Transformed Into a Chastity Sissy Maid by My Bosses, Part 2 (Patreon)

      The first rays of sunlight began to filter through the thin curtains of Harry's bedroom, casting a soft glow across the room. Harry’s thoughts were filled with the days he had spent locked in chastity, a constant reminder of his submission to Isabella and Sarah. The tightness of the chastity device had been a persistent ache, a constant tease that only heightened his anticipation.

      Harry slips out of bed and walks over to his closet. He opens it, and inside, everything is arranged meticulously—soft pinks, delicate lace, and gleaming silks await him. His eyes fall on the sissy maid outfits he would be wearing every day he served Isabella and Sarah.

       He starts with the basics, pulling out a pair of pink lace panties from the drawer. The fabric is delicate, smooth against his soft skin as he steps into them, the sensation causing his cock to squirm within the confines of the chastity cage. The tightness of the device is a constant reminder of his submission, heightening his arousal.

      Next, he reaches for the matching pink garter belt and slides it up his thighs, securing it in place. The suspenders dangle invitingly, waiting to be attached to the sheer, thigh-high stockings he carefully rolls up his legs. Each snap of the suspender clips sends a shiver of pleasure through him, the stockings hugging his legs in a gentle, yet firm, embrace.

       Harry's heart races as he selects a pair of black patent leather heels that force him onto his toes and exaggerate the sway of his hips. He steps into them, feeling the extra height, the way the heels push his posture into something more delicate, more feminine. The click of the heels against the floor is sharp, precise, and unmistakably submissive.

      Next comes the make-up. He sits down at his vanity, the large mirror reflecting his face. He starts with the foundation, creating a flawless base before adding a soft blush to his cheeks, a touch of innocent pink that brings out the femininity in his features. He carefully applies eyeliner, extending it into a subtle wing that gives his eyes a playful, yet seductive, look. The mascara follows, darkening his lashes and making his eyes pop. Finally, he selects a tube of bright pink lipstick, bold and unashamed as he coats his lips, turning them into a perfect pout.

     Harry looks at himself in the mirror, but he's not done yet. His hand hovers over the blonde wig resting on the stand next to him. It's a delicate thing; the curls are soft and bouncy, and the colour is a vivid contrast to his natural hair. He fits it over his head, adjusting it until it sits perfectly, framing his face and adding the final touch to his transformation.

      The last piece of the ensemble waits for him—the sissy maid outfit. He pulls it off the hanger, admiring the way the black and white satin catches the light. The hem is short, just not long enough to cover the chastity belt which is always on display while he is dressed as a maid. He slips into it, the zipper sliding up the back with a satisfying sound, locking him into his new identity. The white apron ties around his waist, a bow sits prettily at the small of his back, and a matching headpiece completes the look.

      Standing in front of the mirror, Harry looks at the transformation. He is no longer the male who woke up just moments ago; he has become something else entirely—delicate, submissive, and eager to serve. The weight of the chastity cage between his legs is a constant reminder of his place, of the role he has to play.

      Harry’s heels click softly on the hardwood floor as he approaches the door to Isabella and Sarah’s bedroom. The silver tray in his hands is perfectly balanced, laden with freshly squeezed orange juice, steaming coffee, and a selection of pastries. His heart pounds in his chest, not just from the effort of carrying the tray but from the anticipation of what lies ahead.

     He takes a deep breath and knocks lightly on the door. A soft giggle filters through the wood, followed by Sarah’s voice, still breathy from their morning activities. “Come in, Sissy.”

     Harry pushes the door open with his hip, carefully stepping inside. The room is warm, the air tinged with the scent of vanilla and Isabella and Sarah’s morning sex, a reminder of what he hadn’t been allowed to participate in. Isabella and Sarah are nestled under the covers, their hair tousled, cheeks flushed. They exchange a knowing look as Harry approaches the bed, head bowed slightly, eyes focused on the tray in his hands.

     “Good morning, Mistress Isabella. Mistress Sarah,” he murmurs, placing the tray gently on the bedside table.

     Isabella stretches languidly, her arm reaching out to run her fingers along Harry’s bare thigh before fondling his swollen balls, just below the hem of his maid outfit. “Good morning, Sissy. Did you sleep well?” Her voice is sweet, but there’s a teasing lilt to it that makes Harry’s heart race.

      “As well as I could, Mistress,” he replies, his voice tight with the effort of keeping his composure as she plays with his sensitive balls. The chastity cage feels, even more, constricting now, a constant reminder of the desires he isn’t allowed to fulfil.

       Sarah sits up, the sheet falling away to reveal her bare shoulders. She takes a sip of her juice, her eyes dancing with amusement as they roam over Harry’s figure. “You look so precious in your little outfit, Sissy,” she coos. “It’s almost a shame you weren’t here to help us earlier. We could’ve used a hand.”

