Archive of Our Own

Chapter Text

Nate wouldn't consider himself an evil person, he was a loving dad and a kind and helpful neighbor. If you asked anyone to describe him they would have nothing but kind things to say. Infact Nate would never even be thinking about the things he had been if it wasn't for Sydney. That girl was a demon she was cruel and mean and had spent the last 5 months doing everything she could to break his daughter. Whether it was spreading the constant harrassment or spreading the rumors that she was a slut who had slept with multiple guys it was never ending. All Nate could think about recently was how badly he wanted to put her in her place to make her regret ever targeting his sweet and kind daughter.

Despite his growing need for revenge Nate had managed to not do anything hasty by reading parenting books and learning to cook, he was spending most of his time with his beautiful wife Anna and his lovely daughter. Nate was better now he could live like this forever. Fuck what the doctors had to say he wasn't a psychopath. He was a regular guy and he was a dad.

Nate checked the clock 3:45 Anna would be back home with Grace he had made his daughters favourite meal to celebrate the beginning of the weekend. Nate heard the door open and removed his oven mits to go greet his family. When he entered the entrance he only saw Grace for a couple seconds before she was speeding up the stairs and into her room.

"Whats wrong with her?" Nate asks before kissing Anna.

"That girl who's been bullying her played a mean joke on her today"

Nate felt his body fill with rage.

"What did she do?" He asked as calmly as he could

Anna took a deep breath.

"She filled her locker with used condoms and had a large banner with a lewd drawing of her pleasuring multiple men on it."

Anna began to tear up and was soon bawling uncontrollably.
"It's okay my love there is nothing we can do about this bully but we can make sure our daughter is okay, that's the best we can do as parents." Nate said sweetly

Nate had said what he needed too in order to console Anna who had gone upstairs to deal with Grace. He was lying, every last thing he had said was a lie. There was something Nate could do to help his daughter, he knew exactly what he had to do to make the bullying stop. Nate had a target Sydney and he was going to make her regret choosing to bully his daughter. In fact Nate was sure Sydney would spend the rest of her life regretting it, he could promise that.

Nate lied down on the bed while his wife rode him hopping up and down while moaning. Normally this would be the best part of Nate's day but tonight all he could think about was Sydney. Nate wasn't stupid he knew that kidnapping a high school girl was going to be easy and that if he wanted to get away with this he had to be perfect. He was listing the things he was going to need to make his plan work.

-Somewhere soundproof and isolated to keep her
-Rope and handcuffs to tie her up with
-Gags to shut her up

Those were the bare necessities however Nate had some other things in mind that wouldn't be cheap. But first things first Nate decided he'd spend the next couple of months collecting all the things he would need.

3 months later

Nate drove at the speed limit through the countryside and kept going until he arrived at his destination. It was a house he had had a friend buy using an offshore account, completely untraceable.

Nate got out of the car whistling to himself and grabbed the bag on the passengers seat. He continued to walk up the driveway, he pushed the key into the door and pulled it open. It was early in the morning so he walked over to the kitchen and made himself a nice hot coffee. Once that was ready he made his way towards the stairs to the basement.

He reached a high tech door and put in the code, it also had a key hole for when Nate wanted to get in quicker. He walked through the door into the sound proof basement. He continued to walk forwards until he saw her.

Nate wasn't a pedophile he had never had an interest in young girls, but as he stared down at the crying gagged teenager infront of him he couldn't help the boner that began to show through his jeans.

Sydney was gorgeous she had beautiful straight blonde hair, perfect tits and a fat ass. She was 5ft 4 and she had the face of a supermodel. She probably would have lived a great life and had boys falling over themselves to date her.

To bad Nate had gotten to her first.

"Hey there baby girl" Nate mocked Sydney.

"UUUUUGHHHH!"

"You know I can't understand you like that honey" Nate chuckled.

Nate walked over to her and unbuckled the gag allowing Sydney to talk.

"Who are you? Please let me go...I won't tell anyone I promise...I just want to go home" Sydney begged

Nate loved hearing her beg and she was going to beg so much more, he couldn't wait.

"My name doesn't matter, the only thing that matters is that your mine."

Nate undid his belt and pulled his pants down, he then slid his underwear down his legs and stepped out of them. This revealed his hairy balls and dick, Nate didn't have the largest penis but it sure wasn't small.

Sydney stared at it with absolute terror. Seeing his erect cock made her realise what was going to happen and she began sobbing and trying to free her arms from their restraints.

"tut tut tut, lets not do that, your mine now and that's never going to change." Nate smiled cruelly as he turned around to empty the bag he had brought with him.

"Please don't rape me my dad has money he can pay you whatever you want..Uh!"

Nate replaced the gag before turning back around.

"I don't want your daddy's money, I want your cute 16 year old body baby."

He emptied the bag letting all the stuff fall right where Sydney could see it.

Sydney's eyes grew when she saw the contents of the bag.

On the floor was a butt plug,lube,multiple dildos of different sizes,a set of 6 anal beads each one getting larger and a whip.

Nate reached for the butt plug and the lube he then flipped Sydney on to her back as she began to struggle. Nate ignored her it didn't matter how hard she tried to stop him he was way stronger.

He opened the lube and squeezed it right over Sydney's tiny perfect tight asshole. He then used his pinky to push the lube deeper into her, Nate pushed his finger back and forth fingering her until he thought she was lubricated enough.

"UGH!"

"I hope you enjoyed these 16 years of having an empty asshole, because after today you will never have an empty one ever again." Nate placed the butt plug at the entrance to Sydney's asshole and pushed. Her sphincter was tight and even with the lubricant, pushing the plug in was really hard.

He used all his strength pushing the plug down into the tight anal ring. He pushed for 2 minutes without stopping, the muscles in his arms sore from the effort.

"AUUGGHHH!"

After what felt like forever he felt the plug slip from his grasp and sink into her once untouched hole.

"That is one tight hole! Can't wait to fuck it!"

"NUGHHH!"

The plug wasn't very large at least not compared to the ones Nate planned to force into her backdoor but Sydney still sobbed and thrashed regardless. She probably didn't enjoy the alien feeling of having her butt plugged, for Sydney it was like needing to shit but being so constipated you can't push any shit out. Her stomach was cramping from the anal intruder and she was screaming her discomfort.

It didn't matter what Sydney liked or didn't like she was going to wear the plug and if she thought this tiny little plug was bad she was not ready for what Nate had in store for her.

Nate picked up the rest of the sex toys and placed them on a shelf in the basement. When he noticed Sydney's face soften he smiled.

"Don't worry we are still going to use those just not today." Sydney began to cry again, Nate didn't think there was anything more beautiful then a crying girl.

"Now we'll finish today with your first vaginal rape and then you'll be alone till tomorrow, how does that sound?" Nate knew Sydney would be against it but gagged there wasn't much she could do to voice her displeasure.

He grabbed the lube and squirted it all over his cock, smearing it all over so his entire dick was wet. He was dripping precum from his urethra and he was ready to rape her. Nate did it slow he found the entrance to her pussy and placed his dick ready to breach her. Taking her virginity was an important moment it would be the first way he broke the poor crying girl.

With one violent plunge he entered the screaming girl, the lube helped him slide his dick in but it was still a challenge to rape her. 

He ripped through her hymen feeling it rupture and seeing blood leak out of her vagina, her virginity was his which meant so was she."

"Wow Sydney your tight!"

He pulled out his dick was coated with her virgin blood and then he pushed back in a little harder this time trying to penetrate her deeper.

"AUGH! AHH AH AH!" her gagged crying was so fucking hot.

Nate reached down between her legs and located her clit, he started to squeeze it and rub it with his fingers.

"NUGH! STUGH! UGH!"

"Fuck ya baby your so wet for me, ugh you love being raped by my dick!"

Nate used his free hand to grab Sydney's breast and start teasing her nipple.

Every time he penetrated her his legs hit her thighs creating a whap sound.

"Cum for me baby, you know you love this. You love being raped."

"NUGH! OO! OooUUH! AAAH AAHH ugh oooua eh aahh UGHHHHH!" Sydney's eyes rolled into the back of her head her breath got short and she threw her head back in frustration as the orgasm engulfed her body while she came.Her pussy squirted violently and her entire body shook.

Nate also started to pant hard he was about to blow, he pulled all the way out and then pushed his dick as deep into her vagina as he could.

"Time to fill you full of my love juice bitch."

Nate came hard filling her with sperm, his dick was a machine, a drill determined to smash through Sydney's defence.

"AGGH!"

"Oh ya scream baby. Scream for me. Scream while I rape your pussy."

Nate used his cum as more lubrication allowing him to fuck her quicker his dick sliding in and out of her easily thanks to all the lube,cum and blood.

"I can come at least 3 more times, Sydney so you better get comfortable."

Sydney was anything but comfortable tied up in a frog position her hands pulling her legs apart wrapped in rope while a 40 year old man fucked her vagina. She was miserable, she wouldn't stop crying, her thighs jiggled every time he pounded into her.

"Oo aaa nugh ooo aaa UGHHH!"

Sydney came again, she hated her body for betraying her like this.

"You're such a slut baby, a 16 year old slut. UGh!"

Nate came for the second time he pulled his dick out of her vagina his sperm was leaking out of her sore hole.

He was breathing hard, fucking her is fun but it's lots of exercise. He was sweating and out of breath, he got up and walked over to the fridge next to the sink. He opened it and pulled a bottle of water out. He downed the entire bottle he gulped hard, letting the water rejuvenate him.

"That sure hit the spot."

Nate walked over to the shelf with the sex toys and grabbed a ring gag off one of the middle shelves.

He walked back to the mattress where Sydney was sobbing so hard snot was dribbling out of her nose.

Nate got on his knees and unbuckled the ball gag.

"Uuu...please...stop...fuck...stop! you took my virginity I was saving that for my boyfriend Carter!"

"You don't need a boy baby when you have a man."

Nate expertly put the new ring gag into Sydney's slutty mouth.

"UGH! FUGH YUGH!""

"No but i'll fuck you baby."

Nate pushed Sydney's head down on to his dick. She began to gag but he held her there halfway down on his penis.

"You give a terrible fucking blowjob. Carter must have been fucking other girls on the side"

Nate lifted her head off his dick and she gasped for air she was terrified hyperventilating and coughing.

"You gotta use your tongue Sydney. Lick my dick and suck it. Let's try this again"

He pushed her head down on to his dick and waited, she began to gag terribly saliva dripping out of her mouth. Nate didn't lift her up this time he wanted to give her time to realise she had to give him a good blowjob if she wanted to breathe.

He lifted her up off his dick after watching her choke for 2 minutes.

"If you don't wanna breathe you can tell me baby."

"UGH PLUGH UGH NUGH uuugh!"

"Come on Sydney I know you can do it. Maybe 3rd times a charm"

"NUGH uuck uuck ugh oouck uuck"

The third time he forced her head down she actually tried, she sucked him as hard as she could with the ring gag holding her mouth open. She licked the top of his cock head and pulled her tongue down the length of his dick stuffed down her throat. She licked him with as much vigour as she could muster trying in vain to please Nate with the hope he'd let her go.

