Chapter 11: Sissy
They were celebrating her victory, and Mary couldn't help but feel a rush of excitement as she basked in their praise. They talked about their experiences with dominance and submission, exchanging stories and ideas about what they liked to do in the bedroom. Mary couldn't wait to explore some of these new ideas with Casey, who was nursing a drink off to the side. As they chatted, Mary's eyes keeps wandering over to Claire's mom. She was a beautiful woman, with wide hips and a huge ass. She loved to have men worship her feet, pussy, and ass. When she sat on their face, her ass was so big, it swallowed their whole head. "What do you think we should do next?
Mary asked, her eyes still lingering on Claire's mom. The other women followed her gaze, appreciative murmurs filling the room.
Claire's mom, noticing the attention, smirked. "Well, since you all seem to be enjoying yourselves, how about we give poor Casey here a break and find someone else to play with? Lets have Casey lay under our table so we have a place to put our feet while I make a call."
The room erupted in agreement, and all eyes turned to Kim. She grinned, her massive body shifting in her seat. "I have just the person in mind."
She pulled out her phone, scrolling through her contacts before putting it on speaker. A gruff voice answered on the third ring.
"Yeah?"
"It's Kim," she said, her voice a low purr. "I've got a situation here. We need a fresh toy to play with."
There was a pause, then a chuckle. "You always do, don't you? Alright, I've got just the thing. Little guy, huge cock, and stupid. Perfect for your games."
Kim grinned, her eyes gleaming with anticipation. "Send him over. We'll be waiting."
She ended the call, turning to the others. "He'll be here in a couple hours. Daniella looked over at Casey "Get over here and lay under our table , worm. We're going to put our feet on you while we wait." Casey, still nursing his ruined balls, limped over and laid down under the table. The women all put their feet on him - his face, his chest, and especially his balls. They discussed their plans for the night which included dressing Casey up like a girl, restraining him, and having the new guy fuck his mouth thinking he is a woman.
They also decided to make him wear a gag that resembled a vagina so he would feel even more humiliated. Mary suggested that they should also make him wear a butt plug to prepare him for later activities. Everyone agreed, and they set to work preparing for the night's festivities.
Meanwhile, Casey lay under the table, the women's feet pressing into him, their heels digging into his flesh. He could feel their weight, their power, and it made his cock twitch despite the pain in his balls. He looked up, seeing their silhouettes through the tablecloth, their laughter echoing above him.
He felt a mix of humiliation and excitement, his cock hardening despite the pain in his balls. He could feel their feet moving, caressing his body, their heels digging into his flesh. He closed his eyes, imagining their bodies, their curves, their desires.
Suddenly, the doorbell rang, and the room fell silent. Kim stood up, her chair scraping against the floor. "That must be our new toy," she said, her voice a low growl. Casey heard footsteps, the sound of the door opening, and then a muffled voice.
"Come in, darling," Kim purred. It was Ashley. Ashley walked in and sat at the table. She noticed Casey's erection and decided to wrap her toes around it while they discussed his transformation . She started to stroke him gently, making him moan softly. The women watched as Ashley played with Casey's cock, their eyes gleaming with lust. Claire's mom - Daniella said, "we should have him lick all of us under the table when Ashley is finished with him ."
Ashley nodded, her grip tightening on Casey's cock. "Sounds like a plan. Let's get this worm nice and ready for us."
Ashley leaned down, her massive breasts hanging over the table, her nipples brushing against Casey's chest. She brought her face close to his, her breath hot on his lips. "You like that, don't you, worm? You like having my foot on your pathetic little cock?"
Casey could only nod, his breath coming in short gasps. Ashley smiled, her teeth glinting in the dim light. "Good boy. Should I let you cum before you worship all of us under this table as we sit comfortably in our chairs?
Or should I make you suffer a bit longer?" Ashley teased, her toes still wrapped around Casey's throbbing cock. She could feel it pulsing, eager for release, and it made her smile wickedly.
"Please, Mistress Ashley," Casey begged, his voice barely above a whisper. "Let me cum now."
Ashley chuckled, a low, throaty sound that sent shivers down Casey's spine. "Alright, worm. But only because I'm feeling generous today." She increased the pressure of her toes, stroking him faster, her grip tight around his shaft.
Casey's breath hitched, his hips bucking slightly as he tried to fuck her foot. Ashley smirked, loving the control she had over him. Fuck my foot. Show me how much you want to cum."
Casey obeyed, his hips moving in rhythm with her strokes, his cock throbbing in her grasp. He could feel his orgasm building, his balls tightening, his breath coming in short gasps. Ashley could feel it too, her toes sensing the change in his cock.
"Cum for me, worm," she commanded, her voice a low growl.
"Show me how much you love my foot on your pathetic little cock."
Casey's hips bucked, his cock throbbing in Ashley's grip. "Yes, Mistress Ashley," he moaned. "I'm gonna cum. I'm gonna cum on your foot."
