When My Buddy Met the Tranny at Home

I met Valentina in high school. We were inseparable: two teenagers with far too much free time and too few answers to the questions that mattered. Over time, life separated us geographically, but not in affection. Years later she asked me to be the godfather of her eldest daughter, and I accepted without hesitation. Through that bond I also got to know Adrián, her husband: a physically imposing man, though careless in his appearance, the kind of guy you can tell from a distance is not the one calling the shots at home.

Adrián and I became friends naturally. Compadrazgo has that virtue: it creates a trust that would take years to build otherwise. At the time I was living in Guadalajara; they were in Puebla.

One Thursday I got his message: he had a work trip to Aguascalientes and needed to make a stop in my city. Could he crash at my place? I told him of course.

***

He arrived on Friday around eight at night. I saw the lights of his pickup pull up outside the gated community and went out to meet him. He had a travel bag in one hand and, in the other, a bottle of good-label whiskey. I liked that.

We settled into the living room. I put out ice and sparkling water. I also brought out some weed I’d been saving for the occasion. The first drink was taken in silence, sizing up the mood. The second came with conversation.

We talked about work, soccer, trivial things. But by the third glass the conversation turned more personal.

—How do you do it? —he asked, looking into the bottom of his glass—. You always seem to be okay.

—Maybe because I don’t come home to someone waiting for me angry —I replied.

He let out a short laugh. The kind that stings a little inside.

—I wish. Things have been bad with Valentina for a long time. A very long time.

I didn’t speak. Silence invites too, and he wanted to talk.

—We’ve gone more than three years without fucking, buddy. Not a blowjob, not a touch, not even the good-morning kisses we used to have. I don’t want to go looking for trouble outside because there are always consequences, and she controls the money, so —he shrugged— I jerk myself off alone. Literally.

—Three years?

—Three years —he confirmed—. I don’t even try anymore. I go to sleep with a hard cock and wake up the same way.

I poured another glass. There are moments when the best response isn’t a word but a gesture.

—You really do live well —he said after that, changing his tone—. Single, free, you can fuck whoever you want.

—More or less —I said.

—What do you mean, more or less?

There was a pause. I don’t know if it was the alcohol, the trust built up over years of compadrazgo, or simply that I felt like being honest that night. What came out was direct:

—I can fuck a woman or a man. Sex isn’t exactly lacking in my life.

I watched him process the information without moving. Then:

—Seriously? Men too?

—Yeah. I’d rather that stay between us, but yes.

He nodded in a way that meant both “understood” and “I need to digest this.” Then he said something I wasn’t expecting:

—Look, I’m going to trust you with something I haven’t told anyone. I’ve always been into trans girls. I don’t know how to explain it. I like women, but I can’t ignore that. I get hard just imagining it. What stops me is not knowing how it works. If the other person’s also going to want to stick their dick in me, and I don’t do that.

I breathed slowly before answering.

—There are different dynamics. Not everyone wants the same thing. There are girls who only take it. Who only want to get fucked hard.

—And you? —he asked, looking straight into my eyes.

—I’m a bottom. Always have been. I like getting fucked.

He didn’t react right away. He just watched me. I picked up the phone that was on the couch, scrolled through the gallery until I found the right photo: me, months earlier, in a black dress above the knee, dark wig, discreet makeup. An image that showed nothing scandalous, but left little doubt about who the person in the photo was.

I handed it to him without comment.

He looked at it. Brought it closer. Looked at me. Looked back at the photo.

—That’s you.

It wasn’t a question.

—That’s me —I confirmed.

—You don’t look anything alike. If I saw you on the street with no context, I’d greet you like any other chick and keep walking. —He paused—. You’re hot as hell.

I laughed. Embarrassment and pride mix in strange ways in moments like that.

—Hot as a woman? —I asked.

—As a woman —he confirmed—. The kind you turn to look at on the street.

