My First Day Out Dressed as a Woman

I spent the last days of summer locked in my room, alone with my dildo and with a restlessness that wouldn’t go away. Physically I was satisfied; I could give myself pleasure whenever I wanted, shove the plastic all the way in and make myself come two, three times a night. But there was something the dildo couldn’t give me, an urgency that only grew with each dawn: the need to have a real cock inside me, hot, throbbing, the kind a man would hold me by the hair while he fucked me with. I wanted to feel someone else’s cum dripping down my thighs, not pharmacy lubricant.

I thought going back to college would calm things down. I was wrong. I spent class time drifting, imagining myself walking into the classroom in a skirt, wondering what my classmates would look like with their cocks out. And, without really knowing why, I got even hotter imagining myself with one of the professors: the literature teacher forcing me to suck him under the desk, the history professor pinning me against the blackboard to fuck me from behind. Sometimes, when I left, I went with Lucía; we’d lie down and she’d eat my ass patiently, lick me all over, shove two fingers into me until I was shaking, but no matter how much I liked her, I always ended up with the same half-full feeling. I didn’t want to penetrate. I wanted to be penetrated. I wanted to be opened up, filled, used.

One afternoon Renata called me. She had a proposition for me.

—What if you spent an entire day as my doll, with Adrián? —she said, like she was offering a gift.

—What day? —I asked, already with my pulse racing and my cunt, the one I still didn’t have but could feel every time I got turned on, tightening on its own.

—This Friday. Skip class and come early.

I paused to think for a second. Just one second.

—Yeah —I said—. I’m in.

That morning I told my parents that after class I’d spend the day with Lucía. They said that was fine. Instead of putting notebooks in my backpack, I packed clothes, as much as I could fit, and left at seven. Not for college, but for Renata’s place.

I got there a little before nine. She opened the door in a robe, a robe so sheer that everything showed through: her dark nipples outlined under the silk, the triangle of her shaven pubis almost bare, the curves of a woman who knew exactly what she was doing with her body.

—Hi, Marina, I’m so glad you made it —she said, stepping aside—. Come in. Did you skip?

—Yeah, I ditched class —I replied, smiling.

—Can’t wait for Adrián to fuck you like his girl again, huh?

—Something like that.

—He told me that last time you couldn’t stay off him —she said with a naughty smile—. That you kept asking for more cock, that you licked every last drop of his cum.

—I really liked being with him —I admitted, and felt my face burning.

She told me to take my clothes off and have a bath in her tub. She said she wanted me to smell like a princess, but be ready on the inside like a slut. Not even two minutes passed before I got hard. Renata noticed right away and started touching me without asking, her cool hand closing around my little cock, sliding up and down with a slowness that made my knees tremble.

—Tell me, Marina, what did you like most about Adrián?

—The way he did it to me —I said, almost voiceless—. Feeling his cock inside me, hot, and him shooting ropes inside me without pulling out.

—And you want him to do it to you again?

—Very much. I want him to open me up again, leave me full.

—I’m going to relieve you a little now —she murmured— so you don’t spend all day unbearable, thinking about Adrián’s dick.

She didn’t just stroke me. She knelt on the tiles, spread my thighs, and lowered her head with that natural ease she had about everything sexual. Her tongue circled my glans first, slowly, testing, and then she took my whole cock into her mouth in one go, until I could feel the head against her throat. She started sucking me with a perfect rhythm, cheek in, cheek out, her tongue coiling around the shaft, her lips closed just enough. Every so often she’d pull all the way off, spit on me, take me in her hand again and look up at me from below, her eyes shining, before swallowing me again. She sucked my balls too, one by one, pampered them with her tongue, and went back up. I enjoyed it with my mouth open, trying to learn from her, until I came without warning, a long spurt that filled her mouth. She swallowed it all without taking my cock out, wiped away a drop that had escaped to the corner of her mouth with her thumb, and smiled at me.