Ashley's grip tightened, her toes digging into his flesh as she stroked him faster. "That's right, worm. Cum for me. Cum all over my toes so I can stick them in your mouth!
Ashley demanded, her voice dripping with authority. Casey could only whimper in response, his body tensing as he felt his orgasm approaching. Ashley's toes dug into his flesh, her grip on his cock tightening as she stroked him faster and faster.
"Oh fuck, oh fuck, oh fuck!" Casey cried out, his hips bucking wildly as he came undone. His cock pulsed in Ashley's grip, spurt after spurt of hot cum shooting out and coating her toes. Ashley moaned in delight, watching as Casey's cum dripped down her foot, her toes still wrapped tightly around his shaft.
She brought her foot up to his face , smearing his cum all over his cheeks and lips. "Lick it clean, worm," she ordered, her voice stern. Casey hesitantly stuck out his tongue, tasting his own salty essence. Ashley pushed her foot harder against his face, rubbing his cum into his skin. "Every last drop, worm. Don't waste any."
Casey obediently licked and sucked at her foot, cleaning every bit of cum he could find. Ashley watched him, her pussy throbbing with desire. She couldn't wait to feel his tongue on her, to use him for her own pleasure. She lifted her skirt, pulled off her underwear, and hooked her foot behind his head and pulled his face between her legs . "Eat me, worm," she commanded, grinding her pussy against his mouth. Casey could feel her wetness, smell her musk, taste her tangy juices. He lapped at her greedily, his tongue exploring her folds, finding her huge clit and sucking it into his mouth. Ashley moaned, her hips bucking against his face, riding his tongue like a cock. "Fuck yes, worm. Eat my pussy. Make me cum."
Casey's tongue worked feverishly, flicking and licking, sucking and biting.
Ashley's moans grew louder, her hips bucking harder against his face. He could feel her getting closer, her pussy flooding his mouth with her juices. He reached up, spreading her lips apart, exposing her clit completely. He latched onto it, sucking hard, his tongue flicking back and forth.
"Fuck, yes! Right there, worm!" Ashley screamed, her fingers tangled in his hair, pulling him tighter against her. Casey could barely breathe, but he didn't care. He wanted to make her cum, to taste her orgasm on his tongue.
He could feel her body tensing, her breath coming in short gasps. He knew she was close. He slipped two fingers inside her, curling them upwards, rubbing against her G-spot as he continued to suck on her clit.
"Shit, yes! Just like that, worm!" Ashley moaned, her hips bucking against his face. He could feel her pussy clamping down on his fingers, her juices flowing freely. He lapped them up, greedy for more.
"I'm gonna cum, worm.
I'm gonna fucking cum all over your face," Ashley growled, her hips bucking wildly. Casey could feel her body tensing, her pussy clamping down on his fingers. He redoubled his efforts, wanting nothing more than to taste her orgasm.
"Fuck yeah, make me cum, worm!" Ashley screamed, her body convulsing as she came undone. Her pussy flooded his mouth, her juices dripping down his chin. Casey lapped it up, greedy for every last drop. Ashley collapsed back in her chair, panting, her body covered in a thin sheen of sweat.
"That was...
fucking incredible," Ashley panted, her massive breasts heaving as she caught her breath. Casey, his face soaked with Ashley's juices, looked up at her with adoration. "Thank you, Mistress Ashley," he whispered, his voice hoarse from exertion. Ashley smirked, her eyes gleaming with lust. "You did well, worm. Now, let's see if you can handle the rest of us." She gestured to the other women, who were already shifting in their seats, their eyes filled with hunger.
Time to show us what you're made of. Crawl under the table and start with me."
Casey, still buzzing from Ashley's orgasm, eagerly complied. He crawled under the table, his eyes adjusting to the dim light. He could see the outline of Mary's massive thighs, her feet dangling tantalizingly close to his face. He reached out, running his hands up her calves, feeling the smooth, soft skin.
"Start with my feet, worm," Mary commanded, her voice a low purr. Casey nodded, bringing his face to her soles.
He kissed them gently, his tongue snaking out to taste her skin. Mary moaned softly, her body relaxing as he worshipped her feet. He ran his tongue along her arches, sucking on her toes, one by one. He could feel her heels digging into his back, urging him on.
"Use your tongue, worm," Mary growled, her voice thick with desire. "Lick my feet like they're my pussy."
Casey obeyed, flattening his tongue and running it up and down her soles, paying special attention to the sensitive spots.
Mary's moans grew louder, her hips shifting in her seat. Casey could feel her arousal, her scent filling his nostrils, making his cock throb. He wanted more, needed more.
"Enough with the feet, worm," Mary commanded, her voice ragged with desire. "Crawl up here and eat my pussy."
Casey didn't need to be told twice. He scrambled up her body, his hands gripping her thighs, pushing them apart. Mary's pussy was glistening, her lips swollen and inviting.
