Ash untied the rope around Officer Jenny's left leg, easing her into a better position. Her legs shifted as she found her balance, still in a bent-over restraint position, her hands and body tightly bound.
Her face was flushed red and damp with sweat. Her muscular frame trembled, a warm trickle of his cum mixed with her own dripped from her, pooling on the floor beneath her.
For a moment, she almost relaxed. Her heavy breaths came out muffled through the gag. "Hmm!" A part of her couldn't deny it felt good.
But her body trembled once again as Ash gripped her firm, curvy ass. He squeezed her buttocks, spreading them slowly to reveal her tight hole twitching nervously under his gaze.
His thumbs teased her soft, pink rim, pressing gently to ease it open.
He exposed her most private spot, her anal hole. It was beautiful: a soft, pink muscle pulsing under his stare, alive and shy, fully exposed in the dim light.
He's seeing everything, Jenny thought, her face burning, heart racing with shy heat. She wanted to scream, "Stop! Haven't you had enough already? You have already taken my virginity... Now you want to do it there too?"
Her bound body shook weakly. She always believed sex was through the vagina only, not anal...
The idea that someone would want to have anal sex, a place she only associated with private bodily functions, felt wrong and confusing. It was a part of herself she never thought anyone would desire or even see.
Ash leaned in close, his breath warm against her most private skin. Jenny shuddered, wanting to scream *No...It's dirty, don't!* but her gag stifled the words.
A faint, musky scent reached him, a mix of sweat and something else. He recognized it immediately.
"Officer Jenny," he said in a teasing tone, "how shameful. I never expected the respected Officer Jenny wouldn't keep her private area clean…"
Jenny's face flushed even deeper. I was on duty all day because of Team Rocket… I was about to go home and take a nice bath when the Pokémon Center incident happened… After that, I never thought I would end up like this. Shame burned through her as excuses piled silently in her mind.
A sly, almost playful smile touched his lips, his eyes amused by her embarrassment. "Don't worry, Officer Jenny," he said lightly. "I'll clean you properly."
Saying this, he pulled out a large syringe from his bag, one about the size of a water bottle, thick and intimidating.
When Jenny heard his words, she was confused. But when she saw what he took out, from between her legs, her face paled before flushing a terrified red. Her legs trembled; desperate, muffled sounds "Hmmmph! Mmmh!" fought against her gag. *No… no, please…*
Ash noticed her fear and spoke gently, "I'm not trying to humiliate you, Officer Jenny. Your asshole is very tight and dry. Let me show you." He pushed a finger into her.
Jenny gasped "mmph~ ~ ~ ~" her body clenching hard around him. Her inner muscles resisted strongly, almost pushing his finger back out.
"See?" he said calmly as he withdrew his finger. "You're too tight. This," he held up the syringe, "will stretch you, clean you, and make you wet inside so I can slip my cock in easily. If I put my cock in now, it'll hurt you. And I don't want to see you in pain," he said softly.
After all, he wasn't sadistic. He didn't enjoy causing pain. He preferred sex where both he and his partner could enjoy themselves.
He filled the syringe with liquid from the milk bottle he had gotten from Pallet Town. He really liked this milk, it had a special chocolate flavor he couldn't quite figure out, but it tasted delicious.
He always kept plenty in his bag. Even Pikachu loved it. The milk lady at the shop truly knew her way.
Although he does have a system function that could modify regular breast milk of Mom into chocolate flavor, it costs 200 points.
Sometimes, he still preferred the normal milk anyway, so he hadn't used this function yet.
Maybe in the future, when he had more points, he would use it on someone else…
His focus returned to Jenny. "Just relax," he said softly. "Try to keep it in. It'll feel good, I promise." He had already tried this on his Mom and Daisy to help stretch them. Both said it felt really good after the initial strange sensation…
Jenny reluctantly gave in. She knew this boy wouldn't stop. Earlier, while he was thrusting inside her, she had noticed another person who looked just like him sitting silently on the bed.
He saw her looking toward the silent figure on the bed, as he continued to thrust inside her. "That's my real body," he explained, his voice strained with effort.
"This is just a clone. It will only last for an hour." He gripped her hips a little tighter, moving faster. "I need to finish before it disappears."
At first, she couldn't believe it. But the more he touched her, his hands gentle as he wiped away her tears, his voice soft as he whispered, You'll understand after five times, the more he explained, the more her resistance wavered.
