A Trans Woman, a Day Off, and the Perfect Stranger

I’m Valentina, and I’m delighted to greet you. I hope this story keeps you company for a good while, because it took me an entire morning to live it.

It was a Tuesday in October, just a few weeks ago. I had accumulated days off at work and decided to take one just for myself: no obligations, no schedules, no constant pressure weighing down the day-to-day. Just me, my apartment, and the desire to enjoy myself without anyone rushing me.

The night before, I had gone to bed in sleepwear I adore: a burgundy silk baby doll, matching lace panties, and a metal plug I’ve been using regularly for a while now. I got into bed dressed like that, with the plug snug in my ass, and fell asleep with that familiar feeling of having it inside me, tight and comfortable, as if it were part of me.

I dreamed I was taking my car in to have the tires changed. In the dream, the shop owner looked me over brazenly from the moment I walked in: first sideways, then openly. He invited me to wait in his office, closed the door, and without saying much, started touching me. He kissed my neck, ripped the buttons off my blouse, sucked my tits until my nipples were hard as stone. He slipped his hand under my skirt, pushed aside my panties, and sank two fingers into my already wet cunt. I clenched around the plug with every movement and felt it deeper, more present, while he finger-fucked me against his desk. I came twice before the alarm went off, and in the dream I even managed to feel him pulling down my pants and sliding his cock into me from behind while I pressed my face to the glass.

I woke up completely soaked, my cunt throbbing and the plug still firm between my cheeks. My panties were stuck to my sex from the dampness. I put my hand down there before I even lifted my head from the pillow: two fingers went in without resistance, three when I wanted more. I touched myself slowly, feeling how the plug shifted inside my ass with every breath. I came again, short and clean, biting my lip. Nothing unusual. What was extraordinary was that it was nine in the morning and I had absolutely nothing to do.

I had a light breakfast—coffee and toast with butter—without removing the plug for a single moment. I like that sense of continuity, carrying that secret while I do completely ordinary things. Washing the plate, folding the napkin, opening the window. Pleasure as the backdrop to the everyday.

***

When I finished breakfast, I got the bath ready. Before getting into the tub, I laid out the clothes I would wear that day and arranged them on the bed with a certain ceremony: a black lace bra, matching panties, black fishnet stockings, a white blouse in a loose fabric that leaves the shoulders bare, and an A-line skirt that falls just to my knees. Low heels for comfort. My usual costume jewelry on the vanity.

Every time I set a garment on the bed, I squeezed my ass around the plug hard. Just for the pleasure of feeling it sink a little deeper.

I got into the tub with my underwear on, something I love doing. The hot water, the lace pressed to my body, the familiar weight of the plug between my cheeks... there’s something about that combination that gets me hotter than any coffee. I spent almost an hour soaking, moving, playing under the water. I slid my panties to one side and ran two fingers over my cunt, slowly at first, then with more rhythm, feeling how the hot water opened me wider. With my other hand I squeezed one tit over the wet lace until my nipple stood out hard against the fabric.

At some point I removed the plug—slowly, feeling how my ass was left begging for something—and replaced it with a thicker dildo I keep stored for occasions like this. I coated it with a little of the oil I keep at the edge of the tub and slid it in all at once, all of it, until the base bumped against my cheeks. Goosebumps rose over my skin from head to toe. I started moving it myself, pulling it almost all the way out and driving it in again, while with the fingers of my other hand I rubbed my clit in tight circles. I came with water splashing against my tits, mouth open and silent, squeezing the dildo inside my ass as if I never wanted to let it go. I got out of the tub after that supposedly satisfied treat.

Supposedly was the right word. Because ten minutes later my cunt was already asking again.

I got dressed slowly. Cream all over my body, especially my tits and the inside of my thighs. Underwear. Stockings. Makeup: soft contour, dark shadow on the eyelids, lips in a deep red that leaves a mark anywhere they touch. The wig I chose was brown, bob-cut, which frames my face well and gives me a look that’s somewhere between serious and complicit, which I like a lot.

The last thing was putting in another dildo—this time I chose the longest one in the collection—in my cunt, just for the pleasure of starting the day with that detail. I slid it in standing up, braced against the vanity, and stayed there for a moment feeling it touch bottom. Then I pulled my panties up over it so it wouldn’t slip out and stood looking at myself in the full-length mirror. The blouse, the skirt, the stockings, the red lips, and the bulge barely visible under the snug fabric of my panties. I thought I looked pretty good.

