Jennifer's Crime and Punishment

This story is fiction. The author does not condone these actions in real life. The characters are of age. Story features forced, reluctant, dominance, spanking, sucking, fucking, and anal.

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Another nice morning for another low down shopping area. A few eateries, a bail bond, and furniture store were open as normal. However, a small time clothing store is going to have to a lovely encounter with Jennifer.

Back at Jennifer's apartment.

"Look if you don't have any underwear anymore, then..." Jennifer's roommate continues, "Well just go steal some of that shit. Ok so I go to this one little store and sometimes I take panties, bra, or a tanktop. They never fucking notice. The owner is this little old man and some slow fat security guard. You'll be fine." Alice looked at Jennifer completely confident like stealing is not going to bother Jennifer, whatsoever.

"Well, umm, I guess if..." Jennifer thinking the idea is dumb at first starts to reconsider that it might be worth a shot. She has other expenses to look after. Only wanted a couple pairs at least. "I guess if I thought it through I could grab a few pairs of panties."

"Yea. And how you losing so much underwear, girl?!" Alice yells a curious question and sips her morning coffee, from the café shop that Jennifer recently refuses to go visit.

"Oh umm,..." Jennifer pauses. The 21 year old wiggles in her seat, quickly remembering her humiliating moments of losing underwear, like in the alleyway, at the cafe, and recently with the old men. "Umm, gee, I don't know. It's like... that time to get some. You know?" Jennifer stops there.

"...Yea it get that sometimes. Like all my shirts be getting holes at the same time. Like what the fuck is going on. You know?" Alice continues to rant on. Before leaving for her day, she mentions to Jennifer how she did it; how she stole from the store.

"Ok the owner is an old Chinese dude. He's real slow." Alice adds on her lipstick. Then continues. "So I just grab some. Some underwear, just all cool. And walk out of sight. And bam" SMACK. She smacks her lips. "I put all the underwear on....Oh because I'm wearing a skirt. That's why. And then I walk on out. Buying nothing at all girl." Alice exits. Leaving Jennifer wondering whether to try this or not; would it be worth it? Surely, she could grab a few pairs and get out. She could use some more underwear after so many strange men keep ruining her panties.

"Alright I think I can pull it off." Jennifer thinks to herself. She selects a light blue summer dress to wear, so she slips those hot goods over her hot buns. Jennifer finishes getting ready with a tiny white thong and white sneakers on her nubile body. Then heads over to the store.

Almost 69 minutes later,

"You had no chance of pulling this off" A security guard says. "You were caught stealing clothes. Stealing from Mr. Lee. Tsk Tsk. I knew the camera caught you." The cameras didn't catch a thing and Sam the security guard knew that. He's hoping to have some fun with this beautiful girl he caught stealing panties.

"Umm." Jennifer is bending over on an old wooden table. She's in the inventory room. She's stares at a box reading this side fragile. Her light summer dress lifting and hinting at her fragile beautiful round ass. "Hmmm, sir?" She looks behind her.

"Look I saw you take those panties" The security guard says through a smile. "And like I told you earlier. umm." The 43-year old man trying to gather up the confidence to keep true to his plan. "Either I call the police for theft or I punish you. Punish you right now. Here." He steps closer to her perky booty.

"No don't call the police! Ok umm... Uhh, well, I guess we can..." Jennifer is struggling on what to say. She forgets even more when she feels her skirt flip up and entirely expose her butt. Oh no, what does this security guard have planned?

"See, look at that!" SMACK He wastes no time in enjoying Jennifer's fine young ass. "Look at all these stolen thongs! Naughty girl!" SMACK. Sam gives a mighty slap and then yanks all her panties down and off her body. He even takes the one pair the young woman came in with. Now Jennifer's bare bottom showing to the security guard's happy face.

Jennifer begrudgingly bends over the table and feels her little blue summer dress exposing some of her supple butt cheeks. She couldn't believe she was about to let herself be spanked by Sam the security officer. But getting sent to jail will be way worse she thought. Damnit for getting caught Jennifer! Surely, he will just spank her a little bit and let her go when she learns her lesson. Maybe he will take it lite on Jennifer. So wrong.