     Harry swallows hard, the double meaning in her words clear. “I’m here to serve in any way you need, Mistress,” he says, his voice barely above a whisper.

      Isabella chuckles softly, her fingers trailing up to the hem of Harry’s skirt, lifting it just enough to reveal the pink lace panties underneath. “And you’re such a good little sissy maid, aren’t you? All dressed up for us, knowing exactly where you belong.”

       Harry’s cheeks flush, both from the words and the way her touch makes his cock strain helplessly against the chastity cage. “Yes, Mistress,” he replies, his voice trembling slightly.

       Sarah leans over, placing a kiss on Isabella’s shoulder before turning her attention back to Harry. “Such a shame you’re locked up, though. All that pretty lace and nowhere for you to go.”

       They both laugh softly, the sound of it sending a fresh wave of humiliation through Harry. He feels the weight of his submission more keenly than ever, knowing that his pleasure is entirely in their hands.

       Isabella finally lets go of his balls. “Well, Sissy, we wouldn’t want to keep you from your chores before the party tonight. There’s so much to be done—ironing, cleaning, making sure everything is perfect for us. We’ll be expecting you to do a thorough job, won’t we, Sarah?”

      “Oh, definitely,” Sarah agrees, her smile mischievous. “And who knows? Maybe if you’re well-behaved at the party, we will reward you. But only if you’re very, very good.”

Harry nods, his breath quickening at the thought. “Yes, Mistress. I’ll be the best I can be.”

      With a final curtsy, he retreats from the room, the sound of their laughter following him out. Once in the hallway, he takes a moment to steady himself, the teasing words still ringing in his ears. The tightness of the chastity cage is almost unbearable now as he leaks profusely into his panties, his body throbbing with unfulfilled need.

      But there’s no time to dwell on it. He has work to do—shirts to iron, floors to scrub, and countless other tasks to complete. As he sets to work, his mind remains focused on the image of Isabella and Sarah in bed, their teasing smiles etched into his memory.

      His chores take on a new sense of purpose as he imagines their approval, every task bringing him closer to the possibility of another moment in their presence. The anticipation, the desire, and the constant pressure of the chastity cage keep him on edge, a mixture of frustration and excitement that spurs him on through each task.

     Harry's heart raced uncontrollably, each beat echoing his deepening humiliation. Dressed in a pink sissy maid outfit—complete with a frilly apron, delicate white stockings, and four-inch black heels—he felt a profound sense of vulnerability. The outfit, though designed for the evening’s theme, left him feeling exposed and mortified.

     The doorbell rang, and Harry's breath caught in his throat. With trembling hands, he gripped the doorknob and slowly opened the door, revealing a group of women clad in shiny latex. His face flushed even deeper as he forced a curtsy, the movement making the hem of his short skirt swish awkwardly. Their initial surprise quickly turned to raucous laughter.

     “Oh my goodness!” one woman exclaimed, her voice laced with derision. “This must be Isabella and Sarah’s new maid. Look at the chastity belt around its cock and balls. It’s a sissy maid!!”

     Harry’s face burned with a deep crimson as he fumbled for words. “H-Hello, everyone. Can I take your coats and bags?”

     As he awkwardly reached out to take their coats, their laughter grew even louder. “Oh, you’re such a little bitch! I didn’t expect such a… pathetic coward to be opening the door.”

      The group’s laughter grew louder as they moved past him, their comments continuing to sting. Harry struggled to maintain his composure, his humiliation mounting with every playful jab and insult.

      As the door closed behind the last guest, Harry stood alone, his cheeks still burning with shame. He took a deep breath, trying to calm himself as he prepared to rejoin the party. Despite the biting comments and the overwhelming embarrassment, he reminded himself that he would get rewarded if he was a good maid.

      Despite the intense embarrassment, he knew he had to endure the rest of the evening with as much grace as he could muster. As he turned to head back inside, he hoped the rest of the night would bring a respite from the relentless teasing.

     The room was filled with the soft glow of ambient lighting and the gentle hum of conversation. Harry moved carefully among the guests, balancing a tray of drinks with a mixture of nervousness.

     His cock strained within the steel belt and his balls ached. Here he was dressed as a sissy maid serving drinks to twenty latex-clad lesbians in Isabella's and Sarah’s house.

As he approached a group of women gathered around a low table, he tried to maintain his composure. “Good evening, Mistresses. May I offer you a drink?” he asked, his voice barely steady.

     The room was filled with the sounds of laughter as the women took their drinks from Harry, their playful taunts ringing out. “Look at you, sissy,” one of them said, her voice dripping with mockery. “You’re such a good little maid.”

     Harry's cheeks flushed a deep red as he stood there, the centre of their attention. One of the women, with a mischievous glint in her eye, pulled out her phone and snapped a picture. “I have to share this with my friends,” she said with a grin. “I might just have to get myself a sissy maid like you.”

