Disciplining Caleb

I fucked up big time

May 29, 2023

It happened after she left for work. Everything was fine when I slid Anna’s breakfast across the marble breakfast bar while she put the finishing touches to our latte’s. We’d had a great morning chat, she went over a honey do list and I kissed her, handing over car keys when she forget them on the way to our front door.

“I’m skipping your maintenance spanking this morning Caleb.”

“Oh, why’s that babe?”

“You’ve been so attentive of late and it fells unnecessarily harsh.”

When I opened up my workshop in an old farm annex outhouse behind our home and checked progress on a diorama I’d started the day prior, the phone rang and that’s when my day went south.

I cursed her decision not to settle me into the day at the raw end of a leather paddle because I’d slipped up and Anna had found out. My misdeed prompted a call from her office PA, Kelly about ten minutes after my error.

I was in my car and driving to her office fifteen minutes after that.

On arrival at Global Dynamics I knew they were expecting me. Parking lot security waved me straight through and once inside, I was tagged as unescorted by a receptionist who confirmed my name was already entered into the visitors system. A badge printed on red plastic sitting in a little box was handed to me and I walked through nearby x-ray machines.

By the time I arrived at the end of Kelly’s desk my outlook was grim and expectations of a severe punishment were high.

“Wait in Miss Crawford’s office, Caleb. Our leader is taking a meeting but she’s very keen to see you. I rather wonder whether you’ve been naughty again. Could you shed any light on that please?”

She smiled sweetly and I knew with sincerity but Kelly was ruthless, almost as much as my girlfriend, especially with the men in both their lives. The pair were partners in crime having worked together since joining GD.

“Anna’s always taking a meeting. I have no idea what I may have done to vex her, but I’m sure you’ll know soon enough, Kelly.”

I sounded more frustrated than I’d intended, and most of my girlfriend’s outer office staff heard my outburst. They kept their heads down, but I knew everyone was acutely aware of my impending doom.

“C’mon Caleb, you of all people know Anna doesn’t appreciate sass.”

“Sorry, I didn’t mean that.”

Her personal assistant, Kelly, scowled, and I knew that moment of madness would cost me dearly. Anna didn’t like backtalk, and especially not when I did it at her place of work. I walked into my girlfriend’s inner office and sat in a comfortable brown leather wing-back chair close to her desk, beside a window overlooking nearby woodlands and the company car park.

A massive storm raged outside, sweeping the trees one way, then another, lashing the car park tarmac with monsoon rain. The dystopian feel of a landscape ravaged by nature and devoid of humanity mesmerized me, matching my mood while I waited expectantly for trouble to come in the form of a calm but vengeful girlfriend.

She wasn’t cruel or mean hearted. Actually, Anna was as perfect a girlfriend as a guy could hope to have but I’d lied to Kelly. I knew exactly what irked her boss, but I hid that embarrassment to defer everyone’s judgement as long as possible.

As a director at Global Dynamics, Anna got a well-furnished corner office, with private meeting and rest rooms. I enjoyed the opulence of her inner sanctum. As well as the chair I sat in, there were two luxurious three seater leather sofas and a single, Italian designed modern stainless steel curved chaise facing the panorama windows.

Most of all, I loved the office coffee. Kelly smiled warmly when she slid a steaming cappuccino onto the glass-topped table in front of me. I grinned boyishly back at her, noticing the big heart sprinkled in dark chocolate on a light, fluffy white cream layer.

“Thank you, Kelly.”

“We all love you, Caleb. I just wish you’d stop riling Anna up before she comes to the office. It’s hard enough dealing with the assholes outside our office without creating a demon inside.”

“Sorry, has she been vitriolic?”

She knelt down close to where I sat, staring kindly into my eyes. I wished with all my might to see up her pencil skirt but both legs were clamped shut. I love Anna, but what’s the harm in a little peek, right?

“Agreeing to a female led relationship is something to be proud of and enjoy, Caleb. You and Anna both do what you’re best at.”

“I know that. Look Kelly, I messed up and I’m sorry.”

“Be sure to show Anna your remorse, and I’m sure she’ll be lenient with you.”

“Do you think so?”

She stood up, smiled and shook her head at me as though I were a naughty puppy.

“I doubt it. I expect they’ll hear your yells from a thrashing down in R&D.”

She left me to my misery. I felt worse because I’d let myself and Anna down. My actual crime didn’t really trouble me that much.

