My Sister, My Mistress

An 18-year-old sissy-boy, Ryan, with his wrists bound above his head to the bedpost with velvet restraints, his cheeks flushed a deep shade of crimson that matches the ruffles on his Sissy Princess Damsel outfit. The skimpy pink dress clings to his body, revealing the lacy panties he's been forced into as part of his feminization. His legs are spread wide, the hem of the dress hiked up to expose his smooth, shaven thighs and the sheer panties that leave little to the imagination. His older sister, Chloe, stands over him, a wicked smirk playing on her lips as she tightens the corset around his waist, emphasizing his newfound curves. In her dominant hand, she wields a riding crop, which she uses to tease and punish his sensitive skin with a series of sharp, precise slaps that leave red welts in their wake. Despite his pleas for mercy, the sparkle in her eyes reveals she's enjoying every moment of his discomfort. Chloe's own attire is a stark contrast to her brother's – a black leather dominatrix outfit that accentuates her authoritative figure, complete with thigh-high boots and a studded choker. She wears a pair of gloves that match her outfit, ensuring Ryan feels her every touch with a mix of pain and pleasure. The room is dimly lit, casting shadows that dance across the walls, which are adorned with various BDSM toys and accessories. The bed is a plush, royal blue, with gold-trimmed sheets that seem to amplify the power dynamics at play. The atmosphere is thick with the scent of lust and submission as the scene unfolds, capturing the essence of forced feminization and the thrill of sibling domination.

Ryan's breath hitched as Kendra yanked the corset tight, forcing him to gasp. His newly enhanced curves — soft, round, and utterly intoxicating — pushed against the lace and satin of his bodice. The silicone implants felt heavy, obscenely erotic, beneath the thin fabric. His mind raced, a mix of humiliation and dark arousal coursing through him. Kendra ran her fingers across his chest and down, dragging them lightly across the hard nubs of his nipples, making him gasp again. Her eyes stayed on his, watching his reactions as her fingers roved lower. She reached his thighs, then finally cupped his bulge, massaging it through the fabric of his panties. She loved the feel of his growing erection. Her mouth watered as she remembered the taste of it. Ryan's face flushed, his breath coming in quick gasps. She loved how he betrayed his lust for her. She leaned in, her breath hot on his ear. “Look at you, Ryan. All dressed up like my little princess. You know how much I love having you like this. Doesn’t it turn you on, knowing I want your cock? Knowing I want it in every hole I have.” His mind was a whirlwind of shame, anger, and twisted desire. Kendra dragged the riding crop down his body, tracing his shape, his nipples, his hips, and finally pressing the tip against his cock through the silk. “You love this,” she growled. “You love being my little sissy slut. You love it when I make you take it. You love it when I make you beg for it. You love it when I suck your cock. You love it when I ride it. You love it when I take it in my ass.” She pressed the riding crop harder against his cock. She held it there, watching his reactions, building the tension and his arousal. Ryan let out a groan. Kendra liked it — she loved controlling him, pushing him, making him crazy with need. She knew how much he wanted her, and she wanted him too. “You have so much to learn, little sissy. You have so much to learn about how much I love fucking you. About how much I want your cock. About how much I want to ride it and have it deep in my ass.” Her lips brushed against his ear. “And when I'm done with you, you’ll be begging for more. If you're lucky, maybe I'll let you cum. Maybe I will let you fill me up and watch as my juices drip out of my pussy and my ass. But only if you're good. Only if you're my good little sissy slut.”