I poured myself a glass of white wine. It was my day off and I deserved it.

***

Close to noon I went to check that everything was in order. I got to the front door, opened it to let in some air, and leaned out toward the street with the glass in my hand. With every step I took, the dildo shifted inside my cunt and forced me to clamp my legs together to hold back a little spasm.

About fifty meters away, a man was working on the facade of a building: sanding or painting something, I couldn’t quite tell. He was wearing work pants and a T-shirt. Slim, with short dark hair, maybe around forty. He wasn’t catalog handsome, but he had a physical presence you could feel even from that distance.

The problem was that I looked at him and couldn’t stop.

With the wine in my hand and the dildo firmly inside me, I stepped a little farther out into the street. I stood where I was visible enough that, if he looked up, he’d see me. I crossed my arms so my tits stood out under the blouse, pushed upward until the neckline showed more than it should have. I looked at him without hiding it.

He looked up.

Our eyes met for a second. I smiled. I didn’t look away.

He went still for a moment, let go of the tool in his hand, and kept looking at me. I took advantage of that to touch my neck with one hand and slide it slowly downward, brushing my cleavage, gliding over the fabric to cup one breast and squeeze it just a little. There was nothing subtle about it. I didn’t want there to be. From there I could feel how the dildo pressed against a spot that made me breathe harder.

He smiled: a brief, slightly nervous smile. He lifted a hand in a vague gesture, as if greeting me. I tilted my head toward the door, inviting him in. He gently shook his head, still smiling, and went back to work.

It made me laugh. And also a little frustrated, truth be told. I went back inside to pour myself more wine and clench my legs for a while until it passed.

I spent the next half hour standing in the doorway, watching people go by. It was noon and there wasn’t much traffic. Some men glanced sideways as they walked, but none of them stopped. I wasn’t insisting on anyone in particular. It was a game, not a need. Though, being completely honest with myself, with my cunt wet around the dildo and my tits hard against the lace, it was also very much a need.

***

Around two in the afternoon, the one who did stop passed by.

Sportswear: gray pants and a sleeveless shirt. Forty-something, short hair with a little gray at the temples, an athletic build like someone who works his body consistently but without obsession. He walked alone, calm, unhurried. When he got close, he turned his head and looked directly at me. His eyes dropped to my cleavage without the slightest hesitation and came back to mine with a calm that I liked immediately.

—Can I help you with something, ma’am?

Being called “ma’am” put me in a good mood instantly. I held his gaze.

—That depends —I said—. What are you good at?

He didn’t blink.

—Quite a few things —he answered, and his tone wasn’t joking.

—I like that —I said—. A lot.

He came two steps closer. I looked him over slowly, without hiding it. I lingered a second too long at the bulge in his workout pants, where a shape was already starting to show that hadn’t been there at the beginning of the conversation. He did the same with me. There was no urgency in either of us, only a calm appraisal that ended in the same place for both of us.

—Is there something specific you need?

—Yes —I said—. Come inside and I’ll tell you.

***

I closed the door behind us. He stood in the entry hall, looking at the apartment and then at me. He didn’t seem nervous. I liked that even more.

—What’s the emergency? —he asked.

—I’ve spent the whole day wanting someone to fuck me properly —I said, walking toward him—. Does that count?

He didn’t answer with words. When I reached him, he was the one who leaned toward me. His lips met mine with a confidence I hadn’t expected. It wasn’t a tentative kiss; it was one that started soft and was something else ten seconds later. More pressure. More intent. He pushed his tongue deep, searching for mine, sucking my lower lip between his as if he already knew how the afternoon was going to end.

I took him by the nape. He put his hands on my waist and pulled me closer. We kissed standing there, in the hallway, for several minutes. He nipped my lower lip gently. I answered by pressing harder against him and running my hands over his chest, down until I brushed his crotch over his pants. He was already hard and it bulged, long, against the fabric. I squeezed him with my open palm and he let out a breath against my mouth.

—What’s your name? —I asked when we parted for air.

—Marcos —he said.

—Valentina —I replied.

—A pleasure, Valentina —he said, and kissed me again while he lifted my skirt with one hand and touched my thigh over the fishnet stocking.

