Bottoming in my Boss' Chair Chapter 1
bottoming in my boss’s chair
part one
by sutreaux
Content tags: domination, nasty talk, office sex, toys
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It took us almost a year and a half before we started fucking around in public — in earnest, at least. It’s not like we were entirely chaste before then, but it was just a few stolen moments here and there, until you laid in my bed that night and told me how much you get turned on being felt up on a street corner.
That one conversation, and many more tender and hot and sometimes risky moments brought us to the moment that you directed me into my boss’s office. It’s a small organization, so I’d taken to noticing a little more distinctly when everyone else was out on a call or at lunch or whatever my coworkers do with their time. In moments like those, I’d find my way into a bathroom stall with my phone. (Gross, I know… Whatever.)
It started with texting — nasty words back and forth, petting myself over my pants, or at least over my unders, or at least mostly over my unders. It escalated to voice memos, recording the breaths, gasps, groans of my orgasm, quiet but distinct. Pictures next (over Signal of course); sometimes your gravelly voice directive and insistent over the line; and of course eventually FaceTime, both of us silent as I exposed myself to you. I had some of my best orgasms in that bathroom stall.
But none compared to that one time, the Friday morning before a three-day weekend, when by 11:30 I hadn’t seen anyone in the office, and I found my mind drifting towards the restroom. You’d been provoking me about it the night before. We both knew my work would be a ghost town the next day, and you prodded me about what I would do for you next, what additional level of risk and sluttiness I would give you with so much time to play. That’s all to say, my cunt was already throbbing the minute I walked in the front door, but I made myself wait until 11:30 so I could be more sure than not even Dylan (who always came in late) would stroll in. And I was waiting for you to tell me what to do.
Finally -- your first text: “Hungry, slut? I think it’s about time for your lunch break, eh?”
Food was the last thing on my mind. “Well I just ate my breakfast sandwich…”
“I imagine a slut like you is hungry for something other than food”
Then, a picture of your hand cupped over the (silicone) bulge in your jeans.
“Yes goddamnit you know what I’m hungry for.”
The first instruction was already something new in this game, to go into my boss’s office. The workplace was pretty chill, and trusting, so I wasn’t too worried about being in there, though I had no idea what you had in store for me. Then to sit at her desk — again, not the hugest deal, I could’ve been trying to find something.
My boss had one of those cheap plywood desks with two drawers on the side that don’t reach all the way to the floor, and underneath the drawers I found my overnight bag, and in it an old t-shirt (so I knew you planned for this to get messy), lube (at least some of the source of the expected mess), and two dildos, a pretty short and thin yellow one and the thicker, longer purple one that you like to slide into me and watch my eyes go wide, my teeth pulling at my bottom lip.
I had no fucking clue how you got the bag there, but goddamn I was grateful.
“Suction the purple dick onto the top of the desk, directly in front of you. You’re going to suck it for me, and you’re going to take a picture for me, cocksucker.”
“Use the timer”
“Prop the phone so I can see your cheeks bulging around the cock on your tongue”
Luckily I started salivating as soon as I read it, because that dick’s girth required a wet mouth. And patience. It only took me like 15 seconds to get the dick and the phone setup, but then a minute or more to get enough of the dick into my mouth and throat that you’d be pleased with me, and maybe even reward me.
I sucked it even after sending you a really excellent picture, continuing to hum around it and work it back behind my tongue. I was glad I hadn’t stopped after taking the pic, cuz my phone twanged with the incoming video call, and the first thing you saw was another half-inch of the dick sliding past my lips.
“Goddamn you suck cock so good, baby. I wish I could tangle my fingers in your hair, pull you down onto my dick, hold you there and thrust gently, nudging the back of your throat while you figure out how to breathe around me.”
I’ve always been so turned on by your words, your voice, your dirty fucking mind. My cunt pulsed harder, and I started squeezing my thighs together and subtly rubbing myself against my boss’s seat.
