The idea to seduce my boss first came up on a dreary Thursday evening. It wasn't so much dreary in that the weather was crap, but more that we were trapped in the office slogging through spreadsheets and project plans when we would much rather be at home drinking or...well, doing anything other than what we were doing.
"We," of course, means myself, plus my coworker Katie. We were both heavily involved in a couple of the same projects together; her as Project Manager and me in more of a technical support role. We also had the same boss, a woman named Colleen, who had a knack for making our professional lives pretty hellish. When you first meet her, she seems nice enough...a decent boss, easy to get along with...but as pressure on her mounted to get projects out the door faster and with fewer resources, her professional ambitions took over and she drove her teams ever harder.
I suppose I should describe the three of us, since this is a sexual story after all. We're all "normal" sorts...no Pitts or Anistons in this crowd...but definitely reasonably good-looking people.
Katie is about 5'5" or so, in her early 30s, with long loosely curly blondish hair. She's a bit mousey looking, with thin features, grey eyes, and glasses. Definitely cute though. Her breasts are right for her frame, probably around a small B-cup or so. She also has very delicate hands, which I've always enjoyed watching as she types. I imagine she does some visual arts in her free time. Katie tends to dress very conservatively, tending toward comfort over style with long flowy skirts and loose-fitting tops. All up to date styles, but nothing fancy.
Colleen is of "fuller" build, but by no means overweight. She is around 5'9", with darker brown curly hair, and dark brown eyes. The workout regimen she recently started had really done the job, taking her from "office worker" physique, to a much more "fit" look. Her newly flattened tummy definitely accentuated her D-cup breasts, particularly with some of the tighter sweaters she prefers. Colleen generally sticks to fashionable business casual, with the very occasional conservative dress. She seems to consistently manage to choose pants that are particularly form-fitting, especially when sitting down, which is always distracting for me in meetings.
Finally, me. I'm a pretty normal looking guy, average build, average physique (could stand to lose a few pounds), and about 5'9". I have dark brown hair, blue eyes, and wear glasses when I run out of contacts. I'm pretty average in just about every dimension (yep, down there too). I know, not too exciting, but it's the truth.
Back to the dreary Thursday evening... Katie and I, while not "close," do get along quite well personally and professionally. I think I might be a little bit more enegergetic than the people she's used to hanging out with, but it doesn't seem to bother her too much. One thing we definitely have in common though, is a mutual distaste and frustration with our boss (and, as I would later discover, a mutual taste for crazy sex). On this particular evening, as the day wore on, our productivity began to drop off and our conversation once again turned to our frustrations about Colleen.
I'll spare you the boring back and forth, but the defining moment was Katie muttering, "she probably just needs to get fucked."
"What?!" I said, completely taken aback at something I never would have expected to hear come out of Katie's mouth.
Katie blushed and looked down demurely. "Sorry...I just...I dunno. She just strikes me as someone who probably doesn't have much of a love life, that's all. Maybe she'd lighten up a little if she'd take some time off and got was getting a little love every now and then."
I chuckled and thought about it for a second. "Yeah, she probably would. We should pay someone to seduce her or something."
"Might be tough to find someone," Katie said, grinning. "I mean, I suppose she's pretty attractive, but she's probably a tough nut to crack. You'd probably have to...pry...a bit, you know?"
"Yeah, I suppose so. I mean, shit, I'd probably do it myself if I didn't think it would get me fired," I said.
Katie looked surprised. "Funny," she said, "I was about to say the same thing."
It was my turn to be really surprised, but at that moment, Colleen walked in and our thoughts turned immediately back to the project...
The next day, Katie stopped by my cube. I spun around in my chair to face her as she was bending down to whisper something and our faces collided. We both pulled away quickly in surprise after my lips and two day stubble brushed against her delicate pale cheek, leaving a small red mark.
"Oh! Hi...sorry about that!" I said, slightly embarrassed.
"No it's OK. You need to shave though!"
"So what's up? Reporting engine broken again?"
Katie leaned in closer and whispered, "actually, I was thinking about our conversation last night..."
I was pretty sure I knew what she was referring to, but I decided to play dumb to see where she was going with it.
"...I think we should do it. I think we could pull it off."
I raised an eyebrow slightly. "You're not talking about re-working the database structure, are you?"
She touched my arm lightly, and the additional unexpected contact felt like a tiny electric shock. When did Katie get so intimate? "You know exactly what I'm talking about, and yes I'm serious. I think we should try it. We both hate this place...what do we have to lose?"
