Personalised Story: Klaudia & Roxanne: Part 4 (Patreon)

The next morning Tim arrived at the office early, dressed in his shirt, tie and trousers, his shoes polished to a dull shine. He moved quietly through the reception area, straightening papers, arranging files, and answering the phone in a soft, almost timid voice.

Every time the door to Klaudia’s inner office opened he glanced up with flushed cheeks, his gaze dropping quickly when she caught him looking. The steel cage around his cock felt heavier than the day before, a constant reminder that his body no longer belonged to him.

He answered every request with a quick “Yes, Miss,” and kept his hands clasped in front of his trousers to hide the way the cage tugged whenever his thoughts drifted.

Klaudia stayed behind her closed door until mid-morning. When she finally stepped out, the sight of her stopped Tim mid-sentence on the phone. She wore glossy black latex pants that clung like a second skin, the material stretched tight over the full curve of her ass and hips, every movement making the latex creak softly.

Above the waistband a sheer white top revealed the dark outline of her large breasts and the glint of the metal bars through her nipples. A delicate gold chain rested between those breasts, the two small chastity keys dangling and catching the light with every step. Her long blonde hair fell straight and shining over one shoulder, framing her full lips and the confident, slightly amused expression on her face.

Tim’s cock tried to swell inside the cage the instant he saw her. The metal bit into his flesh, turning the half-formed erection into a sharp, throbbing ache. He swallowed hard, eyes fixed on the keys, then on the way the latex hugged her thighs as she walked toward the reception desk.

“Fetch me a coffee,” she said, her voice calm and commanding. “Black, two sugars. And order lunch from the deli—my usual. Make sure it’s here by one.”

Tim’s mouth went dry. “Yes, Miss,” he answered at once, the words tumbling out before he could think. He set the phone down, cheeks burning, and hurried toward the small kitchenette. The cage pulled with every step, the trapped flesh straining uselessly against the unyielding steel.

By the time he reached the coffee machine his breathing had quickened and a thin line of precum had already begun to leak from the tip of the cage, darkening the front of his underwear.

He prepared the coffee exactly as she liked it, hands trembling slightly as he carried the mug back to her. Klaudia accepted it without comment, the keys on her necklace shifting and glinting as she leaned forward to take a sip.

Tim stood there a moment longer than necessary, unable to look away from the way the latex stretched over her ass when she turned to set the mug down. The ache in his locked cock grew sharper, the cage feeling smaller by the second.

“Anything else, Miss?” he asked, voice barely above a whisper.

Klaudia glanced over her shoulder, lips curving into a small, knowing smile. “Not yet. Keep busy. I’ll call you when I need you again.”

Tim nodded quickly and retreated to his desk, sitting down with careful movements so the cage wouldn’t pinch. He tried to focus on the filing, but every few seconds his eyes drifted back to the closed door, the image of those dangling keys and the tight black latex burned into his mind.

His cock throbbed helplessly inside its prison, leaking steadily, the wet spot in his underwear spreading. He shifted in his chair, cheeks still flushed, already counting the minutes until she would summon him again.

Tim balanced the paper bag and steaming coffee cup in both hands and rapped his knuckles softly against the office door. From inside came Klaudia’s smooth voice. “Enter, sweetie.”

He pushed the door open and stepped in, cheeks already pink. Klaudia sat behind her wide desk, legs crossed, the glossy black latex pants creaking faintly as she shifted. The sheer white top clung to her full breasts, the dark circles of her pierced nipples clearly visible through the fabric. The delicate chain around her neck swayed, the two small keys glinting against the white material.

“Leave them on my desk,” she said, nodding toward the polished wood.

Tim set the coffee and lunch bag down carefully, then straightened, hands clasped in front of his trousers. His eyes kept flicking to the keys. Klaudia noticed. She leaned back in her leather chair, one hand rising to toy with the chain, fingers sliding the keys back and forth between her fingertips. The motion made the metal click softly.