     His embarrassment intensified as they continued to tease him. Another woman stepped forward, her fingers boldly exploring the chastity cage and gently fondling him. “Aww, does the little cock want to cum?” she purred, her words laced with playful cruelty. Harry’s discomfort was palpable, and he could feel the heat rising as he leaked from the cage in front of them.

      The laughter grew louder as the women enjoyed the spectacle. They made Harry strike various awkward and humiliating poses, their phones flashing as they captured each moment. Harry’s sense of shame mingled with a heightened sense of arousal, and he struggled to maintain his composure under their relentless teasing.

     As he tried to regain his composure, he noticed Sarah and Isabella watching from a nearby table. Their smirks were both knowing and commanding. They had promised rewards for a job well done, but their threat of punishment for any failure loomed large in his mind.

     “Would the mistresses like a drink?” Harry asked, his voice polite but tinged with a hint of nervous anticipation.

     Sarah and Isabella exchanged knowing smirks before nodding in agreement. Harry served each of them with a careful touch, placing their drinks on the table.

      Sarah’s hand rested lightly on Isabella’s arm, their conversation taking on a flirtatious undertone. He saw the key to the chastity belt resting between Sarah’s breasts. His cock strained in the chastity belt.

      Sarah’s fingers traced a teasing path along Isabella’s skin, making her shiver with pleasure. Isabella responded with a soft, lingering kiss on Sarah’s lips, their passion evident even in the subtlety of their touch.

      Harry’s breath caught in his throat, his gaze locked on their affectionate display. The sight stirred something deep within him, and he felt a flush of arousal as he shifted uncomfortably, the sensation of his chastity device intensifying his growing need.

     Sarah’s eyes flicked toward him, a playful glint in her gaze. She smiled, her lips curling in a teasing manner. “Harry, are you enjoying the show?” Her tone was both teasing and provocative.

     Isabella giggled softly, her fingers continuing to caress Sarah’s cheek. “It seems our little sissy is quite captivated by us.”

     Harry’s face flushed a deep red as he swallowed hard, trying to steady his voice. “I—I’m just here to make sure you have everything you need, Mistresses,” he stammered.

     Harry proceeded to serve the other guests as they rang the bells on their tables to summon him.

     “Oh, he’s adorable,” one of the guests, a statuesque woman with raven hair, cooed as she accepted her champagne. She reached out to touch the frills of his apron, her fingers brushing against his chastity. “I didn’t realize the girls had such a…dedicated little servant.”

     Harry moved to the next guest, trying to keep his hands steady as he offered another glass. But the teasing only intensified. A woman in a sleek black latex took the glass and leaned in close, her lips brushing his ear as she whispered, “Do you enjoy this, being dressed up like a little sissy? You look so pathetic. You could never pleasure a real woman.”

     Another woman, with a short bob and a mischievous glint in her eye, pulled out her phone and snapped a picture as Harry placed her drink in front of her. “This is too good to miss,” she said, showing the screen to the others. “He looks like he was born for this.”

     Harry’s stomach twisted with a mix of humiliation and arousal, the chastity cage pressing uncomfortably against his body as the evening wore on. He continued to serve the women, refilling glasses and bringing out plates of food, each task accompanied by more teasing, more whispered remarks and more stolen photographs.

      Another ring of the doorbell echoed through the house, and Harry’s heart raced as he walked toward the front door, his heels clicking sharply on the polished wooden floor. His sissy maid outfit—complete with a frilly pink apron, short skirt, and delicate white stockings—felt more out of place than ever.

      When he opened the door, he was met with a sight that made him freeze in shock. There stood Holly, his ex-girlfriend, with another woman and a massive, knowing smirk on her face.

     Harry’s face flushed a deep red as he took in the sight of Holly, her eyes gleaming with a mix of surprise and amusement. He had known she was bisexual, but he had never expected to see her at this party, let alone find her here at this moment.

     Holly’s laughter burst forth, a loud and clear expression of her delight. “Well, well, Harry! What a surprise! I never imagined I'd see you like this.” Her eyes roamed over his outfit, lingering on every detail with open amusement.

     Harry’s heart pounded with a mix of embarrassment and dread as he tried to maintain his composure. “H-Holly,” he stammered, “I didn’t know you’d be here.”

     “Oh, I couldn’t resist coming,” Holly said with a playful tone. She stepped closer, her gaze taking in every aspect of his attire. “And I must say, you’re certainly making an impression.”

     Without missing a beat, Holly pulled out her phone and snapped a picture of him standing there, his cheeks flushed with humiliation. “I’m sharing this one,” she said with a teasing grin. “I have some friends who just have to see this.”

     Harry’s discomfort deepened as Holly continued to tease him. “You really went all out, didn’t you? I never thought I’d see you in something so... revealing. It’s almost adorable how you’re trying to pull this off.”