Casey could smell her musk, rich and intoxicating, making his mouth water. He dove in, his tongue lapping at her folds, tasting her sweet nectar. Mary's hips bucked, her hands tangling in his hair, pulling him closer. Eat my pussy, worm," she growled, her voice dripping with lust. Casey obliged, his tongue exploring every inch of her, flicking against her clit, delving into her entrance. He could feel her getting wetter, her juices coating his chin, dripping down his neck.
He lapped them up, greedy for more, his tongue working feverishly to bring her to the brink. Mary's moans grew louder, her hips bucking against his face, riding his tongue like a cock. she screamed, her fingers tangled in his hair, pulling him tighter against her. Casey could feel her body tensing, her breath coming in short gasps.
Mary screamed, her hips bucking against his face. I'm gonna fucking cum all over your face," Mary growled, her hips bucking wildly.
Mary screamed, her body convulsing as she came undone. Mary collapsed back in her chair, panting, her body covered in a thin sheen of sweat.
"That was... fucking incredible," Mary panted, her massive breasts heaving as she caught her breath.
Casey, his face drenched in Mary's juices, looked up at her with reverence. "Thank you, Mistress Mary," he whispered, his voice hoarse from exertion. Mary smirked, her eyes gleaming with lust. "You're welcome, worm.
Casey, still buzzing from Mary's orgasm, eagerly moved on to the next pair of feet.
He looked up to see Claire's mom, Daniella, smiling down at him, her massive thighs spread wide. "Come here, worm," she purred, her voice dripping with honey. "I want to feel that tongue on my pussy." He crawled up her body, his hands gripping her thighs, pushing them wider. Daniella's pussy was a sight to behold - plump lips glistening with arousal, a thick bush of dark curls, and a scent that made his mouth water.
Casey wasted no time, diving in like a starving man at a feast. He lapped at her folds, his tongue exploring every inch of her, from her entrance to her clit. Daniella moaned, her hips bucking against his face, her fingers tangling in his hair.
"Fuck, yes, worm," she groaned, her voice thick with desire. "Eat my pussy like you mean it."
Casey did just that, his tongue working feverishly, flicking and licking, sucking and biting.
Daniella's moans grew louder, her hips bucking harder against his face. Daniella screamed, her fingers tangled in his hair, pulling him tighter against her.
Just like that, worm! Make me cum all over your face!"
Casey could feel her body tensing, her pussy clamping down on his tongue. Daniella moaned, her hips bucking against his face.
"Fuck, yes, worm. Just like that. Make me cum all over your face." Casey's tongue flicked and licked, his nose buried in her curls, breathing in her musk. He could feel her getting closer, her pussy pulsing against his tongue.
Daniella screamed, her hips bucking against his face. Daniella moaned, her hips bucking wildly.
"Fuck, yes, worm! Keep going! I'm almost there!" Casey redoubled his efforts, his tongue lashing against her clit, his fingers pumping in and out of her pussy. He slipped a third finger inside her, stretching her tight hole, and curled them upwards, rubbing against her G-spot. "Oh, fuck! Yes! Right there!" Daniella gasped, her body trembling. Casey could feel her pussy clamping down on his fingers, her juices flowing freely. He latched onto her clit, sucking hard, his tongue flicking back and forth. That was all it took. Daniella screamed, her body convulsing as she came undone. Casey lapped them up, greedy for every last drop. Daniella collapsed back in her chair, panting, her body covered in a thin sheen of sweat.
Casey, his face drenched in her juices, looked up at her with adoration. "Thank you, Mistress Daniella," he whispered, his voice hoarse from exertion. Daniella smirked, her eyes gleaming with lust. But don't think you're done yet. There are still plenty of pussies left to eat."
Casey eagerly moved on to the next pair of feet, looking up to see Kim grinning down at him, her massive thighs spread wide. "Hey there, worm," she purred, her voice a low rumble.
"You ready to take on this big ol' pussy?" Casey looked up at Kim, his eyes wide with awe and apprehension. Her thighs were massive, her pussy a vast expanse of glistening flesh, her scent overwhelming. He nodded, his mouth dry, and crawled up her body, his hands shaking as he gripped her thighs.
"Go on, worm," Kim urged, her voice thick with desire. "Eat my pussy. Casey leaned in, his tongue tentatively touching her folds.
Kim's pussy was a symphony of flavors - sweet, tangy, and musky, all rolled into one. He explored her slowly, his tongue tracing her labia, dipping into her entrance, and finally finding her clit. Kim moaned, her hips shifting, encouraging him to continue.
"Fuck, yes, worm," she growled. Kim's moans grew louder, her hips bucking harder against his face.
Casey could feel her getting close, her pussy pulsing against his tongue. He slipped two fingers inside her, curling them upwards, rubbing against her G-spot. Kim screamed, her fingers tangled in his hair, pulling him tighter against her. He redoubled his efforts, his tongue lashing against her clit, his fingers pumping in and out of her pussy.
Kim's moans filled the room, her body writhing against his face. Just like that! Kim gasped, her body trembling.
Casey could feel her pussy pulsing, her juices flowing freely.