Nate moaned and grunted and came in her mouth.

"Swallow my sperm Sydney."

He was about to pull out when he thought of something genius he couldn't not do.

His dick relaxed and he began to piss in her mouth, the warm liquid mixed with his sperm filling Sydney's mouth till it was full.

He pulled his dick out and she started to have a coughing fit. Cum and piss spilled out of the open hole in her mouth.

"Your blowjob was still pretty trash, but don't worry your pretty little head about it I'll train you till you get better."

"UGH Whugh I ugh uck."

Nate returned to her pussy and shoved his dick back inside.

"Thanks for the new lube baby it makes fucking your pussy so much easier."

He fucked her again and again and again. Savouring the strangled gasp Sydney created every time she was penetrated. Finally he came for the 4th time inside her and pulled out his cock which was dripping sperm. He got up and walked over to a table to grab a towel and clean himself off.

"Wow that felt great, I've never taken a girls virginity before but I can see the appeal." Nate laughed as he picked up his coffee and took a sip.

"I have to go now baby, but don't worry slut i'll be back early tomorrow and we can have a lot more fun."

"You have food in the bowl and water so that should be enough"

"May be hard to eat and drink with that ring gag but i'm sure you can figure it out bitch, your a smart girl."

As Nate left the basement he saw Sydney lying there on the matress covered in cum and piss her body shaking as she cried. Her big fat 16 year old ass jiggling and bouncing while she wailed in agony.

It made Nate chuckle, he loved seeing her miserable. He walked out the door and locked it behind him as he climbed up the stairs he couldn't help thinking about all of the things he couldn't wait to do to his 16 year old captive. Anal raping her was next he'd probably do that in the next couple days he wanted to focus on her pussy first. But he'd also watched lots of porn and wanted to really break her he didn't just want to rape her he wanted to transform her. Nate was going to destroy poor Sydney in every way possible every part of her body was going to suffer, every hole was gonna be stretched.

Her body was his. He was going to ruin it, he was going to ruin her.

Chapter Text

This is what Sydney,Nate,Grace and Anna look like.

"I love you Honey." Nate yelled out before closing the door and getting into his car.

He drove with purpose no longer needing to use his gps to reach his destination. It had been 4 days since Sydney's mysterious disappearance and the police had already begun to stop searching. Nate couldn't blame them he had comitted the perfect crime, there was zero evidence to find, no cameras,no dna and he had purchased a brand new car that he had had painted and then disposed of when he kidnapped her.

Nate knew there was no way the cops would ever find him, he turned into the parking lot and turned off his car pocketing the keys and walking towards the sex store. When he entered the little bell on the door rung alerting the guy at the counter.

"Hey yo Michael back again?" Gary said kindly

"It's for work got a job filming for a porn shoot and they asked me to pick up a couple things." Nate smiled back at Gary before heading down the farthest aisle. His name wasn't Michael and he didn't work in the porn industry but this guy didn't need to know that. The less he knew about Nate the better, Nate kept walking until he found the section he was looking for he stared at the large selection of butt plugs and grabbed the next size of the one currently inside Sydney's teenage ass. He then made his way to dildos and grabbed a blue one that was 5 inches that would work nicely.

"Hey Gary where's the stuff used for enemas?" Nate asked eyeing the store clerk.

"Those would be right over here." Gary walked over to a shelf and grabbed the enema gear.

"Thanks so much you're a real life saver." Thanked Nate while pulling out his wallet, only cash that way this couldn't be tracked back to him.

Nate grabbed the bag of items and walked back towards his car.

It was a long drive but Nate finally arrived at the house, he entered the door and immediately headed towards the basement. Once he opened the door he was assaulted by the pungent smell inside it. He turned his attention to Sydney who was miserably sleeping on the floor. Nate walked over to the hose that was attached to the sink, he brought it over to Sydney and sprayed the naked teen with freezing cold water.

Sydney was startled awake and stared at Nate with a look of absolute hatred. Her hair was knotted and a mess, her eyes were puffy and red from crying and some hair had started growing over her vagina. This Nate loved, he had decided he was never going to shave her down there he wanted his cute 16 year old captive to have a big hairy bush at all times. Something about knowing how much she hates it and wants to shave it makes forcing her to have one so humiliating and perfect.

"How's my little slut doing today?" Nate mocked

Sydney was gagged and could only grunt and moan, Nate preferred her like this. He would ungag her sometimes to hear her cry and beg but mostly he would rather she was gagged.

"Today's a big day for you and me, today's the day I fuck you in the ass"

"NUGH!"

"Ya baby gonna take your butt virginity."

Sydney was shaking, she clearly didn't want that but who cares what she wants.

"But I don't want to get my dick dirty I have a wife who deserves a clean man, so I gotta wash you first." Nate finished his sentence by attaching the enema nozel to the hose and walking towards Sydney.

He pulled her towards him and grabbed the butt plug, with one tug he pulled it out. Nate didn't want to leave Sydney's asshole empty for too long so he quickly pushed the enema nozel into the winking hole. He then grabbed a bottle of soap and poured it into the tub the hose was connected to.

"Now this is going to be cold and pretty uncomfortable so feel free to cry, it's more fun that way." Nate turned the hose on and watched the water speed down the hose and into Sydney's virgin guts. 2 minutes later Sydney started to whine and struggle trying to dislodge the nozel to bad for her it was made similar to a pear of anguish and once opened couldn't be removed without being closed first.

"UGH AUU! Plugh!"

Nate watched the squirming girl on the ground as her stomach filled with freezing cold water and got larger and larger. The swelling continued until she looked about 3 months pregnant. Nate expected that was enough water and turned off the hose. He placed his hands on her stomach and grabbed her tits squeezing them and making her scream. Then just for fun Nate began to push down on her stomach he looked between her legs and saw her asshole try to push the nozel out only to fail. He loved feeling her jiggly belly sloshing full of water.

"Mugh uuh"

Finally after forcing her to hold it for 30 minutes Nate released the nozel and let her expel her guts into a large bucket. It took 5 minutes for the swelling to go down and for Sydney to stop panting in pain.

Nate sat down and unbuckled the gag allowing Sydney to talk.

"Did you like the cleaning baby?"

"Ah ah hugh ugh. NO! It hurt please don't do that again...please just let me go home" Sydney said weakly

"Oh don't be such a baby that was nothing you don't even know what pain is yet." Nate finished his sentence by spanking Sydney.

"OW! Fuck You! Just stop...Just let me leave...I hate it here!" Sydney screamed in anger

"It doesn't matter if you hated it, you will be given an enema every day for the rest of your life. So you better get used to it." Nate laughed unbuckling his jeans.

"Now it's time to fuck your big juicy butt." Nate positioned himself behind Sydney and slowly positioned his dick with her ass.

She was wet and lubed from the enema which helped with the insertion but wow was she tight, her 16 year old ass was clearly not ready for Nate's dick

"Ahh! OW! Wait! stop! Don't do that! you're hurting me! STOP!"

She could wail and beg as much as she wanted he was still going to fuck her ass. Sydney had started to push trying to keep Nate out of her ass.

Trying to fuck her ass was nothing like when he fucked her pussy, her anal ring was hard like a wall and stopped Nate from getting his dick any deeper into her. She was scared and trying to avoid this and straining her muscles this made made penetrating her nearly impossible.

"You can fight this as hard as you want baby, it's going in."

"No please...not my ass it's wrong!"

"No it's right baby, your ass is just another hole for me to conquer"

Nate pulled out and pushed in again this time harder with more intensity. He knew how to solve this problem, just like when someone is trying to push a large turd out of their ass they can't push forever.

Despite her impressive resolve and stamina Sydney couldn't keep him out forever and the split second she had to take a break he would ram his dick up her poop chute.

Sydney held out for 3 minutes before finally being to tired to continue and once he felt the tension to ease, Nate took the opportunity to shove his dick up her in one quick brutal thrust.

"AHHH! WAIT! no not in there anywhere but there!"

Now that he was in he began to slowly piston his cock out and then in slowly fucking her gaining momentum and starting a rythmn.

"Take it out! Not my ass! NO!"

Nate fucked her hard speeding up his thrusting and using all his strength to go deeper.

Sydney screamed in pain unable to form coherent words as she tried to pull her legs and arms free from the ropes.

"Oh your insides feel so good Sydney."

His dick was unstoppable it shot forwards with every thrust battering her tight rectum. He reached for her pussy and started playing with her clit.

"Now be a good slut and cum while you get pounded in the ass."

"NO! I won't cum not from this! Let go! Get off me! Just die!"

Nate fucked her relentlessly he could now pull dick completely out of her ass and then shove it back in her ring was red and her insides were slick and ready. He played with her pussy rubbing it and and pinching it. He listened for the sounds he loved to hear the proof Sydney was about to squirt like a water fountain.

Stop! It really fucking hurts Ugh no ugh stop touching my clit! Ugh OOO Uuah OOOO OH NO! NO! NO! OOOO AHHH UGHHHHH!"

"Knew it look at you cum from having your ass raped you disgusting slut"

She was incoherent and in absolute agony, she didn't want to cum she hated Nate's dick in her ass but she couldn't stop her body from reacting.

"Now it's my turn."

He grunted and came into her asshole, filling her guts with his sperm.

The sperm made her hole even more slippery and now Nate was just plunging in and out fucking her easily.

"OOOOO AAAHH! PLEASE! PLEASE! pull your dick out! UGH UGH OOOOAAA UGHHHH!"

She came again this time even harder, her vagina was soaking wet and her pussy was opening and closing like a little mouth due to the orgasms.

Nate pulled out of her ass huffing and puffing.

"Wow fucking your ass is a crazy workout."

He let go of her clit and stroked her face.

"please...ow...please" she was crying

"Does it hurt baby? does having your virgin 16 year old asshole raped hurt?"

"YES!"

"You know what I've decided to let you go, I'm sorry I hurt you."

"Really OMG thank you so much!"

"Ha HA HAH HA HA HA HA HA"

Nate burst into laughter while stroking his dick.

"I know you are young but you can't be this naive or stupid."

"WHAT YOU WERE LYING!"

"That's right baby I'm never letting you go I'm gonna fuck your perfect body everyday."

"NO! NO! NO! AGHHHHHHHH!" her scream was full of anger

Nate took the opportunity and shoved 3 fingers into her mouth and down her throat.

"ACK!"

He pushed his fingers in and out fucking her throat making her gag, he pulled his fingers out and replaced them with his dick. He pushed it into her mouth as deep as he could."

"I love when you gag on my dick bitch, do you like the taste of your asshole Sydney?"

"UGCK ACK ACK UGHCK"

"Your lucky I gave you an enema, your ass was squeaky clean when I fucked it, the taste should be fine."

Nate pulled out of her throat and returned to her ass pushing forwards and penetrating her again.

"stop...it never stops...stop."

Once he had gotten deep enough he pulled out his cock and then plunged it back in. He continued his brutal rape speeding up and pushing his dick as deep into her as he could.

