Miss Allison Ch. 06

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David revels in filthy, nasty anal sex.
4.6k words
4.67
20.7k
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Part 6 of the 7 part series

Updated 01/09/2024
Created 11/18/2023
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Miss Allison (Ch. 06)

soppingwetpanties

The essential background on this storyline is embedded in this chapter, but you'll get more out of this story by reading Chapters 1 through 5 (published in the BDSM category, each chapter 1-2 Lit pages). I chose to publish this chapter in the Anal category because it features raunchy anal sex. Please assume that all characters were fastidiously hygienic and well lubricated.

This series is dedicated to the real David. It's my spin on his wicked fantasies.

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters in sexual situations are 18 years or older.

Chapter Six

It was dark and cramped under Claudette's desk. She was Miss Meghan's twenty-one-year-old intern who was one of many women who had a copy of my sex survey - - the survey where I bared all about my deepest and darkest perverted sex fantasies - - unspeakable acts I would have never dreamed of asking my ex-wife to perform with me.

My next-door neighbor, Miss Allison, discovered the survey in my home office and promised me she'd make me perform each one of the submissive sex acts explored in the survey's fifty questions. During the past week I was whipped, pegged, pissed on, and made to eat my cum and the cum of another man. Along the way Miss Allison recruited my boss and her sorority sister, Miss Meghan, as well as Miss Lori, another sorority sister of hers, to humiliate me. It was the best week of my life.

As a fifty-five-year-old balding, overweight man, Claudette, a tall blonde blue-eyed college transfer student from France, should have been a subject of my wet dreams, and not a part of my reality, but the survey unlocked a latent need of Miss Allison and Miss Meghan to dominate a man, and somehow Claudette had been drawn into the mix.

Claudette was curious about my lifestyle choice and ordered me under her desk after I stopped by her carrel, intending to say good morning and maybe get to know her a bit better over a cup of coffee. With me under her desk she edged her chair forward so my head was between her bare legs. I got a good whiff of her young pussy and suddenly the rest of my brain went blank - - nothing else mattered. She didn't object when I kissed the inside of her thigh so I continued upward until I got to her panties. They were sopping wet. That was a good sign. But she needed to take them off if I was to do anything more.

"Please?" I asked from under the desk.

"Oh Daveed. You're a naughty one," she answered. But she was a naughty one as well. She lifted her bottom off her chair, allowing me to slide her panties to her ankles. It was only 9 a.m. I hadn't even finished my first cup of coffee and I was going to have my first helping of pussy. It was going to be a good day.

Her panties removed, it was an easy task to push my face between her smooth firm thighs until my lips met her nether ones, ripe and juicy. I mashed my face into her hairless crotch, wanting her to mark me with her feral scent. Her hands gripped my head, moving it back and forth to increase the friction of my lips against her clit.

"Oh . . . Dav . . . eed . . ." she moaned as my tongue probed the depths of her drenched cunt. I hadn't tasted twenty-one-year-old pussy since I was . . . well twenty-one. There was something indescribably wonderful about fresh young pussy. I was busy licking her, wondering how I could wedge my head underneath her cute tush to rim her asshole, when I heard footsteps outside Claudette's carrel.

"Good morning Claudette," a man's voice said. I was sure it was the CFO, Ted Hendrickson, Miss Meghan's direct report. "I was looking for David Elliott. Have you seen him?" he asked, obviously unaware I was eavesdropping from under Claudette's desk.

I stayed still and quiet. I felt ridiculous in my coat and tie hunched under a desk while my boss's boss made small talk with Claudette.

"No, I have not," Claudette said in her cute French-accented English, not paying any mind to me.

I heard Ted get closer. The only thing separating me from Ted was the front panel of Claudette's desk. If he looked down he would be able to see my shoes.

"So, how do you like the U.S.?" Ted asked, making a clumsy attempt to engage in small talk with the office's newest and hottest woman. He had the reputation in the office of being a pussy hound, even though he was married with two kids. Maybe he could smell Claudette's. After all, her pussy juice was smeared all over my face. The young attractive French woman had hooked Ted whether she liked it or not.

"I love it Mr. Ted. I've met so many interesting people," she responded with a nondescript answer.

