The Man Who Replied to My Ad That Very Night

My name is Brenda. I’m twenty-seven and I live in a northern city I’d rather not name, in a tiny apartment that’s all mine.

I’m a closeted trans girl, short, brown-skinned, with curves I take great care of. No one in my life knows, and that secret part of me is exactly what turns me on most.

I like older men, the ones who don’t ask twice, the ones who walk into a room and already know where they’re headed.

Without beating around the bush, I’m going to tell you what happened to me a few weeks ago, because I still can’t get it out of my head.

One night, bored and craving something I couldn’t even name, I stumbled onto a dating site. Curiosity got the better of caution. I made an account and, before I could second-guess myself, I posted an ad offering myself to mature, decisive men. I uploaded a couple of nicely done-up photos of myself, dressed the way I like to look when I’m alone, and typed the text in one go.

The ad said something like this: I’m looking for an older, real man with no games, someone who knows how to treat a trans girl like me. I’m open to anything, I give myself completely, and my mouth is my favorite part. I hit publish and closed the app with my heart pounding in my throat, certain no serious man would answer.

I was wrong.

The next morning, my inbox was full. Most of it was the same stuff I already knew by heart: crude messages with no greeting, blurry pictures of dicks under bad lighting, men who wrote three words and vanished. I was this close to deleting everything. And then one different message appeared.

It was from a man who introduced himself as Rolando, fifty-one years old, widower, calm voice even in writing. He didn’t start by asking for anything. He asked what my name was, what I liked, whether I was nervous. He treated me like a person, and for some reason that unsettled me more than any shameless line ever could.

—I don’t want to rush you —he wrote—. But if at any point you feel like it, I’d love to meet you.

We talked for two days. He sent me a photo of himself, dressed, leaning against a car, with graying hair and a confident smile. I liked that he wasn’t perfect. I liked that he seemed real.

He asked me what I was looking for, and for once I didn’t have to lie. I told him I wanted to feel desired without having to ask for permission, that I was tired of men who wrote a lot and showed up rarely, that I wanted a real dick, not promises. He read that and took a long minute to answer.

—I’m not the kind who disappears —he wrote—. When I say I’m coming, I come. And when I get there, you’re going to remember why you opened the door for me.

This one, I thought. This is the one.

We agreed to meet on a Friday, at 10:30 at night, at my apartment. All week long I lived with that meeting under my skin, counting the hours in silence while the rest of the world still knew nothing at all.

At work I could barely focus. On the bus I kept checking my phone, rereading our messages like a teenager. At night I had trouble sleeping, imagining over and over what it would be like to open the door and find him on the other side. More than one early morning ended with my hand between my legs, thinking about his mouth, his big hands, what he was going to do to me.

***

On Friday I started getting ready early, like someone preparing a ritual. I took a long, slow bath, taking care with every detail, shaving every last inch, washing myself inside with patience because I knew I’d end up getting fucked hard and didn’t want any surprises. When I stepped out of the shower, my skin was soft and carrying a sweet scent that wouldn’t go away.

Then I got dressed. I chose a white lace thong, a short black sheer chiffon slip, and a pair of slim-heeled shoes that made my legs look longer. I did my makeup calmly in front of the mirror, defining my eyes, shaping my mouth —the mouth I’d promised him in the ad— and put on a long dark wig that fell over my shoulders.

A touch of perfume behind my ears, on my neck, and between my breasts, and I was ready. I looked at myself one last time and barely recognized myself. That night I wasn’t the closeted girl nobody sees. That night I was exactly who I wanted to be: a gorgeous slut waiting for her man.

At exactly 10:30, the doorbell rang. My breath caught. I walked to the door trying not to let my legs shake and opened it.

Rolando was taller than I’d imagined. He had broad shoulders, big hands, and a look that traveled over me from head to toe without shame, lingering on my tits barely covered by the sheer fabric. He didn’t say anything sycophantic or filthy. He just smiled, slowly, as if confirming something he already knew.

—Hi, Brenda —he said, and my name sounded different in his mouth.

—Hi. Come in.

He came inside, set a bag with some beers on the table, and looked around the apartment with friendly curiosity. I didn’t know what to do with my hands. He, on the other hand, seemed in command of every gesture.

—You’re gorgeous —he said—. Even more than in the photos.

I felt my face burn. I opened two beers and we sat on the couch, close, but not touching. We toasted to nothing in particular and started talking. He told me about his job, his quiet life, his craving for something that would pull him out of the routine. I told him only what was necessary, what you can say without giving yourself away completely.