He loved how her asshole squeezed trying to push him out, the shaking sobbing body he was inside made his dick feel incredible.

Nake fucked her harder and faster really sodimising her ass hole. Nate wanted to make sure her first anal experience hurt as much as he could that she would never forget it.

He fucked her up the ass for 40 minutes listening to her sobs and hiccups. He plunged in for the last time of the day as deep as he could and then he came again coating her shitter with even more of his sperm.

"Oh yeah, fuck yeah."

"fuck you...i hate you..."

He pulled out and reached into the bag to grab the new plug.

"Fucking that tight hole was a hell of time but you do you know whats better than that?"

"Please stop it's too much I can't take it anymore."

"Go on answer"

"I don't know fuck you!

"Stretching your tight little hole."

"NO! No! no...please don't I hate having something inside there!" Sydney hiccuped and cried but Nate still shoved the new larger plug up her rear with zero mercy.

"Your hole will never be tight again when I'm done with it." Nate promised

Nate not ready to end his fun positioned his dick at her vaginal entrance and asked her if she was ready, before getting an answer he shoved his dick forwards filling her vagina with his manhood.

"AAAAAHhhhhhh! STOP! I HATE YOU!" Sydney screamed in anguish struggling harder.

Nate smiled as he fucked her, his dick slid in easily thanks to all his sperm and her saliva working as lubricant.

He fucked her pussy for 5 minutes thrusting as hard as he could, he played with her clit the whole time. 

"OOOOO NUGH UGHHHH! UGHHHHHH! AUHGHHHH!"

After her 6th orgasm they came slower, it was no longer pleasure Sydney was feeling it was pain it was to much overstimulation and she went from moaning to sobbing uncontrollably. When she came it was screams of guttural misery and pain, her tiny clit barely visible was erect and ready. The non stop squirting added more and more lubrication this made fucking her pussy a walk in the park.

Nate fucked her for another 10 minutes and then he filled her cunt with some baby batter. He pulled out and felt his flacid dick, not a bad day of fucking.

"Wow that was great, you are a pretty nice fuck."

Sydney couldn't even respond she was so tired she just lay there. Nate wasn't done yet he reached back into the bag and grabbed the last item the blue dildo he lubed it up and pushed it in. He fucked Sydney mercilessly with the blue dildo, it was shorter then his dick but it was thicker and if he wanted to stretch her pussy so he could fist it then thickness was what mattered.

"It's to big it hurts please...pleas...have mercy"

Nate had no mercy and he didn't stop he fucked her until he felt her pussy was loose enough that the dildo could enter easily.

"Inch by inch it may be slow but I will stretch these holes beyond repair." Nate got up and walked over to the shower to clean himself off, after drying his body he put his clothes back on and walked over to the the shelf near the sink. He filled her water bowl with water and poured some dog food into her food bowl. Once she had something to eat and drink Nate left the basement.

As he was walking towards his car he received a text on his "work" phone.

(No one)I got the gynochological chair you asked for

(PornMan) Seriously thank you so much!

(No one) Don't thank me this ain't charity you pay me I get what you want

(PornMan) still the same cost we decided on?

(No one) Nah 100 extra getting it out of that abandoned hospital wasn't easy had cops patrolling it

(PornMan) Fully understand 100 extra its a deal i'll come pick it up on Sunday

(No one) Pleasure doing business with you

Nate put his phone away and punched his fist into the air.

Poor poor Sydney you are about to be in a world of hurt.

Chapter Text

"UGGGHHHHHHHHHH!" Her muffled scream had hit a new octave after hours of screaming Nate had thought she would have started to lose her voice but apparently he was wrong.

At first her constant wailing hadn't bothered him but after 3 weeks he was starting to get tired of it. Despite his sore ears Nate couldn't really blame the pretty 16 year old infront of him for her annoying screaming. Sydney was strapped to the gyno chair like she had been everyday for the last 2 and a half weeks. Her arms were tied behind her uselessly while her legs were in stirrups that had been pulled as far as possible without dislocating her legs. Sydney was bashing her head against the headrest while flailing her legs desperately trying to kick Nate. It was such a fun sight to see her moving her legs knowing there was nothing she could do.

Her hair once a beautiful sunny blonde was now full of dirt and had grown a couple inches longer, her bottom hair was also growing beautifully. Sydney's 16 year old pussy had begun to grow a nice full blonde bush. Nate loved it, he loved telling Sydney how much it had grown over the last couple weeks. He would even spend time grooming it using a hairbrush to keep it nice and pretty.

"UGGGGGGGGHHHHHHHHH!" She clenched her hands into fists and strained against her bondage. Nate would never get tired of watching her react like that. Nate returned all his attention to his task he had already managed to get 3 of the stringed balls up into Sydney's asshole but he still had 3 more to go. Each ball was a little larger until the largest one which was the 6th ball.

"I don't know why you're complaining I told you we are going to stretch this hole till it's unrecognizable" Nate finally managed to get the 4th ball in punctuated by Sydney's strangled scream of despair.

"You probably think this is the most it can stretch right. Ha! Wrong i've watched pornstars push things 10 times bigger than this up there shitter." Nate began to work on pushing ball 5 in. He lubed it up first and then placed it over her asshole and began to push it in. Slowly he applied steady pressure, Nate was working against Sydney's muscles which were trying to stop the insertion, to bad for them Nate didn't give up easily. He continued to push a little harder feeling sweat slide down his brow.

Nate wasn't the only one sweating, Sydney's body was drenched in sweat her face covered in tears, her body was violently shaking and she was gasping between sobs. Nate continued the battle against Sydney's asshole for 10 minutes until he finally felt her muscles soften she could no longer push she was out of energy now was the time for attack. Nate put all his strength into this final labouring push. Her asshole lost the battle and the 5th ball entered the once virgin hole.

"UGGGHHHHHHHHHHH!" She had bitten so hard into the ball gag she chipped her tooth. She began wailing in pain but if Nate had ignored her pain for the last 3 hours why would he care now.

"One last ball sweetie, you're so close. Don't worry after a couple months of this your ass will be so beautifully stretched you'll put all the porn stars to shame."Nate grabbed the last ball and prepared for the task at hand.

25 minutes later Sydney's ass was full of the balls, Nate could see the small bulge in her stomach showing where the balls were shoved up her ass. Nate got up off the stool he was sitting on and walked over to Sydney he unbuckled the ball gag and Sydney spat it out. Nate slapped her for that.

"OW Omg please stop it hurts so much my asshole hurts so much please pull them out please!" She begged. She had stopped screaming at him and had started to ask nice and docile as if she thought being compliant would make it easy for her.

"Sorry Sweetie i'm not that kind of kidnapper, no stolkholm syndrome will help you here." He was being truthful he had zero sexual interest in Sydney, like he said he wasn't a pedophile all he wanted to do was hurt her.

"You can rape me all you want i'll be your wife and make you food. I'm a great cook...just please I can't take it anymore."She said that last part so softly her voice broke and tears began to well in her eyes.

"No thanks, this is more fun. I've enjoyed these past weeks immensely stretching your vagina and asshole is the most fun i've had in years."

"We aren't even close to where we need to be but I have faith that we will get there. Next year on the anniversary of your kidnapping we will look back at today and laugh at how small those holes between your legs were." Nate finished his sentence and got up to go into the drawer and grab something.

"a year? You can't be serious no no no no no no." She was spiraling in her fear she wet herself and the pee arced through the air landing on the floor in a puddle.

"Thank you so much for reminding me what my main goal of today is. As much fun as I've had with your sex holes I made a pact that when I had you I would work on all your holes. There's 1 hole that I have ignored for far too long." Nate pulled a metal case out of the drawer and placed it down on the table right next to his stool in front of the gyno chair.

"What are you talking about? You've used every hole." She said confidently

"Are you sure? Ok tell me one thing that was done with each hole." Nate said playfully she didn't even see the trap.

"Ok you raped my vagina."

"Pussy" Nate corrected

"What?" she asked

"Young girls have vaginas, sluts and toys have pussies. Start again."

"Ok you raped my pussy."

"sir or mr or you can call me master." He added

"Fuck you I'm not doing this, it's humiliating." She responded angrily.

"Ok then I'll pull those balls out of your butt and we can start using a new toy to stretch your slutty backdoor."

"NO! I'm sorry sir. Master raped my pussy." She said fearful of more anal stretching

"That's one continue"

"You pushed a butt plug up my asshole sir"

"Stop you made a mistake." He said

"What! what now? I did exactly what you said." Sydney yelled angrily

"Young girls use assholes to shit but you don't shit you are given an enema. Your hole isn't used the way a young girls is so it's not an asshole it's a butt pussy." He smiled

"You can't seriously want me to call my asshole that?!" She responded defiantly

Nate got up and walked towards the shelf where all the new toys were and grabbed a rather large dildo.

"WAIT! I'll say it! I'll say it! Master forced a butt plug into my butt pussy." She screamed terrified

Nate left the toy and walked back to the gyno chair "That's 2"

"And finally sir forced me to use my mouth to give him a blowjob today."

"You really are a dumb 16 year old. Young proper girls have mouths that are used to eat and brush their teeth and laugh. You aren't a girl anymore you don't have a mouth you have a cum hole it's only purpose is to give blowjobs and swallow cum." Nate loved how red Sydney's face was getting.

"Master forced me to give him a blowjob using my cum hole. Thats 3 thats all my holes." she said hopefully

Nate smiled cruelly he enjoyed seeing the fear on her face it made all this worth it.

"You are right you counted 3 holes but girls don't only have 3 holes, you like most people including pornstars have forgotten one of the most unique and fun holes a girl has."

"What hole is that?" She asked dreading the answer.

"Well your peehole of course, even the most masochistic women hardly ever touch that hole but you are gonna experience all the pain that can come from stretching the urethra." Nate opened the case and pulled out a small metal rod it wasn't very long or very thick. Sydney wouldn't even feel it if it was going in her ass but it wasn't going in her ass.

"NO! not that hole you can't be serious its to small! YOU'LL kill me!" she pleaded with her captor but he wasn't budging.

You can scream and plead and beg but it won't change a thing your pee hole is about to no longer be virgin.

He inserted the speculum and opened her pussy up wide.

Nate ignored Sydney's begging and screaming and swearing all he cared about was what happened next. He found the tiny 4th hole and began to slowly insert the sounding rod inside her. She bucked and screamed and struggled harder then she had in weeks to escape her bindings.

"NO please you're going to ruin me! STOP! I HATE YOU! I HATE YOU! FUCK YOU! FUCK YOU FUCK YOU FU-AHHHHHHHHHHHHHHHHHH!"she screamed as Nate twisted the sound inside her. He pulled it out and then pushed it back in, in and out in and out in and out. Over and over again fucking her little pisshole watching spurts of yellow liquid coat the sound as she lost control of her bladder in so much pain. Nate pulled the sound out slightly and then pushed it back in farther this time, the sound wasn't long enough to enter her bladder but one day he would be using one that was.

