Love & Sex

My First Time

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Male • 29 years old • Milwaukee, WI 

I'd been set up on a blind date with a woman who sold wine, an occupation which had a certain Dionysian appeal. We spoke over the phone a couple times, and a few days later met at her high-ceilinged, Victorian-style home. She was girthier and older than depicted in her e-mailed pictures, and did this unexpected, middle-aged, semi-spiky hair-thing that says (perhaps a little too loudly), "I'm not really young enough to spike my hair, and not really old enough to let go." On the obligatory home tour, I also learned she had a young daughter — not by any means offensive, but a fact omitted during our perky phone conversations.

We ventured to a restaurant where she was friends with the owner — and seemingly everyone in attendance. Dinner turned into a wild carnival ride of wine consumption. She was friendly — very friendly — and prone to over-animating nearly everything she said with loud laughs, wide-eyed declarations, and often forceful touches. But as the evening went on, our age difference was blurring. In fact, everything was blurring as the consumptive tour of French wines continued.

Post-meal (but sometime before the unneeded dessert wine), I said something she found especially amusing. In a supposed errant knee-slap, she grabbed my crotch. She stared at her hand, looked up, feigned shock, then growled, "I know what I want for dessert." I should have seen this coming. The ruse of "a must-try vintage hidden away for a special occasion" brought me back through her front door (to say nothing of my being completely unable to drive). It was near immediate, post-cork popping — a sniff, a swish, a taste and a mounting.

Illustration by Thomas Pitilli

Bunched-up clothes, mashed faces, loud groans… and then an abrupt pause. Past experiences with such hesitation have taught me that sobriety-induced guilt is often the cause. I offered to pour more wine, but she dismissed that with a throaty laugh, then said, "I feel so close to you, I want to do something for you." I leaned back against the pillows, intrigued by the prospect.

She stood up, straightening her remaining clothes, playfully tucking a breast back in. She was now near-nude, her mashed spikes pointing east and west; my level of regret crept upwards. Overtaken as if climaxing, she closed her eyes and tilted her head back. Her lips formed a circle. She inhaled, exhaled, and then: "All I wanna do is have some fun… I got a feeling I'm not the only one… All I wanna do is have some fun…" She sang so loudly I actually jumped, instinctively covering myself with whatever clothing I could grab. Recovering quickly, I smiled awkwardly as she continued her Sheryl Crow impersonation, so much more naked in so many ways.

"I sound just like her, don't I," she breathlessly gasped to her quickly deflating audience member. I was sobering, and knew there was only one right answer: "Absolutely." I hung suspended between wanting to get laid and wanting the singing to end, with no easy route to either. I was treated to the full song, to which I responded with overly enthusiastic applause, hoping to end the concert. Beaming, she bowed deep, her pendulous breasts swaying.

"I'll take requests for other Sheryl Crow songs," she beamed. Stunned, I stammered something signifying appreciation and implying termination; it was ignored. A live greatest-hits album later, she gleamed with post-performance sweat and was seemingly near rapture. She spilled into bed, and I did my best to go through the motions, but I was haunted by the line, "Love is free," which was working overtime to frame a night of heavy costs.

I eventually expired with her singing "If It Makes You Happy" in my ear. I fully intended to marine crawl out before the impresario awoke. But with bright sunlight pouring in, my pounding headache was magnified by my now sheet-wrapped date trying to massage me back into a serviceable condition under the covers, while gently cooing, "Now you're my favorite mistake… Yeah, you're my favorite mistake… You're my favorite mistake."