The Delivery Guy Who Made My Tranny Fantasy Come True

My name is Daniela, though that’s not the name on my ID. I’m twenty-seven and I live alone in a quiet gated community on the outskirts of the city, where nobody knows me and nobody asks questions. I’m a trans girl in the closet: by day I work, I greet the neighbors, and I answer to a name that doesn’t feel like mine; by night, with the door closed, I am who I really am.

I have a small body, cinnamon-colored skin, and legs I like to look at in the mirror when I get dressed up. And I have a weakness I’ve carried forever: mature men, the kind who are over forty-five and no longer need to prove anything. I like their calm, the way they look without pretending otherwise, and above all I like imagining how they’d fuck me without asking permission, with the quiet authority of someone who already knows exactly what he’s doing with a hard cock in his hands.

For years I carried the same fantasy, repeated so many times it already had a script of its own. A man would knock on my door not knowing what he was going to find, and when he saw me like that, dressed and made up, he’d make me his without asking. He’d spread my legs against the wall, shove his cock in to the hilt, and make me swallow every drop of his load. I’d imagined it a thousand different ways. What I didn’t expect was for it to become real one rainy afternoon.

***

That day I got home from work exhausted and tense all over. The first thing I did was get under the shower and let the hot water loosen my shoulders. While I was soaping myself up, I already felt that familiar tickle in my stomach, the anticipation of transforming. I ran my sudsy fingers between my ass cheeks, stroked my ass slowly, slipped in one finger just to test myself, and noticed I was already wet with need. When I got out, the mirror was fogged up and I was already someone else.

I took my time. First the clothes: a black thong that barely covered me and, over it, a white chiffon baby doll that left everything it covered to the imagination. Then the stockings, sweet perfume behind my ears and on my wrists, the wig with its glossy black hair falling over my shoulders. I sat down at the vanity and did my makeup slowly, lining my eyes, painting my lips the same red as the platform heels I’d left ready beside the bed. A red made to leave a mark around a cock.

When I was done, I looked myself over in the full-length mirror. Finally I’m me. But that night, looking wasn’t enough. I wanted someone else to look at me, someone to touch me, someone to fuck me.

Outside, rain had started to fall, one of those fine, steady rains that empties the streets. I sat on the bed with my phone in my hand and, before I could talk myself out of it, opened the pharmacy app. I placed a small order, almost an excuse: flavored condoms and lubricant. Anything, so long as somebody would touch my door.

I confirmed the order and my heart kicked into overdrive. There was no going back now.

***

The next forty minutes were a delicious torture. I walked from the living room to the bedroom a dozen times, touched up my lipstick twice, looked at myself in every surface that reflected anything. Every motor that passed in the street made me hold my breath. I told myself it was madness, that I could cancel at any moment, and at the same time I didn’t want anything to happen except exactly this.

Then I heard it: the short honk of a motorcycle in front of the gate.

The problem was getting to the entrance. The community has a shared gate and I couldn’t cross it dressed like that. I cursed under my breath, took off my heels, put on sneakers and an oversized sweatshirt that covered me down to the thighs, and went out into the rain with the umbrella in my hand.

The delivery guy was standing under the eaves, shaking water off his jacket. He was older than I’d expected, and better than I’d expected: maybe fifty, salt-and-pepper hair, large hands, a short beard flecked with gray. He had the calm gaze of men who’ve already lived enough, and a pronounced bulge under his wet pants that I couldn’t stop looking at.

—Daniela? —he asked, checking the bag.

—That’s me —I said, and my voice came out softer than I’d intended—. It’s raining like hell. Come onto the porch at least, don’t get soaked.

He hesitated for a second, looked at the empty street, and agreed. I guided him down the little path to my front door. Under the sweatshirt, the baby doll brushed my skin with every step, and I was aware of every inch of fabric, of my hard nipples rubbing against the chiffon, of the thong soaked through with something other than rain.

—Come in for a second while I get the money —I said as I opened the door—. I don’t want the rain catching you again at the gate.

He came in. I closed the door. The rain stayed outside, beating against the windows.

***

—Wait here for me —I asked him, and walked toward the bedroom with my heart in my throat.

