A couple weeks ago, I found myself on a rather interesting business trip. The long and short of it is that I ended up walking in...accidentally, mind you...on one of my coworkers masturbating. But, a little background before I get to the good stuff.
My name is Will, and my aforementioned coworker is Kelli. I'm 33, in the neighborhood of five foot nine, perfectly average looking, with my only distinguishing characteristics being particularly vivid blue eyes and a propensity for waistcoats. Kelli is probably exactly what you're picturing when you imagine someone else's attractive officemate: late-30-something, leads an active lifestyle (which of course leads to things such as toned calves and the like), natural blonde, very pleasant, very professional, and wielding a fantastic pair of breasts - not too big, not too small - that manage to fill out a nice sweater just right.
Oh, and an interesting, “Minnesota mom” accent, even though she’s not from Minnesota, nor is she a mom.
We both work for a typical technology company as typical office drones. I wouldn't call us 'friends', but we work in the same team and end up helping each other out on various projects all the time.
Anyway, back to the aforementioned business trip. We flew out to Chicago together to visit a particularly troublesome client for a few days. Not fun at all. Quite stressful, actually.
We were in the middle of our second day there, and as expected, it was not going well. After a few hours of meetings, the group eventually split up for lunch, and I hung back in the conference room for a few minutes so I could fire off a few emails. A trip to the restroom was most definitely in order before lunch.
I wandered down the hall toward the little alcove that housed a drinking fountain and the boys and girls rooms. It was a small office, so they were single-person type things. At that particular moment, I was responding to a text while walking, and headed toward the door marked 'MEN'. What I was actually seeing, however, was '-MEN'...as in '(WO)MEN', due to the way the walls were angled. Naturally, without double checking the sign, I waltzed right in.
I was not ready for what I walked in on and the next fifteen seconds felt like fifteen minutes. Kelli was there, perched on the toilet tank, head thrown back, skirt hiked up to her waist, thighs splayed wide, with one hand pulling her panties aside and the other furiously rubbing her snatch. I caught just a glimpse of neatly trimmed blonde pubic hair and light pink lips before her thighs clamped shut, leaving her hands temporarily trapped.
Our eyes locked. "I...uh...sorry...I thought..." I stammered, trying to point at the sign I'd misread.
Kelli's face turned a deep shade of crimson - a sexy, embarrassed deer in headlights. Maybe a little mad, but mostly mortified.
"Out!" she hissed, chest still heaving. I backed away quickly and shut the door. I heard shuffling, then the lock clicked behind me.
The rest of the day was pretty much downhill from there. I couldn't think clearly due to visions of zero-tolerance sexual harassment policies danced through my head. And visions of Kelli having her way with herself...can’t forget those. Kelli hardly said a word, and was completely silent during the cab ride back to the hotel. We parted ways in the lobby, presumably for the rest of the evening.
(I will admit though, I definitely blew my load into a shitty hotel tissue within ten minutes of getting back to my room.)
When I went down for dinner in the hotel restaurant, I didn't expect to see Kelli, but there she was, waving me over to the small table she’d staked out.
"Hi," I said, cautiously.
We made sparse small talk about the meeting until the waiter took our drink orders.
I decided to take the initiative. "So, about that elephant in the room..." I said. She blushed again and grimaced.
"Wait, just hear me out for a minute. First, I'm really
sorry about that. I wasn't paying attention and I was absolutely not intending to invade your privacy like that. I spent the rest of the day with waking nightmares about getting a call from HR..."
"Oh no, hang on," she said. "This whole thing is awkward, but I'm not going to complain to HR, so please don't worry about that. If anything, I figured you'd report me.
Sigh of relief. "OK...wow, thank you. No. I have no reason to report you. It stays between us. Seriously."
Kelli visibly relaxed. "I can certainly live with a little embarrassment between just you and I," she said. "Stuff happens."
