I Lost a Bet and My Friend Decided to Feminize Me

This is the first story I’ve ever dared to tell, and I still can’t believe it’s mine. My name is Iván, I’m twenty-one, and I have a rather slim body, almost skinny, except for my legs, which were always a little thicker than I’d like. I never gave it any importance until someone decided to make it important for me.

A few months ago I had a huge fight with my family. It’s not worth going into the details, but it ended with me hurriedly packing a bag and walking out the door without knowing where I was going. That was when Bruno, a lifelong friend, offered me a place in his apartment until I found somewhere of my own.

Bruno is twenty-five and moved out very young. He’s been working since he was twenty, he has his salary, his routines, his rules. At first, living with him was comfortable. I felt indebted, sure, but also protected, as if for once someone was taking care of me when everything else had fallen apart.

One Friday night we started drinking whiskey in the living room. The bottle went down fast and the conversation got serious between laughs.

—Look, don’t take this the wrong way —he said, pouring another glass—, but you’re going to have to get a job soon. I’m covering a lot of expenses and, friends or not, you should be contributing something.

—Bruno, I really have been looking. I sent resumes everywhere and nobody calls me back. It’s not that I don’t want to.

—I know you looked. But the truth is I paid for a lot of things this month and I need you to give me a hand.

—I swear I’m going to do everything I can. You helped me when I had nobody, I’m not going to forget it.

By the time we were halfway through the second bottle, he got up, rummaged through a drawer, and came back with a deck of cards. He dropped it on the table with a crooked, booze-softened smile.

—I’ve got a bet for you. We each draw a card, and whoever has the higher one wins. If you win, you don’t have to look for work for two more months, I’ll cover you. But if I win, for those two months you’ll have to do everything I tell you.

I laughed. I was drunk, and the idea of spending two months without the pressure of job hunting sounded like the best deal in the world. I didn’t even stop to think about the other half of the sentence.

—Fine, let’s play —I said.

He shuffled clumsily and spread the cards face down across the wood. He drew his first and turned it over: the eight of hearts. Not a high card. I felt like I had the whole world in my hands.

—Well then, that’s it, two months without looking for wor— —I started to say, confidently.

I picked a card from the pile and turned it slowly. The three of diamonds. My smile vanished instantly. Bruno burst out laughing and gathered the cards calmly, as if everything had been written out long before.

—Looks like I won, friend. So for two months you’re going to do whatever I say. Relax, I’m not going to be a tyrant. Wait a second, I’m going to get something.

While he got up, I poured the last of the whiskey down in one swallow. I was stunned. The room swam a little and I kept trying to convince myself it would be something stupid, a drunk joke neither of us would remember tomorrow.

—We’re starting today —he said when he came back—. Come with me to the bathroom.

He was carrying something in his hand that I couldn’t make out. I followed him, dizzy, with that mix of curiosity and fear that freezes you right when you should stop. He shut the bathroom door behind me and put an object in my hand.

It was a chastity cage. Pink plastic, glossy, with a single key hanging from a cord.

—You’re putting this on —he said with a calm that chilled me—. When you’re ready, come out and show me you put it where it belongs. If you don’t know how to use it, find yourself a tutorial.

—Wait. No, I’m not doing this. Why would I have to put this on?

—Because you lost a bet. And because if you don’t do it, you grab your things and leave here tonight. I’ll be waiting at the table.

He closed the door and left me alone, trembling. I looked at myself in the mirror: face red from alcohol, eyes wide with panic, the pink cage in the palm of my hand like a sentence. I thought about my bag, the empty street, having absolutely nowhere else to go. And that thought weighed more than any shame.

I searched on my phone for how to put the thing on. My hands shook so much it took me twice as long as normal. I pulled down my pants, my boxers, and stared at my flaccid cock, shriveled by nerves, knowing it was the last time in a long while that I’d see it free. I slid the ring behind my balls, forced my cock into the pink tube, clicked the lock shut, and heard the tiny padlock make a dry snap. When I finally managed it, I felt the cold plastic enclosing me, tight, impossible to ignore. Every movement reminded me of it.

I took a deep breath, pulled my pants back up, and came out.

—It’s on —I said, not daring to look up.

—Show me.

I looked at him, pleading with my eyes for him not to make me. But his expression didn’t change. I lowered the zipper and showed him the cage trapping me inside it. I could feel my face burning like never before.

