How To Not Give The Gift Of Anal Sex


Scene: Santa Cruz, California, December 2008. My boyfriend and I are spending our first Christmas together with his family, and I want it to be special. Coincidentally and totally unrelated, though I don’t think that at the time, I’d recently passed gas in front of him for the first time and he’d barely reacted. I felt like that liberating moment opened a new door in our relationship – a back door, so to speak. My train of thought: If he’s fine with my farts, he must want to have anal sex with me on Christmas!

I think I am onto something brilliant here. We’d done every other “dirty,” “adventurous” sex thing I could think of with the help of lady mags. According to my research, I needed to keep up the bedroom surprises if I wanted to keep my man. Also according to my research, buttholes are on trend. And if I’ve learned anything from pop culture, it’s that the privilege of sticking it in my vagina alone is just not good enough.

I also consider that I’ve hooked up with more than one guy who’s interpreted me saying, “I don’t feel like having full-on sex tonight” as, “I’m super cool with you trying to sneak it up my poop chute though!” Despite their suave advances, I’d managed to have kept that orifice a dick-free zone through the years, mostly because dudes have enough trouble finding my G-spot as is, so why confuse them with an extra avenue to get lost in?

But this Christmas I felt like, now that I’m sleeping with someone I actually love, it’s time for me to be more relaxed about exploring different avenues, if you catch my drift.

And so, it was decided: I would be giving my boyfriend the gift of anal sex for Christmas.

I was practically skipping to Downtown Santa Cruz’s sex (positive) shop for lube when I called my best friend to brag about my great idea.

There was a long pause on the other end of the phone. “Hon, um, don’t you think that’s kind of… a weird thing to gift someone?”

No, I said indignantly. I do not.

“Hon, seriously…” I hung up before he could convince me otherwise.

I traipsed into the sex (positive) shop and was immediately greeted by the salesperson, a white girl with blonde dreads with the nativity scene tattooed across her chest. Her name was Esmerelda. I laid out my master plan, to which she clapped her hands together and exclaimed, “I think that’s a beautiful idea! Follow me.” When she turned around, I noticed she had wrapped one of her dreads around what looked like an unused tampon.

Esmerelda parked me in front of a bucket of single-use lubricant packages. She looked me up and down, closed her eyes and sighed deeply. She plunged her hand into the bucket and pulled out a little black bottle with a sly smile. She called it “the super glue of anal lubricants,” which confused me and made my rectum clench involuntarily. She forced it in my hand, and I suddenly felt very embarrassed and wanted to leave immediately. I fumbled for my credit card.

At the register, she suggested I slide the lube into his stocking with a wink that told me maybe she meant it to be a euphemism? I wasn’t sure but I nodded eagerly. Yes, I thought, because we will open the stockings in front of his parents. This will be appropriate and a total turn on!

I quickly backed off that idea when I told my best friend and he gasped in horror so loudly I dropped my phone. Still, I was determined to deliver the lube in some memorable way that you might see in a rom-com produced by Ron Jeremy. Should I hide it in his shoe? Replace his toothpaste with it? Tie it to a brick and throw it at his head? Yes, maybe that last one. That will be endearing like the relationship between Krazy Kat and Ignatz Mouse.

If we’re going with that last comparison, then Offissa Pupp represents my holiday bowel movement irregularities. When we got to my boyfriend’s parents’ house, I drank too much wine and then inhaled most of the cheese plate, so I was too constipated that night to fill my colon with anything else. The next night, Christmas Eve, I again drank too much wine and couldn’t even be bothered to take my contacts out before bed, let alone coordinate any back-to-front partner acrobatics. And then on Christmas night, I got so nervous with anticipation that I made myself constipated again. I shamefully hid the lube in the bottom of my suitcase and we went home.

Unpacking my suitcase in my bedroom, I pondered: What the fuck was I thinking? Gifting my boyfriend with anal sex?!?! Ew. Ew ew ew ew ew ew. Gross, Becky. Stop being so lame.

Needless to say, I left it in my suitcase and forced myself to not think about it, only to find it a few years later past its expiration date. That night, I asked my boyfriend if there was any bedroom thing we hadn’t done yet that he’d like to, ya know, try.

He thought for a moment. “Well, in high school, I thought anal sex would be the shit… until someone explained to me that it’s literally the shit. So, nope!”

Good to know, babe. I probably should have asked you in the first place instead of ass-uming (har har) that anal sex was your deepest, darkest desire, and that I was inadequate for not intrinsically knowing it. So kudos to me for letting that butthole lube expire instead of mortifying myself. Who knew constipation could be a Christmas miracle? 

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