She Should Be More Careful

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Jack didn't want to do it this way...
3.2k words
4.2
36.2k
26

Part 1 of the 2 part series

Updated 10/21/2022
Created 06/12/2013
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Jack looked in his back seat to see the girl of his dreams passed out. She almost looked like she was taking a nap on a long car ride, if you didn't look too close to see her wrist's where bound. Jack felt a little bad he had to do things this way, but honestly thought it the best way.

The girl in the backs name was Elizabeth, But most call her Liz. She had long auburn hair with bangs that framed her adorable round face beautifully. Her lily white skin was flecked with cute freckles (adding to her adorableness.) Her face looked so sweet, with her freckles and permanently rosy cheeks. Liz was also quite short, 5 1' to be exact, with B cup tits, not perfect but a good mouthful. She had a lovely hourglass, perhaps more on the pear side. She also possessed an amazing ass that curved beautifully from the small of her back and to the globes of her perfect lily white cheeks. Not big (not small either) but shaped well. A little on the chubby side at 125 to 130, but he could still easily throw her around. The thought made him get hard.

You see Jack is a powerful man. He runs a business he took over after his father passed. His business did not have one specific thing it did, but many shady dealing and projects on the side clumped into one. His father was apparently the ring leader and kept all these dealing together to keep up his fortune and get into inner circles. So when Jack took over he was put in the place of his father in these circles.

Jack, though he loved the business felt something was missing (oh so cliché, but true!) After finishing up a side project his business was part of ,and gaining many new resources and a large profit, Jack still felt odd. Getting out of his routine he stopped at a local club for a drink. Thinking of maybe picking up a girl he scanned the room.

Jack had no problem getting women. At 6'2 he was quite handsome, toned but not overly muscular, maybe a tad on the lanky side. He had olive skin tone and thick wavy black hair that went well with his masculine face and defined jaw. What caught most people's attention where his piercing light blue eyes, almost gray. They gave a sharp contrast to his tanned skin and dark hair.

When Jack scanned the room he found his eyes gravitate towards a short girl in a blue dress. He overheard her conversation with the small group of other girls. She was joking around and others where laughing. It wasn't that hard to hear her, she was talking quite loud. He watched her in his peripheral vision Several times he had to stop himself from laughing at what she said to remain undetected as over hearing.

He looked at her again and took in her features more this time. A sweet face, pretty, long auburn hair, the way her curves looked in the fitted blue and white polka dot dress. She seemed to down to earth and confident. Not really knowing what to say he walked up to her and tapped her shoulder. Her reaction was not expected.

She gave a quick yelp and flinched away, she nearly fell off of the high stool she sat on. Her friends where good naturally laughing at her scared reaction. The way her face turned red ,and she looked all flustered, was the most attractive thing he ever saw.

After a moment she stuttered out she was sorry for her reaction ,and that she was naturally jumpy. She wouldn't look at me until I said I didn't mean to scare her, but when she did my heart skipped a beat as the most beautiful big hazel-green eyes met his.

"Um, what did you tap my shoulder for?" Liz said to him, still embarrassed and coping through an anxiety attack.

Jack hesitated, almost saying 'you' and instead said something equally cliché, but charming.

They had a nice conversation, Jack loved to hear her sweet voice. But could tell she was uncomfortable, which made him even more attracted to her. After a bit her friend came to her rescue and gave an excuse to why they had to leave. Liz hurriedly said her Good-bye's, saying she comes here often. He had to see her again and asked for her number. Wanting to get away she obliged.

Liz has always disliked being touched and hated that it kept her from having "intimate" relationships. She berated herself for her awkwardness around the handsome guy at the club. Many people found it odd she was like that, she was a very warm and kind person,and she was never abused. Liz knew she should go to therapy, but she had been in therapy for years when she was younger, her parents forced her because of her social awkwardness and disobedience. The therapy never helped change her ,she made her own decision and she didn't feel like therapy could help her. Liz punched her pillow in frustration thinking back to those pointless therapy sessions and how miserable she was as an early teen.