Kim's moans grew louder, her hips bucking against his face, riding his tongue like a cock. Kim growled, her voice dripping with lust. "Make me cum all over your face!" Kim roared, her massive body trembling. Casey's tongue flicked and licked, his fingers pumping in and out of her pussy, determined to make her explode. He could feel her getting closer, her pussy pulsing against his tongue, her juices flowing freely. Kim screamed, her hips bucking wildly.
Kim's moans grew louder, her body trembling, her fingers pulling his hair so hard it hurt. Oh, fuck! I'm gonna cum, worm! I'm gonna fucking cum all over your face!" Kim roared, her massive body trembling.
Casey braced himself, his tongue lashing against her clit, his fingers curling upwards, rubbing against her G-spot.
Kim's body tensed, her pussy clamping down on his fingers, her juices flowing freely. He could feel her orgasm building, her body trembling, her moans growing louder. Make me cum!" Kim bellowed, her massive body quivering. Casey's tongue lashed against her clit, his fingers curling upwards, rubbing against her G-spot. He could feel her orgasm building, her body tensing, her pussy clamping down on his fingers. He wanted to make her cum so hard, he wanted to feel her juices gushing onto his face, he wanted to taste her ecstasy. Kim roared, her hips bucking wildly, her massive body quivering as she came all over his face . Her pussy pulsed, her juices flowing freely, coating his tongue, his chin, his cheeks. Casey lapped it up, greedy for every last drop, his cock throbbing at the taste of her.
"Fuck, yes, worm!" Kim bellowed, her body collapsing back in her chair, spent. "You made me fucking cum so hard."
Casey, his face drenched in Kim's juices, looked up at her with pride. "Thank you, Mistress Kim," he whispered, his voice hoarse from exertion.
Casey eagerly moved on to the next pair of feet, looking up to see Courtney
, the Amazonian bodybuilder, smirking down at him. Her thighs were like tree trunks, her pussy a tight slit between powerful legs. He gulped, his heart pounding in his chest.
"Well, worm," Courtney taunted, her voice a deep, husky growl. "You gonna eat my pussy or what?"
Casey nodded, crawling up her body, his hands trembling as he gripped her thighs. He could feel the power in her legs, the strength that could crush him with ease. It both terrified and excited him.
He leaned in, his tongue tentatively touching her folds.
Courtney's pussy was a tight, velvety vise, her scent intoxicating. Courtney moaned, her hips shifting, encouraging him to continue.
Casey's tongue flicked and licked, his fingers spreading her lips apart, exposing her clit fully. He sucked it into his mouth, his tongue lashing against it, feeling it pulse and swell.
Courtney's moans grew louder, her hips bucking against his face. Suck my clit.
Casey's fingers found her entrance, slipping inside easily, her pussy dripping with arousal. He pumped them in and out, his tongue never leaving her clit, his other hand reaching up to squeeze her breast, feeling the weight of it in his palm.
Courtney's body tensed, her breath coming in short gasps. "Fuck, yes. Don't stop, worm.
Make me cum all over your face," Courtney growled, her voice dripping with lust. Casey's fingers pumped in and out of her pussy, his tongue lashing against her clit, his other hand squeezing her breast, pinching her nipple. He could feel her body tensing, her pussy clamping down on his fingers, her breath coming in short gasps. Harder, worm. Fuck me harder with your fingers," Courtney demanded, her hips bucking against his face.
Casey obliged, adding a third finger, stretching her tight pussy, pumping them in and out with increasing speed. He could feel her juices coating his hand, hear the wet slapping sounds of his fingers fucking her.
"Yeah, that's it, worm. Fuck my pussy with your fingers," Courtney growled, her voice thick with desire. "But don't you dare make me cum yet. Not until I say so."
Casey nodded, his tongue still lashing against her clit, his fingers fucking her hard and fast.
But he held back, waiting for her command.
Courtney's body writhed against his face, her moans filling the room. "Fuck, worm. You're doing so good. But I want more. I want to feel your tongue inside me."
Casey's eyes widened, but he didn't hesitate. He slipped his fingers out of her pussy and replaced them with his tongue, pushing it deep inside her, tasting her, feeling her walls clamp down around it.
Courtney moaned, her hips bucking against his face, riding his tongue like a cock. Lick me out. Make me cum," she growled, her voice thick with desire.
Casey's tongue explored her, lapping up her juices, tasting her sweet nectar. He could feel her getting closer, her body tensing, her breath coming in short gasps. He slipped a finger back inside her, curling it upwards, rubbing against her G-spot.
Courtney's hips bucked, her body tensing. Right there, worm.
Casey's tongue flicked and licked, his finger pumping in and out of her, his other hand squeezing her breast, pinching her nipple. He could feel her body tensing, her pussy clamping down on his finger, her breath coming in short gasps.
