Diary of a Secretary/Slut Ch. 09

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My weekend with Henry.
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Part 9 of the 11 part series

Updated 06/07/2023
Created 03/17/2013
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sex4every1
sex4every1
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Now, if there was one guy who liked extracurricular activities, it was Henry. He was a first class asshole. He always had the nastiest ideas, which usually involved completely humiliating either me or Becky. Whenever he approached me for a special request, I knew I'd end up with either a sore ass, a cum soaked face, ripped clothes, or any combination thereof. Usually, just listening to one of his requests, was enough to make my cunt water. This time was no different!

It was a Friday morning. When Henry came in, he greeted both me and Becky and walked straight into his office, only to call me two minutes later and summon me into his office. I knocked.

"Come on in, and close the door behind you," he said, "Take off your clothes, everything except your shoes."

I did.

"Now, get on your knees, spread your legs and play with yourself," he said.

I knew better than to pretend with him, so I quickly found my clit and started flicking it around.

After looking at me for a minute or two, he rolled his chair around the desk towards me, whispering, "That's it, you little slut, just don't cum without my permission."

When my clit was a big as it was going to get, I used my other hand to drive two fingers up my cunt, gently and started pushing them in and pulling them back. After watching me masturbate for a few minutes, he slowly took out his cock and started jacking off.

Several minutes later, I felt myself approaching an orgasm, so I opened my eyes, looked up at him and asked, "Can I please cum, sir?"

"Not yet," he said. A little frustrated, I stopped flicking my clit and fingering my cunt, but kept my hands close. When the threat of an orgasm was gone, I started up again. After another few minutes of mutual masturbation, I felt the onset of an orgasm again. Again I asked permission to cum, and again I was denied.

This happened two more times. Needless to say, I was getting frustrated. The time in between potential orgasms was decreasing rapidly, giving me less and less reprieve.

"Do you have any plans for the weekend?"

"Nothing written [pant] in stone [pant], sir," I replied.

"Good," he said, "My house is being fumigated so I'll be spending the entire weekend in the office. I could really use a little slut like you to keep me company and take all the abuse I can dish out."

"It [pants] will be my pleasure [pant] sir," I moaned.

Just like that, I had agreed to his ridiculous and disrespectful proposal.

"You won't get paid the overtime," he said, "There is no bonus in it, you won't be an employee, just a filthy slut, and I'll still expect you to be here on Monday!"

"Yes sir," I breathed, horny as fuck by now.

He was good. He knew what he was doing; making me play with myself, getting me all hot and bothered before dropping the question. Not that I would have said no otherwise, seeing him jerk off his big cock right in front of me would have been enough, I think.

Eventually, when I asked yet again for permission, with a broken voice, he said, "Yes, go ahead."

"Thank you sir," I grunted as I continued masturbating, quickly reaching the point of no return and started climaxing right in front of him, my body shuddering and convulsing wildly. Only a few seconds later, he rolled his chair a bit closer, scooted towards the edge of his seat, slid off and fell to his knees, aiming his cock slightly up, ejaculating all over my naked body.

As I felt his cum splatter against my thighs, stomach, tits and even a few drops on my face, I came even more powerfully and screamed loudly, really fingering the shit out of myself. He was kind enough to let me work myself through my whole orgasm, before kicking me out.

"Get out," he said coldly, as he got up, zipped up his pants and sat back down in his chair. I got up, grabbed my clothes, but before I could head out, he said, "Leave the panties, I don't want you wearing any today... as matter of fact, leave the bra too."

"Yes sir," I said, taking just my blouse, skirt and shoes and walking out.

In the hallway, I noticed music coming out of Brain's office. After putting on my shoes, skirt and blouse, I walked to his door, which was slightly ajar. As I peeked in, I could see Becky standing on Brian's desk, stripping to the music being played. From the looks of things, she'd been at it for a while already, as she was down to her underwear, her clothes scattered across the floor. Brian and David were sitting in front of the desk, facing her, jacking their cocks. Becky noticed me, but didn't react to my presence. I smiled and walked over to my desk, sat down and checked my email.

A few minutes later Donald walked in, greeted me with a drowsy hello, but then was also quickly drawn in by the music. He stopped in the doorway to Brian's office and looked on for about ten seconds. Suddenly he waved his hand, getting my attention and crooked his finger at me. He put his briefcase down and unzipped his pants, getting his dick ready by the time I reached him. I realized he wanted a blowjob, so I dropped to my knees. Donald immediately rammed his big cock past my lips and started shafting my mouth.

