My Boss's Other Secretary Jerks Me Off

My Boss was getting more and more confident.

Not that he ever lacked it, but after last night the insane domination and fucking...

Today when I got Cindy up and made her come in early round the back door to go into his office, getting set up, Mister Johnson called her in to walk by me, shut the door and then begin moaning as he fucked her the hour before everybody was about to come in. I was panicking as the loud slurping sounds and then spanks sounded, and then the plapping and moaning of surprise as his big cock filled her up again, slapping into her and making her moan long needy whines, sometimes quick **** ones as he bullied my girlfriend's pussy with his big black cock.

He was so confident, this time he didn't even wait until I was home before sending me the email of him fucking my girlfriend in his office.

He sent it right there to my work email where anybody behind me could have seen the thumbnail if I opened it at the wrong time.

It said the same as the home ones, that it's a video of my girlfriend and that I've been ordered to jerk off to it and cum with evidence that I've cum to them fucking before the end of the day or I'm fired. Which means I'm gonna have to do the usual easiest ways, to go into the bathroom or some abandoned 13th floor room and watch it with the sound on while filming myself jerking off to it. Then send to him. He didn't tell me to cum in the toilet, but given he might assume it, it'd be safer to. Goddammit.

After railing my girlfriend and sending her out for me to quickly click off of my emails and her to fix her hair back up in a ponytail and brush down her clothes, doing up her top button, walking past giving a kiss on the cheek to get to her desk, he wasn't done.

After I went to the bathroom and filmed myself jacking off to the video and cumming in a toilet stall, sending it to him, he had another task.

Go to room 49 to do your jerking off today, cuck. There'll be someone there from 1pm to assist you. You will take another video of yourself jacking off to my prowess and cumming. You will include them in the video or your employment shall be terminated effective immediately, as of 5pm today.

The abandoned conference room next to his office. It had tape stuck to it that it used to be used as a closet for storing a bunch of paper files when transitioning to online, so I never went in there. Weird.

I was... excited.

I opened the door and saw her right there.

Through light cigarette smoke and a small orange light, an endlessly seductive image of an 80s-looking dream.

She was sat with one leg crossed over up on my end of the white conference table, seeming disinterested in everything and slightly annoyed to be there. Short brown hair only long enough to her frame her chin. A tight, clinging dark brown dress that dipped into to her thighs and cupped her breasts with a heart shaped cleavage and curving her ass on the table. And a small silver watch on her wrist she was currently looking at. She took a drag of the cigarette and blew it my way.

This was one of our many secretaries. The secretary Veronica who had often visited my boss in his office. She was undoubtedly the woman who my Boss had kept the clothes of, to later dress my girlfriend to fuck her in.

"You're late." She stated calmly, uncaring in a way, just an observation.

"Y- yeah." I laughed nervously. "You're um, the help?"

She nodded.

I considered maybe this was some way of a fuck you but maybe ending the torment, glancing into his room to see why he had wanted this.

At a thought of his texts that maybe I could report him to HR, I tapped my pocket and looked in, only for my heart to sink even further as I realised why he'd set this particular day up in the first place:

You might think why would I go through all the trouble, surely he wouldn't fire me over something that could get him super fired and in jail.

But... well...

"AHHHH! YESSS! Tye! Tye! BIG FUCKING- NIGGER DICK- AH-!"

He's currently fucking Dana from HR in his office. A busty, big-assed white redhead with glasses who normally has her long hair up in a tight bun, where she often makes braids so elaborate.

"AHH! AHH! DADDY!"

SPANK

He growled and pulled her hair, fucking harder. "FUCK YOU SAY TO ME, BITCH? FORGETTIN' YOUR MANNERS NAH?"

"NNnnniiaaaaAAAHHH! S- SORRY DADDY! I MEANT- N- N- NIGGER DADDY! OH MY GOD I CAN'T MY- MY PUSSYYYY- P- PLEASE CUM INSIDE ME THIS TIME DADDY! PLEASE KNOCK ME UP MISTER NIGGER DADDY!"

I found that they had an arrangement. That it wasn't just she wanted sex or he did and it was hot being HR and fucking the Boss against the rules, or even that he was hot or had a big dick.

I watched.

What I learned through the dirty talk was that she had had boyfriends before (he talked about her exes getting her to moan and nod that he was bigger than all of them, with a bigger dick and thicker cum than all of them) and that at some point she had begun to cheat on one with him because she desperately wanted a child, and either he was an asshole and she wanted to take it out on the Boss's cock, that she just thought about getting back against him by the thought of having a black baby to tell him the biggest fuck you before breaking up with him.

Or that somewhere, breaking up with that ex, with another man and still cheating, that she just got off on the kink of fucking a black man while dating white men, continually dating new ones when the old ones found out and left, until this most recent one wanted a baby again, so she talked to my boss with his hand on her hair about her white man trying to knock her up and begging the boss for a black baby instead.

