stretched out and it scared the shit out of me (ha!) because I thought it was going to stay that way forever. It doesn’t.

For the top, they’ll find it’s like pushing through a packed subway car then suddenly (and surprisingly) finding themselves on a relatively vacant platform. “It’s like when I pucker my lips,” Brandon says. “My lips are tight but then there’s all this room in my mouth. And I hate that I just compared my mouth to a butt hole, but there you have it.”


Is it gross?

“If you poop or douche before hand it’s not very likely [that you’ll hit brown gold] but otherwise, if you enter the junkyard you have to expect to find at least one Doberman,” Brandon says.

If you don’t douche, one day the inevitable will happen. You can either NBD your way through the reality of a brown smear, or run screaming from the room and never see the person again. It’s up to you.

But dudes, shit happens. That’s why they coined the term.


*Is there a non-racist term for this?

30 Comment

  • who is coming up with these images? They are gold.

  • PLEASE add a “Tag Photo” feature L Mag (Hint: Lauren is on the left and my britches are blue).

  • Lauren Wilkinson WILL YOU DIGITALLY AUTOGRAPH AND TIMESTAMP YOUR RSS FEED FOR ME?

  • these douchebags don’t know what they’re talking about, best use them to clean out your poop release.

  • I’ve felt the pain-pain and I’ve been banged in the cervix. thanks for bringing both those up. second time not as bad. think it’s depends on all the above things you’ve mentioned.

  • Me n my boyfriend just started doing this. The first time it was horrible so the second time we used a toy. Then he went in and its wasn’t half as bad them the next time we started sex first them he entered in halfway threw of coarse being wet and we started out slow and then kepted it going and had no pain and it was pretty good wasn’t expecting it to be but it was so maybe Our tips will help

  • My name is Lawrence Lessig and my co-author Lee Baker and I authored a book about the benefits of anal sexuality. Without plugging our book, anal sex exceeds genital sex in the intensity of orgasms and the bonding experienced by the partners.

  • I love that photo of the butt chairs…. 🙂

  • greatest article ever

  • Very informative, very spot-on, very turn-on!

  • my wife was one of those” gross i will never do that, thats nasty” kinda girls when we met. now she LOVES getting her fart box smacked! every night im like, “oh yeah, lets f*ck babe, daddy wants that pussy” she’s like, “no, fuck me in my ass like you mean it” wow. talk about falling in love with it. she is always ready to leave early in the morning. cuz i pack her shit the night before

  • Absolutely loved this article!!! Major props to telling it like it is.

  • i like your allusion to raymond carver. great article!!

  • If youve only fucked once on you ass n its been over a yr will it be tight again for my second time?

  • I never had anal with girls but i wish it..
    I want to know how pines feeling inside it.

  • I’ve heard that the shape of the mouth is a mirror of the shape of the anus. does that apply to tightness also? i think so…not gross, just different ends of the same tube…

  • I want to try it but but I’m to scared to

  • I want to try it but I’m to scared to cn anyone help me?

  • You can only enjoy anal if you want it. If you’re ho-hum, it’ll feel like you’re shitting backwards and it will look like it too. If you want it, there is no sexy-pain, no pain-pain, and best of all, no nuggets of surprise. And only use oil based lube, not water-based. You want that hole greasy. And please people, rim that butt, smack it hard, and tease it before you boink “the forbidden fruit”. It’s the only way to get it primed for slamming, which you’ll ask for. And yes, it’s fucking amazing. Your eyes will cross. You will make noises like a farm animal.

  • Losing my butt-cherry (to a tall, cute crossdresser) did not hurt at all. It’s the best sex I’ve had so far. I can’t understand why more pretty boys don’t come after my well-maintained booty!

  • I’m happy for those who enjoy it to indulge in all the anal sex they like; personally, not a fan for myself, after a little experience. If a guy tells me he wants to engage in anal sex w. me, I’ll tell him I”m pretty sure I can get ahold of a good strap-on, and will happily indulge his desire to be f**cked. In any case, he’d need to take it first, before I do.

  • See that’s why I love the fact they say there is usually 5 girls per guy move onto the next girl. Sorry if you don’t like it honey but your not gonna force me to take it just so I can get it from you. Also I woulden’t want to have anal with a girl that don’t like it been there, I don’t like giving a girl pain she dosen’t enjoy.

  • my boyfriend has done it with other people and he wants me to do it with him but im scared to and he told me to look up anal sex and watch a video and so I did but that only made me more scared and now im kind of terrified to do it and I am scared that he will do it next time we have sex and he doesn’t live in the same state at the moment so I have some time to really research it and find out as much as I can but this is the only thing that I have found on this subject that is making me feel like it wont be so bad what I saw from that video made it seem like the worst thing ever but uh I don’t know do you have anymore information on it or any website’s I could go to, to get more information on this topic????????????????????????????

  • When my wife caught me dressing up in a tinkerbell outfit she told me i had been a bad little girl and bad little girls get spankings so she pulled down my lacy panties and started spanking me then told me to bend over and take it like a good little fairy .guess she kinda knew all along so she pulled out a strap on and pushed me down into the bed and fucked me for what seemed like a blissful eternity it hurt a little at first but then became very very pleasureable it was exhilerating the only problem now is that I wonder how it feels to have a guy fill your ass with steamy cum. I’ll bet it’s nice.

  • Dear (what do i do) I think if you want to get into the mood to go there with your boyfriend and videos and research have scared you then look up anal erotica as that will be more apt to put you in that frame of mind. As reading about it in a non icky fashion will help you to think about it as a more intimate experience then something to be laughed at or looked at on a porn as porn is not really real . You might could relate better to a person in a erotic story.

  • I can help out, babyblueeyes18. Post back if Sirius

  • I know someone who wants to experience but her husband doesn’t want to he has done it in his past but won’t with her. Any ideas I can tell her?

  • I like anal but everytime I’ve done it I get a bad pain in my feet.. Is that normal? Or should I be worried?

  • WHAT IS THE OBSESSION WITH ANAL?. I just dont get it. Im a guy and I love having sex with my girl and we do it everyday ,sometimes 2,3 times a day. But She just told me she loves anal. and i never did it. I thought it was for guys with small penis or some form of psychological abuse. Why would any girl want their natural sex organ neglected and get poop on the other persons sex organ? Then what? Laugh at eachother? and it hurts them. I will put my pinky finger in her ass and it is almost too tight for that. So how the #%*! do i put my dode in their? Is there one positive aspect to look forward to from having a stinky twinky!