02

Teasing the Shy Guard

The next morning, Stiles walked the prison corridors like she was strolling through a luxury mall instead of a women’s correctional facility. Even in the baggy gray prison t-shirt and loose pants, her body refused to be hidden. Her massive tits stretched the thin fabric, her fat ass swayed hypnotically with every step, and her wide hips rolled like she was still wearing that tiny white dress from yesterday.

The other female inmates glared at her with pure disgust.

“Fucking whore,” one muttered as Stiles passed.

“Look at her, acting like she’s on vacation.”

“Bet she’s already wet thinking about sucking off every guard here.”

Stiles just smiled sweetly and blew them a kiss. “Jealous, babies? Don’t worry, there’s enough cock in this place for all of us… if you knew how to spread your legs properly~”

The male guards couldn’t keep their eyes off her. They eye-fucked her openly—staring at her bouncing tits, her jiggling ass, the way her nipples poked through the shirt. Whispers followed her everywhere.

But Stiles only cared about one guard.

Derek Hale.

Every time she spotted him, she made sure to tease him the hardest. He was different—tall, muscled, handsome, and so easily flushed. While the others smirked or catcalled, Derek looked away shyly, ears turning red, trying (and failing) to stay professional.

Stiles loved that.

During yard time, she “accidentally” dropped the small book she was carrying right in front of him. She bent over slowly, sluttily, pushing her fat ass out toward him. The loose pants stretched tight over her round cheeks, outlining every curve.

She shook her ass just a little as she picked it up, glancing back at him with a filthy smile.

Derek’s eyes widened. He swallowed hard, his cock twitching in his uniform pants.

Stiles straightened up and walked too close, letting her heavy tits graze against his arm as she passed. She leaned in and whispered hotly against his ear,

“You look like you’ve never had a bad girl before, Officer Derek… Never had a real slut ride your cock until you forget your own name~”

Derek’s breath hitched. “Stiles… please… not here.”

She giggled and walked away, ass swaying extra for him.

The warden watched everything with narrowed eyes. She hated Stiles already. “That little cum-rag is trouble,” she muttered to another guard. “Keep an eye on her. Especially around the new guy.”

Stiles didn’t care. Prison was boring after just one day. No shopping, no flirting with rich men, no thick cocks stretching her greedy holes. She missed being fucked. There were plenty of guards here who would probably bend her over in a second, but getting caught would only add more time to her sentence.

But Derek… he seemed different. Shy. Kind. The type who kept to himself. If she played her cards right, she could get his cock and maybe sweet-talk her way out of this place.

That night, during cell check, her plan went into full slut mode.

Derek walked the block, flashlight in hand, checking each cell. When he reached Stiles’s, she was already waiting.

She pressed herself right up against the bars, squishing her massive tits between the cold metal. The fabric of her shirt stretched obscenely, her hard nipples clearly visible.

“Hey, big boy~” she purred, voice low and dripping with lust. “Come closer. I’ve been thinking about you all day.”

Derek stopped, cheeks already pink. “Stiles… I’m just doing my rounds. Step back.”

She didn’t. Instead, she rubbed her tits slowly against the bars, making them jiggle.

“If you open this door, Officer Derek… I’ll drop to my knees and suck your cock so good. I’ll take every inch down my throat until my pink lips are wrapped around your balls. I’ll gag and drool all over you like a filthy little whore while you fuck my face. Then I’ll bend over and spread my fat ass for you. You can pound my tight pink pussy raw. I’ll moan so loud… ‘Fuck me harder, Derek! Stretch my slutty cunt!’ I’ll let you fill me up with your hot cum until it’s leaking down my thighs. Wouldn’t you like that? A pretty slut like me begging for your cock every night?”

Derek’s breathing grew heavy. His cock was rock hard, straining painfully against his pants. “Fuck… Stiles, you can’t say things like that…”

But he didn’t walk away.

Stiles smirked and stepped back a little. “Watch me, shy boy.”

She started a slow, slutty strip tease right there in her cell. She peeled the gray t-shirt up teasingly, revealing her huge, perfect tits. They bounced free, heavy and full, pink nipples stiff. She cupped them, squeezed them together, and shook them for him, making them jiggle obscenely.