Jack had tried to get her to open up, but found it nearly impossible. He went on a few unofficial dates with her and got into her social circles, but she just wasn't comfortable. A week after Jack met Liz he started watching her. She really wasn't that careful, often kept blinds up and also went off on her own a lot. Jacks favorite part of watching her was right before she slept, she would touch herself until she came and then soon nod off.

Jack had gotten a hold of her medical papers and found out about her social and anxiety issues. Suddenly the way she acted made sense and Jack felt a sudden urge to protect her.

Jack continued to watch and get information about Liz, finding out more about her was like a drug. After awhile Jack broke into her home,she really should be more careful, her door was unlocked and the lock that was on the door was pitiful. Jack was elated to find diary's and personal journals, which he had copy's made of. Then he hacked into her computer to see what sites she went on and more information. His jaw dropped when he saw the sites for "fantasy rape stories" They where apparently stories about women who enjoyed being raped. Reading the diary confirmed it, she found the idea of being raped erotic.

That's when Jack knew he was going to kidnap Liz. Of course he knew she actualy probably didn't want to be raped, but the lie that she did was all too tempting for Jack.

Finally Jack had it all set up, he had every thing he needed, except of course, Liz.

It wasn't that hard to get her, she went to secluded places a lot to sit down and relax, or read a book or something alone. One of the places she liked to go was the woods, she went early in the morning carrying a book. She also almost always wore headphones when she goes out alone, never heard Jack coming.

Jack shoved the chloroform soaked rag over her mouth and nose, and waited for her to stop thrashing about. When she went limp he then kissed her on the forehead and carried her out of the woods and into his car.

When Liz woke up she was tired and groggy. She looked around the room and saw blackness. Liz was afraid of the dark, only her family knows that. Liz usually sleeps with her door open and leaves the hallway light on to let some light in her room.

'Who the fuck closed my door?'

Liz thought annoyed when a memory washed over her and she realized she wasn't in her bed but on some sort of table. She screamed as the realization this wasn't the familiar darkness of her bedroom came over her.

'O God, O God , O God'

Liz thought over and over. Not entirely sure she didn't say it aloud. Liz was a very paranoid child. In fact after she watched Chuckie when she was ten she didn't sleep in her own bed for a year. She also wouldn't sleep with her back turned away from the door when she slept until she was 14 because she thought someone would stab her.

Liz felt like she was 10 again and with certainty thought she was going to be murdered. Liz moved experimentally, 'not tied up' she noted. She was about to jump off the table when fear seized her.

'You don't know how far down it is, for all you know you will fall to your death. And if you don't then what? You walk around right? What if there is a pit? ' God damn it why the fuck did I read "Pit and the Pendulum."

Liz noticed she was sobbing and whimpering. She was having the worst anxiety attack she had ever had, each thought about what was in the darkness or how she would be killed. She curled up and let her self cry out.

Suddenly the door was opened and a dark figure came up to her. Liz felt like her heart was beating so fast it would just stop as the figure approached.

"P-Please" hysteria was thick in her voice

"Please d-don't kill me!"

Jack looked at the frightened girl and wanted to pull her into his arms and sooth her, shame he couldn't.

"Do what your told and I might not" Jack growled

Liz's sobbing let up a little. 'Maybe I can make it through' she thought hopefully.

The masked figure took a step towards her. Her hope drained from her body as he came closer and fear shot threw her again.

"Please don't hurt me!" Liz screamed horrified as she thought about what she would be told to do.

"Heh, do what I say with no fighting and I'll try to make it not hurt." Jack knew it was cruel, but needed.Jack saw the horror in her eyes and it made him aroused.

He decided to give her some mercy, he wouldn't torture her by coming over to her slowly. So he pounced on her quickly. Liz screamed and thrashed about at the sudden movement and then suddenly a body was on top of her knocking the wind out of her.

