The Office: Part V — The Date

You met Emily while waiting for Ms. Hollaway’s dry cleaning on Thursday afternoon.

She had been behind the counter at the little Park Avenue shop, folding a man’s dress shirt with quick, neat movements.

Mid-twenties, soft brown hair pulled back in a simple ponytail, a warm smile that reached her eyes when she handed you the garment bag.

You’d exchanged a few pleasant sentences about the weather, about how long you’d been working in the neighborhood. Nothing flirtatious.

Just easy conversation. Before you left she had slipped you her number on the back of the receipt.

“Text me if you ever want to grab a drink after work,” she’d said, cheeks pink. “I finish at six most days.”

After the long, humming silence of turn-down service the night before—after you had cleaned Richard from between Ms. Hollaway’s legs and coaxed that final soft sigh from her clitoris with your fingertip—the idea of Emily had felt almost possible. A normal evening. A normal girl.

One night where you were more than simply Ms. Hollaway’s perfectly contained assistant.

So after finishing work on Thursday, you had stopped at a midtown department store and bought a fresh pack of ordinary cotton boxer-briefs. The old ones were long gone, discarded weeks ago on Ms. Hollaway’s instructions.

Before your courage evaporated, you texted Emily a simple, careful message suggesting drinks after work on Friday. She replied almost immediately — warm and clearly pleased. Seven-thirty at a quiet bar a few blocks from the dry cleaner. It had felt, for a moment, like a small pocket of ordinary life.

Dressed in your new boxers on Friday morning, you set off for the brownstone in nervous anticipation. They felt strangely loose and unfamiliar under your suit trousers, like a costume from another life. Just one night, you told yourself. Ms. Hollaway would never even notice.

You arrived at the brownstone at nine sharp, as always.

Ms. Hollaway noticed before you had even set down her morning tea.

She was at her desk in the study, reviewing correspondence. Her eyes lifted, traveled over you with that calm, assessing gaze, and paused at your waist.

“Come here, dear. Stand properly in front of the desk.”

You obeyed. She studied you for a long moment, head tilted slightly.

“Turn around slowly.”

You turned. When you faced her again her expression held mild, clinical interest.

“Boxers today,” she observed, as if noting a change in the weather. “Cotton, I presume. The same ones you were instructed to discard weeks ago.”

You felt your face burn. “I—I did discard them, Ms. Hollaway. Weeks ago, like you said. These are… new. I bought them yesterday evening after I left. I was only going to wear them for tonight. Emily—the girl from the dry cleaner—she gave me her number when I picked up your things on Thursday. I texted her this morning about drinks after work. I thought… since I’d be going straight from here and wouldn’t have time to change, it would be all right. Just for one evening.”

The words tumbled out, half apology, half explanation. Your hands fidgeted at your sides as you tried to make the logic sound reasonable even to your own ears.

Ms. Hollaway regarded you for a long, unhurried moment, her expression one of calm, diagnostic interest rather than surprise or displeasure. She set her pen down.

“I see,” she said gently. “You discarded the old ones as instructed, then went out and bought new ones so you could play at being an ordinary man for Emily this evening. The panties, in your mind, are simply work uniform—something you change out of when the day ends.”

She gave a small, thoughtful nod. “But there are no compartments, dear. Those silk and microfiber panties aren’t a costume I make you wear for the job. They are honest packaging for your particular anatomy. They fit the small, responsive penis you actually have. They suit the boy who is learning to serve rather than perform. Trying to step back into cotton boxers is not a harmless wardrobe choice. It’s you attempting to step back into a role your body has already outgrown.”

“I thought—” you started again, trying to find some scrap of justification that might sound reasonable.

Ms. Hollaway lifted a single finger, silencing you with the smallest gesture. Her voice remained soft, almost maternal, but carried the calm weight of absolute certainty.

“You thought you could step out of my household for a few hours and play at being an ordinary young man,” she said gently. “But you are not an ordinary young man, dear. You are my personal assistant. When you walk out that door, you still represent me. If this sweet girl, Emily, is led to believe she is meeting a capable, properly equipped man who can satisfy her the way a woman expects to be satisfied… how do you think she will feel when she eventually discovers the truth—that the boy she liked has a small, quick little penis that was never going to be up to the task?”

She let the question hang for a moment, her tone laced with quiet, disappointed concern. “I can hardly have my assistant out in the world setting young women up for disappointment, can I? That reflects on my judgment. On my household. On the standard of honesty and care I expect from you.”

She rose from her chair and walked around the desk, stopping directly in front of you. Her presence was calm, close, and certain.

“This isn’t merely about underwear, dear,” she said, her voice low and instructional. “This is a lesson in attentiveness. In thoughtfulness. The women in your life—myself first and foremost, and now Emily—deserve better than a boy who makes poor choices the moment he thinks no one is watching. I am training you to put our needs ahead of your little impulses. To consider how your choices affect us.”

She placed a cool hand on your shoulder, her touch gentle but authoritative.

“Remove your trousers and those inadequate underpants. Put them on the desk. We’re going to correct this misunderstanding properly.”

Your stomach dropped. There was no anger in her tone—only the same patient certainty she used when correcting your reservation protocol or teaching you the difference between charmeuse and satin.

When you returned, stripped and bare, she was seated on the straight-backed chair she kept near the window.

Ms. Hollaway shifted, calmly pulling the hem of her wool skirt up to her hips. For a brief moment you caught a glimpse of her pale thighs and the delicate lace edge of her panties — the same soft silk charmeuse you had laundered so carefully. She patted her thigh once.

“Over my knee, dear. There’s no shame in it. A boy needs to present himself honestly. Trying to present yourself to Emily as an ordinary man who could give her what she expects is dishonest. That kind of deception doesn’t serve her, and it doesn’t serve me. Come now. Let’s make sure this lesson in honesty and attentiveness stays with you.”

You draped yourself across her lap. Then she guided you forward. The position felt new and intensely vulnerable; your first correction had been bent over the desk, not intimate like this.

“Between my thighs, dear,” she instructed quietly. “Your little penis goes right here.”

You obeyed, sliding your soft cock into the warm channel she created between her legs. She closed her thighs firmly around you, locking you in place with gentle but unmistakable pressure. The smooth skin and the faint warmth of her body held you snugly, trapped and contained.

She rested one hand lightly on the small of your back, the other stroking the curve of your bare bottom with clinical appreciation.

“Such a responsive backside,” she murmured. “Even now it knows its place better than your penis ever has.” Her palm delivered the first firm smack, then another, building a steady rhythm. The sting was warm and familiar. Eight strokes. Ten. Twelve. You counted them aloud in a shaky voice, the way she had trained you.

When the spanking ended she didn’t let you up.

Instead, her hand slid lower. Two cool fingers traced the cleft of your cheeks and found the tight ring of muscle that had fluttered so eagerly for her two nights before.

“You see, dear,” she said conversationally as the tip of one finger circled, pressing gently, “this is the part of you that actually knows how to receive. Your little penis tries so hard, but it’s simply not configured for the kind of sex you imagine having with a sweet girl like Emily. It twitches, it leaks, it finishes too quickly. It’s charming, in its limited way. But it isn’t built for a woman’s pleasure.”

Her finger withdrew briefly. You felt her reach to the side table, heard the soft click of a plastic cap, the wet sound of liquid being squeezed out. Her finger returned. It was slick, cool, and breached you slowly. The intrusion was intimate, invasive, and instantly overwhelming. You gasped, hips shifting involuntarily.

“There,” she said with quiet satisfaction. “Feel how your pussy opens for me? How it clenches and squeezes? That’s honest response. That’s what your body is actually made for.”

She began to move her finger with slow, deliberate strokes, curling just so, searching for the spot that made your breath hitch and your toes curl against the carpet.

Your cock, trapped between her thighs, gave a helpless throb but remained mostly soft—another piece of data she noted with approval.

“Emily sounds like a nice girl,” Ms. Hollaway continued, her voice warm and soft, even as her finger worked deeper. “She doesn’t deserve to be misled by a boy who shows up in borrowed boxers pretending he’s the same as other men. Honesty is kinder. To her, and to you.”

Another finger joined the first. The stretch burned sweetly. Your hips rocked in tiny, involuntary movements, pushing back onto her hand despite yourself.

“You’re getting close already, aren’t you? Not from that little button rubbing against my leg, but from your pussy being properly attended to. This is how you finish now, sweetie. This is the release that matches your configuration.”

Her free hand reached beneath you and gave your soft penis a single, almost affectionate pat.

“See? He knows he’s not in charge. He’s resting while your proper sex organ does the work.”

The pleasure built in a deep, rolling wave that had nothing to do with stroking your cock. It coiled low in your belly, behind your balls, radiating outward from every careful thrust of her fingers. She kept up the steady, instructional monologue.

“Honesty is the best policy, dear. You will call Emily in a moment and tell her the plans have changed. You will invite her here this evening instead of meeting at the bar. That way you are properly chaperoned. She will see exactly who you are in this household. No more pretending. No more compartments.”

Your breathing grew ragged. Your asshole clenched rhythmically around her fingers, greedy and helpless.

“Good boy. Let it happen. This is what your body needs. Not some awkward fumbling in a dark bedroom with a girl who expects a man. Just this. Open. Responsive. Known.”

The orgasm took you by surprise—deep, prostate-driven, hands-free. You shuddered hard across her lap, a long, whimpering groan escaping as your cock gave a few weak, dry twitches between her thighs. No real spurts; just the rolling, emptying release that left you limp and floating.

Ms. Hollaway kept her fingers inside you through the aftershocks, stroking gently, letting the lesson settle into your bones.

“There we are,” she said softly, pleased. “A proper, honest orgasm. Much better suited to you.”

She eased her fingers free and helped you to your knees on the carpet in front of her. Your face was flushed, your breathing still unsteady.

“Stay exactly as you are, dear. On your knees.”

She rose smoothly, smoothing her skirt back down, and crossed to the desk where your trousers and phone still lay. You remained kneeling on the carpet, flushed and spent, the deep ache in your ass and the memory of her thighs still vivid.

She returned a moment later and held your phone out to you.

“Call her now, dear. While the lesson is still warm in your body. Tell Emily you’d like her to come to the house this evening instead. Say that your employer has expressed an interest in meeting the young woman who was kind enough to help with my dry cleaning. Be polite. Be clear. And do not make excuses.”

Your hands shook as you found her number. Emily answered on the second ring, her voice bright and surprised to hear from you so soon.

You managed the words Ms. Hollaway had instructed, your voice thick and slightly hoarse. Emily sounded puzzled but flattered. After a short exchange she agreed to come by at seven-thirty.

“Wonderful,” Ms. Hollaway said when you ended the call. She stroked your hair once, almost maternally. “Now go upstairs and put on the proper panties. The navy microfiber today, I think. And the corset, of course.”

She stood looking down at you, smoothing her skirt.

“After you’re dressed correctly, you will launder those ridiculous boxers and add them to the rag bin. They are no longer part of your wardrobe. There will be no more experiments with compartments. You are my assistant, fully and completely. The garments I provide suit your anatomy and your role. Everything else is unnecessary theater.”

You rose on unsteady legs. As you reached the doorway she added, almost as an afterthought:

“And dear? When Emily arrives, you will greet her at the door in your proper uniform. No hiding. No performance. Just honest service. I think she’ll find it illuminating.”