About a minute into the blowjob, I noticed - from the corner of my eye - David jumping up and frantically wanking his dick, shooting cum all over the carpet. Brian followed only ten or fifteen seconds later. Becky hadn't even taken her panties completely off yet.

"Don't stop," Donald said, as he was nowhere near an orgasm yet. Becky continued dancing, caressing herself and assuming all sorts of naughty positions. She eventually took off her panties, instantly causing Donald to fill my mouth with his warm sperm. Amazing! They'd probably seen her naked about a thousand times, fucked and abused her hundreds of times, done unspeakable things to her and yet here they were, all three of them shooting their loads at the mere sight of her undressing herself and dancing to some random music.

With no more cocks to drain, Becky and I went to clean ourselves up in the lavatories and then headed out for a very early and long brunch. When we came back, I sent a text to my husband telling him I'd have to work the whole weekend as there was some sort of emergency. I also added that I would take care of him tonight, and added a few naughty smileys. A few minutes, he replied that he was disappointed about the weekend but that he was looking forward to whatever I had in mind later that day. That "whatever" turned out to be nothing more than a quick blowjob before dinner and a sloppy, messy handjob in bed, just before going to sleep.

Saturday, 9h58 am

I entered the building through the garage entrance and took the elevator up to the sixth floor; I had never been in the building at this hour and was amazed at how quiet it really was; no people, no phones, no printers humming...

After hanging up my coat, I cleared my throat and said, "Sir, I am here."

"You're early, good... Carter's office, in just your underwear," I heard Henry shouting back. I put down my purse, took off my shoes, skirt and blouse and tiptoed into Carter's office. Henry was sitting behind the desk, holding a picture frame and wanking his giant, morning wood.

After ogling my body and my black panties and bra, Henry moaned, "Get over here and jack me off."

"Yes sir," I replied as I walked around the desk, curious as to what he was masturbating to.

When I was almost right next to him, he slid off the chair onto his knees and positioned the picture on the edge of the desk, right in front of his face. I was surprised to see it was a picture of Carter's wife, in a white bikini on the beach. I squatted down next to him, reached in between his legs and grabbed his throbbing dick, jacking it off while he drooled over the picture, only inches from his face.

"Oh yeah, fucking slut," he whispered several times during my handjob. I couldn't really tell whether that comment was directed at me or Carter's wife - probably both. All the time while I was jacking his cock, he didn't take his eyes off the picture, not once, even though he was constantly groping one of my tits or touching my ass.

After four or five minutes, he began shuddering and moaned, "I wanna cum on the picture."

Using my free hand, I quickly grabbed the picture frame and moved it under the desk, holding it under his purple cock head. He closed his eyes, arched his back and roared deeply and loudly as he dumped his huge, morning load all over the picture. When he was done, I put the frame back where it had been before, right in front of him. I was quite pleased with the result; I hadn't spilled a single drop. All of his thick cum had ended up on the glass overlay, resulting in a blurry, almost unrecognizable picture. When he opened his eyes and saw the result, he too was pleased, and said, "Excellent work Maya, now clean the pipe."

"Yes sir," I whispered as I bent down and slid my hot mouth over his shrinking dick.

"Oh yeah," he moaned, probably admiring the cum soaked picture, while I sucked the remaining spunk from his tube.

"Now, clean the picture with your panties," he said. I smiled wickedly and obeyed, taking off my black panties and scooping up Henry's sperm from the picture frame, making sure I rubbed the crotch of my panties over Carter's wife face a lot. He realized what I was doing, and groaned contented, as he flapped his half-flaccid cock up and down a few times.

"Dismissed for now, I'll call you when I need you," he said as he sent me on my way, "If you get too bored, feel free to use the TV in the old man's office."

"Yes sir," I smiled as I put my panties back on, sticky with his goo. About an hour later, after doing some online shopping and playing a few games on my smartphone, I noticed Henry coming out of his office and walking up to my desk.

"Follow me," he said.

I got up from my seat and followed him to the elevator. As there was no one else in the building it was quiet on our floor. After we got in, he pushed the button for the basement level.

"Ready to be abused?" he asked.

"Yes sir! Looking forward to it," I replied truthfully, knowing that Henry was as creative as he was perverted. His ideas were usually weird, wicked, degrading, but also a lot of fun. As I hadn't bothered with putting any clothes back on, I was still in my underwear, I didn't even have any shoes on. As soon as the elevator started going down, he said, "Take off your panties."