—It suits you —he said, and laughed—. Now give me the key.

I handed it over. He tucked it into his pants pocket with a natural ease that gave me chills, like he were putting away car keys. Then he opened another bottle and poured himself a drink, gesturing for me to sit beside him.

—Are you going to tell me something, or are you going to sit there mute all night? —he asked, amused.

The rest of the evening he acted as if nothing had happened. We talked about football, about a series we were watching, about any old nonsense. But I couldn’t focus on anything. The cage pressed against me every time I moved, and every time he looked at me with that little smile I felt like he knew. I shifted on the couch, uncomfortable, and that seemed to please him even more.

—Sit still —he said at one point, without raising his voice—. You’d do well to get used to it.

That sentence went around in my head all night. Get used to it. To what exactly? I didn’t dare ask.

At one point he leaned toward me, set his hand on my knee, and left it there, unmoving, while he kept talking about the series as if nothing were happening. The heavy, warm palm began to travel slowly up the inside of my thigh, squeezing the flesh, measuring me. When it reached the bulge of the cage, he pressed over my pants and smiled at feeling the hard plastic where my cock should have been.

—Would you look at that —he murmured—. You’re already getting hard inside. You can tell, you know? It swells against the plastic and has nowhere to go. Good boy.

Those two words unsettled me more than the cage. No one had ever spoken to me like that, and yet they settled somewhere in me I hadn’t known existed. I could feel my cock, trapped, trying to grow and hitting the plastic walls again and again until it hurt. And he, meanwhile, kept massaging my thigh, edging closer and closer to my ass, as if he were evaluating a purchase.

—Get up —he said suddenly—. Take your pants off. I want to see you properly.

I didn’t move my feet. He tilted his head and waited, without repeating himself. In the end I stood, fumbled with the belt buckle, and let my jeans fall to the floor. I stayed there in my T-shirt, with the pink cage gleaming under the yellow living-room light, feeling the thick legs I had hated so much trembling beneath me.

—Turn around. Slowly.

I turned. When I was facing away from him he put both hands on my ass and squeezed, spreading it with his thumbs over my boxers.

—You’ve got a slut’s ass, Iván. Seriously. Has nobody ever told you? With these legs, this ass… it’s a waste for you to be going around without an owner.

—Bruno, I… —I tried.

—Shut up. Come here.

He sat me astride him, looking at him, with the cage pressing against his stomach. He grabbed the back of my neck and brought my face close to his. His whiskey breath hit my mouth before his lips did. He kissed me slowly at first, biting my lower lip, then shoved his whole tongue in, forcefully, and I opened my mouth without deciding to, as if my body already knew something my head was still denying.

While he kissed me, one of his hands went down to my boxers, pulled them aside, and slipped a finger between my cheeks, probing. When he found the little hole he pressed the fingertip against it, not pushing all the way in, playing.

—Virgin here, right? —he said against my mouth.

I nodded, unable to speak. He gave a low laugh.

—Good boy. Much better.

He made me get down. I understood without him telling me, or maybe my body understood for me. I ended up on my knees between his legs, on the rug, looking up at him with my face burning. He unzipped his pants without hurry, pulled them down a little, and took out his cock. My breath caught. It was thick, longer than I’d ever imagined in the shower once by accident, veins standing out, the head already shiny and peeking out. He pressed it to my cheek, warm, throbbing.

—Suck it —he ordered—. All of it. And slowly, because I want to see you learn.

I opened my mouth. He guided me himself with a hand on the back of my neck. The thick head slid past my lips and my tongue was flattened against the vein underneath. It tasted like skin, soap, and something salty that stuck to my palate. I started moving, clumsy, sucking as best I could, my cheeks hollowed out. He watched me with a slow smile, not helping.

—Deeper. Don’t be scared, it’s a cock, it’s not going to kill you.

He pushed my neck. His dick hit the back of my throat and I gagged, saliva streaming from the corner of my mouth down to my chin. My eyes filled with tears. He let me breathe and pushed again. And again. And again. He fucked my mouth calmly, measuring me, while I tried to coordinate breathing and not choke. The cage between my legs pressed harder than ever. With every retch it made me feel smaller, more ridiculous.

—That’s it, that’s it, good boy. Suck that cock the way you’re supposed to like sucking it.

When my face was soaked with spit and drool, he let go of my neck. He looked at me with his cock coming out of my mouth, shiny all over, and smiled.

