He Saw Me Dressed as a Woman and Didn’t Want to Leave

The apartment has a special kind of silence on Thursday mornings. Mariano, my coworker, had already left for the office, and the street below hadn’t fully woken up yet. That comfortable silence, the kind that exists only when you know no one is going to interrupt you, was exactly what I needed. I wasn’t in a hurry, I had no immediate obligations. And, above all, I had no intention whatsoever of dressing like I did any other day.

I went straight to the wardrobe at the back, to the drawer I only opened when I was alone. That’s where I keep the clothes that make me feel like someone else—or perhaps like the person I really am when no one is watching. I took out the short, tight black dress, made of a fine, stretchy fabric that concealed absolutely nothing. I laid it on the bed and kept searching.

The black stockings, the ones that rose halfway up my thighs and hugged my legs like a second skin. The tiny thong, barely a triangle of lace extending into an ultrathin strap that disappeared between my buttocks, forcing me to walk slowly, conscious of every step, feeling the string sink between my cheeks and brush against my asshole with every movement. The matching bra, with light padding, just enough to outline a gentle curve beneath the fabric.

I dressed unhurriedly, enjoying every gesture. The wig, dark and straight, falling over my shoulders. Then the makeup: foundation, a little blush, my eyes lined with a clean stroke, my lips painted a bright red I liked watching move in the mirror. A red meant to leave a mark on a cock.

I stood in front of the long mirror in the hallway and silently observed myself.

I turned my waist a little.

I slid one hand up my side, feeling the dress give beneath my fingers.

I smiled.

This is how I like seeing myself.

I picked up my phone and started taking a few pictures. I changed poses, looked for the light coming through the window, played with the angles. I was so focused on that little private ritual that I had almost forgotten the rest of the world.

Then the doorbell rang.

The sound shot through my body all at once, like a lash. It took me a full second to remember the appointment: the technician was coming that morning to inspect the boiler. I had written it down days ago, and it had completely slipped my mind.

I stood frozen in the middle of the hallway, my heart racing.

I could change. I had plenty of time. Thirty seconds to take off the dress, remove the wig, put on some jeans, and open the door like any other man waiting for the boiler technician.

I didn’t.

I looked at myself in the mirror one last time, took a deep breath, and walked toward the entrance, my heels marking every step across the parquet floor. The decision had already been made before my mind had finished thinking it through.

I opened the door.

He was there. Tall, broad-shouldered, with the large, calloused hands of someone who worked with them every day. Work clothes, a toolbox in one hand. He lifted his gaze from the paper he had been looking at and stared at me for a moment longer than usual. Just a moment. But long enough for me to notice—and to notice, too, how the bulge in his trousers was beginning to show.

“Good morning,” he said at last, pulling himself together. “I’m here about the boiler.”

“Yes… come in,” I replied, moving aside just enough to let him pass.

He entered, and I felt his gaze travel over me from head to toe without shame, but without mockery either. There was no contempt in his eyes. There was something else, something hotter, something he didn’t bother to hide. I was looking at his package as he passed, and he knew it.

“It’s in the kitchen,” I said. “This way.”

I walked ahead of him down the hallway, conscious of every inch of my body. Conscious of the way the dress clung to my ass with every step, the way the stockings tightened over the muscles of my legs, the way the heels changed my posture and forced my hips to sway from side to side. I could feel his eyes fixed on me. I didn’t need to turn around to know it. I was showing him my ass, and I liked it.

***

We reached the kitchen. I bent down to open the cabinet beneath the counter, where the boiler was, and let the dress ride up slightly as I crouched. I noticed him stop behind me, far too close to be casual, his eyes fixed on the outline the thong made beneath the fabric, on the thin strip buried between my buttocks, and on the piece of bare skin showing above the stockings.

“It’s here,” I said, slowly straightening up, brushing my ass against his bulge as I rose. I felt his hard cock perfectly beneath his work trousers. He didn’t move away.

“I see…” he replied, his voice dropping a tone and becoming deeper.

He knelt in front of the cabinet and began working. I leaned against the counter beside him, arms crossed, watching him without disguising it. I slowly crossed my legs, one over the other, letting my skirt rise just a little higher, enough for the exact line between the stocking, the bare skin of my thigh, and the hem of the dress to be visible. Beneath the thong, my cock was beginning to wake up too, pressed against the lace.

I felt the lingerie tight against my body, the thong stretching over my balls, the bra outlining my chest beneath the thin fabric. The silence in the kitchen had grown dense. He pretended to concentrate on the pipes, but every few seconds his gaze strayed toward my legs, then to my crotch, then to my painted mouth.

A long minute passed. Two.

Then he spoke without taking his eyes off the boiler.

“Do you always dress like that at home?”

The question hung in the air. I turned toward him very slowly and held his gaze when he raised his head.

“Only when I’m alone,” I replied.

His eyes dropped again, without hiding it this time, traveling over my legs, the dress, the cleavage, then rising again until they met mine.