Then there was a different kind of silence. Heavier. Under his pants, a bulge was already showing that hadn’t been there before. I took a second before proposing what I had never proposed in that way before:

—If you want to meet her in person... I could call her. It takes about thirty minutes to get here.

He watched me for a few seconds, weighing whether I was serious.

—I’d love that —he said at last.

I asked him to go downstairs to buy cigarettes to give me time. He got up without asking questions, still visibly hard in his pants.

***

I went upstairs the moment I heard the door close. Thirty minutes was optimistic; I’d have twenty if I hurried.

Luckily, I’d shaved that day. My skin was ready, not a single hair, smooth all the way to my ass.

From the closet I took what I saved for occasions like this: a black skirt halfway down the thigh, a tight blouse in the same color, red lingerie underneath —a thong that barely covered what needed covering, a padded lace bra—. I positioned the silicone inserts in the cups, put the clothes on slowly, stepped into the heels. The dark wig, well brushed and perfectly set. The makeup took the most time: foundation, soft contour, precise eyeliner, burgundy lipstick, gloss over it so the mouth would ask for what it already knew how to ask for.

When I looked in the mirror, Sofía looked back at me.

I heard the gate open just as I finished fixing my hair.

—I’m here!

I came out of the room and went down the stairs calmly, marking the weight of each heel on the steps. He was facing away, leaving the change on the table. He turned at the sound of my steps.

He froze completely.

—Excuse me —I said, in a voice different from my usual one—. My cousin had to step out for a minute. He asked me to take care of you until he gets back. I’m Sofía.

His eyes made a complete circuit while I spoke: from the heels to the legs, from the legs to the hem of the skirt, from the skirt to the breasts outlined under the blouse, and from there to the mouth. Slowly. Like someone trying to verify something they can’t quite believe.

—You’re... very hot —he said.

—Thank you, Adrián. Why don’t you sit down and we talk for a bit?

I turned off some of the lights and left only the staircase one on. It wasn’t darkness; it was just enough dimness for everything to show without anything being too much.

We settled on the couch. I sat beside him, legs crossed in a way that made the skirt ride up a few more inches. Conversation flowed naturally, as if what was happening was the most normal thing in the world. I gave him some advice about his marriage, about Valentina, about what women need even when they don’t always know how to ask for it. He listened. And at some point, while we were talking, I felt his hand settle on my thigh.

I didn’t move it away.

—You’ve got really soft skin —he said.

—I shaved this morning. Everything.

His hand moved up slowly, exploring the edge of the skirt, slipping underneath. He watched me while he did it, looking for some sign that he should stop. I gave him none. On the contrary: I spread my knees a little so he could get there faster.

His fingers found the lace of the thong. I felt him pause for a second when he noticed the bulge pressing the fabric, not very big but definitely there. Instead of pulling his hand back, he pressed slowly, testing me over the lingerie.

—Sofía —he murmured.

—Yes? —I answered, my voice a little lower.

—You’ve got something there.

—I do. Does it bother you?

—No —he said, and kept pressing—. Not at all.

He didn’t say anything else. He leaned in and kissed me.

***

He knew how to kiss. The kind that starts slowly and builds the temperature without rushing. He worked his tongue all the way in, with the hunger of years deferred, and I took it the same way, biting his bottom lip when he pulled back. I let him set the pace while I unbuttoned his shirt, button by button. He had a firm, broad chest, a little dark hair in the center. I kissed him there too, went down his sternum, ran my tongue over a nipple and felt it harden against my mouth.

—Fuck —he muttered under his breath.

I unbuckled his belt with both hands, without looking. I pulled down his pants and boxers all at once. And there it was.

Adrián’s cock wasn’t big: it was a monster. It came out so rigid it bounced once against his stomach before pointing at the ceiling. Long, thick, with veins standing out along the entire length, the head purple and swollen, already with a thick drop peeking at the tip. The thickness was what impressed most: wider than my wrist, and I don’t have a small wrist.