—Stand up. Turn around against the couch. Hands on the backrest.

I obeyed without thinking. He yanked my boxers down to my knees. I felt him spit into his hand and then two of his fingers, wet, against my hole. He rubbed around the outside first, pressing, then slid one in to the knuckle. I screamed more from surprise than pain. He covered my mouth with his other hand.

—Shhh. Take it. You’re going to take a lot more than this.

He moved the finger inside, pulled it out, spat more, pushed in two. My thick legs, the ones he had watched so much since I arrived, were trembling. I arched without meaning to, pressing my forehead against the back of the couch as he opened me with his fingers. The cage bounced loosely between my thighs, trapped, useless.

—Look at it —he said, tapping it with his nail—. Look how turned on you are and your little cock’s just trapped there doing nothing. That’s how I want you. That’s how you’re going to be for two months.

When he pulled his fingers out, I felt the thick head of his cock settling where he had been spitting. He pushed in slowly. The pain cut through me like a hot knife and I screamed into the couch, biting the fabric. He kept pushing, millimeter by millimeter, unhurried, gripping my hips with both hands.

—Loosen up your ass. Loosen up. Good boy. Almost there, almost all the way in.

When his balls touched my ass, he went still for a second. I was breathing in ragged gasps, mouth open, feeling my whole body throbbing around that cock. Then he started moving. Long pulls, thrusts all the way in. The slap of his hips against my ass filled the living room, mixed with my muffled moans and his increasingly hoarse breathing.

—Hear how it sounds —he panted—. Hear how I’m fucking you. This ass is mine now. All of you is mine. The key, the ass, the mouth. Everything.

The cage bounced between my legs to the rhythm of his thrusts. I tried to come and couldn’t, the plastic stopping me, and yet the pleasure rose anyway, from somewhere else, deeper in, a new pleasure that made me dig my fingers into the couch and push my ass back for more without saying it.

—Tell me it’s mine —he growled, grabbing my hair—. Say it.

—It’s yours… —I moaned, my voice broken—. My ass is yours, Bruno.

—All of it.

—All of it… all yours.

—Good boy.

He sped up. His fingers dug into my hips. He fucked me hard, without restraint, until I heard him let out a long grunt, pressing me against him, and I felt his hot load spurting inside me. He stayed there, cock buried deep, breathing on the back of my neck, until the very last contraction. Then he pulled out slowly and gave my ass a slap.

—Stay like that for a bit, legs spread. Don’t let anything drip out. I want to see you can hold it in.

I stayed as he’d told me, face pressed to the back of the couch, his warm cum sliding slowly inside my thigh, the pink cage hanging wet with spit and my own sticky release. He poured himself another whiskey and sat on the couch, a meter away, watching me with a calm that scared me more than if he had yelled.

—You’ll see how you get used to it —he said, taking a sip—. I told you. Good boy.

When we finally went to sleep, each in our own room, I lay staring at the ceiling for hours, body caged and mind even more so. I could still feel him inside me, my ass throbbing hot, the cage stuck to me with everything. Part of me was terrified. Another part, one I didn’t want to acknowledge, couldn’t stop thinking about what was coming.

***

The next morning I woke up late, mouth dry and head heavy. Bruno wasn’t there. On the kitchen table there was a note written in his hurried handwriting: “I went out to buy a few things. When I get back I want something ready to eat. And don’t even think about taking off what you wore last night.”

I read the last sentence three times. I took my hand to my forehead almost on reflex and confirmed the cage was still there, reminding me that last night hadn’t been a dream. It was still locked. And the key was with him, somewhere in the city, beyond my reach.

I sat there for a while, turning everything over in my head. I thought about how easy it would be to end this: rip the cage off, pack my bag, leave. But the reality was brutal. I had no money, no job, no other roof over my head. And, if I was completely honest with myself, it wasn’t just fear holding me there. There was something about obeying, about handing over control, that stirred me in a way I didn’t fully understand.

I got up, opened the fridge, and started preparing something for when he came back. While I cooked, every movement reminded me of the tight plastic between my legs and the burn still alive in my ass, and I surprised myself thinking about what else he would ask of me. What else I’d be willing to do just to avoid being thrown out. Who I’d be when those two months were over.

I heard the key in the front-door lock and my heart flipped.

If you liked this story and want to know what happened when Bruno came back with the bags, and everything that came after, leave me your support and I’ll be posting part two very soon, darlings.