The Transvestite They Hired for the Board Meeting

Since that afternoon when I ended up between the club director and one of his partners, I couldn’t think about anything other than the private meeting those men held every month. I had lived through it only once, almost by accident, and my cunt still burned when I remembered it. I knew they were getting together again on Thursday, and part of me hoped they’d remember my name.

On Wednesday, while I was having coffee at the bar in the place where I worked, a message from Sebastián, the director, came through: “Come to my office.” A shiver ran down my back, that uncomfortable mix of nerves and excitement I already knew well. I left my cup half-finished and went upstairs.

I found him sitting behind his desk, with that calm of his that always made my legs weak. I closed the door. He pointed to the chair across from him without getting up.

—Renata, I called you because I want to propose something to you —he said, clasping his hands on the table—. Tomorrow we have the monthly partners’ meeting. After the boring part, when most of them leave, those of us who remain lock ourselves in the private lounge. We always hire company for those nights. This time I want you to be the company.

—Me? —I swallowed—. You mean… for all of them?

—For all of them. And you won’t be the only one, there’ll be more girls. I’ll pay you the same as I pay the ones I always bring in, and I guarantee it’s generous. What do you say?

The offer caught me off guard. It was risky, it was insane, and yet the idea of being surrounded by mature men, older than me, willing to pay for my body, lit me up in a way I couldn’t explain. I felt my panties get wet right there, sitting in front of him, imagining myself on my knees sucking cock one after another. I turned it over for a few endless seconds. Then I reached my hand out across the desk.

—I’ll do it. But I want the payment upfront.

Sebastián shook my hand with a crooked smile.

—I knew you’d say yes. Tomorrow, when your shift ends, come straight over. My assistant will be waiting for you to get you ready.

I left the office with my heart pounding against my chest. As I passed Camila’s desk, his assistant looked me over from head to toe with a gaze that already knew everything.

***

I spent the rest of the day convincing myself I was making the biggest mistake of my life. But every time common sense started to win, the image of those suited men looking at me came back, and the horniness steamrolled right over reason without effort. That night I masturbated three times before I could fall asleep, with two fingers shoved deep inside me and the other arm over my mouth so I wouldn’t scream. I imagined myself knotted between eight cocks, my face sticky with cum, my ass stretched open, and I came within minutes, soaking the sheet.

On Thursday, as soon as my shift ended, I slipped up to the office floor where Camila was already waiting, seated with her legs crossed and a canvas bag on the desk.

—You got here early. You’re anxious, it shows —she said, amused—. Good, that gives us time. Take off your street clothes and put one of these on while we wait.

I opened the bag. Inside there were several lingerie sets, all in my size, as if someone had studied my body in advance. While I was going through the garments, I caught out of the corner of my eye that Camila was undressing too and slipping into a black set that made her look like a magazine maid.

—Put on whichever one you want, it doesn’t matter —she said—. You’ll have to change more than once before the night is over anyway. And let me prep you properly. If you go in there not ready, you’ll regret it, trust me.

I chose a red lace set that barely covered my tits and left my ass almost bare. Camila had me lean over the desk, legs apart and ass lifted. I felt her cold hands pulling my cheeks apart and then the warm stream of lubricant falling between them, sliding down to my cunt.

—Hold still, Renata. This is for your own good.

One of her fingers went into my ass slowly, up to the knuckle, and tore a moan out of me I couldn’t quite hide. She laughed under her breath and added a second, then a third, twisting them, patiently opening me up. She held me by the waist with her other hand so I wouldn’t get away. I gritted my teeth against the edge of the desk while I felt my cunt start leaking on its own, without anyone even touching it, soaking my thighs.

—Look at you, you’re already drenched and nothing’s even started yet —she murmured—. You’re going to be the perfect toy tonight.

When she finished loosening me, she slid a thick black plug inside me, with a wide base. She slammed it all the way in and ended the session with a sharp slap on my ass that left a red print on my skin.

—Ready —she said—. Now we wait. And don’t touch yourself, or you won’t get to come until they make you.

***

We stayed seated in silence for almost an hour until her phone rang. Camila answered, nodded, and stood up.

—It’s time. Follow me.

