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Chapter 14
by
CuriouslyWatching
What does Holly wish for?
To get Fucked by her Mistress
Harry's eyes widened in pure wonder, anything he wanted? Yet the first thought that entered his mind wasn't acquiring his freedom. Or even getting some clothes of his own, or getting to replace the stiletto heels that had grown to a staggering six inches, or getting out of any of the humiliations he suffered on a daily basis. No, the very first thought was the one that had been haunting his mind since the first time she showed him her cock, the quick comment she made about fucking him.
He had fantasized and dreamt of that moment, many of dreams filled with incredible scenarios where she took him. His weeks of training showed now, because he displayed absolutely no hesitation, having been taught to not mumble or fiddle, as those were things Mistress Bellatrix didn't tolerate. Before his mind could even catch up he blurted out his deepest wish, "please fuck me Mistress!"
He blushed bright red as he realized what he had said, yet Mistress Bellatrix's smile just widened as she slowly started pumping her long cock, spreading her juices and his spit all over it. Harry was mesmerized by the way the wetness made it glisten in the faint light.
"Is that your wish Holly?" she murmured, "To have my big fat cock plunder that needy little hole of yours?"
Harry felt his sphincter clench around the plug, horny beyond belief. “Yes Mistress!" he gasped, quickly adding a, “please!"
"Well, you have been such a good girl..." she purred, her eyes shining with amusement as she looked down at him. She stopped pumping her cock, leaning back on the bed before gesturing towards her glistening flagpole, "why don't you climb aboard and show me how well you can please your Mistress with your greedy little hole?"
Harry needed no further encouragement, quickly climbing up on the bed. He blushed as he realized he needed to present his butt to her first so she could remove the pink plug, not being able to touch it himself. Bending over he lifted up his skirt and pulled aside his panties, presenting himself for Mistress Bellatrix. She wasted no time grabbing it and pulling on it steadily, slowly pulling it out of his firm grip. He groaned softly as it popped free, feeling so very empty as his ring clenched around thin air for the first time in weeks.
Not wanting to keep his Mistress waiting, or himself for that matter, he carefully straddled her waist, having to stand up high on his knees to make room for her long thick shaft. His fumbling hand quickly found her fat meat, bringing the hot wet tip to his pulsing slick rosebud. It felt absolutely massive as he slowly pressed down on it, for a moment wondering if it even could fit.
That moment passed when he felt himself stretch more than he ever had before, slowly making room for the big round mushroom head. He wasn't sure if he was moaning in pain or pleasure as he was stretched to the very limits, before suddenly sinking down a couple of inches as it popped past his only defense. The sensation of having her finally breach his anus was too much, the huge size of her fat babymaker practically crushed his prostate as it made room for itself, making him squeal loudly as he spurted a wet messy load into his panties.
"I'm sorry Mistress!" he moaned over and over again as he spurted jet after jet of cum into the small piece of cloth that barely hid his cock cage, unable to stop his orgasm.
Mistress Bellatrix chuckled, her hand rubbing against his blushing cheek, "aww, don't worry baby, you never have to apologize for loving your Mistress."
Loving her? Did he really love her? He knew that some part of him certainly adored her, but was it love? That sounded a bit far-fetched. He wasn't sure and didn't have time to contemplate on it as Mistress Bellatrix grabbed his round soft hips and started pushing him down, her monstrous cock sinking into places he had never been touched before. He knew the sounds he let out must have sounded absolutely whorish, yet she only seemed amused by his reaction, pushing him ever deeper.
Whenever it felt like it would go no deeper she would slowly pump him up down for a moment before slipping past whatever blockage her fat round meaty explorer had encountered. Harry had no control and little awareness of what was going on around him, panting heavily as he rested his hands on both sides of her shoulders while she steadily stretched his colon to dimensions it had never experienced before.
The heavy pressure in anus reminded him he needed to relax, a strangled groan slipping out as Bellatrix pushed down even harder. "Come on Holly, you're a big girl, you can do it,” she murmured as she urged him down on her massive prick.
"Mistress.." he mumbled, feeling completely stuffed, yet knowing there was still more to go.