You spent the rest of the afternoon in the corrected garments—silky microfiber hugging you snugly, the corset enforcing perfect posture. You prepared the guest bathroom. You set out a simple tray of refreshments. You tried not to think too hard about what seven-thirty would bring.

At seven twenty-five the doorbell rang.

You glanced at Ms. Hollaway, who gave you a small, encouraging nod from her armchair.

Your heart hammered against the boning of the corset. The navy microfiber panties cradled you perfectly, exactly as Anna had engineered them to do.

You opened the door.

To be continued…

This is the fifth in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service

The Office: Part IV — Turn Down Service

You flushed the toilet and watched your cum swirl away and then washed your hands under her watchful eye.

“Good.” She opened a small drawer and withdrew a tiny object. It was a chastity device. Plastic. A pale, shell pink. “This is for the rest of the evening. It’s not for you, understand? It’s for Richard.”

She knelt before you and fitted it. The cool plastic ring went around the base of your scrotum, the tiny cage encapsulating your limp penis. It locked with a small, brass padlock. She tucked the key into her bra.

“Richard is a traditional man. His masculinity is… tangible. Your presence, as my assistant, could be misconstrued as a threat. This,” she tapped the pink cage lightly, “communicates the reality. It tells him there is only one man in this home. And eventually, in my bedroom. It assures him your role is what it appears to be: service. Not competition. Do you understand?”

You looked down at the absurd, humbling pink nub between your legs. “Yes, Ms. Hollaway.”

“Excellent. Now, get dressed. He’ll be here in twenty minutes.”

Dinner was a quiet, civilized affair.

You served. You poured wine. You cleared plates. Richard was indeed a gentleman—polite, mid-fifties, with an easy confidence that filled the dining room.

He complimented her, the food, the wine. He spoke to you with a neutral courtesy. You were furniture. A well-trained piece of furniture in a corset and panties, with a pink cage hidden under your trousers.

After dessert, Ms. Hollaway rose. “Richard, if you'd like to retire to the living room, we can enjoy some coffee before we move to the bedroom? My assistant will do the turn-down service.”

Richard nodded, giving her a warm smile. “Of course, Millie.” He left the room.

She turned to you. “Go up. Turn down the bed. Light the candles on the dresser. Draw the curtains. Then wait for me.”

You did as instructed. The bedroom was softly lit, intimate. You turned back the duvet, fluffed the pillows, lit the candles. You were about to leave when she entered, still in her slip dress.

“No. You’ll stay. I may need you during my engagement. Water. Lubricant. A condom. You are here to tend to my needs.”

She pointed to the far corner, near the armoire. “Stand there. Lower your trousers and panties to mid-thigh. Place your nose against the wall. Your job is to listen to me. If I call, you come. You do not turn around unless instructed. Is that clear?”

A cold, heavy dread mixed with a dizzying excitement settled in your gut. “Yes, Ms. Hollaway.”

You walked to the corner. You unbuckled your trousers, pushed them and your silk panties down to your knees. The cool air hit your exposed buttocks and the pink cage. You leaned forward, your forehead touching the wallpaper. You heard Richard enter the room behind you.

“Everything ready, darling?” he asked.

“Perfectly,” she replied. Her voice moved closer to you. “There’s just one thing, Richard. I want to be entirely transparent about the domestic arrangements.” Her hand rested on your bare shoulder. “Turn around, dear. Show Richard your little guy.”

You turned, keeping your eyes downcast. You were exposed from the waist down, the corset laced tight around your midsection, the pink plastic cage a glaring declaration over your limp, tiny penis.

Richard’s gaze was calm, curious. Not cruel. Not gloating. He looked, then looked back at her.

“As you can see,” Ms. Hollaway continued, her hand now gently cupping the pink cage, “my assistant is not… configured for the usual male roles. He’s in panties. He’s in a cage. He’s here to serve my practical needs. He isn’t the kind of man who would ever be in your position. He knows that. His body knows that. This just makes it clear to everyone.”

She spoke about you as if you were a unique appliance. Her tone was warm, explanatory.

“It’s important to me that you feel comfortable, Richard. That you understand there’s no ambiguity. There is only one man in this room.” She let go of the cage and turned to Richard. “Now, I'd like you to show him what a real man looks like. Would you mind?”

Richard, with a slight, almost apologetic shrug, unzipped his trousers. He wasn’t showboating. He was complying with her request, a quiet participant in her lesson.

He freed his erection. It was thick, substantial, the complete anatomical opposite of what was locked in pink plastic between your legs. The comparison was so stark it felt less like humiliation and more like a simple, devastating fact.

“You see, dear?” Ms. Hollaway said, her voice soft. She wasn’t addressing Richard anymore. She was speaking to you. “This is what a woman needs. This is what satisfies. This is why you are in panties, and why he is not. Do you see?”

You stared at the floor, your face on fire, your penis shrinking. “Yes, Ms. Hollaway.”

“Good.” Her hand, which had been cupping the pink cage, drifted lower, her fingers curling beneath to cradle your scrotum. Then her hand slid further down between your thighs, palm pressing against your perineum, her fingertips seeking and finding the tight hole between your cheeks. Your most sensitive and private spot. Your rosebud.

“You know, Richard,” she said, her tone conversational, “while his penis is clearly… inadequate, I’ve noticed he has a very lovely backside. Quite shapely. Firm. Responsive.”

Her finger pressed upward, gentle but insistent, inward just past the tight ring of muscle with a slow, inexorable pressure.

A bolt of sharp, shocking pleasure lanced through you, making you flinch and gasp.

Your asshole clenched instinctively around the intrusion, a frantic, helpless pulse against her finger. It was an foreign sensation—invasive, humiliating, and yet your body betrayed you with a rush of dizzying heat.

Your caged penis throbbed in futility in its plastic prison, as if trying to harden against its constraints. You had never been penetrated before. And now she was fingering you in front of another man, while she discussed your anatomy in clinical terms.

“There, you see?” she said, a note of discovery in her voice as she withdrew her finger slightly, still circling. “A clench. A reflexive wink. Promising.” She looked over at Richard. “What do you think? Might his pussy be trainable?”

Richard’s expression was calm, almost amused, his voice considering. “Possibly. We'd have to see it to know for sure.”

“Yes, of course. One must examine the facts before rushing to judgment.”

Her finger entered you again, fingering your asshole like it was a woman's pussy. “Now, dear, be a good boy, turn around, bend over. Put your hands on your knees and present for us. Let Richard get a proper look at your pussy.”

The command, so gently delivered, unspooled your last shred of dignity. You turned, bent forward, placing your hands on your knees, your backside thrust into the room, the pink cage dangling absurdly between your legs. The cool air hit your most private hole.

“Good boy. Now, pull your cheeks apart, dear. Show us your pussy.”

Trembling, you reached back and took a buttock in each hand, spreading yourself open, exposing your tight, hidden rosebud to their combined gaze. The vulnerability was absolute, dizzying.

“Lovely,” Ms. Hollaway murmured. She stepped closer. You felt the pad of her finger again, slick now with saliva or some other fluid, circle your exposed opening.

“Look at that, Richard. It’s already fluttering. It’s a nervous little thing, but it’s alive. It responds to touch.”

She pressed the very tip of her finger inside you again, past the first tight ring of muscle. The pleasure was intense and made your legs shake.

“Oh, yes. Very responsive. I think, with the right training… and the right trainer… this could become quite a useful sexual organ. A way to contribute. To be of service in a more complete way.”

She withdrew her finger slowly. “You can stand up, dear. And release your cheeks.”

You straightened, your face molten with shame, your body humming with the alien, invasive thrill of her exploration. Your cock, trapped and useless, throbbed painfully in its pink prison.

“Thank you, Richard, for your professional opinion,” Ms. Hollaway said, as if concluding a consultation. “It’s something to consider for his ongoing development. Now,” her voice shifted back to its prior firmness, addressing you. “You may stand up, dear. Nose to the wall. And listen.”

You stood, pressing your forehead to the wallpaper once more. You heard the soft sounds of them moving to the bed. The rustle of fabric. The creak of the mattress. Then, her voice—soft murmurs, sighs, gentle directives.

Then, the sounds began, wet and purposeful. Her soft moans, his low grunts. Pleased. A man doing what you never could. You pressed your forehead harder into the wallpaper.

“Dear,” her voice came, slightly breathless but composed. “The nightstand. The condom. Bring it here and fit it on him.”

Your stomach lurched. You turned, eyes fixed on the floor, and shuffled to fetch the small foil packet from the drawer.

You approached the bed. Richard had paused, his substantial erection glistening at the tip. He looked at you, not with malice, but with a kind of detached courtesy.

Ms. Hollaway lay beside him, her head propped on pillows. She nodded toward Richard’s cock.

“Go on, dear. Be careful not to tear it.”

Your hands shook as you tore the packet and unrolled the latex down the length of his thick cock. The heat of him, the sheer substance, made your own caged insignificance scream in your head. You finished, your task complete.

“Good. Back to your corner.”

You retreated, the image of his sheathed cock burned into your vision.

You stood there. In your corner. In your panties and cage. Nose to the wall. Listening.

She called for you again. “Lubricant, dear. On the nightstand.” You fetched it, eyes averted, handed it to her outstretched hand, and returned to your corner.

Then the rhythmic sounds of fucking. You imagined his cock moving in and out of her pussy. The thrusting back and forth.

The event seemed to last both an eternity and a single breath.

Finally, you heard Richard’s low, guttural groan, her sigh of completion, the subsequent quiet and the soft, wet sound of separation.

“Dear,” she said, her voice languid. “The condom. Remove it. Tie it off and dispose of it in the en suite waste bin. Be neat.”

You turned again. Richard had rolled off her, lying on his back. You approached, avoiding looking at either of their faces.

Your fingers, clumsy with shame, held the base of his spent cock and rolled the condom off him. It was heavy, warm. You tied a knot in the open end, carried it to the bathroom, and dropped it into the bin. You washed your hands, the scent of latex and sex on your fingers.

Soft footsteps. Richard, dressed again, paused by the door. “Goodnight, Millie. Thank you for a lovely evening.” He left as you returned.

Silence, thick and humid.

“Now, dear,” she said, not moving from the bed. “A warm washcloth, please. From the en suite. And the bottle of almond oil from my vanity.”

You ran the water until it was warm, soaked a soft cloth, and wrung it out. You fetched the small glass bottle. You stood by the bed, waiting.

“Clean me up. Gently. Then a few drops of oil. Your hands are adequate for this.”

She lay back, legs slightly parted. You knelt beside the bed. With the cloth, you dabbed carefully at the slickness between her legs. The musk was intense, the smell of sex mixed with the scent of the lubricant.

You were cleaning another man’s cum from her skin. When you were done, you unscrewed the bottle and poured a little oil into your palm. You smoothed it over the folds of her pussy with trembling fingers, the skin soft and warm under your touch.

“There. That’s better,” she murmured, but her hand came up and closed around your wrist, stilling your broad, nervous strokes.

“Now that you've moisturized, we move to function. After intercourse, a woman's pussy needs soothing. It needs a gentle, attentive touch to ease it down from the pounding.”

She guided your index finger upward, through the slick folds, until the pad of your fingertip rested against a small, firm nub at the apex of her pussy. "This is my clitoris. It’s been neglected during the main event. Your job is to apologize to it. To coax a soft, gentle finish from it. Can you do that?”

“Yes, Ms. Hollaway,” you whispered, your voice thick with a mixture of awe and terror.

