Hugo Dressed Me as a Femboy on Our Last Day

Morning light came filtered through the half-lowered blinds and fell across the rumpled sheets of the guesthouse. It was our last day in the city. The next day we were taking the flight back home, and we both knew it, even if neither of us had wanted to say it out loud yet.

Hugo was still asleep beside me, one arm draped over my waist and his breathing slow against the back of my neck. I lay still for a while, watching the sun sketch the line of his jaw. I don't want this to end. It had been a whole week stolen from our families, who were more concerned with last-minute shopping than with where their sons were.

When he finally opened his eyes, he smiled with that lazy just-woken-up look of his.

—I’ve got plans for today —he murmured, his voice rough—. Things we can only do here.

—What kind of things? —I asked, turning to face him.

—Surprise. Get dressed.

***

We went out into the street with the dry autumn cold biting at our ears. Hugo had pulled up a list of places from the internet, and we detoured a couple of blocks to an avenue lined with shop windows that back home would have been unthinkable. Our first stop was a small tattoo and piercing place, with the walls covered in prints and the smell of ink and disinfectant in the air.

—I always wanted one in my tongue —Hugo said, rubbing his hands together—. In Spain they won’t do it at my age. Here they will.

I watched him lie back on the chair, open his mouth, and hold still without blinking. When he sat up with the tiny steel bead glinting between his teeth, he looked at me with one eyebrow raised, daring me. I didn’t think twice. The anesthetic left my tongue numb and clumsy, and we left both of us laughing at the way we were talking, fully aware of the punishment waiting for us when we got back.

—This is nothing —he said, dragging out the words, still buzzing—. The good stuff is coming now. You’re going to love the next place.

—More than an illegal piercing?

—Way more. You’re going to freak out.

***

At the corner he asked me to close my eyes. I did, letting him guide me blind along the sidewalk, his firm hand on my shoulder steering me. I could feel people passing by, scraps of conversation in a language that wasn’t mine, the hum of traffic. He set me down in front of something and stayed silent for a second.

—You can open them now.

In the shop window, on two young-bodied mannequins, there were outfits unlike anything I’d ever seen in a store. Short skirts, long stockings, bright-colored pieces inspired by manga characters, all designed for a body like mine. Feminine and yet not. I ran out of breath.

It took me a while to react. And when I did, I lunged at Hugo and kissed the hell out of him without caring about the staring eyes around us, discovering the new and strange sensation of our two piercings knocking together between our tongues.

—How did you know…? —I started, but I didn’t finish the sentence.

—Because I know you —he said simply.

***

Inside, I didn’t know where to start. I moved quickly down the aisles, touching everything, dizzy from so many clothes: panties cut to conceal, sets in vivid tones with animal and character motifs. Hugo, calmer, let me wander for a while and then took me by the elbow to the back section, where toys were mixed in with harnesses and straps.

I picked up a plug with a fox tail and held it up to him.

—If this gets through airport security, I swear I’ll put it in on the bathroom before boarding.

Hugo burst out laughing.

—Just to see you put it in, I’d be willing to risk it. But if they make me take it out of the suitcase at security, I don’t know what face my mother’s going to make.

We went back to the sets. He went straight for one: a bunny model in the exact pink of my hair. He took it down and held it out to me.

—This one. Try it on.

I blushed so hard I couldn’t move. He had to push me into the fitting room himself, draw the curtain, and start undressing me with a tenderness that undid me, as if I might break. When I was completely naked, he kissed me. A soft kiss, unhurried, saying “trust me” better than any words.

The first piece was a pink thong, barely any fabric at all. I was too overwhelmed by how I was feeling to get hard, and Hugo positioned me carefully, tucking everything back so the bulge was practically hidden. He made me sit on the stool and, slowly, pulled long stockings of the same color up to mid-thigh, finished at the top with three white stripes. Back on my feet, he helped me into a short flared skirt, pink with white trim, ending exactly where the stockings began.