“It looks very good on you,” he said, standing up until he was facing me. “The clothes… and the way you wear them. Just looking at you makes a guy hard, fuck.”

The air changed completely. Something had broken, or perhaps something had opened.

I didn’t move away. On the contrary, I shifted my weight onto one hip, making the dress cling even more tightly, making every curve stand out further. I lowered my eyes to his fly without the slightest attempt at concealment. His cock showed clearly, pointing to one side, swollen beneath the rough fabric.

“I like seeing myself this way,” I replied softly, almost in a murmur. “And I like what’s getting hard while you look at me.”

“Does it bother you when I look at you?” he asked. He was very close now. I could smell the clean sweat of work, feel the heat radiating from his body.

“No,” I said, keeping my eyes fixed on his. “I like it. It really turns me on.”

The silence stretched between us like a taut rope. He was breathing harder. So was I. Neither of us moved, as though the first one to do so would break the spell.

It was me.

I reached out and placed my hand directly over the bulge in his trousers. I squeezed his cock through the fabric and felt his whole body shudder. He was rock-hard. I felt him from top to bottom, measuring it with my fingers while holding his gaze.

“Come here,” I said, almost in a whisper. “I want to suck it.”

***

I moved away from the counter and walked toward the bedroom without looking back. There was no need. I heard his heavy footsteps following me down the hallway, the sound of the toolbox being abandoned in the kitchen.

I entered the room, left the door ajar behind me, and knelt at the edge of the bed on the carpet, my heels spread apart and my ass resting on my heels. He stopped directly in front of me, so close that his fly was level with my mouth.

I said nothing. I unbuckled his belt, lowered the zipper, and yanked his trousers down to his ankles in one pull. His briefs stretched over the erection pushing against them from within. I pulled those down too, and his cock sprang out, almost striking me in the face: thick, long, its veins swollen from base to the shining glans, already covered with a thick drop. Beneath it hung two heavy, taut balls.

I spent a few seconds looking at it, lips parted, admiring the cock he had a handspan from my mouth. I gripped it with my right hand, barely able to encircle it with my fingers, and stroked it slowly. The drop hanging from the glans fell onto my tongue, salty.

“Fuck…” he murmured above me.

I opened my mouth and took it all in, or as much of it as I could. The glans struck the roof of my mouth and descended, seeking my throat. I closed my red-painted lips around the shaft and began to suck, moving my head up and down at a slow pace, marking each pass with my tongue. I felt the lipstick leaving red rings all along the length of his cock, marking it, smearing it. Every time I reached the base, I held it there for a moment, swallowing saliva against his skin, letting my eyes fill with tears before pulling back.

He grabbed my wig with one hand, without tearing it off, holding it against my skull, and began setting the pace. He pushed my head down to the base, forcing me to swallow his entire cock, and pulled it out when I had no air left. I spat it out, shining with saliva, and licked it again from balls to tip, flattening my tongue against it, looking up at him with mascara-streaked, tearful eyes.

“That’s it, pretty girl,” he panted. “Look at how you suck it. What a little mouth.”

I sucked his balls one by one, taking them into my mouth while continuing to jerk him off slowly with my hand. Then I returned to his cock, closed my lips around the glans, and pressed my tongue just beneath it, against the frenulum. He let out a hoarse moan and pulled my hair backward.

“Wait, wait,” he said, his voice unraveling. “Not like that. Not yet.”

***

He made me stand, and I remained in front of him with my lips smeared and a strand of saliva hanging from my chin. His hands settled on my hips, moved up my waist, felt the fine fabric of the dress, and searched for the hem.

“I want to see you,” he said hoarsely. “All of you.”

He lifted the fabric inch by inch, revealing my thigh and hip until the tiny thong came into view, perfectly tight, outlining the bulge of my hard cock and balls pressed against the lace. He swallowed. I lifted myself slightly to help him, and he let the dress pass over my head and arms until he had removed it completely. He dropped it on the floor without looking at it.

His fingers searched for the bra clasp on my back. He undid it carefully, almost clumsily, and moved it aside. He stroked my nipples with the tips of his thumbs until they were hard as stones.

“Not the thong,” he added, looking me over. “Don’t take it off. You’re perfect like that.”

The stockings were still in place. So were the heels. Just the tight thong, my cock sticking out to one side above the lace, the stockings reaching halfway up my thighs, and the heels—and he was looking at me as though I were the most desirable thing he had seen in a long time.

He gently pushed me by the shoulders until I was lying on my back on the bed, my legs hanging over the edge. He drew my knees up against my chest, bent, and pulled my thong sharply to one side, leaving my asshole exposed before him. He licked two fingers and ran them over my hole, pressing against the knot, circling it until I felt the muscle yield and one finger sink in to the knuckles.

“What a cute little ass,” he murmured, moving his finger inside me. “And so tight.”