“Good boy.” Her hand remained over yours, a warm, commanding weight. “Now, apologize. With your touch. Not with words. Gentle circles. Imagine you’re tracing the rim of the most delicate china cup. Slow. Reverent. There. Yes. Just like that.”

You obeyed, your finger tracing slow, tentative circles. Her breath hitched, a soft, approving sigh.

“You feel how swollen it is? How tender? That’s from the neglect. Your touch is the apology. Now, listen to it. It will tell you what it needs. A little more pressure… there. A little slower… yes. You’re not forcing. You’re inviting. You’re asking it to let go of the tension and simply… enjoy.”

Her guidance was hypnotic. "Round and round, consistent pressure. Good... yes... just like that... just like that..."

Your world narrowed to the tiny, throbbing point under your fingertip, to the subtle cues of her body—the slight arch of her back, the minute tremble in her inner thigh.

You were no longer just touching her; you were deciphering her, learning a new, silent language of pleasure.

“That’s it,” she breathed. “You’re a natural penitent. Now, keep the rhythm. Steady. Consistent. You’re not chasing an earthquake. You’re coaxing a sigh. Almost there… just… let it happen.”

Her body tightened, not with the violent clench of her earlier orgasm, but with a slow, sweet ripple of release.

A long, soft sigh escaped her lips, and her whole body seemed to melt into the mattress, satiated and content.

“Perfect,” she murmured, her voice drowsy with satisfaction. “That was a perfect apology. You may stop now.”

You lifted your finger, glistening and trembling. She lay there, eyes closed, a faint smile on her lips.

“You have capable hands, dear. When they’re properly directed. You’ve learned the liturgy of my pleasure. We’ll practice until your touch on my clitoris is an act of worship.”

Her voice was soft, languid from the bed. She turned her head on the pillow to look at you. “You did very well tonight. You served perfectly.”

She looked relaxed, sated. “You saw the difference. You heard it. There is no shame in it. It’s simply anatomy. Your role is different. And now you understand it more completely.”

“The key to your cage is on the dresser,” she said, nodding toward the vanity. “Bring it to me.”

You fetched the small brass key. Returning to the bedside, you handed it to her. She reached up, took it, and unlocked the cage. She placed the open device in your hand.

“Clean this,” she said, nodding toward the cage in your hand. “Put it in the top drawer. It will be part of your kit.”

You took the pink plastic to the en suite, rinsed it under warm water, dried it with a towel, and placed it in the vanity drawer as instructed.

When you returned to the bedside, she was still lying there, the sheet pooled at her waist. Her eyes drifted down to your naked groin, where your small, soft penis hung, finally free of its prison.

“Look at that,” she murmured, a faint, affectionate smile on her lips. “So cute when it’s just resting. A little button.”

As if hearing her, your penis gave a tiny twitch, thickening slightly under her gaze. “And so responsive,” she observed, her tone warm with approval. “Even now, after everything, it listens. It knows its owner.”

She settled deeper into the pillows, her eyes holding yours. “And that is the final rule, dear. Your penis belongs to me now. Its function—when it hardens, when it softens, when it releases—is managed. You are not to play with it without my express permission. Is that clear?”

“Yes, Ms. Hollaway.”

“Good. Pull up your panties. Tuck me in, then you may go home.”

You did up your pants. Then you pulled the duvet up over her, smoothing it around her shoulders. She closed her eyes.

“Sleep well, dear. I’ll see you at nine. And tomorrow, you’ll wash the sheets.”

You walked out of the bedroom, down the stairs, out into the night. The memory of the sounds played on a loop in your head. The image of Richard’s cock, vivid and undeniable, was seared onto your eyelids.

You didn’t feel angry. You didn’t feel jealous.

You felt, with a terrifying clarity, that you had finally seen the blueprint. And you understood your place in the structure. It was a small, quiet, pink place. And it was yours.

This is the fourth in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training

The Office: Part IX — The Laboratory

The walk from Ms. Hollaway’s brownstone to Emily’s apartment was six blocks, but it felt like a migration between worlds.

You walked a half‑step behind the three girls, the leather ballet flats Ms. Hollaway had provided for outdoor wear soft against the pavement.

You’d been to Emily’s apartment before, but never like this—not as a training model, not with an audience.

The cool evening air seeped through the silk of your panties, a constant reminder of your exposure. The pink cage was a familiar weight, its small lock clicking faintly against the plastic with each step, a chaperone ensuring your attention remained where it belonged: on them.

Emily led, clutching the small brass key in her coat pocket. Maddie and Nicky flanked her, their voices a low, excited murmur you weren’t meant to overhear, though you caught fragments.

“…so we just… tell him what to do?”

“She said assume, don’t ask. Like, ‘come here,’ not ‘will you come here?’”

“God, my heart’s pounding. This is so weird.”

“Weird good, though. Right?”

Emily’s apartment was a third‑floor walk‑up, cozy and cluttered with the artifacts of an ordinary college girl: textbooks stacked on an IKEA coffee table, a fuzzy pink blanket draped over a sofa, a scented candle burning on the windowsill.

The normalcy of it made your own appearance—the corset, the panties, the cage—feel surreal, like a specimen brought into a living room.

“Okay,” Emily said, shedding her coat and tossing it over a chair. She turned to you, her expression a mix of nervousness and determination. “Stand there, please. In the light.”

You moved to the center of the room, near the sofa, and assumed the posture Ms. Hollaway had drilled into you: feet together, hands clasped lightly behind your back, gaze lowered but not fixed on the floor—a respectful middle distance.

The three girls settled on the sofa, facing you. For a long moment, they just looked. The seminar had been theory; this was the specimen.

“His hands are shaking,” Nicky observed softly.

“He’s excited,” Maddie corrected, her tone more assured. “Look at his chest. His breathing’s shallow. And his… you know.” She gestured vaguely toward your caged groin. “I bet he’s hard in there. That’s what she said—it’s an indicator light.”

Emily nodded, absorbing this. “Right. So his penis is saying yes. Even if he’s nervous.” She took a deep breath. “We should confirm the diagnosis."

She turned to you. Smiled. “Take off your clothes. Show us your indicator light.”

You bent to remove the ballet flats, then took off your shirt, reached behind you to work the laces of the corset. The familiar routine of undressing under instruction was a form of relief.

The corset loosened, and you slipped it off your shoulders, letting it fall to the floor. Your panties were next and then you were just standing there in your pink plastic cage. The cool air of the apartment raised goosebumps on your skin.

Maddie leaned forward, her eyes fixed on your groin. “See? The cage is straining at the front. He’s definitely hard. The light is on.”

“Good,” Emily said, her voice firming. A faint, knowing smile touched her lips. “I’ve used his mouth on our first visit. He’s a virgin but he did quite well. But tonight isn’t about my pleasure alone. It’s about your education. So, first practical lesson. We use what he’s equipped for. His mouth.”

She stood up and came to stand before you. “Kneel.”

You sank to your knees on the rug. The change in height put your face level with her waist.

“Good,” she said, more to herself than to you. She looked back at Maddie and Nicky. “She said his pleasure is derivative. It comes from our satisfaction. So we don’t worry about him. We just… use the tool.”

With a deliberate motion, she unbuttoned her jeans and pushed them down her hips, along with her cotton panties. She stepped out of them, leaving them in a small pile on the floor. Then she placed a hand on your head, not roughly, but with a steadying pressure.

“Your mouth is for our convenience,” she said, her voice gaining a thread of certainty. “You may begin.”

You leaned forward and pressed your mouth to her pussy. She was already warm, slightly slick from anticipation. You began to move your tongue in the slow, attentive rhythm she had shown you the first time—broad, flat strokes, focusing on her clitoris, listening for the shifts in her breathing.

A soft sigh escaped her. “Oh… okay. Yeah. That’s… that’s good.”

From the sofa, Maddie and Nicky watched, rapt. After a minute, Maddie stood up. “My turn. Share the resource, right?”

Emily nodded, stepping back, her face flushed. “Switch.”

Maddie took her place, shedding her own jeans and underwear. She was completely shaved, her labia fuller and more pronounced than Emily’s, glistening with arousal.

She guided your head with both hands, setting a slightly faster pace. “There. Just like that.” Her taste was different—muskier, saltier, more immediate. “See, Nicky? He’s not doing it for himself. He’s just… a thing. A very attentive thing.”

Nicky, still on the sofa, hugged a cushion to her chest. “Does it feel… different? Than with a guy who’s, you know, fucking you?”

“Yeah,” Maddie said, her voice tightening with pleasure. “It’s… cleaner. There’s no performance. No worrying if he’s gonna last or if he’s hitting the right spot. He’s just… servicing. It’s like using a really good vibrator that happens to breathe.”

Emily sat back down beside Nicky, pulling the fuzzy blanket over her lap. “That’s what Millie said. He’s a utility. Not a boyfriend.”

Maddie’s breath hitched, and her grip on your hair tightened. A few moments later, she shuddered and pushed your head back gently. “Okay. Enough. That was… efficient.” She stepped away, pulling her jeans back on without bothering with her panties. “Your turn, Nicky.”

Nicky shook her head, her cheeks pink. “I’m… I’m okay just watching for now.”

“Suit yourself.” Maddie flopped back onto the sofa. She looked at you, still kneeling on the rug, your chin glistening. “He’s still hard. Look at the cage—it’s straining at the front.”

Emily leaned forward, peering. “You’re right. So his penis is still saying yes, even though he’s not… getting anything.”

“That’s the point,” Maddie said. “His pleasure is in us using him. He doesn’t need to come to be satisfied.” She paused, then a mischievous smile touched her lips. “Though Millie did say we could milk him if we wanted. For practice.”

The room went quiet. The word “milk” hung in the air, clinical and intimate.

“I don’t know if I can do that,” Nicky whispered.

“Why not?” Maddie’s tone was challenging but not unkind. “She said it’s just maintenance. Like… draining the oil on a car. He needs it. And we’re supposed to be learning to manage him and his little penis.”

Emily bit her lip, her eyes on the brass key she’d placed on the coffee table. “She gave us the key. She said to use it thoughtfully. I think… I think we should try. How else do we learn?”

They fell silent again, the only sound the soft hum of the refrigerator from the kitchen. You remained on your knees, the cage a persistent, aching presence. The girls’ uncertainty was palpable, but so was their curiosity—the same curiosity that had brought them to the seminar.

It was Maddie who broke the silence, her voice dropping into a conspiratorial register. “You know, this whole thing… it makes you look at other guys differently.”

Emily glanced at her. “What do you mean?”

“I mean, think about it. Millie said the world is full of anxious, twitchy little men pretending to be something they’re not. Guys who are super eager to please, who get flustered easily, who are always offering to do things for you but never make a real move.” Maddie ticked the traits off on her fingers. “Sound familiar?”

Nicky’s eyes widened. “Oh my god. Like… like Jason in my econ study group.”

“Exactly!” Maddie leaned forward, her earlier nervousness replaced by the thrill of a puzzle falling into place. “Jason is always bringing me coffee, offering to carry my books, laughing too hard at my jokes. He’s cute, but he’s so… jumpy. And he’s never had a girlfriend. I always thought he was just shy.”

Emily nodded slowly, her gaze drifting to you as if you were a reference diagram. “Millie said the anxiety and the eagerness to please are somatic realities. They come from the… the configuration.”

“Right,” Maddie said. “So Jason probably has a small penis. And he’s terrified anyone will find out. So he overcompensates by being super‑helpful, but he can’t actually be a boyfriend because he can’t perform. He needs to be managed, not dated.”