He didn't explain everything, just enough to slowly build her trust.
And though her body still trembled and her mind raced with doubt, a small part of her began to believe him. Even though she felt terrible, but as an officer she forced herself to stay calm.
She soon came back to her senses as he pressed the syringe tip against her back entrance. Her thoughts snapped back to the present. She clenched her hands, trying to relax as much as possible.
Soon, he pushed the nozzle steadily until it slid fully inside…
He didn't make her wait longer. He pressed the plunger, letting the brown chocolate milk flow inside her. Jenny gasped softly against the gag. The feeling was strange and overwhelming, a cold fullness spreading through her anal canal, something she had never felt before.
Jenny could feel it stretching her lower belly, making it feel heavy and slightly rounded.
He asked smilingly, "How does it feel, Officer Jenny?" as he finished filling her.
Jenny didn't want to admit that the cool, flowing fullness inside her felt strangely soothing, almost pleasant, as it stretched her in a way she'd never experienced. But she refused to respond, staying silent.
Seeing no reaction, he said, "I'm going to let go now, Officer Jenny," he warned softly.
Hearing this, Jenny's eyes widened. If you let go… A mix of fear and shame wXed over her.
He was already prepared; he had placed a bucket beneath her.
At first, Jenny tried to hold back, clenching tightly.
"No need to be embarrassed, Officer Jenny," he said calmly. "This will clean you inside." He gave her ass a sharp slap "thwack~ ~" making her jolt and gasp into the gag. The sting made her shake, but surprisingly, it also helped her relax just enough.
A thick stream of chocolate milk mixed with traces of waste gushed out into the bucket below.
The sound was loud and deeply humiliating "splssshhh~ ~ ~" as the liquid splattered into the plastic bucket.
Jenny's face burned with a mix of shame and unexpected pleasure. She tried to clench, to stop more from coming out, but every time she did, a sharp "slap~" would hit her ass, making her jolt and lose control. Her struggles were in vain.
She shut her eyes tightly, wishing she could cover her face. It was so embarrassing, yet her body trembled with sensations she couldn't fully deny.
Ash smiled, knowing Jenny must be feeling a confusing mix of weird sensations, yet undeniably good.
After all, he had done this before on his Mom and Daisy. Both had fully described to him how it felt: the strange fullness, the cold rush, the shame intertwined with reluctant pleasure.
The chocolate milk not only cleaned the inside but also covered any strange odor, allowing him to continue without hesitation.
He watched her trembling form, recognizing the same conflicted reactions he'd seen before, the tension in her shoulders, the subtle shiver she couldn't suppress. She might hate this, but her body was responding in ways she couldn't control.
He repeated the process three more times. Each round left her feeling emptier, cleaner, and more exposed than ever.
By the time he was done, his clone had already disappeared, his real body now stood behind her, taking over the cleaning process.
"It's clean now," he said softly, watching as the milk flowed out clear and odorless, looking just like fresh milk.
He gently spread her hole to look inside. It was now wet and glistening with a thin layer of milk. There was still some milk left inside, as Jenny now seemed too weak to push it all out on her own.
He said with a grin, "It looks really beautiful now." As he leaned in, he caught the sweet milky scent and couldn't resist. He began licking her anal hole with slow, deliberate strokes of his tongue.
Jenny shuddered, a muffled "mmph~ ~ ~" escaping her gag. She wanted to cry out, *No, don't lick it… it's dirty!*
But he didn't stop. To him, it was clean now. All he could taste was the faint sweet hint of chocolate milk mixed with the natural scent of her skin and a touch of salty sweat.
"Officer Jenny," he murmured against her sensitive skin, "your hole tastes really nice and sweet."
His tongue moved with slow skill, making soft "lick~ lick~ ~" sounds as it circled her tight hole before pressing just inside.
Jenny felt every wet, deliberate movement. It was humiliating, but it also stirred something deep inside her.
Each lick sent shivers through her. Her face burned with shame, but her body responded with unwanted pleasure. Her breaths grew heavier. Her hips trembled as heat built deep within her.
He worked her with patience until she tensed suddenly. A moan caught in her throat as an unexpected orgasm over her. Waves of pleasure rolled through her, something she never thought she'd feel from such an act.
When she finally stilled, breathless and overwhelmed, he pulled back.
He positioned the tip of his cock at her wet entrance, a sly smile touching his lips. "I hope you're ready…"
Read 5 chapters in advance on Patreon