My Cousin Discovered My Crossdressing Secret That Summer

A couple of years ago I won a scholarship for an intensive language course in a city halfway across the country from mine. The scholarship covered tuition and meals, but not housing, so I ended up staying at my aunt Marisol’s place, my mother’s sister. They lived in a two-story house: bedrooms and the kitchen upstairs, a huge garage downstairs, and an office nobody used, with its own bathroom. I managed to get a secondhand mattress and, without even realizing it, I had my own little apartment with a separate entrance.

That privacy was everything to me. I’d always been a closet crossdresser, one of those people who keeps the truth hidden at the back of a drawer. As a child, whenever I was home alone, I would secretly try on my mother’s things: a lipstick, a skirt, a thong that hung on me like a tent. When I hit my teens, the desire didn’t go away; it grew. My body was never very masculine, almost neutral, except for some hips and an ass that women’s clothes seemed designed to hold up.

The first month passed without a hitch. The classes came easily to me and, with the little money I saved, I bought two thongs—one black, one pink—a cheap lipstick, and a pair of earrings. I used them alone, in front of the bathroom mirror, until I got so turned on I’d end up with my cock hard, straining against the fabric, rubbing myself over the thong until the wet spot from pre-cum dampened the cotton. I’d put on a video of a girl getting fucked from behind and imitate her moans, with two fingers in my mouth pretending I was sucking cock, the other hand tucked under the thong, working the tip with my thumb. I’d finish by jerking off into my own hand, mouth open against the mirror, feeling more feminine with every high-pitched moan that slipped out of me.

The problem with having something is that immediately you want more. Several times, when my uncles went out, I caught sight of my cousin Camila—early twenties, always wearing flirty clothes—crossing the patio in dresses that made me sigh with envy. I started craving her whole wardrobe. I didn’t dare buy women’s clothes in a store; I was terrified someone would walk in and find the bag. The little I had fit inside an old shoe at the back of my closet.

And then my chance came.

One Thursday morning, my aunt came downstairs to hand me the keys to the whole house.

“We’re going to the coast until Sunday night,” she said. “Look after it for us and eat whatever you want from the fridge, before it goes bad.”

As soon as the car disappeared at the end of the street, my mind took off. I had four whole days and a house all to myself. I wanted to do it right, do it completely. The first thing was to go to a waxing salon with a cap and a mask on, protecting my identity like it was a covert operation. The women there laughed kindly, but I didn’t care: I came out of there smooth everywhere, softer than ever, with no hair on my legs, my pussy, or my ass, and that alone was worth every cent.

I waited until I saw photos of my aunt posted from the beach, five hours away, to confirm she really was far off. Only then did I go upstairs. Camila’s room smelled like sweet perfume and cream. Everything was pink, with stuffed animals on the bed and little jewelry boxes on top of the dresser. I didn’t want to touch the neat wardrobe and leave traces, so I looked for her laundry basket. It was full: skirts, dresses, swimsuits, underwear. I tried everything on, one piece after another, posing in front of the full-length mirror. I put on one of her used thongs and felt the fabric press my cock against my pubis; just knowing that garment had been in contact with her pussy got me rock hard.

After almost two hours I stopped, took a deep breath, and said quietly to myself:

Good. Now it’s time to feel one hundred percent like a woman.

I chose a short black dress with an open back and long flared sleeves. I went downstairs to shower, put on only the pink thong, painted my lips, and brushed my hair, which isn’t long but is wavy and falls to my neck. I went back up, slipped the dress over my head, and felt the fabric cling to my hips. I finished the look with a headband, some sparkly earrings, and, from my aunt’s room, a pair of black patent heels.

I walked slowly all through the house so I wouldn’t twist my ankles, for almost an hour, stopping at every mirror. I looked sexy, with white, firm legs, the dress molding to my ass and my hair giving me a sweet, coquettish air at the same time. When I’d finally had my fill, I put everything back where it belonged and went down to my room euphoric. That night I masturbated several times on the mattress, still wearing the pink thong, pulling it aside to spit on my fingers and finger my ass for the first time with two knuckles. I came groaning the word “slut” into the pillow, feeling hot semen soak my navel, and started again barely half an hour later, this time face down, ass up, rubbing my cock against the sheet while one of my fingers went in and out of my back pussy to the rhythm I imagined from a cock that wasn’t there.

***

I was jolted awake by the sound of the garage gate. It was twelve-thirty; I’d slept half the day. I peeked through the blind and saw a car I knew well: it was Mateo, another one of my cousins, the oldest. He got out, crossed the garage, and came straight to my door. I jumped away from the window, because I was almost naked, wearing only the pink thong from the night before.

“Adrián, are you there?” he knocked.