Nicky let out a small, astonished laugh. “Holy shit. That… that actually makes sense. What about Ben? From the library?”

“Ben with the glasses who always stammers when you talk to him?” Emily said. “Yeah. Definitely. He’s built the same way.”

“And my cousin’s friend, Leo,” Maddie added. “He’s, like, twenty‑five and still lives at home. Super sweet, does all the cooking when I visit, but he’s never brought a girl around. My cousin says he’s ‘just a late bloomer.’” She made air quotes. “I bet he’s not a late bloomer. I bet he’s just… small. And no one’s ever taken him in hand.”

The conversation gained momentum, tumbling from one example to another. They weren’t being cruel; they were diagnosing, their voices filled with the dawning excitement of a new lens through which to view the world.

Each anecdote was a piece of evidence: the boy who was great at listening but froze when a girl tried to kiss him; the guy who was always offering backrubs but never made a sexual advance; the friend‑zone fixture who remembered birthdays and brought soup when you were sick but somehow never became a boyfriend.

“It’s not their fault,” Emily said, her voice softening with something like pity. “They’re built wrong for the standard script. They’re trying to follow a manual written for a different model.”

“And they’re failing,” Maddie said. “And making girls unhappy in the process. Because we expect them to be able to fuck, and they can't.” She looked at you, her expression thoughtful. “But if you manage their penis correctly… they can be useful. Happy, even.”

Nicky hugged the cushion tighter. “So… what? We track down all the small‑penised guys we know and start training them?”

“Maybe not all of them,” Emily said. “But… maybe one. As a next step. After we’ve practiced on him.” She nodded toward you.

“Or,” Maddie said, a slow grin spreading across her face, “we train them together. Like a… a study group. Can you imagine? Jason and Ben and Leo, all in panties and cages, learning to be attentive together. They’d probably be relieved. No more pretending.”

The image hung in the room—absurd, yet perversely logical. The girls fell silent, considering it. The scent of the scented candle—vanilla and lavender—mixed with the musk of their arousal and your own humid presence.

Emily’s eyes returned to the key. “Okay. Before we plan a whole curriculum… we have a practical exam tonight.” She picked up the key. “Milking. We should do it. For our education, and for… his maintenance.”

She stood up and came to kneel in front of you on the rug. Maddie joined her, sitting cross‑legged to the side. Nicky remained on the sofa, watching like a clinical observer.

“Millie said it’s prostate stimulation,” Emily murmured, more to herself than to anyone. “We need lube.” She looked at Maddie. “Top drawer of my nightstand.”

Maddie fetched a small bottle of clear lubricant. Emily took it, her hands steady now. The nervous girl from the brownstone was gone, replaced by a determined apprentice.

“On your hands and knees,” she instructed.

You obeyed. The change in position presented your ass and cage rear to them.

Emily squeezed a generous amount of lube onto her fingers. “Okay. We’re going to unlock the cage first. To… to access everything properly.”

She fitted the key into the small brass lock. The click was deafening in the quiet room. She carefully removed the pink plastic, setting it aside on the rug. Your erection, freed, sprang up, small and eager.

“See?” Maddie said, her voice clinical. “He’s definitely ready. The cage was just containing the evidence.”

Emily nodded. “Now.” She placed a hand on your hip to steady you, then guided her other hand between your cheeks.

Her touch was cool, probing. “Relax,” she said, her voice low and firm. “This is for you. It’s maintenance. It’ll settle you.”

Nicky, watching from the sofa, let out a small, nervous sound. “You’re really going to… put your finger in his ass?”

“It’s not an ‘ass,’ Nicky,” Maddie corrected, her tone matter-of-fact. “Look at him. It’s his other hole. His functional hole.”

Emily’s lips curved into a faint smile. “Millie said it's like a pussy. So that’s what it is. His pussy. Now hush, I need to concentrate.”

A soft, shared giggle escaped the three of them—a brief, bright sound that dissolved the remaining tension in the room.

You took a shuddering breath and tried to obey. Her finger pressed against your asshole, then slid inside. The sensation was intimate, invasive, but her tone held no cruelty—only focused instruction.

“There,” she said. “Now… we’re looking for the prostate. It’s supposed to be… a small, firm bump. About two inches in.”

She moved her finger slowly, her brow furrowed in concentration. Then her expression cleared. “Oh. There. I can feel it.”

Maddie leaned closer. “It’s like… his clitoris on the inside,” she said, her voice clinical.

Nicky, who got off the sofa and moved to peer from behind Maddie’s shoulder, whispered, “His button.”

Emily nodded, a soft murmur escaping her lips as she began to massage the spot with the pad of her finger. “That’s right. I’m pressing his button.”

She began to massage the spot in slow, steady circles. Almost immediately, a jolt of pleasure shot through you, and a soft moan escaped your lips.

“He likes it,” Maddie observed, grinning.

“Of course he likes it,” Emily said, her confidence growing with each second. “This is how he’s wired. His little penis isn’t the main event.”

She increased the pressure slightly, her rhythm becoming more assured. “Watch his back. See how it arches? He's humping my finger with his pussy. And his… his penis is twitching. Dripping.”

It was true. Pleasure was building in a slow, inexorable wave, centered not in your cock but deep inside, where her finger worked with calm certainty.

The girls’ gossip, their planning, their clinical observation—it all faded into a blur. Your world narrowed to the pressure of her touch, the sound of her breathing, the warm glow of being used exactly as you were designed to be used.

“He’s close,” Emily announced, her voice calm.

“Here,” Maddie said, guiding Nicky’s hand. “Hold his little penis. It’ll squirt when he comes. Catch it so it doesn’t make a mess.”

Nicky’s fingers, cool and tentative, closed around your shaft. Her touch was light, almost reverent, as if holding a small, fragile animal.

“Now,” Emily said, and she curled her finger just so.

The orgasm rolled through you, silent and profound. It wasn’t the explosive release of a traditional climax, but a deep, milking squeeze—a slow, helpless pulsing. Nicky’s hand tightened instinctively as your cock twitched in her grip, and a few weak spurts of seed spilled into her cupped palm.

She held her hand there, staring at the warm, pearly fluid as your body shuddered and went still. “Oh,” she breathed. “It’s… warm.”

Maddie watched Nicky’s expression, then grinned. “Feed it to him.”

Nicky’s eyes widened. “What?”

“You heard me. It’s his own. Feed it to him. It’s part of the management—no waste.”

Nicky hesitated for only a second before bringing her cupped palm up to your mouth. “Here,” she said, her voice a mix of command and curiosity.

You leaned forward and obediently licked the warm, salty fluid from her hand, your tongue cleaning her palm thoroughly.

A giggle burst from Nicky’s lips—a light, surprised sound. “Oh my god. He really is like a little puppy. A very obedient little puppy.”

Emily slowly withdrew her finger, watching the scene with a satisfied nod. “Good. That’s the whole cycle. Maintenance complete, and no mess. And now he’s settled now.”

You lay on the rug, breathing heavily, awash in a deep, post‑coital calm. The ache was gone. The nervous energy was gone. You felt empty, sated, and profoundly at peace.

The girls moved around you, wiping their hands and your small penis with wash cloth, whispering to each other. You heard the click of the cage being locked back into place—the chaperone restored. The pink plastic was cool against your softened flesh.

“It’s almost eleven,” Maddie said, checking her phone.

Emily nodded. She came to stand over you. “Up you go. Time to get dressed in your outdoor things.”

You pushed yourself to your feet, your limbs loose and compliant. You pulled on your panties, fastened the corset, your pants, shirt, the ballet flats, your movements slow and precise.

“You did well tonight,” Emily said, her voice assuming a new authority. It wasn’t Ms. Hollaway’s deep certainty, but it was a credible echo. “We learned a lot. And you… you served your purpose.”

She handed you the brass key. “Take this back to Millie. Tell her… tell her the lesson was successful. We’ll be in touch about next steps.”

You took the key, your fingers closing around the warm metal.

“And one more thing,” Maddie added, her eyes gleaming with the thrill of their new project. “Tell her we’re thinking of expanding the laboratory. We might have some… new subjects in mind.”

You nodded, not trusting yourself to speak.

“Go on,” Emily said, gesturing to the door. “Don’t be late.”

You left the apartment, the door closing softly behind you. The hallway was quiet, the only sound the distant hum of the city.

As you walked down the stairs, the cage a familiar presence, the girls’ voices seemed to follow you—not as a memory, but as a new layer of your reality.

They weren’t just girls anymore. They were becoming managers. And you were their first, but not their last, shared resource.

The walk back to the brownstone was cold, but inside, you were warm.

This is the ninth in a series about a young man, his exacting employer, and the training he needs to anticipate a woman's every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service | The Office: Part V - The Date | The Office: Part VI - The Chaperone The Office: Part VII - The Pussy & the Floor | The Office: Part VIII - The Seminar

The Office: Part X — The Installation

The following Saturday afternoon, the parlor of the brownstone felt different. It was no longer a seminar for three curious girls. It was a laboratory ready for full‑scale operation.

You stood at your usual place in the center of the room, dressed in the uniform of your condition: the navy microfiber panties, the pink cage, the corset laced snug. But you were not alone.

On the settee, Emily, Maddie, and Nicky sat, their postures straighter, their expressions a blend of nervous excitement and focused intent. And beside them, on three straight‑backed chairs brought in from the dining room, sat Jason, Ben, and Leo.

You recognized them from the girls’ descriptions, now made flesh. Jason, from Nicky’s econ group, wiry and pale, his knees pressed tightly together. Ben from the library, with his thick‑framed glasses, blinking rapidly.

Leo, Maddie’s cousin’s friend, broad‑shouldered but hunched, as if trying to make himself smaller. They were all dressed in simple cotton briefs—white, grey, navy—but you knew, as everyone in the room knew, what lay beneath. Their anxiety was a scent in the air, sharp and familiar.

Ms. Hollaway stood before the fireplace, surveying her audience. She wore a simple charcoal‑grey dress, her demeanor one of calm, expansive certainty.

“Good afternoon,” she began, her voice warm and welcoming. “Emily, Maddie, Nicky—you’ve done excellent preparatory work. And Jason, Ben, Leo… welcome. There is no need for nerves. You are here because you share a configuration. A configuration that the world misunderstands, and that causes you considerable distress. Today, that ends.”

She paced slowly, her eyes moving from one boy to the next. “You have been measured. You have been fitted with chastity devices appropriate to your dimensions. You are wearing them now.”

It was not a question. A faint, collective flush crept up three necks. “This is not a humiliation. It is an honest assessment. Your penises are small. They are ornamental. They are charming, responsive indicator lights. But they are not, and will never be, functional tools for penetrating a woman.”

She let the statement hang, factual and unassailable. “This reality has made you anxious. Eager to please. Terrified of discovery. You have attempted to be boyfriends and failed, because you were trying to operate machinery you were not built to operate. You have carried what we call the operator’s burden, and it has exhausted you.”

Jason’s head bowed. Ben stared at his hands. Leo let out a slow, shaky breath. It was the sound of a truth, long suspected, finally spoken aloud without judgment.

“Relief is available,” Ms. Hollaway continued, her tone softening into a promise. “The burden can be permanently discharged. Your bodies have another utility, one perfectly suited to your wiring. A utility that provides profound pleasure, deep satisfaction, and, most importantly, a permanent place in a care structure that asks nothing of you but your receptive being.”

