I Dressed Like a Girl That Afternoon at Dad’s House

My name is Vale, I’m twenty years old, and for almost a year now I’ve accepted that I’m gender fluid. Physically I’m still slim, with a defined waist, hips that show depending on what I wear, and legs I’ve learned to take care of. Some days I look in the mirror and recognize myself as a boy; other days I put on makeup, slip on stockings, and I’m someone else without ceasing to be me.

The first person to accept it, even before my own mother, was Esteban. He’s Joaco’s father, my best friend since primary school. He’s forty-two, divorced, bisexual, and he’s always been the male figure I never had at home. When I told him what was going on with me, he didn’t even blink. The next day he took me to a shopping mall on the other side of the city, where no one would run into us, and helped me pick out my first batch of girl’s clothes.

That afternoon was strange and beautiful. Esteban looked at things with the casual certainty of someone who knows exactly what he wants: “That cut will suit you,” “No, that shade is too dull for your skin.” I left with four bags and the strange feeling that that man, whom I’d spent my whole life jokingly calling godfather, had looked at me in a different way for the first time.

The months passed. “Godfather” became “dad” in my messages, first as a joke, then not so much. I went to his house to watch series with Joaco and stayed for dinner. Sometimes I showed up as a boy, sometimes as a girl; there was never an awkward comment, from him or anyone else. But one winter Friday, when Esteban hugged me goodbye, his hand slid a little lower than necessary and lingered on the curve of my hip. I said nothing. No need to.

That same night, in my bed, I touched myself thinking about him, squeezing the pillow between my thighs, and decided what I was going to do.

***

The following Saturday, Joaco was at a birthday party out of town. I texted Esteban in the middle of the afternoon: “Can I stop by for a bit? I want to talk to you.” He took two minutes to reply. “Of course, babe, I’ll be waiting.”

I got to his house in a dark blue knee-length dress, flats, and a big bag. Light makeup, hair tied up. I wanted to walk in looking like just another girl and save the rest for later.

Esteban opened the door in sweatpants and a T-shirt. He smelled like freshly applied cologne; I noticed it right away.

“I thought you were coming to pick up Joaco,” he said, letting me in.

“No. I knew he wasn’t here. I came to see you.”

He raised his eyebrows, but didn’t ask anything else. He made me coffee, put on a movie neither of us was watching, and sat with me on the sofa, keeping exactly the distance of a father who watches his boundaries. We talked nonsense for an hour. I nodded and laughed, but inside I was counting the minutes.

“I’m going to get something to nibble on,” he said at one point, and got up toward the kitchen.

It was my turn.

I went into his bedroom, closed the door, and emptied my bag onto the bed. I took out what I’d been saving for months: lace stockings, tiny panties, a semi-sheer baby doll, and a pair of red heels I hadn’t worn yet. I changed with trembling hands. I let my hair down again, touched up my lips, and looked at myself in the wardrobe mirror. The girl looking back at me didn’t look like anyone’s daughter.

“Esteban,” I called from the room, my voice a little broken. “Can you come here for a second?”

I heard his steps in the hallway and my heart jumped up into my throat. The door opened.

He froze in the doorway. His gaze moved down slowly: first the heels, then the stockings, the panties, the lace of the baby doll, and finally my face. He didn’t speak for several seconds.

“Fuck, Vale…” he murmured, his voice rough. “I don’t remember buying you any of that.”

“You didn’t buy it for me,” I answered, trying to smile. “I chose this. For you. Do you like it, dad?”

He nodded without saying anything. He closed the door behind him.

I walked up to him with the new clumsiness of the heels. I took one of his hands and placed it on my waist. I leaned in and kissed his neck, right below the ear, where I knew he had a small mole. I heard him suck in a sharp breath.

“Vale, wait,” he said, grabbing my shoulders and pulling away. “You’re like my son. Like my daughter. What you’re doing…”

“I’m doing it seriously,” I cut him off. “It’s not a game. It’s not an experiment. I’ve been thinking about this for months. Months of jerking off thinking about your cock, dad. If you don’t want this, I’ll get dressed and leave, and we’ll never speak of it again. But I want to know what you want.”

He stayed silent for a long while. Then he looked at me like he’d never looked at me before, not even the day of the bags at the mall. Something inside him broke.

“I want to,” he said. “Fuck, how badly I want to fuck you.”

***

I kissed him first. It was a slow kiss, almost tentative, until he took hold of the back of my neck and turned it into something else. His tongue tasted like coffee and something more. He shoved it all the way into my mouth, searching for me, and I sucked it like I was already sucking him somewhere else. I bit his lower lip. He answered by squeezing my ass with both hands over the baby doll, hiking it up to my waist and slipping one finger between my cheeks over the minimal fabric of my panties.

