Secretaries Are Supposed to Be Sluts

By Henley Fletcher

Published on Sep 25, 2009

Transgender

This story is a work of fiction. Any resemblance to actual people, places, or organizations is purely coincidental. Author takes no responsibility in damage to your home, computer, or relationship based on your actions during or after reading this story. No animals were harmed during the writing of this story. Feedback will be accepted at the address above. Above all, thank you and enjoy!

  1. Dinner at Riverside

All the note said was "Dinner. 8:00. Riverside Grill." It was in my secretary's handwriting but I knew it must be a message from Carrie. Andrea, that's my secretary, always hated taking messages from Carrie and would only write down the most important parts. Riverside was our old hangout where we would drink our weekends away. It was a quarter to six now and by the time I got my jog in and showered, I could make it to Riverside by 7:30.

I paged Andrea in and asked her to clarify the message. It was a shame that she and Carrie couldn't get along but, given the circumstances, I understood. She hit the lights in the main lobby now that everyone was gone and came into my office. She sat her firm little butt on the corner of my desk and I rubbed her leg as she told me that Carrie had some big news for me and thought that Riverside would be perfect to tell me but that she wasn't supposed to tell me that. Andrea leaned in to me as I pushed my hand further up her skirt.

"Are those the panties I bought you?" I asked, feeling the edge of the lace that stood between my fingers and her supple pussy.

"Mmmhmmm" she said, proud to be showing them off. She swung her leg around my desk and moved her butt onto my crotch.

"Would you like to see them better?" she asked, pushing her skirt up to her navel as she leaned in and kissed my neck.

I didn't get a very clear look at her lacy little butt as I was unbuttoning her blouse and unclasping her bra. She wrestled with my belt buckle but it wasn't too difficult to get clothes off of my 140lb frame. She arched her back and placed a breast in front of my face, grinding on my crotch as I squeezed her little bottom.

"Hey! Let's do it in the conference room!" She squealed.

The conference room had twelve foot floor to ceiling windows facing onto Berker Street but I agreed anyway. Fucking Andrea was a privilege for any man and if she wanted to do it in the conference room, then we'll do it in the conference room.

She hopped off my lap and pranced out of my office leaving her skirt and shoes on the floor. I watched for a moment as her flawless body pranced past the windows of my office. I assumed this meant I was supposed to follow and I quickly made my way toward the conference room leaving a trail of clothes behind me. When I got to the conference room, Andrea had pulled out a chair for herself and was naked and waiting.

"Wet me up first?" she asked. I could tell from the shimmer between her lips that she was plenty wet already but I dropped to my knees and went immediately for her clit with my tongue. Andrea's juices were starting to pool on the leather chair and I was as hard as a rock. She grabbed my head and forced it deeper into her dripping pussy. She arched her back as she flooded my face with the juices of her orgasm and she stood up forcing my head back and my tongue deeper inside her. She pushed herself down, knocking me backwards. Lying on the floor of the conference room for all the commuters to see, Andrea grabbed my cock and slid it inside herself as she lowered her body onto mine.

My god, Carrie could never do it like this. Andrea rode me and pushed her sweet little cunt onto my cock like she was trying to kill it. She grabbed my hair and pulled my head toward her as she fell on her back, flipping me on top of her. I can't believe we pulled off a maneuver like that while I stayed inside her but that was her signal that it was my turn to get off. She wrapped her legs around my waist and, with her being 5'10" and my being 5'6", her breasts lined up perfectly with my face. I pounded away at her perfect little pussy all the while watching her D-cup breasts pull against her skin as they bounced to the rhythm of our bodies. She continued to pull my hair, screaming and writhing as we both achieved orgasm.

Well, now that my jog was done, it was time to hit the shower.

"You want to join me?" I asked, pulling out of her pussy as it started to ooze my cum onto the conference room floor.

"Of course!" she replied, rolling over onto her side, gazing at me with a look that I never saw from Carrie anymore.

We collected our clothes and went to the shower in the warehouse. The shower was only there in case one of the workers accidentally coated themselves in some horrific chemical. OSHA standards. But, after hours, it worked quite well for cleaning up before I went home.

"Are you going to leave Carrie, yet?" Andrea asked as I was lathering up to rid myself of her smell. Not that I wanted to.

"You know I can't, baby. She owns half of this." I said, gesturing to our warehouse full of boxes waiting to be shipped to destinations unknown.

"I know, but you could divorce her for... something. I don't know. Tell her you're sick of trying to have kids with her."

"But that still leaves us without anything. Do you think that I could divorce her without her starting to take an interest in what goes on around here? She'll fire you the minute she finds out how much I pay you and she'll hire a temp to answer the phones. That's if she even gives me that!"

Andrea had been bugging me to divorce Carrie for a year now. Almost since the time we started sleeping together. We redressed ourselves and I kissed her goodnight as we headed out to the parking lot, her Audi and my Mercedes the only cars left in the lot.

