Amanda’s heart raced as she handed John the birthday card, her lips curling into a sly smile. “Happy birthday, sweetie,” she purred, leaning in to plant a sultry kiss on his lips. The taste of her lipstick lingered as she pulled away, her eyes locking onto his with a mix of mischief and command. John hesitated, his hands trembling as he took the card. He could feel the weight of her expectations pressing down on him, even before he opened it.
The envelope was sealed with a delicate pink wax stamp, something Amanda had clearly gone out of her way to make special. He slid his finger under the flap, breaking the seal with shaky hands. Inside, the card was adorned with glittery cursive letters that read, “Your Fantasy Awaits.” His breath hitched as he unfolded the note tucked inside. Amanda’s handwriting sprawled across the page, each word dripping with anticipation.
“John,” it began, “this weekend is all about you—or rather, all about her. From the moment you finish reading this, you are no longer my husband. You are my sissy maid, and you will remain so until Monday morning. You are to wear nothing but women’s clothing for the entire weekend. No exceptions. Heels during waking hours, makeup flawless at all times. And yes, you will be wearing lingerie beneath your outfits. I expect the house to be spotless by the time I return from getting my nails done. Oh, and pack your bags—we have a little getaway planned tomorrow.”
John’s face flushed as he read the instructions, his stomach twisting with a mix of excitement and dread. Amanda watched him intently, her arms crossed over her chest, her expression unreadable. She leaned closer, her voice dropping to a husky whisper. “Don’t look so scared, darling. This is what you’ve always wanted, isn’t it? To be stripped of your masculinity, forced to embrace your feminine side completely?”
He nodded weakly, unable to meet her gaze. Amanda smirked, running a perfectly manicured fingernail along his jawline. “Good girl. Now go get dressed. I want to see you in your maid uniform when I leave.”
As Amanda headed out the door, her heels clicking against the hardwood floor, John stood frozen in the living room. The reality of the weekend ahead sunk in. He glanced at the clock—it was only 9:00 AM, and already his world felt like it was spinning out of control. He made his way to the closet where Amanda kept his “special” clothes, a collection she had curated meticulously over the years. The black-and-white French maid uniform hung neatly, complete with ruffled lace trim and a matching headband. Beneath it, folded delicately, was a set of satin lingerie—a matching bra, panties, and garter belt.
His hands trembled as he unbuttoned his shirt, sliding it off his shoulders and letting it fall to the floor. The cool air kissed his skin as he stepped out of his boxers and reached for the lingerie. The fabric was soft against his skin, but the sensation of being encased in something so inherently feminine sent a shiver down his spine. He fastened the bra around his chest, adjusting the padding to give the illusion of breasts. The panties hugged his hips snugly, the delicate lace scraping against his most sensitive areas.
Next came the stockings, their silky texture gliding over his legs as he rolled them up and attached them to the garter belt. The final touch was the maid uniform itself. He slipped it on, the skirt swishing around his thighs as he adjusted the ruffles. The heels clicked loudly as he walked to the bathroom to apply his makeup. Amanda had left him specific instructions: foundation, blush, eyeliner, mascara, and lipstick—all in shades that complemented his new persona.
By the time he was finished, the reflection staring back at him was almost unrecognizable. His cheeks were rosy, his lips painted a deep crimson, his eyes framed by thick lashes. He looked… beautiful. The thought both thrilled and terrified him.
The housework passed in a blur. Vacuuming, dusting, mopping—he moved through the tasks mechanically, his mind racing with thoughts of what was to come. Amanda returned home late in the afternoon, her arms laden with shopping bags. She appraised him with a critical eye, circling him slowly as if inspecting a piece of art.
“Not bad,” she said finally, her tone tinged with approval. “You clean up nicely, darling. But don’t get too comfortable—tomorrow is going to be much more intense.”
John swallowed hard, his pulse quickening at the implication. Amanda gestured toward the kitchen. “Dinner won’t cook itself. Chop-chop, my little maid.”