From the table in front, I picked up the most recent company newsletter written by Anna and began reading. I was engrossed in the company financial reports by the time my girlfriend’s voice wafted from far down the corridor.

“Is he here, Kelly?”

“Yes Miss Crawford, but your 10AM appointment has arrived early.”

“Put Silas in the boardroom and give me ten, no, thirteen minutes alone with Caleb.”

I stood up, watched Anna stride into her outer office, not looking best pleased, and immediately wished I hadn’t sassed in front of Kelly. It was easier to misbehave in the absence of my girlfriend than when confronted by her intimidating beauty, incisive intellect, and dominant personality.

I watched the loyal personal assistant pass a yellow sticky note before shrugging at me because I knew she had to snitch. I’d added to my list of misdemeanors unnecessarily.

I reached Anna as she entered the room, kissing the cheek she offered with a smile. She looked very happy to see me, but then, discipline was always a measured rather than frantic process with her.

I closed the office door behind us, wincing because I suspected what was coming. I noticed the door was new and much heavier than the old one.

“Hi darling. Are you having a good day?”

How the fuck can I drag myself out of the shit?

“Caleb, you have about eight minutes to work some magic with your tongue on my pussy. If you aren’t between my legs in thirty-seconds, there’ll be trouble.”

Anna took my hands, pulling me towards her, while backing a firm ass into the office door. She kissed me deeply and my lips sizzled like butter off a hot skillet, my heart rate leaped while my girlfriend searched desperately for my tongue while grabbing my ass.

Maybe she doesn’t know.

“You seem frustrated Anna.”

“I am… bad meeting, then you told my mom to fuck off when she called.”

I froze. She definitely knew about the confrontation between me and my mother-in-law. Anna kept going, kissing me ever more passionately. When I didn’t reciprocate, she paused, opened both eyes and waited until I resumed service. Her sharp fingernails dug into my butt, scraping her itchy French knicker lace into me.

“You stole my knickers again.”

Anna giggled, but I knew she didn’t mind. I had a stack of my own, but today, I wore hers and enjoyed their snappy waistband and figure hugging feel.

She pushed my head downwards, forcing me gently to my knees while hiking up her red pencil skirt. I peeled my girlfriend’s sensible work panties off and thought I’d chosen better from her lingerie drawer this morning than she had. Anna stepped out and left me to pick up and pocket hers.

She ran her fingers through my hair seductively, gripped my thick locks tightly, and pulled my face gently into her crotch. She held me steady while shuffling her feet wider apart, pushing her thighs wide, and leaning more heavily against the door. Then she forced her hips far out, providing me with better access to lick her pussy.

I smelled her sweet arousal and saw copious cream eager to escape two pouting, swollen and freshly shaven labia. I collected sweet ambrosia from the creamy furrow between them greedily, making my tongue rigid and forcing its sides into a scoop shape. Then I licked her slit from bottom to top, swallowing twice, while Anna shuddered against the tip of my tongue.

“It’s been a shitty morning and you made it worse. This goes some way to reparation Caleb. You have been so fucking good lately, too.”

Anna rifled her fingers gently through my thick, black hair, then tweaked both earlobes, using them to pull me onto her preferred target at the top of a very creamy slit. I winced and licked harder, searching out the engorged clitoris that had risen from a delightful, soft pouch of protective skin.

“I got Kelly’s note, and you don’t get a pass on sassing her about me no matter how good you tongue. We’ll deal with you flagrant disrespect for mom too.”

I sucked harder on her clitoris, creating an intense vacuum around the swelling love nut, forcing her to wriggle and moan with delight against a solid wooden door. Then I moved downwards, chewing her labia gently, harvesting the thin veneer of seduction her glands had coated them with. All the while I kept stimulating Anna’s clit with my nose, building our pathway to her much needed relief.

Anna had become more prolific with her juice flow since our early cunnilingus sessions. I’d reassured her to provide me with more of her nectar, and she’d become confident knowing that I enjoyed her flavor and wanted as much of it as possible. The lady liked to squirt now I had given her the confidence to do so.

I went to work with a fervor, determined to satisfy my girlfriend and get her off on my tongue. Using two fingers from each hand, I peeled aside her pussy petals and stretched her clitoris wide, isolating it so I could flick its tip vigorously up and down, then drag the precious slimy pearl from side to side. I descended back into Anna’s heavenly hole and harvested whatever juice was available, making sure it didn’t dribble down her thighs.