I stayed silent for a second too long.

“Mateo? Sorry, I just woke up,” I answered, trying to sound normal.

“I left a package at your door. Pick it up whenever you can.”

I waited to hear his footsteps heading up the stairs before opening it. There was a black bag on the floor. I picked it up, opened it, and almost fainted: inside were printed photos of the inside of the house from the night before, with me wearing Camila’s dress. In one I was sitting cross-legged on the sofa; in another, in front of the mirror; in another, hands on my hips.

My phone vibrated. It was him.

“I check the cameras from my phone when no one’s around. Don’t freak out, this stays between us,” he wrote. And a second later: “I’ve been wanting to tell you something for a long time and never knew how.”

Inside the big bag was another smaller one. I opened it with clumsy fingers: a red lingerie set, thong, bra, garter belt, and a pair of sheer stockings. Another message came through.

“I like guys like you, guys who keep that secret hidden away. If you like me too, put it on and I’ll come down. If you’d rather I forget all this, tell me and we’ll never mention it again.”

I sat on the edge of the mattress, my heart racing. This wasn’t a threat; it was an open door. And the truth, shameful and freeing at the same time, was that for weeks I’d been watching him in secret, measuring the bulge in his pants every time he sat down to eat. I typed one word before I could change my mind.

“Yes.”

***

I took a shower, washed up, and put on the red lingerie piece by piece. I fixed my hair, touched up my lipstick, and waited, for nearly forty endless minutes, until someone knocked on the door. I opened it slowly. Mateo was there, shirtless, looking me up and down.

“Turn around,” he said softly.

I turned for him. I heard him suck in a breath through his teeth.

“Fuck, what an ass,” he murmured. “I’ve been imagining this for months and I still undershot it.”

“Are you sure about this?” he asked after that, and the fact that he asked me melted me more than anything else.

“Sure,” I answered, deliberately choosing the feminine form. “I want you to fuck me.”

He came in and closed the door. He stood behind me, pressed his chest to my back, and started kissing my neck, slowly, while he whispered that this would be our secret. I felt his hands travel over my waist through the fabric, rise to squeeze my nipples through the red bra, then drop back down and slip under the thong from behind to knead my ass. He spread my cheeks with his fingers and ran his fingertip between them, barely brushing my hole, and I let out a high little moan, very girly, that pulled a rough laugh from him against my ear.

“That’s it, just like that,” he told me. “Keep moaning like a slut.”

He made me turn again, this time to face him, and kissed me on the mouth for the first time. His tongue came in without asking, looking for mine, while one of his hands slid down my stomach and squeezed the hard lump under the red thong. He rubbed it slowly, smiling into the kiss when he felt the pre-cum dampening the fabric.

“Look at you,” he said. “Already wet.”

“Sit on the bed,” he murmured after that, pushing my shoulder.

I obeyed. He undressed in front of me without rushing, yanked his pants and boxers down in one pull, and stood there, letting me see him fully before coming closer. My mouth went dry. He was thick, long, with a red tip and a vein running clearly from top to bottom, a couple of bright drops already beading on the glans. I closed my eyes for a second, then opened them because I wanted to look. He came closer, took my hair firmly, and pressed his cock against my painted lips.

“Open,” he ordered.

I opened. I started slowly, with my mouth, sucking just the tip first, teasing it with my tongue, tasting the salty flavor of pre-cum. He let out a deep moan and pushed deeper into me. I sucked him down all the way, kissing my way along the shaft, taking him with a flat tongue, swallowing him to the throat until tears slipped from the corners of my eyes and the red lipstick smeared at the corners of my mouth. I slobbered all over his cock; I could feel threads of saliva dripping onto my red bra.

“Look at me,” he asked.

I looked him in the eyes and didn’t look away while he fucked my mouth to his rhythm, holding my nape with one firm, gentle hand. His breathing turned heavy, and now and then a half-smile slipped across his face. I let myself be guided, attentive to every sign of what he liked, hollowing my cheeks, squeezing his balls with one hand while the other shoved two fingers into my own mouth beside his cock. I felt desired in a way I’d never experienced dressed as a man.

“Like that, while you keep looking at me, swallow it all,” he said in a husky voice, and a moment later he finished with a shudder that ran through his whole body.

I felt the first wave of hot semen hit my palate, then another and another, my mouth filling until there was no room left. I swallowed everything, every drop, while he kept himself inside me and didn’t let me pull him out, and at the end I ran my tongue over the tip to clean off the last of it. I showed him my clean mouth, without being asked, just because I wanted to see his face. He smiled.

“I fucking love you, slut,” he said simply, and the word in his mouth made my whole body shiver.