I knelt on the rug between his legs. I grabbed it with one hand —my fingers didn’t fully close around it— and stared at it for a moment. I ran my thumb over the head, wiped away the pre-cum, and put it in my mouth. Salty, dense.

—You’ve been carrying that around for three years —I said—. I’m going to empty it properly.

—You little fucking bitch —he whispered, and it took effort for him to breathe.

I spat on the head and lowered my mouth. The first few inches went in. The next ones got stuck: my jaw opened to the limit and there was no more room without pain. I pulled back, took a breath, spat again, and tried once more. With my hand at the base I worked it in a circle, squeezing in steady rhythms. With my mouth I sucked the head and the first five centimeters, sealing my lips, pushing my tongue under the frenulum. I heard him getting rougher and rougher in his breathing.

—That’s it, baby, just like that.

I grabbed his balls with my other hand —they were heavy, loaded, pulled tight by the arousal— and massaged them slowly while I kept sucking the head. Saliva dripped in strands down my chin, soaking his shaft, running down to his scrotum. I pulled back, smeared it on my cheeks, rubbed him with the length of my tongue, then took him in again. I slipped once and gagged; I yanked him out coughing, eyes watering and mascara running, and he almost lost control.

—Wait, wait —he said, grabbing my hair—, I’m going to cum in two minutes like this.

—Good sign —I said, my voice broken—. But not yet.

I wiped my chin with the back of my hand and stood up. I turned my back to him. I lifted my skirt slowly, very slowly, until it bunched at the waist, and showed him the red thong bitten between my ass cheeks. I moved it aside with a finger, leaving my ass exposed.

—Spit on me —I asked.

He spit on me twice. I felt the warm stream fall exactly where it needed to fall. With two fingers I spread it around the hole, made a couple of circles, pushed one finger in up to the knuckle, then two. I already knew how to open myself up.

I sat on him slowly, looking for the angle. I grabbed his cock with my hand and aimed it at the center. I lowered a few millimeters. The head pushed and wouldn’t go in: too much at once. I breathed. Lowered a little more. The crown forced its way through and I felt the pure stretch, the good burn that comes when something too big finally gives. I let out a long moan.

—Slow, slow —he said, grabbing my waist.

—Shut up —I replied—. I know how to take it.

I kept lowering myself little by little, letting my body adjust centimeter by centimeter. Every time I felt I couldn’t take any more, I rose two and dropped three, gaining ground. The head bumped deep inside me, in a place rarely touched. When I felt him fully buried, my ass resting on his thighs, I paused for a moment. I was filled to the throat.

Then I started moving.

At first softly, finding the rhythm, bracing on his knees to go up and down. The cock went in and out slick with saliva. His hands on my hips, keeping time. His lips on my neck from behind, biting me, sending shivers up my spine. I picked up speed little by little and he answered in kind, driving up to meet me halfway, delivering hard thrusts that made me bounce in his lap.

—I can’t believe this —he said softly.

—Shut up and stay like that, fuck me —I answered—. Tear my ass apart, daddy.

He did as told. He dug his fingers into my waist and started fucking me from below with a different kind of force, without mercy. You could hear thighs slapping, ass cheeks bouncing, the saliva and fluid dripping over his balls. I pinched my nipples over the blouse and kept moaning.

***

He asked me to change positions. I obeyed: I pulled his cock out, wiped it with my hand, and got on my knees on the couch, bracing myself on the backrest, arching my back, sticking out my ass, spreading my legs just enough to give him access. The skirt bunched at my waist. The thong hung from one ankle.

He got down behind me on his knees. He opened my ass cheeks with both hands and looked at me, open and throbbing. He spat again. He pressed the head against the hole and pushed. This time it went in all at once, to the hilt, without pause.

—Ah, you son of a bitch! —I shouted.

—Did that hurt?

—Harder —I asked him.

And he was harder. And deeper. And faster.