Tim’s cock tried to swell inside the cage again. The steel pinched, sending a sharp ache through his groin. A fresh bead of precum leaked from the tip, soaking into his underwear.

Klaudia watched him with a calm, knowing smile. “I was actually looking for a female secretary before Roxanne recommended you,” she said, voice casual. “You’re the only man in the office now.”

Tim’s blush deepened. He swallowed, wondering if this was the moment he would lose the job. Klaudia’s fingers kept playing with the keys.

“Would you be all right dressing a bit more feminine to fit in with the rest of the women?” she asked.

The question hit him like a spark. Sissification had always been one of his strongest, most secret fantasies. His locked cock throbbed violently, leaking steadily now, the front of his trousers growing damp. He shifted his weight, trying to hide the reaction.

“Yes, Miss,” he answered, voice small and quick.

Klaudia’s smile widened, bright and satisfied. She pointed to a large cardboard box sitting against the far wall. “Those are appropriate for the workplace. Make sure to wear each outfit in full. I won’t have someone changing the dress code without my permission.”

Tim glanced at the box, then back at her. “Yes, Miss.”

He walked over, lifted the surprisingly heavy box, and carried it out of the office. The cage tugged with every step, his cock straining uselessly, leaking into his underwear. He kept his eyes down, face burning, already imagining what the packages inside might contain.

The next morning Tim stood naked in front of his bed, the steel cage gleaming between his legs. The first outfit lay spread out across the sheets exactly as Klaudia had ordered: a tiny pink thong, matching pink bra, black suspenders, sheer black fishnet stockings, white trousers, a crisp white button-up shirt, a clear feminine blazer, and clear wedge-heeled women’s shoes.

He swallowed hard. His hands shook as he picked up the thong first. The thin pink fabric slid up his smooth, hairless thighs and settled snugly against his caged cock, the front panel barely containing the metal. Next came the bra; he fastened it behind his back, the cups pressing flat against his chest. The suspenders clipped to the stockings with soft clicks, the sheer mesh hugging every inch of his legs.

He stepped into the white trousers, the material clinging tight enough to show the faint outline of the thong and bra straps beneath. The white shirt followed, then the transparent blazer that did nothing to hide the feminine lines underneath. Finally he slipped his feet into the clear wedge shoes, the small heel lifting him slightly.

Tim turned to the mirror. The reflection made his face burn. The pink underwear showed clearly through the white layers, the bra straps visible at his shoulders, the stockings dark against his pale skin. A steady drip of precum leaked from the cage, soaking into the thong. He stood there blushing furiously, unable to look away from how completely feminine he appeared.

At the office he kept his head down, voice barely above a whisper whenever anyone spoke to him. Several of the women complimented the outfit, their eyes lingering on the sheer blazer and the faint pink lines beneath. Each comment sent a fresh throb through his locked cock, the cage biting down hard while fresh precum soaked the thong again.

Klaudia stepped out of her office wearing another skin-tight black latex catsuit, the glossy material stretched over her full breasts and thick ass. The two silver keys rested between her cleavage. She smiled at him.

“Tim, be a dear and run across the road for my coffee and lunch,” she said, voice smooth.

His eyes flicked to the keys nestled against her skin. He gulped, cheeks flaming, then nodded quickly. “Yes, Miss.”

He scurried out of the office, the wedge heels clicking on the floor, the white trousers hugging his ass and the cage aching with every step. The thought of walking into the busy café dressed like this made his stomach flip, yet his cock strained uselessly inside the steel, leaking steadily as he stepped outside into public view once more.

Tim hurried back across the street, cheeks burning hotter with every step. A pair of sharp whistles followed him from a group of men on the sidewalk. He kept his head down, wedge heels clicking, the white trousers hugging his caged cock and the faint pink lines of his underwear showing through. The whistles only made the steel bite tighter around his shaft, fresh precum soaking into the thong.