She turned her gaze to you. “My assistant will serve as the demonstration model. What you will witness is not a performance. It is an installation. He is about to become fully operational.”

She gestured, and Emily stood up, carrying a small, polished wooden box. She brought it to Ms. Hollaway, who opened it. Inside, on a bed of velvet, lay a harness of rich, dark leather, and a silicone dildo of modest, thoughtful proportions—pale pink, smooth, with a gentle curve.

“Emily, if you would,” Ms. Hollaway said.

With practiced hands, Emily helped her step into the harness and secure it. The process was methodical, quiet. The girls watched, absorbing every step. The new boys watched, their eyes wide, their breathing shallow.

Ms. Hollaway fastened the final buckle and then turned to you. “Come here, dear. On the chaise, on your hands and knees.”

You moved to the low, padded chaise longue and assumed the position. The leather was cool against your knees and palms.

“Observe,” Ms. Hollaway said to the room. She took a bottle of lubricant from the box and warmed a generous amount in her hands. “The preparation is important. It is a caring act.” Her slick hands smoothed over your cheeks, then her fingers found your entrance. “This is not his anus. This is his pussy. It is the functional center of his redesigned sexuality. It is made to be opened, filled, and used to deliver his pleasure.”

Her finger slid inside, easily, finding the prostate immediately. A soft groan escaped you. “You see? His body recognizes its purpose. His little penis is already straining in its cage. That is the indicator light confirming the system is ready.”

She withdrew her finger and picked up the dildo, locking it into the harness with a soft click. She applied more lubricant, coating the silicone thoroughly.

“The first penetration is a claiming,” she explained, her voice a low, steady lecture. “It is the moment the configuration is made physically real. There will be a stretch. There may be discomfort. But when done with care and certainty, the discomfort is subsumed by the profound psychological relief of being fit to purpose.”

She positioned herself behind you, one hand resting on the small of your back. “Breathe out, dear.”

You exhaled, and she pressed forward.

The sensation was immense—a slow, inexorable fullness that burned for a moment at the stretch, then gave way to a deep, spreading pressure. She did not stop, did not hesitate. She slid forward until the harness met your skin, until you were fully impaled. A choked sound, half‑pain, half‑overwhelmed relief, left your lips.

“Good,” she murmured, her hand stroking your back. “Very good. The barrier is gone. You are open.” She held still, letting your pussy adjust, letting the room absorb the sight. “Now, watch his spine. Watch his shoulders.”

She began to move, slow, deep, rhythmic strokes. The curve of the toy pressed relentlessly against your prostate with each inward motion. Pleasure, sharp and bright, began to spark deep inside, building with each pass.

“His pleasure is now entirely internal, and entirely controlled by the woman wearing the harness,” Ms. Hollaway narrated, her own breathing even. “He has zero operational responsibility. His only task is to receive. To feel. His orgasm will be milked from him; he will not take it. This is the permanent discharge from the operator’s burden.”

You could no longer hold the position. Your arms gave out, and you collapsed onto your forearms, your face pressed into the leather. The thrusts continued, unwavering, each one driving the pleasure higher. You were babbling, a stream of broken “thank you”s and “yes”s, your cock aching and dribbling uselessly in its cage.

“He is approaching completion,” Ms. Hollaway announced. She reached around your hip, her fingers finding the base of the cage. With a deft motion, she unlocked it and pulled it away. Your freed erection, rock‑hard and leaking, bobbed against your stomach. “Observe the emission. It will be a seepage, not a projection. A surrender.”

She increased her pace slightly, the sound of the harness a soft, rhythmic creak in the silent room. The pressure inside you coiled, tightened, and then broke.

You came without a single stroke to your cock. It was a deep, internal pulsing that seemed to pull the orgasm up from your core. Your penis twitched against your belly, and seed spilled out in a few weak, continuous runnels, pooling on the leather beneath you. It was less an ejaculation than a draining. A milking.

Ms. Hollaway slowed, then stilled, remaining seated deep within you for a long moment before gently withdrawing. The emptiness she left behind felt vast, and significant.

She straightened, unfastened the harness, and handed it and the dildo to Emily. Then she placed a warm hand between your shoulder blades. “The installation is complete. You are now a fully operational resource. Rest.”

You lay there, boneless, swimming in a sea of perfect, spent peace.

Ms. Hollaway turned to the three girls and their three boys. The boys were staring, their faces pale, their expressions a turmoil of fear and awe and desperate want.

“Your resources are ready,” she said to the girls, her voice now purely instructional. “The theory is understood. The demonstration is complete. You will now perform the installation yourselves. Emily, you may begin with Jason. Maddie, with Ben. Nicky, with Leo. Use the harnesses in the box. Be slow. Be certain. Speak to them. Tell them what is happening. Their relief is in your hands.”

There was a moment of stillness. Then Emily stood, took Jason’s hand—he flinched, then clung to it—and led him to the open space on the rug. Maddie and Nicky followed with their charges.

For the next hour, the parlor was a quiet workshop of transformation. Soft instructions layered over hitched breaths. “Breathe out, Jason.” “It’s okay, Ben, just let it happen.” “This is your pussy now, Leo. I’m going to take care of it.”

The sounds were the same: the click of harnesses, the soft slick sounds of lubrication, the sharp intakes of breath giving way to low, shuddering moans. One by one, the boys were opened, claimed, and milked. Their releases were the same quiet seepages, their bodies going limp afterwards in the arms of the girls who now owned them.

Ms. Hollaway moved from pair to pair, a quiet consultant, adjusting an angle, murmuring encouragement. “Well done, Maddie. You’ve found his button.” “Good, Nicky. See how calm he is now? The anxiety is gone.”

When it was over, the three new boys lay on the rug, each with his head in a girl’s lap, each looking dazed and profoundly peaceful. The air smelled of sex and lube and a new, settled calm.

Ms. Hollaway surveyed her laboratory. Six resources. Three managers. A fully realized configuration.

“The seminar is now concluded,” she said, her voice filled with a deep, satisfied warmth. “The laboratory is operational. You have your schedules. You have your rules. You have your shared resources. Go and live in the relief you have built.”

Emily looked up at her, Jason’s head heavy in her lap. “Thank you, Millie.”

“You are welcome, dear.” Ms. Hollaway’s eyes found you, still resting on the chaise. “The office will be open on Monday. Business as usual.”

And it would be. But nothing would ever be the same.

This is the final post in a series about a young man, his exacting employer, and the training he needs to anticipate a woman's every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service | The Office: Part V - The Date | The Office: Part VI - The Chaperone The Office: Part VII - The Pussy & the Floor | The Office: Part VIII - The Seminar | The Office: Part IX - The Laboratory

The Office: Part VIII — The Seminar

Emily arrived at the brownstone the following Thursday afternoon, not for a date, but for a consultation. Over tea in the parlor, her words were hesitant but clear.

“Ms. Hollaway… after the other night… I couldn’t stop thinking about it. About what you said. About his small penis. About managing him. And I told my two best friends, Maddie and Nicky. They were shocked, but… they’re curious. They want to learn more.”

Ms. Hollaway set her cup down, her gaze assessing. “My friends call me Millie, Emily. You may use it.”

She let the permission settle, watching the girl’s reaction. “Now, tell me. You’ve shared this with your friends. Are you prepared to share him? A boy with his configuration isn’t a boyfriend to be kept. He’s more like… a very attentive puppy, or a girlfriend who does exactly what you say. Are you and your friends willing to treat him as a shared project?”

Emily’s cheeks flushed, but she met Ms. Hollaway’s eyes.

“Yes,” she said, her voice firming. “That’s… that’s what we talked about. He’s not a normal boy, is he. Trying to date him would be weird. But as a… a shared resource? Something we learn to manage together? That makes sense. He's so attentive. So responsive. Maddie said he’d be like a communal boyfriend. Nicky said he’d be like a living… sex doll.”

Ms. Hollaway smiled, a warm, approving expression. “A shared resource. That is precisely the correct phrase, Emily. A boy with a small, responsive penis isn’t a romantic partner; he’s a utility. His attention is the commodity. His configuration makes him unsuited for exclusive ownership. He's not a boyfriend. He’s penis is designed to be managed, and management is more effective—and more satisfying for him—when it’s consistent and communal. You and your friends are thinking very clearly about this.”

Emily leaned forward, her hands clasped tightly in her lap. “Millie… would you be willing to teach us? Me, Maddie, and Nicky? How to… manage him? How to make him as attentive for us as he is for you? I want to learn to do it properly.”

A slow, warm smile spread across Ms. Hollaway's face. It was the smile of a master craftsperson finding a promising apprentice. “That is a very sensible request. Bring your friends here on Saturday afternoon. We’ll have a seminar. He will be our teaching aid.”

Saturday.

Maddie and Nicky and Emily sat on the settee, three ordinary girls in jeans and sweaters, trying not to stare as you stood at attention in the center of the room in your panties and corset.

“Girls, this is what we’re working with,” Ms. Hollaway began, her voice calm and instructional. She walked a slow circle around you. “Note his posture. His corset isn’t just for aesthetics. It prevents slouching, which is a physical manifestation of a wandering mind. It keeps him present.”

She stopped in front of you. “Turn around, dear. Show them your packaging.”

You did a spin, displaying the navy microfiber panties.

“These aren’t a fetish,” she explained to the wide-eyed girls. “They’re honest tailoring. They fit the anatomy he actually has. Cotton boxers would bunch and chafe on a penis this small. These contain support his small equipment, and remind him of his place.”

Maddie, the bolder of the three, leaned forward. “Emily said there's a cage? She said you called it his chaperone?”

"Ah, yes. His pink guardian. Go fetch it for me, dear.” Ms. Hollaway said.

You shuffled out of the parlor and up the stairs, the silk of your panties whispering with each step. As you reached the upstairs hallway, their voices floated up from below—light, feminine, punctuated by soft giggles.

“…so he just stands there?” one of them—Maddie, you thought—asked.

“Until instructed,” Ms. Hollaway’s calm reply. “It’s part of the conditioning. He learns that his default state is readiness, not initiative.”

Another ripple of laughter, this one warmer, more intrigued.

You entered her bedroom, went to the vanity, and opened the top drawer. The pink cage lay there, waiting. You picked it up. The plastic was cool, smooth, familiar.

From downstairs, you heard Emily’s voice, clearer now: “And does he ever… you know… get to finish? Normally?”

Ms. Hollaway’s reply was calm, instructional. “Of course. He’s milked regularly. A prostate orgasm, hands-free. It’s more efficient for his wiring, and it prevents the buildup of tension that would make him distracted. He was milked just yesterday, in fact. But his little system refills quickly. The need isn’t a driver for him; it’s a manageable biological function, like emptying the bladder. We schedule it.”

There was a beat of silence, then Emily’s softer, hesitant murmur: “Oh. So you… I mean, he… takes it… there?”

“In his anus, yes,” Ms. Hollaway said, her tone unchanged, as if discussing a technical detail. “It’s not unlike a girl’s pussy, Emily. Very responsive to penetration. With proper stimulation, he can achieve a complete, satisfying release without his little penis being involved at all. It settles him beautifully.”

“Oh,” Emily said again, her voice a mix of shock and dawning comprehension. “So he doesn't use his… penis at all.”

“Precisely. You’re learning.”

You closed the drawer and turned back toward the door, the cage a small, humiliating weight in your palm. Their conversation continued, a soft murmur of female conspiracy you were no longer meant to hear.

