Hugo Dressed Me as a Femboy on Our Last Day

The morning light filtered through the half-drawn blinds and spilled across the rumpled sheets of the hostel. It was our last day in the city. The next day we were catching 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 across my waist and his breathing slow against the back of my neck. I stayed still for a while, watching the sun trace the line of his jaw. I don’t want this to end. It had been an entire 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 husky. “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 online, and we detoured a couple of blocks to an avenue with storefronts that would have been unthinkable back home. 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’ve always wanted one on 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 take it without blinking. When he sat up again with the tiny steel ball gleaming 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 laughing at the way we were talking, fully aware of the punishment waiting for us when we got back.

“This is nothing,” he said, slurring a little, still buzzing with excitement. “The good part 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 lead me blindly along the pavement, his firm hand on my shoulder guiding me. I could hear people passing, scraps of conversation in a language that wasn’t mine, the hum of traffic. He placed me in front of something and stood silent for a second.

“You can open them now.”

In the window display, on two mannequins with young bodies, there were outfits like nothing I’d ever seen in a shop. Short skirts, long stockings, bright-colored pieces inspired by manga characters, all designed for a body like mine. Feminine and yet not. I forgot how to breathe.

It took me a moment to react. And when I did, I threw myself at Hugo and devoured his mouth, not caring about the prying eyes, discovering the strange new feeling of our two piercings knocking against each other 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 colors 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 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’m putting it on in the bathroom before boarding.”

Hugo burst out laughing.

“Just to see you put it on, I’d 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 outfits. He went straight for one: a bunny set in the exact pink of my hair. He took it off the rack and held it out to me.

“This one. Try it on.”

I blushed so hard I couldn’t move. He had to nudge me into the fitting room himself, draw the curtain, and start undressing me with a tenderness that disarmed 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 ever could.

The first piece was a pink thong, barely any fabric at all. I was too overwhelmed by what I was feeling to get hard, and Hugo carefully arranged me, tucking everything back so the bulge was practically hidden. He made me sit on the stool and, slowly, pulled a pair of long stockings of the same color up to mid-thigh, finished at the top with three white stripes. Standing again, he helped me step 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, lost in an image I’d wanted for years without ever daring to seek it out. A fine white wool sweater completed the set. And as the finishing touch, a headband with two bunny ears that he himself adjusted over my hair.

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

“It’s the best gift anyone’s ever given me,” I whispered, and I felt my eyes start to sting.

“You’re the prettiest thing I’ve ever seen in my life,” he replied, and I knew he meant it.

***

This time there was no sex in the fitting room. The moment was too perfect to ruin with haste. Just slow kisses, caresses brushing every inch of exposed skin, the ridiculous wish that time would stop so we could stay in 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 pair to us, the ones who had already walked the path we were just beginning.

The replies came almost instantly. “You look incredible,” Bruno wrote. “I want to draw you as one of my characters,” Dani asked, and I laughed out loud in 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 can 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 over the piercing.”

“We’re buying it anyway,” he said. “It’s my goodbye present.”

“And what am I supposed to give you?” I asked, getting clingy.

“I think I already know what I want,” he replied with a crooked smile that didn’t need translating.

***

We went back to the hostel with the shopping bag and the outfit packed away, though I put it on again as soon as we shut 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 there was something in his eyes that made me shiver before he even touched me.

He beckoned me over and I straddled him. We kissed for a long time, the piercings clinking together, his hands sliding up under the sweater to find my chest. He cupped my breasts in his palms, feeling my skin prickle, and lowered his mouth down my neck to my collarbone, leaving wet kisses and soft nips that drew a moan from me. I tugged at his hair, needing him closer, while my hips moved of their own accord against his lap, searching for the hardness I could already feel growing beneath me.

“You drive me crazy like this,” he murmured in my ear, his voice like a shadow. “Look at you, so pretty and so dirty for me.”