He reached the office, knocked once, and heard Klaudia’s calm voice call “Enter.”

Inside, he placed the coffee and lunch on her desk, hands trembling. She leaned back in her chair, fingers idly toying with the two silver keys nestled between her breasts. Her black latex catsuit gleamed under the office lights.

“Strip down to the outfit I gave you,” she said evenly. “I want to see that you’re wearing everything.”

Tim’s voice cracked. “Y-yes, Miss.” His fingers shook as he peeled off the transparent blazer, then the white shirt. He unfastened the trousers and let them fall, stepping out of the wedge shoes only long enough to slide the fabric free before slipping the heels back on.

Soon he stood in nothing but the pink bra, pink thong, black suspenders, and sheer fishnet stockings. The flat steel cage pressed visibly against the thin pink fabric, a wet spot already spreading at the tip.

Klaudia smiled. “Sit.”

He lowered himself into the chair opposite her, thighs pressed together, the stockings whispering against each other. She picked up her clipboard and pen, eyes drifting slowly over his exposed, trembling body.

Tim sat rigid in the chair, thighs squeezed tight, the sheer black fishnet whispering against his skin. His face burned crimson as Klaudia’s eyes roamed over every inch of him—the pink bra hugging his chest, the matching thong stretched over the flat steel cage, the suspenders framing his smooth legs. The keys to his cage rested between her full breasts, glinting every time she shifted.

She leaned forward, voice crisp and direct. “You look very pretty like this, Tim.”

The compliment hit him like a spark. Warmth flooded his chest even as shame twisted in his gut. His trapped cock gave a hard twitch inside the steel, forcing another thick bead of precum to seep through the pink fabric and darken it further.

Klaudia’s gaze dropped to the obvious wet spot. “You’re leaking quite a lot. Clearly turned on by the crossdressing.”

Tim swallowed hard, voice barely above a whisper. “Y-yes, Miss… it feels… really good. But I’m so embarrassed wearing this outside.”

She nodded, tapping her pen against the clipboard. “You just need to build confidence in your feminine self. The more you wear these things, the more natural it will feel. Soon you’ll start feeling sexy and confident instead of ashamed.”

She set the clipboard aside and smiled. “I have a solution for you. Roxanne—our mutual friend—is looking for help around her house. You can wear feminine clothes in the privacy of her home while you repay her for helping you get this job.”

Tim’s blush deepened, but he nodded quickly. “Yes, Miss.”

Klaudia’s smile widened, satisfied.

Roxanne reclined against the pillows in her bedroom, the deep red lace of her lingerie clinging to every curve. Her heavy breasts rose and fell with each slow breath, nipples stiff against the sheer cups. Between her spread thighs the matching panties were dark and slick, soaked through from the constant throb of anticipation that had been building all day.

Spread across the bed in front of her lay the outfit she had chosen: a short black satin maid dress with white frills, a matching lace apron, sheer black stockings, and a pair of glossy black heels. She reached out and ran her fingers over the smooth fabric, a slow smile curving her full lips.

"Finally," she murmured to herself, voice low and husky. "I’m going to have my own pretty little sissy maid. The daughter I never had… but so much better."

She pressed her thighs together, feeling another warm rush of wetness soak the already drenched lace. Her mind painted vivid pictures—Tim in that tiny dress, locked and leaking, curtsying awkwardly while she watched. She could already imagine the way his smooth thighs would tremble, the way the cage would strain against the soft pink panties she planned to keep him in.

Roxanne’s hand drifted down, slipping beneath the waistband of her panties to stroke her swollen clit in slow circles. A soft moan escaped her as she pictured him on his knees, lips painted, eyes wide with humiliated arousal while she gave him his first list of chores.

"You’re going to look so cute for me, sweetheart," she whispered, biting her lip. "And you’re never going to want to take that pretty outfit off."