He fucked her mercilessly with the sound for 20 minutes straight enjoying the absolute agony Sydney was engulfed by. She had stopped screaming and was now just repeating the same fuck you over and over again. Nate didn't care if she hated him it wouldn't change any of his plans for her. He was going to destroy every part of her body and this was just another step forwards.

Nate pulled the sound out of Sydney's throbbing urethra and smiled at the inflamed red surrounding it. He placed the sound he had in his hand on the table and reached into the container to grab the next size up.

"no please you'll destroy it if you stretch it too much. just rape me." She was weak from the hours of torment but she was still trying to beg, cute.

Nate lubed up the next sound and began fucking her peehole she broke into sobs unable to do anything to stop him. Her legs and arms were strapped to the chair, her legs were spread wide and she couldn't close them no matter how hard she strained and her chest was strapped down. Sydney was helpless and the realisation caused her to cry even harder.

Nate heard her whisper a prayer while he fucked the sound back and forth slowly stretching Sydney's most pure and precious hole, a hole she had probably never even imagined in her worst nightmares would be treated like this.

"Pray all you want God can't help you. You're in hell and i'm in control." Nate pushed the sound in faster and harder putting all his force into the push and making sure to pull out as fast as possible.

25 minutes later Nate pulled out sound 2 and threw it away. He proceeded to grab sound 3. He heard a strangled garbled cry from Sydney but he was in the zone now. He looked at her piss hole and it was beautiful the inside was red and scraped raw and the entrance was throbbing just like her butt pussy. Nate pushed the third sound in even slower it was thicker and meant to stretch her hole even more and Nate knew it would take longer to get it all the way in. He spent a good 5 minutes slowly pushing it in and out letting the muscles stretch to accommodate this new size. Eventually he felt the effort soften and began to push the sound in deeper, once he managed to get it all the way in he pulled it out and began the same routine he had done for the last 2 sounds.

Nate after his arm got sore pulled the sound out as piss shot forwards and splashed him in the face he licked his lips and threw the third one away.

"Please is it done are you done." Sydney asked weekly

"sir."

"are we done sir please it hurts so much." She corrected herself

"You tell me." Nate asked before grabbing the cord connected to the balls inside Sydney's butt pussy.

"WAIT YOU CA- AHHHHHHHHHHHHHHHHHHHHHHGGGGGGGHHHGHHHHGGGHHG!" She shrieked in horrible agony while Nate freed all the balls in one quick pull. Her butt pussy was throbbing it was opening and closing and squeezing on nothing. The best part it was not returning to its original size, the mucus was dripping out of her and landing on the floor joining the puddle of pee.

"Wow your butt pussy is beautiful it stretches so wonderfully and I love it when it gapes open. I can almost see directly into your stomach." He laughed

Nate grabbed a polaroid camera and took a picture of the mess in between her legs. He got up and showed the picture to Sydney.

"Does that look like an asshole to you?"

Nate slapped her face hard.

"Answer me when I ask you a question, does that look like an asshole to you?"

"no." Sydney answered sadly

"No it doesn't, does it look like the asshole a proper 16 year old would have. One who would only use it for shitting who would never disgrace God. A teenage girl's asshole should be small and tight." Nate spoke clearly relishing in Sydney's humiliation.

"yes master a teenage girls asshole should be small and tight." she replied robotically

"So what is that in between your legs then?"

"A butt pussy master." she stifled a sob when she said it.

"That's right, good job you're learning. I'm gonna save this picture for the future it'll help me see the progress we make every week."

"Yes sir"

"You are so beautiful baby your tits,your cum hole,your pussy, your butt pussy, your perfect hairy bush and of course your slutty little peehole."

"Thank you master"

"Your perfect" Nate returned after safely storing the picture, in his hand he had a new butt plug this one was the largest one yet and it had a hollow inside.

"This is called a tunnel plug it's gonna help stretch your butt pussy while still allowing me to see how beautiful it is."

"No not the plug my assho...BUTT PUSSY! It hurts so much."Sydney was clearly trying to reason with Nate to bad it wouldn't work.

"Sydney don't be stupid. I told you on our first day, for the rest of your life your 16 year old butt pussy will never be empty again" Nate reminded Sydney of the promise while lubing the plug.

With a lot of effort and grunting and wailing from Sydney, he managed to push the plug into her throbbing butt pussy.

After plugging her up Nate pulled off his plastic gloves and put on a new pair he then sat back down on the stool. He grabbed the 4th sound this one was almost as large as his pinky finger.

"What are you doing master?" she was clearly worried

"what do you mean Sydney?" He faked a confused tone

"Don't you have to leave? You always leave around this time."

"Oh don't worry, I told people I was going on a work trip so we can have fun all night." Nate answered calmly

"NO! NO! you can't I was good I listened please we can stop for today." Sydney was begging now full on begging

"HAHAHAHAHA do you think listening to me and being good is going to help you or make me be nicer to you? That's not how this works if you listen to me i won't punish you for disobeying but i'm still going to hurt you everyday using every hole in every way I can think of." Nate positioned the sound at the entrance to her urethra.

"THATS NOT FAIR! FUCK YOU! YOU CRUEL EVIL DISGUSTING PIECE OF SHIT BASTARD SON OF A BITCH I'M GOING TO KILL YOU AND CUT OFF YOUR DIC-AHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!"

Nate had decided to push the sound in as fast as he could this time. based on Sydney's reaction she didn't have as much fun as he did.

Nate slowly pushed it in and out beginning the slow repetitive motion that was integral to stretch her piss slit.

"It's going to be a really long night for you baby." Nate pulled out and pushed in even deeper this time.

Chapter Text

“Mom help!” Grace’s scream echoed through the house.

Nate startled, nearly jumped out of his seat with panic. Anna got up quickly and went upstairs to check on their daughter. Nate loved his wife more than anything; she was sweet and beautiful. She was a great mother and it didn’t hurt that she had the body of a super model.

He took a bite of his toast and read the newspaper, he finished his toast and reached for his cup to take a sip of coffee. The paper was boring as usual but there was one part he couldn’t help but smile at.

Police stop search for missing girl 16 year old Sydney James after no suspects for a month.

It couldn’t be going better for him, no one knew a thing. He finished his coffee and headed to the bathroom. While on the toilet he checked his phone to see if the thing he ordered had arrived. Just his luck it had, it was in the mail box a couple blocks away from the house.

He finished his morning shit and returned to the kitchen to find Anna washing some dishes.

“Is Grace okay?” Nate asked calmly while picking up a plate to help with the dishes.

“Oh of course don’t worry. It’s that time of the month and she was out of pads, but a good mother is always prepared so I had some hidden in our closet.” Anna said proudly, smiling her bright smile at Nate.

“You are such a good mom, honey.”

Anna turned towards Nate and kissed him deep and passionate. Their tongues somersaulting over each other in an act of pure passion.

“Ew. Why do you have to do that all the time?” Grace mimicked a gag

Nate released his wife and smiled at his daughter laughing.

“You won’t think it’s gross when you are in love.” Nate said

“Ya whatever dad. I gotta go or I'm gonna miss the bus.” Grace said urgently as she turned to run out the door.
“Have a great day at school, love you.” Nate yelled out

“Love you sweetie” Anna added

“Love you too and don’t worry about school. It's been a lot better for at least a month now.” Grace yelled before slamming the door.

“It’s a shame what happened to that Sydney girl but at least our daughter isn’t afraid to go to school anymore.” Anna smiled at Nate.

“I have some time before work and so do you and the house is empty.” Anna said mischievously as she began to remove her robe and head towards the bedroom.

“I’ll never say no to that.” Nate was already removing his shirt and following his wife.

Nate panted out of breath in the bed while his wife drank a bottle of water.

“That was so great honey.” Nate got out of bed and began to put on some underwear.

"I gotta go now honey can’t be late to work." Nate said cheerfully

“Oh yes, me too. Love you have a great day at work” Anna was heading to the bathroom to fix her makeup.

“Love you too.” Nate said

Nate was about to enter his car when he saw his neighbour Corey struggling to lift a couch into his house.

“Hey there, couldn't help but notice you are struggling there. Need a little help?” Nate respectfully asked.

“Well thank you very much, that help would be appreciated.” Corey smiled kindly and gestured his hands to tell Nate what side to lift.

Slowly Nate and Corey lifted the couch into the house and placed it into the living room.

“Thank you so much Nate, you really are the best of us.” Corey chortled

Corey was a middle aged man and a little overweight, he was bald with a nice beard and he was wearing a baseball cap.
Nate laughed a real genuine laugh not because of Corey’s compliment being kind but because it was so laughably incorrect. Nate did seem like a great person, no one would expect him to have a kidnapped 16 year old girl locked in a basement. They also would never guess that he was torturing that girl in the most cruel and evil ways possible. Best of all no one who saw Nate could ever imagine all the things Nate had yet to do to that poor little slut.

Nate drove until he reached the mail box he walked over and unlocked the box with number 12 on it. Inside the box was a cardboard box with multiple stickers that read fragile and don’t shake. Nate had been waiting a week for this to arrive; he had the idea after doing some research on body modifications. See Sydney expected Nate to hurt her pussy, butt pussy and pee hole but the stuff that was in this box would allow Nate to hurt a new part of Sydney a part she would never expect.

Nate entered the basement smiling holding the box, he walked over to where Sydney was tied up to the dirty mattress at the back of the basement. Sydney immediately became aware of Nate and woke up.

“Hello master.” She said respectfully

“Sydney baby, how did you sleep?”

“I slept well sir.”

“Cut the bullshit I know you're lying there’s no way you slept comfortably with that huge plug filling your butt pussy.” he said powerfully

“You are right, master it hurts a lot, I did not sleep very well.” she said

“And one plug is bad enough but you, you greedy whore have 3. One in your butt pussy, one in your pussy and one stretching that forbidden 3rd hole.”

“What hurts the most right now Sydney?”

“My butt pussy sir it hurts a lot.” Sydney answered truthfully

“Ha ya that makes sense I really hurt it yesterday.”

“But lucky for you, today we will focus on your pussy gonna make it really hurt.” Nate smiled, pulling Sydney’s legs open.

“No! I don’t want you to…please sir not today.” she asked

“You don’t want me too, who cares what you want I do whatever I want to you. You can call me sir and be kind and respectful and try to be a good slave or whatever it doesn’t change anything you will be hurt no matter what.” Nate suddenly noticed red pooling under Sydney.

“Wait Bitch are you on your period.”

“Yes I am, please give me a break today it will hurt too much sir.” she pleaded

Nate realised that Sydney and Grace were on the same schedule huh how ironic was that. While Grace had her mom to help and was given a pad and pain meds, Sydney had woken up in pain all alone.

“I bet you want your mommy right now don’t you?” he mocked

“Yes I really miss her master.”

“Do you think she would be happy to see what you have become?”

“What?”

“Do you think she would be proud to have such a slut for a daughter.”

“I’m not a slut.” Sydney defended herself

“Sure you are you have a huge gaping pussy and a butt pussy that loves to be fucked even your pee hole isn’t safe from being fucked you little slut.”

