Sybil's Got a Spanking New Job - Cover

Sybil's Got a Spanking New Job

by Crankshaft Cafe

Copyright© 2025 by Crankshaft Cafe

Erotica Sex Story: Sybil doesn’t think much of her new boss’s threats to spank her right there in the office - she plans to call his bluff.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Reluctant   Fiction   Cuckold   Slut Wife   Spanking   .

“Sybil.”

“Earl.”

“What in hell’s wrong with your ass?”

“Earl, you do know our insurance does not cover acts of God or stupid questions, don’t you?”

“Okay. How about—hey, babe, what in hell’s wrong with your ass?”

“It’s the same ass you see every night—if you’re lucky.”

“Not looking like that.”

“Like what?”

“You’re covered in big, red welts. I saw them a few days ago and thought you were wearing your thong too tight.”

“You saying my ass makes it look like I’m gaining weight?”

“Nononono! But there’s all them welts and bruises. I didn’t say anything when I first saw them. But there’s more kept showing up, until you’re dang near purple.”

“Ouch! Shit, Earl! Don’t touch ‘em.”

“What’s causing that?”

“Maybe from leaning against a hot grill on one of them cars out at the dealership. Nothing to get all bent out of shape about.”

“I thought you took an inside job.”

“I did.”

“Then why’ve they got you working outside on the lot dressed in a short skirt and heels?”

“Could be the manager thought it might bring in a few more customers if I—you know—hung out there like one of them models draped over cars at the auto show.”

“That explains the skimpy outfits.”

“It’s just my work clothes.”

“Back when you were dancing for tips, maybe, but that short skirt, low cut blouse, and sparkly bra showing off your nips ain’t anything like office wear.”

“Earl, what would you know about office wear? You ever work in an office?”

“No. But I’ve seen the girls that do, and they don’t dress like that.”

“A shit lot you know.”

And—the only thing that might—might—cause you to blister up like that is the grill on a sixty-six Cadillac Deville that’s been in the sun too long. I know for a fact there’s no sixty-six Cadillac anywhere on that lot.”

“Okay, Sherlock, it’s not some hot car grill on the lot, but before you get all high and mighty on me, just know—none of it’s my fault.”

“What’s not your fault?”

“The manager spanking my bare ass for every little thing.”

“Spankings? Like in school? Like the principal used to give you?”

“These ain’t nothing like old man Dodge used to give us girls. This is more like daddy used to give, but daddy never used anything but his hand.”

“How in hell’s he get away with that!”

“Now just keep your shirt on. He gets away with it because I had a plan.”

“A plan!”

“Don’t go popping a heart valve on me. See, he has this way of talking, and the other girls in the office hate it. Anytime one of them makes a mistake, comes back late from lunch, or takes too long on a smoke break, he’s like ‘guess I’ll have to take you over my knee, little girl.’ Or, ‘I might have to take down your panties and wallop that cute ass of yours.’ Shit like that. I swear, just the way he says ‘panties’ sounds like he can already taste them, chewing the crotch out of a pair just to get the juice.”

“Then you need to tell somebody about it. Whoever handles the hiring and firing. You don’t need to be making any plan.”

“I would, I would—but for your information, the person who handles payroll along with all the hiring and the firing, is his wife.”

“Then—great. Tell her and she’ll put a stop to it.”

“Fire her own husband? Use your head, Earl. She’ll fire one of us for being a tease or something. You don’t know anything about women, do you?”

“You don’t need to be making any plan that gets your ass beat black and blue.”

“Well—we can’t. So, no, we’re not going to tell her about it. That’s why I decided on a little scheme to break that habit of his.”

“Sounds to me like you finally found a reason to use your pepper spray on somebody getting too frisky with you. Be a lot simpler.”

“And get me fired.”

“You won’t break his habit, giving in like that.”

“Girls’d just laugh off whatever he’d say, but they still hated it. My plan was to call his bluff. Force him to make good on his little snide threats. So, the first time he said it to me, I just looked at him and said, ‘with hands that small?’ Well, I could see I zinged him good. He just stood there a second, gawping at me. I was going to leave him there like that, but then he said, ‘I’ve got just the thing for saucy little girls like you.’ He grabbed this leather paddle off the credenza behind his desk and aimed it right at me. I didn’t miss a beat, I just flipped up my skirt and pushed down my panties, leaned over his desk, and invited him to give me a few. Make him put up or shut up. Well, I could see he wasn’t ready for that.”

“Sybil, you started it.”