     Her words stung, and he could feel his face grow even hotter as she revelled in his discomfort. She took another picture, her smirk widening. “I always knew you were a pushover, but I never expected to see you converted into a cock sucking sissy bitch. I’m tempted to get a few more shots from different angles for all our old friends...”

     As she continued to snap pictures, Holly’s teasing tone remained playful but unrelenting. “Oh, don’t look so embarrassed, Harry. You obviously were born to be a sissy maid. Your little shrimp cock could never pleasure me anyway.”

      Harry could hardly focus on anything other than the acute embarrassment of the situation. Holly’s laughter and teasing felt like a relentless spotlight on his vulnerability. Each comment and photo seemed to deepen his humiliation, leaving him feeling exposed and uncomfortable.

     When Holly finally stepped back, her laughter still echoing, Harry was left standing at the door, feeling a mix of relief and lingering embarrassment. The encounter had been both intensely humiliating and unexpectedly intimate, and he couldn’t shake the feeling that Holly had made the evening unforgettable for all the wrong reasons.

     Once the meal and drinks were finished, the tables and chairs were cleared from the banquet hall. Several large items, such as St. Andrew's crosses, benches, and various pieces of furniture, were brought into the room.

     Harry was tightly secured to the St. Andrew's cross in the middle of the room. Isabella and Sarah then began whipping his ass and back with leather whips and floggers, much to the delight of the spectators.

"Who is our little sissy bitch?" they taunted.

"I am!" Harry cried out in response to the harsh whippings.

"And who owns this ass and balls?" they demanded.

"Mistresses!" he pleaded as they left long red marks and welts across his ass.

     Through his tears, Harry could see Holly holding her phone, recording the scene of him being whipped by Isabella and Sarah while he begged them to stop.

     Once they finished, the other women clapped and cheered. Soon, they began taking turns whipping and punishing Harry. Those who weren’t participating began playing together, kissing, engaging in oral sex, and using strapons on each other, all while continuing to punish Harry.

     Harry couldn’t believe what was happening. Here he was, dressed as a sissy maid, locked in chastity, and being whipped and punished by a group of latex-clad dominatrixes, all while they had sex around him.

     His balls were bruised and purple from the punishment, yet he was still leaking on the floor. Holly started whipping him again, teasing him about having a small cock and never being able to please her.

       As the room's energy shifted, Holly stepped forward, her gaze fixed on Harry with a mix of disdain and amusement. She held the whip with a practised hand, her eyes glinting with a provocative spark.

     "Look at you, Sissy," Holly said, her voice dripping with scorn as she drew closer. "Still the same pathetic lover you always were. You could never make me cum, and you were always a loser"

      With a swift motion, she cracked the whip against his exposed ass, the sting of the leather causing him to flinch and yelp in pain. The sharp sensation was followed by a lingering burn that made him squirm.

     "You were never good enough, and now look at you," Holly taunted, her voice cold and mocking. "Dressed up like a sissy maid, locked in chastity, and begging for release. How utterly pathetic."

      Each lash of the whip was deliberate, designed to leave its mark and intensify his feelings of humiliation. Holly's words cut deeper than the whip itself, her disdain evident in every syllable.

     Harry’s breath came in ragged gasps, his body trembling under the relentless impact of the whip. The combination of physical pain and emotional humiliation was overwhelming, making it hard for him to process anything beyond the immediate sting and Holly's cruel taunts.

     Holly circled him, her eyes never leaving his as she laid down another lash. "You always thought you were something special," she said, her tone dripping with contempt. "But look at you now—just a sissy, struggling to keep up with the real women around you. How does it feel to be so utterly useless?"

     Harry was unable to respond due to the intense pain he was enduring. Isabella, Sarah, Holly, and the other dominatrixes had thoroughly broken him down, leaving him feeling like nothing more than a sissy maid.

     Harry was finally uncuffed from the cross and led up to Sarah and Isabella’s study. He knelt in front of Isabella who was holding a stack of papers.

     "You've been such a good sissy tonight," Isabella said with a commanding tone, her voice firm as the whip dangled in her hand. "We’ve decided to reward you with a conservatorship. Sign here."

     Harry, utterly broken and eager to please, signed the papers without hesitation, his submission complete.

     Once the documents were signed, Isabella turned and walked away, a satisfied smirk playing on her lips.

     Sarah stepped closer, her eyes gleaming with a mix of dominance and pleasure. She grasped Harry's swollen, bruised balls in her hand, squeezing firmly.

“We now have full control over your body and life, sissy,” she purred. “It’s time to ramp up your training.”

     Harry knelt there, feeling the weight of his submission. He had just signed away his freedom to Isabella and Sarah, and he was left anxiously wondering what new experiences awaited him as their sissy maid.