I slid my hands under his T-shirt and pulled it up. His chest was hard, not gym hard, but the hard of a man who works with his hands, with grayish hair trailing in a line down to his navel. I licked one nipple while I tugged his sweatpants down, and felt his erection already pressing against my hip, thick, hot, pushing at the fabric of his boxers. I ran my hand over it. It was hard as a rock and already leaking; there was a wet patch in the cotton. I squeezed him from top to bottom and he let out a deep groan against my hair.

I knelt without thinking. I yanked his boxers down and found his cock right in front of me, thick, red at the tip, throbbing, with a pronounced vein running up the side. It wasn’t huge; it was proportionate, perfect for a first real time with someone. I ran my tongue along its entire length, from the balls to the tip, very slowly, looking up at him from below. When I reached the glans he shuddered. I closed my lips around the head and licked the pre-cum dripping from it, salty and thick. I heard him let out a contained moan, as if he still wasn’t fully allowing himself to enjoy it.

“Let go, dad,” I whispered, pulling off for a second. “I’m here so you can put it wherever you want.”

And I took him all the way in. Well, almost all the way: I got to halfway and gagged a little. I breathed through my nose, relaxed my throat, and went back down. I worked him slowly. Up and down without hurrying, licking the groove of the glans with the tip of my tongue, taking him as far as I could without gagging and making up the rest with my hand, twisting it over the saliva I was leaving all over the shaft. With my other hand I grabbed his balls and squeezed them carefully, tugging them downward. A “holy fuck, babe” slipped out of him, straight from the gut.

I slobbered all over his cock until it was dripping over his balls. I’d only pull it out of my mouth to lick his balls one by one, take them in, spit on them, and swallow him again. Every now and then I looked up. Esteban watched me with his mouth half-open, one hand braced against the wall and the other in my hair, pushing now without hiding it, sinking me a little deeper with each downward stroke. I let him do it. I wanted him to shove it all the way down, I wanted him to fuck my mouth until my makeup ran with tears.

“Vale, stop,” he said suddenly, tugging my hair back gently. “Stop or this ends before it even starts.”

I smiled. My chin was shiny with saliva and he was already out of breath. I got to my feet and pointed at the nightstand drawer.

“Do you have lube?”

“Yes.”

I went to get it. I turned my back to him, bent down slowly in front of the drawer, and arched my waist so he could see what he needed to see: my ass squeezed into the tiny panties, the lace stockings ending halfway up my thighs, the red heels. I handed him the bottle over my shoulder, not looking at him.

“Now you can take my panties off.”

He pulled them down with both hands, very slowly, dragging them along my thighs and leaving them at my ankles. When he spread my cheeks with his thumbs, another groan escaped him, longer this time. I was wearing a small red plug, which I’d put in before leaving the house, its base matching the heels. Esteban moved it a couple of times with his thumb, pulling it halfway out and then shoving it back in with a thrust, while with the other hand he jerked me off from the front. I’d been hard since I crossed the door, hard and leaking, and feeling his calloused palm wrap around me got me to the edge in three strokes. The first load hit me almost without warning. I held back the cry with my teeth clenched and came over his hand in short bursts, while he kept moving the plug inside me. He brought his sticky fingers to his mouth and sucked them one by one without taking his eyes off me.

“You come so beautifully, babe.”

When he took the plug out, his tongue filled the space in one go. He licked my hole calmly at first, with the tip, circling it, and then he put his whole tongue in, fucking me with it, eating my ass like he’d wanted to for months. I was braced against the dresser, elbows dug into the wood, legs shaking and heels on the verge of giving out. He opened me with two fingers, then three, searching inside me with his fingertips, curling them until he found the spot that made me moan his name. He stayed like that for a long while, eating me out and fingering me at the same time, until I was pushing my ass back toward him, begging for more.

“Dad, please…”

“There, there,” he said suddenly, getting up, his voice sounding even rougher. “Come here.”

***

He sat on the edge of the bed with his cock pointing at the ceiling, shining with lubricant, and made me lower myself onto him. I spread my ass cheeks with both hands and sat down on him very slowly, searching for the angle. The tip opened my ring with a hot sting that ripped a long moan from me, and then I went down centimeter by centimeter, feeling it go all the way in, each inch drawing a different sound from me. I’d ridden my own toy dozens of times, but this was nothing like that. It wasn’t the cold silicone I knew. It was Esteban’s body, his heat, his fingers digging into my hips, his broken breath on my neck, the pulse of his cock throbbing inside me.

When I had him all the way in, his balls pressed against my ass, I froze for a moment, eyes closed, clenching around him to get used to it, feeling every millimeter. He kissed my temple.

“Are you okay?” he whispered.