"Can I ask one question though?" I said. "Just a curiosity thing. You don't have to answer, but I'll drop the subject after."
Kelli cracked a little smile for the first time that day. "Sure, I suppose so. Shoot."
"I was just wondering...why right then? I mean, why not wait until you got back to your room or something?"
"Ah, that’s simple. Stress relief. Sometimes...you know...is the only thing that works for me. I can’t just gobble a Xanax or something, otherwise I’ll be passed out under the conference table. I do generally remember to lock the darn door though!" She giggled.
We hung out in the restaurant for awhile longer, just bullshitting and drinking. At a lull in the conversation, I noticed the time, and was just about to announce my intention to hit the hay.
Kelli took a deep breath. "Look, I know I should really keep this to myself, but... Well, honestly, you walking in on me like that...it...kinda turned me on...like, a lot."
" I asked, dumbfounded.
"Yeah, I...um..." she took a small sip from her drink, "I actually finished after you left. I couldn't help it. I had...still have... no idea why it affected me so much, but it did. Heck, I almost asked you to stay and wait until I..." her voice dropped to a whisper. "Until I orgasmed."
I was speechless. Incredibly turned on and thankful for the tablecloth, but still speechless.
Kelli finished the last of her glass of courage. "So...oh geez, I know I shouldn’t ask this, but... Would you be willing to help me, you know, recreate that? It's all I've been able to think about since then. Besides, you've pretty much seen everything anyway, right?" Another shy grin.
I knew I should politely decline. I knew I shouldn't risk my job. I knew my girlfriend would probably
be pissed (although I planned to keep my hands to myself). But at that point, my little brain tackled my big brain, and the only word that passed my lips was, "Sure."
Kelli continued to grin nervously, clearly far outside her comfort zone. "OK, I'm in 802. Come up in about ten minutes or so. Here's my extra keycard."
"Oh, one more thing. Just for fun, can you act annoyed? Like you just want me to hurry up and get it over with? I know that sounds weird...it’s hard to explain. Might as well go for broke though."
"Sure," I said again. "I’m a crummy actor, but I can probably manage that."
Eleven minutes passed. I couldn't remember a time I'd had so many butterflies bouncing around in my stomach. Further, I hadn't needed to hide an erection while standing up since high school gym class.
I stepped out of the elevator on the eighth floor, practically right in front of her room, slipped the card into the reader, took a deep breath, and walked in.
The room smelled of beauty products and shampoo. I could see Kelli's skirt and blouse tossed over the back of a chair. A pair of baby blue, lace panties lay on the floor at the foot of her bed. I heard a mixture of rustling blankets and heavy breathing.
Kelli came into view as I rounded the corner. She sat on her bed with the comforter pulled up to her hips. I could tell she was naked from the waist down, and white tank top was the only thing covering her from the waist up. Her nipples seemed to want to stab through the thin fabric and her unencumbered breasts jiggled with the movement of her right hand which worked enthusiastically between her legs.
Her movements slowed as I approached. A deep blush graced her makeup-free cheeks. "Oh, sorry Will," she said between breaths.
After a brief moment of confusion, I remembered the last thing she'd told me downstairs. I'm not much for role playing, but our shared corporate culture made it feel natural and I pretty quickly slipped into the 'part'.
"Uh...hi, er... I mean, dammit Kelli, we're running late for our meeting and you're still in your room playing
with yourself? What...what the fuck is this all about?"
Kelli's cheeks darkened a shade or two. "Don't swear at me, Will," she said. For a moment, I thought I'd crossed some line, but then I realized she'd picked up the pace under the comforter. More inspiration hit me out of nowhere.
"Kelli, I'll swear if I damn well please. We've got five hours of meetings ahead of us, and you're too busy...what, rubbing your clit? Fingering yourself?"
"A little of both," she said meekly.
"How many fingers are you using?"
I rolled my eyes like I thought she had no idea what she was doing. "Better use two then. You really need to hurry the hell up. I don't have all day to wait for you to get yourself off."
