Secretaries Are Supposed to Be Sluts

By Henley Fletcher

Published on Oct 9, 2009

Transgender
  1. Sales call

"Timmy, can you come in my office, please." Carrie squawked through my speakerphone. I should have never shown her how to use the phone system. I went around the glass and into her office.

"Take a note, please." She instructed. I sat down in one of the chairs across from her desk. "Cross your legs. No one wants to see up your skirt." She said. I sighed and crossed my legs, placing a legal pad on my lap. "At the knees." She said, raising her eyebrows showing that she did not expect to have to give me such detailed instructions.

"First thing tomorrow morning, we need someone to make a sales call to ComFreight in Leuton. Tomorrow at four we're going to have a companywide meeting to make clear the new power structure. Sometime next week I'd like someone to make a pitch to AGC - I think we can increase the durability, and the useful life, of their bowling pins by 40%. Joe is working on a prototype right now. Check on his progress and set up an appointment with them to coincide with when he'll be done." Good lord, she was taking this seriously. I hadn't pursued new customers in nearly a year. Between bulletproof glass offerings and our defense contract, we weren't hurting for revenue.

"Add these to the public calendar, CC me on the email to everyone about the meeting, and let me know when you set up an appointment with AGC." She said as I scribbled down her instructions. "You're dismissed." She said, waving me off to complete my tasks.

It was almost five o'clock on Thursday and half of the staff had already left. I emailed Gary to ask for a sales guy to make a call to ComFreight, the managers list to have them notify their subordinates about the team meeting, and Joe to inquire about this new project. Despite being the proxy between Carrie and the rest of the company, I felt out of the loop. It was a pretty common feeling now as things kept happening beyond my control. At a quarter after five, I grabbed the keys to the Honda and made my way to the parking lot. I hurried to my car to escape the cat calls coming from near the loading dock. I wanted desperately to stop at the bar on my way home but I couldn't go in there looking like this. I wasn't looking forward to going home, but what choice did I have?

I pulled the Accord into the garage and immediately went in and shut myself in my room. I stepped into the guest bathroom and started running a warm shower. I tossed my blouse onto the floor in the bedroom and slid off my skirt. Standing in front of the mirror in the bathroom I could see my black and white lace panties over my smoothly shaved body. I turned around and looked at myself over my shoulder. Aside from the welt on my ass from where Carrie had hit me and the fact that I knew who I was, I was kinda sexy. At five foot eight and a hundred and forty pound, I wasn't the manliest to begin with. I mean, if I'd seen my ass in a magazine, I would want to fuck me. Maybe this wouldn't be so bad if I could go a day without getting bent over something.

I slipped out of my panties and caught a glimpse of the tampon string dangling from my behind. "Oh, that'll have to go." I said aloud as if there was someone there to hear me. Maybe it was to reassure the Tim I knew myself to be. I squatted down in the shower and slowly pulled on the string. I felt the cotton work its way through my sphincter and my ass flared to expel its captive semen onto the shower floor. Judging by how much I watched run between my legs and down the drain, Barry could have impregnated half the state with that load. Surprisingly, I felt empty. I reached my hand between my legs and touched my asshole. It was probably big enough to fit a golf ball and I slid three fingers in. I could still feel Barry's cum clinging to my insides. I forced my fingers as deep as I could, pulling out a few more strings of ejaculate. I watched them go down the drain and I wished they could take my day with them.

I lathered my shampoo into my hair and soaped up my smooth body. It had been days since I'd gotten off - not since I'd last had Andrea on the floor of the conference room. Standing under the water, I started rubbing my hairless cock. After getting so intimate with both Jeremy and Barry's packages, I was suddenly much less impressed with mine. I thought five inches was pretty normal but looking down at my full erection, I felt inferior. For what I didn't have in my pants, I had made up for with power and charisma. I owned my own company, drove a brand new Mercedes, and whomever I couldn't win over with my looks, I could woo with my wit, charm, and my pocketbook. Now I had nothing - just a domineering wife, a broken life, and a small penis.

After the hard realizations and resignations, I had a hard time maintaining an erection. On the other hand, there didn't seem to be a shortage of people who wanted to fuck me. I reached my hand around my ass and slowly fingered my still gaping hole. I plunged two fingers into my tender ass and worked them in and out, feeling where my insides had been stretched. I thought about Jeremy forcing his huge cock down my throat and Barry fucking me raw and I felt the first drop of precum leak onto my hand. I picked up the pace, working in three fingers now as I ran my hand up and down my neglected dick. I dropped to my knees in the shower and bent forward, the water running off my back and past my hand as I pushed my fingers deeper. I was jacking off furiously, trying to match the rhythm of my left hand. I felt the orgasm coming and I pulled my hand from my ass and grabbed my balls. They tingled, begging for me to loosen up and let fly the orgasm I was holding back. All at once, it rushed through my body sending shockwaves through my legs and streams of cum past my face.

My ass was sore and my legs were unstable. I slowly stood up, holding the side of the shower for balance. Another shiver drove through my body and my penis made one last twitch before settling into an incredibly sensitive flaccid state. I finished rinsing the shampoo from my hair and I shut off the shower. I grabbed a towel from the rack and dried myself.

"Why did I just do that?" I asked myself. Obviously, I did it to get off, but why did I have to reflect on getting fucked by my coworkers? No matter how I got there, that was a damned good orgasm. I replaced the towel on the metal rack in the bathroom and I went back out into my room. I grabbed the terrycloth robe off the floor, threw it on, and went to the kitchen. I grabbed a Heineken from the fridge and returned to my room. I occupied myself with internet poker until there was a knock on my door.