This led to him ripping her white button-up shirt apart, tearing a hole in the middle of her black tights, making her gasp and moan both times, before making her beg for his big black dick and thicker 'nigger' cum, and sucking him off loudly before getting him spanking her, finally pulling her bun undone, putting his hand in her hair to mess it up and make it fall down, the look of it over her eye and falling around as he fucked her, this wild sexy horny woman who was so prim and proper getting hair pulled and face shown moaning as he slammed into her from behind, the fucking and body hard enough to move the table as he fucked while she desperately clung on to it kneeling on it and her heel falling off as he fucked.

"Holy- f- fuck..." I said as we watched.

Veronica blew smoke and laughed with no emotion. "Uh-huh. He's good alright. Yeah I got told to help you cum to a video? A video of your girlfriend getting fucked by Mister Johnson?"

She looked me up and down, and I faltered. I nodded.

She grunted lightly, before patting the table beside her to sit. I walked over and leaned against it. She looked down at my pants and nodded a head up. "So you got the video on your phone or something?"

I nodded, pulling it out.

"I uh- this is kinda fucked up but uh-"

"AHH! AHH! AHH! AHH! TH- THANK YOU N- NIGGER DADDY!"

"I don't really have a choice..." I got the phone and went to video, ready to record. "So you jack me off to it?"

She stared at me for a moment, took a drag and blew it in my face. She considered something.

"I didn't say if he wanted to see you cum or not. I just said he wanted proof that you would jerk off on command. In front of me." She tilts her head, her short hair falling to the side. She pouts brown lipstick. "So... you're into this, huh?"

I gulp. I don't feel like I'm super seducing her right now, but she's giving me some signals. She's looking at my cock and I can't tell if she's about to bully me or not.

"I- I have to. For my girlfriend's job."

"Okay." She snorted, before taking another drag of cigarette as she watched my girlfriend get railed. She sighed out smoke, smirking to me. "Just for me... tell me the truth? Are you into this? You can quit, you know."

I frown at her, motioning to the room. "Why did you do this just now."

She shrugged, shaking her head. "That's different. I don't have a choice, I'm a woman. He's a man. You're supposed to be a man and say no. This is weird. You're hard."

The sound of the woman being fucked grated my ears as I tried to focus. He was more hindering than helping at this point. I glared at Veronica a little.

She wasn't phased. "Do you like being talked down to?"

I thought a moment. Then nodded.

She smoked. She blew. "So. How much are you going to pay me to talk down to you? Just between you and me. Boss doesn't need to know..."

"Wh- what about my girlfriend."

She looked at me like I was stupid. She grinned. She slipped her shirt open, the tit jiggling down to rest low under her cleavage showing a perfect pink ghost nipple. "Aww how cute... I don't think she's the one you're worried will find out, do you, sweetie?"

I grunted. But I couldn't stifle how turned on I was by her tits and the situation. Her callous demeanour.

She raised an arched thin black brow. "So you're into like... cucking, right? A cuckold, is that it?"

I wince, but then reluctantly nod.

"A cuck?" She repeats.

That hurts.

But I nod. She pouts. She rubs her tit and looks a little disgusted at me. "That's kinda pathetic."

My cock twitches. I nod. "Sorry..."

She sighs. She looks in the room at the fucking and her lip just slightly, bites. She shrugs. "Hmm, well from the little I know about it, that means you'll basically do anything, right? Hmmm..." She considers for a while, then puts the cigarette out in the ashtray. "Tell me how much you'll pay me."

"Uh..." I gulp. No playing coy, she clearly knows what she's talking about. I put my hands to my bulge, legs twitching. I shrug. "I- I dunno. I never done this before. 5 bucks a minute?" I blurt it out. Shit maybe that's too much.

She shakes her head. "No."

She slowly stands and steps towards me. Her ass really was perfectly shaped and the sitting didn't help it hid it. She swayed towards me and jigged slightly, staring up at me.

"If you're willing to go that far you'll go much, much farther. You're going to pay me more or I'm telling the whole office. And the Boss will just fire you. Something tells me you don't want that." She bites her lip and smirks at me.

She flicks her phone, "What's your cashapp?"

I have it, but only for a couple payments before. I give her mine, and I get a message. A request.

For 500 bucks.

"Fuckfuckfuckfuckfuckfuckfuckfuck..." My head falls back. I run a hand through my hair. I sigh.

"So that's a yes?" She stares at me with no empathy at all. I feel myself gulp.

I nod. "Fuck fuck fuck fuck fuck yes. Yes. I- can't do much more..."

"No?"

She looks at me. She smiles. She takes a hand and moves it to my cock, stroking up and down the bulge. She stares at me. "No?"

