The Invitation from My Boss That I Shouldn’t Have Accepted

Thank you for the welcome you gave me when I introduced myself a few days ago. It really made me feel like part of something, and that’s why I’m encouraged to tell you this, one of the first things that happened to me after I started working. I’m twenty-six years old, and this is my first real job: administrative assistant, right-hand woman to the owner of the company.

On my first day, they welcomed me almost as warmly as you did. The usual comments started coming in, about how I was the office’s new pretty face, that sort of thing—compliments you’re only half grateful for because you never quite know what to do with them. I smiled, nodded, and got on with my work. I was far too busy learning names, passwords, and where the coffee was kept to stop and think about anything else.

The company isn’t big. There are just a handful of us on a floor full of filing cabinets, plants nobody waters, and a coffee machine that roars like an airplane every morning. They assigned me a desk directly across from the owner’s office, separated only by a frosted-glass partition. From there I could watch him move: a shadow standing up, sitting down, pacing in circles whenever he talked on the phone.

What I did notice, as the days went by, was my boss.

His name is Aurelio, although that isn’t his real name, and he must be around forty-nine or fifty. A serious man with a measured voice, the kind who signs papers without looking up. He always wore a pressed shirt and an antique watch that was slightly too big for him. His temples were silver, and he had strong hands that I found it difficult not to watch when he handed me a file. Big hands, long fingers, the kind you imagine gripping your waist while bending you over a desk.

But every time we were alone in his office, something in him fell apart. He cleared his throat. Rearranged folders that were already in order. Left sentences unfinished and started them again. Once, his voice shook so badly while asking me for a report that he had to look out the window to finish the sentence. I may be many things, but stupid isn’t one of them, and I immediately realized what was happening. He was going through what any man goes through when he has a woman in front of him who gets his blood hot.

And, I’m not going to lie, I started enjoying it. I began lingering an extra minute when I handed him something, leaning over a little when pointing out a figure on the screen so his eyes would drift toward my cleavage, holding his gaze until he was the one who looked away. A couple of times I caught sight of the bulge outlined in his pants when he stood up too quickly from his chair, and I had to bite back a smile. It was a silent game, and we were both playing it without naming it.

One Thursday afternoon, while I was putting away some files, he approached my desk with his hands in his pockets like a teenager.

—Hey—he said, clearing his throat again—would you like to go have a drink when we leave? To… celebrate your first week.

I stared at him for a second longer than necessary. I knew perfectly well what that invitation meant, or at least what he wanted it to mean. I could have said no. I could have made up any excuse. But I’d spent days imagining what it would be like to have him on top of me, what he would sound like moaning, what his face would look like when he came. And I was curious.

—I’d love to—I replied.

***

We left the office with the awkward distance of two people pretending nothing was happening. We walked to a small bar a couple of blocks away, with dim lighting and quiet music, the kind of place where you can talk without shouting. We ordered something to drink, but the truth was we hardly drank at all. We talked much more than we drank.

He asked me about my degree, my plans, my friends. I answered him and returned the questions, curious to see how far he was willing to go. I was surprised to discover that behind the rigid office man was someone shy, almost clumsy, who laughed softly at his own jokes and apologized twice for everything. That fragility, far from boring me, appealed to me. It made me feel in control, as though I would be the one teaching him a thing or two that night, not the other way around.

When I told him, casually, that I wasn’t seeing anyone, I saw his eyes light up. He became even more nervous, if that was possible, and his hand shook a little as he set his glass down on the table. He swirled the ice around in his whiskey a couple of times, searching for something to say, and in the end all he managed was a “Wow” that made me smile. Under the table, I had crossed my legs in a way that had made my skirt ride up more than it should, and he kept stealing glances at them whenever he thought I wasn’t noticing.

That was when I decided it was my turn to move the pieces.

—Shall we play a game?—I suggested. Questions and answers. But honest ones.

He agreed, I think without realizing what he was getting into. We started gently, with silly things, and little by little I turned up the heat. Underwear color. I told him mine was black, lace, without a matching bra because the one I had on showed through my blouse. He choked on his drink. Number of partners. The strangest place where we’d done it. I told him that once I’d been fucked against the door of a nightclub bathroom, with the music pounding, and I watched him swallow. Each answer brought us a little closer across the table, our voices lower, our gazes longer.

