Hello there. This is my first post this this subreddit, and one of my older stories. Any critiques or criticism are welcomed.
I have the best job in the world. No, really, I do. I know what you’re thinking. ‘I’m a CEO, and I make millions!’ or, ‘I’m a doctor, and I save lives!’. That may be, but my job’s still better. What’s my job? I’m an executive personal assistant. No, wait, I know it doesn't sound like the best, but I’ll prove it to you. Let me take you through an average day at my job.
Most days begin with me waking up at six o’clock, doing a quick 15-minute workout, and hopping into the shower. From there, I whip up a smoothie for breakfast, get dressed in my suit and tie, and out the door of my spartan apartment by seven, so I can catch the seven forty bus to work.
I know what you’re thinking: ‘Apartment, bus, bah! Rich lifestyle for someone with the “best job in the world”’. And it’s true, lots of other jobs earn more, and it’d be nice to have a car, or a yard, or a 401k worth more than a shoe box, but I’d live on the street to keep this job.
My commute isn't too bad, I usually show up at my building by about eight thirty, and at my office by eight forty-five. Well, not technically my office, I share it with my boss. I usually give a nice greeting to Lucy, my boss’s non-executive personal assistant, on my way in, and she gives a friendly ‘hi’ back.
When I enter my office, by boss, Mrs Jameson, is always there. Always. I don’t think Suzette Jameson has ever missed a day or even been late (apparently, being a Vice President of Marketing doesn't have as many perks as you would think). She’s a striking woman. She stands tall, even without heels, has long brunette hair that’s nearly always in a tight bun, and she carries a little more weight than you see on movie stars, (but most of it is in pleasant places). She has a firm demeanor, nearly always business, and has a knack for being as direct-to-the-point as possible without being rude.
Every day, when I come in, she gives a quick, “Hello there John,” or “How was your weekend?” on Mondays. Then, I hang up my suit jacket on the hat rack she keeps in her office and crawl under her large desk. She then let’s me know what my duties are for the day. Most days, begins with “My feet could use some relief”. That’s my cue to begin my job, the best job in the world.
I take off her heels, and start to gently massage her feet. I rub my fingers over her sheer nylons, digging gently into the ball of her foot, slowly working my way down to the heel. After a while of this, she lets me know to move forward either with a quick “Be sure to get the ankles” or simply by kicking her feet further towards me.
Then, I move my massage slowly up her ankles and calves, marveling at the feel of the strong muscles of her legs and the feel of the flesh on top of it. Never, in all my ministrations, does she look down at me or pause in her work. I can always hear her writing, shuffling papers, or talking on the phone.
It’s never too long after I start on the calves that she indicates, either through words or actions, to move up. Massaging her thick thighs is a beautiful experience, and I often wonder if I’m the only who delights in it. Mrs Jameson wears a wedding ring, but in my six months here I've never had the nerve to ask her about Mr Jameson. She’s never volunteered anything, but she doesn't really talk to me outside of work.
It varies, but usually I’m under her desk no more than an hour-and a half before Mrs Jameson gives me the go ahead. Usually, it’s by casually reaching down, placing her hand on the back of my head, and pulling me towards the prize. The absolute best part of my day. She spreads her legs, pulls up her skirt, and then I see it, her beautiful cunt on display. A light dusting of brown pubic hair covers her meaty outer lips, and I always see her pleasure glistening on her inner thighs. She used to wear panties, but that became too much of a bother. I kind of miss it though, even though she rarely wore anything but plain white panties. It was like unwrapping a Christmas present.
It’s hard to restrain myself, but I do. Rather than dive into her cunt, I lick all around her lips, keeping her mildly aroused, but not so distracted as to be unable to do her work. I’m aroused as well, but I have little opportunity to do anything about it. Once, she caught me pleasuring myself as I licked her, and she let me know plainly that if she caught me ‘distracted’ again, she’d find a new executive assistant.
By eleven, I’m usually lapping at her hood, and around the edges of her entrance. I know every millimeter of her, I could sketch that woman’s cunt from memory, and tell you which areas are the most sensitive, which I should avoid, and which I should attack directly when she tells me that she needs to cum.
I usually give her three to four orgasms during the course of the day, mostly with my tongue, but occasionally with my fingers, and sometimes with both at the same time. It doesn’t happen terribly often, but every now and again, she let’s me fuck her.
It’s the best. The last time I fucked her was last Thursday. It was about one forty-five, and she was getting close to another orgasm. Suddenly, she backed up from the chair told me to stand up. I did so, grateful for the chance to stretch my body. Then she told me in plain terms what she wanted. “I’m going to bend over the desk now,” she said, with the same tone she uses to tell the intern how many creams with her coffee, “and I want you to fuck me hard and fast. Don’t be gentle, I need to cum soon. I want to be fully refreshed for my two-thirty”.
No further prompting needed, I pulled a condom from my wallet, unzipped my pants, and wrapped myself up. I looked over to the desk, and I reveled in the sight of her, bent over, skirt above her waist, and with an aroused yet slightly bored look on her face. Even in that position, she was the boss, and I was her living toy, the perk of being the boss.
Not that I minded in the slightest. I positioned myself at her entrance, and slowly put my dick into place. Once I got myself situated, I thrust in firmly. She was wet and warm after all my ministrations, and it was easy to get myself into a rhythm. I fucked and pounded into her over and over. It was pleasure beyond pleasure. This time she moaned a little bit, letting me know that she enjoyed it, but usually she’s all business, even when my cock’s hilt deep in her cunt.
It isn't long at all, several dozen thrusts, until I felt her rhythmically squeeze my dick, orgasming on me. That’s all I ccould take, and I came soon afterwards, filling the condom with my sperm.
Then we stood there for a minute, panting and enjoying the afterglow, and for a moment, I forgot I was at work. But the moment soon passed, and Mrs Jameson stood up as I pulled out of her. I excused myself to her personal bathroom to dispose of the condom, and piss, and she followed up soon afterwards for her ablutions. Then, I went under her desk as usual, and gave her a nice hidden foot massage while she talked with her boss.
But most days I don’t get to fuck her, and I have to pleasure myself at home, with only thoughts of my day to inspire me. My job could be better. I could earn more, the commute could be shorter, I could fuck my boss more often, but I still contend that my job is the best job in the world. What do you think? Is your job better?
Source: reddit.com/r/eroticliterature/comments/2uc687/the_best_job