“I most certainly did not. He’s the one making overtures. All he had to say was ‘pull your panties up and get back to work’ but he didn’t. He got out that paddle thinking I’d maybe laugh and go on about my business. I could see he was waiting for me to back down, the way he nodded slowly, tapping the edge of that paddle in his hand, watching me. So I gripped the edges of the desk like I was bracing myself, squeezed my eyes shut and clenched my teeth, waiting for that first swat, showing him it sure-as-shit wouldn’t be me backing down. He sure looked to me like he was going to lose his nerve, watching him with that paddle. I could’ve smiled, pulled up my panties and been on my way—but I couldn’t help myself and I wiggled my ass. Let me tell you, that did the trick. ‘Okay, then, I guess you’re asking for it,’ he said and put his hand on my back, holding my skirt up and out of the way, taking his time. He gave me three solid swats. Not too hard, but hard enough that it stung. That should’ve been it. I was making a point about office decorum and figured he learned a lesson.”

“I guess he didn’t.”

“No, and I should’ve seen it coming. I snuck a peek while he was giving me those swats and could see his face all red and his breathing hard, him staring down at my ass. His hand was still on the small of my back, his thumb doing this little strokey thing, like he’s playing with the fuzz on the skin of my tailbone. Lucky for me, the phone rang, making him jump, or I’d probably still be there. Maybe if I hadn’t pulled my panties down that’d been the end of it. But it wasn’t, not by a long shot. It wasn’t a day later he said it again after I did something—I forget what—and I bent over the desk, flipped up my skirt, planning to leave my panties up this time, but no, he hooks his thumb in the waistband, right in the middle, and pulls them down sloooooowly, making the whole thing last, running his thumb right down the crack of my ass, deep between my butt cheeks, feeling his way down like he planned to play a little stink finger. Then, boy, he let me have it. I took it, thinking he was trying to make me give, say uncle, I don’t know what, but you know me, I’m not about to let anything get the better of me. I knew without looking he’d really reddened my ass. But I’ll tell you. Daddy did lots harder. With his hand. He’d make me pull everything down, jeans, panties, my swimsuit if we were at the lake, whatever, and him giving me however many he wanted to give. Hit lots harder, and never used a belt or switch.”

“Your daddy never used a belt?”

“Never had to. Just his hand. But—dang. You know what I really hated, getting a spanking from daddy?”

“I can’t imagine.”

“When he’d stop—just standing there behind me and I’m still bent over, thinking he was done—I’d straighten up and—whammo—he wallops me another one, saying, ‘did I say we were done?’ and he’d give me another half dozen. I never could be sure when it was safe to stand up, so I just laid there over the bed, or the arm of the couch or the table while he stood behind me, making up his mind if I needed a few more.”

“Which you probably did.”

“Now you’re sounding like this guy at work. He said I must’ve needed lots of spankings when I was in pigtails. I never wore pigtails after junior high. Too easy for guys to hold onto. What is it with you guys, not enough getting a blowjob or coming in the back door, you just naturally have to take hold of a girl’s pigtails.”

“I don’t recall ever grabbing you by your pigtails.”

“Because I stopped wearing them. Anyway—this guy gives me a whole dozen, taking his time, and I’m thinking he’s watching my ass jiggle each time that paddle lands with a thwack. I can feel my butt cheeks ripple. They’re solid, but nowhere near as firm like they used to be back in high school.”

“All that twirling practice.”

“You lose it in a hurry, you don’t keep it up—but he doesn’t seem to mind. When he finally finished, I heard him say ‘oh shit’ and glanced back to see he must have creamed his jeans, like we used to say. He flopped down in his chair, grabbed a binder and opened it up on his lap. He flicked his hands at me, shooing me away, saying that I needed to get back to work. Just to be mean, I laid there and rubbed my ass a minute or two more, then when I got up off the desk, I bent waaaaaay over to pull my panties up from around my ankles, giving him a whole long view of my veejay and my asshole. He had to be seeing it because I could feel the breeze from the air vent blowing cool air between my legs. I wiggled and I struggled and I tugged, cocking my hips first one way then the other like it was hard getting my panties up, all so he’d get a pretty good show.”

“With your not-so-firm-anymore cheerleader ass.”

“Watch it.”

“Sybil, if you just made him jizz his pants, at work, in the middle of the day, how’s he going to be thinking about office decorum with you shimmying your ass at him?”

“All right, Earl, yes, I miscalculated. I sort of created a spanking monster.”

“So that wasn’t the end of it.”

“No. Next few times? He didn’t bother with any excuses. Just said, ‘it’s time,’ and bent me over the desk, the copy machine, the hood of a car, whatever was handy.”

“No one’s hearing any of this?”

“I guess they can’t hear anything over the noise from the garage next door or the air conditioner running in the showroom. Even if they are, they won’t be saying anything. Because he’s leaving them alone, probably. Where was I?”

“On the hood of a car.”

“Right. And the way he came prepared. He’d pull out a hairbrush, or a ping pong paddle, or a leather slipper. Once he brought a riding crop. Must’ve swiped it from his wife. She’s into riding horses English style. Wears the funny helmet and puffy britches.”

 
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