The Glasses-Wearing Waitress Who Was Waiting for My Confession

If they had to describe Lorena in a single sentence, they’d say she’s the kind of woman who goes unnoticed. She’s five-foot-three, with shoulder-length wavy brown hair, thick brown-framed glasses, and she dresses in straight-leg jeans and loose blouses that don’t reveal a thing. She speaks little. She almost never jokes. She laughs only on rare occasions, and when she does, it’s softly, as if asking permission. She’s not the sort of woman who turns heads just by walking through the door.

And that was precisely what ended up trapping me. No matter how much I looked at her and looked at her again, I couldn’t form a clear idea of what she was like under all that neutral appearance. That inability to figure her out did me in. It hit me so hard that I spent three years of my life obsessed with finding out.

Lorena is thirty-eight and owns a small bar in the center of town, La Casona. She runs it with her brother and her mother, but the one who spends most of the day between the bar and the kitchen is her. My parents had been regulars for as long as anyone could remember, so I’ve known her since I was a kid. It wasn’t until I was well into my late twenties that I started noticing she never stopped looking at me.

At first I didn’t think much of it. I figured it was a coincidence, or that she was looking at someone behind me. But over the years, and with my fetishes already pretty clear in my head, I started looking back. I learned her routine. I learned what time of day she was alone behind the bar. I learned the little gesture her mouth made when I walked in: she would bite her lower lip for a moment before greeting me.

For years that’s how we went on, exchanging furtive glances. She knew I was looking for her and she liked it. I knew she was looking for me and that turned me on. It was a silent, sustained game that became routine without either of us doing anything to break it.

***

Last summer something changed. Lorena started dressing differently. Closer-fitting clothes, blouses with fewer buttons, jeans in a different cut. She flirted more openly with customers, smiled more, stretched out conversations. The first afternoon I went into the bar after two months without seeing her, I nearly dropped my backpack on the floor.

She was wearing a sleeveless cream-colored shirt, flared jeans tight at the hips and waist that showed off a perky ass I hadn’t known she had. Black strappy sandals, her hair pulled back into a low bun with two strands escaping, and her glasses. The usual ones, the thick-framed ones. I had to sit down at the first table I found because my cock got so hard there was no way to hide it standing up.

I have a weakness for women with glasses that I can’t explain. And when they wear sandals or flip-flops with their feet out in the open, my mind goes straight to the gutter. Lorena, that afternoon, combined both fetishes in the same body. It was unfair.

She came up to my table with her notepad in hand. She looked at me over the top of her glasses, with those brown eyes that seemed as if they’d never harmed a soul in their life.

“What can I get you?” she said.

“A shot of Frangelico,” I said, trying not to let my voice give me away.

She went back behind the bar and I watched her reach up for the bottle on the high shelf. Her shirt rode up a couple of inches and exposed the base of her back and the start of her ass above the jeans. I closed my eyes for a second and breathed. My cock throbbed against the zipper and I had to adjust it under the table, pressing my fist against my thigh.

When she came to serve me the shot, there was something odd. She brought the glass over, and as she set it down on the table she made a move as if to brush my hand. She did it so clumsily that it was obvious it wasn’t her habit, that she had been thinking about it and hadn’t known how. Her hand hovered for a second over mine, and then she pulled it back.

“Thanks,” I said.

I went out to smoke. I needed to clear my head. The sidewalk outside the bar led to an alley that smelled of jasmine, and I leaned against the wall with the cigarette in my hand, thinking that after so many years something had changed between us and I didn’t know exactly what.

When I went back in, she was still behind the bar. I sat on a stool and asked for a glass of water. She brought it with her other free hand, and the moment the two of us went to grab the glass at the same time, she put her hand over mine and left it there.

I extended my index finger and slowly stroked her wrist, following the line of the vein. I had never touched her skin before. It was softer than I had imagined it would be after three years. When I looked into her eyes, I saw her bite her lower lip, and a small moan escaped her. She cut it off abruptly with a nervous “thanks” and turned around to wipe down the coffee machine, which wasn’t dirty.

I didn’t sleep that night.

I spent hours on my back in bed, with my cock hard as a stick, jerking it slowly and thinking about her. I’d close my eyes and see her stretching up for the bottle, her back bare, and I’d imagine sliding my hand inside her jeans, palming her ass, finding the thong string between her cheeks. I came three times that night. The first time thinking about her mouth around my glans. The second time imagining her on all fours on top of the bar stool, with her glasses on and her jeans pulled down to her knees. The third, near dawn, imagining her sucking me off under the bar while a customer ordered a coffee on the other side.

It had taken me three years and twenty seconds to realize that she was waiting for exactly the same thing I was.

***

It took me three days to gather the courage. I worked out the time when the bar was usually empty, one of the early afternoon hours, when the laborers had already gone back to work and the retirees hadn’t yet arrived for their card games. I walked in without saying hello.

The bar was empty, just as I’d expected. Lorena was sitting on a stool at the far end of the counter, reading something on her phone, legs crossed and one sandal dangling from the tip of her foot. She looked up when she heard me come in. She said nothing. She waited for me to come closer.

“What can I get you?” she asked out of habit, without moving from the stool.

“An iced coffee,” I said, and sat down beside her.

She made the coffee without getting up, stretching her arm to the machine, never taking her eyes off me. When she set it down in front of me, we both fell silent. I could feel the heat of her arm a hand’s breadth from mine. I could smell her perfume, something citrusy and clean. And above all, I could feel that she was waiting for me to finally say what I had gone years without saying.