I walked behind her through the building’s empty hallways, my heels echoing in the silence and the red lace rubbing my hard nipples with every step. The plug weighed inside me, reminding me where the night was going to end. It was such a strange sensation, crossing those dim corridors dressed like that. When we reached the double doors of the lounge, Camila pushed them open and made me go in.

Inside were Sebastián and seven other men, all in their fifties, all in suits, spread between leather armchairs and a long table with glasses. I thought they were all there until, behind us, two more women came in. One of them was Bárbara, a club partner I knew by sight. She recognized me, gave me the slightest smile, and kept walking.

—I brought you the first one —Camila announced, gently pushing me toward the center—. The others are still arriving. You can start with this one.

She left me standing in front of all of them. I didn’t know what to do with my hands or my eyes, but my doubts evaporated when three of them stood up and started running their palms over me, sizing me up as if they had every right to. One squeezed my tits through the lace, another shoved his hand between my legs and ran two fingers through my cunt, knuckle-deep, without ceremony. He pulled them out shiny and took them to his mouth.

—She’s soaking —he said, sucking on his fingers—. She came in horny.

—So this is the one you told us about —another one said, running his thumb over my lip—. You sure she can handle it? You know how we get.

—Of course she can handle it —Sebastián answered from his armchair—. Eduardo and I already tested her together and she walked out. Test her yourself if you don’t believe me.

It was like a starting signal. The one holding the back of my neck unzipped his pants, pulled out a thick, red, throbbing cock, and shoved my head down. He filled my mouth in one go, all the way to the throat, setting a hard rhythm from the very first second. I choked, my eyes filled with tears, and a strand of saliva ran down my chin and fell between my tits.

—That’s it, slut, take it all —he growled, grabbing my hair with both hands—. Open that throat wide.

The other two took care of the back. They yanked my thong off in one pull, left the lace hanging from one leg, and, with no preamble at all, pulled the plug out with a rough jerk. The pop echoed through the whole lounge and I felt the cool air rush into my opened ass. Right away one of them pressed his swollen glans to my hole and started entering me, slow but firm, working his way in centimeter by centimeter until he buried himself to the balls.

—What a delicious ass, Jesus Christ —he panted, gripping my waist—. It squeezes like a virgin’s.

The other bent down, ran his tongue over my cunt from bottom to top, sucked my clit until my knees were trembling, and then stood up and rammed his cock into me from the front, all the way in. Three cocks at once, one in each hole, and me rocking between the three of them like a doll, moaning with my mouth full, choking on pleasure and saliva.

While they used me, I looked for Sebastián. He was seated right across from me, with his cock out but not touching anyone, watching, slowly jerking off with his eyes locked on me. Behind him, Bárbara had her legs open and Camila, on her knees, was eating her out with delicious dedication, her lips shining as she sucked at her cunt with a wet sound that reached me. And even so, Bárbara was looking at me, biting her lip, holding Camila’s head down to drive her deeper.

—What a treat this bitch is —said the man fucking me from behind, pulling almost all the way out and slamming it back in to the hilt, tearing a cry from me—. Looks like you’ve got her well trained, Sebastián. I want the ass too, come on.

—I took her ass first —the other answered, thrusting into me from the front—. And she only has one hole. You’ll have to wait your turn.

—Why don’t you both take her at the same time? —Sebastián said in a calm voice, never stopping stroking his cock—. That way someone else can use her mouth.

The two men looked at each other and smiled, obedient, and pulled me out of position. I was dizzy, on fire, my head spinning, my face sticky with spit, both holes throbbing empty. When I saw the first one lie down on the floor with his stiff cock pointed at the ceiling, I lowered myself onto him astride and sank his cock into my ass in one motion, sitting down to the balls. I screamed with pleasure when I felt it all the way inside.

—That’s it, ride it —he whispered, grabbing my tits and tugging at my nipples—. Ride that ass for me.

But before I could move, the second one grabbed my hips from behind, shoved my torso against the other man’s chest, and settled himself between my spread thighs, his cock pressing against the entrance of my cunt, already occupied by nothing, still wet and dripping.

—W-wait, no, I’ve never had two at the same time, you’re going to split me —I managed to say, trembling.

The man behind me stopped for a moment, poured more lubricant over both of us, and pushed again, until the two tips forced their way in at the same time, one in my ass and one in my cunt, separated only by a thin wall of flesh I felt give way all at once. I let out a long scream that bounced off the lounge.