With my mouth still on the dick, you told me what to do next. I’m sure my eyes went wide with fear, or excitement, but I still nodded when you asked me if I understood, and if I agreed. I’m not sure if I was stalling or savoring, but I slowly, devotedly lifted my mouth off that dick that suddenly seemed wider and longer than it had in my mouth, detached it from the tabletop, and placed it — head pointing directly up — behind me on the chair. Your eyes flashed as you watched me stand up, lift the skirt of my dress, and pull my underpants down to my knees. I’m not sure you even noticed the pleading look in my eyes.
You had told me to put what suddenly seemed like a monster of a cock in my ass. That dildo is at least three inches longer and a finger’s width wider than anything else that had been there, which was limited to a couple of your fingers and one training plug. Thank goddess for water-based lube, because as slutty and messy as I am, I’m also kind of neurotic, and my second or maybe third thought -- after oh fuck and oh yes -- was how I’d need to wipe off the chair after.
I’d never been fucked (by myself or anyone else) ass-first before. I had always started with old fashioned vag sex, getting wet and hot, taking so much inside me but not quite enough, aching to be stretched and filled, before finally letting my ass open for you. I wanted to savor the new experience, but also a little pressed for time, so I couldn’t quite get the pace right. I was using one hand to guide the dildo, the other palm flat on the chair to support me. I took a few breaths and then started out a little faster than I intended, gasping a little “aaahaaa--” then had to pause to breathe and reset and savor.
“Fuck slow down lover, it’s not a race. Take your time for me. Show me, tell me how it feels.”
I hadn’t forgotten you were there exactly, but definitely had been focused on what I was doing, so I started narrating as best I could while breathing through the penetration. “Oh god baby, this dick is so thick, and stretching my ass open. It’s just the head in so far. I don’t know if I can take the whole thing.”
“That’s okay baby, there’s no rush. I think you can take the whole thing. Make me proud, slut. Open that ass for me.” You always were good at mixing humiliating names and tender affirmations to make me feel so safe and so horny. It gave me the motivation to slide down another half-inch, groaning and throwing my head back.
Once I had the dick settled a little deeper, I didn’t need my hand to guide it anymore, and could start fingering my clit and cunt. The dick in my ass had mostly hurt so far, in a good way -- but believe me when I say I am really good at fingering myself, and suddenly everything sped up. The slow and steady slide was over, no more narrating, just pushing down a little too far, gasping on my way back up a little, fucking myself in the ass on camera for you.
I heard my name, and noticed your voice was stern, suddenly. I realized I’d missed you trying to get my attention for a minute, and you were pissed.
“I know you’re a slut, but jesus babe… Good sluts listen and mind. Bad sluts… Well--”
I hadn’t stopped rubbing my clit, just slowed down, and my ass had made it most of the way to the chair. “Ahhh fuck. Bad sluts get punished.”
“And?”
I can’t imagine the words were particularly understandable, but I got them out through my gasps -- “And they’d better be fucking grateful.”
“Yes, exactly. You’re doing better already slut.”
“Thank you, fuck this is so good. I never knew--”
“I don’t really care what you knew or not. I knew.” I shut up, getting hotter as you told me off. “Put the phone closer. I want to see exactly what you’re giving me.”
I didn’t want to give up my fingers on my clit, but also knew I’d earn a hell of a punishment if I didn’t let you see the last inch of that dick slide inside me, so I kept myself propped on my palm and used the slippery fingers of my other hand to grab my phone and position it on the seat, propped a little bit for the perfect angle.
“Fuck yes. Very good slut. Now lower yourself the rest of the way, so so so slowly.”
It was agonizing and incredible, holding myself back from slamming down onto the rest of the dick, just barely moving, holding my breath and hearing you groan and unzip your pants. When I was finally there, I let out a deep sigh, as if the breath came all the way from my pelvis up through my stomach, chest, throat, and lips. I could relax a little for a moment.
But not for long -- “Rock on it. Show me how much you love it.”
I did rock on it, fingering 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.