"N- no..."

She strokes slowly. "No?"

I gasp and begin getting harder. The sounds of the woman getting fucked. I start panicking. Getting hot. "Oh- oh no..."

She smiles at me and flares eyes. "'Oh no'!" She mocks. "I'm going to pay one thousand bucks to this whore just for jacking me off!"

I glare at her and she pulls her hands off. "Or I could...?"

"NO! W- wait- FUCK."

I nod and she, quicker than ever moves to clack short but perfectly trimmed nails against the phone, and quicker than anything the request is through.

"Okay. Good cucky. Go on then."

I hesitate.

She moves to stroke me off and stares at me with that smile again. I growl.

I send it and feel myself with a raging hard-on, it flips up as I pull down my pants exposing my small white cock to my Boss's side piece.

She looks at her phone and it makes a bing, she smiles more and looks at me.

She looks at my cock, pulling it out and snorts at it again, before taking it in a black-nailed hand and wiggling it a little. "Ahhh now it all makes sense. Not that I ever thought you'd have a big one but, no offense, you just never exactly had the biggest dick energy Timmy. You know that, right cucky?"

"I... agh!"

She strokes and moves around behind me to take the hand other to my chin, moving to make me look at it. The woman getting fucked on her knees on the desk. My Boss. Her body beginning to hold still as she holds breath to stop orgasming. My Boss spanking her. Her titties falling out of the ripped shirt and tight bra and my Boss pulling on her hair and her finally cumming on his dick.

Veronica moves to my ear and gently kisses, tugging on it with lips to whisper. "Sssssssshhhhh just enjoy it... you're a lil cucky right? So enjoy it! Yah!"

Yah...

I get harder and she begins stroking around up and down and up and down.

"You don't mind if you cum in your itty bitty panties, right? If I don't have to touch it with my hand? I mean he didn't technically say I had to do that so... is that okay? You're alright with that right? If I just... stroke it like this until you blow?"

I grabbed the desk in front and buckled. She smiled and laughed, finally with some emotion as my Boss pulled out of Dana the HR rep and pulled her back by the hair, spanked her and made her begin sucking his cock on her knees loudly and sloppily.

Veronica gently bit my ear and blew into it. "Just relax... there's a good boy now. Just give in. It's alright. You're okay with send me another 500 right?"

I stiffened. I do not. Not like paying women to jack me off. I don't. I don't.

I gripped my phone. I moved to it and got it up again, tapping in the number.

She smiled and kissed my cheek. "Good boy. Send? And I might make you cum."

I moved a finger to send and she-

"Wait!" Stopped me. "Sssssshhhh sh sh sh sh sh sh sh" She said. "I've got a better idea."

She slowly traced a finger down over my hand, then tapped the phone, and deleted 5, and put in 6.

$600.

I groaned and she sped up. She spoke. "Would you like me to make you cum? If you want to cum say seven hundred."

I roared and she made a mocking moan, tutting and then letting go of my cock completely.

"Or I could just-"

I tapped in 700.

She moved around and knelt and smiled up at me, stroking my bulge before blinking sweetly and then teasing a hand down at the top of my pants.

"Eight hundred? I swear I'll make you cum... so good..."

I pressed in eight hundred.

"And?" I said.

She looked at it and then me. She smiled. "Oh I'm not a monster. Eight hundred dollars for jacking you off I won't argue for more baby, be a good boy and send."

I sent.

She pulled my pants down and boxers and pulled my cock out. She smiled at it and pouted slightly. She looked at my phone and showed the price to me. "Eight hundred. Wow."

She wrapped her hand around the cock and stroked harder.

I buckled getting lose, pre-cumming.

She stroked my cock so so fast, I gripped the desk and she looked into my eyes. "Be a good boy and cum. Cum out your eight hundred bucks all over my face there's a good boy now. Sssssshhhhh sssshhhhhh our little secret. Yah?"

I came. I throbbed and came, spurting out thin ropes slapping against her face and dripping, sliding down to make her gasp and smile. She stroked and then moved to kiss the tip, sucking it clean and then moved a finger to slide some cum to eat it. "Thanks for the eight hundred bucks, cucky. I'm really really happy about our arrangement. I'll totally meet up again, if you ever want me again, just give me a call. Of course... you might need to save up a little more for that..."

PLAPPLAPPLAPPLAPPLAPPLAPPLAPPLAP

My Boss made our HR rep moan as he fucked her with her legs up her body naked with her shirt ripped open fucking into her over and over about to cum inside, roaring a cumload as I sent the video to him.

He looked at his phone. He looked up. He smiled at the glass near me and winked.

He spanked our HR rep and pulled out, sloppy cum falling dripping from her pussy as she moaned and gripped moving legs to gently try and tease up and down his back to get him to go again.