Transsexual Wife Hires Sexy Ladyboy Maid for Husband's Fun

Roxanne adjusted the straps of her own lace teddy and smiled at the sight of her husband Benedict staring from the couch. At twenty-eight she had already planned every detail of this afternoon in their apartment, and the twenty-two-year-old ladyboy she had hired stood ready in the center of the living room. Heather’s French maid lingerie was barely there: a sheer black mini-skirt that flipped up at the slightest movement, a cropped bodice that left the undersides of her breasts bare, white thigh-high stockings clipped to a garter belt, and panties so small the outline of her cock and balls pressed visibly against the satin. The costume hugged every curve and made the bulge impossible to ignore.

“She’s here only for you,” Roxanne said, voice low and certain. “I hired her so you can play however you want while I watch. Nothing is off limits as long as everyone stays eager.” Benedict, thirty-five and already hard inside his pants, swallowed. Heather turned slowly, letting the skirt ride higher, then bent at the waist to straighten a cushion that did not need straightening. The motion flashed the full length of her ass and the way the panties disappeared between her cheeks. Roxanne stepped closer and ran a palm down Heather’s spine. “Tell him what you’re wearing underneath, sweetheart.”

Heather glanced back over her shoulder, lips glossy. “Just these little panties and the stockings, sir. They feel tight already.” She straightened, smoothed the tiny apron, and walked past Benedict close enough that her hip brushed his knee. The scent of her perfume mixed with the faint warmth of skin. Roxanne settled into the armchair opposite the couch, legs crossed, one hand resting high on her own thigh. “Start with the shelves,” she told Heather. “Make sure he sees everything.”

Heather moved to the bookcase and rose onto her toes, stretching so the skirt lifted completely. Benedict’s eyes locked on the curve of her ass and the way the bulge shifted when she reached. Roxanne watched his face flush and his hand drift to his lap. “You can touch yourself if you want,” she said. “She’s not going to mind.” Heather dropped back to her heels, turned, and deliberately dragged the feather duster across the front of Benedict’s pants as she passed. The light contact made him groan. She leaned in, breath warm against his ear. “I can dust lower if you open your legs, sir. Or I can stay bent over until you decide where you want me.”

Roxanne’s fingers slipped inside her teddy and began a slow circle. “Answer her, Benedict. Tell her how badly you want that mouth and that ass.” He exhaled hard. “I want both. I want to watch you tease me until I can’t stand it, then I want you on your knees.” Heather smiled, dropped the duster, and sank between his knees without being asked again. She rubbed her cheek along the ridge of his cock through the fabric, then looked up at Roxanne for permission. Roxanne nodded. “Good girl. Keep going. And text your friend. Tell Dante to come over in the red satin. We have room for four.”

Heather pulled her phone from the apron pocket, thumbs moving quickly, then set it aside and unzipped Benedict’s pants. His cock sprang free, thick and already wet at the tip. She licked a slow stripe from base to head while Roxanne moaned softly from the chair. “Dante’s twenty-four and just as pretty,” Heather murmured against the shaft. “He loves being told what to do. He’ll be here in ten minutes wearing the corset and stockings I picked.” Benedict’s hips jerked. “Yes. Bring him. I want all of it.” Roxanne stood, crossed the room, and kissed her husband while Heather continued the lazy tongue work. “Then let’s move to the bedroom so everyone can see. No one gets left out.”

They rose together. Heather kept one hand wrapped around Benedict’s cock as they walked down the hall, stroking just enough to keep him aching. Roxanne opened the bedroom door and turned on the low lamps. The bed was already stripped to the sheets. Heather’s phone buzzed; she checked it and grinned. “He’s downstairs.” Roxanne went to the intercom and buzzed Dante up, then returned to stand beside the bed. When the door opened, Dante stepped in wearing a red satin corset that cinched his waist, matching panties, and sheer black stockings. At twenty-four he was slim, smooth, and already half-hard inside the satin. He looked at the three of them and smiled. “Heather said you wanted company.”

Roxanne beckoned him closer. “We do. Everyone here wants this. Benedict wants both of you on his cock, then he wants to fuck each of you while the other helps. I want to watch and join whenever I feel like it. If anyone needs to stop, say so. Otherwise we keep going until we’re all finished.” Benedict nodded, voice rough. “I want it. All of it.” Heather and Dante answered together, eager and clear. “Yes.” They moved onto the bed without hesitation.

Heather and Dante knelt on either side of Benedict’s hips. Heather still wore the black lace remnants of the maid costume, skirt hiked, panties tugged aside so her own cock rested against her thigh. Dante’s red corset stayed laced, the satin gleaming as he leaned in. Together they lowered their mouths to Benedict’s cock. Heather took the head, swirling her tongue, while Dante licked and sucked along the shaft, their lips meeting in the middle whenever they both rose. Wet sounds filled the room. Roxanne stood at the foot of the bed, one hand inside her teddy, fingers sliding over her own clit as she watched the two mouths work in tandem. “Slower,” she directed. “Make him feel every inch. Heather, take him deeper. Dante, use your hand on what she can’t reach.”

They obeyed. Heather relaxed her throat and sank until her nose brushed Benedict’s stomach; Dante stroked the base and cupped his balls, tongue flicking the sensitive skin just below. Benedict groaned, one hand in each of their hair, not forcing, only holding. Roxanne’s breath quickened. She climbed onto the bed behind them, reached between Heather’s legs, and wrapped her fingers around the ladyboy’s cock, stroking in time with the bob of Heather’s head. “You’re both so pretty like this,” she said. “Keep sucking him while I play with you.”