What Jennifer didn't anticipate is that the security guard loves a good round ass and he is very excited to give a spanking to her vulnerable juicy bottom. And for the next 10 minutes of spanking, her ass bounces over and over until it's hot pink. Then Sam repositions himself, readies his other hand and spanks her more till it's red. Embarrassing ass slut red. Jennifer remains in position like a good girl but continues to sway and wiggle her butt like a naughty girl. Jenifer stares at the dusty boxes and old junk inventory still in storage. There isn't much in this room, other than the table she's using. A simple wooden chair and lots of boxes. It definitely wasn't clean, Jennifer realized when she knocked off table covered of trash before bending over.

then Jennifer gasps once she realizes her a little blue dress is lifted up exposing her ample round bottom. Her butt sways back-and-forth as a security guard gets in position. Jennifer looked over her shoulder nervous about what's to come. Sam can't believe his luck to have such a fine young woman punish.

Jennifer's ass is constantly walloped by the smiling security guard. He is enjoying the sounds from this distress damsel. He's also conjuring a plan to get more out of this beautiful babe. He continues to spank her behind hard. Hoping to get her to a breaking point. Her buttocks heavy jiggle to the full palm slaps. Over and over on Jennifer's round ass, making sure that her butt turns red.

Jennifer starts crying and losing her breath. This spanking has been going on for a long time in her painful mind. Her butt is fiery and stings so much to every spank. The security officer is relentless on abusing her behind. Keeping her ass cheeks in a constant state of trembling and quivering is devastating to Jennifer. She hopes he would hit her softer, or at least slow down.

"Oh ow! Ah okay. I'm sorry. Ow. Are we good now? Oh my ass hurts. I learned my lesson sir. Sorry for stealing. I'm sorry." Jennifer's nervous hand starts rubbing her red butt.

The guard lets a big chuckle. "I ain't done with you. I'm still giving it to you. Just resting my hand." He squeezes hard her right ass cheek.

"In fact get you're ass up on the table. On your hands and knees. Come on. Let's go." He pats the table, motioning for the humiliated brunette to get on top. Jennifer's eyes widen in anticipation of what he wants. She looks nervous but slowly gets her naïve body in doggy position on the tabletop. Her elevated ass points right at the guards face. Sam freezes at the view, forgetting what he planned to do next. Jennifer's flared hips and round mound ass is a mighty distraction.

"Umm... sir. What. What happens now?" She unknowingly asks in her sweet submissive voice. Just hearing her say that in her damsel voice makes his cock push against his pants.

"Huh?... Oh right. Need to keep punishing your thieving ass" SPANK. Then he gives a mighty upwards slap to her bum. Right in middle so it sent a shock wave to Jennifer's pussy lips as well. Jennifer let's out a comical gasp and wiggles her butt.

"Now I wanna hear you say. Thank you sir. Spank my thieving ass." He squeezes her left cheek. "Get this big booty up in the air And keep doing those sweet moans." Jennifer didn't know what he meant. Those moans and squeals came natural from her. Then she lowers her shoulders to the tabletop and makes her ass the finest centerpiece Sam has ever seen. This new position is so humiliating for Jennifer, lewdly showing her whole bottom and pussy to the security guard.

SPANK..."Thank you sir! Spank my ass! SPANK... "Ow! Thank you sir! Spank my thieving ass!" SPANK "Ooh thank you sir! Spank my ass." The security guard gets very aggressive spanking her bottom. He hardly allows any rest for the 21 year old woman and enjoys seeing the babe's bouncing bum.

Jennifer is losing it. She feels so much pain that her bottom. It feels like it's on fire and thinking straight is very challenging. Thinking of a way to end the spanking, Jennifer wonders if she can convince him that she learned her lesson. Because she can't take anymore spanks. Jennifer feels her ass is thrashed. Sam has been spanking her cheeks so hard and so thorough. Past some blubbering tears, Jennifer tries to speak to her spanker.

"Oh ow! sir! Wait! Please! SPANK. Ah, I'm so sorry! Wait. SPANK. Ow! Oh fuck, no more spanks please! Lets do something else. SPANK. Ah I'm sorry, I'll do something else, let's do something else sir. I can't. I can't take it anymore! Ohh..my ass! It stings so much! I'm sorry. Oh fuck." Jennifer briefly regains herself and finally stares at the guard for an appeal, thinking of what else she could do to end this punishment.

Moments later.

"Oh shit! Ok, so um, your dick is long... I can't suck all that, sir." Jennifer looks up, past the raging cock and into the eyes of the horny security guard Sam.

He made a deal with Jennifer. He would agree to let her go if she pleased him. Since she couldn't handle the full spanking and had left him with an erection, he figured justice and punishment would take care of itself at once. She didn't want the police to get her and begrudgingly agreed to his conditions. Sam convinced the dumb brunette babe that he wouldn't file a police report, only if Jennifer took care of his erection. Jennifer reluctantly agreed so as long her ass stopped getting spanked. Her butt remains deep red and red it will be for Jennifer's whole next ordeal.

