Administrative Assistance [MF]

I have a complicated (but thoroughly enjoyable) relationship at home. We mainly have (still, after all of these years) a lot of sex, but I travel a week or two per quarter for work, as I have for the past 4 years, and we enjoy having sex with other people during my times away. We don’t play together, and we’re both bisexual, and like many others here have already written, we get hot when we hear stories from our partner — and that greatly enhances our already enjoyable sex life. We only play when I travel for work (my partner is retired now), and we have two impossible rules. First, neither of us will have drunken sex with other people. Second, we both set something up, but individually, before anybody gets play time. In other words, if she has setup a play date, but I haven’t, then her play date is off, and vice versa. This means that we’ve cancelled many, many times. Sorry, but we are those people at times.

I wouldn’t label us as swingers, as having an open relationship, or as being pansexual. I would label us as opportunists, and with our arrangement we have met other sex partners as we are able. She likes to play with other women. I like to play with a M-F couple, and far less frequently with other women. Again, we never play together, and almost certainly never will. It’s a situation that we both very much enjoy, so we’ve gone with it for the past four years.

For my partner’s contribution to each of our extracurricular activities, she’ll find women on craigslist, or chat them up in the mall or wherever. She’s excellent at identifying prospective partners, and is way better at it than I. For my contribution, I meet a lot of prospective partners when I travel to work in Vegas, and have also had luck at meeting people while staying at hotels near casinos in New England.

This time around I’d been sent to a well-known, so-called “weird” city on the west coast of the U.S. I was to have a four day in-office training, and then I’d take a red eye back home late Thursday night. I had been to this office before: twice. As a sale rep in my recent professional life, I’d come to know practically everybody who worked in a sales or business capacity, or in an administrative/assistant capacity with my current company. That’s when I’d first met her. Maura (made up name) was our administrative assistant, all all good (professional) things stemmed from her desk. She was friendly, pretty, always dressed very well, smelled amazing, great legs, nice rack, wide butt, was shorter than average, had the cutest / most awkward laugh, and had this ethnic flair that I couldn’t quite put my finger on, but really liked (I have a similar ethnic flare, but few dig it). On top of it, Maura frequently would head home during midday to change her clothes into something more revealing, but at the same time still appropriate for a professional environment. Almost always she would return with a shorter skirt, or higher heels, or with a couple of extra buttons unbuttoned. I say this all as someone who’d found her interesting out of the gate, but not as someone who had imagined having sex with her. I was easily 10 years older than her, and plus she is/was a co-worker. Little did I know…

Maura is a master planner. Any time you needed someone to plan some kind of corporate event, she would be on it, and it would always be great. This time was no exception. She knew that a bunch of us were coming in from out of town, so she’d planned a couple of events the second night we were in the office. Unfortunately, I’d worked with a bunch of single people, so the vast majority of people bailed after the second event. Maura looked very disappointed at the second event of our night, and that left her, me, and a co-worker of mine to sort it out. She’d mentioned a local and popular dive bar, and he was game to go, so we piled into an Uber, and headed out that way.

At the dive bar, he was nowhere to be found, and she didn’t know anyone there, either, so I kept our chat light, and we were riffing on one another’s off-colored remarks about food, what we were drinking, and people who walked by the bar outside. We were laughing uncontrollably, and she frequently fessed up that she had to pee “because of me”, so that she wouldn’t have to pee on the floor. I told her that if she had to pee on the floor, then I would just whip it out, and we could have a “pee-union” right there at the bar. She found that more hilarious than any other thing I had said all night, and ran to pee again.

That’s when my other co-worker reappeared to check in. He had been trying to score some drugs from the outdoor area, and had felt that while Maura had looked “more than good enough to fuck that night,” he was in it for the magic 8-ball, and that if I wasn’t going to try and fuck her that night, then he would at some other time — because on that night his mission was to score some drugs, Uber back to his hotel room, and then to consume them. I’d found this conversation to be odd, because I had never mentioned wanting to fuck her before, and it was weird that he’d chosen drugs over sex, but I suppose his remark had made sense on some level. He wasn’t the first guy who’d found Maura to be pretty sexy, it had been rumored that she was into having a roll in the hay, and how she’d definitely been into letting it hang out a little bit after she’d been out and had a few.