I returned to her clitoris, sucked it hard, and then forced her protective hood out of the way, to flick the sensitive, treasured bean inside. I made progress, and she bucked like a broodmare on heat desperate for a stallion to mount her.

“Fucking hell Caleb, you’re so accomplished at giving a girl magnificent head.”

I was certain her office staff must have heard her butt and head slamming off the door while I worked Anna’s pussy. Then I realized why she’d had a new, heavier door installed.

Knock, knock, knock.

I knew it must be Kelly, because nobody else would dare disturb Anna’s closed door. I shit a brick, and looked up for instruction without resting my tongue.

“Keep going, no matter what,”

Anna’s voice and expression were reassuring, and I helped her shuffle off the door, onto the wall beside, cupping both ass cheeks in my hands, taking her weight.

“Come in Kelly!”

“Fuck!”

“What have I told you about talking while eating, Caleb? That’s three strikes.”

Kelly entered the room and casually stood beside us, closing the door behind her.

“How’s Caleb doing, Miss Crawford?”

“He’s almost there. Argh! Jesus Christ, Caleb! That’s it, stay right there! Fucking, go for it, Wonderboy!”

Anything beyond three strikes would mean a visit to the stables at Granger Hall and a horse whipping, so I continued doing my best work in silence.

I didn’t stop licking my girlfriend’s clitoris for a second, peeling its protective hood with my upper lip and lashing gently across the engorged bean inside, eliciting an explosion of muscle spasms from Anna’s midriff and thighs.

I felt Kelly’s fingers stroke my hair and circle my earlobes before pinching both. I knew she also performed cunnilingus on my girlfriend when required but assumed she must have been too busy this time.

“Let me help you, Anna.”

She placed a dossier on Anna’s desk, returned, and lent a shoulder for my girlfriend to lean on, smiling pleasantly at me almost willing my success.

“Keep going Caleb, I sense our leader is close to a conclusion.”

When she climaxed, Anna’s knees buckled, so I held the back of her thighs, making sure my girlfriend didn’t slide onto the floor. Kelly wrapped her arm more tightly around her boss to help steady our tryst.

I kept licking with a ferocity that forced wave after wave of intense pleasure through my beloved’s body. I felt the intense shuddering and almost came in my pants when Anna tilted her head sideways, stared at, then French kissed Kelly.

We supported Anna’s entire body weight between us and the naughty PA even sent a hand down my girlfriend’s washboard stomach to help me. Using a thumb and forefinger, Kelly splayed my girlfriend’s clitoris wide open by spreading the skin either side so I could get better traction with my tongue.

Anna detached from kissing Kelly for a moment, gasping and moaning like a whore.

“You two are a great team. I should do this more often.”

“I love working with Caleb, Miss Crawford. He’s such a well-behaved boyfriend.”

“Not so much today, Kelly but we’ll fix that.”

Anna’s orgasm came like a tempest when she squirted her excitement down my throat like a prize that I’d worked hard for, deserved, and one that she appreciated giving. Kelly kept the pressure on with her fingers, flicking Anna’s clitoris while I covered her pee hole with my mouth, collecting the unicorn milk we’d both worked hard for.

Anna was ovulating, and I think that, plus her boardroom annoyance, helped me make quick work of her sexual frustration.

I pinned my girlfriend to the door with her weight bearing down on me until I’d cleaned her properly, sucking each pussy petal dry while she rode the retreat of her climactic storm. When Anna was done, I carried her to a comfortable chair where she rested for a minute before going to the toilet to freshen up.

Kelly walked over to me and sat on my lap wrapping both arms around my neck. She looked impressed, and I felt proud.

“She won’t let you get away with it, Caleb, although I think you did admirably.”

“Thank you, Kelly.”

“I hope one day, Anna loans you to me, perhaps for the whole weekend.”

“I’d enjoy that.”

“I’d make sure we both did.”

When Anna returned, she seemed relaxed, and as though she’d just come home from a spa weekend.

“Thank you Caleb, you’re like one of those express tyre changing joints where they service you in just a few minutes.”

“What’s next, Miss Crawford?”

Kelly was obviously busy and wanted to move things along because she knew Anna was late.

