Sissy Husband Gangbanged by Bailiffs

Caleb locked the glass door of his own office and stood in the Saturday hush, twenty-eight and finally alone with the craving his wife never saw. Nadia, twenty-nine, knew the contracts, the vendor dispute, the long hours. She did not know about the bag under the spare letterhead, or how his cock thickened the second the blinds were half-drawn and the suite was his.

He stripped. Black lace panties went on first, snug over his swelling cock. Sheer stockings rolled up his calves, clips snapping to the garter belt. The frilly black-and-white maid dress was short enough to be a plea; the skirt brushed his thighs and lifted when he breathed. He painted his mouth wet red, lined his eyes, and settled the blonde wig until the curls swung at his collarbones. Patent heels clicked when he turned before the dark monitor. The sissy in the glass was flushed and already leaking through the lace. He palmed himself once, shameless, hungry for a cock in his mouth and another in his ass before the afternoon died.

He had meant to spend the quiet hours bent over that desk with two fingers in his ass and his cock in his fist, moaning into the empty office like the slutty maid he only became when nobody could see. The wig tickled his neck. The heels made his calves ache in a way he loved. Precum had already soaked a coin-sized spot into the black lace, and he had been one good stroke from sitting on the blotter and finishing when her name flashed.

The phone lit with Nadia's name. He answered.

"Hey."

"Caleb, listen," she said, engine running under her voice. "Three male bailiffs are on their way to your office. Silas, Ambrose, and their colleague Dominic. They're serving the vendor papers. I tried to stall them. They're probably in your lobby."

His stomach dropped. His cock jumped so hard the lace tugged. "Now? Nadia, I'm—"

The suite door banged open.

Three men in dark jackets filled the threshold and went still. Caleb stood in heels and curls, phone at his ear, skirt twisted high over the garter straps and the damp panties clinging to his hard cock. Silas, thirty-two and tall, stared from the painted mouth to the wet lace. Ambrose, thirty-four, made a low sound. Dominic, thirty-five, broad through the shoulders, eased the door shut behind them.

"Papers can wait," Silas said, voice calm and thick with interest. "You look like you dressed up to be looked at."

Ambrose set his folder down without looking away from Caleb's thighs. "Slutty little uniform. Stockings. Heels. That blonde wig. You did all that on a Saturday and you want us to pretend we only came for a signature?"

Caleb's face burned, and the burn went straight to his cock. He should have hung up. He didn't. Nadia's breath waited in his ear, and the shame of that only made him harder.

"I—" His voice came out thin. Silas stepped close enough that Caleb smelled coffee and clean cotton, and hooked one finger under the skirt, lifting it an inch. Not grabbing. Asking, with his eyes as much as his hand.

"Pretty sissy," Silas said. "You want to play, or do you want us to serve these papers and leave you to finish alone in that cute little dress?"

Dominic's mouth curved. "Look at him. He's shaking and he's hard. That's not fear. That's a maid who got caught and likes it."

Caleb's knees softened in the heels. The truth was already soaking the lace. He kept the phone at his ear so Nadia would hear him, and he said it before shame could steal it.

"I'm incredibly turned on," he told her, breathy and wrecked. "Nadia, I'm standing here in the maid dress and I want them. I want all three of them to use me."

A beat, then her voice, lower than he had ever heard it. "Say it again so I know you mean it."

"I want them to fuck me," Caleb said, and his cock jerked at the honesty. "I'm dripping. I'm saying yes to all of it. I want you to hear how badly."

"I'm driving to the office," Nadia said. "I want to see my husband get what he's begging for. Leave the line open if you want me hearing you moan. I'm coming either way, and I'm already wet from your voice."

"Yes," he whispered. "Hear me. I want you to know."

Silas smiled like a man handed something he meant to enjoy. "She heard that. Good. Then everybody here wants it." His palm settled on Caleb's hip, warm through the thin dress, and Caleb pushed into the touch with a helpless sound. Ambrose dragged a thumb over the wet spot, slow, learning the cock straining under the lace. Dominic fit both hands to his waist from behind, thumbs stroking the garter belt, mouth near the blonde curls.

"Tell us," Ambrose said, rubbing until the lace squelched. "Out loud. Not just for her."

"Touch me," Caleb said. The words shook and meant themselves. "Please. I've been aching all afternoon. Use me. I want your cocks. I want to be your sissy fucktoy. I'm begging. I'm saying yes. You can stop if I say stop, and I am not saying stop."

They took him at his word. Silas kissed him deep, and Caleb moaned into it like a man who had finally been caught on purpose.

The kiss turned filthy, tongue sliding in until Caleb moaned and sucked, and Silas bit his lower lip and smiled when Caleb chased it. "Please," Caleb gasped. The phone sat live on the desk because he had put it there himself. "Please use me. All of you. I want it so bad I'm dripping through these panties."

"Get on your knees and show us that mouth," Silas said. "We'll take care of the rest. You say stop, we stop."

"I won't," Caleb said, and sank. The heels folded under him. He looked up at three hard cocks tenting dark pants and opened his mouth like the slut he had dressed to be.

