When Sex Becomes a Pickle

Q. When my boyfriend and I first got together, he was very interested in trying anal sex. It took a couple of months of convincing, but I finally agreed to try it. I quickly found that I loved it. It consistently gave me some of the most intense orgasms I’d ever had. And for a few years, everything was good. Then we went through a rough patch where we weren’t really having sex at all. Though we’re mostly back on track now, it seems that anal sex has become a thing of the past for us. It’s downright painful now, and not in the good way. Even anal stimulation is proving uncomfortable. We’ve tried a number of things (more lube, less lube, finger first, making sure he trims and files his nails before doing the finger first, using a butt plug before the penis), but nothing seems to be working. Do you know if this is common? Is it something that will take more time, or more attempts? Or is it possible that I’ve simply outgrown enjoying anal sex? I’d hate for that to be the case because, as I said, it gave me some of the best orgasms of my life. But now it’s just a constant source of frustration. Do you have any advice or encouraging words?

A. That’s quite the pickle, my dear frustrated one. Such a strange, yet common one, that it reminds me of this one summer, when, oddly, speaking of pickles, all I wanted to do was eat was pickles. Not just any pickles, mind you. They were these new pickles that were only from this one market that was quite some distance, but worthwhile nonetheless. I’d walk blocks from my work to get some on my lunch break, crunching them all twelve blocks back to the dim little store in which I worked. I’d drink the juice greedily on my way home, as if it were a magic elixir that would restore youth and vitality. My partner would ask, “What do you want for dinner?” regretting the second this question slipped past his lips because he knew what I was going to say. Given that he was not as into the pickles as I was, it was a source of frustration for both of us come dinner time. These pickles were my life. Something was just so delicious and perfect about them, and I didn’t understand what, but each and every time I ate one, I felt great. I was full, I was hydrated, and I was perfectly content to eat nothing but pickles for the rest of my natural-born life.

Then, one day, as I was filling up my normal plastic bucket of pickles, I couldn’t help notice that there was a smell, which says quite a lot, on account of me being in New York, where everyday seems to be a game of, “What’s that smell?” Russian Roulette. It wasn’t terribly noxious, but it was discernible enough to notice when getting my beloved pickles — subtle, yet disgusting. With a bit of a furrowed face and a few bucks spent, I was out of there, ready to feast on the pickles I had thought about since my eyes opened that morning. I couldn’t even wait ’til I got home; I had to have one immediately. I took an especially juicy looking one out of the container and put it to my lips, ready to be transported into the comfort of sweet brine, salt, and new crunch. I could almost taste it.

Then I actually tasted it. And it tasted like garbage.

I spat the pickle from my mouth. What in the hell did I just eat? Okay, I figured, every batch has to have a few bad ones, right? So on to the next pickle, which, my friend, was just as bad as the last. Frantic, I tried another. Still bad. Another, then another, then another, and then, the very last pickle, sitting lonely at the bottom. This has got to be the one, right? The one good pickle? Yet as soon as it approached my mouth, I was already ahead of the game, and on my way to retching, equal parts hungry, sad, and frustrated. These were bad pickles, that had to be the answer, plain and simple. The batch had just been messed up. Next week, all would return to normal and I would have my delicious pickles back into my satisfactory reach.

Except that didn’t happen.

That next, new weekly batch of pickles? They tasted exactly the same. Really, each time I returned, I attempted to just try it again, one might say I was forcing the issue, really. I would demand of my partner to tell me the cold, hard truth: “Don’t these pickles taste different? What have they done?” He would look at the temper-tantrum throwing toddler his adult girlfriend had turned into, wondering why it was that she seemed to be having a nervous breakdown over pickles in the deli aisle. “They taste the same to me,” he would say warily, as if backing away from a wild animal, waiting for me to hang my head in confusion or break down into a full-on banshee wail, morning the most serious of crimes, bad pickle taste. I tried ceaselessly, furiously, over and over again. Yet, they continued to taste the same.

So what of pickles and anal sex, my love? Well, it seems like this pickle you have found yourself, and it is indeed a pickle, is not a situation of “needs more lube, less lube, finger first, trim and file, and a butt plug,” but of convenience. We creatures crave variety, my sweet pea. Sure we have our favorites, who doesn’t? But sometimes we just do things until they run their course. I’d love to say that there might be a technique out there for you that might magically put the pep back into your anal sex routine, and there might be. But it sounds like you have perhaps outgrown what this served for you. It is no longer the convenience of sexual pleasure it once was, and that, of course, is frustrating. Perhaps your butt is subconsciously still distrusting of your partner, given your recent rough patch. Butts can be psychic like that — really, all sexual organs can. Not that your butt is gazing into the crystal ball, divining its future usage, but the sphincter is a muscle and like all muscles when stressed, gets tense. Think of what it is when two people trying to recreate the magic of a once-fabulous sex habit and only getting more and more frustrated that they can’t. Tense butt, indeed.

Either way, it might be time to walk away… from the anal, that is.

I’m sure the two of you, being the creative people you are, will be able to find a new routine in your sex life to keep it alive, but to keep on keeping on with the frustrations you are experiencing now? My love, life is stressful enough, there is no need to add more stress to an activity that is supposed to be fun and pleasurable. I have faith that you will set aside the once trick pony of anal sex.  You might just enjoy trying something new. As a famous philosopher once said, “And now for something completely different.” Consider it not a loss, but a gain, a way for you and your partner to let go of convenience and begin to re-explore each other’s sexual hopes. You might be surprised by the new intimacy it creates.

Oh, and those pickles, dear reader? A few years later, I happened to be in the same market, picking up a few odds and ends. My new summer food obsession had become Horiatiki Salata, sans the iceberg lettuce leaves (I’ll speak on behalf of all who reside by the Mediterranean in that we do not ever use iceberg lettuce, not ever, not anytime). I’m happy to give you the recipe, but before I get too off track, somewhere in between finding the perfect Horiatiki and a nice batch of olives, lo and behold, there they were: my exes, my old cohorts in taste. The pickles. Like approaching any once friend or partner in a public setting, I did so with caution. Everything looked the same, yet was different. I didn’t feel so manic about needing to eat them, nor did I feel like they were the perfect treat. Instead, they were what they had been the entire time: pickles. Then I saw it, just lying there, ever so casually. The sample dish, full of tiny pieces of the pickles. I wondered, would it be the same as so many years ago? Would I cringe in disappointment, gag on the same frustration as I had before? I put toothpick to pickle, and popped it in my mouth. It wasn’t that bitter, disgusting imposter that I remembered, nor the heaven-sent treat meant to rescue me from all other weak food options. It was good and satisfying, different, but still, I liked them. Perhaps I’d come back in a few weeks to get some.


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By TheLadyMiss

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