I complied. Barefoot and with just a bra on, I followed him out of the elevator into the chilly basement, parking lot. A few meters out, he stopped me and pulled a red gag-ball from his pocket and stepped in front of me.

He put the ball in my mouth, tied the strap around my head and looked me straight in the eye for several seconds. He could probably tell I was getting wet. He grabbed my hand and escorted me to one of the concrete pillars in the middle of the parking lot. Reaching into his pocket again, he pulled out a pair of metal handcuffs. Once again, my cunt tingled. He nudged me to my knees next to a metal pipe of some sort. Then, he grabbed my left hand, raised it above my head and secured it into one of the rings of the handcuffs, then did the same to my right hand. There I was, butt naked except for my black bra, on my knees on the cold concrete basement floor, tied up to a metal pipe and gagged, completely at his mercy. He smiled down at me and slowly took out his cock and started jerking it while enjoying the view from above.

He jacked his big dick for the next couple of minutes, his fist occasionally bumping against my face. I just waited and tried to look as submissive and as slutty as I could. Then, without as much as a grunt or a moan, he suddenly erupted all over my face. It wasn't as big of a load as he had dumped on the picture frame earlier, but there were still dozens of drops, enough to moisten my entire face. When he was done ejaculating, he squeezed the last bit of cum out and wiped it on the gag ball, then zipped up.

Then, he pulled out a pack of cigarettes and lit one up, while he continued to look down at me. I simply sat there, in that submissive and degrading position. If only my husband could see me now, I thought to myself. After leisurely smoking two cigarettes, and keeping me in that degrading position for over ten minutes, he finally unlocked my cuffs and undid the gag.

"You did very well," he said, condescendingly.

"Thank you sir," I replied.

"Ready for your next assignment?" he asked as we walked back to the elevator.

"Yes sir," I replied, surprised at the timing, considering he had just cum. As it turned out, his next assignment wasn't for his benefit; it was designed to humiliate and degrade me some more.

"Use the copier on the fifth floor to Xerox your cunt, make about a hundred and fifty copies and put a copy on every desk on the third, fourth and fifth floor."

"Yes sir," I replied.

When we got into the elevator, he pushed the button for five and six. For a moment, I looked down at my panties, but realized they would be of no use as I was about to Xerox my cunt, so I just left them on the elevator floor. When we reached the fifth floor, I got out and looked back at Henry for a moment. He just nodded and let the door close. I headed towards the lavatories, cleaned his cum off my face and then proceeded to the copier in the back office. I opened the lid and carefully sat on the glass plate, leaned slightly forward and opened my legs, so that the machine had a clear view of my twat and pressed the copy-button.

The copier came to life, scanned me and spewed out a paper replica of my ass and cunt, lewdly obvious, even if it was just a black and white copy. I hopped off and made 150 copies of the original and then walked by every desk on the fifth floor, putting a copy on each one, as ordered. Then, I did the same thing on the third and fourth floor. With just fifteen copies to spare, I took the stairs back to the sixth floor. The whole endeavor had taken me slightly over twenty minutes.

I walked into Henry's office and knocked on the open door. Henry, who was lying on his leather couch, resting, looked up and said, "Yes?"

"I completed my assignment, sir, all three floors," I said, with a tad of misplaced pride, still naked except for my black bra.

"Good girl, now go and watch some tv, I'll come and get you when I need you," he said condescendingly.

"As you wish sir," I said, walking out and throwing the remaining copies of my twat in the nearest trash bin, then walking over to my desk to put my skirt, blouse and high heels back on. My panties were still on the elevator floor, so I pulled out a new pair from my desk drawer and put them on. Then, I headed towards Jerry's office to watch some tv, as ordered.

Nearly two hours later, Henry walked into to Jerry's office and asked, "Hungry?"

"A little bit sir," I replied, thankful I'd had eaten a big breakfast.

"How about I fuck your stupid little twat right here on Jerry's desk and then we head out to that Italian place on Langdon Avenue?"

I got up and walked around to the front of the desk, where he was standing and as I unzipped my skirt, I replied, "I am not really in the mood for Italian, sir."

"No problem, what are you in the mood for then?" he asked, as he unzipped his pants, pulled them down along with his boxers and stepped closer, while I pulled down my panties and reclined on the desk.