"You've obviously lost it," I said. "Which one of us do you propose...um...do it?"
"Both of us. At the same time."
I could tell by the look on her face that she was serious. Possibly off her rocker, but definitely not kidding. I contemplated what she'd said and as ridiculous as it sounded, frankly, the thought really turned me on. I shifted around a bit to hide my rapidly growing hard on. Before Katie had a chance to notice and probably tease me about it, she looked at her watch, "Crap! I'm late for my call…gotta go!"
I spent the weekend replaying the conversation with Katie in my head. She HAD to be kidding…just fucking with me. Weird sense of humor on that one, I thought. Eventually I managed to push it out of my head, but not before putting the imagery to other uses first.
Tuesday morning, I had gotten my head on straight for the most part. After a few hours of fielding calls, an instant message from Katie popped up, asking me to stop by her office. Assuming it was project-related, I hustled down the hall and poked my head through the door.
"What's up?" I asked.
Katie motioned toward the empty chair sitting next to her desk. "Have a seat, gotta tell you something."
I sat down, and Katie quickly leaned in close. "I've got it all figured out, don't say anything…just listen."
Over the next five minutes, Katie outlined her plan in great (and slightly rapid) detail, as I sat dumbfounded. Once again, I had to shift around in the chair to hide my arousal, but before it could get too out of control, Katie's office mates returned from their coffee run, so we quickly changed the subject and pretended to wrap up our conversation.
The rest of the day proceeded quietly, and I did my best to keep my mind on my work, until I passed Katie in the hall as she was collecting some documents from the communal printer. I stopped next to her.
"Hey, so…one question…" I started.
Katie turned to face me, smiling slyly. "Yeah, what is it?"
"You and I, we've never… I mean…" I'm so awkward sometimes.
Katie smiled wider and stepped close to me, bringing her lips a fraction of an inch from my ear.
"…Been intimate?" she whispered hotly.
Still in shock from her sudden change in demeanor, all I could do was nod slightly.
"Well, then I guess that will just make it a little more interesting," she muttered.
Katie quickly placed a soft, warm kiss on the corner of my mouth while lightly tracing my jawline with one finger, then turned back to her print job.
Wednesday and Thursday passed uneventfully, if not somewhat slowly. Every time I passed Katie in the hall, or sat in a meeting with her, she acted as if nothing was afoot. I found her nonchalance somewhat disconcerting, and started to wonder if maybe the whole thing was off. Friday morning, however, I dressed up as planned and headed off to the office, with butterflies aplenty whirling around in my stomach.
I ran into Katie almost immediately, and she looked fantastic. She wore a nice calf-length skirt with a subdued floral print that bordered on translucent in the right light. On top she wore a neutral blouse with a plunging neckline that was a bit more form-fitting than what she normally wore and which drew attention to the pale skin between her breasts.
I, on the other hand, with my limited wardrobe choices, tried to pick the most flattering dress pants and shirt that I owned, and of course slapped on a tie as well. I certainly didn't look like I'd just popped off the pages of GQ, but based on some of the comments I received from Katie and others in the office, the outfit had the intended effect. Also, I'd lightly sprayed some cologne, bought especially for the occasion, that Katie had somehow discovered was Colleen's favorite thing to smell on a man.
Faced with questions about why we were so dressed up (relatively speaking), we simply used a joint presentation as an excuse, which was basically true, since we were presenting to a group of director-level members of the project. In truth, it was all part of the plan.
The idea was that we would schedule a last-minute meeting with Colleen, right at the end of the day. The office usually cleared out pretty early on Fridays, with many people rushing off to spend time with family, and many of the rest joining up for happy hour at one of the many nearby downtown bars. Then, once everyone was gone, Katie would take the initiative (less threatening) and get the ball rolling.
As the day wore on, my anxiety grew, as did my increasingly-difficult-to-hide erections. Between the two, I was pretty sure I was going to pop one way or the other.
Finally, it was go time.
Katie and I showed up in Colleen's spacious office as scheduled, and began to set up using the wall-mounted flat screen to present. Per Katie's instructions, I had tweaked some of the graphics properties on my laptop, which caused some extremely annoying artifacts and flickering. After about five minutes, Colleen sighed and said, "oh for crying out loud, just bring your damn laptop over here and let's get this done."