She dropped her high heel on the floor and took her bare foot and brushed it against my erection. Yes, I was hard. The prospect of Ted discovering me and ending my career made my cock excited though my mind was terrified. Her light touch startled me and my head almost hit the top of the desk. I bit my lip instead of gasping. My lip was stinging and I could feel a trickle of blood running down my chin.

"So, Claudette, there's a great new French bistro in town. I wanted to check it out and was wondering if you'd be interested in going there for lunch?"

Ted's delivery was smooth and slick. It was clear he'd done this before, which was to hit on the hot women in the office.

Claudette was smoother in handling men like Ted. Keeping him interested but at arm's length.

"Oh Ted, I think I'm having lunch with Meghan today. Maybe some other time?"

I knew for a fact that Meghan wasn't having lunch with Claudette. Meghan was in regional sales meetings all that week. I was attending one of those meetings right after lunch.

Ted must have figured out that Claudette was just brushing him off and left him nowhere to go, so he bailed.

"Sure, sure . . . Claudette. You know you look very nice today," he said, no doubt disappointed in her rejection.

Claudette pushed her foot against my balls. I wanted to scream but couldn't. I was super tense and could feel the sweat forming on my armpits. Claudette's bare legs and the smell of her pussy didn't help things. I couldn't help but fidget to burn off my nervous energy. Ted must have sensed it.

"Are you OK?" he asked her.

"Of course," said Claudette. "Why wouldn't I be?"

I could hear Ted lean against Claudette's desk. The tip of his shoe was practically touching me.

"Don't forget about that lunch," he said in his usual smarmy way. What a fucking slimeball.

Claudette grabbed a handful of my thinning hair and pulled my head between her legs and into that sweet valley of all that is good. I got the hint. I buried my face in her crotch, trying to be quiet while I sampled her sweetness.

"You know, I like lunch on the early side," she said, squeezing her thighs together.

Ted chuckled. "I'll keep that in mind."

* * *

Miss Meghan was a driven woman, ambitious, aggressive and successful. Her commanding presence at the Weston presentation helped me close the biggest sale of the year. In her personal life she fell naturally into the role of a Domme, using me as her guinea pig before trying out whatever she did to me on her submissive girlfriend.

My performance the previous evening at Miss Lori's sex club convinced her I was worth keeping. Miss Meghan watched me have sex with her girlfriend Rose. I had the privilege of licking another man's cum off her curvaceous body. Big drooping tits coated with cum. Miss Meghan knew I'd do anything for her.

After the visit from Ted, I spent the next hour or so in the dark under Claudette's desk eating her pussy. My neck was getting sore and the muscles in my legs were cramping. I was sweating through my dress shirt. I could hear Claudette conversing on the phone in French so I couldn't understand a word she was saying, not that it mattered since I'd rather be eating her hairless pussy. She pushed back her desk chair and bent over so she was looking at me. The office lights made me squint, though I could still make out her cute face framed with curly blonde hair.

"Meghan told me she has a chore for you. Follow me."

* * *

Miss Meghan's office was a short walk from mine, but was an executive sized outside office with full privacy if the door was closed. Claudette waved me into the office and backed into the door with her butt until it closed with a loud click.

"Daveed, I've been instructed by Meghan to tell you that I'll be completing the sale documents with an important client. You'll be there as the new client relations manager. You are to do whatever the client asks, or you are to go back to your office now."

She waited and let what she said sink in.

Holy shit. Miss Meghan was offering me to a stranger. I had a real choice to make. Would I chicken out and leave? My out of body experiences over the past week gave me the backbone to stay.

"Tell me who the client is."

* * *

Claudette was sitting behind Miss Meghan's desk checking the messages on her phone and I was researching the client on my phone. We were meeting with Dr. Roxanne Martin, the head of Martin Industries, a research and development firm founded by her father. She graduated magna cum laude from Princeton and secured her doctorate from Cornell. She was a brilliant physicist and a sharp business woman. I was also to find out in Miss Meghan's office that Dr. Martin also excelled at drinking and anal sex. These facts were not discussed in her professional bio.

Roxanne was to stop by our office after a meeting in another part of town. We were to wait for her in Miss Meghan's office for her arrival. Claudette paid me no mind as sat there waiting, filing her nails as she chatted with a friend in French. Claudette was a beautiful young woman, a classic French blonde with a narrow face and nose, a long slender body and ample but not overly large breasts. I was still in awe of the fact that I had spent over an hour worshipping her pussy while she worked and talked on the phone.