"I appreciate you sending off those emails for me, but I have a better plan." Carrie said. A better plan? What was the original plan? And, besides, I was at home. I didn't want to talk about work.

"Why don't you and I go to Leuton on the sales call? I want to be a part of it and you know this stuff better than anyone." I sat down on the bed, questioning why this was the nicest thing she'd said to me in two days.

"You need to be up and dressed by seven. I packed a box of stuff to take with us. We can leave straight from here." I nodded in agreement and she left without another word.

I slept fitfully, again, that night. It was hard to reconcile myself with who I thought myself to be. Eventually, I didn't care who I was, I just wanted to be able to sleep. At 6:15 I awoke to knocking on my door. Again, I answered, knowing it was Carrie.

"I thought that since this was your first time getting dressed on your own, you may need some help." She said without much emotion. I was 33 years old, who did she think she was offering her help to dress me? She walked to my dresser and pulled out a pair of pink panties with black frills, a pair of garters, some stockings, and a little demi-cup bra that matched the panties. Then she walked to my closet and pulled out a flat grey pinstriped skirt with a matching jacket and a white blouse.

"There you go. You'll look pretty professional in that." She said with a smile. "Go ahead, I want to see how you look."

I looked at the clothes lying on the bed. The panties and bra I knew how to do. I wasn't so sure about the stockings and garters. Carrie could tell I was a little unsure and she guided me through the process. I slid the panties over my smoothly shaved legs; Carrie helped fasten my bra and then pushed the garters high onto my thighs. She placed each foot in one of the stockings and rolled them up my legs. I slid on the skirt and fastened the clasp at the waist, tucked in my blouse and donned my jacket. Women's suit jackets were not terribly unlike men's except that they buttoned the wrong way. At the end, she had me stand in front of the mirror.

"Well, I'd say you look quite nice." She said. The bra was a 36A and its cups stuck out from my body just enough to be perceptible under my jacket and blouse.

We got in the Mercedes and didn't say anything until we got on the highway to Leuton, except to order our morning coffee at the Dunkin Donut's drive-through. It was nice to be in my car, but strange to be in the passenger seat. An hour and a half later, we pulled up to ComFreight.

ComFreight is a commercial rail shipping company and ever since Carrie had mentioned it yesterday, I had been picking my brain trying to figure out what they would need high-impact plastic for. The days of train robberies had long past, so they probably didn't need bullet-proof glass. Maybe they needed lightweight shipping containers, but I didn't think our factory was set up for something of that size.

Carrie and I checked in with the receptionist and we were guided to a conference room with ten people already seated around the long table. We sat down and I began by briefly describing our business.

"How much do you know about trains?" the man seated directly across from me asked.

"To be honest, sir, not much. But with a better understanding of your needs, I'm sure we can find a way to meet them with the utmost efficacy." I replied, trying to be as businessmanly as possible, despite my attire.

"Would you like us to show you?" He offered, standing up from the table. I took this as my cue to stand as I assumed we were going to look at the issues he had in mind for us to solve. As soon as I did, I was met with two sets of hands. One each on the back of my neck and one of each on my thighs. They forced me up upon the table and Carrie reached into the box we had brought and handed something to a third man who had risen from the table. He placed a shackle around my thigh just above my knee and linked it to my arm just above my elbow. He repeated this on the other side so that my right knee was affixed to my right elbow and the same with my left. He rolled me on my back on top of the conference table. I was practically immobile and I could see Carrie still in her seat rummaging around in the box.

"See, you stay there and we take turns." The first man said, removing his pants and shoes. I felt a fear tear into me as I fully understood what kind of train he was talking about. He carefully unbuttoned my jacket and my blouse, exposing my pink frilly bra. He pushed my panties up to my knees and pulled me toward him, spinning me around and sliding me across the conference table. He spat in his hand and rubbed his growing cock and I knew were this was going. As I lay bracing myself for the feeling of another cock to penetrate my already sore asshole, another man grabbed my head and turned it to the side. He pressed down on the side of my head, trapping it against the table as he readied his cock to enter my mouth. Eight other men stood ready, hanging their clothes on their chairs, readying themselves to take their turn at my face and ass.

I felt the first man press his cock against my asshole and he was in without a struggle. My ass flared and enveloped his cock as he pulled it out and forced it back in. Men standing around were forcing their hands into my bra, pulling on my nipples as they watched me getting fucked from both ends. They grabbed my hands and jacked themselves off while they waited for their turn in my ass.

After a quick hand signal, the two men fucking me traded places. A new cock entered my asshole and the first went into my mouth. I could tell he was ready to get off as he grabbed me by the back of the head and pounded my face. I felt his cock swell and his jizm flooded my mouth. As soon as I had swallowed, his place was filled with another cock ready to fuck my face.

Another hand signal and another 3 seconds of emptiness before the cock from my mouth was forcing open my ass and the cock from my ass ready to unload into my throat. My nipples were becoming sore as men pulled them and twisted them. Three men came in my ass, six men came in my mouth and one did both. As I lay there on the table, oozing cum from my ass and tasting of seven different men, they all refit their suits and ties and they each handed Carrie a small stack of bills on their way out the door.

"What the hell was that?" I asked her as soon as they all had left.

"You made me a thousand bucks today. Forty-seven more of these and you will have paid off the tits and the Audi" she said. She unfastened the shackles tying my extremities together. I pulled up my panties as I wriggled off the table. My ass was sore from taking ten men and I could feel the cum rushing out of my asshole and down the back of my leg.

"Come on, we still have a team meeting this afternoon." She said, slapping my ass as she dropped the shackles back in the box.


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