“Mmm… you like my big tits, Derek? They’re so soft… Imagine your cock sliding between them while I tit-fuck you~”

She turned around, pushed her pants down slowly, and bent over, shaking her fat ass at him. Her cheeks clapped lightly as she twerked, giving him a perfect view of her dripping pink pussy from behind.

“Look at this fat ass… It’s all yours if you want it. I’ll ride you reverse cowgirl so you can watch it bounce on your thick cock.”

She turned back to face him, sat on the edge of her bed, spread her legs wide, and opened her puffy pink pussy with two fingers. It was already soaked, shiny with arousal. She started rubbing her swollen clit in slow circles, then pushed two fingers deep inside herself.

“Ahhh~ Fuck… Look how wet I am for you, Derek. My pussy is dripping just thinking about your cock.”

She moaned sluttily, fingering herself harder while her other hand squeezed and pinched her tits.

“Touch yourself for me, baby… Please? I want to see that big, hard cock. Stroke it while you watch me play with my slutty holes. Be a good boy and jerk off for your dirty little prisoner~”

Derek was breathing hard, face flushed dark red. His hand moved almost on its own, slipping inside his pants. He pulled out his thick, veiny cock—long and heavy, already leaking precum.

“Shit… Stiles…” he groaned, wrapping his hand around himself and starting to stroke slowly.

Stiles’s eyes lit up with pure lust. “Mmm yes~ That’s it, Derek. Look how big and hard you are for me. Stroke it faster. Imagine it’s my tight pussy wrapped around you instead of your hand. My fat cunt sucking you in, creaming all over your cock.”

She fingered herself deeper, curling her fingers to hit her G-spot, moaning loudly.

“Fuck… I’d bounce on that cock so good. My big tits slapping your face while I ride you. I’d milk every drop of cum from your balls. Would you cum inside me, Derek? Fill your little slut’s womb? Or would you pull out and paint my pretty face and tits with your hot load?”

Derek’s hand moved faster, slick sounds filling the quiet hallway. His voice was shaky and hoarse. “Stiles… you’re so fucking dirty… Your pussy looks so tight… I… I shouldn’t be doing this…”

“But you love it, don’t you?” Stiles moaned, pumping her fingers in and out rapidly, her tits bouncing with every thrust. “You love watching a filthy whore like me finger-fuck her dripping cunt for you. Tell me, baby… Tell me how much you want to fuck me. Say it.”

Derek groaned, stroking harder. “I… I want to fuck you so bad… Want to bury my cock in that pretty pink pussy… Make you scream my name…”

“Yes~ Just like that!” Stiles cried out, rubbing her clit furiously while squeezing one tit hard. “I’m such a cock-hungry slut… I need your cum, Derek. I need it so fucking bad. Cum for me, baby. Shoot your load while you watch me cum on my fingers. Pretend you’re filling me up~”

Their dirty talk grew filthier, voices mixing in the dark corridor.

Stiles: “My pussy is clenching so hard… imagining your thick cock stretching me open… I’m gonna cum so fucking hard for you!”

Derek: “Fuck… Stiles… your tits… your wet pussy… I’m so close…”

Stiles arched her back, moaning like a pornstar as her orgasm hit. “Ahhh—! I’m cumming! Watch my slutty cunt squirt for you, Derek—!”

Her pussy gushed, juices dripping onto the floor as she shook and cried out in pleasure, fingers buried deep.

Derek couldn’t hold back anymore. With a strangled groan, he stroked himself furiously and came hard. Thick ropes of cum shot into his hand and inside his pants, his hips jerking as he tried to stay quiet. “Shit… Stiles… fuck…”

They both panted heavily, coming down from their intense orgasms.

Derek quickly tucked himself away, face burning with embarrassment. He looked completely flustered, ashamed, and still turned on. Without a word, he turned and walked away fast, boots echoing down the hall.

Stiles leaned back on her bed, licking her fingers clean with a satisfied smirk.

She whispered to herself, eyes sparkling with mischief,

“Mmm… You’re my ticket out of here, shy boy. I’m going to drain that cock and that kind heart until you’re ready to do anything for me~”

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