“I must deal with Silas, so I’ll need you to punish Caleb for three counts. My mom, sass to you and speaking while eating. Go to level seven, please.”

Level seven… oh fuck, no!

Anna fished around in her handbag and retrieved an eight inch long, solid mahogany wooden hairbrush.

“Message me when you’ve finished or if Caleb becomes unruly. He’s getting fifty strokes, and his safe words are unchanged from last time.”

“Red, amber, green?”

“Yes, I have to go now.”

Anna kissed me and smiled, cupping my chin in her palm. I sensed a reluctance, like she’d ordered a punishment without wishing to.

“Do as Kelly says, and then you can go home… maybe.”

When the door closed, Kelly turned to me, smiling unsympathetically. She knew I was getting what I deserved.

“Shall we conclude this Caleb?”

“You could just say you did it and let me go.”

I smiled apologetically, begging for her mercy through an expression of sorrow and love although secretly I wanted the thrashing and especially so coming from her.

“You’re joking, right? You fuck up three times and then I lie to Miss Crawford to save your ass? She’d flay me alive.”

“At least go easy then, maybe?”

“Caleb! She’ll inspect your ass cheeks this evening, and expect level seven welts as evidence I followed orders. Let’s get this done, properly and honestly, then you’ll feel a lot better!”

“It’s a good point.”

I felt sorry for my transgressions, but I hated coming to Anna’s workplace almost as much as she did. Kelly was a bonus and I was pleased my girlfriend had outsourced my spanking to her super hot PA.

“Strip off and fold your clothes neatly, stacking everything on the chair.”

I undressed, racking my brains to contrive some leniency downwards from level seven without angering my punisher or her boss. Kelly was only doing her job, but I wished she wouldn’t enjoy it so much.

She relished my muscled physique while I disrobed and more nakedness became revealed. I stacked everything on Anna’s executive leather chair. I knew Kelly would never partake of me without Anna’s permission, nor I of her, despite her beauty. Such was our loyalty to my girlfriend.

“That’s an enormous cock, Caleb. I wish so much I could enjoy it.”

“I’d like that too. I think Anna is close to permitting us to have more fun.”

“But she’s not there yet, my sweetie.”

“No, and this misdeed doesn’t help matters.”

“Okay, naughty boy, get on your hands and knees, facing the window.”

In my nakedness, I felt a thrill and a shimmer of delicious, mild humiliation when I got down on the floor, adopting my punishment position. I faced the storm outside which matched my situation as Kelly strode around me swishing a brush that would soon correct my poor behavior.

My disgrace continued when Kelly gently kicked my knees wide apart, spreading my cheeks and exposing the puckered whorl between them.

Her phone vibrated and I turned, watching her check the message that undoubtedly came from Anna. She smiled wickedly and showed her screen to me.

Take your punishment well, Caleb. You did a good job eating humble pie.

“She loves you Caleb and only wants what’s best for both of you.”

“Yes, I know.”

“Raise your chin and look straight out of the window like a proud Roman centurion, Caleb, just the way Anna likes you.”

Kelly stripped down to her underwear and my cock got a great deal harder while staring at her slender beauty clad in pink French knickers and bar. Her long raven black hair beautifully offset a milk bottled, freckled complexion that drove me wild and I felt pre-cum oozing like a shameful slime from the slit in my bulging glans.

I knew Kelly must lose the tight clothes if we stood any chance of achieving evidence of the punishment Anna had demanded. She stroked my back longingly, sliding her fingers into my ass crack, brushing past the puckered sphincter that wanted her to finger bang it and until she cupped my balls, squeezing tightly while I whimpered.

“These seem very full, Caleb. When was the last time Miss Crawford serviced them?”

“It’s been a week.”

“Oh dear. It’s going to take some serious self control for you today.”

“Yes.”

Kelly sat astride my back, facing her target, while I had a view of the storm outside. The warmth of her pussy felt intense on my bare skin, and I knew our play had aroused her. She shuffled across my spine, getting comfortable while I settled into a sturdy platform for her use.

Her phone vibrated.

“Hang on it’s another message.”

“What did Anna say?”

She showed me the screen and I felt dismay.

Make it sixty strokes, Silas is being an ass and Caleb has really irritated me by his disobedience.

Kelly spurred her heels into my rib cage playfully, steadied herself and then draped her hair on my lower back, inspecting and lining up her target.

“It’s sixty now. We’d better get on with it and report back quickly.”