"Harder, worm. Fuck me harder with your tongue ," Courtney demanded, her voice a deep, commanding growl. Casey complied, his tongue plunging in and out of her pussy, his nose pressing against her clit, breathing in her musk. He could feel her body tensing, her pussy clamping down on his tongue, her juices flowing freely. Just like that, worm. Make me cum now," Courtney moaned, her hips bucking hard on his face . I'm gonna cum, worm!" Courtney roared, her body convulsing as she came undone.
Her pussy clamped down on Casey's tongue, her juices gushing out, coating his face. He lapped it up greedily, his cock throbbing at the taste of her. Courtney collapsed back in her chair, panting, her massive body glistening with sweat. You made me cum so fucking hard," she growled, her voice thick with satisfaction. Casey, his face drenched in her juices, looked up at her with pride. "Thank you, Mistress Courtney," he whispered, his voice hoarse from exertion.
But before he could catch his breath, another pair of feet appeared before him under the table. He looked up to see Claire , Mary's best friend, grinning down at him. Her feet were smaller than the others, but no less enticing. Her toenails were painted a bright red, matching her lipstick.
"Hey there, worm," she said, her voice playful. "I've been watching you work your magic on these ladies. Now it's my turn."
Casey felt a surge of excitement. He was nervous remembering how she had kicked his balls 50 times in a row the other day , but he also remembered how much he enjoyed it. He crawled towards her, eager to please.
Claire's pussy was shaved bare, her lips glistening with anticipation. Casey could smell her arousal, a sweet and musky scent that made his mouth water. He reached out, running his hands up her thighs, feeling the smooth, soft skin.
"Spread your legs for me, Claire," he murmured, looking up at her with eager eyes.
Claire smirked, her eyes gleaming with lust. "Make me," she challenged, her voice a low purr.
Casey didn't hesitate.
He grabbed Claire's ankles, pulling her towards him, forcing her legs apart. Claire laughed, a sound that was equal parts surprise and delight. "Feisty little worm, aren't you?" she teased, her eyes sparkling with mischief.
Casey ignored her, burying his face between her legs, his tongue lapping at her folds. Claire gasped, her hips bucking against his face, her laughter turning into moans of pleasure. Eat my pussy, worm," she growled, her fingers tangling in his hair, pulling him closer.
Casey's tongue snaked out, lapping at her folds, tasting her sweet nectar. Claire's pussy was a symphony of flavors - sweet, tangy, and musky, all rolled into one. Claire moaned, her hips shifting, encouraging him to continue.
"Fuck, yes, worm," she gasped, her voice thick with desire. "That feels so fucking good." Claire moaned, grinding her pussy against Casey's face. "Keep eating me out, worm.
Casey's tongue worked overtime, lapping at her clit, fucking her with his fingers. He wanted to make her cum so hard, he wanted to taste her ecstasy.
"Right there, worm. Don't stop," Claire panted, her fingers pulling his hair so hard it hurt.
Casey didn't mind. He loved the pain, loved knowing he was pleasing her. His tongue flicked and licked, his fingers pumping in and out of her pussy, determined to make her explode.
Claire's moans grew louder, her body writhing against his face. I'm so close.
Make me fucking cum!" Claire's voice was a desperate plea, her hips bucking against Casey's face. He could feel her pussy pulsing, her juices flowing freely, coating his tongue, his chin, his cheeks.
Casey's tongue lashed against her clit, his fingers pumping in and out of her pussy, determined to make her explode. She was almost there , her body tensing, her breath coming in short gasps. "Fuck, worm! I'm gonna cum!" Claire cried out, her hips bucking wildly against his face. Casey could feel her pussy pulsing, her juices flowing freely, coating his tongue, his chin, his cheeks. He wanted to taste her, to drink her in, to make her cum so hard she would forget her own name.
Suddenly, Claire's body went rigid, her pussy clamping down on his fingers, her juices gushing out, flooding his mouth.
"Fuck, fuck, fuck!" she screamed, her hips bucking wildly, riding his face, grinding her clit against his tongue. Claire collapsed back in her chair, panting, her body glistening with sweat. "Holy shit, worm," she gasped, her voice barely above a whisper.
Before Casey could even catch his breath, Claire got up and the last pair of feet appeared before him . He looked up to see Bailey, the stunning trans woman, smirking down at him. Her massive cock, already rock hard, hung heavy between her legs, swaying slightly as she shifted her stance.
"Alright, worm," she said, her voice a deep, sultry growl. "You've had your fun with the girls. Now it's time for some real fun."
Casey gulped, his eyes wide as he took in the sheer size of her cock. It was thicker than his wrist, longer than his forearm, and veined with pulsing arteries.
The head was a plum-sized bulb, slick with precum, and the balls hanging beneath were the size of tennis balls. Casey's mouth watered at the sight, his own cock twitching in his pants. He'd never seen anything like it, never imagined he would be faced with such a monstrous cock. And yet, here he was, on his knees, ready to serve.
Bailey chuckled at his expression, her hand wrapping around her cock, stroking it slowly. "Like what you see, worm?" she taunted, her voice a low purr.
"You gonna suck my cock or what?"
