Category: Anal Stories

Caught Shoplifting

by Goldeniangel©

Jimmy cursed as he saw a girl slipping something into her purse from the shelves on the security camera. He'd been working as a security guard for months now, but he still hated it when he caught a shop-lifter, it meant having to leave the comfy confines of the security office. Not to mention all the paper-work. Then he froze as the girl looked around, checking to make sure no one was watching her. That was no girl, that was the 23 year old bitch that had ended the friendship between him and his best friend!

Possessive, controlling, manipulative; Becky was everything he'd ever hated in one of his friend's girlfriend's. And now Dane never hung out with anyone but her, Jimmy hadn't seen him in months.

He almost hurt himself rushing out to apprehend her, the best revenge he could have ever possibly gotten! What was even better was that Becky totally recognized him, her eyes blazing with contempt and dislike as he escorted her back to the security office.

Sitting her down in the chair across the desk, Jimmy locked the door and sat across from her, grinning madly at his coup.

"Oh stop smiling like that," she sneered, "Whoop-de-doo, you caught me shop-lifting. Good for you."

"It is good for me," he said calmly, "I don't believe you've thought out all the repercussions of this."

Becky rolled her eyes. God he'd always hated how she thought she was so much better and smarter than anyone else, "So have the police come and arrest me. I'll get out of it, I always do." She smirked, "They like good head, just like anybody else."

Somehow it didn't surprise him that Becky used sex to get out of sticky situations, and it didn't surprise him that she didn't care it was cheating on Dane. She'd always been selfish... but he had an ace up his sleeve.

Pulling out the tape recorder that he'd left running in his pocket, he rewound it and played back the her last words as her face paled. That was good enough for any judge, enough to get her police friends in trouble as well and then she'd be up the creek in no time. She'd probably even get jail time... and no guard at the prison would be happy with someone who'd gotten fellow officers in trouble.

"What do you want," she said, her voice demanding but quivering as she tried to hold onto the high ground.

Jimmy was about to take her down a notch or two, "Well Becky, you see, you've always been such a pain in my ass, that I think I'd like to return the favor."

His dick twitched inside his pants as her expression went from confused to shocked to scared, her face paling.

"No," she said, her tone definitive. Jimmy shrugged and reached for the phone, smiling as she screeched "WAIT!"

Looking up at her, he saw that she was practically sweating, breathing hard. "Yes?" he asked, waiting for her response. Becky swallowed a few times, trying to gather her nerve.

He was just about to add more pressure by reaching for the phone again when she said, "Ok."

"Good," he smiled, standing. His dick was already a tent in his pants, a tent that she couldn't keep her eyes off of, "Stand up and strip."

Although she tried to look contemptuous, she wasn't good enough to pull it off as she had to strip naked in front of him. She was pretty hot, a little chubby but her breasts weren't too bad and her ass was delicious. Big and cushiony, just the way he liked it. He made her bend over the desk, and as she was facing away from him he grabbed her wrists and quickly hand-cuffed her wrists behind her back.

Becky screeched, "What are you doing!!!" and then screeched again as he slapped her wide ass, watching the flesh jiggle.

"I'm just making sure you know who's in control," he told her, "Cuz it sure as hell ain't you."

She lay quiet after he'd spanked her, and he just enjoyed looking over her curvy backside as he pulled his pants down. Placing the wide head of his dick against her tiny rosebud, he grinned as he compared the size difference... she was obviously an anal virgin and this was going to hurt a lot. He decided to scare her even more and began to try and push into her tight virgin ass without any lube at all.

Becky screamed as her tender asshole burned, "STOP! STOP, PLEASE STOP!"

Jimmy stopped but didn't pull out, only about half his head was in her anyway. Her ass already looked tightly stretched around that and he was rather enjoying the way her muscles were squeezing down on the sensitive head of his dick, so tight and hot.

"Yes?" he inquired.

"Please," she begged, damn he liked her begging, "Put some lube on, let me suck it, SOMETHING...."

"You think I'm going to trust you with my dick in your mouth?" he laughed, "I don't think so. But I'll lube it up, I don't want you to end up bleeding I guess. Not really a turn on for me."

