My Cousin Asked Me to Dress as a Woman for Him

There are afternoons you think you’ve buried until someone digs them up with a single sentence. Mine took fifteen years to come back, and it did so at a restaurant table, spoken by the last person I ever would have imagined.

But for you to understand what happened that night with my cousin, I have to tell you first how it all began. How I became who I am when I let myself be.

I was nineteen, almost twenty, when I discovered what I liked. I’d been chatting for months with Marlene, an older trans woman than I was, whom I met in the stupidest possible way, on a forum, and who became a kind of mentor. She was the one who taught me to do my makeup without looking like a clown, to walk in heels without twisting my ankles, to choose the lingerie that made me feel like someone else. Wigs, lingerie, a skirt tucked away at the back of the closet. A secret life that fit in a shoebox.

That spring, my father asked me for a favor. My grandfather had hired two bricklayers to rebuild a wall in the back patio that had collapsed in the rains, and he needed someone at the house while the work lasted. My grandfather couldn’t stay there all day, and I was the idle grandson, the one who studied halfheartedly and had no schedule. It fell to me.

The morning the work began, my grandfather left me money to pay the two men, told me there was food in the fridge, and went off to his business. Fifteen minutes later the bricklayers arrived. I took them to the back patio, showed them where the materials were, and left them to work. I went back to the kitchen not knowing what to do with so many hours ahead of me.

Boredom drove me to my grandfather’s computer. I opened the chat and there was Marlene, online, as usual. We said hello and, little by little, the conversation drifted where it always drifted. She ratcheted up the heat with every message, and I answered with my heart pounding in my chest. At some point she threw down a challenge: that I should dress as a woman for as long as the workers were in the house. After all, she said, they were two strangers I’d never see again.

It didn’t take me long to decide. I took out my secret box, locked myself in the bathroom, and transformed. Short skirt, a fitted blouse, my favorite brown wig, lips painted. I looked at myself in the mirror and for a while forgot everything else.

I was still texting Marlene, already dressed, when I heard the front door open and shut. People came into my grandfather’s house all the time: other grandchildren, some uncle dropping by to say hello. I peeked into the living room and saw no one. I thought I’d heard wrong, or that it was one of the bricklayers going out for more materials. I went back to the computer. I told myself that if they found out, it might even be fun. That was the horniness Marlene had put in my head.

A couple of hours passed. The master bricklayer, the older of the two, came into the living room to tell me they were almost done. He froze when he saw me. He opened his mouth and said nothing, only gestured for me to follow him into the patio and check the wall. Still playing the part, I walked behind him as if it were the most natural thing in the world, my skirt brushing my thighs with every step.

They showed me the finished work, gave me the usual care instructions. “Everything looks good,” I said, and I led them back through the living room to pay them. Along the way, in the reflected glass of the dining room cabinets, I saw them staring at my ass without even trying to hide it, elbowing each other and laughing under their breath.

I handed them their money. Something in me didn’t want them to leave just yet.

“Anything else I can help you with?” I asked, coquettishly.

“No, that would be all,” the older one said, and then quickly added, “Sorry… do I call you young man or miss? It’s just that a little while ago you didn’t look like this.”

“Miss is fine,” I replied. “People don’t call me that much and it feels nice.”

“And why don’t they call you that? You look gorgeous as a young lady.”

“Thanks, sweethearts, you’re very gentlemanly. It’s just that most of the time they see me in men’s clothes. I don’t go out like this often.”

They kept up the compliments, each one less innocent than the last, until the younger one worked up the nerve to ask me, with a crooked smile, whether I was still “quite the little lady.” The insinuation was clear, and instead of offending me it lit me up like a match.

“Truth is,” I said, holding his gaze, “the people who know me like this say I’ve got very little lady in me. I’ve got a mouth, I’ve got an ass, and I’ve got desire. Is that enough for you?”

It was like giving an order. The two of them came at me at once. The older man grabbed the back of my neck and crushed his mouth to mine, tongue and all, tasting of cement and cigarettes, while the younger one got behind me and shoved his rough hands up under my skirt, squeezing my ass over the lace thong I was wearing. I felt him yank my underwear down hard and spread my cheeks with his fingers, without asking permission, without saying a single word.