***

I led him toward the inner patio, where there’s a grassy area that gets sun at that hour. We sat on the grass. He took off his shirt without me asking. He had a defined, brown torso, with a small scar on the left side that I found interesting. I wondered where it came from and decided it didn’t matter.

I laid him on his back and climbed on top of him. We kept kissing: slowly at first, then with more pressure, more tongue, more contact. His hands explored my shoulders, my back, the curve of my hips under the skirt. He unbuttoned my blouse without stopping the kiss and opened it to the sides. He pulled one cup of my bra down and sucked my nipple, first with a flat tongue, then harder, biting just a little. I arched against his mouth. With the other hand he squeezed my other tit over the lace.

I dropped my hand to his pants and found him already very hard, throbbing against my palm. I squeezed him leisurely, measuring. He was long. I noticed that right away. And thick too. Perfect.

I lowered his pants enough to free him. His cock sprang out, swollen, the veins marked underneath and the tip already slightly wet with a clear bead that slid down to his stomach. I ran my hand slowly from base to tip and back again, spreading that moisture over all the taut skin. With my thumb I rubbed his glans in circles, feeling it contract.

—You’re very generous, Marcos —I said.

—It’s yours if you want it —he replied, his voice already rougher.

He slid his hand under my skirt. He moved slowly up my thigh until he reached my panties, and a little farther still, until he found what was there. He went still for a moment when his fingers bumped against the base of the dildo buried in my cunt.

—There’s a surprise —he said.

—Problem? —I asked, not moving.

—None —he said. And instead of pulling away, he pressed the base with two fingers, pushing it a little deeper into me. A short moan escaped me against his neck. He smiled and kept playing, pulling it out a centimeter, pushing it back in, moving it inside me while he kissed my neck and sucked on my earlobe.

—Keep going —I asked—. Don’t stop.

—I’m going to do more than that —he said softly into my ear.

I moved down his neck, his chest, his stomach, kissing and licking every part of the way with calm attention. I ran my tongue around his navel. I bit the skin of his lower belly. When I got to the level of his sex, I took his hands and squeezed his fingers before dragging my tongue over the tip, tasting the salty bead he had waiting there.

I grabbed his cock with both hands and ran my tongue from base to tip, slowly, never taking my eyes off him. Then I did it the other way around. I sucked his balls, one first and then the other, taking them into my mouth carefully. He let out a sharp breath and put his hand behind my neck without pushing.

I did it slowly, without haste: learning the texture, the temperature, how he responded when I pressed harder or eased back. Then I took him gradually into my mouth, all the way to the base, and kept steady pressure. I felt him hit the back of my throat and stayed there, swallowing around it, until I needed air. When I pulled back, a strand of saliva hung from my mouth to his tip. I smiled and took him back in, this time in rhythm, moving my head up and down, letting my mouth fill completely with each thrust.

Marcos rested a hand on my head. He didn’t push. He just left it there, feeling the movement, barely marking the rhythm with his fingers in my hair.

—God —he said softly—. I can’t believe it. You suck cock so well.

I answered with a muffled moan, my mouth still full. I ran my tongue around his glans every time I came up and he let out a broken gasp. I slid my right hand between my legs and started moving the dildo inside my cunt to the same rhythm as I sucked his cock: in, out, in. I felt my clit throb like a second heart.

I kept at it for quite a while. He made low, restrained sounds, like someone who is getting exactly what he wants and doesn’t want it to stop. When I felt he was very close to finishing, when I could already tell he was swelling even more against my tongue, I stopped and released him with a wet sound.

—Not yet —I told him—. Don’t come like that.

—No?

—I want more. I want to feel it inside when you cum.

***

I asked him to undress me. He did it carefully: the blouse first, then the skirt. I asked him to leave my stockings and bra on and only lower my panties. He did it without asking anything, sliding them down my legs with both hands, and in the process he moved his mouth over the inside of my thighs, climbing upward, licking, leaving wet kisses until he was dangerously close to my cunt.

I pulled the dildo out calmly—it came free with a wet sound that made both of us look at each other—and left it on the grass, shining and dripping. Marcos looked at it for a second and said nothing. I liked that about him.

He lowered his head without warning and drove his tongue straight into my cunt. I gasped, sharp, and grabbed the grass. He licked my lips first, patiently, then moved up to my clit and stayed there, circling with the tip of his tongue, slipping two fingers into me at the same time. I arched like a bow. I came like that, with his mouth pressed to my cunt and his fingers going in and out, soaking his face. He didn’t pull away until I stopped trembling.