My reverie was interrupted by a knock at the door.

Roxanne Martin opened the door, peeking her head in.

"Claudette?"

"Come in," Claudette said, standing up and greeting her guest with a handshake followed by a perfunctory hug.

I stood up as well in front of my guest chair. Roxanne came around and sat in the other guest chair, legs politely crossed at the ankles, not yet acknowledging my presence. I'm sure you've created a mental image of Roxanne. Let's see how it compares to reality. She was in her late 40's, a brunette with shoulder length hair streaked with gray. Her conservatively cut and expensive looking jacket and matching skirt couldn't hide her big tits and booty. She was on the shorter side but was wearing four-inch stiletto heels (my favorite) that accentuated her shapely calves. Her face was pleasing, though not a beauty queen, and the absence of the expected crow's feet and wrinkles on her flawless skin told me she had a top rate dermatologist. I loved woman in all shapes and sizes and I found her to be full figured and extremely sexy.

"I'd like to introduce you to your new client relations manager, David Elliott," Claudette said to Roxanne, extending her hand towards me.

Roxanne's eyes burned with intensity as she sized me up. I was sure she was thinking I was a dumpy middle-aged man and wondering why Miss Meghan had stuck her with me. I'd show her why.

Roxanne held out her right hand and I took it.

"So, you're David," she said as if she was familiar with me. "Meghan's told me all about you."

Roxanne had a slight smirk on her face when she said it. That had to mean she had a copy of the survey. Jesus fucking Christ. Miss Allison, and now Miss Meghan, had circulated my "confidential" confession of my absolutely darkest thoughts that I'd never intended to share with anyone and instead shared it with everyone they pleased. I guess important (and in this case attractive) clients of the firm made the list, which made me a company whore. I liked that. I liked that very much.

"I'm sure you've read my survey," I said.

"Every word of it," she said, confirming either my wet dreams or my worst fears.

She turned to face Claudette so I knew our "introduction" was over.

"So, you have the papers?" she asked Claudette, immediately shifting gears to business and ignoring me.

"Right here," said Claudette, sliding a stack of papers towards my latest Domme.

Roxanne stood up and leaned forward against the desk, leafing through the sheaf of papers. I got the chance to stare at Roxanne and focus on her curvy body. I was praying for the chance to ream her big ass and fondle her magnificent tits. Hopefully she couldn't read my mind because if she could she would have slapped me (or maybe not).

Roxanne went back into her purse to retrieve a pen, though she was apparently watching me out of the corner of her eye.

"You were staring at me," she said out of the side of her mouth.

"I'm sorry," I said, horrified and embarrassed.

She gave me a quick stare. "They'll be plenty to see later."

Oh yeah. She was condoning my wicked thoughts.

She went back to reviewing the stack of documents. She quickly flipped to the last page.

"Sign here?" she asked Claudette.

Claudette leaned over the desk to direct Roxanne to the bottom of the page.

"Uh huh, right there," she said pointing. They were both looking at the document. I was looking inside Claudette's blouse and admiring her firm young breasts.

Roxanne scribbled her signature on the page and pushed the stack of the documents back to Claudette.

"We done now?" Roxanne asked.

Claudette pulled the papers toward herself and reviewed the signature page. She smiled.

"We're all set," she said.

"Do you have what I asked you to bring?"

Claudette pulled a paper bag out of Miss Meghan's desk drawer and left it topside.

"It's here," she said.

Roxanne looked sternly at her watch. "It's 9:52. I've got a car waiting for me at 11:00 so that gives me a little over an hour."

Claudette nodded her head. "I'll be outside if you need me."

"I won't," said Roxanne. "Please leave us now."

Claudette retrieved her purse and left, closing the door behind her.

Roxanne looked at me. "You'll all mine, David. Meghan assigned me question 11. But first a drink."

Roxanne fished out a bottle of Jack Daniels from the bag Claudette left and snagged two cut crystal tumblers off the credenza. She poured two fingers for each of us. She gave me a glass and held out hers to toast.

"To the new client relations manager for Martin Industries -- David Elliott."

I clinked my glass against hers. Tennessee whiskey of which I was well acquainted. Sweet, unctuous and a satisfying burn. It went down easy. Roxanne had already finished hers and was pouring herself another.