“Look at that little ass, damn it,” he said to the older one, laughing. “It’s tastier than my old lady’s.”

They pushed me until I bent over the back of the sofa, my skirt hiked to my waist and my ass bare. I heard two belts unfastening at the same time, two zippers coming down, and when I turned my face to look over my shoulder I almost choked. The older one had a thick, dark cock, veins standing out, and he was already stroking it while staring at me like he was about to split me in two. The younger one had a longer, thinner one, curved upward, the tip gleaming.

The younger one stood in front of me, grabbed my wig, adjusted it so it wouldn’t fall off, and pressed his cock to my painted lips.

“Open up, princess. Let’s see if you really know how to suck it.”

I opened my mouth and took it in one go. I tasted the salty tip, smelled the sweat in his groin, felt the rough hairs scraping my nose every time he shoved my head all the way down. My eyes filled with tears, my mascara ran, and even so I kept sucking, choking, sucking his balls when he let me breathe, licking his cock from base to tip the way Marlene had taught me in hours and hours of conversation.

Behind me, the older one spat between my cheeks and shoved two thick fingers into me at once. I cried out with a mouthful of cock. The fingers went in and out, opening me up, while he chuckled under his breath.

“This ass was made for getting fucked, baby. Nice and tight and nice and hot.”

I felt the head of his cock press against my entrance and push, without any further warning. It hurt. It hurt a lot, because it was thick and because I was dry despite the spit, but I wanted it like that, I wanted him to open me up, I wanted to feel him shove it all the way in until his balls were buried against my ass. When he finished getting it in, he stayed still for a second and then started fucking me with slow, deep thrusts, gripping my waist, making me take the younger one’s cock in my mouth to the rhythm he set.

“Look at the little faggot getting off,” the younger one said, grabbing my hair. “Take it all down your throat, don’t be lazy. Show us how much you like cock.”

I was moaning around a mouthful of cock, eyes swollen with tears, my own dick hard beneath the skirt, rubbing against the sofa. No one had ever fucked me like that in my life. No one had ever used me the way they were using me in that moment: a mouth and an ass, two holes to empty themselves in, and I begging for more with every moan.

At some point they switched. The older one pulled his cock out of my ass, sat down on the sofa, and lifted me on top of him. I sank down onto him myself, facing away from him, with my skirt spread open like an umbrella around my hips. I started bouncing on his cock like a bitch in heat, feeling it all the way in my stomach, while the younger one got between my legs and forced my ass open wide so he could push into me too. I felt both tips pushing at the same time, the older one already inside and the younger one forcing his way in beside it.

“Wait, wait, not like that…” I managed to beg.

“Shut up, slut, take it like a good girl,” the younger one answered, spitting on my ass and pushing again.

When the second cock entered, I felt like I was being split in two. I screamed with my mouth against the older one’s shoulder, biting his shirt so I wouldn’t wake the neighbors. And then it wasn’t pain anymore. It was something else. It was both cocks moving inside me at the same time, brushing against each other separated only by my own flesh, fucking me so deep I no longer knew where one ended and the other began. I came without touching myself, my cock fluttering beneath the skirt, spattering my own white blouse. Not the wig, not the makeup, not the whole outfit: nothing hid what I was in that moment, a female getting properly fucked by two men.

The older one came first. I felt him swell inside me and unload shot after shot of hot cum, growling against my ear, “I’m filling you up, slut, all of it.” The younger one held out a little longer, pulled me off the other, threw me to my knees on the floor, and finished on my face, smearing my mouth, my eyes, my wig with a thick, abundant load that ran down my chin to my fake tits.

“Suck it, don’t leave a single drop,” he ordered, shoving it back into my mouth so I could clean it off.

When they left, they pulled up their pants, took their money, and walked out laughing as if nothing had happened. I stayed sitting on the kitchen floor, stockings bunched, skirt stained, one man’s semen dripping from inside my thighs and the other’s drying on my face, trembling, certain that no one in the world would ever find out what had happened between those walls.