I crossed my arms, shot her a judgemental glare, and tried to look bored. Her eyes remained closed, and when they opened briefly, they seemed to be fixated on the bulge under my belt.
I let out an exasperated sigh. "Quit staring at my cock, we need to get going." I walked over and picked up her panties and skirt, making sure to waft the lacy fabric under my nose. I was rewarded with the musky, heady scent of feminine arousal. I tossed her clothes onto the bed. "Get your fucking fingers out of your pussy, put your clothes on, and let's go. I'm not getting fired because you can't control your urges."
"Please can I finish first? I'm so close, I just need like, maybe a minute or two. Please?" Her breath rasped between words, and there was a vigorous desperation to her movements. “I just really need to cum.”
"I think you're sandbagging. Running out the clock while whining about how you just need a 'little longer' to make yourself cum. Get out from under the covers so I can confirm you know what the fuck you're doing."
Kelli's cheeks darkened yet another shade, but there were barely a couple seconds of hesitation before she threw back the comforter and raised herself into a kneeling position. She didn't miss a beat, and with the comforter out of the way, I could see the moisture coating the insides of her thighs and hear the wet sounds her lips made as they grasped at the invading digits.
"Kelli. Look at me." I used the cheesy, two fingers pointing at my eyes motion. She complied, fighting the urge to let her eyes roll backward. "If you don't get this done, I'm leaving without you and you can fend for yourself when all hell breaks loose. Just get it done, or give it up. I don't care.”
Kelli became frantic. Beads of sweat glistened on her forehead. She yanked the tank top up and began to maul her breasts with her free hand, alternating between kneading them and tugging at her engorged nipples.
I thought back to the times my boss tried to make friendly "suggestions" as to how I should do something. Usually he was wrong, but sometimes... "Have you tried playing with your ass at all, Kelli? Have you considered that this might be more efficient if you just put forth some effort back there?"
"I would, but...I...I have more than enough to do with just two hands."
I shook my head in disapproval and mumbled something about deadbeat, lazy employees while smoothing my tie and rolling up my sleeves. Without being asked, Kelli fell forward onto her elbows. Her hips and asscheeks undulated almost pleadingly in my face.
"Alright, I'll help you out, but we're going to have a serious conversation about this when we get back to the office," I said. Complimentary hotel lotion sat unopened on the nightstand. I broke the seal and squeezed a dollop onto her puckered asshole. The absurdity of the whole thing occurred to me, but I didn't care. I was having too much fun.
I rubbed a fingertip around her ring, probing just slightly, which elicited a throaty moan. "This is it, you're out of time. If you can't get the job done with my
help, you can probably go ahead and kiss your job goodbye."
"I’m really sorry Will," she panted. "Oh my god, I'm so close. Please help me finish?" she pleaded, looking over her shoulder at me.
I pushed a bit harder, past the barrier to her most intimate area. Her muscles squeezed and clenched at my finger. Kelli moaned again and pushed back against me, forcing my finger even deeper. Using her hip for leverage, I began to fuck her ass slowly with my finger.
"I'm ready now," she breathed a minute later.
"Good, it's about time. Just fucking cum already so we can get going."
Kelli buried her face in the comforter to suppress a scream. Her entire body tensed as she continued to masturbate at a frenzied pace. After a few moments, the tension released, and she flopped face down on the bed, almost every inch of her body twitching and legs flailing. Her hips bounced as she ground her clit against the heel of her hand, riding out the last waves of her orgasm.
When it was all over, I withdrew my finger slowly, and Kelli rolled to her side. She was no longer blushing, but modestly pulled her shirt back down and moved a pillow in front of her crotch. A shiver coursed through her body and a satisfied groan escaped her lips.
"Thank you. That was...amazing," she said. "I'd work for you any day. Now, hurry up and get a promotion so you can be my boss for real."
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