Ash walked slowly toward Jessie, his eyes fixed on her still-dripping pussy.
Transparent fluid continued to leak from her swollen, red folds, running in slow, heavy drops down the inside of her trembling thighs and splattering softly onto the floor beneath her.
Jessie had only managed about twenty minutes of shaky, exhausted rest, her body still trembling from everything Ash had done to her earlier.
Her pale skin was flushed deep pink and glistening with sweat.
Her legs hung weak and shaking inside the tight ropes, barely able to hold her weight.
Her mind was foggy and tired, thoughts slow and scattered, like she was floating in a haze of unwanted pleasure that wouldn't let her think clearly.
Every breath came out shaky, her chest rising and falling fast, tears still drying on her flushed cheeks.
She looked completely worn out, broken, and helpless, hanging there like a used toy waiting for whatever came next.
When his warm hand gently pressed on her lower back, her eyes snapped open wide, fresh panic flooding her tired mind.
No… not again… I'm too tired… please…
Ash smiled gently and gripped the base of the thick red anal plug that had been stretching her all night.
He pulled it out slowly, deliberately, letting her feel every single inch drag against her sore, swollen anus.
The thick starting base stretched her open one last time, forcing the tender red hole to spread wide again with a soft, wet pop that echoed in the quiet room.
Jessie's whole body jerked at the sudden tug. A weak, muffled whimper leaked from her gag as the anal plug finally slipped free.
For a second her hole gaped open, dark from inside, the raw pink flesh twitching helplessly.
Then it fluttered weakly, trying to close, shrinking little by little, but too tired and too stretched from hours of the plug to shut instantly.
It stayed a small, puffy, red circle, pulsing faintly with every shaky breath she took.
Ash didn't let her wait longer.
His cock was still rock hard and from the last round with Officer Jenny.
He pressed the thick head against her slightly open, dry anus and pushed forward slowly.
Because the plug had kept her stretched for so long, the head slipped in easier than expected.
But the dryness still burned, her sore walls scraping against his skin.
Jessie's eyes rolled back.
A high "MMMMM!!!" tore from her gag as sharp pain shot through her.
Her exhausted mind screamed: It hurts… I'm too tired for this… stop… please I beg you…
Ash, who couldn't hear her thoughts, groaned softly, voice warm.
"Jessie… you're still so tight… Uhh "
He started slow, long, careful strokes, letting her feel every inch slide in and out of her dry, aching ass.
But it was too dry.
It felt rough and burning for both of them.
Ash could feel her tight walls dragging hard against his bare skin, almost no slickness, just heat and friction.
He stopped for a second, pulled all the way out, then he pushed back in with more force.
His hands gripped her soft, round butt cheeks tight, fingers sinking deep into the warm flesh, spreading her wider with every gentle push so he could watch himself disappear inside her.
Jessie cried out loud in pain, a muffled scream ripping from behind the gag.
Compared to the cold, hard anal plug that had stretched her all night (smooth, unyielding plastic that just sat there), Ash's cock felt completely, terrifyingly different.
It was hot, alive, pulsing with his heartbeat.
The thick veins dragged along her sore walls, the swollen head touching places the toy never reached.
It shook and throbbed inside her, growing even harder with every slow stroke, filling her in a way that was both more painful and strangely more real.
The pain was sharp at first, a burning, tearing stretch that made her whole body tense.
But as he kept going, slow and steady, never rushing, the dryness started to ease.
Her exhausted body finally gave in, betraying her one more time.
Even though there was no lube, the intense pressure and constant friction forced her inner walls to react on their own.
Tiny beads of natural moisture started seeping from the thin, delicate lining deep inside her ass (the same way a mouth waters when something fills it too long).
It wasn't much, just a warm, slippery film, but it was enough.
With every slow thrust the slickness spread, coating Ash's cock little by little, turning the tight burning drag into something smoother, deeper, shamefully bearable.
At first, each deep push felt like a pure, burning hit.
But slowly, so slowly she hated and loved it, the sharp pain started to change.
The burning eased into a heavy, full pressure… then into a warm, confusing glow that spread through her hips and belly.
Her tired body began to answer on its own.
She didn't want to feel it.
She fought it with everything she had left.
But, with every long thrust the ache turned into something else, something that made her breath hitch, made her sore walls flutter, made tiny, unwanted sparks of pleasure flickered inside her even while tears kept rolling down her cheeks.
The heat of his warm cock, the pulse of his veins, the way her stretched anus spread helplessly around him… it all mixed together until pain and unwanted pleasure blurred into one steady, overwhelming sensation she couldn't escape.
Feeling her anal muscles slowly relax and start welcoming him more and more, Ash's smile grew wider.
He sped up gradually, hips slapping softly at first against her warm, soft ass.
SLAP… SLAP… SLAP…
The rhythm quickly turned harder and faster, each wet smack echoing louder as he drove deeper, her body rocking forward with every thrust.
Then his hand came down hard.
SLAP!
The sharp sting hit her ass like fire.
Jessie's whole tired body jumped.
A loud, muffled "MMMMM!!" burst from her gag.
Her ass squeezed him super tight all of a sudden.
At the same time her pussy gave a big twitch and squirted a little, warm juice running down her legs.
Ash groaned happily, seeing both holes react to the slap.
***
Read chapter 27.2 in advance and in a few hours, chapter 28 will drop to on Patreon[C0DX], Join the chat.