I was wrong.

***

Time passed. I crossed thirty without noticing, with a more or less orderly life and my secret well hidden, taking it out only when I could do so without risking anything. Until one day I got a Facebook friend request from Damián, a cousin of mine, the son of my father’s younger sister.

Damián was twenty-two, just starting his first office job, still in one of those entry-level positions where you do everything and get paid little. We’d seen each other at a family gathering not long before; I liked him, but nothing extraordinary. Over messages, though, he became persistent. When were we going to eat together, his office was nearby, don’t be like that. I brushed him off several times, until one afternoon, not to seem like an asshole, I said yes.

The meal was normal. Family talk, work talk, nothing in particular. Just when I was thinking of asking for the check, Damián lowered his voice and dropped the question that split the afternoon in two.

“Hey… do you still dress up like a girl?”

My blood ran cold. I had to ask him to repeat it, not because I hadn’t heard him, but because my brain refused to process it. Damián played with his glass for a moment before explaining.

“The thing is I saw you once,” he said, without looking up. “At Grandfather’s house. I came in with my mother and nobody noticed I’d entered. I saw you dressed as a woman, you looked… incredible. I’d never seen a transvestite in my life. I got curious and followed you and the bricklayers. I saw everything. I saw what happened in the living room.”

The restaurant suddenly became too quiet. Fifteen years. For fifteen years, that memory I thought was mine alone had also lived in my cousin’s head, hidden the way mine was.

“I didn’t know you were there that day,” I managed to say.

“Nobody knew. And ever since then…” He swallowed. “Ever since then I’ve had a fantasy. I want to propose something to you. I want you to dress up for me. I want to fuck you like they fucked you. I want to put it in your mouth and your ass until your wig falls off.”

I put down my fork. I felt my face burn.

“How can you even think of that? We’re cousins, Damián. That’s not something you do with family.”

“I’ve thought about it a lot,” he replied, more confidently than I expected. “And I don’t see anything wrong with it. It’s not like anything can happen, you can’t get pregnant, can you?”

“No, of course not, but… wouldn’t it be weird afterward? At family gatherings, at Christmas, seeing each other’s faces?”

“You hardly ever go to the gatherings,” he said, with a half smile. “But okay, if you don’t want to, I understand. I don’t want to force you into anything. It’s just that I really like that side of you. I always did. I’ve jerked off thinking about you ever since then, cousin. Thousands of times.”

That was where the conversation ended. We paid, said goodbye on the sidewalk with an awkward hug, during which I could clearly feel his hard cock pressing against my hip, and each of us went our own way. But the seed had already been planted.

The following days were a delicious torture. The more I told myself it was madness, the more the filth grew. Forbidden things have that effect: you tell yourself no, and “no” becomes the only thing you can think about. And there was something else, something I found hard to admit. Damián was the only member of my family who had really seen me, who knew my secret and not only accepted it but desired it. That idea undid me. I touched myself in bed thinking about him, about his cock pressing against my hip, about the look on his face when he had me dressed up and on my knees in front of him.

Three weeks passed before he wrote again. A cautious message, almost an apology. “Hi, how are you? Sorry for the bombshell I dropped on you the other day, I didn’t mean to make you uncomfortable.”

I read it several times. I thought about replying prudently, about closing the door once and for all. Instead, I locked myself in the bathroom, took out the box, and got dressed. Ruffled skirt, white button-down blouse, the curly brown wig, lips fully made up, the black lace thong I knew would show through. I dressed like I was going on a date and took a photo in front of the mirror, biting my lip, looking into the camera the way Marlene had taught me to look. Then I took another, from behind, bent over, with my skirt lifted and my ass pushed out against the mirror.

I sent them without any text to go with them. Just the images, and then below, a single line:

What if I could get pregnant… would you do it to me anyway, cousin?

I watched the three dots appear. Then disappear. Then appear again. And while I waited for his answer, my heart in my throat and my skirt still on, I knew I had already crossed the line I’d been pretending not to see for fifteen years.

What he answered, and everything that came after, I’ll tell you another day.