—Tasty —she said—. All right, now into the water.

I was embarrassed, but she said nothing; she kept licking my pubis a little longer, leaving me clean, and then we went on with the bath. I loved hearing her praise my body while she soaped me up, her fingers tracing every corner, pausing between my ass cheeks, teasing the entrance to my asshole until she gave a little start.

—You’ve got a beautiful body —she said—. Almost no body hair, that’s what they love. Smooth, like it should be. And this little ass... this little ass is going to make a lot of people happy.

—Thanks —I answered—. I like how I look too.

I got out of the tub and she dried me with a towel, slowly, lingering on my nipples until they were hard, on my thighs, on the crack of my ass. Then she rubbed on creams that smelled like flowers, as if I were her porcelain doll, and took the chance to push a lubricated finger into my ass, twisting it, pulling it out, sliding it back in. The idea turned me on, and I started getting hard again. Renata laughed and went to the wardrobe to fetch something.

—Look, I brought this so you behave —she said—. I know you’re horny, that’s normal. But with this on, nobody will be able to tell if you get hard out in public.

It was a pink plastic chastity cage. I got a little scared when I saw it. After she explained it to me, I agreed to let her put it on me. Not even a minute had passed and I was already turned on seeing my cock locked away, useless, squeezed, at her mercy.

—Luckily you’re not very big —she said, adjusting it, toying with the balls left outside—. Nothing will show under the skirt. Here, this is the key. Take it off when you get home.

I smiled nervously and let her finish.

—You have no idea how hot it makes me to see you like this, caged —she went on, giving me a lick on the neck—. It makes me want to keep you with your legs spread all day, with a dildo in you, so your ass is nice and stretched before Adrián gets here.

—You can, if you want —I said.

—Hold on. My time is coming, and I’m not letting you go until I’ve got you nice and open, dripping.

I wanted to get hard and couldn’t; the cage pinched me, a sweet irritation that promised to become a habit. Renata started dressing me. She showed me a drawer full of underwear, all of it youthful; I chose a black one with purple details and a skull print with a bow, and a pink bra. Then a black pleated skirt and a striped long-sleeve blouse, fishnet stockings and, finally, a wig: long, straight, black, clearly good quality. She fixed it in place and did my makeup patiently. When I looked in the mirror, I was unrecognizable. I didn’t look dressed up. I looked like a woman. And that excited me more than almost anything.

***

Adrián arrived around noon. His face lit up when he saw me and his cock immediately outlined itself against his pants.

—You outdid yourself, Renata —he said, not taking his eyes off me—. She looks gorgeous. I want to fuck her right here, on the table.

—Helps that she’s got a great body —Renata replied—. The only thing is, she’s restless. But I found the solution. Lift your skirt, Marina, let him see.

I lifted it and let him see the pink cage squeezing my cock. Adrián made a crazy face that sent a shiver through me. He came closer, slid his hand under my skirt, felt the cage, pinched my ass.

—You look so damn tasty like this —he said—. We’d better leave now, or I’m going to start pawing at you right here and we won’t get anywhere. Renata, the key.

—She has it. She takes it off at home. Until then, deal with it.

Before we left, Renata handed me a face mask so I’d be less noticeable. We got into Adrián’s car and headed for a shopping mall. On the way he talked to me in that low voice that got me going, his right hand resting on my thigh, sliding up every so often to brush the cage over my panties.

—It’ll be empty at this hour —he said—. Don’t get nervous. How are you feeling?

—Good. A little nervous. But I don’t think anyone will recognize me.

—You really wanted me to fill you up with cum again?

—Very much —I answered—. What time?

—Still a while. First we’re going to walk around, I’m going to spoil you. Though just in case, call me “daddy.” To keep up appearances.

—Okay, daddy —I said, and I liked the word more than I expected; it made me wet inside.