—Fuck me —I said when I could speak again—. I need to feel you inside. Now.

He laid me on my back. He lifted my legs and rested them on his shoulders. He took his cock in his hand, ran it along the lips of my cunt from top to bottom, coating the tip with my wetness, and then lined himself up carefully. He entered slowly: the tip first, a pause, then more, a little more, until all of him was inside. I felt every centimeter. He stretched me in a way that made me claw at the grass with my hands while I felt him reach places no one had reached in a good long while.

When he was fully inside, he stayed still for a moment and looked at me.

—Good? —he asked.

—Perfect —I said—. Now move. Hard.

He started slowly and found his rhythm. I felt him all the way through, deep, with every movement becoming more present. He stroked my tits with one hand, squeezing them, pinching my nipples, and held my hip with the other to control the angle. I pushed him deeper with my legs every time he withdrew, not letting him come out too far. The sound of skin slapping skin mixed with my moans and his heavy breathing.

—Harder —I asked—. Don’t treat me gently.

He grabbed both my hips and started fucking me in earnest. He came out almost all the way and drove back in with one stroke, all the way to the bottom, each thrust pulling a louder moan from me. He leaned forward until he folded me nearly in half, my knees against my chest, and from that angle he reached even deeper. I felt the tip of his cock slam into some internal spot that made me see white.

I came the first time about twenty minutes in, with a sound I couldn’t control, squeezing my clit with two fingers while he kept hammering into me. My whole cunt contracted around his cock and he gave a low groan, clenching his teeth.

—That’s it —he said—. Squeeze like that.

He kept going without missing a beat, fucking me for several more minutes I didn’t even count, sweat dripping from his chest onto my belly.

—Turn over —he said.

He turned me carefully, without pulling out, so I ended up on top. I sat on him, his cock buried to the hilt, and started to move: up and down, finding the angle that let me feel him deepest. I braced my hands on his chest for support and rode him at my own pace, letting his cock nearly slide all the way out before dropping back down on it in a single hard motion. Marcos held my hips with both hands from below and set the rhythm, helping me fall harder. I closed my eyes under the October sun and let myself go.

I leaned forward so he could suck my tits. When his mouth caught one nipple and started licking it, I came again, moving faster, trembling on top of him. I bit his shoulder so I wouldn’t scream too loud.

—I’m going to cum —he said after a while, his voice broken—. I can’t hold it anymore.

—Inside —I asked, without stopping—. I want to feel it inside. Fill me up.

He dug his fingers into my hips, drove into me three, four times from below with all his strength, and I felt him contract first, then let go. Warmth flooded all through me, shot after shot, while he gave a long, deep groan. He kept my hips pinned to his while he finished, staying as deep as he could. I kept moving slowly until his contractions eased one by one, feeling the semen start to leak around his cock and slide down my thigh.

I stayed seated on top of him a little longer, not wanting to move, squeezing my cunt around him as if I wanted to keep him inside. When I finally got up, I felt it dripping hot between my legs.

***

We lay on the grass for a while I didn’t measure. He stroked my arm. I looked at the sky, that clean blue that only shows up in October when the sun no longer burns but still warms. I felt the semen slowly running down my thigh and didn’t do anything to wipe it away.

—Do you have somewhere you need to be? —I asked.

—In a little while, yes —he said—. But not yet.

—Good —I said—. Because I still have some emergencies left.

He laughed. It was a calm laugh, unforced, from someone who doesn’t feel the need to prove anything.

—How many emergencies exactly?

—Enough so you don’t leave yet —I said, and put my hand over his cock, still wet and halfway softening, squeezing it just a little—. Come in? I’ve got a bed inside. And something else for your ass, if you’re up for it.

I felt him starting to harden again in my hand.

—I’m up for it —he said.

He offered me his hand to help me get up. He put an arm around my waist as we walked toward the door, with semen still sliding inside my thigh. Before going in, he turned me toward him and kissed me once more, this time without hurry and without an agenda, like someone who has all the time in the world. He squeezed my ass with both hands under my skirt.

—You know what? —he said against my mouth.

—What?

—I came out for a walk and completely forgot the way.

—Even better —I said—. Come in.

And he came in.