You walked back into the parlor. The three girls on the settee fell silent, their eyes fixed on the pink plastic in your hand. You stopped in front of Ms. Hollaway and held it out to her.

“Thank you, dear,” she said, taking it. She held it up for the girls to see.

“The cage is for you, not for him. It’s a chaperone. It ensures that when he is in your company, his little friend cannot become a distraction. His attention remains on your comfort, not on his own biological noise. Now, observe. The fitting is a ritual. It reinforces the transition from private management to public service. Come here.”

You stepped closer. She knelt before you, and the room watched. She fitted it on you then and there, locking it with a soft click. “See? Neat. Contained. No surprises.”

Nicky, quieter, spoke up. “How… how did you learn all this?”

Ms. Hollaway's expression softened, becoming almost nostalgic. “My first husband, Arthur, God rest him, was a traditional man. Very adequate. But my younger brother, Stephen… he was built like my assistant. Anxious, eager to please, perpetually overwhelmed by his own responsiveness. I watched him struggle for years, trying to be what he wasn’t. He dated lovely girls, and they’d inevitably leave, confused and unsatisfied. He was heartbroken each time, but he couldn’t see the root cause.”

She paused, her gaze drifting to you, as if seeing a younger version of her brother in your stance.

“One summer, he came to stay with me after a particularly bad breakup. He was despondent. I decided to be… thorough in my care. I helped him with his laundry. And there, in the wash, I saw his underwear. The… patterning. The way it was shaped. I confronted him, gently. He broke down and confessed. He was, as I suspected, very small. Not just in confidence, but in actual, physical fact.”

The room was utterly silent. Maddie’s mouth was slightly open. Emily leaned forward, rapt.

“That was the key,” Ms. Hollaway continued, her voice warm with the memory of a puzzle solved. “The anxiety, the eagerness to please, the responsiveness—it wasn’t just personality. It was the somatic reality of a penis that was ornamental, not functional. It was a cute, twitching accessory, not a tool for penetration. Once I understood that, everything became clear. He didn’t need pep talks. He needed management. Structure. So I began to structure things for him. Schedules. Clear instructions. And, yes, I took charge of his little penis as well.”

Nicky gasped, a hand flying to her mouth. “You… you didn’t.”

“I did,” Ms. Hollaway said, her tone leaving no room for doubt. “It was my duty. He was floundering. A man with a small penis is like a boat without a rudder; he needs a steady hand on the tiller. I provided that hand. I scheduled his releases. I taught him that his pleasure was secondary, derivative of my satisfaction with his obedience. I milked him regularly, of course. Prostate stimulation. It settled him, focused him. He thrived under direction. For the first time in his life, he was calm. Happy. He now lives with a woman who has taken on that duty. He's quite content.”

Emily’s eyes were wide. “So you… you milked your brother?”

“Yes, dear. Because that is how you manage a man with a small penis. The organ itself is decorative. It gets hard, it spurts, it’s charming in its way. But its true function is as an indicator light—it tells you when he’s responsive, when he needs attention. The real work of his satisfaction happens elsewhere. And it is a woman’s prerogative, and her duty, to manage that. To provide the structure he cannot generate for himself.”

Maddie, recovering from her shock, let out a nervous giggle. “Wow. So, like… no man is off limits? If he’s built that way?”

Ms. Hollaway gave a small, elegant shrug. “The station or status is irrelevant. A father, an uncle, a boss. If he has a small penis, he needs to be managed. The world is full of anxious, twitchy little men pretending to be something they’re not, making poor decisions and disappointing women because no one has had the clarity to take them in hand. I hope, if you learn nothing else from me, you learn never to shy away from that duty. See the need. Provide the structure. Everyone benefits.”

She let that settle in the quiet room. The girls looked at each other, then at you, then back at Ms. Hollaway. The shock in their eyes was slowly being replaced by a fascinated, serious consideration.

“This,” Ms. Hollaway said, gesturing to you with a calm sweep of her hand, “is simply a more refined, formalized application of that principle. He is not my brother. He is my assistant. But the underlying truth is the same. And now, you three will learn to apply it.”

For the next hour, you were a living prop. Ms. Hollaway had you pour tea, noting how you watched the cup, not the pourer’s face. She had you kneel, demonstrating how the position naturally lowered your gaze. She had Emily give you a simple command—“Fetch my bag, please”—and praised your immediate, silent compliance.

“His pleasure is derivative,” Ms. Hollaway explained. “It comes from your satisfaction. He doesn’t need to be stroked or praised like a pet dog. He needs to see you relaxed, happy, attended to. That is his reward.”

As the afternoon light faded, Ms. Hollaway clapped her hands together softly. “Theory is essential, but practice is mastery. Girls, take him to Emily’s apartment. Your project for the evening is to explore the primary function he is equipped for. He is to be your shared resource. Emily, you have seniority—you may direct the session. His mouth, however, is at your disposal.”

She held up the small brass key before placing it in Emily’s palm. “This is for the return journey. He should remain caged throughout your session. It maintains the necessary boundary. If, however, you wish to practice the milking technique we discussed—to experience managing his release directly—that will be your pedagogical decision. The key provides the option. Use it thoughtfully.”

She then turned to you, her gaze settling on you with finality. “You will go with them. You will listen. You will be attentive. Your function tonight is to be their learning aid. You will not speak unless instructed. You will not initiate. You will receive their instruction and you will comply. Your satisfaction is in their education. Is that understood?”

“Yes, Ms. Hollaway,” you said, your voice low.

“Good.” She gave a single, approving nod to the three girls. “Off you go, then. I expect a full report on your progress. And you,” she added, her eyes back on you, “be back by eleven. Do not make me wait.”

This is the eighth in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service | The Office: Part V - The Date | The Office: Part VI - The Chaperone | The Office: Part VII - The Pussy & the Floor

The Office: Part III— On the Job Training

The panties arrived in a discreet black box. Six pairs of microfiber, six of silk.

They fit as Anna had promised—snug, containing, presenting a smooth, unremarkable line. The light compression corset arrived two days later. It was a garment of subtle power: boned, laced up the back, it pulled your shoulders back and your stomach in, enforcing a posture of attentive stillness.

You wore them both without question. They were your uniform. The cotton boxers were gone, discarded as instructed. Your old self felt as distant as those wadded-up briefs in the trash.

A week after your fitting, Ms. Hollaway called you into her bedroom in the late afternoon. She was at her vanity, examining her reflection.

“We have a guest for dinner tonight. Richard is a partner at the firm. A gentleman.” She met your eyes in the mirror. “You will prepare me.”

“Of course. What would you like me to—”

“You will shave my legs. And my pubic area. You will select my lingerie and lay out options for me to consider. You will apply my perfume. You will dress me. This is part of your duties. Intimate care.”

Your mouth went dry. Your cock gave a twitch inside its silken pouch.

“I… I don’t have experience…”

“You will follow my instructions. That is the only experience required.” She stood and walked to the en suite bathroom. “Come. We’ll begin.”

The next hour was a lesson in focused, clinical intimacy.

You knelt on a towel beside the tub as she sat on its edge, one leg extended. You lathered, you shaved with a fresh, precise razor under her quiet guidance—“against the grain here, dear, more gently there.”

The act was so profoundly personal, yet her manner made it a procedure—a clinical intimacy that left you reeling.

When it came to her pubic area, she simply lay back on the towel, exposed, her knees bent and parted. “Just a neat trim. Follow the natural line.”

Your hands shook as you applied the cream, your fingers brushing the soft, dark curls. This was the first pussy you had ever seen up close—the soft, plump lips, the glistening pinkness revealed as you carefully moved the hair aside.

The scent of her, musky and clean and overwhelmingly her, filled your head, a scent you knew would be imprinted on you forever.

The warmth of her skin radiated against your knuckles. Once, as you adjusted your angle, the back of your hand brushed against the full, heavy weight of her breast where it rested against her side.

You completed the task with trembling precision, your face burning, your body humming with a confused, desperate arousal.

Your cock, trapped in the silk of your new panties, was a hard, aching line against your stomach, throbbing in time with your frantic heartbeat.

She had to see it. She had to know. But she said nothing, only watched your progress with that calm, assessing gaze, as if your erection was merely another piece of data in the experiment.

After her shower, she stood in a robe while you laid out three lingerie sets on the bed.

She pointed to a black lace bra and matching panties. “That one.”

You helped her into them, your fingers fumbling with tiny hooks and delicate straps. She then selected a slip dress. You held it for her as she stepped in, then zipped it up the back, your knuckles brushing her spine.

Finally, the perfume. She had you apply it to her wrists, behind her ears, and—at her instruction—a single drop in her cleavage. “A man should discover it, not be assaulted by it,” she explained.

You were putting away the shaving supplies when she said, “There is one more preparation. For you.”

She led you back to the bathroom. “Remove your trousers and your panties.”

You obeyed, stepping out of them, standing naked from the waist down except for the corset.

“Now,” she said, leaning against the sink, her arms crossed. “We need to address a practical issue. In my experience, men with your… configuration often become overwhelmed in situations like tonight. The anticipation, the proximity, the service—it floods your little system. Your little friend gets ideas above his station. He becomes a distraction. For you, and for me.”

She paused, letting the clinical assessment settle. “I understand the problem. It’s a physiological response, not a moral failing. But it is a problem that requires management. And I have learned that men with little penises need to be managed. Supervised. Watched. So, here is the solution.”

She nodded toward the toilet. “Take yourself in hand and masturbate to completion. Into the bowl, please. Empty your testicles. I will watch to ensure it’s done properly. Consider it a necessary maintenance procedure, like letting steam out of a boiling pot. Once you’ve relieved that pressure, you’ll be calm. You’ll be contained. And you’ll be able to perform your duties without your… anatomy interfering with your purpose.”

As if on cue, as she spoke the words your anatomy interfering, you felt a telltale thickening, a slight lift against the fabric of your panties. Her eyes, ever observant, dropped to the movement.

“You see?” she said, a note of quiet vindication in her voice. “The system is already overloading. The proof is right there. Go on, then. Take yourself in hand. Into the toilet, please. Be quick about it.”

The command was so blunt, so utterly devoid of eroticism, that for a moment you just stared. This was maintenance. Emptying your balls into the bowl so it wouldn’t cause trouble later.

“Ms. Hollaway, I don’t know if I can just…”

“You can. And you will.” Her voice was low, instructional, but with a patient, almost maternal cadence. “I’ll talk you through it. It’s not a complicated process, dear. A boy’s penis is a simple thing. It gets hard, it spurts, it goes soft. You know this. You do it all the time, don’t you?”

She paused, waiting for the confession. You gave a tiny, shame-filled nod.

“I thought so. I can always tell. The chronic ones have a certain look. We’ll address that habit later. For now, let’s focus on the task. Take yourself in hand. Just like you do in your room. Thumb and forefinger, a gentle circle. Not too tight. You’re not punishing it. You’re just… guiding it toward its purpose. Now, a steady rhythm. Up and down. There. See? You know how. You’ve had plenty of practice.”

Her voice softened, taking on a patient, instructive tone. “Now, if we’re going to do this, we should do it properly. I’m going to talk you through it, step by step. It’s important you understand what’s happening. Keep humping while I talk.”

You obeyed, your movements clumsy under her gaze.

“Good. Now, what we are doing is training your penis.” Her voice remained soft but shifted into a tone of deliberate instruction, the same one she used when explaining a new household protocol.