The first steps inside were the hardest. The stores had just opened and there were few people, which gave me confidence. After fifteen minutes I was walking calmly. Adrián took me into a record store and let me choose an album; I picked one by a singer I’d always thought was gorgeous. He did the same in a video game store. He really was spoiling me, and I was floating. Every so often he leaned close to my ear.

—They keep staring at you —he murmured—. If they knew you had a little caged cock under that skirt, they’d shit themselves.

—There’s nothing to know —I answered—. I’m a woman.

—That you are. A very naughty woman. You have no idea how badly I want to lift your skirt and stick my tongue between your ass cheeks right here in the middle of the aisle.

At one point I had to go to the bathroom. I went into the women’s room with my heart in my mouth. It was the first time. I had practiced at home, but there, locked in the stall and dressed as I was, I got so turned on that if I hadn’t had the cage I would have touched myself right then and there. I ran a finger over my underwear, squeezed the cage, felt it straining against the plastic, unable to grow. When I came out, Adrián came up to me and whispered in my ear that by the end of the day I was going to be a complete little lady, properly used. I told him I already was. He smiled, wickedly.

To kill time we went into the movie theater. It was a horror film, I don’t remember which; all I remember is that Adrián spent the whole two hours touching me. My legs, my thigh, his hand slipping under my skirt, his fingers trying to get into my bra to pinch my nipples until I bit my lip. In another place I would have let him, but there we could get into trouble, and every time his hand wanted to go further I pushed it away. That seemed to make him even hotter. At one point he opened his pants and took his cock out under the glow of the screen. It was hard, thick, the tip shining. He took my wrist and put it in my hand.

—Suck it —he whispered—. Nobody can see here.

—No.

—Or do you prefer I stick a finger up your ass?

—No, don’t start. I’m going to get turned on and the cage hurts.

—Then lift your skirt. Let me see.

—Fine. But then watch the movie.

I half obeyed him: I hiked up my skirt, pulled my panties down enough for him to see the pink cage squeezing me, and he masturbated beside me without taking his eyes off me, pumping slowly, until I told him to put his cock away or I was going to go insane. He laughed and settled down, but he didn’t let go of my thigh for the rest of the movie.

***

When we left, he bought me an ice cream. There were more people now, but I wasn’t nervous anymore. He took me to the arcade and won me a plush toy from a claw machine. It was six o’clock when he said we were going somewhere else. I thought of a hotel. He took me to a park.

It was the big park in the center, where people go out walking and exercising. We wandered for a couple of hours while he told me things about his youth, about how when he was young he used to come to that same place at night.

—Over there, against that tree, someone like you sucked me off once —he said, nodding toward it—. Really delicious. On her knees in the grass, she swallowed it whole, all the way to the balls. I ended up coming on her face and she stayed there, licking up whatever dripped down.

—Did you bring me here for that? —I asked.

—No. I’m just giving you advice. In case one day you come here with someone.

—I don’t like guys my age —I said.

—Why not?

—I don’t know. I like older men more, like you. Men who take me to nice places and then fuck me properly.

—You’re something else —he said, laughing—. All dressed up like this, with the cage on, walking around with a man twice your age. You must already be dying to get fucked, huh?

—Honestly, yes —I admitted—. Since this morning. I want to suck you to the back of your throat, I want you to fuck me again with nothing on, no condom, like last time. I want to feel you explode inside me.

—Hold on a little longer —he said, his voice rough—. And I’ll do all that to you, and more.

I was so horny I no longer cared where we were. But he said there was one last place. He took me to a lookout at the top of the city, a tourist spot where you can see everything. At that hour the wind was blowing and lifting my skirt; mortified, I held it down while he smiled. It was almost empty. Adrián hugged me from behind and I felt his hard cock rubbing against my ass, barely separated by his pants and my panties, searching for the gap between my cheeks.

—Did you like the day? —he asked, biting my earlobe.

—Yes. My first full day as a woman out on the street.

—Wouldn’t you like to be like this all the time?

—Honestly, yes. I felt comfortable. Free.