The alcohol loosened the nerves. By the second beer we were laughing, and every now and then his knee brushed mine and neither of us moved away.

I liked the way he looked at me when I spoke, without interrupting, paying genuine attention. He had a calm way of taking up space, without pressuring me, as if he knew that sooner or later I’d close the distance on my own.

—I’m nervous —I confessed, playing with the label on the bottle.

—I know —he replied—. Don’t rush. I’m not going anywhere.

—Do you know how to play anything? —he asked suddenly, with a mischievous spark.

I pulled an old wooden die from a drawer, the kind with a command on every face. Without saying it outright, we’d turned it into an excuse. We took turns rolling, and the side that came up determined what had to happen: a caress, a kiss, one less piece of clothing.

The game moved slowly, and that was the best part. I watched him use every roll to find a way closer, to touch a little more, to gain ground. Several times the die landed on the face that forced me to kneel in front of him, and I didn’t mind. On the contrary. Every time I went down between his legs I could feel the bulge growing under his pants and my mouth flooded with saliva.

With each turn, the clothes became more of a nuisance. He took off his shirt when it was his turn, and I found a firm pair of shoulders and a broad chest with gray hair that made me want to bite him. When it was mine, I let my shoes fall to the floor, one and then the other, never taking my eyes off him. On the next roll he pulled the slip over my head and left me there, sitting in front of him in my white thong with my tits bare, breathing hard.

His hands began to linger longer on my skin. First my knee, then my thigh, then my waist, then one hand closed around a whole breast and pinched my nipple with two fingers until I let out a soft moan. He wasn’t in a hurry, and that slowness was driving me mad faster than any urgency could. Under the thong I was already showing everything, hard, wet at the tip, and he saw it and smiled like someone recognizing a gift.

—Look at how wet you are —he murmured, sliding a finger over the soaked lace—. And we haven’t even started yet.

***

When the mood was already hot, he put the die on the table and took my hand.

—Let’s go somewhere else —he said softly.

I led him to the bedroom. The moment we crossed the doorway he wrapped his arms around my waist and kissed me. It was a deep kiss, slow at first, turning urgent as it went on. His tongue opened my mouth like he already knew me, and I sucked on it slowly, biting his lip, letting him press me against the wall. His hands slid down my back to grab my ass hard, firm but not painful, parting my cheeks over the lace. A shiver ran through me.

—What a little ass you’ve got —he said against my ear, biting my earlobe—. You’re going to see what I do with this.

He turned me toward the wall and pressed his body against my back. I felt his hard cock outlined between my cheeks, still trapped in his pants, and I pushed my ass back without thinking, searching for it. He brought one hand around to the front, grabbed my tits one by one, pinched my nipples until I trembled, and with the other he slid down my stomach until he found my hard cock under the lace. He closed his hand around it, weighing it, and let out a deep laugh.

—Naughty girl. Hard and ready for me.

I lowered myself slowly, sliding down his body until I was kneeling in front of him. I undid his belt while looking him in the eye, tugged at the buckle with fingers that no longer shook, and pulled the zipper down with my teeth. When I tugged his pants and briefs down, his cock sprang out, thick, brown, swollen, the tip shining. I couldn’t help moaning just looking at it.

I took it in my hand —I could barely wrap my fingers around it— and ran my tongue from base to tip, slowly, tasting him all over. Then I kissed the head, sucked it like candy, buried my nose in his balls and licked them one by one. I went back up and took him into my mouth, first halfway, then deeper, forcing my throat until my eyes filled with tears. I pulled off with a string of saliva hanging from me and took him back in.

What came after I did with desire, with devotion, the way I like to do it: without hurry, listening to him breathe harder, feeling him give in with every movement of my mouth. I sucked him off while looking at him, I sucked him with my hand helping, I sucked him after spitting on him and using the saliva to jerk him off while I licked his balls.

He held my face with one hand, not forcing me at first, only setting the rhythm, letting me do it. Every so often he let out a low sound that made my skin prickle. I looked up to see his face, and that image of him lost, head thrown back and mouth open, was worth more than any words.

—Just like that, exactly like that —he murmured, burying his fingers in my wig—. You suck cock so well, slut. So well.

The word made me hotter. I dug my nails into his ass and took him to the back of my throat, holding back the gag reflex, letting him hold my head now and fuck my mouth. He thrust into me with short drives against my throat, and I cried and drooled all over him and didn’t want him to stop. When he finally let go, I gasped, my face undone and saliva running down to my tits, and smiled up at him from below with my mouth swollen.