Casey nodded, his mouth dry, his heart pounding in his chest. He reached out, his hands trembling as he wrapped them around Bailey's massive shaft. He couldn't believe how thick it was, how hot it felt in his hands. He looked up at her, seeking guidance.
Bailey smirked, her hand covering his, guiding him to stroke her cock. "That's it, worm. Get me nice and hard."
Casey obeyed, his hands working in tandem, stroking her cock, feeling it throb and pulse in his grip.
Bailey's smirk turned into a moan, her hips shifting, fucking her cock into his hands. Now, I want you to put those pretty little lips around my cock and suck it like a good little slut."
Casey's stomach fluttered at her words, but he didn't hesitate. He leaned in, opening his mouth wide, taking the head of her cock between his lips. He could taste the salty sweetness of her precum, could feel the heat of her flesh against his tongue.
He relaxed his jaw, taking more of her length, inch by inch, until he felt the head of her cock hit the back of his throat. He gagged, his eyes watering, but he didn't pull away. Instead, he took a deep breath through his nose and pushed forward, taking her even deeper.
Bailey groaned, her fingers wrapped aroundthe back of his head, holding him in place. Take my cock like a good little slut. Choke on it."
Casey tried to comply, his throat constricting around her thickness, his lungs burning for air.
Bailey's cock was a monster, stretching his mouth wide, filling him completely. He could feel her veins pulsing against his tongue, her precum leaking into his mouth, salty and sweet.
Bailey's grip on his head tightened, her hips thrusting forward, fucking her cock deeper into his throat. "Take it, worm," she growled, her voice thick with lust. "Take my cock like a good little slut."
Casey gagged again, tears streaming down his face, spit dripping from his chin. He could feel his own cock straining against his pants, leaking precome, aching to be touched.
But he knew better than to ask for permission. He was here to serve, to please, and nothing else mattered.
Bailey seemed to read his mind, a wicked grin spreading across her face. You like having my big fat cock in your mouth?"
Casey nodded, his mouth full, his eyes watering. He loved it. He loved the way she tasted, the way she felt, the way she used him.
Bailey pulled him off her cock, allowing him to gasp for air. "Good boy," she praised, her voice a low purr.
"Now, I want you to lick my balls. Show them some love, worm." Casey looked up at her, his eyes wide, but he didn't hesitate. He leaned in, his tongue snaking out, lapping at her massive balls. They were heavy, hanging low, sacking swinging as he licked and sucked. He could taste the saltiness of her skin, the muskiness of her arousal. He took one ball into his mouth, sucking gently, feeling it pulse against his tongue. Bailey moaned, her fingers tangling in his hair, pulling him closer.
"Fuck, yeah, worm. Lick my balls just like that. Show them some love." Casey continued to lavish attention on her massive testicles, switching between licking, sucking, and gently biting. He could feel them swelling in his mouth, growing heavier, more sensitive. Bailey's moans grew louder, her hips shifting, her cock swaying inches from his face. "You're doing so good, worm," she praised, her voice thick with desire. "But I need more. I need you to worship my cock too." Casey looked up at her, his eyes shining with eagerness.
"Yes, Mistress Bailey. What do you want me to do?"
Bailey smirked, her hand still stroking her massive cock. "I want you to worship it, worm. Lick it, kiss it, suck it. Make me feel good."
Casey nodded, leaning in, his tongue snaking out to lap at the underside of her cock. He started at the base, where the thick vein pulsed with life, and worked his way up, tasting every inch of her flesh. Bailey's moans filled the room, her hips shifting, fucking her cock into his mouth.
Casey could feel her getting closer, her body tensing, her breath coming in short gasps. He reached up, his hand wrapping around the base of her cock, stroking it in time with his mouth, feeling it throb and pulse in his grip. You're making me feel so fucking good," Bailey growled, her voice thick with desire. "Keep going.
Casey doubled his efforts, his mouth and hand working in tandem, bringing her closer and closer to the edge. He could feel her body tensing, her cock throbbing in his grip, her breath coming in short gasps. I'm gonna cum," Bailey growled, her fingers tightening in his hair, holding him in place. "And when I do, you're gonna swallow every fucking drop." He wanted nothing more than to taste her, to drink her in, to please her.
Bailey's hips bucked, her cock sliding deep into his throat, hitting the back of his throat, making him gag.
Casey struggled to breathe, tears streaming down his face, but he didn't pull away. He wanted this, needed this. He wanted to please her, to taste her, to feel her cum sliding down his throat. Take my cock like a good little slut," Bailey growled, her voice thick with lust. "Choke on it. Gag on it. Show me how much you love sucking my big fat cock." Bailey commanded, her voice a deep, demanding growl. Casey, eager to please, took her cock deeper into his mouth, his tongue swirling around the head, tasting the salty sweetness of her precum. He could feel her thickness stretching his mouth wide, her veins pulsing against his tongue. Instead, he took her even deeper, his nose pressing against her trimmed pubic hair, inhaling her musky scent.
Bailey groaned, her fingers tangling in his hair, pulling him closer.