“It’s the next step in your conditioning. Just as we corrected your focus with correction, your posture with the corset, and contained your shape with the panties, I will now condition your arousal. Your penis must be as responsive to me as the rest of you.”

She watched your hand, your hesitant grip. “Your penis is currently untrained. It fires at random stimuli—fantasies, memories, anxieties. That is inefficient. It leads to distraction. We are going to pair it with a specific, authorized stimulus. Me. My image. My breasts. My vagina. All the data you collected today.”

She leaned slightly closer, her gaze holding yours. “From this moment forward, your penis will learn to associate its function with me. The sight of my vagina. My pubic hair. The feel of my skin under the razor. The curve of my hip in the dress. The scent you applied to my wrists. These are now the exclusive triggers for your penis and for your arousal. We are wiring that in. Now.”

She nodded toward your hand. “Keeping humping into your hand. Good. Every pump is a reinforcement. You are not just masturbating. You are programming. You are teaching your penis what he is for. Who he belongs to. Back and forth. Good. Keep going. Deeper. Yes. You are a quick study. I can see the connection forming. Your penis is accepting the new programming. Good boy.”

She paused, letting the clinical analysis settle. You continued humping, slowly, rocking your hips back and forth, mesmerized by her voice.

“Good. Now, I want you to close your eyes,” she instructed. “Close them. Good boy. Now, picture the razor in your hand. The sound it made against my skin. The warmth of my thigh under your palm. The sight of my vulva as you moved the razor along. Hold that image. Let it fill your mind. That is your stimulus. That is your permission.”

Your breathing grew heavier. The image was vivid, immediate.

“Your little penis is responding,” she observed, her voice calm. “He recognizes the data. He’s making the connection. Faster now. Hump faster into your hand. Match the rhythm of the razor. Short, precise strokes. Yes. Just like that.”

You increased your pace, the friction building, your hips pistoning in a shallow, obedient rhythm.

“Now, add another layer. The scent. The perfume on your fingers after you applied it to my wrists. The clean, floral scent of my skin after the shower. Breathe it in. Let it be part of the circuit. Your arousal is a circuit, and we are wiring it together. My image. My scent. My voice. They are the switches. Your penis is the light. And I am turning it on.”

A soft groan escaped you. The sensations were coalescing, focused entirely by her narration.

“You’re approaching threshold. I can see the tension in your abdomen. The flush on your neck. Your testicles are drawing up. These are the signs. They mean the programming is taking. Your penis is accepting the new protocol. Now, I want you to add in your mantra. A vocal cue to go with the smell and the image. I want you to say ‘I am training my penis for you.’”

The words felt thick, absurd, but you forced them out between gasps. “I am… training my penis… for you.”

“Again.”

“I am training my penis for you.”

“Good. And who does your penis belong to?”

“It… it belongs to you.”

"Say it properly and keep humping. Back and forth."

"My penis belongs to you."

“Good. And what are you doing right now?”

“I'm training my penis for you.”

"Good boy. Keep going. Keep humping. Keep repeating it out loud with each thrust."

"I'm training my penis for you."

“Good. Breathe in,” she commanded, bringing her wrist to your nose. The jasmine and sandalwood scent flooded your senses. “Now speak on the exhale. Move your hips through your fingers as you do. Back and forth. Back and forth.”

You rocked your hips, your penis moving in and out of the loop of your fingers.

“Good boy. Now Again. Inhale. My scent in, your mantra out.”

You inhaled deeply, the perfume dizzying. “I’m training my penis for you.”

“Good. Keep the rhythm. Don’t rush it. I control the tempo. In… and out… and in… and out…”

Your hips moved to her metronome voice. The words tumbling out of your mouth with each thrust. “I’m training my penis for you.”

“Deeper breath. Fill your lungs with me. That’s my scent in your body. That’s your trigger. Your everything. Hips humping. Scent in. Mantra out. In… and out…”

“I’m training my penis for you.”

“Faster now. One-and-two, and one-and-two. Match it. Say it.”

Your hips pistoned, your breath coming in ragged sync. “I’mtrainingmypenisforyou.”

“Clearer. Enunciate. You are training your penis. One and two and one and two.”

“I. Am. Training. My. Penis. For. You.”

“Again. With conviction.”

“I AM TRAINING MY PENIS FOR YOU.”

"Yes, you are. Your penis is learning. With each thrust and each breath, you are programming it to respond to me. To attune to me. Don't stop. Keep going. One-and-two, and in and out."

Your pace increased, the pleasure coiling tight. She watched, her voice a calm narration in the perfumed air. “I can see your testicles, dear. Drawn up tight against your body. Congested. Full. They’re ready for me. Ready to complete your training.”

Your thrusting was urgent now, on the edge.

“Stop,” she said.

Your hand froze. Your hips stuttered to a halt. The need was a live wire in your gut.

“Listen to me carefully. From this moment on, you are never to release without my permission. Your penis now belongs to me. It is a training instrument. And release is a function that is now under my management. Do you understand?”

“Yes, Ms. Hollaway.”

“Good. Now, you are at the threshold. You need permission. Would you like my permission?”

The question hung in the perfumed air. You were aching, straining, hovering on the edge.

“Yes,” you begged. “Please.”

“Ask properly.”

“Please, Ms. Hollaway. Please give me permission.”

“Permission to what, dear?” Her voice was cool, expectant.

“To… to cum,” you gasped, the crude word feeling alien in the formal space of her bathroom.

“We use precise language here. You are not a child. You are asking for permission to ejaculate. To complete the training exercise with a controlled release. Say it.”

“Permission… permission to ejaculate.”

“Speak the full request.”

“Please, Ms. Hollaway. Please give me permission to ejaculate.”

“Very well. You have my permission to reach ejaculation. To complete the training exercise. Aim your penis toward the bowl. Do not miss. This is a controlled procedure."

Her hand returned, bringing her perfumed wrist back beneath your nose. “Breathe in. Deeply. Just like before. Let my smell into your body. Let it be the cue for your arousal, the thing you smell with each thrust as you obey.”

You inhaled, the scent flooding your head.

“Now, begin again. The cadence. The mantra. One. Two.”

Your hips, which had stilled, jerked back into motion. “I’m training my penis for you.”

“One. Two. Breathe in on one. Out on two. My scent in, your purpose out.”

“I’m training my penis for you.”

“One. Two. Keep the rhythm. Your penis is red now, dear. Swollen. I can see the vein throbbing along the shaft. It’s learning. It’s responding to the programming. Breathe in. My scent. Out. Your purpose.”

You inhaled, the scent now inseparable from the building pressure. Your thrusts were losing their measured pace, becoming shallow, frantic bucks. “I’m training my— ah— for you.”

“I can see your testicles are a hard, aching knot. They’re pulled up so tight they’re almost disappearing. That’s the training. Attuned to my voice. The signal of your arousal. The coding taking hold. Your penis primed and ready. But it only fires for me. Say it.”

“It only fires for you,” you gasped, your voice breaking.

“Again. And keep humping. Don’t you dare stop.”

“It only fires for you! It only fires for you!”

“Your control is slipping. I can see it. Your hips are jerking. Your hand is a frantic piston. The head of your penis is purple, slick. You’re at the absolute limit. The pot is boiling. One more breath. In.”

You sucked in a ragged breath, your whole body trembling on the precipice.

“Now. Use your words. Ask me for permission.”

“Please! Please Ms. Hollaway, please let me cum!”

“Good," she said. Her voice calm. Quiet. Soothing. "You may ejaculate, now. Execute.”

With a choked cry, you obeyed, you erupted, your semen arcing into the toilet bowl in several frantic spurts. Your body shuddered through the contractions, your hips still humping feebly into your fist until the last weak drop was spent.

She watched, patient and assessing, until the last shudder passed through you.

“Well done,” she said, her tone one of professional satisfaction. “A successful first training session. You followed the protocol. You used the correct stimuli. You requested permission. You contained the result. This is the standard. This is how I will manage your penis from now on. Do you understand?”

You stood there, panting, slumped against the toilet, spent and hollow. You could only nod, your energy utterly drained.

“Verbal confirmation, please.”

“Yes, Ms. Hollaway,” you whispered.

“Good. Clean yourself up, dear. Then we will proceed with the next step.”

To be continued….

This is the third in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress

The Office: Part VI — The Chaperone

Emily stood in the foyer, coat folded neatly over her arm, eyes wide with soft, bewildered surprise.

She had expected a brief introduction or perhaps a quick chat before your date. She had not expected the hushed elegance of the brownstone or you standing one precise step behind Ms. Hollaway, posture held unnaturally straight by the corset beneath your suit.

“Emily, dear, come in,” Ms. Hollaway said, her voice warm and welcoming as she took the coat with graceful hands. “Thank you so much for coming on such short notice. I’m Mildred Hollaway. My assistant has told me how kind you were with my dry cleaning.”

“It’s… nice to meet you,” Emily replied, her gaze flickering repeatedly to you. You managed only a small, helpless nod.

“Let’s sit in the parlor. I’ve asked my assistant to prepare tea.”

You moved ahead of them, the familiar rituals grounding you even as your heart hammered.

You poured the Earl Grey with exacting care—four minutes steeped, one sugar for Ms. Hollaway, none for Emily—then stepped back and waited at attention by the sideboard.

Emily watched every movement. The precision. The deference. She said little at first, but her cheeks held a faint, persistent flush.

Ms. Hollaway made pleasant, disarming conversation for nearly fifteen minutes, asking about Emily’s work at the dry cleaner, her evening classes, her family. She was intelligent, kind, and utterly at ease. Slowly, Emily began to relax.

Only when the girl had taken a second sip of tea did Ms. Hollaway set her own cup down with gentle finality.

“You seem like a very sensible, sweet girl,” she said. “Which is why I wanted to be completely transparent about our household arrangement. My assistant was quite eager to see you tonight. However, given his particular configuration, I felt a chaperone was necessary. For your comfort as much as his focus.”

Emily blinked. “A… chaperone?”

“In a manner of speaking.” Ms. Hollaway turned to you with calm certainty. “Dear, fetch your pink guardian from the top drawer of my vanity.”

Your stomach dropped, but you obeyed without hesitation. When you returned holding the small shell-pink chastity cage in your palm, Emily’s eyes widened.

Ms. Hollaway took it and held it up so Emily could see clearly. “This isn’t punishment, Emily. It’s simple management. His little penis is charmingly responsive—almost sweetly so—but it has a tendency to become distracted at the most inconvenient moments. Tonight we want his full attention on ensuring you have a pleasant evening.”

Emily’s face had gone a deep, fascinated pink. She stared at the cage, then at you, then back at Ms. Hollaway, but she didn’t speak.

“Trousers and panties down to your knees, dear,” Ms. Hollaway instructed, her tone warm and matter-of-fact.

You obeyed under both women’s gazes. The cool air of the parlor brushed against your exposed skin. Your soft penis twitched visibly, beginning to thicken the moment it was seen.

Ms. Hollaway made a soft, knowing sound. “You see? Already trying to perform for Emily. That’s precisely why we need this.”

She knelt gracefully in front of you and fitted the ring of the cage around the base of your scrotum. Her cool fingers brushed your skin, sending another involuntary throb through you.

“Poor thing,” she murmured affectionately. “Look how quickly he responds, Emily. Quite small when soft, and he struggles to stay that way. The cage will keep everything neat, contained, and properly behaved.”