{Stroke} — Smack!

I felt a rush of air before each stroke when an intense, stinging pain transmitted from my ass cheeks to my brain. She’d struck my left cheek with full force on the first stroke and it surprised me, the pain felt violent and extreme but subsided quickly before the next blow came, this time on the right cheek.

I had an instant dopamine rush which lifted me, and by the fifth stroke it eased my pain. Adrenaline surged like a river in flood when Kelly repeated her spanking five times on each cheek, interspersed by equal pauses while counting aloud. Just when each sting abated, the next stroke came, and I wanted more. She’d reached twenty in no time, and I was heading for a gentle place with time and presence of mind to contemplate my wrongdoing.

{Stroke} — Smack!

An already thumping heart rate sped up, my mouth was parched, and my skin became electrified. My senses exploded with excitement, euphoria and every synapse dedicated to pleasure in my brain exploded, celebrating Kelly and her firm hand.

I entered a deep concentration emptied of all thought except for a vision of Anna and Kelly’s voice.

“It’s a punishment, Caleb, and I know you’re enjoying it too much. This is a teaching moment. If you don’t learn your lesson, it’ll be me on all fours and Anna climbing over my ass.”

{Stroke} — Smack!

Kelly’s spanking grew more intense, less bearable, but oddly, still desirable. I tried to relax, always focusing my thoughts on the instructions she gave. My butt cheeks burned, and the sensation felt painful, precisely on my threshold. I suddenly felt sorry on all three strikes of misbehavior. My hands went cold when blood flowed away from them and into my legs, preparing for flight.

“You’re sweating. I feel it through my panties. It’s not so funny now, is it?”

“No, I’m really sorry.”

“Apologize to Anna, not me.”

Kelly paused my beating long enough to thrust her phone in my face.

“Speak now.”

“Anna, umm, I shouldn’t have misbehaved. I’m really sorry and it won’t happen again.”

Kelly sent the voice memo and turned her attention back to my derriere.

“Work hard, Caleb, and make amends.”

“Thank you, Mistress Kelly.”

“Aww, Caleb, that’s nice! How do you feel?”

She placing her palm on my butt cheeks, taking my temperature to gauge the success of her stroke work. She dug her fingernails into the area she’d spanked, eliciting my painful shriek.

“I feel contrite.”

“Good boy! Last ten now, extra hard ones. Brace up, and be proud!”

I grimaced when the next stroke landed. Kelly broke through the numb warmth she’d created and sent a surge of pain and panic through me.

{Stroke} — Smack!

She paused again and I arched my back slightly, pointing my ass higher for a thrashing I was thoroughly glad to have had, while feeling glad it was almost over.

“Good boy Caleb. Who doesn’t enjoy a confident yet humble boyfriend? Use your safe words if you need them. Do you consent to these next five which will be the most painful so far?”

“Yes, Mistress Kelly.”

The next stoke must have raised a welt because its violence brought tears to my eyes. I needed to hold on, Anna was the prize, and I’d fucked up big time.

{Stroke} — Smack!

“Three more, Caleb! Good boy!”

I heard the door open without a knock and knew it must be Anna. Kelly paused and then let loose the final three in rapid fire succession. My knees buckled, but I didn’t let my punisher fall knowing that would be disrespectful.

{Stroke} — Smack!

I heard Anna chuckling before a short round of applause.

“Well done and thank you, Kelly. What do you have to say, Caleb?”

“I’m very sorry!”

“You’ll still need to apologize to mom but at least the worst is over.”

While my pain subsided, a burning sensation took hold, and I knew I’d be reminded of this beating for days to come and every time I sat down.

“You’d better get dressed, Kelly. Show Silas the door. He says he’ll sign our uniform redesign contract and send it back. Chase him up for it.”

“Yes, Miss Crawford.”

I felt her weight lift off my back when Kelly stood up, then helped me to my feet, smiling as if she were proud of a job well done. She dressed in silence while I remained naked.

“Sit down, Caleb and have a read of something. I could use some eye candy while I write this chapter of our lives into a story. What do you say to Mistress Kelly?”

“Thank you, Kelly.”

I grinned, then winced when I sat down.

They both chuckled, and Kelly took her leave.

“Try to be a good boy for Miss Crawford, Caleb. It makes life much easier for everyone.”

Kate Granger Fiction

Discussion about this post