That's it. Gag on my cock. Show me how much you love it."
Casey's eyes watered, his throat constricting around her thickness, but he didn't pull away. He wanted to please her, to show her how much he loved sucking her big fat cock.
"Oh, fuck, worm. I'm gonna cum," Bailey growled, her hips bucking, fucking her cock deeper into his throat.
Casey could feel her body tensing, her cock throbbing, her breath coming in short gasps. He wanted to taste her, to drink her in, to please her. He wanted to feel her cum sliding down his throat, to know that he had brought her to this point of ecstasy.
Bailey's fingers tightened in his hair, holding him in place. "Swallow every fucking drop, worm," she commanded, her voice thick with lust. "I wanna feel you choke on my cum."
Casey braced himself, his hands gripping her thighs, his mouth stretched wide around her massive cock.
He could feel the first spurt of cum hitting the back of his throat, hot and salty, coating his tongue. He swallowed instinctively, his throat constricting around her thickness, milking her for every last drop.
Bailey roared, her hips bucking, fucking her cock deeper into his throat, her cum shooting in thick ropes, filling his mouth, overflowing, dripping down his chin, his neck, his chest. Swallow my fucking cum!" she bellowed, her body convulsing, her cock pulsing, her nipples hardening into diamond points.
Milk my fucking cock, worm!"
Casey, his mouth stuffed full of Bailey's massive cock, his throat constricting around her thickness, swallowed every last drop of her cum. He could feel it sliding down his throat, hot and salty, filling him, satisfying him in a way he hadn't known possible.
Bailey, spent, pulled him off her cock, allowing him to gasp for air. He looked up at her, his eyes shining with adoration, his mouth coated in her cum.
"Thank you, Mistress Bailey," he whispered, his voice hoarse from exertion.
Bailey smirked, her hand cupping his chin, wiping the excess cum from his face. "You did good, worm. Real good."
She helped him to his feet, her eyes scanning his body, lingering on the bulge in his pants. "Looks like someone's still hungry," she commented, a wicked grin spreading across her face.
Mary chimed in, "It's time to get him ready for his transformation ."
Claire nodded eagerly, "Let's get him cleaned up first."
They led Casey to the bathroom, stripping him naked along the way. He stood before them, his cock hard and aching, his balls heavy with unspent seed. The women exchanged smirks, enjoying his discomfort.
"On your knees, worm," Mary ordered, pointing to the tile floor.
Casey complied, kneeling before them, his eyes cast downwards. Claire turned on the shower, adjusting the temperature until steam filled the room. Mary grabbed a washcloth, wetting it under the spray, and began to clean Casey's body.
She started at his neck, running the cloth down his chest, circling his nipples, making him shiver. She moved lower, washing his abs, his hips, his thighs, avoiding his cock and balls intentionally. Casey squirmed, his cock throbbing, aching for touch.
"Please, Mistress Mary," he begged, his voice barely above a whisper.
Mary smirked, her eyes gleaming with mischief. "Please what, worm?"
"Please touch me," he pleaded, his eyes locked onto hers.
Mary chuckled, her hand finally wrapping around his cock, giving it a single, firm stroke.
"Is this what you want, worm? My hand around your pathetic little dick?"
Casey whimpered, his hips bucking, fucking his cock into her fist. "Yes, Mistress Mary. Please."
Mary smirked, her hand continuing to stroke him, her grip tight, her pace slow. "You'll have to do better than that, worm. Beg for it. Beg for my touch."
Casey's breath hitched, his eyes locked onto hers. "Please, Mistress Mary. Touch me. Stroke my cock.
Mary laughed and finished cleaning him up , paying extra attention to his balls, rolling them gently in her palm. She stepped back and admired her handiwork. "There, you're all clean now. Ready for your transformation. Let's go make you look like a real girl ," Mary said, leading Casey back to the main room. Claire followed closely behind, her eyes gleaming with curiosity and excitement. They sat Casey down on a stool in front of a large vanity mirror, surrounded by makeup and wigs.
First things first, we need to get rid of that scruff," Mary said, grabbing a razor and shaving cream. She lathered up his face, her hands gentle yet firm, and began to shave him. Casey closed his eyes, enjoying the sensation of her touch, the scrape of the razor against his skin.
Once his face was smooth, Mary turned to the makeup.
She began with foundation, blending it onto his skin with a sponge, creating a flawless canvas. Then came the concealer, hiding any blemishes or imperfections. Next, she applied blush, a soft pink that gave his cheeks a rosy glow. She stepped back, admiring her handiwork, before picking up an eyeliner pencil.
"Close your eyes, worm," she commanded, her voice stern. Casey complied, feeling the tip of the pencil tracing his lash line, creating a sharp, defined edge. Mary filled in his brows, arching them slightly, giving him a feminine, delicate shape.
Then came the mascara, coating his lashes, making them dark and thick. She stepped back, admiring her handiwork, before picking up a lipstick.