That night, Amanda spent time on the couch watching a Netflix series while John, looking ridiculous, massaged her feet for a few hours. Amanda then casually dropped a bombshell. “Oh, by the way, James is joining us tomorrow.”
John nearly choked on his drink. “James?! As in… your…?”
Amanda smirked, her eyes gleaming with mischief. “Yes, that James. Don’t act so surprised. You knew this was part of the fantasy.”
He did know, of course. They had discussed it countless times, but now that it was actually happening, the reality felt overwhelming. Amanda leaned closer, her hand resting on his thigh. Her touch sent a jolt through him, her nails digging ever so slightly into his skin.
“You’re going to love it,” she whispered, her breath hot against his ear. “Imagine it—me, writhing beneath him, moaning his name while you kneel beside us, ready to serve. It’s going to be perfect.”
The next morning, John woke early, his nerves buzzing with anticipation. He showered quickly, and as requested, shaved his entire body. Getting out of the shower he noticed Amanda had laid out three dresses for him to choose from for the trip—one for the drive to the hotel, one for the drive back, and one for the evening with James. He opted for a simple daytime dress for the car ride, it was white, fitting for daytime but very short, likely to make him feel very self-conscious.
The drive was excruciating. Every passing car seemed to stare at him, their drivers peering through the windows with curiosity or disdain. Amanda drove calmly, humming along to the radio as if nothing were amiss. John fidgeted in his seat, tugging at the hem of his dress every few minutes in a futile attempt to cover more of his thighs.
When they arrived at the resort, Amanda parked the car and turned to him with a wicked grin. “Wait here,” she instructed. “I’ll check us in. Be a good girl and try not to draw too much attention to yourself.”
She disappeared into the lobby, leaving John alone with his thoughts. His stomach churned as he imagined what lay ahead. Amanda returned a short while later, handing him a keycard with a playful wink.
“Room 312. Bring your bag up and meet me there. Remember—you’re just the help. Act accordingly.” Amanda quickly walked away to their room leaving John to make the embarrassing walk on his own either through the main lobby or with any luck through a side door to draw less attention.
The walk through the hotel felt like an eternity. John clutched his overnight bag tightly, his heels clicking loudly against the polished floors. He kept his head down, avoiding eye contact with other guests, though he could feel their stares burning into him. By the time he reached the room, his hands were shaking so badly he could barely open the door.
Inside, Amanda and James were already waiting. James sat on the edge of the bed, his muscular frame towering over John’s petite form. Amanda lounged beside him, her body draped in sheer lingerie that left little to the imagination. She beckoned John closer while pointing at James’ cock, her voice dripping with authority.
“You know what to do, darling. Make yourself useful.”
John dropped to his knees, his heart pounding as he began to unzip James’ pants. The air was thick with tension, Amanda’s laughter ringing in his ears as she settled back to watch the show.
“Happy birthday, sweetheart,” she purred. “This is just the beginning.”
James’ cock sprang free from his pants, thick and already half-hard. John hesitated for a moment, his breath hitching as he stared at it, the reality of what he was about to do crashing down on him. Amanda’s voice cut through the silence like a whip.
“Don’t stop now, sweetie. You know this is what you’ve been begging for.”
Her tone was teasing, but there was no mistaking the command in her words. John swallowed hard, his throat tightening as he leaned forward, his lips trembling as they brushed against the tip of James’ cock. It felt warm, almost scorching against his skin, and the faint taste of salt hit his tongue as he cautiously licked the underside.
“That’s it,” Amanda cooed, shifting closer to the edge of the bed. Her fingers trailed lazily over James’ chest, her nails lightly scratching his skin as she watched John with predatory interest. “Take more of him, darling. Don’t be shy—he doesn’t bite.”
John’s cheeks burned, but he obeyed, opening his mouth wider and sinking down onto James’ length. The sensation was overwhelming, the weight of it pressing against his tongue, the heat filling his mouth. His hands trembled as they rested on James’ thighs, gripping tightly for support as he bobbed his head tentatively.