He inserted a second finger. It burned, but it was the good kind of burn, the one that opens you up. He scissored them, stretching me, until I began pushing against his hand with my hips, seeking more. He withdrew his fingers, spat into his palm, and coated his cock from top to bottom, stroking it a couple of times in front of me.

He pulled off his shirt in one motion, revealing a broad torso shaped by physical labor, with a trail of hair descending from his navel. He positioned himself between my legs, gripped his cock at the base, and pressed the glans against my asshole, pushing firmly.

“You don’t know what you do to me,” he whispered. “You’ve got me so hard I’m about to burst.”

***

I closed my eyes for a moment and drew a deep breath. I felt his knees spread mine a little farther, his body searching for the exact place between my legs. His cock pressed against my asshole, slipping at first, then finding the center and sinking in. The glans breached the ring with an electric sting that shot up my spine. He kissed my neck, slowly at first, almost restrained, holding himself back as if he wanted to memorize every second.

He eased it in little by little, inch by inch. I gripped his shoulders, digging my nails in, breathing through my teeth as he opened me from within. I felt every vein of his cock dragging against the walls of my ass. There was a moment of tension, of almost unbearable pressure when I swore it wasn’t going to fit, and then surrender: my body yielding and taking him all the way until I felt his balls striking against my ass.

“All the way in,” he panted against my ear. “I’ve put it all inside you.”

“Fuck me,” I begged, my voice broken. “Fuck me hard. Don’t hold back.”

The tenderness lasted barely a breath.

Then everything else arrived: the force, the determined thrusting of someone no longer holding back, his hands squeezing my hips to keep me in place. He pulled his cock almost all the way out and drove it back in with one hard, dry thrust that tore a cry from me. And again. And again. He fucked me with an intensity that knocked the air from my chest, each thrust deeper than the last, his balls slapping against my buttocks with a wet smack.

He grabbed my ankles, spread my legs completely, and pushed them back until my heels nearly touched my ears. My cock was hard, bouncing against my stomach with every thrust, already leaking a thick thread from the glans to my navel. He looked down at me, face dirty, mouth open, watching his cock slide in and out of my asshole.

“Look at how your ass swallows it,” he panted. “Look at how it opens for me.”

The bed slammed against the wall in a brutal rhythm. I moaned without recognizing my own voice, still wearing my heels, my stockings slipping slightly, my wig coming loose against the pillow. The thong was pulled to one side, bunched against my thigh.

He turned me over without pulling all the way out, pushed me facedown, and positioned me on all fours at the edge of the bed. He stood behind me, grabbed my hips, and shoved it back in to the hilt. From that angle it went even deeper. Every thrust tore a high moan from me. He smacked my ass once, hard, then again, marking my skin.

“What an ass you’ve got,” he growled. “What a little slut you are.”

He reached underneath and began masturbating my cock in time with his thrusts. His rough work-worn hand moved up and down my cock while his own cock opened my ass from behind. I lasted four strokes. I came with a long spasm, shooting thick jets of semen onto the sheet that left my stomach trembling, my ass squeezing his cock inside me as I shuddered.

“Fuck, the way you tighten when you come,” he panted. “Now it’s my turn. I can’t take it anymore.”

I felt his body begin to tense, his rhythm becoming more erratic, more urgent. He dug his fingers into my hips, leaving their marks. His back arched, the muscles in his arms hardened. With a deep, hoarse grunt, he came inside me, emptying everything he had been holding back in long, hot spasms that I felt perfectly against the walls of my ass. He collapsed over my back for a moment, breathing raggedly, leaving his cock inside me, still pulsing.

We stayed like that for a few seconds, both panting, sweat mingling, his weight pressing me down in a way that didn’t bother me at all. I felt his cock slowly shrinking inside my ass.

Then he pulled away slowly. He withdrew it with a wet sound, and I felt a warm stream of semen run down the inside of my thigh, soaking the edge of my stocking.

***

He dressed without hurrying, gathering his clothes from the floor, a half-smile on his lips that I couldn’t quite interpret. He said nothing when he left the bedroom. I heard his footsteps in the hallway, the sound of him picking up the toolbox in the kitchen, and finally the front door closing with a sharp bang.

I stayed stretched out facedown on the bed, alone, still wearing my stockings, my heels still on my feet, my thong pulled to one side and my ass still open, his semen dripping onto the sheet. My body continued to tremble, caught between the excitement still pulsing beneath my skin and a slight disappointment at how quickly it had all ended.

I stared at the ceiling for a long while, catching my breath, feeling my heart gradually return to normal, feeling the semen continue to trickle slowly between my buttocks.

And as I did, I knew one thing with absolute clarity.

That morning would never fade from my memory. The way he had looked at me at the door, without disgust, without questions, only desire. The way he had said I was perfect like that. The way his cock had found my ass as if he had known beforehand that I would want it.

Maybe I would never see him again. Maybe the boiler wouldn’t break down for years. It didn’t matter.

That morning I had opened the door dressed as a woman, and someone had looked at me, stayed, and fucked me the way I had wanted to be fucked for years.

And that… was enough.