"Open up, worm," she ordered, holding the tube to his lips. Casey obeyed, feeling the cool, smooth texture of the lipstick as she traced his lips, painting them a deep, sultry red. She pressed her thumb to his bottom lip, smearing the color, making it look like he'd just been kissed.
"There, that should do it," Mary said, stepping back to survey her work.
Casey blinked his eyes open, staring at his reflection in the mirror. He hardly recognized himself. His face was smooth, his features softened by the makeup, his lips plump and red. He looked like a doll, a pretty little thing, ready to be played with.
Claire whistled, impressed. "Damn, Mary. You've really outdone yourself this time."
Mary smirked, her eyes gleaming with satisfaction. "Why thank you, Claire. But the fun is just beginning."
She turned to Casey, her voice dropping to a low, commanding tone. "Stand up, worm.
Let's get you dressed," Mary ordered, her voice a low, commanding growl. Casey obeyed, rising from the stool, his eyes locked onto hers. Mary held up a silky, black negligee, the fabric shimmering in the dim light. "Arms up," she commanded, and Casey raised his arms, allowing her to slip the garment over his head. The material slid down his body, the cool silk caressing his skin, the cups barely containing his chest, the hem falling just below his ass.
Mary stepped back, admiring her handiwork.
"Fuck, you look good enough to eat," she purred, her eyes raking over Casey's body, lingering on the swell of his ass, the curve of his hips, the way the negligee clung to his every contour. Claire let out a low whistle, her eyes wide with appreciation.
Casey blushed at their compliments, his cock stirring in the confines of the silky fabric. Mary noticed, a wicked grin spreading across her face.
"Let's get you to the bedroom, on your knees, tied helpless to the post, with the vagina gag in your mouth. Let's cage that cock too. We don't want our guest to know you're not a real girl." Mary chuckled, her eyes gleaming with mischief. She snapped her fingers, and Claire handed her a blonde wig, complete with bangs and loose curls. Mary placed it on Casey's head, tucking his hair underneath, arranging the strands until it looked natural. She stepped back, admiring her handiwork. "Perfect," she declared, her voice satisfied. "Now, let's get you to the bedroom."
Casey followed Mary and Claire down the hall, his heart pounding in his chest, his cock throbbing in anticipation.
He could feel the silky negligee caressing his skin, the cool air kissing his ass, the blonde wig tickling his forehead. He felt exposed, vulnerable, and yet, incredibly aroused.
The bedroom was dimly lit, the air thick with the scent of sex and perfume. A four-poster bed dominated the room, the sheets a tangled mess of silk and lace. A sturdy wooden post stood tall at the foot of the bed, a set of leather cuffs attached to its base.
Mary pointed to the post, her voice a low, commanding growl. "On your knees, worm.
Hands behind your back," Mary ordered, her voice leaving no room for argument. Casey complied, sinking to his knees, his hands clasped behind him. Mary produced a length of rope, deftly binding his wrists together, pulling the knot tight enough to bite into his skin. He winced, but said nothing, his eyes locked onto hers.
Next, she retrieved a gag, a silicone contraption designed to look like a pair of plump, red lips. She held it up, showing it to him, a wicked grin spreading across her face.
"This is going to make you look and sound like a real little slut," she said, her voice dripping with disdain. Casey could only nod, his mouth dry, his heart pounding in his chest. Mary approached him, her heels clicking on the hardwood floor, the sound echoing in the silent room. She grabbed his chin, tilting his head up, forcing him to look at her. "Open wide, worm," she commanded, her voice a low growl. Casey obeyed, opening his mouth, feeling the cold silicone of the gag press against his lips.
Mary forced it inside, pushing it to the back of his throat, making him gag. She secured it tightly, the straps pulling at the corners of his mouth, stretching his lips into a lewd, inviting O-shape. He could feel drool already pooling at the corners of his mouth, dripping down his chin, onto his bare chest. "Fuck, you look like a proper little slut now," she said, her voice thick with satisfaction. She turned to Claire, who was watching the scene unfold with wide-eyed fascination.
"Get the cock cage," Mary ordered, her voice a low growl. Claire nodded, hurrying to the closet and returning with a metal device, its purpose clear despite its innocuous appearance. Mary took it from her, holding it up for Casey to see. "This is going to keep that pathetic little cock of yours in check," she sneered, her eyes gleaming with malice. Casey could only whimper, his eyes locked onto the device, his heart pounding in his chest.
Mary knelt before him, her hands deftly fitting the cage around his cock and balls, securing it with a small lock. He could feel the cold metal against his skin, the tight confinement of the cage, the way it squeezed his balls, making them ache. He shifted uncomfortably, but Mary slapped his thigh, hard. "Stay still, worm," she snapped, her voice a low growl. "You're mine to play with now."
With the cage secure, Mary stood, her eyes raking over Casey's bound form.
She grabbed a length of chain connected to the cuffs around his wrists, looping it around the post, and securing it with a padlock. He was now helpless, his arms stretched behind him, his knees digging into the hardwood floor, his cock throbbing in its metal prison.