“That’s not true! It’s not my fault you did this to me! You do it! She would know that!” she cried out in anger

“Don’t pretend you hate it, you love it. You loved being strapped to the gyno chair and having your pussy and butt pussy stretched till you screamed.” Nate wanted Sydney to stop trying to please him; he wanted to see her real personality.

“FUCK YOU! I hate that stupid chair. I cry every night thinking about what will happen the next day. I hate this bullshit plug and I hate having these holes stretched! It hurts when you torture my pussy and asshole! It hurts so much! I don’t love any of this I hate it I fucking hate it and I hate you!” Sydney was yelling in absolute rage.

“Butt pussy, baby you don’t have an asshole you have a butt pussy.” Nate corrected condescendingly

“Fuck you!”

“Because of your period we will leave your pussy alone today and instead do something new.” he said

“Thank you, thank you so much.” Sydney looked happier than she had all month.

“But first your butt pussy looks thirsty so let’s give it a drink.”

Nate scrolled on his phone while Sydney sobbed next to him, her stomach was bloated like always filled with her daily enema. This was a daily occurrence and pretty mundane compared to most of the things he did but Nate still loved giving Sydney an enema. He just loved how much she hated it and he loved the way her belly jiggles when it’s full of freezing cold water.

The timer on his phone rang and Nate closed the novel before pulling it out letting Sydney expel all the water. She grunted animal like until all the water had been emptied into the bucket. Nate reinserted the large butt plug causing her to groan in discomfort. After that Nate picked up the bucket and emptied it into the sink at the back of the basement.

When Nate returned to the kneeling girl he was holding the box from the mail, he opened it up and revealed a jar of cream and multiple needles. Sydney did not like the look of the needles.

“What is that?” she asked scared

“This is going to allow for the next big change to your body.”Nate said excitedly

“What.”

Nate pulled a glove on to his hand and opened the jar to grab a small amount of cream he then began to rub it onto Sydney’s clitoris.

“What are you doing, stop!?” she exclaimed
“This cream plus these needles over time are going to cause your clit to grow.”

“That’s not possible.”

“Actually it is, I was doing some research and testosterone shots and this cream can cause a clitoris to grow multiple inches.” he said while still rubbing the cream in.

“No no no no you can't I don’t want a big clit,” she said panicked

“Well no duh obviously you don’t but I do. I want it to be big, easy to spot, easy to hurt a throbbing organ in between your legs.”

“Please don’t sir.”

“I like it when you beg it won’t change anything but I do like it.” Nate grabbed one of the needles pulled off the plastic cover and pushed it into Sydney’s clit.

“AHHHHHHH!” Sydney yelped

Nate injected the shot and then pulled out the needle.

“See already done, you don’t need to be such a baby about it.” he mocked cruelly

Alright time to actually get to business Nate grabbed Sydney by the handcuffs keeping her arms locked and pulled her towards the west wall a location in the basement he had yet to bring her too.

He stopped in front of a weird device. There was a metal post connected to the wall on the metal was a red button.

“Had this built down here before I took you but never found the right time to use it.” he said as he opened a crate to find something.

“What is it sir?”she asked

“You’ll see.” he said

Nate pulled a dildo out of the crate. It was 9 inches long and 5 cm wide. He walked over to the metal post and fastened the dildo to it. Nate then pulled Sydney into a metal contraption in front of the post. It was adjustable so you could increase the length of the dildo. The contraption forced her into a kneeling position and once her body was strapped in she could bend forwards that was all.
Nate then cranked the mechanism to make it move closer to the dildo once it was close enough that Sydney’s mouth was against the dildo, Nate squeezed her nose this forced her to open her mouth wide to take in a breath.

Nate pushed the contraption forwards forcing the dick an inch into her mouth. Sydney tried to spit it out but it was no use. She started gagging and really struggling to escape her predicament.

Nate left going over to the shelf and returned with a vibrator, he placed it directly on her clit and fastened it using tape. He then set it to maximum speed and power.

“AGH!”Sydney gagged in surprise.

“I realized I've been neglecting your cum hole and you haven’t come once since your capture a month straight of no pleasure it must have been driving you crazy.”

“Well don’t worry this should fix you right up.” Nate smiled while Sydney’s face contorted as she experienced her first orgasm panting and gagging.

“The red button there is connected to that scoreboard, once that scoreboard says 100 an alarm will ring and I will come here to turn off the vibrator.” Nate informed the squirming teen.

“The button is too far to touch with your hands. The only way to touch it is to deepthroat this bad boy all the way to the balls and press it with your nose.”

Sydney’s face dropped and her eyes showed genuine fear before clouding over thanks to the pleasure.

“That vibrator might feel good right now but after 5 non stop orgasms you’ll be wishing it would turn off. I don’t care how long it takes, the more orgasms you have the quicker the cream will work and the faster your clit will get big.” Nate joked but Sydney was not laughing.

“Have fun baby.”

30 minutes in and Sydney had not moved she was experiencing her 6th orgasm and shaking horribly. Her pussy was drenched and her legs were soaked.
“Plugh Plug Tugh Igh ogh!”She sobbed

“I already told you how to turn it off.” Nate replied lazily while reading his book.

Sydney experienced her 7th orgasm and began to truly cry, she closed her eyes and began to lean forwards she got 5 inches deep before her gag reflex made her pull back,

“Close but you gotta get it all the way to touch the button.” Nate said bored not even looking away from his book.

“Sydney groaned and Nate knew she was experiencing a cramp. Ya having a period while having to do this was pretty cruel. Nate congratulated himself for such a smart idea.

After her 10th orgasm it wasn't sounds of pleasure it was sobbing it was animal like groans it was pure torture she was in so much pain she could hardly keep her eyes open. Sydney leaned down on the dildo pushing forwards ignoring the gag reflex.

Nate noticed the way her eyes rolled into the back of her head and then the stream of puke that pooled out of her mouth covering the dildo. Sydney continued all the way all 9 inches until her nose hit the button and a large red 1 showed up on the score board.

Sydney then pulled back off the dildo all the way to the first inch.

“Congrats that’s 1. 99 to go.” Nate said

2 hours in and the score board read 40. Sydney was leaning forwards filling her cum hole with the dildo there was no more puke and instead it was this clear mucus that expelled from her mouth when she reached inch 7. Sydney pushed forwards and hit the button 41.

She was assaulted by another orgasm that made 17. They had begun to slow down thanks to the non stop pressure on her clitoris. Sydney held back a sob and leaned forwards again.

4 hours in 73 on the scoreboard, Nate returned to the basement with a sandwich he had made in the kitchen and a can of soda. He ate while opening his phone to check what had been posted on facebook.

Nate saw a post by a man named Martin James, it was a picture of Sydney in a beautiful pink dress. Her hair was done in a bun and she was smiling so pure and innocent. The caption read how to help in the search for Sydney, Nate opened the comments to see multiple people posting kind messages and wishing the husband and wife the best during this hard time.

Sydney struggled through her 22nd orgasm and leaned forwards throwing up more bile and pressing the button with her nose 76. She pulled back sobbing and screaming and crying some more. Below her a large puddle of girl squirt and period blood had mixed into a disgusting mess.

Nate sent a heart in the comments so the James would know he was thinking about their precious little girl.

5 hours in 98. She pushed forwards ignoring the orgasm rising through her body she threw up on the dildo again but when she pulled back the scoreboard said 99. She panted and pushed forwards one last time ignoring the gag reflex that hurt so badly she pushed her nose against the button 100.

The alarm rang waking Nate from his nap. He pulled the remote control out of his pocket and turned off the vibrator. Sydney finally stopped shaking and fell limp in her prison. Nate had no interest in dealing with her the way she was right now so he went over to grab the hose and sprayed her body till she was drenched and clean.

He unfastened her from the metal apparatus and carried her back to the mattress he placed her down gently. She was so weak she could hardly move. He walked over to the sink and filled her bowl with water. Immediately she began drinking quickly.

“Good drink, don’t want you dying of dehydration.” he said coldly

“Please stop, just let me go.” Her voice was sore from all the screaming or should he say creaming and her voice was scratchy from the lack of water.

“If I let you go, who would I play with?” Nate said cruelly before reattaching the chain connected to the pipe behind the mattress to her handcuffs.

“I’ll see you tomorrow and the day after that and the day after that and each day I will hurt you more and more.”

“And there is nothing you can do about it.”

Chapter Text

“Yes I love you too honey.” Nate said ending the conversation with his wife and hanging up the phone he pocketed his phone and walked downstairs into the ever familiar basement.

Nate looked over at the calendar he had taped to the wall. It was February and it had been 1 month and 2 weeks since Nate made the move that changed his life. Nate walked through the basement until he reached the west side where he had attached a brand new contraption. It was a metal chair that he had modified so he could strap Sydney to it and keep her legs pulled up in a v position.

Nate stopped to admire her, Sydney had once been a beautiful girl, a future prom queen with a bright future ahead and now she was so much better. Her hair had grown even longer flowing down her back but Nate had zero interest in the hair on her head. He had thought about shaving her bald but he wanted his slave to be pretty.

Nate’s real interest was the incredible bush he had cultivated above her teen vagina. She had gotten so hairy it was beginning to grow more to the sides, her bush had grown wild and unmanageable. Everything Nate had hoped for, Sydney had begged him to shave it a couple times now but he always gave her the same answer no the bush stays.

Sydney was strapped into the chair while a fucking machine Nate had acquired, fucked her in the pussy with a very large dildo. Every time it pushed in she gasped and grunted. The speed would slow down and then increase forcing her to endure multiple different sensations and making it impossible for her to get used to it.

Nate hadn’t thought a fucking machine would be interesting to him but after leaving her here for 2 hours he could see the appeal. It continued to fuck her, non stop in and out. The dildo was long and thick. Nate didn’t even care what it’s name was, it didn't matter all he cared about was that it stretched her even wider.

He left her to be fucked by the machine for an extra hour before turning it off and removing her from the chair. She was gagged today so Nate didn’t have to hear her annoying begging and pleading. For the last couple days Sydney wouldn’t stop asking to go home, she missed her mom and dad and blah blah blah.

Nate could care less what Sydney wanted; she just couldn’t seem to understand that.

Well Nate was going to make her realise it, he dragged her over to the center of the basement where his surprise for her was.

Sydney looked forward at the surprise and tried to run away, her breathing became erratic. Fortunately for Nate her legs were jelly after 3 hours of the machine fucking. The surprise was a dildo but not just any dildo a really long dildo it was 24 inches long but it wasn’t super thick. This dildo wasn’t meant to stretch Sydney; she had been stretched for the last 2 months and the hole was making great progress. Nate did not want to stretch her, he wanted to make her hurt. He wanted her to feel this as deep inside her as he could.

Nate walked over to the winch attached to the chain connected to the ceiling. He grabbed the chain and connected it to a harness he put onto Sydney. He buckled the harness tightly, he removed her butt plug before lifting her up. Lastly he removed the gag so she could talk.

“Don’t do this, you don’t have to do this, you can let me go and I won’t tell anyone I promise.” Sydney was really scared.