Inside there, I made the decision I’d spent years rehearsing in my head. I took off the sweatshirt and sneakers, put the red heels back on, and let the wig hair fall loose in front of the mirror. Maybe I looked too eager. Maybe I did. But I wasn’t going to waste the one time reality came so close to the dream.

I came out with the bills in my hand, my heels clicking on the floor. The man looked up and froze. He ran his eyes over me from top to bottom, from the heels to the wig, without hiding it, mouth slightly open and breath changed. I watched his cock harden inside his pants, swelling right there in front of me.

—You took your time —he said at last, with a half-smile—. And it was worth the wait.

I walked closer, making every step count.

—Do you like what you see? —I asked.

—I’m fascinated —he answered, and his voice trembled just a little—. I wasn’t expecting to find a slut this hot when I went out delivering.

The word went through me in one shiver. Everything inside me clenched tight. I set the bills on the table, with no intention of giving them to him yet.

—Come on, sit down —I told him, pointing to the sofa.

He sat down without taking his eyes off me. I knelt between his legs, feeling the carpet under my knees, and placed my hands on his thighs. I looked up at him while I unbuckled his belt and pulled down the zipper of his pants. He lifted his hips to help me, and in a matter of seconds his clothes were around his ankles along with his boxer briefs, and his cock sprang up in front of my face, thick, veined, the tip already shining with precum.

My mouth watered. It was exactly the kind of cock I’d fantasized about my whole life: a big, grown man’s cock, the kind that had been fucked plenty of times and knew what it wanted.

I took it in my hand and felt it throbbing against my palm, hot, heavy. I stroked it slowly from base to tip, squeezing just a little, gauging his reaction. He closed his eyes and tipped his head back against the backrest with a rough groan.

—Suck me, gorgeous —he murmured—. I’ve been thinking about your mouth all afternoon since I saw you in the rain.

I started at the tip, with my tongue flat, licking up the drop of precum like it was candy. Then I worked my way down the shaft, kissing every vein, and sucked his balls one by one, taking them into my mouth while I kept jerking him with my hand. I heard him mutter a curse under his breath and that only made me hotter.

I went back up and took him all the way in, as much as I could. His cock opened my throat up, my eyes filled with tears, my mascara ran, and even so I kept going down until my nose bumped against his pubic bone. He tangled his fingers in my wig and started setting the rhythm, pushing my head against his cock, fucking my mouth without asking permission, exactly how I wanted it.

—That’s it, baby, that’s it —he growled—. Mouth open, swallowing it all like the little slut you are.

I relaxed my throat and let him do it. I felt strings of spit sliding down my chin, tears mixing with the red lipstick smeared by his cock, and I didn’t care about anything. I ran my tongue over his balls, sucked them while I jerked him off, and took his cock all the way in again. My mouth made a slurping noise, obscene and wet, and he looked down at me with the smile of a satisfied male that made me clamp my thighs together.

—Wait —he gasped after a while, gripping my chin firmly and popping me out of his mouth with a wet sound—. If you keep going like this, it’s going to be over too fast. And I still want to fuck you.

I looked at him with my lips shining, saliva hanging from my chin, breathing hard.

—What do you want to do to me? —I asked, even though I already knew.

—I want to take you to bed and split you in two —he said, unfiltered.

A moan slipped out of me. I stood up, held out my hand, and guided him down the hall to the bedroom, the two of us silent, with the rain in the background and his cock pointing at me as he walked behind me.

***

In the room I turned on only the bedside lamp, that warm light that softens everything. I pulled the baby doll off over my head and let it fall to the floor, staying in my black thong and heels. He stripped fast, without the elegance he’d had before, needy now. Broad chest, a stomach only slightly marked by the years, cock swollen and red, aimed at the ceiling.

—Get on all fours for me —he ordered, in a different voice, lower—. I want to see that little ass first.

I obeyed without thinking. I got on the bed on my knees, heels still on, arching my back, giving him my ass. I felt his big hands spreading my cheeks, and then his face there, his rough beard against the softest skin I had. A cry escaped me when I felt his tongue.

He ate my ass slowly, hungrily. He licked me in circles, pressed the tip of his tongue against my hole, worked his way in little by little. He shoved in one thick, wet finger up to the knuckle, then two, digging into me, opening me for himself. I buried my face in the pillow and pushed my ass back toward his mouth, dying for him to put his cock in me.