—Don’t say you won’t, slut —he laughed, driving it into me to the hilt—. Look how tight you are. It’s going to hurt, but I’m going to love it. Come on, slow.

They started moving both at once, gaining ground little by little until I had them both fully inside me, two whole cocks filling me, rubbing against each other through the wall that separated them. They stayed still for a moment, savoring me. Then one began to pump while the other stayed buried, and seconds later they switched roles, taking turns, leaving me breathless.

—Say it, say you love it, that’s what you came for —the one underneath whispered in my ear, biting my earlobe, pressing me against his chest so I couldn’t get away.

—I love it… I love it, don’t stop, fuck me harder —I babbled, drool dripping down my chin.

My eyes were full of tears and my body was on fire. I was about to ask for a break when Sebastián stood in front of me and shoved his cock all the way down my throat, silencing me in the most effective way. He drove it into me with brutal rhythm, not letting me breathe, holding my head with both hands.

—This shuts you up, bitch —he said, panting—. Take a little cream to wash down the pill.

His load came a minute later: hot, thick spurts that filled my mouth and ran from my chin down to my tits. He slipped a little pill between my lips along with his discharge and made me swallow everything, clamping my jaw shut. I swallowed it almost without thinking, my body still being split open by the other two, who kept fucking me mercilessly. Barely a couple of minutes passed before a wave of heat rose from my belly and shut everything off: the pain, the fear, the shame. The only thing left was a sensation of pleasure so huge it frightened me. My cunt and my ass were pulsing at the same time, in sync, sucking the cocks of the two men who were tearing me apart.

—Pure magic, what a good aphrodisiac does —Sebastián commented, stepping away and wiping the tip on my cheek—. Want more, or have you had enough?

—More… I want more, please —I heard myself say, and the voice didn’t sound like mine—. Don’t stop. Keep fucking me. All of you, fuck me.

***

After that I only have fragments left. I remember two cocks moving inside me at the same time, each at his own rhythm, while a third shoved his into my mouth and a fourth came on my tits. I remember the first foreign load pouring hot inside my ass, and another one taking over right away, sliding in on the previous man’s cum. I remember that, even after the other girls arrived, there were almost always two or three men around me at once, jerking off over my face, lining me up, pulling it out and stuffing it back in in turns, marking my skin with slaps and bites.

I remember Bárbara sitting on my face, her shaved, perfumed cunt resting on my mouth, ordering me not to stop, grinding herself against my tongue while one man held her from the back of the neck and groped her tits. I licked her clit until she came trembling on my face, yelling whore at me, and the other partner was laughing in some corner of the lounge with two cocks in her hands. I remember Camila coming over to clean the cum off my face with her tongue, kissing my lips, passing other men’s load mouth to mouth before making me swallow it.

I remember being on all fours on the carpet, one behind me fucking my ass at full force and another underneath licking my clit while he penetrated me, and feeling a load of my own shoot up my spine like an electric shock, so long and so deep it made me tremble nonstop, drenching both their cocks and hands.

My last clear memory of that night is lying on the floor, in front of everyone, completely undone, legs spread, holes open, cum dripping down my thighs and cheeks, while the men adjusted their suits and left as if nothing had happened, some of them leaving an extra bill on my stomach. It was Camila who lifted me up, wrapped me in a robe, and took me to her car. She cleaned me as best she could with wet wipes, pushing my hair off my face, and dropped me off near my house, still shaking.

I got home with smeared mascara and my whole body feeling like a warm bruise. I didn’t have to explain anything: no one was waiting up for me. I got into the shower, let the hot water pour over me for a long while, watching the still-warm cum from so many men run down my legs, and only then did I allow myself to smile alone, not really knowing why.

The next day I counted the money on the bed. It was exactly what Sebastián had promised, not a peso less. And then I understood it wasn’t the money that had taken me there, nor what was going to make me go back.

I decided to tell this story because, after that night, I don’t have much else to add about that stage of my life: what came after were scattered hookups, the occasional threesome, nothing like it. I never again lived through an orgy like that, though it wasn’t for lack of trying.

Thanks to everyone who’s read my stories this far. I love telling these things, and it feels good to know there’s someone on the other side enjoying them. Keep writing to me. I hope you’re doing as well as I was that morning, walking barefoot down the hallway, still wearing the smile and with my cunt still throbbing.