—Last one—I said, biting my lip. Your fantasy. The one you’ve never fulfilled.

Aurelio fell silent, weighing whether to tell me or not. In the end he confessed it in a low voice, close to my ear. He said he had always wanted a woman to suck his cock while looking him in the eyes, without holding back, until he came in her mouth, and then to spread her legs for him and ask him to fuck her. He said it haltingly, staring at the table, and when he finished he was red to the tips of his ears. Then he returned the question in a hoarse voice.

—I’ve had one for a while—I admitted, moving closer until he could feel my breath. I’ve always wanted to be with an older man. Someone who knows what he’s doing. Someone who’ll grab me by the hair and use my mouth however he wants, without asking permission.

He said nothing. He began stroking my face with the backs of his fingers, slowly, as if he were afraid of breaking me. He brushed my cheek, the line of my jaw, the edge of my lips. I opened my mouth slightly and sucked the tip of one finger, staring straight at him. A sigh escaped him, and I felt his hand begin to tremble. I let him do it, enjoying how hard he was struggling to contain his desire.

—If you want to find out what I can do with this mouth—I whispered—we’ll have to go somewhere more private.

He asked for the check without taking his eyes off me.

***

We went out into the street, and the cool air didn’t put out a thing. Quite the opposite. We walked pressed close together, his hand brushing mine with every step, still daring neither of us to lace our fingers together, like two teenagers deliberately stretching out the moment before. I could feel my heart in my throat, but not from fear—from that anticipation that’s almost better than what comes afterward. My panties were already soaked just thinking about what I was going to do to him.

We’d left his car parked on a dark side street, with a couple of trees blocking the little light there was. We didn’t get any farther. We were so turned on that it didn’t even occur to us to go somewhere else, or think about a hotel, or his place, or mine. The only thing that mattered was right there, one step away, and neither of us wanted to wait.

He opened the rear door and got in first. The open door acted as a screen, hiding me from the rest of the empty street. I settled between his legs, kneeling on the seat while he reclined, already breathing unevenly. I opened his shirt by a couple of buttons, ran my nails over his chest, and slowly bit his neck. He dropped his head against the backrest and let out a sudden breath.

I unbuttoned his pants without hurrying. I lowered the zipper tooth by tooth so he could hear it, then slipped my hand over his boxers. He was hard as a rock, throbbing, and a damp spot stained the fabric. I squeezed him through the cloth, felt him pulsing against my palm, and he let out a growl that raised goose bumps on my skin. I wanted him to feel every second, wanted the waiting to drive him crazy before anything else.

When I finally pulled down his boxers and took out his cock, it was bigger than I’d imagined. Thick, taut, the tip glistening with pre-cum. My mouth watered. I looked him in the eyes and began stroking him slowly, my hand only loosely closed, moving up and down from the base to the glans, watching his jaw tighten with every motion. I ran my thumb over the tip, spreading the fluid that seeped from it, and he let out a long moan, his eyes half closed.

—Look at me—I told him. Don’t close your eyes.

I gathered a little saliva and let it fall slowly from above, a long strand landing right on the tip. Without breaking eye contact, I spread it with my hand over his entire cock until it was shiny and slippery. I began jerking him off with both hands, one above the other, twisting my wrists, squeezing tightly around the shaft. He let out a deep groan that seemed to come from the very depths of him. He liked watching as much as he liked feeling, and I knew it, so I gave him both.

I finally took him into my mouth, but just as slowly. First I sucked the tip, circling my tongue around the glans, dipping the tip into the opening, savoring the salty taste that kept seeping from him. I slowly worked my way down, just a few inches at a time, sucking and releasing, sucking and releasing, while my hand kept stroking the rest. I wanted him to feel my tongue playing with him, traveling over every inch, like an unhurried massage.

I pulled his cock from my mouth and licked the entire underside, moving up and down along the thick vein pulsing in the middle, my tongue spread wide and flat, as though it were an ice cream. Then I took his balls into my mouth one at a time, sucking them slowly while I kept jerking him off. Aurelio tangled his fingers in my hair, not to hurry me, but to have something to hold on to. He muttered unfinished things, half my name, an occasional word, a “fuck” that escaped him when I ran my tongue right beneath his balls.