Amanda leaned forward, her hand slipping into John’s hair, her fingers tangling in the strands. “You can do better than that,” she murmured, her voice low and insistent. “Use your tongue. Show him how much you want this.”
John tried to comply, swirling his tongue around the shaft as best he could, but it wasn’t enough. Amanda’s grip tightened, her nails digging into his scalp as she pushed his head down further. His gag reflex kicked in immediately, his throat convulsing as James’ cock pressed deeper, the tip nudging the back of his mouth. Tears sprung to his eyes, but Amanda didn’t let up.
“Relax, baby,” she purred, her voice dripping with false sweetness. “You look so pretty like this, taking him so well. Doesn’t she, James?”
James chuckled darkly, his hand coming to rest on the back of John’s head, adding to the pressure. “Yeah, she does. Keep going, sweetheart. Let’s see if you can make me cum once before I take your wife for round two.”
The humiliation burned hotter than the stretch of his throat, but John couldn’t deny the thrill that shot through him at their words. He let out a muffled whimper, saliva pooling in his mouth as Amanda guided him faster, her grip unrelenting. His jaw ached, his breath coming in shallow gasps whenever she allowed him to surface for air, but he didn’t dare pull away.
Finally, James groaned, his hips jerking slightly as he reached his peak. “Fuck, that’s it—”
“Swallow it all, Sissy” Amanda demanded. Warmth flooded John’s mouth, bitter and thick, and he swallowed instinctively, his throat working to take every drop. Amanda laughed softly above him, her fingers loosening their grip as she released him.
“Good girl,” she whispered, patting his cheek as he pulled back, his lips swollen and glistening. “Now clean him up. You wouldn’t want to leave a mess, would you?”
John nodded weakly, his body still trembling as he leaned forward again, his tongue flicking out to lap at James’ softening cock. The taste was overwhelming, but he forced himself to continue, his movements slow and deliberate as he cleaned every inch.
Amanda shifted behind him, her hands sliding down her own body as she admired the scene before her. “God, you’re so good at that,” she moaned, her fingers dipping beneath the lace of her panties. “I think James deserves another round, don’t you?” “This time get him ready to fuck your wife.”
John froze, his heart pounding as he glanced up at her, his eyes wide with disbelief. But Amanda only smiled, her expression full of wicked intent.
“Go on,” she urged, her voice light but firm. “Get him hard again. I want to show you how much fun I can have fucking a real man.”
John’s stomach twisted, but he couldn’t resist the pull of her command. He lowered his head once more, his tongue tracing slow circles around James’ shaft, coaxing him back to attention. It didn’t take long; within minutes, James was fully erect again, his breathing heavy as he watched John work.
Amanda climbed onto the bed, straddling James’ lap as she kissed him deeply, her hands tangled in his hair. She broke away with a smirk, glancing down at John. “Keep going, baby. Don’t stop until I say so.”
John obeyed, his movements growing more frantic as Amanda began to ride James, her moans filling the room. The sounds were torturous, each one sending a jolt of shame and arousal through him as he knelt on the floor, his face buried between James’ thighs.
Hours later, Amanda demanded John leave the room, Amanda turned to John with a satisfied smile. “It’s time for James and I to be alone.” “Time for bed, sweetheart. Big day tomorrow.”
She led him to the adjoining room, shedding her lingerie as she went. John followed meekly, his legs weak and his mind foggy with exhaustion. Amanda handed him a silky nightgown, watching as he slipped it on, the fabric clinging to his slender frame.
“Sleep tight, love,” she said, brushing a kiss against his forehead before closing the door behind her, leaving him alone in the dark feeling degraded, embarrassed, and wondering why he ever fantasized about something like this.
The next morning, sunlight streamed through the curtains, rousing John from a restless sleep. He blinked groggily, the events of the previous night rushing back to him in vivid detail. Before he could fully process them, the door swung open, revealing Amanda and James, both dressed and ready for breakfast.
“Shower quickly,” Amanda instructed, her tone brisk as she tossed a bag of makeup onto the bed. “Shower and be dressed in something pretty. I expect you to look flawless by the time we get back. Oh, and don’t forget—James deserves a proper goodbye before he leaves.”
