Flavor of the Week: No Ifs, Ands or Butts

I’VE ALWAYS BEEN jealous of women who enjoy anal sex; for me, it’s an act of tedious preparation for little to no gratification other than the psychological success of actually stuffing something bigger than a finger up my reluctant sphincter. Plus, my rationale is that I have two other perfectly fine and capable holes prepared to accommodate—why would you go sticking it up there? But I’m not some prude, and once in a while, if I really like the dude, I’ll play ball with his big ol’ bat. I’m a nice girl like that.

Several years ago, I had a boyfriend who was hell-bent on getting me to take it up the ass for him. He would drop subtle hints, like the time we were having dinner at an Italian restaurant. Picking up the end of a loaf of bread and waving it suggestively at me, one eyebrow cocked, he announced, “In Italy, it is traditional to pack the buttend of this bread with Nutella.” My response was, “Well, we’re not in Italy, and could you please pass the Parmesan?” To his credit, the boyfriend was well endowed, something he claimed was “a curse” that afflicted all the men of his family. I wasn’t about to investigate the legitimacy of such a statement, though it did help me see his taller, more handsome brother in a different light.

One night, after my ingestion of far too many vodka-based cocktails, he and I were really going at it, with me on top riding him like my favorite horse on a carousel. He inserted one finger into my back door and I didn’t stop him. In fact, I encouraged him by asking, “How about two?” The lube I’d purchased a few days earlier was helpful, and his second digit slid right in without a problem. “Alright,” I said, since blood was no longer flowing to my brain, “let’s try it.”

I flopped onto my back and reached for the lubricant. “Be generous,” I informed him. I could feel him applying a copious amount of what felt like cold oil to his penis and my backside. Due to the excessive amount of lubrication, his member slid easily into my terrified and illprepared butt. I don’t know if you’ve experienced this, but I liken it to searing, white-hot pain. I went blind. Instinct kicked in; I leapt off with a shriek. All I could think was, “Walk it off, Imogene, walk it off,” so I strode through his small junior one bedroom but not before throwing a pillow and punching a wall for good measure. I found myself in the kitchen and started washing my hands because, well, what else was there to do?

But this was by no means my worst experience. A few boyfriends later, I found myself dating a younger man. He was tall, handsome and came equipped with an enormous appendage. On our first date, we went to his apartment where I drunkenly slipped off of his satin-sheeted bed to fly face first into the corner of his marble nightstand before landing on top of a wine glass that shattered into my bosom. Luckily, he had graduated Harvard pre-med and deftly plucked out the shards from my chest before expertly bandaging me up. Somehow, he actually wanted to see me again after that, and we started dating.This first night was predictive of our relationship because he introduced me to many sexually deviant experiences, including sex clubs where we engaged in orgies. Granted, I was no stranger to group sex—having participated in threesomes and more in the past—but this was extra-seedy. And extra sexy.

I’d initially informed this beau that there was no way I’d ever let him anally penetrate me, but his appealingly dominant nature convinced me otherwise. One night at his apartment, as we were entwined together in his bed and needing a safe word, I suggested “banana,” inspired by a recent Family Guy episode we’d watched together. Again, I found myself on my stomach, this time with my legs splayed open, wrists handcuffed.

“Be gentle,” I reminded him, pliant beneath his body.

And at first, he was, slowly easing open my sphincter with his tongue and fingers, before graduating to the tip of his penis.

“Ow!” I yelped, twitching in response. “Are you OK?” he asked, pausing briefly. “Yes, I think so.” He continued his ministration at my rump, and I concentrated on trying to breathe. My face was nestled in a pillow, and I could smell the combined scents of his shampoo and hair product. Briefly, I wondered if they were comedogenic.

And then came the tearing, what felt like my entire body being ripped apart at the seams.

My head bobbed up in reflex, my neck clenched, my mouth opened and I heard myself shrieking “Banana!

Banana!” I realize now that this may have been the perfect safe word because who wants to fuck a girl who is screaming about fruit?

He jerked back and sighed. “Why are you being so difficult?” he snapped.

I awkwardly rolled over, maneuvering my trussed body into a sitting position so that I wouldn’t feel so vulnerable. “Look, have you ever taken it up the ass?” I asked.

“No,” he snorted.

“Well then, until you do, I don’t think you have any right to give me guff for this. In fact,” I decided, “I’m not going to let you do me in the butt unless you let me do you in the butt first. How about that?” I finished triumphantly.

That suggestion effectively took anal off the menu.

It’s been several years since that episode but my body retains the memory, and I don’t think it will ever forgive me the trespass. C

Imogene Lee is a native New Yorker and an awesome slut. Check out her writing at awesomeslut.blogspot.com to follow her search for the perfect mix of pervert and prince.