“Lorena, you turn me on,” I said, just like that, without embellishment. “There’s something about you I don’t understand, and it turns me on like crazy. I’ve been thinking about that for years. I’ve been jerking off for years thinking about your cunt.”

I thought she was going to stand up. I thought she was going to throw me out of the bar. I thought she was going to tell me she was married, or that I had the wrong idea, or any of the thousand ways it could all go wrong.

“About time you told me,” she said. “I’ve been touching myself for the same amount of time thinking about your cock.”

She said it softly, without smiling, without drama. As if she’d had the line ready for so long that it had already lost its edge.

That was when I understood that all my suspicions were true.

***

What attracted me most about her, I tried to explain later, was that feeling that she might be capable of anything, in bed and out of it. At first glance she seemed like the girl who had never broken a plate in her life. But the more I looked at her, the more details made me doubt that.

The way her ass moved under her jeans, without revealing absolutely anything, as if she weren’t wearing panties. Or as if she were wearing a string thong. Or a triangle thong. Or nothing. That doubt was, for years, the engine of my best wanks.

“And with your answer,” I told her, my face now very close to hers, “I knew you were one of those women who live at the extremes.”

“And now what?” she said.

We were so close that our breaths mixed together. The heat coming off both of our faces was almost unbearable. Under the stool my cock was outlined in my pants, and she looked at it for a second without hiding it. She ran her tongue over her upper lip.

“We rent a rural house,” I said. “One weekend. Far away. Somewhere no one can hear us fucking ourselves senseless.”

She smiled for the first time. A crooked smile I had never seen before.

“I like to dominate,” she said. “I like having the other person on their knees, mouth open and tongue out, swallowing whatever I tell them to. I like tying, spanking, and sitting on someone’s face until they can’t breathe. I’ve got toys. Quite a few. Thick dildos, a harness, rope, nipple clamps, a steel plug. And I like using it all on the first night.”

“You can use them if you’re capable of dominating me,” I said. “I like being in charge too. I like grabbing hair, pushing my cock down someone’s throat, fucking ass without asking permission. And no woman has ever gotten the better of me yet.”

“With me that’s going to change. I’m going to break you. I’m going to leave your ass wide open and your mouth full of my cunt.”

“Then we’ll have to fight in bed to see who wins.”

She picked up her phone from the stool. Searched for three seconds. She showed me the screen with a rural house in a mountainous area, no neighbors, no signal, nothing around it. She booked it in front of me. She didn’t ask if the date worked for me. She didn’t ask if I had money for my share. She just did it.

“We leave Friday afternoon,” she said, and put her phone away.

Before I could answer, she slipped her hand down beneath the counter and squeezed my cock through my pants. She took hold of it completely, sizing it up from top to bottom, pressing with her fingers like someone weighing fruit at the market. A short sigh slipped out through her nose.

“Bigger than I imagined,” she murmured. “Good. Worth it.”

I slid my hand under her shirt, brushed the skin of her stomach and moved slowly upward, until the edge of her bra. I unfastened it from the front with two fingers, without taking it off. She closed her eyes for an instant. I pinched her right nipple, rolled it between my thumb and forefinger, and felt it harden at once. A soft, muffled moan escaped her, the same one she had gifted me the first time behind the bar.

“If you keep going,” she whispered, “I’ll close the bar and suck you off right here.”

“Close it.”

She laughed, this time louder. She pulled my hand out from under her shirt firmly.

“No. Friday. And I want you to arrive with your balls full. No wanking until then. If I catch you lying, I’ll cut your balls off.”

At that moment a customer came into the bar. An older man who ordered a small coffee and sat at the far end. Lorena stood up, fastened her bra with a discreet movement under her shirt, looked at me for an instant over her glasses, and went back to her lifelong role as the waitress.

I finished the iced coffee with my cock still throbbing against the zipper. We exchanged phone numbers on a napkin and I left.

***

Just minutes after I left the bar, my phone rang. It was her. A photo. A close-up of her pussy, with the blue thong pulled aside by two fingers, the lips glossy with wetness, the swollen clit peeking out between the trimmed hair. The quality of the photo was bad. The intention was perfectly clear. It came without text, without emoji, without anything.

I got into the car in the supermarket parking lot, unzipped my pants and pulled out my cock already soaked with pre-cum. I stroked it fast, hard, looking at the photo over and over, imagining my tongue between those lips, sucking her clit until I came in my mouth. It took me less than two minutes to come, and I did it in thick spurts against the steering wheel and the palm of my hand. I answered with another photo: my right hand covered in still-warm semen, thick white strands between my fingers, and my wristwatch showing the exact time she had sent me hers. No text either.

It took her three minutes to write back, this time in words: “Slut. I told you no wanking until Friday. Now you’re going to pay for it. Friday I’m going to feed that to you, and then I’m going to make it come out your ass.”

I replied with a single word: “Try.”

She answered with a three-second audio. A long, dirty, hoarse moan, and at the end a phrase spoken through clenched teeth: “I’m putting two fingers in thinking about your cock.” Then she hung up. The message cut off. Nothing else.

I shut the car and sat staring at the roof with my cock half-hard again, still dirty, not wanting to clean myself up.

There are four days left until Friday. Four days and fourteen hours, exactly. I’ve spent two without sleeping, running through my head what toys she’ll have bought, what panties she’ll choose, whether she’ll do what she said, whether I’ll be able not to give in before the time comes. And, above all, what face she’ll make when I show up on Friday at six with my backpack over my shoulder, my balls full, and my nerves hidden.

In a few days I’ll tell you how our fight went.