Silas freed himself first, thick and flushed, precum shining at the slit. He tapped the head on Caleb's lips until Caleb licked it clean and moaned at the salt. "Open." Caleb opened. Silas slid over his tongue, slow, then deeper, until the head nudged his throat and his eyes watered. Caleb clutched Silas's thighs and pulled, begging for the rest of it.

"Good maid," Silas murmured, and throat-fucked him in steady strokes, one hand in the wig, guiding. Caleb sucked like he was starving. Cheeks hollowed. Spit shone on his chin and strung from lip to shaft. His throat worked every time Silas pressed in and held, and the wet sounds filled the quiet office.

Ambrose found the lube in the open bag. Caleb nodded frantically around the cock, a messy yes. Ambrose slicked two fingers, pushed the lace aside so the panties framed his hole, and pressed in. Caleb bore down and pushed back, whining around Silas, taking the fingers easy because he wanted them.

"Greedy sissy," Ambrose said, twisting deeper. "Desk. I want this maid bent over his own work while I pound him."

They bent him over the polished wood, skirt flipped to his waist, heels wide, cheek on a contract, cock dripping onto letterhead. Ambrose lined up, lubed and thick, and pushed into his ass in one long glide. Caleb cried out, high and grateful.

"Yes, fuck, fill me, don't go gentle—"

"Doggy," Ambrose said, and hauled his hips back, and then he was pounding, deep and even, the desk creaking, Caleb's ass clapping back to meet every stroke. Silas fed his cock between the painted lips again. They spit-roasted him, throat and hole taken at once, and Caleb drooled and shoved back and moaned yes, harder, please, the words broken around the shaft.

They rotated when Ambrose's grip turned shaky. Dominic took the ass, thicker, three slow strokes while Caleb adjusted, then harder once Caleb reached back and spread himself, hole shiny, begging. "Deeper. I can take your cock. Give it to me."

Silas dropped onto the leather sofa and pulled Caleb into his lap facing out, cock sliding back into the slick hole. Ambrose stood over them and fucked his willing mouth. Dominic stroked himself at Caleb's shoulder, heavy and flushed, the head bumping his cheek, waiting for that throat and watching the sissy bounce on Silas.

"Look at you," Dominic said, fist working. "Stuffed at both ends, wig crooked, mascara on your jaw. Our office fucktoy."

"I love it," Caleb gasped, pulling off just long enough to speak. "Don't stop. Use every hole. I want your loads in my throat and in my ass. Please. I'm so close just from being used."

They gave him the double he had begged for. Over the desk again, Ambrose buried in his ass, grinding deep, balls against the ruined lace, while Silas throat-fucked him until spit ran down the contract under his cheek. Dominic stood at his shoulder and stroked, smearing precum across Caleb's flushed skin whenever Silas pulled out to let him breathe. Then the sofa: Silas under him, Caleb riding that cock with his hole, Ambrose in his mouth, Dominic's slick fist at his lips so he could turn and suck the third between strokes. He serviced all three with desperate, slutty enthusiasm, lipstick gone, one stocking laddered, moaning every time a cock hit his throat or punched into his ass.

The first load came from Silas, buried in his ass, hips snapping, a rough groan, heat flooding deep. Caleb sobbed with pleasure and ground down to take every spurt, hole clenching, milking him. Ambrose hauled him off that cock, bent him over the sofa arm, and pushed into the creamy mess, fucking Silas's cum deeper while Caleb choked happily on Dominic's thick shaft. Dominic cupped the wig and came down his throat in heavy pulses. Caleb swallowed what he could and let the rest stripe his tongue and chin, showing them, filthy on purpose.

Ambrose finished in his ass with a hard grind, adding a second hot load, and pulled out so cum leaked over the lace and down Caleb's thigh. They were not done. Silas, hard again after a minute of Caleb's messy mouth cleaning him, took the throat while Dominic slid back into the sloppy hole and pounded him through the aftershocks. Caleb came untouched, cock jerking in the panties, striping the sofa, and he nodded with cum on his teeth and said more, please, more. Sweat darkened the maid dress. They rotated until each man had used his mouth and his ass, until loads sat in his throat and deeper in his hole, until his voice was hoarse from moaning their names.

The door opened because Nadia had a key.

She stopped in the frame and saw all of it: her husband in the wrecked maid dress, wig askew, face glazed with spit and cum, ass held open while Dominic fucked another load toward his sloppy hole, Silas in his mouth, Ambrose stroking and waiting to push back in. Caleb saw her and did not stop sucking. He moaned louder, a filthy welcome, and nodded so she would know he wanted her there.

Nadia's hand went under her waistband, no hesitation, fingers finding how wet the sight had made her. "Don't you dare stop on my account," she said, voice rough. "Finish in him. I want to watch my sissy husband take every drop."

They did. The final round was short, savage, and fully wanted. Dominic buried himself and came in the flooded hole. Silas came across Caleb's tongue and painted his lips. Ambrose pushed in last, used the mess, and added his own spurt deep while Caleb shook and came again into the lace, sobbing yes around the cock on his tongue.

Nadia crossed the room, grabbed the wig, and kissed the cum off his mouth, two fingers sliding into his leaking hole. "That made me so fucking wet," she said. "We're doing this again."

He pushed his ass back onto her fingers and whimpered for the next cock.

"Shove your cum-soaked tongue in my mouth and keep that sloppy hole open for the next cock."