bottoming in my boss's chair part two by sutreaux (ig @sutreaux)
Where part one left off:
"Rock on it. Show me how much you love it."
I did rock on it, fingering myself faster again, finding a really satisfying slide-hip roll-slide motion. I was so so close to coming like this, and your voice started tipping me over.
"You love being filled by me. You love being fucked at work. You love fucking yourself for me and showing me what you'll give me and--"
But then I about had a heart attack when the door handle rattled.
I like to think of myself as cool in a crisis. It's sometimes true, like putting out actual fires, or bandaging wounds, and thank goddess this time I was keeping it together.
I let myself pause to silently scream FUCK once before shoving the lube and the thinner, bright yellow dildo into my bag, and pushing it to the floor. I knew I didn't have time to pull the bigger dick out of my ass -- I'm not sure I could've let go of it if I'd tried. I did manage to arrange my skirt over my thighs, so at least whoever was coming in wouldn't see exactly what was going on -- assuming I could get away with not getting up from the chair. I heard the key sliding into the lock, turning over, and the latch clicking open.
It was not quite the last person I expected to see, but almost -- my kind of deadbeat but extremely hot boss, who almost never comes to work on Fridays, smirks at me in this sexy confident really annoying way, like she knows exactly how long I stare at her ass while she walks away, and smirks at men in particular in a way that makes it seem like she's humoring them. She was wearing the jeans that fit her so good that I get distracted in meetings, and a tank top showing off her smooth, strong, broad shoulders. I wasn't sure why she'd be in the office, on a Friday no less, but I was pretty sure I was fucked. Like, not just literally.
"Hi."
"Hey -- Carmen -- I'm sorry I'm in here, I needed a private spot to talk to my friend and I didn't think you'd need your office today and so I came in here to take the call because it's --"
"I really couldn't make myself care."
Classic Carmen. Kind of a dick, but in a hot way.
When she flipped the thumb lock on the door, I'm pretty sure my face became that meme of the blond lady trying to figure out math. But make it sexy.
"Come here."
My heart rate hadn't really returned to normal, though it was definitely lower than the initial spike, but all of a sudden I could hear my heart pounding in my ears. "What?"
She didn't even bother to respond.
I had to decide -- and fast -- if I was going to try to slide off the dick, but I couldn't risk the possibility of shitting on my boss's chair -- or somehow stealthily release the suction cup from the chair -- but that seemed, you know, very unlikely to work, and then what was I going to do, casually stroll over with six inches of dick in my ass?? I briefly considered just wheeling the chair, but the mental image nixed that plan.
"Now."
Fuck fuck fuck fuck fuck. I still had no idea how to get up when she added--
"And don't you dare let that dick slip out."
I don't know if it was just the fact that I suddenly had the answer to my conundrum, or that I was deep in submission, or that it was my hot boss saying it, or maybe that I still wasn't far off from my orgasm and wanted to keep the dildo deep in my ass, but I didn't question it. I slipped a fingertip under the base of the dildo to un-stick it from the chair, then reached around with my other hand to hold it inside me as I stood up. I didn't need to worry about it slipping out -- the motion pulled the dildo deeper into me, and I gasped and doubled over, catching myself with my palms on the desk. When I looked up again, Carmen was smirking at me, even more annoyingly than usual.
"On second thought, it doesn't really seem like you'd make it. Stay there, hands on the desk." She started moving towards me, around the desk. I admit that I may have shifted my stance a bit, leaning forward onto my palms, bending arching my back and lifting my ass. She pushed the chair out of the way and I could feel her behind me. "Holy hell. This is so hot."
I felt her fingers on my hips, first gentle then tightening as I moaned and arched even more. I had long fantasized about seducing my boss, mostly to keep myself awake during staff meetings, and this exact position -- me bent over her desk -- had been a key theme.
"Ah shit, wait. Jess, hang on, look at me." I tensed a little bit, unsure and feeling very vulnerable, and curved my neck and torso to be able to look at her. "I really really want this, want you. And, it's important to me that you know that you can stop at any point, say no to anything, and it won't affect your job at all or how I treat you at work. This isn't legal cover bullshit, but for real. Yeah?"
It was ... honestly the most genuine and kind thing she'd ever said to me, and I would've been taken aback if I hadn't been so impatient to come.
"Yes, great, thank you Carmen. I'm 100% in, I consent, yes, I'll sign whatever you want saying please fuck me now boss, just like get on with it."