—Please —I begged him—. Please, fuck me already.

—Not yet, slut —he said, and bit one cheek—. I’m going to get you nice and ready so you can swallow my whole cock without complaining.

I heard him tear open the condom wrapper, the sound of lubricant pouring out, his heavy breathing behind me. He lubed himself up well, lubed me up too, and I felt the head of his cock resting against my hole, thick, threatening. He started in slowly, with a patience I both thanked and hated at the same time. A long moan slipped out of me when the first inch opened me up, and another when he kept pushing, millimeter by millimeter, until I felt his balls against my skin.

—All the way in, baby —he growled, still as he was above me—. All that cock inside that tight little ass.

—God —I panted—. Don’t stop. Never stop.

He began to move with slow, deep thrusts, pulling almost all the way out and sliding back in to the hilt again. My ass burned and throbbed at the same time, and every stroke tore a new moan from me. He grabbed my hips with both hands, dug his fingers in, and sped up. The bed started hitting the wall, and I pushed back to meet him, moaning like a bitch, mouth open against the pillow.

—You fuck so good —he whispered in my ear, leaning over my back, never stopping his thrusts—. Such a hot little ass, all mine.

—Yes, yours, all yours —I answered without thinking—. Fuck me however you want.

He grabbed the wig hair and tugged gently, arching me even more. He drove his cock deep with every thrust and I felt him opening me from the inside, filling me completely. He reached a hand around and took my hard cock, wet with so much precum, and started jerking me off in time with his thrusts. I almost blacked out.

We changed positions. He laid me on my side, pressed himself against me from behind with one leg between mine, and kept fucking me like that, slower, deeper, biting my neck, pinching one nipple between his fingers. Then he put me on my back, spread my legs wide, and got between them. He made me rest my heels on his shoulders and came back in, looking me in the face while he fucked me.

In that last position I stayed caught on his gaze, on the concentration on his face, on the way he watched me as if I were the only thing in the world. He moved with a steady rhythm, each thrust sinking in all the way, my cock bouncing against my belly with every hit. He squeezed my small tits, pinched my nipples, bent down to kiss me with his mouth open and shoved his tongue as deep as his cock.

—I’m going to come —he said suddenly, voice breaking—. Tell me where you want it.

Then I did what I liked most. I stopped him with one hand on his chest, slid out of the bed, and knelt in front of him, mouth open and tongue out, looking up at him like a devotee in front of her altar. He took the condom off with clumsy fingers and started jerking himself off fast, his cock shining with lubricant and saliva, pointing at my face.

—Open wider —he ordered—. Stick out all your tongue.

I obeyed him. It only took a few seconds for him to finish with a long groan, holding onto my shoulder so he wouldn’t lose his balance. The first rope hit my cheek, hot, thick; the second landed on my tongue, salty; the rest filled my mouth, slid down my chin, dripped between my tits. I took it all without moving away, swallowing what I could, letting the rest mark my face and chest.

When he was done, I stayed kneeling, breathing hard, with his load running down me everywhere. I took my own cock in my hand, jerked it just three times, and I came too with a long shudder, splattering his legs and the carpet. Seeing him like that, wrecked because of me, had pushed me to the edge almost without even touching myself.

We stayed quiet for a moment, catching our breath, the rain still falling outside.

***

He got dressed slowly, calm now, while I put on a robe without cleaning myself off completely, because I wanted to keep feeling him on me a while longer. At the door he stopped, the pharmacy bag forgotten in one hand, and looked at me in a different way, more curious than needy.

—I make deliveries all over this area —he said—. Usually in the afternoon.

—I’ll keep that in mind —I answered, biting my lip—. I’m a regular customer.

He smiled, opened the umbrella, and disappeared into the rain toward his motorcycle. I closed the door and leaned against it, heart still racing and semen already drying at the corner of my lips.

That night, in front of the mirror, while I slowly took my makeup off, I stayed looking at myself for a long time. I had carried that fantasy for years, polishing it in the dark, convinced it would never leave my head. And there I was, smiling to myself, with the taste of his cum still on my lips.

I was already thinking about my next order.