My Boss Dared Me to Dress Like a Woman, and I Agreed

What I’m going to tell happened to me for real, when I was twenty-eight and had just finished my accounting degree. I started working at a medium-sized company in the accounting department, and my boss was named Damián. He was a married man of forty, and over time we formed a friendship that went beyond work. At every office gathering he kept an eye on me, especially when we went out for drinks with the other coworkers. He looked after me as if I were his little brother.

We became so close that we told each other things you don’t talk about at work. We talked about the kind of women we liked, our relationships, everything. I was going out with Carla, a girl from another department, and we were serious. He, on the other hand, confessed to me one day, asking for absolute discretion, that he had a lover in the very same office and that no one suspected a thing.

—This stays between us —he said in a low voice—. Not a word.

—It’s buried with me —I answered.

A year later, the company opened a branch in a city forty-five minutes from where we lived, and the two of us were transferred there. From then on we traveled together almost every day. I was still with Carla, and he had ended that extramarital relationship. The new team was small: Damián in management, me as accountant, four assistants, and an unmarried secretary named Lorena.

Lorena was a striking woman, and Damián had a magnetism that was hard to explain. He was just over five foot seven, with brown skin, a manly, hairy body, bright eyes, and a deep voice that commanded respect. I admired him: orderly, hardworking, impeccable, always wearing a perfume that lingered in the air after he passed. Two months later he had already become Lorena’s lover, and once again I was the only one who knew.

Then came weeks of brutal work. We stayed late closing balances, and sometimes it got so late that we decided not to drive back and stayed at a nearby hotel. I was a guy with an ordinary look: thin, short, hairless, with a certain fragile appearance. People always told me I looked like my mother, who is a very attractive woman. But inside I felt like a man in love with Carla.

One of those nights when we were working alone in the office, I went to the filing cabinet to look for a folder. Damián came up behind me without my hearing him, grabbed my waist, and pressed himself against me. I felt his hard body against my back, and I also felt, very clearly, the bulge of his cock pressing against my ass over his pants. I tried to pull away, but his strength wouldn’t let me.

—I’m too attracted to you —he whispered in my ear—. You have no idea how hard I get thinking about you.

—You’re crazy —I said, and jerked away.

We kept working as if nothing had happened. I took it as a tasteless joke, one more. When we went out to eat, as we walked down the street, he put his arm around my shoulders as he had so many times before. To me it was normal; he had done it a hundred times already, as friends.

—Look —he told me that night, more serious—. When I met you I saw someone polite, noble, honest. That’s why I decided to keep an eye on you, because the others are something else. But I’m going to confess something: if you were a woman, I would’ve fucked you until you couldn’t make a sound. You’ve got an ass that gets noticed every time you bend over.

I let out a nervous laugh to brush him off.

—One day I’ll dress like a girl and you’ll see I’ll look terrible, because I’m a man.

—I dare you —he replied at once—. Go ahead and you’ll see I’m right. With your face and your body you’d look like a girl. You look like your mother, and not everyone can say that.

It was absurd. And yet I couldn’t stop thinking about it.

—I’ve never been with someone trans —he went on—, but with you I feel something I’d never felt before. If you end up as beautiful as I think, would you dare let me put my cock in you and make you feel what a woman feels when she’s fucked right?

—Maybe —I told him, stalling, convinced I would never do it—. If I decide to, I’ll let you know.

That night, in the hotel, we started undressing to get into our separate beds. Seeing his strong, hairy body, so different from mine, he said:

—Your skin looks delicate. You’ve got the body of a little woman.

I didn’t answer, so as not to keep the topic going. I changed the conversation to our experiences, and he told me in vivid detail what he enjoyed most before being with a woman: how he liked to spread Lorena’s legs and eat her pussy until she screamed, how he put her on all fours and shoved it in her all the way, how he loved cumming in her mouth. Sleep got the better of us. In the morning the alarm went off, he jumped out of bed, and when he took off his boxer briefs, I caught a side glance at what he was packing: a thick, long cock with visible veins, hanging between his legs even at rest. I felt small, and I made sure he saw nothing of me out of sheer embarrassment. We got ourselves together and everything went on as always.

***

What I didn’t expect was what would happen to me. When Damián didn’t drive back with me because he stayed with Lorena, I started to feel something like jealousy. It took me a while to admit it, but I was falling in love with him. And his persistence never stopped: every so often he’d ask me, with that half-smile of his, when I was going to dress like a woman. The idea, which at first seemed insane to me, started taking root inside me.