I drove him crazy for a good while, until he couldn’t take it anymore. He lifted me off the floor almost in one motion and laid me on the bed. He ripped my white thong off with a yank —literally tearing the lace— and spread my legs wide open. He crouched down and buried his tongue between my cheeks, searching for my hole, giving long, greedy licks that made me scream into the pillow.

—Shut up, or you’re going to make me even harder —he said, and went back to eating my ass with even more hunger.

He licked me, sucked me, pushed his tongue inside, dotting me with it, and with his free hand he grabbed my cock and jerked me off at the same time. I was writhing, clutching the sheets, pushing my ass against his face, asking for more without even realizing it.

—Fuck me —I begged—. Please. I can’t take it anymore.

He straightened up, spit into his hand, slicked the head with saliva, and positioned me face down with two pillows under my hips to lift my ass up high. I felt the tip against my entrance and tensed.

—Easy —he whispered, kissing the back of my neck—. Slowly.

He entered me slowly, giving me time, gaining a centimeter and waiting, then another, until I felt him filling me completely. It hurt at first, but it was that kind of pain I love, the kind that turns into pleasure if you hold your breath and let yourself be opened. When he was buried to the balls, he stayed still, breathing against my ear.

—You’re so tight, fuck —he groaned—. What a little ass you gave me.

And then he started moving with more determination, deeper and deeper, firmer and firmer. I moaned into the pillow and begged him not to stop. He put me on all fours, held me by the hips with those enormous hands, and set a rhythm that made me lose my mind. I could hear the slap of his thighs against my cheeks, my muffled moans, his hot breathing on my back.

—Tell me you like it —he gasped, never slowing down—. Tell me.

—I love it, I love it, don’t stop, fuck me, fuck me hard.

He grabbed my wig, pulled my head back, and drove into me even deeper until I felt him all the way up to my stomach. He slapped my ass until my skin was burning, one cheek and then the other, and I trembled all over, with the hard cock between my legs bouncing in time with his thrusts.

At one point he stopped, turned me over carefully, and laid me on my back. He lifted my legs, propped them on his shoulders —my heels still on, now at the sides of his face— and plunged back in with one hard thrust, all the way to the hilt, while staring into my eyes, as if he wanted to see every expression on my face. That closeness, that looking at each other with nothing hidden while he split me in two, turned me on more than everything that had come before.

—Look at me —he ordered—. Don’t close your eyes. Look at me while I fuck you.

I looked at him. I saw the sweat on his forehead, the open mouth, the eyes locked on mine. He grabbed my cock with one hand and jerked me off in time with his thrusts, squeezing just right, while with the other he pinched one nipple. I was undone, legs spread, folded in half, leaking from the tip onto my own stomach, moaning his name.

—Rolando, Rolando, I’m going to cum, I’m going to cum like this.

—Cum, go on, cum for me.

And I came. I came with a sharp cry, clenching my ass around his cock, shooting hot streams over my belly and tits while he kept fucking me without losing the rhythm, stretching my orgasm until I screamed and begged him to ease up. He watched me come with a dark smile, bent down and licked my cum off my stomach, then spit it into my mouth. I swallowed it without thinking, watching him.

—Good slut —he said, and kissed me with my own cum on his tongue.

He kept fucking me like that for a long while longer, alternating brute force with pauses where he stayed inside me and kissed my neck, leaving me shaking. When I felt he was close to the edge, he pulled out, grabbed my wig, and knelt me in front of him again, his cock shiny and throbbing a hand’s breadth from my face.

—Get the rest out with that little mouth —he panted, jerking himself fast in front of me.

I took hold of him, finished stroking him myself, and took him all the way into my mouth for the last pull. I finished him with my mouth, just as I’d promised in that ad, feeling him empty into me in three, four hot bursts against my palate, with a rough moan tearing out of his chest. I stayed still, with him inside, swallowing slowly, and then I cleaned the tip with my tongue as if thanking him.

When I finally let him go, I opened my mouth to show him there was nothing left, and he smiled and stroked my face.

—You’re a goddess —he said, still breathless.

We lay there in silence for a while, catching our breath, still tangled up on the bed, him stroking my hair and me with my head resting on his chest. Then he dressed without rushing and I walked him to the door wrapped in a robe, my legs still weak and my ass still throbbing.

—Can I write to you again? —he asked before leaving.

—You’d better —I answered, and we both laughed.

I closed the door and leaned against it, my heart still racing and his taste still in my mouth. That night was exactly what I was looking for when I posted that ad: a real, decisive man who made me feel like his from start to finish.

And something tells me this story is only just beginning.