He started kissing me, his hand again under my skirt, two fingers moving my panties aside and rubbing my asshole over the wet fabric of my own saliva. I was about to bend down when he stopped me.

—Not here —he said—. Tell me something: do you think I’m a pervert?

—A little —I answered, honestly.

—Why?

—Because you love having me at your mercy. Touching me, taking me from place to place, deciding for me. Pulling your cock out in the movie theater and making me watch.

—That’s right —he said—. And you love driving a man crazy. You know what they want and you use it to your advantage.

—Maybe —I admitted—. I get turned on when I’m treated like this. When they make me feel like a woman. When they spread my legs and use me.

He gave me another kiss and a hard slap on the ass that echoed in the empty lookout. He told me to get in the car. It was almost midnight; I thought we still had plenty of time for a hotel. The surprise came when I saw that he had taken me to my house.

—What are we doing here, baby? —I asked—. There’s a hotel four blocks away, let’s go.

—Last time you said you’d invite me to your bed —he replied—. Are you going to keep your word?

—It’s just that my parents are there, my sisters, I don’t know...

—They’re probably asleep. Go check.

I was so turned on that I agreed. I got out and ran to the entrance. The ground floor was dark and silent. Upstairs, the same. I felt enormous relief: they were asleep. I went back to the car and signaled him. We went in together, tiptoeing up the stairs. Under my parents’ bedroom door, I could see the glow of the TV, on but silent; I figured they had fallen asleep with it still on. Just as I was about to enter my room, my mother shouted my name from hers, asking if I’d gotten home. I froze. Adrián squeezed my arm and I reacted.

—Yes, Mom, I’m home already —I answered.

—All right —she said, nothing else.

Once inside, I closed the door and we both laughed quietly, hearts pounding. We kissed and his tongue went deep into my throat, hard, urgent. His fingers were already searching, so I knelt on the rug and unbuttoned his pants.

***

I’d wanted him all day. I yanked down his pants and boxer shorts, and out sprang his cock, hard, swollen, pointing at my face. I grabbed it with both hands, smelled it, ran my tongue from his balls to the tip in one long lick, and stuffed it into my mouth as far as I could. It wouldn’t fit all the way; it hit the back of my throat and I choked. I loosened my jaw, breathed through my nose, and pushed a little more, until I felt his balls against my chin. I stayed like that, gasping, my eyes watering, while he held my head and looked down at me. Then I pulled off, took a breath, and took him in again, this time faster, sucking hard, my tongue working the underside of the glans, my hand pumping the base.

I looked him in the eyes and he gave me a soft slap, smiling. He spat into my mouth and made me swallow. I kept sucking him, now also his balls, one by one, taking them in whole while I kept jerking his cock. After a while he slapped me again, harder, and with a look told me to get on the bed.

I lay on my back, legs open, so turned on that the cage already hurt. I went to get the key to free myself, but Adrián wouldn’t let me. He wanted to do it to me with the cage on. I begged him. He didn’t give in.

—You look pretty like that —he said, climbing onto the bed with his cock shining with my spit—. Leave it on. You know you don’t need it to come. When I put it in you, you’ll finish the same or better, dripping out your ass.

—Okay —I answered—. But do it now, fuck me, I can’t take it anymore.

He pulled my underwear down slowly, and that always drives me wild. There, in my own bed, with my parents in the next room, he had me on edge. He lifted my legs until they rested on his shoulders, spread my cheeks apart with both hands, and went down. He started with his tongue, searching me out, slow circles around my asshole, then pushing it in gently until he had it inside me. He drove it in there, wet, warm, moving it like he was fucking me with his mouth. I had to cover myself with a pillow so I wouldn’t moan. I writhed on the mattress, the cage hurt because it wouldn’t let me grow, and Adrián’s cock rubbed against my thigh, leaving a shiny trail of pre-cum.