“Better than okay, dad. You’re breaking me apart.”

I started moving. Slow at first, with short bounces, testing my balance on the heels, letting him slip out halfway only to bury himself in me again in one blow. He stroked my waist, my thighs, my cock bouncing hard against the hem of the baby doll, without urgency. He pinched my nipples through the lace and twisted them until two tears slipped out of pure pleasure. When I sped up, he grabbed me hard and gave me two or three hard thrusts from below that forced me to pause and catch my breath, thrusts that climbed straight to my throat. He did it on purpose. So did I, so I went even faster just to make him do it again, riding him with my hands braced on his chest, letting him see me bounce with my whole body.

“That’s it, babe, that’s it, how tight you are,” he panted beneath me. “That little ass is mine.”

“All yours, dad. Fuck me.”

At some point he turned me without pulling out, until I was facing away from him, sitting on top with my legs spread outward. From that angle he got even deeper, and he could see his cock going in and out below me. He slipped one hand around the front and grabbed me, jerking me off to the rhythm of my riding, while with the other he pulled my hair back to bite my neck.

“I’m getting tired,” I admitted after a while, panting against his cheek, my thighs burning.

“Lie down,” he answered.

I let myself fall back onto the bed, my ass at the edge. Esteban knelt on the floor, grabbed me under the knees, and lifted my legs until my heels rested on his shoulders. He guided his cock with one hand and shoved it in all at once, with a thrust that went all the way to the bottom and tore out a moan from me that was almost a scream. From that angle he got in so deep I lost my voice for several thrusts. He started pounding me, careful no longer, with the wet sound of his balls slapping my ass each time, the bed creaking underneath. My moans went straight into his ear because he’d arched my back to reach my mouth, eating me out while he drove his cock into me to the root.

“Tell me how I’m fucking you,” he demanded against my lips.

“Hard, dad, hard, don’t stop, break me.”

His hands were everywhere: my neck, my nipples through the baby doll, my cock staying hard without needing to be touched, leaking pre-cum over my own belly button. He grabbed it and jerked me off at the same rhythm he was fucking me, thrust and stroke, thrust and stroke, perfectly synchronized. I had never felt so submissive with anyone. It was total surrender, no tricks, with my legs spread in the air and the red heels pointing at the ceiling. Every time I opened my eyes I found him looking at me, jaw clenched, as if he wanted to memorize the whole scene.

“I’m going to finish,” he said suddenly, voice strained, never stopping his thrusts. “I want to do it inside. Fill you up completely. Tell me if you don’t.”

“Inside, dad,” I panted. “All your cum inside me, don’t pull anything out.”

He pushed two more times, hard, all the way in, and stayed buried there, trembling. I felt the hot pounding of his orgasm at the same time as mine, spur after spur filling me from inside. My own orgasm hit me almost by surprise, while he was still coming inside me and still jerking me off, and I soaked the baby doll red with hot spurts that landed on my stomach, on my nipples, one all the way up to my chin. Esteban laughed softly against my neck, bent down to lick my release off my chest, and kissed my jaw, smearing it with my own cum.

“You’re shaking,” he said.

“I know.”

He let himself drop onto the bed beside me, not pulling out yet, and I stayed there for a while feeling him inside me, slowly softening, his semen packed inside by his cock like a plug. He turned me so I could rest against his chest. We stayed like that for several minutes, not talking, listening to our breathing settle back to normal.

“Are you okay?” he asked for the second time that afternoon.

“I’m better than I’ve been in a long time.”

“Me too, babe.”

I reached out and stroked his poorly shaved beard. When he finally pulled away, a thick thread of cum dribbled out of me down my perineum to the sheet, and he pushed it back in with two fingers, shoving it to the bottom, almost without thinking, because he liked it better that way. It didn’t bother me. I liked that he did it. I liked that he licked the sticky fingers afterward and put them in my mouth so I could taste myself too.

***

It’s been three months since that afternoon. I’m still Vale, a girl some days and a boy on others, and Esteban treats me exactly the same both ways. We see each other whenever we can: half-price hotels, stolen afternoons while Joaco is in class, the occasional whole night when he invents a work trip. I don’t want to call him my lover, but he is. I also don’t want to call him my father, though sometimes “dad” still slips out at moments when it shouldn’t.

Joaco suspects his father is seeing someone. He’s mentioned it to me twice. I pretend I don’t know anything, make a few jokes about what kind of woman he imagines for his father, and change the subject. I feel bad about lying to him; I’m not going to pretend otherwise. But I also know what I have with Esteban isn’t hurting anyone and that tomorrow, if I wanted, it could stop existing.

For now, I don’t want it to. And neither does he.

If you’re interested, I’ll tell you more. Thanks for making it this far.