I Asked Him to Be My Escort, and Ended Up Naked on His Sofa

The trial year was about to end and I had absolutely no doubt about what I wanted. Life had thrown me an unexpected card when the desire to be a woman awoke in me, but it only took a few months to understand that that was my truth, that I had been born for that. However, before closing that chapter, the doctor who was guiding me through the process referred me to a specialist.

—How have you been with your new identity? —he asked me in our first session.

I answered with all the excitement in the world. That being a woman was what I had always should have been. That I finally felt complete, free, that my life made sense for the first time. But the smile did not last long.

—I’m glad you feel that way, but you need to understand everything involved in taking the final step —he added in a cautious tone.

—I know, I know, I’m ready to keep going —I insisted, impatient—. But I have a question: what if I don’t want to give up my cock?

—Then your transition would not be complete from a clinical point of view —he replied, unmoved.

At that moment I did not know that there were trans women who kept their male anatomy. All the information they had given me was strictly medical: either you accepted the whole package or you were not really a woman. At least that was what they had made me believe.

I left that appointment with my head spinning but with my conviction intact. I researched on my own and discovered that my transition did not depend on surgery. It was true that I would not be able to conceive or menstruate, but I could keep moving forward with hormones, with my identity, with the life I wanted. That brought me peace again.

***

The news also put my parents at ease, especially my dad. Even though he already accepted me as his daughter, he worried about the future. Seeing me each day more confident, more feminine, more me, finally convinced him of something that had been brewing for months. He stopped being the distant father who barely spoke to me when I was his son and became a proud dad of his little girl. That bond sprang up out of nowhere and changed both of us.

A month before the school year ended, my parents surprised me with something I absolutely was not expecting.

—We’re going to throw you a quinceañera! —they both told me with huge smiles.

—What do you mean, a quinceañera? —was all I could manage to say.

—We know you’re already a young lady and that this is the path you chose —my mom explained—. We’ve talked about it a lot and we want to celebrate you properly. With your friends, your family, everyone.

Everyone’s going to be there, I thought, with a knot in my stomach. Many of my relatives did not know anything about my transition.

—What better way to introduce you to the world as the woman you are? —my dad added, and his smile completely disarmed me.

I have to confess that at first the idea seemed insane to me. But their enthusiasm was contagious. After all, if God already knew, let the whole world know too.

—All right, I accept —I told them—. But I want everything formalized before the party. I want to have started hormones already, no turning back. And I need you to promise me something else.

—What is it? —my dad asked, narrowing his eyes.

—That you’ll help me with the surgeries. The breasts, the laser treatment, everything I need to feel complete.

—All right, all right —he interrupted, raising his hands—. I’ll save as much as I can and we’ll see what can be done.

I hugged them both so hard I almost knocked them over. That day I felt like everything in my life was going to get better. The doubts the specialist had planted dissolved with my parents’ support. I ran to my room and dialed Santiago’s number.

I told him about the party and asked him to be my chambelán. Of course he said yes, but with one condition: that I go to his house and ask him in person. If I didn’t go, he wouldn’t do it. I smiled, biting my lip, and we made plans for the next day.

***

Like every two weeks, my parents left on a work trip. That day I didn’t have classes, so I helped them with their suitcases and as soon as they left I started getting ready. Over my lingerie I put on boys’ clothes to hide it, since Santiago’s parents did not know my reality. It was still not completely dark when I left the house.

I rang the bell and Santiago opened the door with that smile that always made me tremble a little. When I walked in, I was speechless. There were candles lit all over the living room, a bottle of red wine on the coffee table, a bouquet of flowers beside the sofa, and soft music playing from somewhere. A sweet scent hung in the air.

How beautiful, I thought, while confirming what I suspected: his parents were not home. Typical of them, and typical of Santiago to take advantage of the situation.

He led me to the big sofa, the three-seater. I sat down and before I could say anything he knelt in front of me, took my face in both hands, and kissed me. First my lips, slowly, barely brushing them. Then he went down to my neck, to the hollow between shoulder and ear, while I closed my eyes and let myself go.

I should have put something better on, I thought fleetingly. I would have loved for him to see me in the new lingerie instead of this sweatshirt. But Santiago did not seem to care what I was wearing, only what was underneath.