He brought up a finger soaked in saliva and started putting it in while he kept licking. Then two. He moved them inside, scissors-like, stretching me, preparing me. I was on the verge of screaming.

—Get on all fours —he said—, facing the door. That way, if anyone comes in, the first thing they’ll see is this: your little ass open and my cock inside you.

—If you want, I’ll scream and wake them —I told him, teasing him, already in position, arching my back and sticking my ass up high.

—You want them to see you?

—I want you to see how you do it to me —I answered—. Stop rubbing yourself and fuck me already.

Without warning, he entered. He drove it in with one thrust, all the way to the hilt, and I let out a tiny cry that I instantly muffled with the pillow. I stayed there for a few seconds without breathing, adjusting, feeling his cock filling me, feeling the head bump against my deepest spot. He started moving slowly, pulling almost all the way out and sinking back in, and with each stroke he wrenched a muffled moan from me. Then he sped up. He grabbed my hips and started fucking me hard, eagerly, his balls slapping my perineum, the pink cage swinging between my legs with every thrust. All you could hear was the slap of our hips, the wet smack of lube, my broken breathing against the fabric.

He changed positions; he put me on my back again, grabbed my ankles and opened my legs wider than anyone ever had, until it hurt. He sank all the way in at once and stayed there, moving his hips in circles, digging inside me. It turned me on to see my cock locked in its cage, trapped, dripping liquid from the tip without being able to come, while his entered and left me shining, thick, red, alive. He spat on my chest, bent down, and licked my nipple while he kept fucking me.

—Do you like dressing like this? —he asked, panting, never stopping his thrusts.

—Very much.

—Why?

—Because it makes me feel like a real woman. Being opened up, being filled.

—Move in with me —he said, resting his hands on my throat, squeezing just a little—. I’d keep you like this all the time. With the cage, with the wig, with your legs open.

—Yes —I answered, without thinking.

—Well cared for, well dressed. And at night, mine. All night long, the slut you want to be.

—I want all that. And I want you to do it good, every day. Put it in me for breakfast, lunch, and before bed. Fill me with cum every time.

What I told him turned me on as much as my answers turned him on. He flipped me over again, put me in spooning position, one of my legs lifted and draped over his, and from behind he went into me again. Like that, slower, deeper, I felt every inch of him. He bit my neck, pinched my nipples between two fingers, whispered filthy things in my ear. At some point he sped up again, went rigid, and I felt his cock throbbing inside me. He came inside me, ropes and ropes of hot cum that filled my belly, and I liked the feeling more than ever, that sticky pressure staying there, then sliding down my thighs when he pulled out.

We were both exhausted, sweaty, on my bed, smelling of sex, of semen, of the flower creams Renata had rubbed on me and which were now mixed with everything else. His cock, still half-hard and shining, left a trail between my ass cheeks. Sneaking men into the house was becoming a habit. I knew they’d catch me sooner or later, but the pleasure made the risk worth it.

I put my underwear back on, feeling his cum dripping inside my panties, and walked him to the door. I watched him run to the car and ran back to my room before anyone could see me. As soon as I closed the door, I took off the cage. My cock sprang out, swollen, purple, desperate, with the foreskin tight from hours of holding back. I found the dildo and, taking advantage of what Adrián had left inside me, shoved it all the way in with one thrust. It slid in like butter through the warm milk he’d left behind. I masturbated like crazy, my right hand pumping my cock and my left hand driving the dildo deep, fucking myself, remembering everything: the whole day as a woman, the shopping mall, the movie theater with Adrián’s cock out beside me, the lookout, the man I’d brought into my own bed who had wrecked me without pulling out. It didn’t take long before I came, a burst that splashed my pleated skirt, my navel, even the wig, and I stayed there for a while, with the dildo still inside me, breathing hard.

Before going to sleep I kept thinking that maybe I was getting a little out of control. But I couldn’t help it. I wanted to feel like a woman in everything: on the street, in bed, every minute of the day. With a cock inside me, if possible, always.