The Tranny My Boss Kept for Himself

I had been working at that distribution company for almost three years when Marcos Fuentes hired me as an executive assistant. He was forty-three, married, with a square jaw and that kind of gaze that makes you hold his eye contact even when you’d rather not. In my first week I learned his coffee, his calendar, and the order in which he preferred his reports. In my second week, he learned something about me I had never thought to show him.

I don’t know exactly when he found out. Maybe it was the Tuesday I dropped my makeup bag in the bathroom and the lipstick and eyeshadow rolled across the floor. Maybe it was when he saw me arrive one Monday with brows too well-groomed for someone who doesn’t spend time on those things. Maybe he simply sensed it from the start, with the kind of attention some men have for spotting what everyone else misses.

Anyway, on a Thursday at seven-thirty in the evening, when the rest of the floor had already emptied out, he knocked on my office door.

—Lock it —he said without looking up from the screen.

I closed it. I stayed standing in front of his desk. He kept reviewing the document for a moment longer, then set his pen on the paper and looked straight at me.

—What’s your name when you’re alone? —he asked.

It took me four seconds to answer. Four seconds in which my heart lurched, in which I weighed the possible exits and decided I wasn’t going to pretend not to understand.

—Valeria —I said.

Marcos nodded slowly, as if that were exactly the answer he expected and not the one he’d expected to surprise him.

—Next Friday you’re staying late. Bring what you need.

That was all. There was no more conversation that night. I gathered my things, said good night, and went down to the street without really knowing what I had just agreed to.

***

The following Friday I arrived at the office with a tote bag I didn’t open all day. I kept it under my desk and spent eight hours answering emails, coordinating deliveries, and updating the week’s route sheet as if it were any ordinary Wednesday. But every time Marcos came out of his office and crossed the room on his way to the printer or the meeting room, I felt the weight of his eyes on the back of my neck for exactly as long as it took him to get away.

At ten past six the last coworker left. At half past six, Marcos went into his office and closed the door without saying anything. I waited ten minutes, staring at the screen without seeing anything. Then I grabbed the bag and went to the floor’s bathroom.

I took my time. The dark brown wig, straight to the shoulders, fitted carefully over the cap. The eyeliner, thin and extended toward the outer corner. The dark red lipstick, the same one I’d been saving for months without really knowing why. The black knit dress, clinging from the shoulders to mid-thigh. The fishnet stockings. The stiletto heels I had kept in the bag since Sunday night.

Before I went out, I stopped in front of the mirror for a moment. Not to evaluate myself. Only to remember who was about to walk down that corridor.

Valeria.

I crossed the empty room without turning on the lights. Only the hallway neon and the light from Marcos’s office seeping out beneath the door. I knocked with one knuckle.

—Come in —he said from inside.

***

He was sitting on the edge of the desk, arms crossed, tie loosened by three fingers. He looked me up and down slowly, without the quick expression people use when they’re assessing something that surprises them. It was the look of someone who’d spent days imagining exactly what was standing in front of him.

—Lock it —he said.

I did. When I turned back, he was already standing and walking toward me. He didn’t rush, but he didn’t stop either. He put a hand on my jaw, lifted my face, and kissed me slowly, mouth open, tongue insistent, pushing into mine without asking permission, as if he’d already asked for it with his eyes for weeks. He smelled like expensive cologne and an eight-hour workday, and that combination was more arousing than anything I had prepared for this moment.

He pressed me against the door. His hands moved down my sides, found my waist, then my hips. When he reached the hem of the dress he paused for a second. With his other hand he grabbed the wig hair at the nape of my neck and pulled just enough to force me to offer him my throat. I felt his teeth on my skin, a dull bite that would leave a mark by the next day and that neither of us was going to mention.

—How long have you been like this? —he asked against my neck.

—As Valeria?

—Yes.

—Since I was eighteen —I said.