He increased the intensity of his kisses and his hands began roaming me hungrily. First my shoulders, then down to my breasts over the fabric, squeezing them, searching for the shape of my nipples beneath the bra. I felt them harden at the first touch, felt my own cock begin to tense inside the lace underwear I had hidden underneath. When you are a teenager those moments feel eternal, even though in reality they were only a few minutes. But I lived them as if time had stopped just for us.

He pulled my sweatshirt up and over my head. Then he unclasped my bra with fingers that trembled a little, which I found tender, and laid me back on the sofa. He stayed looking at me for a moment, as if wanting to memorize the sight, and then bent down to kiss my breasts. First gently. Then hungrier, his tongue circling my nipples, sucking them until a sharp moan escaped me that I had no idea came from where. I arched toward him, enjoying every caress, every brush of his lips, feeling my skin rise in gooseflesh under his mouth and, lower down, my cock pressing against the lace asking for air.

He ran a hand over my stomach and down to the edge of my jeans. Without stopping kissing my nipple, he unbuttoned my pants and pulled them down just enough to expose the black lace fabric of my panties. He stopped. He lifted his head and looked at me.

—You’re gorgeous like this —he murmured, and ran his fingers over the fabric, feeling how my cock stood out hard beneath it—. All mine.

—All yours —I answered in a broken voice.

Suddenly he stopped. He made me sit up, gave me a soft kiss on the forehead, and whispered in my ear:

—Close your eyes. I bought you white chocolate, the kind you love.

I obeyed with a smile. I felt something brush my lips. Something warm, slightly damp, that did not have the texture of a wrapped sweet. When I moved my hands to take it, what I found was Santiago’s bare skin. He had stripped completely while my eyes were closed, and his cock, hard and covered in melted white chocolate, was right in front of my mouth.

A wave of heat swept through my whole body. I opened my eyes and looked at it for a second: thick, with the vein marked and pulsing on one side, the tip swollen and glossy with chocolate. I gave it an initial lick from base to tip, collecting the sweetness, and he let out a moan that vibrated through my fingers.

—Slowly, you’re hurting me —he murmured through clenched teeth—. Taste it like it’s your favorite fruit.

I did as he said. I worked my way over it centimeter by centimeter with my lips, licking off the chocolate until no trace of sweetness remained. I ran my tongue over his balls, one and then the other, taking them into my mouth one at a time while he gripped the back of the sofa and panted. I went back up the shaft, slowly, pressing my lips against the hot skin, and when I reached the tip I took the whole thing into my mouth.

But I did not stop. I worked it in and out with a rhythm I discovered purely by instinct, playing with my tongue on the tip, circling the glans, taking him deep until I felt the head bumping against the back of my throat. Every time I pulled him out I left a strand of saliva that fell over my bare breasts. At one point he became too big for me and I could not take him all the way, so I held him with both hands and made up with my fists what my mouth could not reach, moving them up and down while I sucked the tip like my life depended on it.

—That’s it, princess, that’s it —he panted, looking down at me—. Suck me, my love, what a lovely mouth you have.

Hearing him talk dirty to me turned me on even more. I caressed his stomach, his thighs, his tight balls. I ran my tongue underneath, from the base toward the back, and he shuddered all over. I grabbed his hips and pulled him closer to me to speed up the rhythm, letting him push, letting him fuck my mouth however he wanted. Santiago started breathing in broken gasps, tensing, grabbing my hair with both hands in a urgency that only lit me up more. Every thrust hit me deep and my eyes filled with tears, but I did not want him to stop. I could feel my bare breasts moving in time with every motion, my own hard cock pushing against the damp lace, a little puddle of pre-cum staining my panties. Excitement ran through my whole body: hard nipples, a deep heat in my lower belly, every nerve awake and throbbing.

—I’m going to come —he growled through clenched teeth—. Swallow it all, my life, don’t leave a single drop.

I dug my nails into his ass and shoved him toward me. When he could take no more, he came in my mouth with a long, rough moan that rose from the depths of his chest. The first spurt hit my palate, hot and thick, and another came after it and another. I swallowed everything without thinking, gulp after gulp, feeling the semen slide warm down my throat while he braced himself on my shoulders so he wouldn’t collapse. Still with his cock in my mouth, I kept sucking him slowly, milking the last drops until I left him clean. His body trembled and mine trembled with him. I was left with that salty, warm taste on my tongue, still mixed with the memory of chocolate.