"Oh yes you can sexy." Sam smacks his lips. "That dick will cum, once you take care of it. But ya gots to do it real good gurl."

Jennifer stares at the long cock stiffening into attention position. Then she sighs. She doesn't want anymore spankings so sucking him off shouldn't be too bad. But if she applies her skills maybe she could end this quick. Jennifer didn't want this to go any further nor is thrilled to blow this creepy security guard. After all her humiliating degrading encounters like in the alley, cafe shop, and recently at old folks residence, Jennifer desperately wants her pussy free from any abuse. And her asshole. Of course both, she concluded.

"Well just sit down and let me get this over with." Jennifer motions for him to sit and he does. Then Jennifer licks her lips and starts running her mouth up and down his shaft. Her tongue licking all that she could before finally putting the head of the cock fully in her wet mouth. She closes her lips tight on the head and sucks a little. Then bobs up and down, showing the guard that Jennifer's mouth can take half his cock already.

Jennifer thought she did a great start. She wanted to remain in control and maintain the blowjob her way. Well that lasted 30 seconds. After tasting his cock, Jennifer tries to spit and clean it off a little better. It's a very sweaty cock, Jennifer realizes when the musty smell hits her nose. But before she could get her mouth off his cock. Sam's hand catches the back of Jennifer's head and keeps her from dislodging his member. Holding still on her hands and knees, confused Jennifer stares at the security guard with his cockhead in her sucking mouth.

"This feels great already. But..." He pauses. Jennifer did not like that pause. "But I still need to remember that you're a fucking thief." Jennifer suddenly gets a surge of penis in her mouth. Her mouth trying to accommodate the best she could as Sam begins to thrusts in her mouth.

Sam doesn't stop. He starts to face fuck Jennifer with an aggressive touch. She squirms to the sudden face fucking but can't get out of his grip. The dame's blue eyes widen and her hands move onto the security guards knees. This guard's dick is getting deeper and deeper in her mouth and she still hasn't reached the base! She shudders at the thought of getting this all in her mouth. Jennifer hopes he would be contempt with her mouth covering about 6 inches of his 9 inch dick. She's hoping her moans, groans, and sucking cheeks can help his experience. It damn well does. Or did. Because he is done with the slow pace of gliding her back and forth.

"Ok, hold on." Sam pauses Jennifer with several inches of cock filling her mouth. "Do you wanna go to jail? Hm?!" Through a gurgled tone humiliated woman sputters out a 'No'.

"And you need me to cum to get free right?" He pats the top of her head. He keeps his hand there. Again through a mouth filled mess, Jennifer tries to say, "Yessir".

"Well then let's speed this up. Ok slut thief, say 'Fuck my Face, Fuck my Mouth' and we can get you out of here."

Jennifer's looks shocked at what she heard. She's feeling so degraded trying to speak with so much dick in her mouth. Now, this is getting out of hand she thought. He should be close to finishing by now, she wonders. Jennifer looks up with vulnerable eyes and attempts to tell the guard to "mphuckMaphace." She repeats it again. "mmphuck...Maphace."

"With pleasure you slutty thief." Then he places his second hand on her head and starts pumping his hips into the face fuck orifice. The security guard double palms Jennifer's head and fucks past her lips with authority. Loud gagging sounds and spittle leave the humiliated young woman's mouth. Jennifer has never felt so face fucked before.

For the next few minutes, Jennifer gives one of the most hardcore blowjobs she's done. The security guard is quickly rocking her head back and forth to cover all his raging dick. Her mouth is constantly filled and her deepthroating is on display. Whenever Jennifer tried to get her hands on Sam's shaft to stroke it, the guard would swipe it away. Only her sweet mouth is going to get his mean 9 inch dick. Jennifer uncontrollably drools and gags over and over. Her moans and groans are constantly motivating Sam to keep face fucking the distressed brunette. Sam's loving embarrassing her, so he kept telling her to talk during the oral sex.

Eventually Jennifer couldn't keep up, her mouth gets so tired and her throat wants a break. Yet, the guard is still banging her dazed faced right into his crotch with the same intensity as the beginning. All nine inches have been penetrating her gullet like this dude never had sex but he still hasn't cum! She needed a new strategy, something to help his dick, she thought.