That night was no exception. When she’d returned from her most recent trip to the ladies room, she had taken off her sweater, and was carrying it under her arm. It was apparent that her above-the-knee black dress showed more than a bit of cleavage. I hadn’t noticed this in the office before, but then again, that probably hadn’t been her MO at that time. She was wearing this black, velvet choker around her neck, and her 4 or 5″ black stiletto heels (I didn’t have my measuring tape with me on that day, so I don’t know whether they were 4 or 5″ for sure) matched her black dress to a tee. It was that exact moment that I decided I was going to go with the flow, and perhaps I would end up in her bed later that night, assuming that we were both sober enough, oh, and of course if she was willing. I shot a quick text to my partner that read, simply, “green light”, and that was it. I received a thumb’s up emoji in return.

Maura and I decided to have one more drink, but she’d insisted that we take a shot of her choosing. I don’t know what the shot was, but it was awful. After I downed the shot, I felt pretty awful. I suspect she was feeling the same way, and we kind of leaned on each other in a drunken state while we waited for the Uber. I’d told my co-worker that I was bailing, but he’d kind of nodded and ignored me, so Maura and I were on our own. She’d asked if I was hungry, and I was trying to get the stink out of my mouth, and to make the gross and drunken feeling go away, so I had agreed that food was probably the best course at the point of the night. The Uber took us to another dive, a diner, and we settled into a booth in a deserted corner of the place. We ordered a bunch of food, we were still laughing, and it was clear that we had both sobered up substantially after a couple of hours at the diner.

That is when I was having an internal dialog about how to close out the night. So, in sales, you get a lot of tough guys, a lot of aggression from guys who refuse to let a deal die, whether it be monetary or physical. It goes with the territory, but my approach was different, but yet with surprisingly identical results. I keep people laughing, make a strong value proposition for a product, give them a price that I know they can’t refuse, and make the deal. I forget what Maura was talking about at that point, and she was still laughing a lot, which was weird because I had been doing really nothing but nodding, but eventually I determined that my best pitch to close out the evening was “we need to get you home.” To my surprise, she agreed, and I had said that I could ask the Uber driver to go to a second destination, or that I would just ask for another Uber.

On the Uber back to her place, she told the driver to stop ahead of our destination by a few blocks. We both got out, and she headed into a bodega. I waited outside on the sidewalk. Two bags of groceries later she emerged from the market. I insisted that I carry both bags, and we walked 3 blocks to her apartment. When we’d reached the door of her apartment, I assured her that helping her get the groceries inside, and make sure she got upstairs were my immediate priorities, and she gave in. Thinking back, it’s true that she’d protested pretty much not at all.

I helped her get the groceries to her apartment, and set them on her (tiny) kitchen counter of her (obscenely tiny) apartment. She apologized that the place was a mess, laughed nervously again, and unloaded the groceries after having told me to take a seat (the only place to sit that wasn’t occupied with loads of clothes and other clutter was her bed), so I took a seat at the corner of her bed as she put stuff away. She asked me if I’d wanted a beer, and I’d obliged. When she was done unpacking her groceries, she’d asked me if I’d wanted a cigarette — and while it’s true that I quit smoking years ago, I did enjoy taking offered cigarettes when away on business — I said that I’d have one if she was going to. She motioned me into the kitchen and cracked a window, and we stood arm to arm smoking one of those Virginia Slim 100s type of contraptions while trying to vent our smoke away from her cooking and sleeping areas. We were mostly successful.

I had drunk most of my beer at that point, she had had of hers. I was trying to think of a subtle way for me to stay with her a bit longer.

As we continued to blow smoke out her window while standing arm to arm, I simply said, “oh, and by the way, I really like your perfume. It’s very subtle, but it smells awesome.” She laughed nervously again, and stomped out her cigarette in the ashtray. I felt that I had blown it at that point, but I was surprised when she’d offered to show me her selection of perfumes that resided on a shelf in the main room next to her bed. She’d patted her bed, and I sat down on it once again.