He laid me back on the sofa and lay down beside me, wrapping an arm around my waist. His warm body against my back, his breathing still ragged against my neck. He reached a hand forward and slid it inside my lace panties, finding my hard, wet cock. He squeezed it without saying anything, tenderly, with an open palm, and started moving it slowly.

—Now it’s your turn too, my love —he whispered, kissing me behind the ear.

I closed my eyes and pressed myself against him. His fist moved me up and down with a slowness that was driving me crazy, squeezing just below the glans, using my own slick to glide better. I moved my hips against his hand, pushing, seeking more friction, biting my lip so I wouldn’t scream. With his other hand he took one breast and pinched my nipple, and that was enough. I came into his fist with a long moan, feeling the hot release stain my stomach, the lace, his fingers. He kept squeezing me gently until the last shudder, drawing out the very last drop, and then he brought his stained fingers to his mouth and sucked them clean.

—Thank you for my gift, love —he whispered, kissing me behind the ear—. I loved it.

I turned my head and we gave each other a long, slow kiss, tasting of chocolate and everything else, the flavor of both of us mixed together on the tongue.

—I’m glad you liked it, baby —I told him, smiling—. And thank you for the surprise.

Within minutes his breathing became deep and steady. He had fallen asleep. I got up carefully, wiped my stomach with a napkin, and took off my stained jeans. I stayed in my lace underwear, still damp. I went to his room, found a clean sheet, and covered him. Then I put my sweatshirt on with nothing underneath, slipped on my sneakers, and waited for my dad’s call.

When the phone rang, Santiago was still sound asleep.

—How did it go, daughter? —my dad asked.

—Very well —I answered, holding back my laugh—. Santiago agreed to be my chambelán.

—That’s great, I’m glad. Take good care of yourself, see you later.

I kissed Santiago on the forehead, though he did not even stir, and slipped out, closing the door without making a sound.

***

I walked back home with my body still burning. The afternoon with Santiago had left me with a heat that would not go out, with the taste of his cum still in my mouth and the cunt of my panties sticky with mine. The idea of having the house to myself all night already had me imagining things. On the way I detoured a little and passed in front of the market warehouses. The metal gate was rolled shut and the windows were dark. Everything seemed closed.

It was around six-thirty in the evening when a deep voice startled me.

—Looking for someone, brown girl?

I stepped back on instinct. A man was peering out through one of the windows I had thought were offices. It turned out to be the night watchman’s room who guarded the warehouses.

—No, I was just being nosy —I answered, taking a step back.

—Want to come in and take a look? I’m alone. The workers don’t come back until Monday.

With more curiosity than caution, I agreed. He opened a gap in the gate and let me in. He explained that he only had keys to his room and to the warehouses, that the owner’s offices were locked, and that the employees had been off since Thursday because of a delay with the merchandise that was coming by train.

He showed me one of the warehouses, huge and empty, smelling of cardboard and damp, and then took me to his room, where he offered me a hot coffee. I accepted and sat in the only available chair while he settled on the edge of his bed.

I studied him carefully while we chatted about unimportant things. He had to be in his forties. Fair skin reddened by the sun, sturdy build, about six feet tall. Huge hands with thick, calloused fingers from carrying loads. A thick mustache and a several-days-old beard. Beer belly, worn plaid shirt, jeans, and work boots. He was not handsome in the classic sense, but he had something. A presence. A way of looking at me that made me feel he saw more than I wanted to show. As if he knew what I had under the sweatshirt and what I had done an hour earlier.

Before I knew it, it was eight at night.

—Excuse me, I have to go —I said, standing up abruptly.

—Whenever you want to come back, I’ll be here —he replied, walking me to the gate with a smile I could not quite decipher.

I walked the last blocks with my hands in the pockets of my sweatshirt and a smile I also could not quite explain. It had been a very long afternoon. The promise of my quinceañera, Santiago’s hands on my skin, his release sliding down my throat, the sweet taste I still felt on my lips, and now this stranger waiting for me to come back. I entered the empty house, locked the door, leaned back against it, and thought: Tomorrow is going to be a very interesting day.