One day I told him I’d give him the date soon. I saw his eyes light up.

—Just tell me when —he said—. And from now on I’m not going to call you by your name. I’m going to call you my queen, my Liana.

Those words lit a fire inside me like embers. I prepared myself calmly. I bought everything I needed online and spent weeks learning how to do my makeup, how to move, how to look at things differently. For three months I caressed and stimulated my chest every day, around the nipples, again and again, until I noticed a real change. I started wearing a bra. When I was ready, I gave him the day. We would stay at the usual hotel.

That afternoon I packed my bag and went ahead. I took a long bath, I had shaved every inch of my body in advance —legs, pubic area, ass—, and little by little I transformed myself in front of the mirror. The makeup, the perfume, the shoulder-length wig. I chose a red set with thin straps, a garter belt, skin-tone stockings that made my legs look longer, matching heels. Over it all I put on a black blazer with very faint white stripes, fitted to my size, covering everything else. All it took was unbuttoning it to reveal what I had become.

When I looked at myself one last time, I hardly recognized myself. The one looking back from the mirror was a woman, and she was shaking with nerves.

There were ten minutes left until the agreed time. Every second felt endless. At last I heard knocks on the door and my heart shot up into my throat. I opened it. Damián went silent, staring me up and down as if he couldn’t process what he was seeing.

—No way —he murmured.

He locked the door and came at me, searching for my mouth. I didn’t resist. I returned the kiss, deep, long, while his hands roamed over me through the blazer, squeezing my waist, my ass, sliding up over the padded fake tits of the bra. I felt his tongue enter my mouth hungrily, and I sucked on it as if it were the only thing I had ever waited for in my life.

—From tonight on you’re going to be my woman —he told me against my lips—. My queen Liana. I’m going to fuck you until you don’t even remember your man’s name.

—Yes —I answered without thinking—. Make me yours. Put it in me.

He unbuttoned my blazer slowly, button by button. When I was revealed, in that red set with the garter belt and stockings, I saw in his face a mix of amazement and desire that took me to a level of excitement I had never felt before. He took my hand, turned me around, and hugged me from behind, pressing himself to me. I felt his cock already hard, marking itself between the cheeks of my ass, barely separated by the fabric of his pants and my lace thong. He kissed my neck while one hand went up to my chest and the other down to the garter belt, caressing the inside of my thigh, higher and higher, until it brushed between my legs and felt my own erection trapped beneath the thong.

—Look at you —he whispered, squeezing me over the fabric—. My queen has her own little thing too, and I don’t mind. Tonight I’m going to use all of you.

He turned me toward him again and lowered his mouth to my chest. He sucked my nipples through the bra, biting them softly, then pulled the straps down and licked them directly, one and then the other, playing with the tip of his tongue until they stood hard as stones. I wanted him with a urgency I didn’t recognize, and I felt wet between my ass cheeks just imagining what was coming. I knelt on the carpet, opened his pants, pulled down the zipper, and let them fall along with his boxers. His cock sprang up in front of my face, hard, thick, the tip already shining with a heavy drop. I stroked it with my hands first, slowly, just closing my fingers around the hot shaft. It was much bigger than I had managed to see that morning in the hotel.

—Suck me —he said in a hoarse voice, grabbing my wig—. I want to see my queen sucking me off.

I opened my mouth and took it in. First the tip, tasting that salty fluid, then slowly going down the shaft, as far as it would fit. With my tongue I traced the underside of it, the thick vein throbbing there, while with my hand I fondled his balls. He guided me by the nape, setting a slow rhythm, letting me swallow it until I choked on it. I sucked his balls one by one, licked the shaft from top to bottom, went back up to the tip and took it deep again. I heard him moan, and that turned me on even more. Every sound he made confirmed that the challenge had become something else. My mouth was full, my jaw tight, and my own cock was dripping inside the thong.

—You’re incredible —he said, his voice broken—. I had no idea you sucked like that, my queen. You’re going to make me cum too soon.

He yanked his cock out of my mouth, with a thread of saliva hanging from my lip. He lifted me off the floor and carried me to the bed, as if I weighed half of what I do. He stripped completely, took off my blazer and bra, left me the garter belt, stockings, and heels, and only slid my thong aside. He settled on top of me and spread my legs with his own. Feeling his hairy chest against my shaved skin, and his hard cock resting on my stomach, I lost my mind. I begged him not to wait any longer.