Jack quickly over powered her and had her wrist's tied behind her back, and ankles bound. He looked at his handy work for a moment before he cleared his throat to speak.

"Now for some rules bitch" Jack said

She cringed at the name

"I am going to fuck you, ain't nothing you can do about it"Jack said then paused to see the shattered look on Liz's face

"And if you fight, or disobey, You get a punishment"Jack said leaving another pause

"Why are you doing this" Liz asked horrified

Jacks hand moved extremely fast to grab Liz by her hair and bring her head close to his mouth.

"Oh did I mention you don't talk unless I tell you to? Silly me! And since you asked because I want to fuck that pretty little pussy of yours"

Jack threw her back by her hair and got out a knife.

"Please don't kill me" Liz said ,then immediately realized her mistake.

Jack held the blade near her neck.

"You don't listen well do you slut?" Jack growled then moved the blade to cut the spaghetti strap of her sundress.

"Oh well, I'll enjoy punishing you" Jack said

Liz was scared for what her punishment was and was thinking about all the horrid things he might do to her. Jack made short work of the thin straps then tore the dress at the front and pulled it off then threw it to the side. Underneath was a yellow and black striped strapless bra, and matching boy shorts.

Liz began struggling,Jack put the blade at the end of her bra between her tits.

"Keep struggling and you'll get cut" Jack said menacingly

Liz screamed, and Jack promptly back handed her. Liz saw stars and stopped moving.

"That's better" Jack said less menacingly as her cut away her undergarments. When she was naked he let his eyes wander on his prize. She was trembling horribly and was sobbing softly. Jack hoped up on the table and quickly grabbed Liz and arranged her on his lap so that he could deliver her spanking. Liz struggled in earnest which only got her a hard 'SWACK!' to her ass. She stilled after giving a surprised yelp.

Jack had planned to only give her ten slaps, but now with a a perfect view of her amazing ass he upped it to twenty.

"Your punishment, slut, will be 20 swats to that lovely ass of yours. If you struggle too much it will start over." Jack said as he tried to keep excitement out of his voice.

Liz whimpered and sobbed, she never felt so embarrassed or humiliated then right now. She wished he would just kill her.

"Got that bitch?" Jack said

Liz didn't answer.

Another hard swat landed on her right cheek. Liz yelped

"YES! I got it.." Liz stuttered out

"When I ask you something you answer, cunt" Jack growled in her ear.

"I'm gonna start now, you ready?"

'Just get it over ' Liz thought an willed herself to stop trembling, and calm down.

"Y-yes" Liz managed to squeak out

Jack then counted out the 20 swats, he knew Liz was trying to stay still, but she still bucked and fidgeted. Jack growled out several times to stay still and by 10 she was just trembling and sobbing.

He finally got to 20 and caressed the sobbing girls bright red ass.

Jack was very proud at how well she took it, he gave her a moment to let the crying subside a little as he caressed. When he noted her crying letting up he started shifting her over onto her stomach on the table.

Liz's parents never spanked her and the pain in her ass was terrible! More then anything though she was embarrassed this stranger had just spanked her like a small child. Liz became aware of her ankles being untied. Her relief was short lived as he flipped her onto her back (to her ass's discomfort) and pulled her closed to the edge and tied her knees to something on the table so she was spread eagle. Too exhausted to struggle much more than token, she just tried to kick off his grasp, ineffectively and sob.

The fact he was going to rape her finally set in after he tied her left knee. She began to try to kick him with new fear shooting threw her, but he soon had her tied the way he wanted.

She was bucking and kicking wildly, the site had him aroused so he decided to let her wear herself out.

After awhile Liz felt defeated and tired after her useless efforts and just cried softly.

"Feel better?" Jack asked, almost caring.

His tone enraged her and she bit her lip to keep the nasty words that threatened to escape her mouth. Blood trickled down her chin from her efforts.

Jack understood her efforts and was proud of her for it.