And with that he pulled the little bit of his dick that he'd worked in away from her asshole, making her sigh with relief and relax, making it very easy for him to slam into her pussy. She screamed as he invaded her womanhood, despair and humiliation easy to hear in her voice as she was fucked by a guy that she'd fucked over. Jimmy was shocked at how wet she was, not to mention how tight. Either Dane wasn't fucking this bitch enough, or he had a pencil dick.

"You whore, you're soaking wet down here," he laughed at her as she hung her head in obvious humiliation, his dick pounding in and out of her tight pussy, loosening it up. He enjoyed a leisurely fuck, pulling on her cuffed wrists to slam her pussy back against him. It was so tight and wet, some of the best pussy he'd had in awhile honestly, and of course made even sweeter by revenge. Not that he forgot that pussy wasn't what he was there for... but he had an even better idea to humiliate her with.

Skillfully he fucked her, reaching underneath her to rub her clit with his fingers. Slowly she started pushing back against him, almost minutely at first and then with growing intensity as she was unable to deny the sexual pleasure that he was creating. When she was bucking against him, her pussy trembling as he rode her closer and closer to orgasm, Jimmy pulled out, leaving her gasping and unfinished.

Becky protested, first as he pulled out, and then as he pressed the slick head of his dick against her ass. Just for now, he stopped rubbing her clit, wanting nothing to distract her from the slow invasion and defloration of her virgin ass. She cried out as the head of his dick popped in, the inside of her ass filled with heat and incredibly tight. Grinning, he gripped her hips with his hands and shoved deeper, making her eyes pop as the burning log of pain slid deeper into her rectum.

"Oh please stop, please stop it hurts," she was begging as he invaded her ass. Of course he ignored her, the begging just making him harder as he deflowered her last hole. Becky groaned and shuddered as he buried himself completely in her ass, feeling like she was constipated as her muscles rippled around him, trying to shove him back out the way he'd came. Her asshole was tightly stretched around the base of his dick, unable to close down.

When he began to pull out she felt wave after cramping wave of pain, coursing through her asshole, making her cry out. Finally taking pity on her, Jimmy started to rub her clit again as he began to push in and out of her tight ass, holding himself inside her every time he buried his dick completely, feeling her ass squeeze him tightly. To Becky's surprise, his fingers on her clit helped with the pain a lot, pleasure battling discomfort in her lower region, helping her to relax and therefore accept his dick more readily.

Feeling her body giving up the fight against his dick, Jimmy began to sodomize her more forcefully, really pounding her ass. Becky moaned and moved her hips as his dick slid slickly in and out of her, the pain mixing with the pleasure that was emanating from her clit and making her body confused. She began moving back against him, her ass opening up and accepting the hard thrusts, even the steady pounding into her asshole was beginning to feel good as the pleasure in her pussy built. Trying to fight against it was useless, even though her mind was screaming out that she shouldn't like it, her body was moving towards climax without her consent.

Her orgasm was the ultimate humiliation. Blackmailed into being sodomized, she was now cumming from in, a dick buried in her ass while she creamed herself. Jimmy grunted as her ass began to clench down hard on his dick in spasms, her orgasm making the hole even tighter, and he fucked harder, forcing her ass to open for him as she came.

Since she was cumming he took his hand away from her clit, ignoring her humiliating pleasure now in order to find his own. Gripping her wide hips, he slammed into her ass, making her cry out as he stabbed her bowels deeply. With a hard thrust that took her breath away, Jimmy arched his back and cried out with completion, his dick pulsing against the tightness of her ass as he unloaded into her deflowered hole.

Becky was very quite as he pulled out of her ass and released her from the cuffs. He already had his pants back up and zipped as she pushed herself away from the desk, her asshole looking swollen and red. Jimmy sat at his desk and watched her get dressed and quietly leave. She didn't look nearly as confident and uppity anymore.

Smiling to himself, he went back to watching the screens, satisfied with his day's work.

Written by: Goldeniangel

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Story Tags: forced, reluctance, rough anal, first time anal, caught, punishment, ravishment

Category: Anal Stories