My inmate came to turn me into his tranny

My name is Vanesa, I’m forty-two years old, and I’m a tranny. A woman with generous curves, one of those some people call a thicc babe with a crooked smile. From a very young age I liked dressing and behaving as what I always felt I was, but for years I lived it behind closed doors, in secret, making do however I could and getting myself off online without ever daring to take the step.

A year and a half ago everything changed. I got lucky with an unexpected prize and bought myself a beautiful penthouse on the outskirts. At last I was able to dedicate an entire room to my things, to the Vanesa who had been kept hidden away. I gradually filled it: impossible heels, tight dresses, lace lingerie, stockings, wigs of every color, makeup, false nails, toys of various sizes, and even a mechanical stand to use them hands-free.

I enjoyed myself alone, in front of the screen, in those video calls that at first embarrassed me and that over time became my greatest pleasure. My toys gave me deep orgasms; I learned to come with hardly touching myself at all. But I had never met anyone in person. Fantasy and real risk were two worlds I kept well apart.

Until he appeared.

I met him in a chat almost a year ago. He told me he wrote from prison, that he was serving a long sentence, and that women like me drove him crazy. That he had a huge cock, so huge that many women got scared, and that because of that he had ended up preferring little girls, the ones who — he said — were more giving and could take it better. I don’t know how much of that was true and how much was pure prison swagger, but the conversation got me going like crazy.

We started a long-distance relationship in which I was his tranny slut and he dominated me through the screen, giving me orders I obeyed like a horny automaton. His name was Bruno, or at least that’s how he introduced himself to me. We were like that for nearly five months, him dictating and me obeying, convinced that there would always be a concrete wall and miles of distance between us.

That Friday I got myself all made up for him. Full hair removal, freshly done long nails, the prosthetics fitted neatly under a short, tight, low-cut black dress. I put on a sleek dark wig pulled back into a high ponytail, and fourteen-centimeter black heels. I looked at myself in the mirror and felt powerful, beautiful, completely myself.

Tonight I’m going to drive him crazy again.

I ordered sushi delivery, partly because I was hungry and partly for the thrill of the delivery guy seeing me like that. It turns me on to see the look on their faces, that mix of surprise and badly hidden desire. I don’t care what they think; on the contrary, it feeds me.

When the doorbell rang, I didn’t hesitate. Certain it was the order, I yanked the door open.

It wasn’t the delivery guy.

It was a huge man, much bigger than he had looked on camera. Broad-shouldered, his arms straining the sleeves of his jacket, a sharp jaw and a predator’s smile. It took me an extra second to recognize him, and by then I already knew who he was.

—Hi, slut —he said, with a calm that chilled my blood—. You weren’t expecting me, were you? You look incredible in person.

—But… what are you doing here? —I stammered—. How do you know where I live? You’re in prison…

—I’ll explain later. For now I’m telling you I’ve got the whole weekend on leave, and I came to fuck you for real. Let me in.

—No… no way —I took a step back, my heart in my throat.

—What do you mean, no? —his voice didn’t rise, and that made it more threatening—. I have all the video calls recorded. You’re crystal clear, with your toys, asking me for what you already know. Do you want your neighbors to see them? —he paused and let his gaze slide down my body—. Besides, you want it. It shows.

He was right about the last part, and that was what scared me most. I stepped aside and let him in. I was in shock, but inside something had ignited. He took my hand and made me turn slowly, his eyes traveling over me like someone inspecting something they had just bought.

—Fuck, you look even better than on the screen —he murmured, pulling me toward him with a hand low on my back—. We’re going to have an amazing weekend.

He pressed me against his body. Hard against my hip, I felt the size of what he was promising, and all the heat rushed through me at once. He kissed me deeply, his tongue sweeping through my whole mouth, biting my lip when he pulled away. Despite the fear, I surrendered in that kiss. And he noticed it: he noticed how I was melting, how my body was loosening and the old one was giving itself up.

—I can’t take it anymore —he said, breathing heavily—. On your knees. Take care of your man, he’s been locked up for a long time.

—Bruno, I… —the words wouldn’t come.

A firm hand on my shoulder pushed me down. It wasn’t brutal, it was inexorable, and I liked that more than I wanted to admit.

—Come on, start —he ordered.

I unzipped his pants with trembling fingers. When I freed him, I caught my breath. It was exactly as he had promised and more: thick, taut, impossible to wrap one hand around. I held it slowly, careful not to dig my nails in, feeling the weight and the heat.