She kept her fingers wrapped gently but firmly around the base of your shaft, holding you steady as the ring settled into place. A clear bead of pre-cum had already formed at the tip of your cock.

She paused, her expression one of gentle, diagnostic concern. “His little friend was thoroughly milked just this afternoon, of course. A complete, hands-free emptying of his testicles. But even so, he arouses again so quickly. It’s part of his particular wiring—always ready to respond, even when it’s utterly unnecessary.”

With a small, almost affectionate sigh, she collected the glistening drop of pre-cum on her fingertip and lifted it to your lips. “Clean that up, dear. We don’t want any mess before we lock him away.”

You obediently licked her finger clean under Emily’s wide-eyed gaze. The taste was faintly salty, familiar, and deeply humiliating. She released the ring and stood.

“Now, ice pack from the kitchen freezer and the numbing cream from my bathroom cabinet—the one with the blue label, dear. Bring both.”

You shuffled across the room with your trousers and silk panties around your ankles, returning with the items.

Under their combined, attentive gazes you pressed the wrapped ice pack firmly against your half-hard cock. The shock made you gasp. Emily watched, lips slightly parted, as the cold slowly defeated your arousal until you were completely soft and shrunken.

“Good boy,” Ms. Hollaway said approvingly. “Now the cream. A generous amount. We want you properly insulated from temptation this evening.”

She squeezed a thick dollop of the cool white cream into your palm and watched as you rubbed it thoroughly over your penis and scrotum. The tingling numbness spread quickly, creating a strange, distant sensation—as though your genitals were being wrapped in thick cotton wool.

Ms. Hollaway watched with satisfaction as you finished applying the cream. She turned her head slightly toward Emily, her tone one of mild, academic interest.

“Have you ever had to manage a boy with a penis this small, Emily?” she asked, as if inquiring about a household appliance.

Emily’s eyes widened, a faint blush rising on her cheeks. She gave a small, uncertain smile. “Manage?”

“Yes, manage,” Ms. Hollaway said, her voice warm and explanatory. “Their particular configuration requires external structure. Without it, they become anxious, distracted by biological impulses they aren’t equipped to act upon. Providing that structure is a form of care. It settles them.”

She paused, letting Emily absorb that. “His small penis is especially responsive. It’s a testament to how he is wired. The penis often confesses what the mind wishes to hide.”

She glanced back at your now-numb and shrunken penis, nodding slightly. “Excellent. Now we can finish.”

She knelt once more, fitted the pink cage over your penis, and clicked the small brass padlock shut. The sound was quiet but final.

“There,” she said, rising and dropping the key into the pocket of her skirt. She gave the locked pink package a gentle, proprietary pat.

“All managed. That will remain on until you return after your date. No distractions. No temptation. You will focus entirely on Emily’s comfort and pleasure tonight. You may get dressed now, dear."

You pulled up your silk panties and trousers, the cage now a silent, numb weight between your legs. The microfiber hugged the plastic securely, creating a smooth, unobtrusive line under your clothes.

Ms. Hollaway smiled warmly at Emily, who looked flushed and quietly mesmerized. “You may find him unusually attentive this evening. That is the point of his training. He is learning to put a woman’s needs first.”

She turned back to you, resting a hand lightly on your shoulder.

“Text me when you arrive at the theater and when you leave. Be back by eleven. And remember, dear—honest service. No pretending to be anything other than what you are. Emily deserves that honesty.”

You held the door for Emily. She stepped out into the cool evening air ahead of you. As you followed, Ms. Hollaway’s final gentle instruction drifted after you from the doorway:

“Have a pleasant time, both of you. I look forward to hearing all about it when you return.”

The pink cage sat cool and locked between your legs as you walked beside Emily into the night. Every step reminded you of the new boundary that had just been crossed.

The configuration was no longer confined to the brownstone.

This is the sixth in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service| The Office: Part V - The Date

The Office: Part VII — The Pussy & the Floor

The bar was quiet. You sat in a corner booth, the pink cage a quiet, persistent presence with every shift of your legs.You ordered a beer. She ordered a glass of wine.

At first you didn't speak. Emily didn't either. The silence was a thick, humming thing, filled with everything that had just happened in the parlor.

Then Emily gestured to a garish abstract painting on the wall behind you. "Looks like someone tried to paint a sunset blindfolded after a bender," she said. You both laughed, a sudden, genuine release that cut the tension between you.

Then, for nearly an hour, you talked about everything else. Her classes. A movie she'd seen. The weather. The bar's terrible decor. It was a careful, deliberate dance around the enormous fact of your pink chaperone.

She would glance at you, her eyes soft and curious, but she never asked. You never offered. It was easier this way. Almost normal.

When the clock on her phone showed 9:45, she set her glass down. "I should probably get you back soon. Your… curfew." The word felt strange in her mouth, but she wasn't being mean.

"I have time," you said, the words coming out before you could stop them.

She studied you for a long moment, her head tilted. "Do you want to come back to my place? For a nightcap? Before you have to go back."

Her voice was gentle, but there was an unmistakable intention in it. She wasn't just being polite. She was asking to see.

The walk to Emily’s apartment was silent except for the soft click of your shoes on the pavement and the faint, plastic rustle of the cage with each step.

Emily didn’t speak. She walked beside you, her arms wrapped around herself, but her silence wasn’t angry. It was thoughtful. Charged.

Her building was a modest walk-up. Her apartment was small, tidy, smelling of lavender and clean laundry. She closed the door, leaned against it, and looked at you.

Her earlier flustered confusion was gone, replaced by a quiet, focused curiosity.

“Take off your jacket,” she said. Her voice was soft, but it wasn’t a request.

You hung it on the back of a chair. She nodded toward your waist. “And the rest. I want to see it properly. Without… her watching.”

You unbuckled your belt, unzipped your trousers, and let them pool around your ankles. You hooked your thumbs in the waistband of your navy panties and pushed them down too. You stood before her in your socks, shirt, and tie, the pink cage a glaring declaration against your skin.

Emily stepped closer. She knelt, just as Ms. Hollaway had, but her movements were slower, more tentative.

She reached out and touched the plastic with one fingertip, tracing the curve of the cage. “It’s so small,” she murmured, not unkindly. “She was right though. It’s… your penis is cute.”

Her finger drifted lower, brushing the numb, cream-smeared skin of your scrotum. “Does it hurt?”

“No,” you whispered. “It just feels… distant.”

“Good.” She stood up. “Lie on the bed. On your back.”

You obeyed, settling onto her comforter. She stood at the foot of the bed, watching you for a long moment.

Then she began to undress. Not with seduction, but with a practical efficiency that reminded you, unnervingly, of Ms. Hollaway preparing for a fitting.

Her sweater, her jeans, her bra, her panties. She stood naked before you. Her body was lovely—soft curves, pale skin, a thatch of dark hair at the junction of her thighs.

She climbed onto the bed, straddling your chest. “She said you were learning to put a woman’s needs first,” Emily said, her voice low. “She said you were trained to be attentive. Show me.”

She shifted forward, lowering herself until her pussy was hovering just above your face. The scent of her—musky, clean, overwhelmingly female—filled your senses. You had been close to Ms. Hollaway's during the shaving, but that was clinical, visual. This was intimate, intense, the warm heat of her pussy radiating against your lips.

“Have you ever tasted a pussy before?” she asked, her voice soft but direct.

The question, in the quiet room, was devastating. You shook your head against the comforter. “No,” you whispered. “I’m… I’m a virgin.”

A slow, warm smile spread across her face. “Perfect,” she murmured. “I’ll be your first. Don’t worry, I’ll train you.” She shifted her hips slightly. “Now, go on. Stick out your tongue. I’ll tell you what I like.”

Your mouth watered instinctively. You lifted your head and tentatively pressed your mouth to her.

She gasped, a soft, surprised sound, and her hips settled more firmly against you. “Yes,” she breathed. “Like that.”

You had no technique, only desperate, worshipful attention. You licked and suckled her pussy, guided by her subtle movements, her quiet sighs.

Your world narrowed to the taste of her, the feel of her folds against your lips, the soft weight of her on your chest.

“A little higher,” she breathed, her hand guiding your head with gentle pressure. “Right there… yes. Use your tongue in slow circles… just like that… good boy.”

Your caged penis gave a feeble, numb throb, a ghost of an erection that went nowhere. It didn’t matter. This was what mattered. Her pleasure was a tangible thing you could feel building in the tension of her thighs, the catch in her breath.

“Don’t stop,” she moaned, her hands tangling in your hair, not guiding, just holding. “Just like that… oh, god…”

Her orgasm washed over her quietly, a series of soft tremors that made her clutch your head and cry out into the quiet room. She collapsed sideways, off your face, eventually resting her forehead on your sternum, breathing heavily.

After a long moment, she rolled off you and lay beside you, staring at the ceiling. “Okay,” she said softly. “Okay. I get it now.”

You lay there, your face wet, your body humming with a strange, serviceable pride.

“You should go back,” she said finally, sitting up. “She’ll be waiting.”

You dressed in silence. At the door, she stopped you with a hand on your arm. Her expression was thoughtful, almost tender.

“You can text me,” she said softly. “If she says it’s okay.” She paused, her eyes searching yours. “She was right you know. You are wonderfully attentive. I’d… I’d like to learn how to manage you properly. If she’s willing to teach me.”

There was no pity in her eyes now. Only a new, settled understanding, and a quiet, eager curiosity about the configuration she’d just become a part of.

Ms. Hollaway was in the study, reading, when you let yourself in. She looked up over her glasses. “Well? How was your evening?”

You gave a halting report. The walk. The apartment. The inspection. The service. Emily's request to learn more.

She listened, her expression neutral. When you finished, she set her book aside. “I see. And did you satisfy her?”

“Yes, Ms. Hollaway.”

A faint, approving smile touched her lips. “Good. That’s progress. You’re learning to use what you have.” She stood. “Now, the cage has served its purpose. Come here.”

You approached. She retrieved the key from her skirt pocket, knelt, and unlocked it.

The plastic fell away into her hand. Your penis, still smeared with dried numbing cream, was soft and small. She examined it for a moment, then patted it gently.

“All tucked in for the night. But I’ve been thinking, dear. It’s very late. And after an evening of such… stimulation, I’m not sure I trust you to go home alone. Your little friend might get ideas, even tired as he is.”

She stood and walked toward her bedroom, gesturing for you to follow. “You’ll sleep here tonight. On the floor at the foot of my bed. That way, if you wake up with any… urges, I’ll be right there to remind you of the rules.”

She took a spare blanket and a pillow from the linen closet and placed them on the Persian rug at the foot of her large four-poster bed. “Make yourself comfortable. The bathroom is through there if you need it. But no touching. Understood?”

“Yes, Ms. Hollaway.”

“Good. Sleep well, dear. We have a busy day tomorrow.”

You lay down on the rug, the blanket pulled up to your chin. The room was dark, fragrant with her perfume. You heard the soft rustle of her sheets as she settled into bed.

You were on the floor. A pet. A supervised boy. And as you drifted off, the last thought in your mind wasn’t shame. It was a deep, unsettling comfort. You were where you were supposed to be.

This is the seventh in a series about a young man, his exacting employer, and the training he needs to anticipate her every need.

Previously: The Office: Part I | The Office: Part II - Seamstress | The Office: Part III - On the Job Training | The Office: Part IV - Turn Down Service | The Office: Part V - The Date | The Office: Part VI - The Chaperone