He didn’t answer. He kept kissing my neck while he lifted my dress with calm hands. His hands were broad and firm, without any nervousness. When he found the thong over the stockings, he paused for an instant and felt over the fabric what was there. He noticed the hard, contained bulge under the satin, and instead of pulling away, he closed his hand over it. He squeezed slowly, measuring me, and kept going as if it were no revelation at all.

—I knew you’d be hard before you came in —he murmured against my ear—. It shows in the way you cross a room.

I bit my lip. He kept kneading over the thong, his thumb running along the length, not taking my cock out of the fabric yet, deliberately. Every time he reached the tip he’d pause a fraction and slide back down. Beneath the satin I was soaked; the dampness clung and he could tell, and he smiled.

—Look at me —he said.

I looked at him. Without breaking eye contact, he pulled the thong down to mid-thigh. My cock sprang free, rigid against his stomach through his trousers. He took it in his dry hand, no lubricant, squeezing firmly, and began stroking me slowly against the door. The rough palm on my glans made my knees weaken.

—Still —he said, though I wasn’t moving. He said it for what he was about to do next.

He dropped to his knees. Marcos Fuentes, my boss, forty-three, married, knelt in front of me with his trousers still immaculate and took my cock into his mouth in one go, without preamble. I felt the wet heat closing around it, the tongue flattened underneath, the throat opening to swallow me whole. He stayed like that for a few seconds, eyes closed, taking me in. Then he began to pull back slowly, leaving my cock slick with saliva, and went down again. He sucked like someone who had sucked many before, with a rhythm that gave no respite but didn’t rush either.

—Marcos... fuck —I gasped, my hands braced against the door.

He pulled my cock out of his mouth just to speak.

—Shut up. Here Valeria doesn’t speak unless I ask her something.

And he took me back in. One hand held the base and the other squeezed my balls with measured firmness. I couldn’t look away from his head moving between my thighs. When he noticed I was getting too close, he pulled off with a pop and wiped the corner of his mouth with the back of his hand.

—Not yet —he said—. Turn around.

He turned me gently, set me facing his desk, and pressed against my back. I felt the weight of his body, the pressure of his hips against mine. He was hard and not hiding it: his rigid cock pushed through his trousers against the crease of my ass, searching for the gap above my clothes.

—Lean over —he said near my ear.

I braced myself on the desk with my palms open. He lifted my dress to the waist, leaving the stockings and thong exposed. He lowered the thong slowly, leaving it at mid-thigh. Then he spread my cheeks with both hands and stared for a long moment, without touching, letting me feel the cold office air against my exposed ass.

—Hold still.

The first touch was his mouth. I wasn’t expecting it. He knelt and bit the inner part of my thigh, right where the stocking ends and the skin begins. Then he went up with lips and tongue until he reached exactly where he wanted. He started eating my ass with patience and no hurry, like someone who knows what he’s doing and doesn’t need to prove it by speeding up. The hot muscle of his tongue pressing against my hole, slipping in suddenly and pulling back, then insisting again. He worked saliva in and pushed again, deeper each time, until I could feel his tongue opening a path inside me. He put his fingers in my mouth from behind so I’d wet them and I sucked them without lifting my forehead from my forearm.

I rested my forehead on my forearm and closed my eyes.

—Marcos... —I panted.

—Quiet.

He kept eating me for what felt like ten minutes. The tongue went in and out, curled, sucked the edge of my ass with a wet sound that filled the office. Meanwhile, with his free hand he’d taken my cock and was stroking me slowly, not letting me come, measuring me. The edge of the desk was cold against my thighs. The leather chair creaked when he stood. I heard the drawer open and close. The unmistakable click of a tube. Something cold and thick dropped straight onto my ass, and he spread it with his fingers slowly, without roughness, as if he had all the time in the world.

He started with one finger, moving it calmly, waiting for the body to accept it before going on. He wasn’t in a hurry. He was methodical about this the same way he was about everything else, and that turned out to be more reassuring than I would have imagined. The finger went in to the knuckle, paused, twisted, came out shiny. It went back in. I started pushing my ass back without realizing it.

—Breathe —he told me.