John’s stomach dropped, but he nodded silently, his hands shaking as he reached for the makeup bag.
As Amanda and James disappeared down the hallway, John stood in front of the mirror, certainly not as a man but as a true submissive sissy to his wife with no dignity left. The reflection staring back at him was unrecognizable—painted lips, smudged eyeliner, and a nightgown that clung to his curves.
He took a deep breath, made his way to the shower, steeling himself for what was to come. This was his fantasy, after all. And Amanda wasn’t done yet.
John stood under the steaming spray of the shower, the water cascading over his body as he tried to wash away the lingering taste of James from his mouth from the previous night. His mind raced, torn between humiliation and the strange arousal that still hummed low in his belly. He scrubbed at his skin with trembling hands using the loofah Amanda left for him. The scent of lavender body wash filled the air, but it did little to calm his nerves. He thought about calling an end to the weekend but remembered having nothing but delicate feminine things to wear. He realized his fantasy was seriously too much and wanted it to stop. But because of Amanda’s careful planning he had no choice but to do as he was told.
When he stepped out of the shower, John reached for a towel, only to find a silky pink robe waiting for him instead. He sighed, slipping into the garment before sitting down at the vanity to apply his makeup. This is what she wants, he reminded himself, his reflection staring back at him with hollow eyes. And deep down… it’s what you want too.
The thought sent a shiver down his spine as he carefully lined his lips with a cherry-red pencil, following up with a matching gloss that made them look plump and shining. Next came the blush, brushed lightly across his cheeks, and a sweep of mascara to accentuate his lashes. By the time he was done, the girl in the mirror looked back at him with wide, expectant eyes. She was ready—even if John wasn’t.
He rummaged through the suitcase Amanda had packed for him, pulling out a short, daytime dress in pastel pink. It clung to his hips and thighs, the hem barely grazing mid-thigh. Paired with sheer stockings and white heels, the outfit was both humiliating and submissive. The sound of his heels clicking against the tile floor echoed in the quiet room as he paced nervously, waiting for Amanda and James to return.
When the door finally clicked open, John froze like a deer caught in headlights. Amanda strode in first, her hair tousled and her face flushed from whatever fun they’d been having. James followed close behind, his smug grin making John’s stomach churn.
“Oh, don’t you look pretty,” Amanda cooed, circling him like a predator inspecting its prey. “You’ve outdone yourself, darling.”
John forced a weak smile, his hands fidgeting with the hem of his dress. “Thank you…”
Amanda turned to James, her voice dripping with sweetness. “Wouldn’t you agree, James? Doesn’t my husband make the most adorable sissy slut?”
James’s eyes raked over John, lingering on the exposed curve of his thigh. “Absolutely. I can see why you’re so proud of him.”
Heat flooded John’s cheeks, but he didn’t dare protest. Instead, he kept his gaze fixed on the floor, his heart pounding in his chest.
“Now, now, don’t be shy,” Amanda teased, cupping John’s chin and tilting his face up. “James deserves a proper goodbye, don’t you think?”
John’s breath hitched, his pulse quickening as he glanced nervously at James. “Y-yes, ma’am…”
Amanda stepped aside, gesturing for John to approach James. He hesitated for a moment, his heels wobbling slightly as he took a few tentative steps forward. When he dropped to his knees, the cool hardwood pressed against his stockinged legs, sending another wave of shame coursing through him.
James smirked down at him, clearly enjoying the display. “Good girl,” he murmured, reaching out to gently stroke John’s cheek.
The touch sent a jolt through John, his body betraying him as a flush of warmth spread through his core. He swallowed hard, his hands trembling as he reached for the zipper on James’s pants. The sound of the fabric sliding down seemed impossibly loud in the otherwise silent room.
As John leaned in, Amanda’s voice cut through the tension like a whip. “Don’t forget to take your time, sweetheart. Make it memorable.”
