My Best Friend Was Hiding That He Dressed as a Woman

We were at the entrance to the movie theater, and the time had come to pay for the tickets to see the film we'd been waiting weeks for.

—Forget it —Tomás said—. I'll pay.

—How do you do it, man? Where do you get so much money? —I asked.

I didn't understand how he always had money on him. Over the past few months I'd seen him wearing new clothes and sneakers; he'd bought the latest phone, a game console, a huge television, and a gaming computer. Something didn't add up.

—Do you sell drugs? —I asked jokingly.

—Nothing like that, nothing like that —he replied, laughing.

—Then what? —I insisted.

He thought about it for a moment, as if weighing how much he could tell me.

—Let me think about it. Let's watch the movie, and then I'll tell you.

I didn't push him any further, because I knew he'd end up telling me eventually. We sat down in the theater, but I didn't pay much attention to the screen. My mind kept spinning, trying to guess what he was doing to make so much money and why he wasn't telling me, his best friend since high school.

When we came out, he started talking to me about the movie with an enthusiasm I didn't believe for a second.

—Come on, man —I cut him off—. Stop playing dumb and tell me.

He smiled.

—I sell content —he finally blurted out.

Suddenly, everything made sense.

—Oh, right… I figured it was something like that —I said—. Do you ask girls for pictures and resell them, or do you get them off the internet? What idiots pay for that stuff.

He fell silent.

—What? —I asked—. What's wrong?

—No, man. It's original content. I make it myself.

—Stop screwing around. Seriously?

—I swear. I get dressed, do my makeup, and take the pictures myself —he said, lowering his voice—. It sells pretty well. They tell me I've got a woman's body.

I looked at him, not knowing whether to laugh.

—Okay, seriously, stop screwing around —I insisted, laughing nervously.

But he kept looking at me without laughing, waiting.

—If you want, come to my house and I'll show you —he said.

I looked at him again. He was serious.

—All right —I answered—. Let's go.

***

We arrived at his house, greeted his mother, and went into his bedroom. He locked the door and asked me not to look while he changed. I sat in front of the console and started playing while, behind me, I heard him moving around, opening drawers, adjusting his clothes. The anticipation was getting to me, and even I didn't understand why.

—There —he said—. What do you think? Do I look good?

I turned around and saw him. He had put on some makeup, was wearing white stockings that came up past his knees, pink panties, and a loose white blouse. He had combed his bangs forward so that his hair covered part of his forehead. It was obvious he had every detail of the routine down.

I was left speechless, with a mixture of emotions I didn't know how to sort out. I'd never imagined seeing my friend like that, and yet something inside me woke up without permission. My cock pressed hard against my pants before I could even think.

—Wait —I said, laughing to cover it up—. You look like you came straight from a convention.

He fell silent and slowly turned around to show me his leg and part of his ass. There wasn't a single hair on his thighs; his skin looked smooth, even smoother than my girlfriend's, who took such good care of herself.

—Seriously, you've got a woman's body —I admitted.

—Touch it, go on —he said, laughing—. It's okay.

I hesitated. I wanted to, but something held me back: fear of what it might mean, of what he might think of me afterward.

—What's wrong? —he said when he saw I wasn't moving—. Are you scared? It's just touching.

He had a small, firm ass, with flawless white skin. His panties were a little loose and had ridden slightly between his buttocks, outlining the crack.

—All right, fine —I gave in.

And although I wanted to do it far more than I dared admit, I only managed to lay my hands on his buttocks. The fabric was thin, and beneath it I could feel the warm flesh, yielding softly under the pressure of my fingers.

—See? —he said—. Nothing happens. Do you like how I keep it?

—I'm getting hard —I replied, laughing nervously.

—You're such a pervert —he laughed—. Do you understand now why they pay me so much?

—I see, I see… Give me your username; now I want to subscribe —I joked.

—No, idiot —he laughed—. But I've got all the material on the computer. If you want, I'll show you.

—Go on, show me.

He started moving his hips in circles, as if dancing, rubbing against my hands, which I'd left still on him. With each turn, the fabric of his panties sank farther between his buttocks, and I could feel my cock growing hard at a pace I could no longer hide.

—What are you doing? —I asked, my voice tight.

—Nothing… nothing… it's just a game.

I couldn't hold back and squeezed his ass with both hands. It was soft, perfect, spilling over my fingers. I pulled the fabric upward, and his panties wedged into the crack like a string, leaving his buttocks exposed at the sides. My cock grew completely hard inside my pants, to the point of hurting.

—Is this how you want me to grab you? —I said, kneading his ass hard and spreading it with my palms.