He went first down my neck, licked my nipples again, then kept going down my belly. He took my cock in his hand and stroked it slowly, and even brought it to his mouth for a moment, sucking it calmly, while I arched on the bed unable to believe what was happening. Then he lifted my legs, rested them on his shoulders, and lowered his mouth to my ass. I felt his hot tongue licking between my cheeks, going in and out of the hole, coating it with spit, opening me slowly. I moaned, gripping the sheets, with the stockings tightening over my thighs.

—What a nice ass, my queen —he murmured between licks—. I’m going to leave it open for me.

He pulled a little bottle of lubricant from his pants, one he had brought prepared. He coated me well, slid one finger in first, then two, moving them in circles, stretching me open. It tickled and felt good at the same time, and I pushed my hips against his hand, asking for more without saying it. When he positioned me face down and put me on all fours, ass raised and face against the pillow, I felt the tip of his cock resting right at my entrance.

—Slowly —I begged—. Please, slowly.

—Easy, my queen —he answered, grabbing my hips—. You’re going to love it.

There was pain at first, sharp, making me grip the sheets and bite the pillow when the thick head forced its way inside me. He stayed still for a moment, buried only halfway in, letting me get used to it. Then he pushed more, entered a little further, and so, little by little, I felt him slide all the way in, until his balls struck my ass and his pubic hair scraped my cheeks. The pain began to turn into something else, a hot current running through my whole body from my asshole to the tip of my own cock, which was twitching hard between my legs without anyone touching it.

He started moving. Long pulls out and deep thrusts in, keeping a slow rhythm that made me moan every time he reached the bottom. I held onto the pillows while he fucked me from his knees, gripping my hips, driving his cock into me to the root again and again. I moaned without recognizing my own voice, with a high voice I didn’t know I had, surrendering in a way I had never imagined.

—That’s it, my queen —he panted behind me—. Look at you swallowing my cock. This ass is mine now.

—Yes —I answered between moans—, it’s yours, all yours, don’t stop, put it all in.

He sped up. Now the thrusts were harder, drier, the slap of his hips against my ass echoing through the whole room. He yanked my wig back and forced my spine to arch, which drove his cock even deeper, hitting a spot inside me that made me see flashes. I felt my own dick throbbing on its own, trapped between my stomach and the sheet, soaking the fabric with thick streaks of fluid without even having come yet.

He turned me over again, laid me on my back with my legs once more over his shoulders, and went back to putting it in while looking me in the eyes. Now I could see his face, red, sweaty, jaw clenched, and he could see my fake breasts bouncing with each thrust, the messed-up wig, the painted lips open and moaning for him. He kissed me on the mouth without stopping fucking me, and I wrapped my legs around him, closing the garter belt over his back, asking for more.

Time disappeared. I don’t know how long it lasted, I only remember that at some point his hand went down to my cock and started jerking me off to the same rhythm he was driving into me, and that was the end for me: I came in spurts between our two bellies, long, hot, while my ass clenched on its own around his cock as if it didn’t want to let it out. That spasm drove him wild. He gave three or four more brutal thrusts, burying himself to the hilt, and I felt his heat spill inside me, stream after stream, while he moaned my new name against my neck. A shiver ran through me from head to toe. It was an orgasm unlike anything I had ever known, something born from a new place, deeper inside. That night I enjoyed myself like never before, and for the first time I understood what he meant when he talked about feeling like a woman.

He stayed inside me for a long while, until his cock softened on its own and slipped out with a wet pop. I felt a warm thread of his semen trickle between my ass cheeks down to the sheet. We lay there, my body half over his chest, one of my legs between his, still wearing the stockings. He kissed my forehead.

—You were amazing —he said—. I want you to be my lover, my confidant, my woman. Leave Carla. I’ll leave Lorena for you. No one has to find out about us.

I stayed silent for a moment, still breathing hard and with my ass throbbing. Part of me wanted to say yes. But I thought of Carla, of the life I had outside that room.

—No —I said at last, my voice rough—. I want to keep being who I am. This was a test, a beautiful experience I’ll never forget, but I can’t.

He kissed me with a calm that hurt more than any complaint.

—I liked too much the way you gave yourself to me —he whispered in my ear—. How you suck, how you let yourself get fucked, how you come when I put it in you. Think about it for a month. If you say yes, I’m going to make you happy, my queen Liana.

—I’ll think about it —I lied, because I already knew my answer—. But I think you know it.

That dawn, while he slept with one arm across my waist and dried semen sticking to my skin, I lay there staring at the hotel ceiling, still not knowing what to do with everything I had just discovered about myself. What I decided afterward, and how that story really ended, is something I’d rather save for another time.