"Shush, just a little more,” she cooed, a wide smirk on her face as she watched his half pained expression. He gasped loudly when he finally felt her smooth skin under his butt, realizing she was finally buried to the balls in his poor anus. The feeling of being so completely full and stretched by his Mistress was too much for him, making him cum again into the soaked flimsy cloth that barely hid the restricting cage he wore. His feminine moan of pleasure made Bellatrix's cock twitch inside him, enjoying the way his insides spasmed and milked around her.
"Such a slutty little girl," she grinned, "completely in love with my fat cock."
Harry made no attempts to deny it, especially when she started slowly pumping him in her lap, lifting him higher between every thrust. A steady stream of fluid was leaking out of his constricted cock, unable to handle the feeling of his prostate being absolutely crushed by the huge log of meat rearranging his insides. Her fat cock was pumping him full of precum, making their coupling slick and wet, and above all loud. The slurping sound of the massive shaft plunging into his rosebud was obscene, yet even that couldn't compete with his whorish wailing as he happily rode her, not even needing her arms to guide him anymore.
"Do you love it Holly?" she asked, raising her hips to meet his butt with a wet slap.
"I love it Mistress!" he gasped, stars appearing before his eyes as his entire existence seemed to revolve around the fat hot spermcannon pulsing inside of him.
"Talk to me girl, tell me how you feel!" she ordered.
"I love it, I love it, I love it! I love your fat cock Mistress!" he squealed.
Bellatrix's grin was wide on her face, lifting him all the way to the very tip before plunging him down all the way to the hilt, laughing at the delirious look on his face. She noted that the fluid leaking into his panties was clear, meaning he had absolutely nothing left to shoot, yet was still being continuously milked by her hot meat. She wondered if he even had any idea what his body was doing anymore, watching the way he ground his hips against her cock in needy desperation.
"Who loves my fat cock?" Bellatrix asked, eagerly awaiting the answer.
"Holly loves your cock! Ahh, Holly is the happiest girl in the world!" the boy moaned, making her own balls churn. Knowing that he was finally completely hers pushed her over the limit, knowing that she would spend years bending her little pet over at any time she wished, watching him moan and beg as she plundered his cute little bubble butt.
"Nnnngghhh!" Bellatrix groaned, holding Harry down to her crotch, doing her best to prevent him from moving as she felt her own load explode inside of him.
Holly felt a hot wet sensation bloom in his body, understanding that her Mistress was cumming inside her. The thought made her spasm in her lap, clenching her sphincter to do her very best to milk her dry. Her belly was swelling as more and more of the creamy treat flooded her, feeling it surge around her intestines as the massive grape sized balls shot jet after jet of her gift inside of her.
A part of Holly was disappointed that she wouldn't get to taste it, although maybe Mistress would allow her to clean her afterwards. The thought turned her on even more, her hands caressing her swelling belly. She gurgled in pleasure, looking like her Mistress had just impregnated her. She knew she had a fucked silly expression on her face, panting loudly as a sliver of drool ran down her lips, but she couldn't find it in herself to care, because she knew she was serving her Mistress.
"Ahhh, good girl." Mistress moaned, caressing her hips. Holly smiled, happy that she was pleasing her. Mistress Bellatrix pulled her down into a deep kiss, something that was a bit uncomfortable because of her bulging belly, but the feeling of kissing her overrode any discomfort. She loved her Mistress so much.
Bellatrix slowly pushed her to the side, her fat cock slipping out of her obscenely stretched hole with a wet slurp. Holly had a dazed expression on her face as she tried to recover her breath, watching as her Mistress walked over to the window, using her wand to send a spell into the darkness.
"What are you doing Mistress?" she mumbled, forgetting for a second that she shouldn't pry.
Bellatrix didn't seem upset though, instead smirking victoriously at her willing ****, “just letting my master know that Holly is a good girl." Pausing, she continued, "I'll have a surprise waiting for you tomorrow in the morning. Bring it with you when once your done getting dressed."
Holly softly squealed in happiness, even though she was tired, she knew she was so lucky to end up with such a kind Mistress. After being dismissed, she wobbled down the hallway, only having enough energy to shut the door behind her before she slumped onto her bed and fell asleep.
What present did Bellatrix leave?
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Harry Potter: Sissy Situations
Harry's Journey as a Sissy Slut
Harry Potter always has trouble being stumbled upon by a wide variety of different people who all have a similar goal: turn Harry into their own personal sissy slut.
Updated on May 22, 2026
by CuriouslyWatching
Created on Nov 27, 2021
by CuriouslyWatching
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