Selection after selection she would do a quick spray on her forearm and then would have me put my nose to her forearm. She asked me what I’d thought of each perfume, and I would weigh in, and then she would tell me where she’d gotten the perfume, and what her mood was when she’d put some perfume on at some point during the midday or after hours. At that point she hadn’t crossed any lines, and I was still trying to figure out if one of us was trying harder to seduce the other, but still she kept prodding me as to what my favorite of her perfumes was, and what my partner’s favorite perfume of hers’ would be. All the while she’d kept intense eye contact with me, and her precious and nervous laugh kept coming out.

I’d crossed my legs earlier so she would (hopefully) not see my hard on, and after the perfume show, she’d asked if I’d wanted another beer, and I declined. She’d asked if I’d wanted another smoke or some food, and I declined. A look of disappointment crossed her face, and it was palpable. She asked if there was anything I needed, or if I just wanted to take off.

I tented my fingers and rested my chin on them.

I looked her directly in the eyes, smiled, and said, “I think you should take off your clothes.”

To my surprise, she seemed to have been caught off guard by my remark, and she just stood there with her intense eye contact, still laughing nervously.

I untented my fingers, and rubbed my hands together while maintaining eye contact with her.

“Take off your clothes.”

She asked for help with the top of her zipper then stood before me as she finished unzipping, and then she let her dress fall to the floor. I tapped her rump with my hand and got her to turn for me. Her black thong was as great as everything she’d put on display for me on that night. I got up off the bed, we embraced, and tongued while my hands probed her nipples and ass. Then I pushed her on the bed, her ass up, and ripped her panties off. Well, OK, they didn’t rip completely, but one side ripped, and that was more than enough for me to have easy access to her pussy… and her ass.

To my delight, she was completely bare down there: all of it. I forced her face down into the bed, and held her hands behind her back. She didn’t tell me not to, so I proceeded. I buried my face in her crotch and went to town. She tasted awesome, and she was only the second woman I’d been with (the other being my partner) who got so wet that it was just oozing out of her.

She stopped me (I assume that she came because she was loud enough that I’d thought the cops were going to show up at any minute), and I asked her if she was okay. She said that she was ready to be fucked, and after wriggling away from my grasp, unbuckled my belt, and pulled my pants down. I grabbed a condom, and put it on. She told me that she’d wanted it bare, and while I really wanted to feel her that way, I wasn’t ready to go bare with her … yet. She pouted a little, but then told me that she wanted to be on top since “it had been a while”.

I finished undressing, then laid on my back on her bed. She, wearing nothing but her heels still, got on top of me, and put me in her, but slowly, a little bit at a time. I’m not all that big, so that was a surprise, but then again, what a lady wants…

As we fucked, she kept reaching behind her ass, and trying to push my condom up and off. Now, I have a huge fetish for barebacking, but rarely do it with people I don’t know, and for the obvious reasons. Plus, we needed to check STD/whatever tests and that stuff, and I really wanted to consult with my partner if bareback would be OK with Maura if everything had checked out. Still, the cat and mouse game with the condom was a fun one, and while I’m normally a cum first, cum fast, get hard again, keep it going type of guy, the risk factor here kept my body in check, and we just kept fucking. And fucking. After I’d finished the first time, she’d kept trying to seduce me without a condom, but each time I’d just put another condom on and we’d be at it again.

I woke up with her in my arms, and my spent condom falling off my penis, and we spent the next few days either in her apartment or in my hotel room fucking each other every which way. Eventually, after consulting with my partner, and having a few more conversations with Maura, barebacking became the norm, and, as it was her idea, she was my mistress when I was in town for business. Sometimes we’d end up in bed with another woman, but frequently we would end up in bed with another man, which was fine by me.

More to cum, as some would say, but I remain glad to this day to have such great administrative assistance.

Source: reddit.com/r/gonewildstories/comments/6qqyqn/administrative_assistance_mf

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