"And you?" she asked, holding the bottle.

"I'm good," I said. I usually didn't drink before noon.

"Suit yourself," she said, slamming her second drink before removing her jacket. Her tits were practically popping out of her blouse (and so were my eyes).

"You're staring again," she said.

My eyes raised up to meet hers.

"Do you like my tits?" she asked me, cupping them in her hands to hold them up higher. I wanted to smother my face between them.

"I do."

"I saw you were staring at Claudette's as well. You a boob man?" she asked before draining her second glass of whiskey.

"I guess so."

"I'll bet you'd like to touch Claudette's. I would," she said, revealing her bisexual urges.

"She's pretty," I said.

Roxanne came up to me and bent my index finger back until it started to hurt.

Her eyes were boring into the back of my head. "Tell me the truth about Claudette. All of it."

"I've lusted after her from the moment I met her. Right before you showed up I was eating her pussy under her desk."

"Were you now?" she said.

"I was."

"That's better." She let go of my finger and poured herself a third drink. "Now tell me, do you think I'm pretty?"

I sighed with relief at her letting go of my finger. With the pain subsiding, I had to focus on her loaded question that was rarely asked and even more rarely answered. This was one of those rare times when the situation called for an answer.

"I do," I said, and not lying. "I prefer women who are . . . attractive and . . . uh . . . well endowed."

"Like me," she said.

"Like you," I confirmed.

She unbuttoned her blouse and lifted her right breast out of her bra. It hung over her bra, rounded and heavy, the size of a small cantaloupe, with a silver dollar sized areola and a fat dark brown nipple.

"Meghan said you'd do anything to suck on this. Is that true?"

"Without question," I quickly replied.

She reached under her skirt and tugged on her panties until they were at her ankles. She shrugged them off over her heels. She leaned against the desk and flipped up her skirt, exposing her ass to me. It was lily white, rounded and meaty. There were no ripples on it and with her legs slightly spread I could see the shadow of her inviting brown pucker. She looked over her shoulder to speak to me.

"Question 11 of your survey was about analingus. You said you wanted to try it. I'll give you a choice Mr. Client Relations Manager. Do you want my tits or ass first?"

It was an easy choice. "Your ass Miss Roxanne."

"Get busy," she said. "I've only got 57 more minutes." She spread her ass cheeks wider as she said it, showing me her gaping asshole.

What a vision of loveliness, beckoning to me.

I wet my finger and rimmed her asshole, smearing my saliva on it and making it wet and juicy. The guttural moan coming from Roxanne made my cock pulse. I circled her anus with my fingertip, making her pucker clench, which triggered yet another shiver up my spine.

It was heaven fingering her bum, having her moan and wiggle her ass so I could penetrate her deeper. I pried open her ring of muscle like a reluctant oyster, with two fingers. Her muscle contracted, pushing one finger on top of the other.

"Yes," she hissed. I could feel her anal ring had a vise grip on my fingers. I pushed hard against the tightened muscles, prying them apart, causing the air to escape her lungs.

"Oh fuck!" she screamed as my fingers slid in effortlessly to the webbing. Her asshole was tight, wet and hot. My tongue was drawn to it, touching the junction between her asshole and my fingers. I inserted the tip of my tongue in her asshole while my two fingers were still in it. I licked the smooth inner wall of her rectum and then outward to the stretched rippled skin covering the powerful muscles of her sphincter.

"You're a filthy slut," Roxanne said to me. "Meghan told me that and now I believe her."

I took her comment as a compliment. I aspired to be Miss Meghan's slut. I continued to happily lap at her asshole, though my perverted thoughts of course went to Roxanne's neglected tits. She must have read my mind. She unclasped her bra, freeing her massive breasts.

In her sexiest, gravelly voice, she said "Touch my tits."

I extended my arms so I could cup each of her big rounded globes while I tongue fucked her ass. She was rocking her ass up and down so my tongue could penetrate her as deeply as possible. She released a moan that was more animal than human.

"Yesssss. Fuck Mommy you slut."

Her fingers went down to her pussy, easing her aching want but not mine. I knew better than to touch myself without permission. Her legs started trembling.

"OhGodohGodohGod," she cried out. She was past the point of no return. Her anal ring was spasming around my tongue as she took one long deep breath, holding it.

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