In moment of desperation, Jennifer finds a chance to pop off the cock, swallow and then speak. "Ungh. Wait! I can't...do this anymore. Aren't you close yet? I've been sucking for so long now." Jennifer looks down and absentmindedly says. "Can...can we do something else?"

The security guard smiles at the suggestion. "Ok, I get it. This situation could use a little help. Your mouth is great. But that pussy would get good results too."

"OH! No, not that! No. I don't want sex with you! Not my pussy please."

"Ok ok. Well then sweet cheeks, that leaves us with your juicy round bottom to bang." Sam grinning at the thought. "Or I'll call the cops if you leave me unresolved. So what's it going to be...thief." He strokes his cock while grinning at her.

Jennifer gasps looking every bit shocked to his suggestion. It would be humiliating to give her ass to this stranger. But she didn't want to go to jail for stealing panties either. Sucking his dick has exhausted her mouth and she really wants to get home now. Jennifer wonders if anal sex is more ideal than jail. And since she doesn't want to get in long term trouble, Jennifer sighs, realizing her brown hole fate.

"But, butt sex is really awful. I'm not that type of girl...." She remembers groaning to her humiliating anal experience at the café drive thru and then sighs. "Oh, uh please. Go easy on me." Jennifer looks completely shy and embarrassed to agree to this. "Go easy on my ass sir."

Jennifer starts bending over the table. She grabs the ends of the table again. The young damsel presents her round butt yet this time its for something more degrading. Jennifer gulps and looks nervous. She is dreading this whole thing but slowly sticks out her behind while still wearing her dress. Jennifer feels her D-tits squish against the table and the goosebumps on her exposed ass.

"Oh shit. I'm getting ass fucked...again! Fucking hell." The brunette yells in her mind as she looks over her shoulder. Watching the security guard approach her butt cheeks. Jennifer knew she was wrong to steal, that she did a dumb thing and she badly wants to get out of trouble. The young babe hoping for this to resolve earlier and definitely didn't want to feel his cock in her rectum. Yet here she is, staring at a nasty security guard with a dick ready to ram her asshole. Sam orders her to ask for it. To further add more humiliation.

"Oh...Fuck my butt. Fuck my asshole, sir. Um, please don't file a report and you can fuck my ass." Jennifer sways her ample bottom. Then suddenly stops. "B-but don't cum in my ass. You can cum on top of me. Um, ok?" Jennifer is hoping to avoid further degrading acts with this submissive behavior.

"Yes, sure babe, whatever." Sam walks up to his dreamy peach prize. He flips the skirt up and Jennifer gasps like a schoolgirl. This delicious behind of a young tease is now on display to this horny security guard. Plus, to make everything better, this babe's ass is still very red. The hard hand spanking Jennifer took is clearly lingering around with her rogue ass shaking in front of him. He knows his cock is well wet, thanks to ten minutes of face fucking Jennifer. He grabs her hips and aims his long pecker at her winking backdoor.

Sam had no trouble getting his dick in her butt. He penetrated her asshole with minimal effort and maximum enjoyment. "Unngh oh fuck!!!" Jennifer yells and squirms to the cockhead lodging its way in her behind.

Sam gives it to her good. He starts to pump into Jennifer's big round ass immediately. Her ass cheeks are a delicious sight so he didn't want to waste any time. Technically, he is still on the clock for work but the owner is so old and slow to everything at this point he never notices anything. Sam softly chuckles, thinking how he is getting paid to buttfuck this beautiful dumb babe. Banging her asshole, Sam became a wild animal. At 45 years old he never thought of having a piece of ass as fine as this again. So he decides to not waste his opportunity and pistons his cock into Jennifer's bubble butt. She yelps, moans and groans to everything happening to her. Jennifer can't stand how long the rigid dick feels (but she bends over for it). Her anal chute is giving way to so much cock sliding back and forth. The fucked thief could feel the whole length moving past her sphincter. Jennifer feels so degraded with this nasty security guard stuffing her ass.

"OH mmphuck! Oh my ass! Oh e-easy! OW! Oh ah, fuck! Please sir. Ungh. Easy. Oh fuck. Easy on my ass! Ooh ow. It still hurts. Ow, it still stings! Ah fuck! Oh sir..." Jennifer tries to plea with her captor. With Sam slamming against the brunette's bouncing ass cheeks, she quickly realizes that her behind is still burning from the spankings earlier. Now she's getting reminded of her sore red ass with every thrust that Sam's body makes contact against her. Jennifer's ass is stinging a whole lot inside and out, much to her dismay.