The skirt almost lifted itself when he laid me back on the mattress. He opened my legs with one hand on my thigh, slowly, like he enjoyed having me exposed. The other hand slid under the thong, first rubbing me on the outside, finding my soaked heat. I dropped my head with a gasp when his fingers pressed at my entrance, immediately slicking up with my wetness.

“Ready?” he asked, holding my gaze.

I nodded, unable to get a word out. My legs were shaking with pure desire, with the waiting, with my whole body demanding him. Hugo kissed me again, deep, while he prepared me patiently, slipping in one finger first, then two, opening me little by little until I could slide around them. I writhed beneath his hand, breathing in broken gasps, feeling every stretch in my ass, every inner brush that left me fuller and needier. When he added a third finger, a moan escaped me, shameless.

“That’s it,” he said, sucking on my ear. “I want to hear you like that when you’re letting me in.”

He turned my head slightly so I would look at him. His lips were wet, his hair tousled, his gaze dark and hungry. He pulled his pants down just enough to free his cock, hard and throbbing, thick at the base and flushed red at the tip. He rubbed it a couple of times against my entrance, sending a shiver through me.

“Don’t move,” he ordered softly.

Then he started to enter. First the head, slipping with difficulty between my muscles, then a little more, slowly, with a pressure that made me arch my back. I grabbed his shoulders when I felt the hard stretch of the penetration, my body opening to him as he filled me, centimeter by centimeter, until he paused for a moment inside me. I let out the air through my teeth, trembling with pleasure and fear, and he kissed my forehead as if he were worshipping me.

“Like that,” he whispered. “Fuck, like that.”

He began moving with cruel slowness, pulling almost all the way out and then thrusting back in to the hilt. Each drive shook me from head to toe, making the skirt bunch at my waist and the stockings brush my thighs with the motion. His hips slapped against mine with a wet sound, and the feel of his cock inside me kept dragging higher and higher moans from me, each one less containable than the last. Hugo held me by the hips to set the rhythm, deep, steady, never taking his eyes off me as if he wanted to burn my face into memory forever.

I answered as best I could, digging my nails into his shoulders, spreading my legs wider, clenching and releasing around his cock to feel it slide in better. The world shrank to that thrust, that heat, that unbearable, delicious friction. When he changed the angle and hit me exactly where I liked it most, I jerked and screamed his name, so loud I bit my lip right after.

“That’s it, fuck,” he growled, more undone now. “Tell me how I’m doing it. Tell me you like the way I’m fucking you.”

“Yes,” I panted. “Yes, like that. Harder.”

He obeyed. Not suddenly, but with more hunger. He opened me wider, stretched me better, driving in until he hit deep again and again while my breathing dissolved into little sobs. The room smelled of hot skin, wrinkled fabric, sweat, and the arousal that had us both soaked through. I could think of nothing now except him coming in and out of my body, the obscene feeling of being so available to his hands and his cock, of how good it made me feel on that very last day.

“I love you,” I gasped, and it wasn’t one of those things people say in bed. It was real.

“And I love you,” he replied, pushing even deeper, his voice breaking against my ear.

I felt the tension rise from my stomach to the back of my neck, a wave that left me breathless. Hugo noticed me starting to tremble and let one hand go to rub my chest, then slide down between my legs and press where I was already about to break. He didn’t need to do anything else. I came with a choked moan, clenching around him, my release spilling over my stomach and the white sweater. Hugo held out for one more second inside me, driving all the way in, then came too, throwing his head back with a low groan as he filled me with hot semen inside, pumping a couple of times before going completely still.

We stayed stuck together, sweaty and shaking, not pulling apart, stretching out the final heartbeat as much as possible. He came out of me slowly and the heat of his semen began to run down, mingling with my own wetness, while I kept clinging to him with my legs open and my chest rising and falling in ragged jerks.

***

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

“This time tomorrow 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 the suitcase, about the piercing that still hurt a little, about the photos we’d 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 wouldn’t ever go back. I had seen in the mirror the person I was when no one forced me to pretend, and it was Hugo who had shown her to me.

“Hey,” I said after a while. “I was serious about the plug at the airport.”

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.