Heather moaned around the cock in her mouth. The vibration made Benedict’s thighs tense. Dante lifted his head long enough to kiss the side of Heather’s neck, then returned to licking the shaft while Roxanne’s hand moved faster on Heather. Precum slicked Roxanne’s palm. She brought her wet fingers to Dante’s lips; he sucked them clean without pausing his attention on Benedict. “Good,” Roxanne whispered. “Now switch. Dante takes the head. Heather, get underneath and lick his balls.”

They rearranged smoothly. Dante’s red-satin-clad ass rose as he bent to swallow Benedict deep, the corset creaking softly. Heather lay on her back between Benedict’s legs, mouth open, tongue dragging over his sac while her own cock throbbed against her stomach. Roxanne straddled Heather’s chest for a moment, grinding her clit against the smooth skin, then slid off and positioned herself so she could watch every detail. “Benedict, tell them when you’re close, but don’t come yet. I want you inside Heather first.”

He lasted only another minute. “Now,” he gasped. “I need her ass.” Heather pulled off with a wet pop, turned, and dropped to her hands and knees, skirt flipped up, panties yanked to one side. Her hole was already shiny with the lube Roxanne had set on the nightstand earlier. Benedict knelt behind her, rubbed the head of his cock through the slick, and pushed in slowly. Heather’s back arched; she pushed back to meet him until he was buried. “Fuck,” she breathed. “So full.”

Dante moved in front of her without being told. He knelt, fed his cock into her mouth, and held her hair gently while Benedict began to thrust. The motion rocked Heather forward onto Dante’s length and back onto Benedict’s. Roxanne circled the bed, one hand between her own legs, the other trailing over sweat-damp skin. “Harder on the in-stroke,” she told Benedict. “Heather, relax your throat so Dante can fuck your mouth the same way. Dante, don’t hold back—she wants it.”

Benedict gripped Heather’s hips and drove deeper, the sound of skin meeting skin sharp in the quiet room. Heather gagged softly around Dante then swallowed him again, saliva shining on her chin. Roxanne leaned in and kissed Benedict while he fucked, tasting the salt on his lip, then dropped to lick the place where his cock stretched Heather open. Her tongue traced the rim, adding more wetness, and Heather whimpered around the cock in her mouth. “Switch soon,” Roxanne said. “I want to see Dante on his back.”

They changed positions with practiced eagerness. Dante lay down, corset still on, stockings framing his spread thighs. Benedict pushed into him in one smooth stroke, missionary, watching Dante’s face while Heather climbed up and settled her ass over Dante’s mouth. Dante’s tongue went to work immediately, licking Heather’s hole and the underside of her cock while Benedict fucked him in long, deep strokes. Heather rocked, grinding down, one hand braced on Dante’s chest, the other reaching back to stroke Benedict’s thigh. Roxanne knelt beside them, fingers buried in her own pussy, eyes moving from the place Benedict’s cock disappeared into Dante to the way Heather’s cock slapped against Dante’s chin with every roll of her hips.

“Faster,” Roxanne ordered, voice husky. “Benedict, hold his legs wider. Heather, sit heavier—make him taste all of you. Dante, keep that tongue moving even when he pounds you.” They followed every word. Benedict folded Dante’s knees toward his chest and thrust harder, the red satin of the corset bunching. Heather ground down until Dante’s nose pressed into her, his tongue flicking rapidly over her hole and balls. Wet sounds layered: the slap of Benedict’s hips, the slick slide of Heather’s cock against Dante’s lips, Roxanne’s fingers working her own clit. She reached over and wrapped her free hand around Heather’s shaft, jerking it in time with Benedict’s thrusts so Heather had stimulation from every direction.

Heather came first, spilling across Dante’s chest and the red satin while her hole clenched around nothing. The sight pulled a groan from Benedict. He pulled out of Dante, slick and shining, and Roxanne immediately guided him back to Heather, who had dropped to her elbows again, ass up, still trembling. “Fill her,” Roxanne said. “She earned it.” Benedict sank into Heather’s ass in one stroke and fucked her through the aftershocks, hips snapping. Dante, still hard, moved to Roxanne’s side. She opened her mouth without hesitation and took him deep, sucking while she watched her husband pound Heather. Dante’s hands rested lightly on her head; he fucked her mouth in short, eager thrusts that matched the rhythm Benedict set.

Benedict’s rhythm broke. He buried himself to the hilt and came, pulsing thick ropes into Heather’s ass while she pushed back to take every drop. The clench of her body milked him until he shuddered and stilled. At the same moment Dante’s cock swelled on Roxanne’s tongue. She swallowed around him, and he spilled down her throat in hot pulses, hips jerking, a low moan vibrating through his chest. Roxanne drank it all, then pulled off slowly, licking him clean while Benedict eased out of Heather and watched the cum leak from her well-used hole.

They collapsed together onto the sheets, limbs tangled, breathing hard. Heather curled against Benedict’s side, Dante against Roxanne’s, the four of them sticky and warm. Roxanne kissed her husband, tasting Dante on her own lips, and smiled against his mouth. “They’ll be back every weekend,” she murmured. “Same lingerie, same rules. Next time I want you to fuck me while Heather rides Dante’s face and Dante sucks you at the same time. I’ve already picked the white lace set for Heather and the black corset for Dante. We’ll start earlier so we can go twice.” Benedict’s arm tightened around her, already imagining the next Saturday, and Heather’s sleepy laugh against his chest told him both ladyboys were just as ready to return.