His stomach twisted, but he obeyed, his lips brushing against James’s length before taking him fully into his mouth. The salty-sweet taste flooded his senses, and he fought back the urge to gag as he worked to please James. Above him, James let out a low groan, his fingers tangling in John’s hair as he guided him deeper.
Amanda watched with a satisfied smile; her arms crossed as she leaned against the wall. “Such a good little obedient cock sucking sissy girl of a husband,” she purred, her tone dripping with approval. “You’re doing so well, darling.”
John’s cheeks burned, but he focused on the task at hand, his tongue swirling and his lips moving in rhythm with James’s thrusts. The minutes stretched on, each one feeling like an eternity, until James finally tensed, his release spilling into John’s mouth. John swallowed reflexively, the bitter taste lingering on his tongue as he pulled away.
“Good girl,” James said again, his voice husky as he tucked himself back into his pants. “I’ll miss our little playdates.”
John flushed, wiping his mouth with the back of his hand as Amanda stepped forward to kiss James goodbye. When the door finally closed behind him, the room felt strangely empty—though not for long.
“Grab your bag,” Amanda instructed, already heading toward the door. “I’ll meet you downstairs. And don’t dawdle—you wouldn’t want anyone to see you looking like that, would you?”
John’s stomach sank as he hurried to gather his things, the weight of Amanda’s words pressing down on him. He slung the bag over his shoulder, his heels clacking loudly against the floor as he made his way to the elevator. Every step felt like a struggle, his heartbeat racing as he imagined the judgmental stares of strangers.
The ride down was agonizing, the mirrored walls reflecting his painted face and short dress back at him in vivid detail. When the doors slid open, John hesitated for a moment before stepping out into the lobby, his head held high despite the knot of anxiety in his chest. He could feel their eyes on him, hear the whispers and muffled laughter, but he didn’t dare look up.
By the time he reached the car, his palms were slick with sweat, his breath coming in shallow gasps. Amanda was waiting for him, her expression unreadable as she watched him climb into the passenger seat.
“So?” she asked, her tone light and teasing. “How does it feel to be seen as a pretty little sissy by the whole world?”
John’s throat tightened, but he managed to force out a response. “Embarrassing…”
“Good,” Amanda said, patting his knee affectionately. “That’s exactly how it should feel.”
The drive home passed in relative silence, the tension in the car thick enough to cut with a knife. It wasn’t until they stopped at a gas station that Amanda spoke again.
“Go pump the gas,” she ordered, handing him a credit card. “And don’t dilly-dally.”
John balked, his eyes widening in horror. “But—but everyone will see me!”
Amanda arched a brow, her lips curving into a sly smile. “Exactly. Maybe next time you’ll think twice before asking for a fantasy weekend.”
With a sigh of resignation, John climbed out of the car, his heels clicking against the pavement as he approached the pump. He could feel the eyes of other motorists on him, their stares burning into his skin as he fumbled with the nozzle. Each second felt like an eternity, the heat of embarrassment flooding his cheeks as he finished filling the tank and hurried back to the car.
Back at home, Amanda wasted no time in putting him to work. “Change into your maid uniform,” she said, tossing him the frilly black-and-white dress. “You’ve got laundry to do, don’t forget to unpack our bags, and hand wash our lingerie from the trip. I’ll be in the living room if you need me.”
John nodded silently, slipping into the uniform with practiced ease. As he began sorting through the clothes, his mind drifted back to the events of the weekend—the humiliation, the degradation, the strange thrill that still lingered beneath it all. He knew he should feel angry or resentful, but instead, there was only… acceptance.
In the living room, Amanda lounged on the couch, her feet propped up on the coffee table as she scrolled through Netflix. “Don’t forget my foot rub, darling,” she called out, her voice dripping with amusement. “You’ve earned it after such a busy weekend.”
John sighed, setting aside the last of the laundry before kneeling at her feet. The soft glow of the TV illuminated the room, casting shadows across Amanda’s face as she smiled down at him.
“Happy birthday, sweetheart,” she whispered, leaning down to press a gentle kiss to his forehead. “I hope it was everything you dreamed of…”