Nate ignored her desperate plea and began to lift her up until she was directly over the dildo.

“Please don’t do this I am begging you I can’t do it” Sydney was sobbing now clearly terrified of the dildo.

“It will fit, it will hurt but it will fit. Now let’s see how deep your butt pussy is.” Nate dropped Sydney down onto the dildo 5 inches went into her before she stopped.

Nate unhooked her chain from the winch now the only thing left was gravity and a very painful experience.

“Please it hurts you can’t do this I can’t do this!” Sydney screamed crying she really didn’t want to do this.

“All you have to do is relax and gravity will do the rest. Let it slide into you all the way all 24 inches.” Nate said unhelpfully

“But it’s going to hurt.”

“Duh, that's the only reason we are doing this.”

20 minutes passed with hardly any progress. 8 inches were in Sydney but she couldn’t get any farther down.

“I can’t get anymore in something is stopping me, it won't work.” she said

“That’s normal, just wiggle around and let the dildo bend. It's not sliding up your rectum anymore, it's sliding through your guts up your intestines.” he said

“I hate you.” she said sadly

“I know, now wiggle.”

Sydney began to wiggle on the dildo suddenly she felt something change and the dildo began to go in deeper.

15 inches almost there but Sydney had stopped wiggling she was hysterically sobbing now the pain was clearly far too much for her to deal with. Nate smiled at her to let her know that she could cry all she wanted; it didn't matter she was going to take the entire dildo.

Sydney began to struggle even harder forcefully pushing the dildo up her guts. She was at 21 inches but couldn’t do anymore.

“It hurts…it hurts worse than anything else you’ve done.” she cried

“You are such a baby your butt pussy is meant for this it loves this it wants to be full 24 inches up your guts its gonna happen. Now keep going.”

Sydney began to wiggle even harder ignoring the cramps and spasms and pain she twisted her body until finally she hit the bottom of the floor all 24 inches up inside her.

“UGH! OW ow ow ow ow ow ow ow ow.” Sydney was in so much pain she couldn’t even talk.

“See I told you, you could take it. It’s what your butt pussy was made for sluts like you deserve this.” Nate said

He left her sitting on the impossibly long dildo for an hour while she screamed and begged and insulted him. He didn’t care her guts were stretching to accommodate the dildo this would make it easier to fuck her deep every time. He could see it now a massive gaping bottomless butt pussy. A hole that could take even the largest sex toys. That was Sydney's future and it was glorious.

Finally he attached the chain back to the winch and lifted her slowly off the dildo she groaned and cried the whole time. Once she was free from the dildo he lowered her down onto the floor to remove the harness. After the harness was removed Nate grabbed her butt plug and forced it back in.

Nate proceeded to re-gag her and then pull her over to the gyno chair. He effortlessly strapped her limbs to it and then he opened the legs stirrups so he could have access to her holes.

Her pussy was sore from the machine fucking and her butt pussy looked like it had not enjoyed the 24 inch dildo. Unluckily for Sydney she had 3 holes, her peehole was plugged in order to continue to stretch it. It wasn’t able to take dildos yet but in a couple weeks he was sure the hole would be ready.

Nate pulled plastic gloves on and sat down on the stool, he pulled the plug out of her pee hole and watched as her pee shot out of her like a fountain. Once she was done he pushed his middle finger into her pee hole. He finger fucked her while at the same time he began to play with her clitoris.

“Stugh!” she pleaded

Nate continued his assault until Sydney began to shake and make very familiar noises before squirting from her orgasm. Nate reached over to the table and grabbed the container full of testosterone cream he applied it over her clit while continuing to stimulate her.

He finger fucked her urethra with one finger for a little longer, then he began the real challenge of today. Nate began to push a second finger in at the same time. Now she was really screaming and shaking. Nate pushed his fingers apart stretching the walls of her urethra.

“Yes, look at your pee hole stretch.” he laughed, knowing she couldn’t see a thing.

Torturing her asshole and vagina is fun and Nate loved the pain he could make her feel, but there was something special about this. The urethra was taboo no one ever expects the urethra to be used during sex that’s what makes this so great he gets to hurt a part of her she most likely had never even thought about.

Nate pushed his fingers back and forth, finger banging his captives pee hole stretching it every time he pushed in. He was making progress and he could see it.

Nate got up and left to go get some new toys. When he returned he was holding multiple pressure pumps he placed the first one over her clit and clicked to cause the suction to begin. Once it was tight he began to pump, he squeezed the pump over and over again watching her clit grow large and get pulled upwards.

“Fugh stugh fugh ou!”she said through grunts

Nate continued to pump until he thought it had gotten large enough. He removed the pump leaving her clit contained in its glass prison. He then placed a pump over he pee hole. He did the same thing as last time he pumped watched the tiny hole grow as it got sucked upwards filling the glass container.

Sydney was screaming so loud the gag was having trouble muffling it. Once it was pumped enough he removed the pump and then he placed a larger pump over her pussy. He pumped and pumped and pumped until her pussy was filling the plastic container and her lips were purple from being squeezed.

One last one he pulled her butt plug out and then immediately placed the pump over her butt pussy. He connected the pump and started to make her butt pussy look like an actual pussy. Her asshole was sucked up and since it was gaped so large the red donut inside was also sucked up. He pumped until her butt pussy looked like a flower was blooming out of butt cheeks.

“Isn’t this fun, most 16 year old girls would be at the mall on a Saturday but not you. You get to spend your Saturday having all your most sensitive and private parts pumped.

Nate left her to lie in her agony and enjoy her trapped parts while he made himself something to eat. It had been a long day and with all the fun he had forgotten to eat. Silly him.

He walked back downstairs and sat back on the stool and after a drink of his energy drink he released her from the pumps. Once all the containers were removed Nate could see the beautiful effects of the pumps. Her pussy and butt pussy were puffy and red and super sensitive. Her clit was standing erect and throbbing and her pee hole was a pink puffy slit. It was looking more and more like a pussy everyday.

He looked her in the eyes and grabbed the butt plug on the table to the side. Her eyes showed the realisation before her body did. Nate was going to reinsert the butt plug even if her butt pussy was super sore and swollen.

“NUGH! DUGH! PLUGH!”she wailed fighting to escape the binding

“I told you your hole will never be empty even if it’s been pumped and is swollen.” he said while preparing to force the butt plug back into its snug cavern. He stroked her pumped butt pussy ring and felt the electricity that travelled through her body as she shook from the sensitivity.

With a nice push he began to fill Sydney’s butt, it was harder than it had been after her enema today thanks to the pumping but despite the struggle he continued to push. The plug was a flared base plug and it wasn’t small. He pushed past the swollen puffy butt ring and concentrated all his strength into pushing the plug in.

His problem was that the plug wasn’t just thick it was long too, Nate really wanted to make sure that Sydney would never think of her sphincter as an asshole again and so he wanted to make sure that it was the hole that caused her the most pain when he wasn’t here.

Her pee hole might hurt being stretched and her pussy would be sore after a good fucking but he never tortured either of those holes as badly as he tortured the backdoor. Sydney’s poor little 16 year old asshole was no more and Nate would spend entire days only focusing on it. He would stretch, pull and force things deep into her until her crying was so bad she could barely breathe.

Originally he hadn’t intended to focus on her ass so much but while reading about her family he found out they were devout christians. That made him realise under normal circumstances Sydney would never have ever fucked her ass.

Nate knew that while everything he did broke Sydney the absolute agony and destruction her butt pussy experienced broke her in a way nothing else could because as a proper christian girl she was never supposed to have anything in that hole and now it was tortured everyday.

The thought made Nate smile just as his last push forced the butt plug back inside his toys throbbing pumped butt pussy.

Nate wasn’t doing this to avenge his daughter anymore; he knew it was more than that.

Sydney was a beautiful young girl and the best part of his day was making her cry.

Chapter Text

He paced back and forth in the driveway of the house, he stared at the message on his phone.

(Alexei) be there in 5

This is crazy, it's insane, it's the most risky thing he’s done in the last 4 months. This goes against everything he had planned. Everything he had built could fall apart today due to this stupid decision. And yet despite all these risks he knew this had to be done.

He continued to stand in the driveway, what would he do if the cops showed up, how would he get away. There would be no way to take Sydney with him, Nate couldn’t imagine not having her around it had become a daily ritual to come to this house and torture her sexually. He couldn’t lose all that, this was a dumb idea he had to leave, take Sydney and go. No, there was nowhere to go. He couldn't just walk around with a kidnapped girl until he found somewhere to stash her.

Six minutes and he still wasn’t here, he had been tricked they were coming for him. Then he heard the car heading up the driveway before it parked in front of him.

The man who exited the vehicle was handsome, he had a great jawline, a long well trimmed beard and black hair, he was muscular and had a multitude of tattoos.

“Are you the client?” he asked in a Russian accent

“Yes I am, but first I need to know that you don’t care about the legality of this and the willingness of the girl in that house.” Nate made sure to look as tough as possible while speaking.

“You pay me, I do job, that is all I care about.” he began to walk towards the house carrying his large suitcase.

Once they entered the basement Nate showed Alexei where Sydney was. She was strapped to the gyno chair where it would be easy for Alexei to do his work.

“Sydney this is Alexei he’s going to change your body some more” Nate said from the corner.

“I don’t want him to please don’t I’m fine with you I don’t want anyone else.” Sydney sounded so young when she was scared.

“He’s a master at his craft, he's going to do wonders.” Nate said

“We start with piercings tongue first then others.” he said matter of factly

Alexei pulled out a tool that looked like the tongs you’d find in a kitchen. He used the tongs to grab Sydney’s tongue and pull it out of her mouth, keeping it still. He then dipped a metal needle into some alcohol and lifted it above the circle in the tongs.

“NUH NNUH NUH!” Sydney said incoherently

Alexei lifted the needle in and then pushed it through the red fleshy organ in the girl's mouth. A little bit of blood protruded from the hole and Alexei quickly grabbed a towel to clean it.

He then grabbed a rind and inserted it into the hole, sealing it so it wouldn’t fall out.

“That is one, next you want nose piercing like bull , am I right?” Alexie asked impatiently.

“Yes, a septum ring for her nose will be perfect.” Nate answered

“Wait, stop I don’t want piercings. I already have my ears pierced, that's enough.” Sydney yelled desperately.

“She complain to much I gag her.” Alexei grabbed a ball gag and forced it into her mouth before tightening it around her head.”

He then grabbed a new needle, sterilized it and pushed it into the bridge of her nose. Just as quickly he grabbed the ring and placed it in the hole.

“Nipples now,” This wasn’t a question, it was an order.

He grabbed a needle and pushed it through her left nipple. She screamed in pain but the gag muffled it enough to not bother Alexei. He grabbed a silver ring and placed it in the hole. Alexei then grabbed the second nipple and did the same thing.

“For girls' bottom you want clitoris pierced and cunt lips is that right.” Alexei was cleaning his tools while he talked.

“Yes, that is exactly it.” Nate answered a little too excitedly.

Alexei grabbed the needle and plunged it into the side of Sydney’s clit. She was gagged but she still screached louder than Nate had ever heard.