As I eased my Mercedes convertible out onto Berker, I turned my thoughts to Carrie. I wondered what her big news was. Maybe she was finally pregnant. We'd been trying for six years now. She had visited specialists and timed our sex down to the minute she thought she dropped an egg. It was rather annoying, really.

I pulled into Riverside Grill at a quarter to eight. I didn't see Carrie's car in the lot so I went inside and got us a table near the windows overlooking the river. Carrie walked in as soon as I'd ordered us a bottle of wine and lit a cigarette.

"Hey, baby!" I said, standing up to give her a hug and pull out her chair.

"I know everything. Sit down." she said cold and quietly into my ear as I froze in our embrace.

So that was her big news? I sat back down and took a long draw on my cigarette while she pulled out her own chair and sat down. She gave me the iciest stare I think a man could handle. Like an interrogator waiting for the right moment to begin. I was afraid my cigarette would extinguish itself from the chill directed our way.

"Tonight's jog was your last." She said. It was apparent that when she said she knew everything that there was a pretty good chance that she did know everything.

"I picked Riverside because we both know a lot of people here and your job is to look like you're enjoying yourself. I'm not asking for a divorce. Not yet. But there are going to be some changes. A lot of changes. You work for me now. You can tell your twit of a secretary to start looking for a new job. No... I'll do that. You get her desk, I get yours. I've let you run this business for five years and now it's my turn." She said in a way that made my suspect that it was rehearsed.

"I have receipts, Tim. I have receipts for Victoria's Secret, plastic surgery, a fucking Audi!" She said, trying to keep her voice quiet while she made clear how much she knew. "I drive an Accord and you bought your fucking secretary fuck toy an Audi? Fertility treatment is too expensive but you can buy new tits for your side dish slut?"

I tried not to smile as I mulled over Carrie calling Andrea a "side dish". Andrea was an entree of epic proportions. If Andrea was a juicy bloody rare sirloin, Carrie was probably something like cold peas.

"And I swear to God, Tim, if you got her pregnant I'm going to slice off your fucking balls. We've been trying for six years. Six years! I count the days until I'm fertile and you can't even..." She trailed off, sitting back in her chair and reaching for my pack of cigarettes as our waitress brought us our bottle of Cabernet. Carrie had quit five years ago when we were scraping money together to start Plastech. Under the circumstances, I could understand the need for a little nicotine.

"So here's the deal," She said, lighting her first cigarette in half a decade. "What you have is mine now. Your Mercedes is mine, your office is mine, your freedom, and most importantly," she leaned across the table, smoke easing from the corners of her lips, "your ass is mine. You get to be my secretary now. You know I don't know the first thing about high-impact plastics, so I can't get rid of you. But, I can sit you right outside my office so I can watch every fucking move you make."

Well, this could have gone worse, I thought to myself. She wasn't trying to dump me onto the streets with no house, no money, etc.

"Give me your keys." She said, tossing the keys to her Honda on the table. I reached into my coat pocket and felt the key to my baby - my Mercedes SL500. I dropped them into her hand and she paged through the keys on my ring. "What's what here?" She asked.

I told her which key was my office, which one was for the front door, the master key to the warehouse and the maintenance rooms and which one was our house. I think I may have put a little emphasis on "our" and I hoped that didn't remind her that there was still something else she could take away.

"Oh, and give me your phone. I need your sales contacts." She said. I pulled my Blackberry out of my jacket and set it on the table between us. Thankfully, I thought, my Blackberry was all sales contacts and employee information.

I slept in the spare bedroom that night even though Carrie never came home. I got up a little late and took a shower. For the first time, I wasn't looking forward to going to work.

When I pulled into the Plastech parking lot at 10:30, my Mercedes was sitting in my reserved spot. I'm sorry, Carrie's Mercedes was sitting in her reserved spot. No black Audi to be seen. I wondered how it went down this morning when Andrea showed up for work. I was glad I wasn't there to find out.

I entered through the main lobby and found my new desk covered in boxes of things from my office. Carrie was sitting at what used to be my desk, on the phone with someone and she glanced at me through the windows that separated her office from my new home in Reception. She signaled me into her office and I pulled up a chair as she finished her conversation.

"No, I'd really just like to touch base with everyone. I may organize a manager's meeting but I'd really like to sit down with each of you. No, thank you!" She hung up her phone. It was evident that she was taking her new position seriously. "Alright, Tim," she said, directing her attention at me. "If you didn't hear that, I'm going to be sitting down with each of the managers and getting a little run-down of what goes on here. Go set up your desk and then make me an organizational chart so I know who does what around here."

For the rest of the day I complied with Carrie's request to send in manager after manager and even her request for a chicken salad sub from Gordie's Deli. Gary the sales manager, Phillip the production manager, Alan the shipping guy... She'd just about made her way through the entire organization by 5:00. The only one left was Jeremy the warehouse supervisor. I paged him in at just before five o clock when his worker bees were all leaving for the day. As soon as he entered Carrie's office, he dropped the blinds and within minutes I could hear the familiar sound of the big wooden desk trying to scoot across the tile floor. The sounds of flesh on flesh, Carrie's screams of ecstasy, and knowing she was obviously enjoying being railed by another man were too much for me to bear and I grabbed the keys to the Honda and made my way out the door.

