My First Affair with “Miss Amy Wineglass”

Part One

The Moon Man Chronicles
The Scarlett Letter
5 min readDec 22, 2021

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Photo by Arzu Cengiz on Unsplash

The first time I noticed her, she was standing amongst a group of what looked to be her friends, and she just let off a different vibe than the rest. Her more outgoing friends were imbibing and overtaking each other in grandiose drunken statements. But she seemed less engaged in what her friends were gaggling about. She was more interested in how the napkin stuck to her wine glass. Holding the glass of Red Wine in her right hand, she kept gently pulling back the napkin with her left hand and then putting it back on the glass. And each time she did it, her eyes brightened up like she saw a miracle.

Or maybe she just had too many? Hard to tell.

I didn’t have the luxury of just waiting for her to notice me staring and send a little smile over. I couldn’t just walk around and introduce myself and offer to buy her another glass of wine with another napkin to fantasize about. I couldn't even use the bartender to send over a drink with extra napkins to be even more clever. My current situation was hamstrung because I was performing as a touring musician. To make matters worse, I was on stage as a-very-married-touring-musician in the middle of a show.

Photo by Tim Toomey on Unsplash

Things had slowed down in the bedroom for some time at this point in my relationship at home. Though I was being ogled weekly by drunken middle-aged women, the one middle-aged woman “I Want to Want Me” (See what I did there?) didn’t seem to be excited by my Bruce Wayne/Batman routine anymore. But I digress.

Months later, we arrived back at the venue, coming off two consecutive shows, and I was traveling alone. I hadn’t thought of her since the last time I was on that stage, and she immediately popped into my brain once I walked back onto the platform. I remembered her eyes and her vibe. I saw the spot where I noticed her holding that wine glass and playing with that napkin.

I couldn’t figure out why; she just made an impression.

Later on, in the middle of the set, I had noticed a group of females making their way closer to the front of the stage. In the middle of this group was Miss Wineglass. She was still holding that glass of red wine with her tanned right hand, which made her pink fingernails pop against the white bar napkin. The difference this time, she wasn’t staring at the napkin like it was a miracle. She was staring at me. And she was the miracle.

In full view, from 12ft above the ground, I got to take in all her beauty from head to toe. She was wearing tropical flip-flops with pink toenail polish. Her brown-skinned legs kept rising until they met the fray of her denim shorts. While she slowly grooved to the music, I noticed a slight dimple on the side of her thigh, which made the blood rush to my groin. Her bare mid-drift was below a ripped v-neck t-shirt with a random band on the front that I was too distracted to notice or care about.

She didn’t have large breasts, and she didn’t need them. But she was the type of woman who wouldn’t look right with them anyway. She had reddish-blonde hair that bounced neatly on her adorable features giving her the unique mix of cute and sexy. She had these deep green eyes that told a meaningful story any time you would catch them in your vision. Her lips were plump naturally, so she wore no lipstick at all. Her natural color already accentuated them.

As she danced to whatever we were playing, she occasionally spun around to reveal one of the most incredible asses I’ve ever laid eyes on. My reaction to it must’ve let off a scent because one of my bandmates had shuffled his way to my area of the stage like a vulture seeking its dinner. To be mindful of the rest of the audience, I relocated to a different spot on the stage but kept a close eye on Miss. Wineglass the entire time.

To my surprise, she kept an eye on me.

Immediately after a show is a mix of celebration and intoxication. But as the more sensitive one of this group of middle-aged children, I tried to avoid both on a grand scale. As the crew began to pack up the equipment and instruments, I retreated to the back of the venue to find the loading dock for my post-show celebration. Finding a quiet spot, I sat down, threw my aching legs over the metal grating, and pulled out of my pocket a tight but fully packed joint.

After a long three-show blast, with my ears still ringing, joint in my mouth, I thought to myself, “I deserve this. I earned this” and inhaled nature’s medicine. Watching that cloud of smoke rise into the night air, I got lost in the disappointment that I would be soon heading back home to stately Wayne Manor. Back to my regular job on Monday. Back to, life.

After my second pull and exhale, I heard footsteps coming from around the vans, so I immediately put out my joint because, at the time, it was still illegal. Sticking the joint behind my back, I straightened up and quickly lit a cigarette to throw off any questions by the authorities. I was out of state, and I wasn’t looking for any hassles.

Keeping my eyes skyward and watching the smoke rise into the clouds, I heard a female’s voice ask, “Are you smoking weed back here?” and I tensed up immediatly. I knew the venue manager was a woman, and I think I’d instead go to jail than tussle with her.

“Uhhhhh, what?”

“Are you…smoking weed…back here? Kush? Lala? Chronic? Sticky Icky? Do any of those ring a bell? I’m Amy….”

I lower my eyes to look down from my perch to see none other than Miss Amy Wineglass. My First Affair Partner.

Photo by Brooke Cagle on Unsplash

Part Two Soon

Moon Man

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The Moon Man Chronicles
The Scarlett Letter

I write pieces about the human condition, things that I like, and stories about the debaucheries of my life. simplemanonthemoon@gmail.com