Kendra grinned, her teeth grazing Ryan's earlobe as she pulled back slightly. She dragged the riding crop up and down his bound length, the stiff leather teasing his hardening cock. She knew he was close, his breath coming in ragged gasps, his hips twitching slightly, trying to chase the sensation. She tutted, "None of that, little princess. You don't get to move until I say so." She circled his nipples with the tip of the crop, watching them harden even more. She leaned down, her tongue replacing the leather, tracing the sensitive peaks. She felt his breath hitch, his body tensing. She paused, blowing a soft breath across his wet nipples, making them pucker even more. She relished the sight of his body humiliated in lace and ruffles while he still had an arousal going on. She dragged the crop lower, tracing the waistband of his panties. She hooked it under the lace, slowly inching it down, revealing his smooth hip bones, his quivering stomach, and finally, his straining cock. She clicked her tongue, "Look at this. All hard and ready for me. But you know what, little sissy? You're not ready for me yet." Ryan let out a whimper, his body shaking with the effort of holding back. Kendra laughed, a low, throaty sound. She wrapped her gloved hand around his cock, stroking him slowly, her touch firm and demanding. She leaned down, her breath hot on his ear. "You want to cum, don't you, little princess? You want to shoot your load all over my hand?" She paused, her stroke slowing to a torturous pace. "But you can't. Not until I say so. Not until I've had my fill of you." She increased her pace, her hand moving faster, her grip tighter. She watched his face, his eyes screwed shut, his mouth open in a silent cry. She leaned down, her tongue tracing his lips, her teeth nipping at his chin. "Open your eyes, little sissy. Look at me. Look at who's making you feel this way." Ryan's eyes flew open, meeting hers. She saw the struggle in his gaze, the battle between humiliation and lust. She smiled, her hand never stopping its tormenting rhythm. "Good boy," she purred. "Now, let's see how long you can last. Let's see how long you can hold back your orgasm for me."

Kendra starts giving Ryan the best Blowjob ever. she's amazed at how long he's been holding his orgasm for her that she allows him to cum in her mouth. Kendra swallows Ryan's cum and love the taste.

Ryan's breath came in desperate heaves, his body taut as a wire, as Kendra's eyes locked onto his. She smirked, knowing she had him right where she wanted him. Slowly, she released his cock from her grip, making him whimper at the sudden absence of touch. She chuckled, a low, husky sound, as she moved down his body. He tensed and his eyes widened when her gloved fingers hooked into the sides of his panties pulling them all the way down, discarding them to the floor. Her mouth followed the path of the crop, tracing his inner thighs, his hips, his stomach, each touch electric, each breath hotter than the last. He felt her hot breath against the sensitive skin of his inner thigh, and he shivered. She looked up at him, her eyes gleaming with lust and dominance. She grabbed his ass, pulling him to the edge of the chair, and she pushed his thighs down to spread him wide. Then her lips, soft and warm, wrapped around the head of his cock, taking him into the wet heat of her mouth. He let out a choked cry, his hips jerking slightly, as her tongue swirled around his sensitive flesh. She took him deeper, her mouth working him with expert precision, her Suction strong and relentless. Her fingers dug into his thighs, holding him in place as she bobbed her head, taking him deeper and deeper with each pass. She hummed softly, the vibration sending shockwaves of pleasure through his body. His hips bucked, trying to chase more of that incredible sensation. She pulled off him with a pop, looking up at him with a wicked grin. "Greedy little slut, aren't you?" she purred, before taking him back into her mouth, this time going even deeper, her nose brushing against his pubic bone. She worked him relentlessly, her mouth, her tongue, her lips driving him higher and higher. He could feel the pressure building, his body tensing, his breath coming in ragged gasps. He was so close, so fucking close. She could feel it too, her eyes watering slightly as she deep-throated him, her gag reflex non-existent as she took him fully. She pulled off him with a gasp, looking up at him with a surprised expression. "Fuck, Ryan," she panted, "you've been holding out on me. You've been holding your orgasm for so long." She grinned, her eyes gleaming with lust and approval. "I think you deserve a reward, little sissy." She took him back into her mouth, her head bobbing faster, her suctions stronger. She could feel his body tensing, his cock throbbing, his breath coming in desperate gasps. And then, with a choked cry, he came, his hips bucking as he released into her mouth. She swallowed him greedily, her eyes rolling back slightly at the taste of him. She moaned softly, her tongue licking him clean, her mouth milking him for every last drop. She pulled off him with a pop, a satisfied grin on her face. "Mmm," she purred, licking her lips. "You taste delicious, little sissy. I think I might just keep you around for that alone." Kendra looked up at Ryan with a wicked grin. “That was the best blowjob you’ve ever had, you filthy little sissy slut. And now I’m going to ride you. I’m going to ride your cock so hard and deep that you’ll forget your own name. You’re going to cum so hard that you’ll see stars. And then, maybe, just maybe, I’ll let you cum again. But only if you’re good. Only if you’re my good little sissy slut.”