Katie looked at me and nodded slightly. I disconnected the computer, and set it in front of Colleen. Katie and I both stood on either side of Colleen's chair, within pointing distance of the screen. Re-situated, I continued to speak to hold Colleen's attention. Meanwhile Katie fished a small but very powerful vibrator out of her purse which sat to the side, out of Colleen's field of view. Taking advantage of Colleen's attention being focused on my PowerPoint slides, Katie surreptitiously passed the small, pink, egg-shaped vibe to me, which I covered in the palm of my hand.
The next few moments would be the most critical, defining whether we'd be fired...or worse. The plan was to throw Colleen way off-balance, and take advantage of that moment to make our move. See, the thing about Colleen is she tended to get really riled up about people "wasting her potentially billable time" if anyone ever seemed to be less than prepared in a meeting or presentation. She's even come close to firing someone over a few facts missing from an important presentation. Yes, she can be that much of a bitch. So, with that in mind, Katie purposely deleted a key slide, and left out a few points we knew she wanted to hear about...and it worked.
"Wait a sec here guys," Colleen said, the irritation clear in her voice. "You've left out exactly the information I wanted to get out of this stupid meeting. I mean, you keep me late on a Friday, and you don't even make it worth my while?! You make the effort to get all dressed up, but you can't even make the goddamn TV work right? I expected more from you two!"
I mumbled a half-assed apology, and Katie stood there looking mortified (on purpose), and after a moment, a single tear traced a wet path down her cheek (on purpose). Colleen softened...barely.
"Look, don't cry about this...you just need to get your shit together."
"But I...we...worked so hard to get this ready for you," Katie sobbed.
Continuing the ruse, Katie leaned over and slammed the laptop shut and started to walk away with it. Colleen roughly grabbed the computer out of Katie's hands. "We're not done here," she growled.
Katie stopped in her tracks, wiped away the forced tears, and shoved Colleen's rolling chair backward, which I grabbed and forced to lean backwards (always a fun trick if someone isn't expecting it). She then practically pounced on Colleen, straddling her lap and holding Colleen's face firmly. "You're right, we're not," Katie said, her voice low and husky.
"What the f-...mmmff," was all Colleen managed to squeak out, before Katie kissed her deeply. Between being thrown literally off-balance and having one of her employees sitting on her lap forcing her tongue in her mouth, Colleen had no idea what to do. Rather than fight, she just went limp.
So far so good - that was my cue to move in. I flipped the switch on the vibrator, and it came to life in my hand. It was a surprisingly powerful vibrator, given its size. With Colleen still in shock and physically occupied, I reached around from behind her and pressed the vibrating egg firmly against her crotch. Colleen's eyes flew open and she squealed as she dropped the laptop in surprise.
Rather than pushing either of us away, Colleen grabbed the arms of her chair. The only thing running through MY mind was "oh fuck oh fuck oh fuck…can't believe this is happening." I have no idea what was happening inside Colleen's mind, but after a few moments, she seemed to relax a bit, which included her thigh muscles which had immediately clamped down on my hand. Colleen moaned quietly into Katie's mouth and I felt her start to move her hips just slightly to grind against the vibrator in my hand.
But, the initial shock was short lived; Colleen quickly pushed Katie away, and blocked the vibrator with one hand.
"What…the fuck are you two doing?" she asked incredulously.
"I'm gonna level with you, boss, you're a fucking cunt to everyone in this office, and as much as I'd like to slap you every time I see you…" Katie paused for a moment, and lightly caressed Colleen's flushed cheek, "…I think the better way to deal with this little problem is to fuck you…every way that we can think of."
Colleen just stared back blankly, at a complete loss for how to respond. Katie leaned forward and planted a small wet kiss on the corner of Colleen's mouth. Colleen didn't pull away.
A few tense moments passed before anyone said anything. Finally, Colleen broke the silence.
"OK," she whispered.
Katie gently grasped Colleen's hand, brought it to her mouth, and slowly swirled her tongue around Colleen's ring and middle fingers. "Touch me," she said quietly.
Tentatively, Colleen reached forward and lifted Katie's skirt, exposing her red lacy panties. I watched, basically dumbfounded, as Colleen slowly pulled the panties downward and slipped her fingers through the folds of Katie's pussy. "Fuck me, dammit," Katie practically growled, as a guttural moan escaped her lips when Colleen complied by sliding her two saliva-slicked fingers into Katie's cunt.
