Summary

The author recounts an awkward and unsuccessful sexual encounter with a woman he met at a bar, despite initial chemistry and intentions.

Abstract

In a retrospective article, the author shares a personal story from his youth about a failed sexual escapade. Despite his usual lack of success with women, he managed to connect with a server from the office bar. They ended up at her sister's apartment, but their attempt at intimacy was thwarted by an unexpected incompatibility, leaving the author feeling inadequate and unskilled despite his prior experiences. After a disheartening and fruitless effort to consummate their attraction, they resigned to sleep, and the author left the next morning, doubtful of any future contact. Reflecting on the encounter, he muses about the possibility of a do-over should the woman in question recognize herself in the story.

Opinions

The author initially considers himself to be a poor performer in romantic pursuits, yet capable under the right circumstances.
He perceives the woman's initial invitation as a possible romantic overture despite her protestations to the contrary.
The author attributes the failure of the sexual encounter to a combination of poor choice of location and an unexplained physical incompatibility, not to any personal deficiency.
The woman's critical remark about his sexual performance left a lasting negative impression on the author, affecting his self-esteem at the time.
The author left the situation with a sense of disappointment and unresolved tension, hinting at a desire for redemption.
He extends an open invitation for a second chance, suggesting a willingness to confront and possibly rectify past embarrassments.

She Told Me I Was Bad in Bed but the Whole Thing Was Damn Strange

A true story of sexual misfortune

This story happened a long time ago, so if you’re my ex-wife reading this — and statistically you probably aren’t — rest assured it was well before we met.

Then as now, I was a poor excuse for a ladies' man. Still, after a few drinks, I could spout a little poetry and occasionally evince enough doe-eyed sincerity to kindle a woman’s natural generosity of spirit into a spark of sexual attraction.

The Meet-Cute

Every Friday night I would join a select group of co-workers at the bar on the ground floor of our office building. One evening, wearying of our weekly practice of mocking everyone who wasn’t us, I struck up a conversation with a young woman seated alone on the periphery of our group.

She was attractive in a way I would have called “cute” back then, with short dark hair and a smile full of promise. She said she was a server at the attached restaurant who’d just finished her shift and was winding down before going home. Beyond that, any knowledge I ever had of her, including her name, has been lost to time and alcohol.

Still, I remember enough for the purposes of this story.

Eventually, she invited me back to her sister’s place, where she’d been apartment sitting.

“I’m not trying to pick you up,” she said.

I replied with an exclamation of exaggerated surprise, as if the idea hadn’t occurred to me. But while I’ve always had a tendency to take people at their word, I suspected, certainly hoped, that she was trying to pick me up.

Either way, I’m a biddable drunk, and after saying farewell to my colleagues — who didn’t mind being ditched in a good cause — we found a cab. We stopped off at my place first so I could change out of my suit and tie, and grab a toothbrush, because you never know.

We got to her sister’s apartment, a beautifully renovated loft with floor-to-ceiling windows. On a side table stood a picture of said sister with some friends, and I recognized one of the friends as a regular at my gym. This coincidence will not factor into the story in any way so feel free to forget it. Small world, though.

We had more drinks, and briefly indulged whatever fiction we’d contrived about our reason for being there, probably discussing Jane Eyre or listening to Coltrane or some other cultural pretension.

As you’ll have guessed by the title of this article, shortly the salon chatter lost its charm and we moved to the main event. The sequence would have been familiar — kissing escalating into hardcore tongue action, stroking and probing hands, then a tugging on my belt, followed by my standard cry of “Madam, you take strange liberties!” and rapid acquiescence.

“You Shall Not Pass”

For reasons I’m unable to explain, we opted to attempt fornication on a wooden chair with a high back and arms (in my memory it’s a cross between an electric chair and the Iron Throne, but I doubt this is accurate). The chair would have been a challenge for a pair of gifted contortionists operating at full mental capacity, and for two alcohol-saturated humans of middling flexibility, it was well-nigh impossible.

Still, we managed to wrest our bodies into what seemed like a workable situation, only to be stymied at the point of insertion. The damn thing simply wouldn’t go in.

First I’ll deal with the obvious questions.

Yes, based on her audible excitement and my scouting of the territory, she was fully prepped for action, as was I. And although I’m satisfied with my endowment — and believe others have been — I’m not sized in a way that would hinder successful completion of the sexual act.

This initial failure wasn’t a dealbreaker though, since we could blame it on poor choice of sexing apparatus. We relocated to her sister’s bed.

The move provided only a brief respite from frustration. With great caution, we assumed a basic missionary pose, her with legs wide and knees raised, and me in between them, lowering myself gently into the starting block.

I might as well have tried to fuck the bed.

Hips were shifted — up, down, sideways. Alternate angles were attempted. Guiding hands were brought into play.

Nope. Like some monstrous Ikea bookcase of flesh, her nut would simply not thread my bolt.

After several minutes of fruitless effort, she yanked herself out from underneath me and sat up against the headboard.

She eyed me critically. “You’re not very good at this, are you?”

That short sentence sliced like a dull razor through the stubbled chin of my self-esteem.

Now as I said, I wasn’t racking up Wilt Chamberlain numbers, but by my mid-twenties, I’d secured enough coital experience to consider myself at least competent.

I don’t think I replied; anything I said would have sounded weak and defensive. It’s possible a tear rolled down my cheek.

We could have tried alternate positions or olive oil or something, but instead we gave up. Neither of us was really invested in the relationship, and frankly I didn’t want to risk a penile fracture slamming into whatever she had going on down there.

So we went to sleep.

I woke up early the next morning, got dressed, and slipped out while she slept. I’m about ninety-five percent sure she was feigning sleep anyway, which was the classy thing to do because I doubt either of us wanted to relive the previous night’s debacle over toast and coffee.

I left her a note with my phone number, securing the moral high ground with complete confidence that she wouldn’t ever call.

She did not.

Epilogue and Invitation

I could say I’ve thought of her often over the years, but that would be a lie. Then a couple of days ago the experience came to mind unbidden and I thought it would be funny to write about, so here we are.

That said, if you are a woman of a certain age and this story sounds familiar, please feel free to contact me for another kick at the can. Life is all about redemption.