I breathed. The second finger went in alongside the first. I felt the slow opening, the burn mixed with a pressure that wasn’t exactly pain but fullness, a word I had never used to describe this before and that suddenly fit. His fingers moved carefully, twisting, spreading, preparing. He curled the tips upward and found that spot all at once, making me let out a louder moan than I meant to. He smiled against my shoulder.

—There it is —he said, and kept touching it with precision, pressing and releasing, while my cock dripped over the desk wood.

—Fuck, fuck —I muttered.

—A third finger —he announced, like someone warning of a schedule change—. Hang on.

The third finger went in with more resistance. It burned for the first few seconds and then the burn turned into heat. He was fucking me with his hand slowly, opening, closing, until my ass gave up completely and started sucking his fingers in.

—Good —he murmured, in the same tone he’d use to review a report that was coming out right.

After a while he pulled his fingers out and added more lubricant. I heard him unbuckle his belt, the sound of the buckle striking leather, the zipper coming down slowly. His breathing had changed, deeper, more contained. At last I felt the hot skin of his bare cock pressing against my ass, thick, hard as stone, sliding up and down along the crease without entering yet, smearing itself with lubricant.

—Tell me if I stop —he said.

—Don’t stop —I answered.

The entry was slow. First the natural resistance of muscle that doesn’t want to give because it still doesn’t fully trust. Then the head opening its way through, that exact moment when the ring gives and lets it pass, the live, precise burn that slowly lessened as he went forward centimeter by centimeter, never pushing more than I could take at each moment. I felt every vein of his cock pressing against my insides.

He stopped when he was halfway in.

—Good? —he asked.

—Yes —I replied, lower than usual—. Put it all the way in.

He kept going. Every new centimeter brought a different sensation, deeper, denser, spreading into my belly and thighs. When he reached the hilt we both stayed still for a moment. Only his breathing and mine filled the office, and the hallway neon slipping in through the crack under the door. His pelvis pressed to my ass, his balls resting against the back of mine.

—All of it —he said, almost to himself—. You swallowed all of it, Valeria.

He started moving. The initial rhythm was slow and deep: he came almost all the way out, leaving only the head inside, and then drove back in with a long, controlled thrust. Every time he bottomed out, the tip hit a spot that sent heat through the rest of my body in slow waves. I braced myself better against the desk and let go. My cock hung heavy between my legs, dripping clear threads that fell to the floor.

The rhythm picked up. Marcos grabbed my hip with one hand and my shoulder with the other for leverage, and started really fucking me. The sounds of our bodies filled the office silence: the dry slap of his pelvis against my ass, his balls bouncing against mine, the wet splash of lubricant, dense and rhythmic, mixing with the rustle of his trousers down around my stockings. I closed my eyes and focused on every detail: temperature, pressure, the weight of him against my back.

—More —I said, without calculating it—. Harder.

He sped up. The desk moved an inch with every thrust. He leaned forward over me, mouth pressed to my ear, and started talking to me for the first time in a filthy voice.

—This is what you wanted from day one, isn’t it? For me to fuck you here, in my office, dressed like this. For me to split your ass open on top of my desk.

—Yes —I gasped—. Yes, Mr. Fuentes.

He liked that. He noticed how I tightened around his cock when I said it, and he drove in harder again.

—Again.

—Yes, Mr. Fuentes... fuck me more.

He smacked my right ass cheek with an open palm, a crack that sounded like a gunshot in the empty office. Then another on the left. My skin burned and I thanked him for each one with a moan I couldn’t hold back.

The lipstick had left a red mark on the sleeve of my suit jacket, and at some point I thought, completely absurdly, that tomorrow I’d have to explain that at the dry cleaner’s. The ridiculousness of the thought made me smile against the cold wood.

Without pulling out of me, he pulled me upright by the wig. I ended up standing with my back against his chest, impaled, while he kept moving his hips up and down with short, deep thrusts. He ran one hand along my neck, not squeezing, just holding, and with the other he grabbed my cock and started jerking me off to the rhythm of his thrusts.