Kendra stood just out of reach, stripping off her own clothes, her movements deliberate, designed to tease. She watched Ryan's eyes follow her every move, his breath still coming in ragged gasps, his cock already starting to twitch with renewed interest. She smirked, enjoying his eagerness. She grabbed a pair of handcuffs from the bedside table and tossed them to him. “Put these on, little sissy. I want you to watch while I take what I want from you.” Ryan fumbled with the cold metal, his hands shaking slightly as he secured them around his wrists. Kendra nodded in approval, circling him like a predator. She straddled him, her knees pressing into the armrests of the chair, her wet pussy lips brushing against the tip of his cock. She leaned down, her breasts pressing against his chest, her lips brushing against his ear. “You like this, don’t you, little princess?” she whispered. “You like being used. You like being my little fuck toy.” She sat up, her hands gripping his shoulders for leverage. She rubbed the head of his cock against her slit, coating him in her juices. She gasped slightly, her eyes fluttering closed as she savored the sensation. She looked down at him, her eyes gleaming with lust and dominance and her voice husky. “Watch me, little sissy. Watch me take what’s mine.” She impaled herself on him, her body taking him inch by inch, her mouth open in a silent cry of pleasure. She began to move, her hips rolling, her body undulating, taking him deeper and deeper with each pass. Her fingers dug into his shoulders, her nails leaving half-moon marks on his skin. She rode him hard, her body slapping against his, her breath coming in ragged gasps. She leaned down, her lips brushing against his. “You feel so good inside me, little sissy,” she purred. “You fill me so perfectly.” Her tongue darted out, tracing his lips, her teeth nipping at his chin. “But you know what? I want more. I want you to cum for me. I want you to fill me up. Can you do that for me, little sissy? Can you cum for me?” She sat up, her hands gripping his knees, her body moving faster, her breath coming in desperate gasps. “Cum for me, little sissy,” she demanded. “Cum for me. Now.”

Ryan's breath hitched as Kendra's demands echoed in his mind. He felt his body responding, his cock throbbing inside her, eager to obey. Kendra's eyes never left his, her gaze intense and commanding. She reached between them, her fingers finding his balls, rolling and squeezing them gently. The sensation sent a jolt of pleasure through his body, pushing him closer to the edge. Kendra's movements became more frantic, her hips grinding against him, her breath coming in short, sharp gasps. She leaned down, her lips pressing against his in a fierce, hungry kiss. Her tongue invaded his mouth, claiming him, dominating him. He moaned into her kiss, his body tensing, his cock throbbing. "Cum with me, little sissy," she growled against his lips. "Cum with me now." Her words were his undoing. With a choked cry, he felt his orgasm rip through him, his cock pulsing as he released deep inside her. Kendra's body tensed, her nails digging into his knees, her breath catching in her throat. She threw her head back, a cry of pleasure ripping from her lips as she came, her body convulsing around him. They rode out their orgasms together, their bodies slick with sweat, their breath mingling, their eyes locked. As the intensity of their climaxes began to ebb, Kendra collapsed against him, her body shaking with the aftershocks. She pressed soft, gentle kisses against his neck, his jaw, his lips. He could feel her heart pounding in her chest, matching the rhythm of his own. She looked down at him, a soft smile playing on her lips. "Good boy," she whispered, her voice husky with satisfaction. "That was perfect." She sat up, her body still straddling his, and she leaned down to kiss him softly. "You did so well, little sissy. You took it like a champ." She licked his lips, suckling them into her mouth before releasing them. "I think you deserve a little reward. What do you want, little sissy? What do you need?"