"She was going to watch every move I made?" I asked myself as I sat waiting for a break in traffic to let me get away from this god-awful building. It was starting to sound like she was going to make me watch every move she made as she slowly brought down my life. Why did I care so much that Carrie was fucking Jeremy on the desk that I'd fucked Andrea on? Turn-about's fair play, I suppose, but revenge is a mother fucker.

I thought that maybe I'd found the first thing that scotch couldn't cure but that wasn't going to stop me from trying. It was a crisp night but I sat at the patio table with an ashtray and a rocks glass with more than enough cigarettes and scotch to fill both plenty of times over. Did it bother me because Jeremy was everything I wasn't? At 27, he was six years younger than Carrie and I. He'd worked in the warehouse since we'd started the company and his body showed it. He was young, in shape, and I'm sure possessed a virility and stamina necessary for moving crates and boxes eight hours a day. Was it because I feared that he could give her something I couldn't? I knew that it was my fault we couldn't conceive. Was I that scared that Carrie would find me too worthless to keep around? Was all this "I'm your boss, you're my secretary" stuff just a way of transitioning herself into a stable position in the company so she could reduce her need for me there, too? I was starting to make myself sick and I was hesitant to blame the scotch. It was far too easy to blame Carrie.

Fuck the guest room. It was eleven o'clock and Carrie still wasn't home so if she wasn't going to use the master bedroom, I was. I undressed and sprawled out, taking up as much of our king sized mattress as I could. Maybe there could be something positive here. I let myself succumb to the effects of the scotch and faded out.

The sounds of Jeremy fucking my wife filled my dreams and, even in an alcohol fueled stupor that should have had me comatose until the morning, I slept awfully. In my dreams I could feel the bed moving and Carrie screaming as Jeremy filled her with his cock. I awoke with a start to find that it wasn't a dream at all. There she was, bent over on the bed, her face just inches from mine as Jeremy fucked her from behind.

"Oh, he's awake!" She said, taking a quick break from gasping for breath. I tried to roll away and jump out of the bed, overwhelmed with what seemed like an alternate reality but my legs wouldn't move. Before I knew what was going on, Jeremy grabbed whatever was binding my hands together behind my back and brought me into a sitting position. He knelt on the bed in front of me, his enormous cock dripping with Carrie's juices.

"Well? Aren't you going to suck it?" Carrie asked. What?!? Was this real? "I thought secretaries were supposed to suck cock." She said, as if she was questioning my purpose in life.

Jeremy grabbed the back of my head and pressed my face toward his glistening erection. "At least it would taste like Carrie, right?" I told myself. He pressed his cock up to my mouth and pushed it through my tightened lips. My god, he was hard. I don't think I could have pushed my cock through a bowl of Jell-o like the way he pushed his past my lips and into the back of my throat. I felt myself gagging as he held it there for a second, then backed out and began ramming it in and out of my mouth.

Everything still seemed surreal. Carrie was lying on her back rubbing her pussy as she watched Jeremy fuck my face. I was bound at the hands and feet, gagged by what must have been a 10" cock that seemed to want nothing more than to lodge itself in my throat. Yesterday, I was fucking a freaky little twenty-five year old with brand new D-cups and now I was tied up in my own bed watching my wife get off on watching another guy's balls slap against my chin as he forced my mouth up and down on his raging cock.

"You want me to cum in his face, Car?" He asked.

"Sure, but make sure he swallows all of it!" she said.

Jeremy continued to ram his cock down my throat until I felt it swelling and pulsing. I knew his orgasm was coming soon and I braced myself for my first encounter with another man's seed. No amount of bracing could have prepared me for what happened as he let loose stream after stream of hot cum into my throat. I fought off gagging and had no other choice than to swallow it. One, two, three gulps of Jeremy's cum and my mouth was finally left vacant save the lingering taste of his semen.

"Now get out of my fucking bed!" Carrie yelled.

Jeremy let loose the clasps that held my extremities and I fell out of the bed. I scrambled to my feet and made my way quickly downstairs. All my clothes were in the master suite, so I couldn't go smoke. I poured myself another scotch to calm me down and cut the taste of Jeremy's cum from my mouth.

I went to the guest bedroom, or, I suppose, my bedroom and found a little pink box about 12" cubed sitting in the middle of my bed. To my sexy little secretary, the note said. I opened the box to find a black pair of Victoria's Secret panties with white lace and a card.

You're my secretary now so I want you to look like one. Wear these tomorrow. The rest of your clothes are in the closet. -Carrie

Well, at least she was nice enough to move my things before evicting me from our bedroom. I locked the door this time before I let the scotch take me back to none-of-this-ever-happened-land.

Next: Chapter 2


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