“It’s pretty big.” Alexei noted

“Ya it sure is.” Nate answered proudly

The truth is calling it big was an understatement, the thing was massive well maybe not massive compared to a regular penis but in comparison to the clits of most girls her age there was no competition. The cream and injections had worked wonders and really made it grow. It was 3 inches long and stood tall and erect on her body. If someone saw it they would never guess it was a clit they would think Sydney was some kind of hemaphrodite.

Nate didn’t even refer to it as a clit anymore, teenage girls had clits that they could use vibrators on to make them cum. Their clits were made to give pleasure and that's what they received from it. No Sydney didn’t have a clit anymore she had a full blown girl dick, and Nate was going to make it hurt.

Alexie placed the ring at the head of Sydney’s girl dick. He then proceeded to use a hole puncher to make 6 holes 3 on each pussy lip and insert the rings. He was quick, efficient and a master at his craft.

Alexei got distracted for a second staring at what lay in between Sydney’s legs.

“I ain’t never seen a girl with too cunt holes.” Alexie remarked pointing to the second slightly smaller hole inside Sydney's pussy.

“That isn’t a second cunt hole my friend, that's her urethra better known as her pee hole.” Nate corrected

“That hole is itty bitty small man, it is not the size of vagina hole.” he fought back

“Normally it is pretty small but if you spend 4 months stretching it you’d be surprised what a girl's body can do.” Nate added

“Wow impressive but real tragedy is hole in ass I have never seen one so ruined.” Alexei sounded truly sorry for poor Sydney.

“No need to worry. Sydney doesn’t have an asshole, she has a butt pussy.” Nate said confidently.

“Butt pussy?” Alex asked confused

“Girls have assholes and they use them to shit and maybe once in a while they’ll let a guy fuck them back there. Sydney’s butt pussy has one purpose to hurt, I made it my personal goal to destroy that hole and after 4 months I’m making great progress but her butt pussy can still be hurt more and it can be stretched wider and that's what I will do.” Nate spoke proudly, happy to share his passion project.

“You are weird American man.” Alexei began to prepare his gear for the second part of the session the tattoos.

Nate had asked for a couple major tattoos: a face tattoo, a cunt tattoo, 2 tit tattoos and an asshole tattoo.

Alexei started with the face tattoo he placed the outline on her forehead where the words SLUT were spelled out in big letters.

Alexei got to work using the tattoo gun to slowly ink in the letters. Sydney was struggling really hard but the strap kept her head nice and restrained.

Nate spent most of the tattooing time watching youtube videos and eating his lunch. Every once in a while he would remove a headphone to listen to Sydney's gagged screams of pain.

It took long, a lot longer than he thought it would. Nate found that he was bored quickly normally when he was down there he was shoving something into a hole while the trembling body beneath him sobbed in anguish. Without that to do it was really boring down here.

Finally the tattooing was done and Nate could play with Sydney. He thanked Alexei for his service and paid him and then he inspected the brand new tattoos. Her forehead said slut in bold black letters, her tits had matching humanoid cows on them now with huge tits and her butt pussy ring had been tattooed bright pink.

Lastly Alexei had shaved Sydney's bush in order to tattoo her pussy, it hurt to see it go but Nate knew it was time it had grown to large and was making it harder for him to torture her pussy. It was nice while it lasted though. Alexei had done a great job with the last one he had tattooed the word pussy in bright green letters on her pubic mound. It was humiliating and that's what made it so great.

"But today isn’t over yet just because he left. I haven’t got to have my fun yet."

Nate untied her from the gyno chair and brought her into the center of the basement. Once there he connected the winch chain to her arm restraints and used it to lift Sydney up a couple inches off the ground so her feet couldn’t reach the floor. He made a mental note to come up with a better way to make her hang.
Nate then walked over to the shelf and grabbed a whip.

“Sorry I bought this when I had first got you and totally forgot to use it until now. Don’t worry I'll make sure this whip gets its time to shine.” Nate lifted the whip over his head and watched it smack Sydney's butt cheek causing her cry out in pain.

“UGGGGHHHHHH!”

Nate pulled back and hit her again this time it hit her left ass cheek

“UGGGGHHHHHH!”

Nate had never cared for whipping; he found it boring in porn and annoying in bdsm stories but actually whipping someone, he realised why it was so popular.

He hit her right ass cheek again and then her left and then her right. He smacked her cheeks again and again and again watching the red streaks stretch across the pale globes.

“AHHH!”
“AHHH!”
“AHHH!”

The more he hit her the more alive he felt it truly was an indescribable feeling. Nate whipped her butt cheeks until they were covered in scars, bruises and dried blood. Once he decided her ass had had enough he began to whip her back.

“AHHH!”

He smacked her with the whip, cracking it and watching the scars appear. He hit her back until it was as mangled as her ass cheeks. Then he whipped her back and ass a couple more times for good measure.

“AHHH!”

Once Nate was satisfied with Sydney’s back he turned her around till he was facing her. He then lifted the whip and hit her left tit with a powerful attack.

“AAAUGGGGHHHHHH!”

He whipped her breasts continuously until they were as bruised and mangled as her cheeks. He focused on hitting the nipples because that seemed to cause her the most pain. Nate next focused on her stomach whipping every last part of the exposed skin on her belly. Once he was sure her belly was crisscrossed with enough stripes of red he lifted the whip and looked for an easy target.

When he saw the red throbbing girl dick in between her legs he knew he had found it. He pulled back and let the whip sail through the air until it made contact with the sensitive organ.

“AAAUGGGGHHHHHH!”

Nate whipped her girl dick over and over again. He would occasionally miss and hit her pussy but most of the time Nate landed the attack directly on her clit. He listened for the muffled scream of pain before lifting the whip to attack her again.

“AAAUGGGGHHHHHH!”

After an hour Nate decided her body had been whipped enough she was covered in scars and whip marks. Nate didn’t think she was going to have a lot of fun sitting down tonight.

Nate was almost done for today,he went to the east side and brought over a table with a machine on it. He then grabbed the cables attached to the machine and connected them to her nipple piercings and clit piercing.

“Hope you don’t mind a little shock.” Nate joked before cranking the machine on and letting the electricity course through the metal in Sydney’s body. She began to shake and seize as she was electrocuted.

Nate turned off the electricity allowing Sydney a second to regain her bearings before he turned it back on twisting the dial. Sydney again went totally stiff as her bits were electrocuted.

Nate continued this for a good hour before he decided he was done with it and cranked the electricity down. Sydney began to breathe hard and start crying with relief, he walked over to her and removed the cables from her piercings.

He then let her down and freed her arms from their hanging prison. Still Nate wasn’t done yet he forced Sydney to the ground and pulled her legs behind her arms before locking the arm restraints in this new position.

He then flipped her over so her butt was facing the ceiling, Nate marched to the shelf and grabbed a metal dildo off of it and began connecting wires to it.Once he returned  he leaned down and pulled the butt plug out of Sydney’s ass. It was 10 inches long and when he pulled it out it dangled in the air. Nate threw it away and pushed the metal dildo into Sydney’s butt pussy.

Nate smiled at the horror written on Sydney’s face. She knew why the dildo was metal and she now knew what the wires were for.

“Let’s shock your butt pussy baby.” Nate cranked the gear and let the electricity flow through the dildo into Sydney’s backdoor.

“AAAUGGGGHHHHHHGGGHGHGHHFHGGGH!”

“Yes, scream for me baby, feel the electricity.” Nate yelled passionately

He turned off the electricity and counted to 5 and then turned it back on. He loved the way Sydney’s butt pussy was reacting to the shocks it was spasming so bad it must hurt so much. He turned off the electricity again then turned it back on. Sydney, balled her hands into fists and cried as the pain became intolerable.

Nate turned off the electricity once again giving her a 10 second break and then he turned it back on, Sydney went still again as the electricity entered her butt pussy and attacked all the precious nerve endings inside her.

After an agonizing 4 minutes Nate turned the electricity off again.

“We're gonna keep frying that butt pussy of yours until it's numb.” Nate said sadistically

Smiling at Sydney as her eyes pleaded for him to stop he turned the electricity back on.

Chapter Text

Nate lay down on his bed comfortably, Anna had already left for the morning shift which left him alone with Grace. He was reading a new book trying to finish the chapter before he got up and ready for the day.

He picked up his phone to check the time when he noticed a new post from Martin James who he, like many members of the community, was following to learn about developments in the Sydney disappearance.

The post was a picture of a 6 year old blond girl with cake on her face blowing out the candles on a large cake while multiple smiling people clapped and applauded her in the background. The caption read Happy 17th Birthday Syd we love you.

April 7th today's her birthday Nate realised excitedly. He had completely forgotten that Sydney had once been a normal girl who would have celebrated her 17th birthday with friends and family.

He pulled his blanket off revealing his nude form and put on some clothes, he walked towards the bathroom and brushed his teeth while scrolling the comments looking at all the birthday messages. People were wishing her a happy birthday and a safe return and hoping that she has a good day. 

Nate grabbed the mouthwash and swished it in his mouth, he then spat it into the sink. Sydney wasn’t going to have a great birthday, she was going to have a really painful one. He thought about what he should do today. It was her birthday so he had to make it special and unforgettable.

He shuffled through his house and said goodbye to Grace who was sitting on her bed watching a movie. She looked so happy now that Sydney was gone, every time Nate looked at her he knew he made the right decision.

He drove to the party store and parked close, he got out of the car and walked to the door. Once inside the party store he grabbed a cart and walked around until he found what he was looking for. 

He grabbed a pack of small birthday candles and he also bought a regular candle used during weddings or something. Next he went and bought a party kazoo and 1 bright pink party hat that said birthday girl. He continued browsing through the store where he bought a pre pumped balloon filled with helium, a pack of balloons and an electric pump. The last thing he did was walk over to the card section and buy a card with princesses on it. 

Once everything had been rung up he began to pay.

“Someone's birthday?” the store clerk asked 

“Ya I’m actually late.” he said while pulling out the cash he needed.

Once he paid he grabbed his bag and walked towards the exit.

“Hope it’s a great day for her.” the store clerk yelled while waving goodbye.

“It will be memorable,” he said before closing the door.

He pulled into the driveway of the house and parked his car. He then pulled the card out and grabbed a pen out of his glove compartment. He thought for a second and then started to write on the card.

Happy Birthday slut, wow 17 already i'm gonna miss referring to your pussy as a 16 year olds but I guess this is inevitable. I know you probably wish that you were anywhere else but here today surrounded by friends and family. But that's not your life anymore, this is your new normal and we're gonna celebrate this birthday the same way we spend most days. How is that you may be thinking well by torturing you of course.

He finished writing and closed the card then he dumped it in the bag with the rest of the stuff he bought and got out. He made sure to walk down the stairs slowly in order to not make too much noise and alert Sydney of his presence. He opened the door quietly and tiptoed through the basement holding the balloon in his hand and a kazoo in his mouth. 