"Holding you tongue? Smart girl" Jack said amused

"You did very well during your punishment, I think you deserve a reward." Jacks smile turned mischievous when he grabbed for a chair and seated himself in front of Liz's sex. Feeling his breath on her shaved pussy made her jump and realize how vulnerable she was.

"W-what ar-" Liz started to stutter out.

"Shhh just relax. It'll feel good" Jack soothed

Jack thrust a finger in her soft folds and felt her tense and tremble more if that was possible. He searched for her opening, enjoying the sobbing whimpering noise Liz was making. When he found her opening he found a good bit of moisture and let a gave a large grin.

"Already wet for me, baby. Lets see if we can't get some more oil flowing."

His words made her want to die, she didn't like being talked to this way, she didn't like what he was doing. Yeah she reads fantasys, but she isn't like that! So why was she wet?

"Please, p-please sto-" she said between sobs.

"Sh, relax. Honey tell me, are you a virgin?"

Liz didn't want to answer. Of course she was a virgin, but she didn't want this stranger to know.

Upon not hearing a reply he thrust one of his long fingers into her pussy, earning him a startled cry.

"P-please! Don't!" she cried

"I asked a question, sweetheart"He said this while he curled his finger up to get to her G spot and gave a few pumps.

"Ah! Yes I'm a virgin Okay!" She just wanted him to stop, It felt good it shouldn't feel good. She could felt more moisture between her legs now and shame burned through her.

"Mm, your gonna be fun" Jack said then gave a hard thrust into her and earned himself a shreech. He felt her getting wet by his attentions, and found some moisture with his thumb and began to play with her clit. She bucked, this made Jack chuckle and he knew it infuriated Liz.

'God, how does he know what I like.' Liz pondered how this stranger who kidnapped her was giving her so much pleasure. Of course she couldn't have know Jack studied how she touched herself at night. She tried so hard to block out the sensations, Once Jack gave a sudden hard thrust in her pussy , a low moan escaped her lips. Her face was crimson. She wished she was anywhere else as the pleasure increased and she felt her orgasm getting closer.

Jack felt her getting closed, and increased his attentions on her clit. The change drew out a moan from Liz, as she felt herself get close.

"No, no, no, pl-EASE! STOP!" Liz cried and sobbed as she bucked under his attentions.

Jack chuckled at Liz. 'So adorable' he thought.

"Honey, I'll stop when that pretty pussy comes all over my hand"

With that jack increased his efforts. He still heard Liz's pleas to stop, but they soon became unintelligible. Then Liz let out a scream and her pussy clamped on Jacks finger as she came.

'God, she's beautiful' Jack thought as waves of her orgasm washed over her.

When it was over her face was red and she was loudly sobbing. Jack felt accomplished and pulled his finger out of her sopping pussy. He the put it in his mouth. 'Sweet' Jack thought. 'Like her'.

"Did you enjoy that?" Jack asked, triumph clear in his voice.

Liz saw red as her embarrassment turned to rage. 'How dare he ask that!'Before she could think over the consequences Liz responded.

"You think I liked that?" Liz cried with a tone of hysteria

"You think I liked that, you sick fuck!" She screamed

Liz couldn't believe what she said. 'O God, why did I say that? Why the fuck did I say that!I really am going to die!'

"I-I-I'm sorry!" she managed out and began sobbing again.

"I-I didn't mean it, I'm sorry." Liz repeated

She looked in his eyes to gauge his anger, but instead found a mischievous smile that almost scared her more.

"That's,alright we'll just have too do it over and over again until you thank me properly."

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8 Comments
AnonymousAnonymous8 months ago

I loved the story although there is part of me that is pretending they actually had been talking for a while & he found these things out through consensual means. only other thing was spelling & grammar, but I was able to ignore it after a bit

AnonymousAnonymousover 2 years ago

Spelling mistakes make this hard to read.

AnonymousAnonymousalmost 11 years ago

Good one

coyote3kcoyote3kalmost 11 years ago
interesting start

I like Liz with her shy demeanor and her secret desires. She's an interesting character. I hope you keep writing.

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