My Boss Dressed Me as a Woman and Claimed Me as His Own

I had been friends with my boss at work for quite some time, to the point that we went out together on Fridays to have a few beers and chat about anything. Even so, I had never set foot in his house. Don Aurelio was nothing spectacular as men go, but he was pleasant enough: about five foot seven, fifty-eight years old, gray-haired, thin, with delicate hands. I was twenty-five and had been working for him for three years, three years during which that friendship had grown even though I never mentioned my travesti inclinations.

One afternoon he invited me over to his place. We were drinking some rum and cola and chatting when he got up to use the bathroom. He left his phone on the sofa where we were sitting and, while he was coming back, I heard it vibrate. Some message, a social media notification, whatever, I thought, and almost by reflex I picked up the device to look, with no real curiosity.

That changed in an instant. On WhatsApp, a travesti girl had sent him photos. In them you could see a pair of ass cheeks taking a thick cock sheathed in a condom. I imagined the ass belonged to her and the cock to my boss, because the message said: “look how good you look in this one, baby. We’ve got to take new photos, right?” I was so absorbed in the pictures that I didn’t realize when he came out of the bathroom. He caught me red-handed, and all I could do was confess that I was looking at the photos that had just come in.

Embarrassment flooded his face. He probably didn’t want me to know he liked fucking travestis. I told him it was fine, that I got turned on by that scene too, and he relaxed. But his calm didn’t last long, because curiosity took over right away and he started asking me about my experiences.

I confessed I didn’t have much to tell, though the one I liked most had been a trans girl who had fucked me. He asked if I had ever been fucked while dressed as a woman, and I told him no. A few minutes passed while we poured ourselves another round and commented on what was on TV, until he asked me point blank if I’d like to dress like a girl.

—Yeah, I’ve thought about it several times —I said—, but I never tried it.

I was only half lying: of course I had, I just felt embarrassed to admit it. He smiled and suggested I dress up right then and there. Half incredulous at the proposal, I asked him if he had clothes there. As answer, he took me to his room and opened a small closet crammed with women’s outfits.

***

I liked a short cocktail dress, wine-colored, with a flared skirt and a kind of cincher that made me imagine wide hips even though I didn’t have them. My boss also kept lingerie. From his collection I chose a black thong, a padded corset, and fishnet stockings.

When I finished dressing and stood in front of him, he stared at my legs with a lewd smile. He asked if I knew how to do makeup and I told him the truth: no. So he sat me at his vanity and started doing my makeup himself, while jokingly asking me:

—Do you like it like this, or do you want to look sluttier?

I was sitting in front of the mirror and he moved back and forth around the vanity, picking things up and setting them down. I noticed the bulge under his thin dress trousers starting to rise. I could no longer stand how badly I wanted to cover that cock with kisses and suck it, and I was surprised by how hard it looked despite his age.

He picked out a wig for me and kissed me when he put it on. That first kiss was so strange. I had never thought of him with desire, but that didn’t stop me wanting a second. As we kept kissing, I got hotter and hotter, and I began to hold him tight so I could feel, through the folds of the dress, that delicious bulge that had me dazzled. He grabbed my ass over the fabric, until he could stand it no longer and lifted my dress to squeeze it roughly. When he felt my ass barely covered by the thong, he broke off the kiss abruptly, groaned, and whispered in my ear:

—Oh, little whore, you came ready to turn me on. I’m starting to think you already knew what kind of sluts I like, and you were just waiting for the right moment to offer yourself, right?

Of course I had no idea he liked travestis, but seeing him so horny, I played along.

—Yeah, the truth is I’ve liked you from the start —I told him—. Since I met you I’ve wanted to be your whore, to have you enjoy my little ass any way you please. I want you to make me your little bitch, daddy.

***

We went back to those tasty kisses, but a few seconds later he took me by the shoulders and pushed me down.

—Suck it —he ordered.

I bent down, unbuckled his belt, unbuttoned his pants, and as I lowered the zipper I watched that cock, which had been hard for long minutes of arousal, finally rise to its full length. I pulled back the foreskin, freed the head, and started stroking it slowly, really more like caressing the whole shaft, from tip to feeling his balls in my palm. When I sped up, I noticed my hand was having trouble sliding; I figured it was because of his age, because his skin was a bit dry.

I licked my palm flirtatiously in front of him, to excite him more, and went back to stroking him. It was easier, but my hand dried out almost immediately, so I ended up sucking him. The truth is I had wanted to do it since he was doing my makeup, only despite how horny we were, I still felt self-conscious. After sucking his cock like a lollipop, he said to me:

—Come here.

He gave me his hand to help me up and led me toward his bed. We didn’t make it there. Before I could climb onto it, he yanked me by the waist and left me standing in front of a dresser against one side.

He started fondling my ass, squeezing it, biting it; then he kissed it, ran his tongue between my cheeks. I was enjoying all that attention when I felt him trying to untie the cincher to lift my dress.

—No —I told him.

I had just caught a side glance of myself in the vanity mirror: with my ass lifted, the makeup making me look like an eighteen-year-old girl, manhandled by that gray-haired, lustful old man. The image was such a turn-on that I wanted him to take me like that, with my clothes on.

***

—You filthy horny little slut, you like seeing how I fuck you, babe?

He tore my stockings a little to make way for his cock and moved the thong string aside. Carefully he started wetting my asshole, spitting on his fingers until it was ready to receive that delight. Watching him pump into me reflected in the mirror got me so hot, and I started moaning softly. From how good it felt, a thin voice escaped me: “yeah… good, daddy… good, daddy,” while he made growling sounds.

I saw his face change as he drove into me harder. He looked more and more focused and raised his voice:

—That’s it, little whore, give me your ass. Enjoy the cock, you cheap little bitch.

We spent a good while fucking at that delicious pace. When he was close to coming, he slid his hands from my waist to my chest, gripped the padding in the corset, and pressed his face to my back, never stopping splitting my ass open with increasingly powerful thrusts. He came in a brutal spasm that filled my insides with cum. Between the gasps of orgasm, still with his mouth against my back, he whispered:

—You’re going to give me this at work whenever I feel like it. Remember I’m your boss.

That scared me a little, but I was also too turned on, so I only answered:

—Whenever you want, boss. Whenever you want ass, I’m here.

That night I stayed over with him. We did it one more time before collapsing, and the next morning I woke up wanting to suck him off again. It was the weekend; we wouldn’t see each other until Monday.

***

I enjoyed remembering that experience so much that, when we went back to work, I didn’t think about the implications that night of passion would bring. Monday passed completely normally. My boss and I joked as usual, as if he hadn’t given me that incredible fucking a couple of nights earlier.

However, when there was half an hour left before quitting time, he came over to my desk very seriously, carrying a folder.

—I need you to review these documents. They’re not urgent, but take a look before you leave and bring them back to me before you go.

In my role as employee, I told him there was no problem and took the folder. I finished other tasks before checking its contents, but when I finally opened it, I got a fright: inside there was a note with a set of keys attached and… the very same thong he had fucked me in at his house! The note said: “One key is for the office, the other for the locker inside. Wait for me there and dress up nice.”

At closing time I waited until everyone had left before going into the boss’s office. I opened the locker and found several dresses, stockings, a couple of wigs, and makeup. What he had told me when he came was true: I was now my boss’s whore, and he would do whatever he wanted with me.