I went back up and took him all the way in. Deep. I pressed my nose against his pubic bone and stayed there for a few seconds, my throat squeezing his glans, making him feel every inch. He let out a muffled cry, and his hips lifted off the seat on their own.

—Fuck, fuck—he repeated. Fuck, you suck so good.

The part I always like best comes afterward, when I pick up the pace. I started sucking him fast, all the way down, letting my throat close around him, letting my eyes fill with tears, letting saliva run down my chin and wet his balls. Every time I reached the bottom, I stayed there one second longer, swallowing and squeezing, until that almost-choking sensation that—I don’t know how to explain it—turns me on like very few things can. My panties get wet, my nipples harden, and I end up fucking my own face with his cock.

He hadn’t expected it. His whole body began to shake, and he had to rest his head against the window. He grabbed my hair with both hands, no longer being careful, guiding me and setting the rhythm. I let him. I let him fuck my mouth however he wanted, thrust his hips upward, drive himself deep inside me again and again. I fulfilled the fantasy he’d told me about at the bar without saying a word, and he understood.

—Slowly, slowly—he suddenly pleaded, pulling my hair back—or this is going to be over right now.

So I eased up. I pulled him out and let him rest for a moment against my lips, against my tongue, playing with him on the outside so he could recover his breath and his composure just enough to lose them again. I ran my tongue over the tip, kissed the glans, and started stroking him gently again with a hand full of saliva. Every time I thought he was calming down, I started again. I took him down my throat and stayed there, swallowing, looking him in the eyes with my face full of tears and spit. Then I pulled him out and went back to the little kisses, the soft licks.

I had his cock at my mercy. I could make him come or make him hold out for another ten minutes, and he knew it. He writhed on the seat, shirt rumpled, pants tangled around his knees, moaning softly, begging without actually asking. At one point I slipped a finger between his balls and his ass, pressing that spot that drives men wild while I sucked eagerly on the tip. He almost came off the seat.

—I’m going to come, I’m going to come—he began repeating, no longer able to hold back.

It was quite a spectacle, and we both knew it. The last time, I took a breath, brought him all the way in once more, and sped up without warning. I cupped his balls with one hand, squeezing gently, and with the other I jerked him at the base in time with my mouth. He tried to say something, a warning that never quite formed, and came right there with a long growl born deep in his chest. I felt his cock pulsing inside my mouth, and the first jet struck my throat, hot and thick.

It was obvious he’d gone far too long without anything like it, because he almost overflowed me. Jet after jet, he just kept coming, filling my mouth with cum. I pulled him out only slightly so he could see it, so he could watch his come keep spilling onto my tongue and lips, a strand running down my chin. I kept stroking him slowly, drawing out every last drop, while his entire body shook, his jaw slack and his eyes glassy.

When he finished, I closed my mouth, stared straight at him, and swallowed. All of it. Then I showed him my clean tongue, so there could be no doubt.

I stayed still for a moment, holding his gaze, then slowly straightened up, adjusting my hair as though nothing had just happened. I ran my thumb over the corner of my mouth, gathered what had escaped, and put it back into my mouth. He was still lying there, breathless, with a foolish smile that wouldn’t go away, looking at me as if he’d just witnessed a miracle.

***

What he said afterward was almost as delicious as everything else. He kept repeating that nobody had ever done anything like that to him, that he’d never come so hard in his life, asking where I’d been all his life, saying we had to do it again soon. That next time he wanted to return the favor, that he wanted to eat my pussy until I was shaking, that he wanted to fuck me everywhere. He even ventured to say, half joking and half serious, that there was a very comfortable sofa in his office, and that the door had a lock.

I laughed, straightened the tie he hadn’t even taken off, and gave him a short kiss at the corner of his lips, leaving him with the taste of himself.

—We’ll see—I told him.

That’s how, in my first week at work, I became the boss’s favorite. Not because of the spreadsheets or how quickly I learned the systems, though those helped too, but because of one night neither of us had planned and that we both ended up wanting to repeat.

Since then, whenever he calls me into his office and closes the door, he’s no longer the one who gets nervous. I’m the one who decides how far the afternoon goes—whether I kneel beneath the desk to suck him while he tries to answer the phone, or climb astride him on the sofa and impale myself on his cock until we both bite our lips to keep from screaming.

I hope you enjoyed this confession. Tell me what you thought.