I started stroking him up and down and he gave a low growl.

—Those nails… that soft hand… —he closed his eyes for a moment—. But I want your mouth. Take it in.

He guided my head and I took only half of him at first. I ran my tongue over him, licked him all over, trying to keep up with the rhythm he set while holding my ponytail. He shoved it deep into my throat, enough to make me gag, and pulled it out just in time for me to breathe.

—That’s it, that’s it —he panted—. You’re so good at this. Keep going.

My own arousal kept growing even though my sex didn’t matter at all; all the blood, all the urgency, had concentrated in another part of my body, pulsing with need. I don’t know how long we stayed like that until I felt him swell and jerk against my palate.

—I’m coming —he growled, burying himself down my throat—. Swallow it, I don’t want a single drop outside.

I swallowed as best I could, though some escaped the corner of my mouth and ran down my chin. I coughed, eyes watery, and right then the doorbell rang.

The delivery guy.

Before I could react, Bruno went to the door and opened it with complete shamelessness, leaving me there, on my knees in the middle of the living room and my face a wreck.

—Ah, great, dinner —he said, perfectly calm—. Is it already paid for?

The kid, barely twenty with his helmet under one arm, opened his eyes wide.

—Yes… yes, it’s paid for —he stammered, not knowing where to look.

—Then fuck off, kid. Can’t you see I’ve got this eager one here ready to leave me clean?

The delivery guy almost tripped as he turned around. I stayed there burning with humiliation, unable to believe what was happening, and at the same time more turned on than I had ever been in my life.

—Come on, bring me some beers —Bruno said, closing the door—. Take care of your man.

He sat on the sofa and opened the bag with my sushi. I had ordered enough, thinking I’d have it for several days; now it would be for both of us. I got up, trembling on my heels, and went to the fridge. The click-clack of my own steps brought me back to reality all at once: I was dressed like a fantasy, with a man in my house ready to use me all night, and I wasn’t trembling from fear. I was trembling from desire. For the first time, I understood how completely giving I was capable of being.

We ate in near silence while he explained everything to me. From now on, I would be his. Every few months he’d get leave and come so his woman could take care of him the way God intended. He didn’t pose it as a question. And I, who should have had a thousand objections, found none.

—Let’s go to bed —he said at last, getting up—. Take off the dress and stay in the thong and heels. On all fours. And bring the lube.

—Yes, Bruno —I answered, with a submission that came naturally to me.

I got into position as he ordered, glancing sideways at that cock, hard again. I was excited and scared in equal measure, because I knew it was going to hurt. He came up behind me, caressed my ass, gave me a couple of spanks that echoed through the room, and slid two lubricated fingers inside me, opening the way slowly.

—Aaah… —I moaned, arching my back.

—Look how much you like it —he laughed, his voice deep—. Look how you’re asking me for more. Relax, I’m going to make you mine for real.

He parted me with both hands and set the tip against me. I closed my eyes and breathed deeply, trying to loosen every muscle so it would hurt less.

—Here —he whispered, and pushed.

The pain shot through me like a lash and I let out a cry that must have been heard halfway through the building. I clenched my teeth while he advanced centimeter by centimeter, unhurried, enjoying my resistance.

—That’s how it should be —he panted—. The first time has to really hurt. You’re so tight.

And then, little by little, the pain turned into something else. I felt him all the way inside me, filling me in a way no toy had ever managed, brushing against a spot that made me see lights. I felt like a woman, possessed, humiliated and desired all at once, and I wished with all my strength that he wouldn’t stop.

Before I knew it, I was the one pushing back, searching for his rhythm, moaning without holding back.

—That’s it, yes —he growled, digging his fingers into my hips—. Scream, let your neighbors know who’s in charge here.

—God… yes… more —I could barely recognize my own voice—. Don’t stop, please, don’t stop.

Pleasure built until it became unbearable. Without hardly touching myself, my whole body tensed and exploded in a succession of spasms that shook me from top to bottom. They must have clenched around him, because almost at once I heard him give in.

—I can’t take your squeezing —he whimpered, burying himself to the hilt—. I’m coming, slut… I’m coming.

I felt him throbbing inside me over and over, filling me, spilling with every thrust until the two of us were soaked on the unmade bed. I ended up lying face down, his weight on top of me and him still inside, both of us breathing as if we had run miles.

For the first time in my life I felt complete. Humiliated, yes, but whole. Full, trembling with the last echoes of an orgasm I had never known. I thought I finally understood something that had always eluded me, and that this weekend was only just beginning.