"Ahaha I love that." By now she was lightly trailing her fingers over my ass and I could barely listen to what she was saying. "I don't need you to sign anything." The fingers of each of her hands stroked from the top of my ass crack, down towards my cunt, stopping right above the sensitive skin under the curve of my ass, then back up. "I'm pretty sure if anyone complained to HR, it should be me." On the next downstroke, I stretched onto my tiptoes, trying to push my cunt towards her fingers. "You are the one fucking yourself in the ass in my office, after all." Her fingers didn't take the bait, slipped back up my ass, just along the crest of my crack, teasing and sensitizing. "And now trying to fuck yourself on my fingers too. So I'm not too worried about the legal part." The next stroke she pressed in, scratching my tender skin with her short fingernails, making me inhale sharply through my teeth. "Plus, I'm pretty sure AJ would have my back on this one."
Her fingers were suddenly gone and I whipped my head around to see Carmen picking up my phone from where I'd forgotten about it on her desk chair.
"Wait what the fuck?"
"Hush. Be patient, slut." She accented her condescending, controlling, and very arousing words by tapping the backs of her fingers against the base of the dick in my ass, making me cry out and collapse onto the desk. "Well done, AJ. You've earned the reward I promised you."
AJ's voice was suddenly different from how I'd ever heard it before -- quieter, meeker, and more carefully pronounced. "Thank you Sir. I'm so grateful that you let me serve you."
"AJ, you may keep watching if you'd like."
"Yes Sir, please Sir, I do want to keep watching."
Carmen turned back to me, as things were clicking very slowly in my brain. "Hold this, slut." She slid the phone into my hand that had been flat on the desktop, and I instinctually held it upright, facing Carmen and my ass. "Very good, slut. And keep it like that. You won't like what happens if I have to keep reminding you." With that, she slid her flat hand down over my ass crack, briefly rocking the dick in and out of me, then finding my cunt and clit with her fingers.
"Fuck Carmen yes please finally."
She had a finger stationary to one side of my clit, another finger rubbing my clit into and against the still one. With her palm cupped over my cunt, I could feel my heat and wetness pressed back against all my most sensitive parts.
"AJ."
"Sir?"
I kept almost forgetting about AJ, lost in the sensation, but somehow muscle memory had the phone propped up well. As she said their name, my eyes refocused and I saw how hungry AJ looked, so intent and a little flushed, and still, as if holding themself really carefully. They looked so hot like this, so similar from how I'd seen them so many times before, just before sliding their dick or fingers or empty beer bottle deep into me, but also so different, somehow visibly submissive.
"You didn't teach her any manners?"
"I know you love a brat, Sir." Carmen kept stroking me as she laughed deeply. Her fingers on my clit, plus the way they talking about me -- with such calculating judgment, and as if I wasn't there, or like I was just some fuck toy there for their games -- and of course the dick seated so deliciously and a little overwhelmingly in my ass, and I came out of the blue, so sudden and ground-shaking. The whole work shook. Or, more accurately, all of me shook, thrashed on the desk. Jess and AJ were both silent, I'd like to think awed, and I was anything but, yelling and gasping and almost crying through the orgasm that took all of us by surprise.
Almost as soon as I started coming, Carmen's fingers slid easily into my cunt, and my cunt grabbed onto them, clenching and releasing but never letting go. With her fingers inside me, her palm pressed against the base of the dick, I felt so solid, as if she was stabilizing the core of me, even while everything else was still having tremors. She told me how my orgasm felt around her fingers, and flexed her fingers together and apart in time with my rhythm, pushing back against even my strongest clenches.
My cunt shook and gushed into Carmen's palm -- I know because when the power of my orgasm pushed the dick out of my ass, Carmen slowly but firmly pressed it back into me, and my own cum eased its slide back into me, even as my muscles shook around it. "Uh uh, we're not done with this yet. Hold onto it a little while longer, slut." I moaned in response, almost like a song, rising and falling in pitch and volume as I shook, adjusted, and began to relax around it.
She held me there, tenderly and insistently, as my orgasm started to wane. I say started to wane, because she didn't let me come down very far before more actively playing in my cunt.
I was coming down, but still way sensitive, too sensitive, and needed another minute to recover. When I was almost cogent again, I said, "Damn fuck wow, okay, hold on. Pause." Carmen's fingers stilled in me and I took a breath. "Okay, gosh. Thank you. You don't need to stop, just don't start escalating again for like, one second."
Carmen grinned at me, but her fingers didn't start moving again. "I love a bossy bottom. You're going to be so especially delightful to break in. Just tell me when you need to stop."