He blushed, and his breathing quickened. He pushed his ass backward to press himself harder against my hands, seeking even deeper touches.

—Show me the pictures —I asked, trying to regain some control.

—They're on the computer —he said, restraining himself—. Sit in the chair.

***

I let go of his ass and sat down. The screen was already on.

—What's the folder called? —I asked.

—Wait, I'll open it.

I watched him detour first toward the dresser, take out a feminine perfume bottle, and dab a couple of drops on his neck.

—Let me show you —he said, sitting on my lap.

The little bastard smelled like flowers, like something sweet I couldn't put a name to. I felt the warm weight of his ass flatten against my bulge, right over my hard cock, and all I could do was smell his neck while he searched the screen. The faint smile on his face told me he'd gotten exactly the effect he wanted. He moved just slightly, a minimal rocking motion, rubbing against me as if he didn't realize it.

—Here they are —he said.

A folder packed with images appeared on the screen. He opened the first one and went through them one by one with his fingertip. I was absorbed, watching his poses, how good he looked, how natural everything seemed. In every picture, he played at hiding what he had between his legs while making perfectly clear what he was concealing. Everything about him looked feminine, but what aroused me most was the possibility that he might reveal the masculine part at some point, something that never quite happened. Without realizing it, he was making me want to see it, and the desire grew until it became unbearable.

—You never show it? —I asked.

—Do you want to see it? —he replied with another question.

We remained still and silent.

—Yes —I admitted—. I want to see if it's bigger than mine.

He moved his hips, rubbing against the bulge in my crotch, pressing his ass against my cock and tracing every inch of my erection through the fabric of my pants.

—I don't know if it's bigger than yours —he said—. I think yours is big.

He stood up and bent forward, leaving his ass at face level. His pink panties framed his white buttocks, and along the edge, the pink line of his asshole showed just barely.

—Pull my clothes down —he said.

With both hands I grabbed his panties and pulled them down to mid-thigh. He turned around, placed one hand on his waist, and raised one foot onto my thigh, leaving his erect cock in front of my face. His balls hung small and hairless, and his cock quivered, pointing upward, its shiny tip beaded with moisture.

—What do you think? —he asked.

It resembled mine, though the tip looked slightly more prominent, with a pink, thick head and not a hair around it. It was so close that I could feel its heat on my face, along with the mingled smell of clean skin and perfume.

—It looks like mine —I said, my mouth dry.

—Let's see… —he replied, lowering his foot—. Show me yours.

I unfastened my belt and pulled my pants and underwear down to my ankles. I was hard, pointing upward, thick and heavy, with the vein standing out from top to bottom.

—Yours is hairy —he said—, and really hard.

—Yeah —I replied, lowering my eyes. Despite my arousal, I felt insecure about what we were doing—. What do you want me to say?

—Do you want me to help you with that? —he said, lifting my face with a finger beneath my chin.

I looked at him without finding the courage to admit aloud what I wanted. I was afraid someone would find out. Afraid of what people would think of me.

—No one is going to find out —he said, looking into my eyes.

I nodded.

***

He smiled and, without taking his eyes off me, knelt between my legs. He took my cock in one hand and weighed it, as if measuring how much of it would fit, then ran his tongue from my balls to the tip in one slow lick that made me clutch my fingers against the back of the chair. He sucked the head first, taking it completely between his painted lips, then gradually swallowed it until I felt the back of his throat close around the tip. He began moving his head up and down, sucking with a technique that was anything but amateur: he tightened his lips around the shaft, let a thread of saliva run down over my balls, pulled my cock from his mouth to lick my balls one by one, then took it down his throat again.

—Goddamn… —I murmured, grabbing him by the hair—. You suck it so well, you son of a bitch.

He looked up at me from below with his mouth full, smiling with his eyes, and picked up the pace. My cock slid in and out, shining with spit, and he stuck out his tongue to lick the tip each time he pulled it from his mouth. When he felt I was about to come in his mouth, he released me, stood up, and turned around.

He spread his buttocks with his hands until the tip of my cock was between them. He rubbed me up and down against his asshole, smearing it with the saliva left on me. The rubbing left everything wet, and I felt the little hole tighten and relax with every stroke. Then he took me in one hand to guide me and slowly let me enter until I was completely inside him. I felt the tight ring open around my cock, the constricted heat of his ass swallowing every inch, and I let out a long moan that escaped before I could control it. He smelled so good that I began running my nose along his neck, getting drunk on the perfume.