"Mexican?" I asked, as I spread my legs and looked down at his cock sliding into my twat.

"Too spicy," Henry replied as he began fucking me, "Chinese?"

"Perfect," I said as I started moaning, rocking back and forth on Jerry's desk.

"Good, now, let's speed things up a bit, talk to me," he said. I could feel his cock wasn't as hard as it normally was, so I knew he was looking to me to help him out with some dirty talk.

"I am a fucking cunt, sir... a good for nothing little whore... except for my three fuck holes, I am a dumb, useless bitch," I whispered in my most seductive, yet serious voice. He grabbed my legs, spread them even further and really pounded into me. The whole desk shook and pretty soon several gadgets started dropping to the floor. That seemed to do it, as I felt his cock growing inside of me.

"Fuck my stupid little twat," I edged him on, "Shoot your cum in me, that's all I am good for!"

He banged me for another three minutes or so, before unloading deep within me. He pulled back, grabbed Jerry's stapler and wiped his tip off on the bottom of it, leaving behind a big glob of cum. I was surprised at myself that I would get aroused by that kind of disrespectful behavior.

As he pulled his pants and boxers back up, he said, "There is an evening dress for you in the second stall of the bathroom, go clean yourself up and put it on."

I complied, walking into the bathroom, where I did indeed find a bright red, long slim-fitting evening dress, with a split to above the knee. It was provocative, but still classy and gorgeous. I cleaned myself up, put on the dress, tweaked my makeup and walked back out.

He drove us to the Chinese place up on fifth, where we had a nice, four-course meal. We talked about sports, the weather, work, some tv-shows I watched, and of course Becky and the other guys.

In the car back to the office, I suddenly got a phone call.

When I saw it was my husband I was about to dismiss the call, but Henry said, "Go ahead answer it, put it on speaker," as he pulled over to the side of the road. Surprised, but unwilling to disobey him, I answered it.

"Hi hon," I said as I pushed the speaker button.

"Hi babe, how are you?" he asked, as I felt Henry's hand on my leg.

"Oh I am fine, Becky and I are in the car, getting something to eat," I said, explaining any car noises he might hear in the rest of the conversation.

"How's it going? When do you think you'll be done?" hubby asked, as I felt Henry's hand sliding up the split of my dress, touching my panties. Instinctively, I shifted in my seat and opened my legs as far as I could.

"Oh, we're getting there, slowly, but I think we're on the right path... a few more hours, maybe a little clean up tomorrow morning, but I think I'll be home tomorrow afternoon in any case."

Meanwhile Henry was - literally - trying to get into my panties. The split of my dress however was proving more troublesome than he anticipated, so he suddenly grabbed both sides of the split and gave it a powerful yank, ripping it all the way to my cleavage, effectively splitting the dress in two. Startled, I looked down to see Henry revealing my underwear.

"You okay?" my husband asked, as he had heard me gasp.

"Uh, yeah, fine, Becky nearly ran someone over, that's all," I said, thinking on my feet, as Henry pushed my bra up, bringing my tits out into the open.

"Well, tell her to be careful, I want you back in one piece," my husband quipped as Henry started cupping my tits, playing with them. I looked down at his hand and then at his face, biting my lip.

"No worries, we're almost there," I said.

"Oh ok, I'll leave you guys to your dinner then," hubby said, taking a hint. But Henry signaled me to wait. So I covered the phone with my hand and looked at him.

"Tell him to come over, tell him you wanna fuck," Henry whispered, surprising me.

"What? But how..." I whispered as I felt him fumbling with my panties.

"Not my problem," he replied, as I shifted in my seat to accommodate him.

"Maya?" I heard my husband say.

"Hello... Maya?" I heard him say again as I felt Henry's fingers enter my wet twat.

"Sorry, I had to wait until I was alone in the car," I fibbed, "I just had a very naughty idea, why don't you come on over... I wanna fuck you!"

"What? Are you shitting me? But how are we..." hubby said, baffled, this was no doubt the last thing he expected me to propose.

"Don't worry about it, are you in or not?" I asked, pursing my lips together as I felt Henry starting to finger fuck me. I used the handle next to my seat to recline completely and spread my legs as wide as I could, putting my feet on the dashboard and bending my knees, opening myself up to the maximum extent. Henry really started fingering the shit out of me, so I knew I was going to be making some suspicious noises soon.

sex4every1
sex4every1
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