He made me lie back and took his time with me. He knelt between my legs, hiked my red stockings up to my thighs, pulled my thong aside, and just stared at my shaved ass, glistening and exposed. He lowered his head without warning and ran his tongue over my hole, long, slow, soaking me completely. I screamed, a high scream I didn’t even recognize as mine. He did it again, and again, and again, eating my ass with a hunger I hadn’t expected, pushing his tongue in as deep as he could. With one hand he worked my hard cock over the red thong, squeezing and rubbing it without letting me come.

“Please,” I panted. “Please, just put it in already.”

“Not yet,” he said against my ass. “First I’m going to get you nice and open.”

He spat on the hole, coated his fingers, and shoved the first one into me to the knuckle in one go. Then the second, curling them upward, touching a spot inside that made me arch all over. By the time the third went in I was already trembling, grinding my hips against his hand, begging for more like a whore.

He pulled his fingers out, spit into his palm, lubed his cock well, and took position. He pressed the tip against my entrance.

“Breathe,” he told me.

When he finally entered, he did it slowly, giving me time to get used to it, centimeter by centimeter, watching my face the whole time. I bit the pillow, half from the burn of being opened up, half to keep from screaming with pure pleasure at the way each inch of his cock filled me inside. When he’d finally buried it to the balls, he stayed still for a few seconds, breathing against my neck.

“You’re so fucking tight,” he whispered. “You’re milking my cock.”

He started moving, pulling almost all the way out and then burying it in me again slowly, marking every thrust. I spread my legs wider, hooked the red stockings at the small of his back, and begged him in a broken voice to go harder. He obeyed. Every time he drove into me all the way, I let out a new moan, higher, more feminine, and he licked his lips as he looked at me like I was the best pussy he’d ever fucked.

In the middle of it all my phone rang on the nightstand. It was my aunt. Mateo handed it to me with a wicked smile and stayed still, his cock buried to the root, while I, with the steadiest voice I could fake, assured her everything was fine, that her son had stopped by to say hello, that nothing was wrong. Right when I said that, he gave a small, malicious shove, sinking me an inch deeper, and I had to bite my lip until I drew blood so I wouldn’t moan into the phone. I hung up shaking, half laughing and half panicking.

“Shall we keep going?” he asked against my ear.

“Don’t you dare stop,” I answered. “Fuck me like I deserve.”

He pulled his cock out, flipped me face down in one jerk, lifted my hips with both hands, and slammed back into me in one stroke. I grabbed the sheet in both fists. He sped up and the room filled with sounds I had never made: my high moans, his low grunts, the slap of his balls against my ass, the wet noise of his cock sliding in and out. With one hand he held me by the hair, with the other he landed a sharp smack on my ass that left a red mark beside the garter belt.

“Tell me what you are,” he panted.

“Your slut,” I blurted without thinking. “I’m your slut, Mateo, don’t stop.”

He slipped a hand underneath, grabbed my cock dripping pre-cum into the mattress, and started jerking me off at the same rhythm he was fucking me. I didn’t last long. I came screaming into the pillow, in long spasms, squeezing his cock inside me with every wave, soaking his hand with semen. He held on for two, three, four more thrusts, each one more brutal, until he wrapped his arms around me, pulled me tight against his chest, and I felt his whole body tense, felt his cock swell one last time inside me and spill shot after shot, filling my ass with hot cum to the end.

He stayed still for a few seconds, breathing into the back of my neck, then slid out slowly. I felt his load trickling down the insides of my thighs, wetting the edge of the red thong. He collapsed beside me on the mattress, both of us out of breath, my face buried in the sheet and a stupid smile I couldn’t wipe off. He ran two fingers through the trail running down my leg, lifted them to my mouth, and I sucked them without thinking twice.

***

Later, in the bathroom, I looked at myself in the mirror: hair disheveled, lipstick smeared, red stockings marked into my thighs, a white thread of his semen still peeking out from between my ass cheeks. I got into the shower still dressed and let the water run for a long time, processing what had just happened, what I had just discovered about myself and about him. There was no fear. Only a strange, new calm, and a tingle between my legs that was already asking for more.

When I got out, there was a message from him waiting for me.

“I deleted the recordings. I don’t want you carrying that around. But if you want, this doesn’t have to end here.”

I read it twice. That sentence, more than any caress, was what completely undid me. For the first time in my life someone had seen the girl I kept hidden at the back of the closet and, instead of mocking her, had wanted her, had fucked her, had filled her with semen. I replied without overthinking it.

“Whenever you want.”

That same week I went back up to his room, this time invited. And I no longer needed to borrow anyone else’s clothes: we started buying mine, together, piece by piece, as if building my wardrobe were our own shared secret.