—Come for me —he whispered in my ear—. Don’t touch yourself. Just with my cock and my hand.

The sensation that hit me was different from the other times I’d been like this. It came from inside, from that spot of constant pressure against the prostate, and spread outward in a wave that didn’t announce its arrival. My legs shook. I had to bite my lip to keep from making noise, because even with the door locked and the floor empty, there was a limit to what I could allow myself.

Marcos noticed. I don’t know how, but he noticed. He adjusted the angle slightly, kept squeezing his fist around my cock, and held the exact rhythm, not speeding up or easing off, keeping me right on that edge until control slipped out of my hands. When I came it was without warning and impossible to hold back: one long contraction that made me grip the desk edge with white knuckles and shut my eyes tight while thick ropes of semen snapped between his fingers and splattered over the polished wood, over the report papers, over the pen. My ass clenched around his cock in spasms that drew a low groan out of him.

—Fuck —he muttered against my nape—. Like that, squeeze it like that.

He bent me over the desk again, my cheek pressed to the wood, and fucked me again, now without control, chasing his own finish. The rhythm turned brutal, short, animal. His breathing had become a rough pant right by my ear. I, still sensitive from the orgasm, felt every thrust like a shock.

—Inside —I begged—. Come inside.

He held on for three or four more thrusts. Then he gripped my hips hard with both hands and drove in all the way one last time, pinning me against the desk edge. I felt the heat of his orgasm unloading in slow, thick pulses, the first wave hitting deep, then another, and another, his cock throbbing inside me as it emptied. The pressure of his fingers was going to leave bruises on my hips by the next day. A low, contained sound came out of his throat, almost a moan ground between his teeth. The only one he allowed himself all night.

We stayed still for a moment. His forehead dropped between my shoulder blades. Our breathing settled at the same pace, without either of us deciding it. When he came out, slowly, I felt the hot thread of his semen sliding down the inside of my thigh, mixing with the lubricant, soaking the edge of the fishnet stocking.

***

When he straightened up, I went to the bathroom to clean myself up and pull myself together. He got dressed in silence: belt, shirt, tie knot tightened again. By the time I came back to the office he almost looked like the same man who had arrived at eight in the morning. Only a crumpled paper napkin in the trash and a dark stain in the corner of the report betrayed what had just happened.

He handed me a paper napkin from the drawer.

—The lipstick —he said, pointing to the left corner of my mouth.

I wiped it away. I looked at myself in the dark reflection of the computer screen.

—Does your wife know you’re here? —I asked. It wasn’t an accusation. It was genuine curiosity, the kind you can’t help having after something like that.

—She thinks I have a meeting —he said. Without guilt and without pride. He just said it.

I grabbed the bag and went back to the bathroom to change. The wig into its case. The lipstick into the makeup bag. The dress folded carefully, with the stain at the hem that I’d have to wash by hand at home. Diego again: dark pants, gray sweater, sneakers. The man who showed up every morning with Marcos’s coffee in his hand and the day’s schedule loaded on his phone.

When I came out, he had already turned off his office lights and put on his coat.

—Good work this week —he said as he passed me, in the same tone he’d use to comment on a clean quarter.

We went out into the hall. We waited for the elevator together without speaking. On the ground floor, he turned toward the parking lot and I toward the main exit.

—Wednesday —he said without turning around.

—Wednesday —I repeated.

And that’s how it went for months. Valeria existed only inside that office, only when the blind was down and the door locked. Outside of that, we were boss and assistant, with all the protocol and distance that implies. He never treated me differently in front of the others. He never made me feel more or less. He never used what he knew about me as leverage for anything.

There was something strangely clean about that, despite everything that was absolutely not clean.

Sometimes, when he passed by my desk first thing in the morning to drop off the day’s documents, he brushed my wrist with the tip of his index finger. Just that. A second, without stopping.

—I’ve got a late meeting this afternoon —he’d say.

And I’d answer, without lifting my eyes from the screen:

—All right, Mr. Fuentes. I’ll get your office ready.