I couldn’t stop looking at myself in the mirror while he dressed me, absorbed by an image I had wanted for years without ever daring to seek it out. A fine white wool sweater completed the set. And as a finishing touch, a headband with two bunny ears that he adjusted himself over my hair.

Hugo stepped back and looked at me in the reflection with a smile so wide it barely fit his face. I had folded in on myself, arms tucked over my chest, overwhelmed by emotion.

—It’s the best gift anyone’s ever given me —I whispered, and I felt my eyes clouding over.

—You’re the most beautiful thing I’ve ever seen in mine —he replied, and I knew he meant it.

***

This time there was no sex in the fitting room. The moment was too perfect to spoil with haste. Just slow kisses, caresses grazing every inch of bare skin, the ridiculous wish that time would stop so we could stay inside there for the rest of the day.

Without thinking, I took a photo and sent it to the group chat we had with Bruno and Dani. Bruno plays basketball in an overseas league and lives with Dani, who draws, and the two of them had become a kind of older-brother figure to us, the ones who had already walked the path we were just beginning.

The replies came almost immediately. “You look incredible,” Bruno wrote. “I want to draw you for one of my characters,” Dani asked, and I laughed out loud inside the fitting room.

—I don’t want to take this off —I told Hugo in his ear.

—Then don’t take it off. We’ll pay for the set and you’ll leave wearing it.

—You’re insane. If I show up like this in front of my mother, she’ll lose it. I’m already going to have enough to deal with because of the piercing.

—But we’re buying it anyway —he said—. It’s my goodbye gift.

—And what do I give you? —I asked, getting soft on him.

—I think I already know what I want —he answered with a crooked smile that didn’t need translating.

***

We went back to the guesthouse with the shop bag and the outfit packed away, though I put it on again as soon as we closed the room door. Hugo sat on the edge of the bed and watched me cross the room, the skirt swaying, the stockings taut over my thighs, and in his eyes there was something that made me shiver before he even touched me.

He beckoned me over and I straddled him. We kissed for a long time, our piercings clacking, his hands sliding up beneath the sweater until they found my chest. He laid me down slowly, pulled the thong aside without taking it off completely, and prepared my entrance patiently, slick fingers opening me little by little while he spoke softly in my ear.

—Look at you —he murmured—. I’ve wanted to do this all day.

When he finally entered me, he did it slowly, holding back, attentive to every expression on my face. I arched against him, clutching his shoulders, the skirt bunched up to my waist and the stockings brushing his sides with every thrust. It wasn’t wild. It was slow, deep, charged with something that felt far too much like goodbye. He pushed all the way in and stayed there for a second, feeling me, before starting again.

—I love you —I panted, and it wasn’t the kind of thing people say in bed. It was real.

—And I love you —he answered, speeding up only a little, his hand closing between my legs in the same rhythm.

We came almost at the same time, him emptying inside me with a muffled groan against my neck, me spilling over the white sweater that would never be truly clean again. We stayed pressed together, sweaty and trembling, not separating, stretching out the last heartbeat as long as possible.

***

Afterward we lay wrapped around each other on the unmade bed, me curled against his chest, him tracing circles on my back with his fingertips. Through the window, the sky was beginning to turn orange over the rooftops of a city we wouldn’t walk together again for a long time.

—Tomorrow at this time we’ll be on the plane —I said.

—I know. But we’re taking this with us. —He squeezed me a little tighter—. Literally, in your case.

I laughed against his skin. I thought about the set folded in my suitcase, the piercing that still hurt a little, the photos we would keep without showing anyone. I thought about how we’d go back to our usual lives, to our families and punishments, but that something had changed and would never go back. I had seen in the mirror the person I was when no one forced me to pretend, and it had been Hugo who showed him to me.

—Hey —I said after a while—. I was serious about the airport plug.

Hugo laughed so hard the bed shook, and he kissed my forehead with his lips still curved.

—We’ll see what face you make at security —he said.

And we stayed like that, tangled together, while the light slowly faded over our last day.