He planted both feet on the free edge of the chair between my legs and crouched down, sitting on me with my cock buried inside him. He began rising and falling, rocking forward and backward, impaling himself completely, letting my cock slide almost all the way out before dropping himself down hard to the base again. Each downward motion drew a high, half-contained moan from him so it wouldn't be heard through the door. I grabbed his nipples beneath the blouse and pinched them. He squeezed his ass tightly around me, as if milking me from inside, and out of the corner of my eye I could see his own hard, naked cock bouncing in time with his riding.

—Like that, like that, fuck me hard —he panted, resting the back of his neck against my shoulder—. Break my ass, come on.

I dug my fingers into his hips and began thrusting from below, lifting him every time he rose and slamming him against my pelvis on each downward stroke. The slap of flesh against flesh filled the room, and he let himself be used, his head hanging back, his mouth open, a thread of saliva at the corner.

I can't believe my best friend is the first person I've fucked like this, I thought as I held him by the waist to match his rhythm.

He looked back, and our eyes met. It was a moment of enormous tension, in which I admitted without words that I was having an incredible time.

—Will you kiss me? —he asked submissively.

I waited a second and gave him a timid kiss on the lips that, after the initial hesitation, grew more intense. I pushed my tongue deep into his mouth while continuing to fuck him from below. I held him tightly, felt my balls tense, and suddenly began emptying myself inside him, jet after jet, filling his ass with hot cum. He squeezed his asshole around my cock as I came, milking me of every last drop.

—Ah… that's good, man… so good —I panted, still buried to the hilt, feeling my semen leak out of him and run over my balls.

Without pulling out yet, he let the weight of his back fall against my chest and stretched his legs, intertwining them with mine. My cock remained inside him, softer but still thick, lodged in his wet ass.

—Will you make me finish? —he said.

Over his shoulder I saw that he was erect, the swollen tip purple, with a thick drop of pre-cum hanging from it. More out of gratitude than arousal, I took it in my hand intending to help him, but the moment he felt my touch he started coming. I closed my fist tightly around it and stroked the shaft up and down.

—There… yes, yes —he said, arching his whole body and shooting two powerful streams that splashed onto his chest and stained his white blouse, as if the tip were about to burst.

I kept milking him until two more, thinner threads came out, sticking to his fingers and his hairless pubis. He remained panting against my neck, my cock still buried in his ass and his cum running down his belly.

When we finished, I felt somewhat guilty and left without looking back. But a few hours later it passed, and I texted him.

“That was good. Shall we do it again?”

“Come over tomorrow afternoon,” he replied, adding a lips emoji at the end.

***

The next day I arrived punctually at his door, and we repeated the same routine: he changed, put on makeup, sat on my lap, and ended up on all fours on the chair with my cock buried to the hilt in his ass. I came inside him again, and again I jerked him off until he came against the computer screen. On the third day I asked him to suck me, and he agreed without a problem; he knelt between my legs, sucked me hungrily, and when I was about to come, I shoved it down his throat and he swallowed everything without disgust, sucking my balls too so as not to leave a drop. On the fourth day I fucked him on all fours over the bed, gripping his hair and thrusting so hard that the headboard banged against the wall, while he moaned with his face buried in the pillow, begging for more. After two weeks of daily visits, we reached the point where he sucked my cock until it was shining before I put it inside him, and sometimes he asked me to come on his face so he could lick his fingers afterward. After a month I started sucking him too, though I didn't swallow: I ran my tongue along his shaft, sucked his balls, and when he was about to come, I pulled it from my mouth so he could spill onto mine.

Since he took such good care of me, my girlfriend, Carla, began complaining: she said I'd lost interest in her. And she was right, although I cared less and less. We'd agreed that when she finished her studies, we'd tell everyone we were together and become a proper couple. But things sped up long before we'd expected.

One afternoon we were careless and didn't lock the bedroom door. Tomás's father opened it without knocking. He found us just as I had one hand gripping Tomás by the hair and the other around his neck, while I fucked him from behind, my cock going in and out of his ass in full view.

—Easy, boys —the man said impassively—. It's all right.

He closed the door and left us alone.

—Keep going, keep going —Tomás told me, still bent over with his ass in the air—. Don't worry about my old man; he's more open-minded than he looks.

I grabbed his hips and shoved it all the way inside him again. I finished inside him as usual, emptying myself into that tight ass that had already become an addiction. In the end, it was his mother who took things to the limit after his father told her. We had to face the music, I ended my other relationship, and we moved in together.

Today he looks like a doll: long hair, a body many women would envy, and me, delighted that that ass, that mouth, and that cock belong only to me.