He grabbed my hair, gathered the wig in one fist and pulled back, arching me even more. He was hitting me with his thighs against my ass and the sound was obscene, wet, dry, wet, dry. I asked for harder and he gave me harder. I asked for deeper and he gave me deeper. He reached underneath, found my cock —hard, dripping— and grabbed it to jerk me off in sync with his thrusts.

—You’re soaked here too —he said.

—It’s from wanting it —I answered as best I could.

There’s something about that position, with the weight on top and the sound of bodies moving together, that simplifies everything: only pressure exists, heat, movement, a cock going into a place it should not reach. Thoughts disappear. All that’s left is that: the hole filled, the hard hand on me, skin slapping skin.

I felt the first orgasm coming. I warned him with a longer moan than the others.

—I’m cumming, I’m cumming, don’t stop.

He didn’t stop. He squeezed my cock, worked me faster, and with two deep thrusts he pulled the orgasm out of me. I came over his hand and over the couch, in several spurts, clenching his cock with my ass each time a spasm hit. He felt it and let out a grunt.

—Fuck, you squeeze so hard.

—Keep going —I said, shaking—. Don’t pull out.

After that I lay back on the couch. I grabbed a cushion and put it under my hip to lift my pelvis. He yanked the thong off my ankle and threw it to the floor. He lifted my legs and rested them on his shoulders, folding me almost in half, and went in again. From that position I could see his face: eyes shut, jaw tight, mouth slightly open, the expression of someone who has waited a long time for something and finally has it.

—How long had it been since you’d fucked? —I asked.

—Too long —he answered without opening his eyes, pounding into me.

—It shows. You’re rock hard.

He smiled despite himself. And kept going. He shoved it in all the way and stayed there for a moment, pushing extra hard, searching for an impossible centimeter. Then he came almost all the way out and drove back in with one stroke. Every time he did it, my mouth opened wider without me realizing.

I asked him to look at me, to open his eyes. He did. There’s something different about an encounter when both people are looking each other in the face: a honesty that doesn’t exist in any other position. I wrapped my hands around his hips and pulled him toward me with every thrust. The rhythm grew more urgent, more irregular. I could feel his cock swell even more inside me, thickening just before the end.

—I’m going to cum —he announced, his voice breaking.

—Inside —I told him—. I want to feel it inside.

He looked at me for a second, checking.

—Inside, motherfucker —I repeated—. Fill me with all your cum.

That was enough. He dug his hands into my thighs, buried his face in my neck, and drove into me three, four, five more times, each one slower and deeper, until he stayed inside and I felt the first contraction. It was like the cock was jumping at the bottom of me. A hot spurt, and another, and another. I counted them by instinct: six, seven thick pulses that slapped against my intestinal wall. Three years of buildup unloading in a single rush.

I felt it in every contraction: the warmth spreading inward, the pressure of his body against mine for a long moment, his broken breathing against my neck, the balls tight against my ass. I came a second time, without touching myself, just from feeling him explode inside. The cock left me in spasms and I squeezed, squeezed, milking him down to the last drop.

I stayed still, not moving, feeling every second of it. He didn’t pull out right away either. He stayed inside, breathing hard, giving me wet kisses on the shoulder and neck. When he finally withdrew, he did it slowly, and the cock came out dripping semen and saliva, still half-hard.

I barely sat up. I felt the trail of what had happened sliding along the insides of my thighs, a warm stream running down to the couch. I slipped in two fingers, pulled out a little, and took it to my mouth. Thick, salty, with that taste of a man who had been kept in storage too long.

—You’d gone a long time without that —I said.

—Too long —he confirmed. And this time he looked me in the eyes when he said it.

***

We smoked in silence. We finished the last of the drinks. The living room smelled of tobacco, whiskey, and semen. Also of something harder to name.

He went to the guest room around midnight. I stayed a little longer on the couch with the lights off, listening to the quiet house, still feeling the other man’s load slowly leaking out of me.

I thought it had been a single night. A parenthesis that would close on its own with dawn, with no awkward conversations or strange looks the next day. That’s how those things work, I figured. A moment outside time, and that’s it.

I was wrong.