When he approached the dirty mattress where Sydney was sleeping he blew the kazoo as loudly as he could. The sudden sound startled Sydney and she opened her eyes in fear. She looked around until she spotted Nate and then she stared at the balloon confused.

“Don’t tell me you forgot what day it is today.” Nate smiled, letting go of the balloon. He walked over to her and placed the pink birthday hat on her head.

“It’s your birthday baby.” he said as he walked towards the sink.

Nate grabbed the hose with the nozzle and walked towards Sydney.

“So let's get that butt pussy cleaned out quickly so we can celebrate.” Nate said cheerfully

She was grunting and groaning like she always did. 4L of water packed up her guts, her stomach nice and bloated. 

“We will have to make this birthday the most unforgettable one, because it's the last time you will ever celebrate it.” Nate prodded her belly while he talked.

“Birthdays are for normal girls not sluts and you Sydney aren’t a normal girl. So I'm thinking to really make this one memorable as your last ever birthday celebration. We will go full hardcore today.” Nate had begun to push down on her stomach harder than normal.

“We will focus on pain today, pussy stretching, pee hole stretching and to end the day off butt pussy stretching. I can’t think of a better way to celebrate you turning 17 than to ruin your holes a little more. “ he stopped pushing and was now just sitting staring at her.

“My daughter turns 17 next month and since she's a girl she will be getting a brand new dress, a breakfast with me and my wife and we will celebrate with all our family and friends. I will buy a big cake and she’ll be happy all day.” he began to smile just thinking about how happy Grace will be.

Nate closed the nozzle and pulled it out of Sydney and immediately watched as brown water cascaded out of her into the bucket. Once she was empty Nate picked up the butt plug and pushed it back in, a week ago getting this plug in was a struggle now it slid in easily. 

He removed her gag allowing her to talk, he preferred her gagged but he loved Sydney’s spunk he didn’t even care about her calling him sir or master anymore her attitude was intoxicating. 

As soon as the gag was out, Sydney’s cum hole erupted and she began to violently throw up onto the floor. She continued to throw up for a couple more minutes before finally ending with dry heaving. 

“UGH! Please I am fucking begging you not today it’s my birthday and i am so nauseous. Yesterday you fucked my pee hole with 3 different sounds and forced me to deep throat a 10 inch dildo on the machine!” Sydney was breathing heavily while she talked.

“Just leave me alone for today, just give me one day. All I'm asking for is one day please.” Her voice was broken and at the end of her sentence she threw up again.

Nate grabbed her by the hair and began to drag her to the gyno chair.

“We don’t have time for jokes Sydney now be a good girl and let me strap you to the mean chair so I can hurt you in new and imaginative ways.” Nate pulled her all the way to the chair while she violently struggled.

“No not again I can’t I cant. FUCK YOU! Please just stop, you've hurt me enough my holes are stretched enough just leave me alone!”Sydney was fighting every part of this.

Nate guessed that remembering her birthday had reminded Sydney of the life she once had, the life she desperately wished to return to and this chair was a reminder of her real and brutal reality. 

She could beg all she wanted Nate had no intention of ever letting her go, she was just too much fun to play with. He lifted her by the hair onto the chair and began to strap down her limbs starting with her arms and chest and then her legs. Once they were tightly in the stirrups he spread the mechanism to open them.

“Please not today, I just I don’t want to change anymore.” She was crying again.

“But baby I love the changes. Your cum hole can deep throat 10 inches and your gag reflex is almost non-existent. Your piercings and tattoos make you look so pretty and that huge throbbing girl dick is so much more fun to play with than a boring clit. But the best changes are your holes.” 

“Normally a 17 year old girl would have a tight vagina and an even tighter asshole. They may fuck with their vagina but they won’t do anything larger than a boys penis. The asshole on the other hand will never be touched and forget about the urethra; it will never be penetrated. “ he continued on his tangent.

“But you my 17 year old whore, my rape toy my captive, you are so much better because you have a huge pussy, your pee hole is this close to being able to take a dildo and your butt pussy is unrecognizable. All these changes make you perfect to me.” Nate ended his rant.

“Please no- URGGHRHRRGRH!”Sydney couldn't even finish her sentence before throwing up, vomit, landing all over her stomach and tits.

“Now let's quit the chatting and get to work. Your pussy isn’t going to stretch itself.” Nate grabbed a dildo and placed it at the entrance of her pussy, the dildo was 11 inches. He lubed it up pouring a liberal amount on the dildo.

Honestly he was pretty sure that with all the girl slick leaking out of her throbbing pussy and the piss that was constantly leaking from her stretched pee hole he didn’t even need lube. Still he wanted to make sure it slid in easily. He pushed it in and it slid all the way up over her cervix all the way to the balls.

“AH! Stop fuck off stop stop stop stop! It hurts just stop!” She screamed in anger. 

Nate didn’t stop, he continued to push the dildo in and out thrusting it with all his strength, next to him on the table 3 more dildos each thicker than the last each 11 inches. These would help stretch her so eventually he could finally shove his fist into her warm girl tunnel.

He forced the dildo in harder and pulled it out and then shoved it back in. Every time he pulled the dildo it stretched her pussy a little more. He continued the constant relenting fuck using his hand to push it in faster and faster. He used his free hand to grab a vibrator from the metal table and place it against her girl dick.

“NO! Wait, not that stop ow! It hurts ow! It hurts stop stop! FUCK YOU STOP!” Sydney began to sob from the new sensations.

Nate plunged the dildo in while using the vibrator to torment Sydney’s big girl dick. She shook and sobbed from the opposite sensations of pain and pleasure. Her eyes rolled up into her head and she gasped as she came squirt shooting out of her loose pussy.

“Ha ha you love this, it makes you so wet.” Nate pulled the dildo out and mercilessly shoved it back in. 

“Shut up! I hate this I hate you UGH! UGH UGH! UGH UGH FUCK!” Sydney went through her second orgasm and immediately threw up afterwards.

Sydney was shaking so hard her toes were curled and she was kicking up and down like a little girl. She was trying to close her legs to fight. She wanted this to end but there was nothing she could do to stop Nate.

 UGH! UGH! AAAHH! UGH UGH UGH PLEASE UGH UGH STOP UGH UGH!” Sydney came again and again. Her throbbing girl dick was so sensitive it allowed Nate to bring her to orgasm almost instantly.

Nate pushed the dildo back into Sydney’s pussy and it slid in with zero effort, perfect after 30 minutes he had stretched her enough to put dildo 1 away. He reached over to the table and grabbed dildo 2. Nate learned one thing over these last 5 months porn fiction lies. In all those stories, a rapist finds a virgin girl and only a couple hours later he's shoving his fist into her. In reality a woman's vagina could stretch but it had to be done slowly or you risk severe injury and possible infection. Nate did not want to kill her so he was doing it the right way, stretching her a little more everyday. 

Dildo 2 was thicker and went in slower, he didn’t even have to lube it since Sydney’s pussy was drenched in girl juice. He pushed the dildo in slowly letting each inch fill her, he kept pushing until all 11 inches of the dildo were inside her. Then he pulled out slightly before pushing back in. He fucked the dildo into her nice and slow, it was thick and so every time he pushed it in it stretched her slightly. 

“UGH stop. It’s my birthday please!” Sydney was gasping from the orgasms, her cum hole was drooling all over herself.

Nate removed the vibrator from her girl dick and placed it back on to the table.

“I know it’s your birthday that's why I'm doing this.” Nate continued fucking her with the dildo. 

He fucked her for an hour this dildo was thicker and so it took more time to really stretch Sydney’s tunnel so he could transition to dildo 3. Nate grabbed a towel and wiped sweat off his face, he pulled the dildo out and grabbed dildo 3. It was only a little thicker then 2 but Nate was confident Sydney would feel it.

Nate slowly pushed dildo 3 into his slaves pussy, inch by inch it was consumed. Nate fucked it back and forth slowly he didn’t want to risk ripping her. He just wanted to stretch her.

“AHHH AHHH omg stop just stop!” Sydney’s anger was more potent than it had been the last hour.

An hour later Nate finished with dildo 3 and grabbed the last dildo the thickest one yet dildo 4.

“It won't fit.” Sydney choked out between sobs

“Oh baby things way bigger than this can and will fit up your slutty girl tunnel.” Nate pushed dildo 4 in and Sydney grunted in pain. He couldn’t help smiling at her reaction to the intrusion; this dildo wasn’t anything compared to the toys he knew he could fit in her.

It took another hour of back breaking work and effort, and continuous pressure to finally finish with dildo 4. Nate pulled it out and Sydney grunted in pain but remained still. He threw it onto the table then he walked over to the shelf and grabbed a plug. He sat back down and pushed it into Sydney’s fuck hole.

“OW! OW! OW! OMG! It’s not going in!” Sydney was yelling again.

Nate kept pushing then he felt the resistance weaken and the plug slipped into her pussy sealing it.

“Look at that, it's a perfect fit, nice and snug, this plug is going to keep your hole stretched.” he laughed while saying this.

“Next up it’s pee hole stretching time.” 

“Not that not my pee hole! My pee has started leaking out of me I can’t control it anymore! I’m scared!” She was shaking

“The more we stretch your piss slit the weaker the muscles will get, you won’t be able to hold in your pee anymore but soon you’ll have a third hole that can be fucked.” Nate reached over to the table and held in his hand a speculum. It wasn’t very large yet but once it was cranked open fully that's where the fun begins.

Nate lubed the speculum up, he pulled the plug out of her pee hole and then he inserted it. He smiled at Sydney while he cranked it open extremely slowly, twisting it open a little more. Then stopping to let her get used to the new stretch before continuing again.

“AHHH! NO FUCK! That hurts to much stop, take it out take it out!” 

Nate did not take it out; he twisted it open a little larger.

“UGH!”Sydney began to kick her feet again.

He twisted it open a little more while looking at her shaking body, how lucky was he. He had a beautiful 17 year old girl tied up unable to do a thing and completely at his mercy. An innocent teenage girl whose holes he was determined to turn inside out.

He twisted it open again and again multiple twists over the next 30 minutes. Sydney screamed and swore and cried the whole entire time. He cranked the speculum open to its max diameter, and applauded himself for the effort.

“Wow look at that I can see all the way up your pee hole.” he informed her

“Did you ever imagine your pee hole would be this open, does the cold air flowing into it feel weird?” he asked sadistically

“Yes! It sucks pull it out!” she yelled in agony.

“While it’s open might as well clean you up.” he said

He grabbed a small stiff bristled brush and lifted it up for Sydney to see.

“NO! You can’t be serious! You can’t be this fucking evil!” 

“Let’s clean this hole nice and thoroughly.” he said before pouring a bottle of soap over the brush.

Then without warning Nate maneuvered the brush into the speculum and began to scrape Sydney’s pee hole. He pushes up and down scrubbing inside her letting the soap seep into her membranes. The brush went deeper with each push scraping her pee hole with the bristled brush. He scratched her raw pushing up and down sideways making sure the entire tunnel was touched by the bristles. 

He continued to push until the brush entered her bladder then he began to twist it around scraping and scrubbing her bladder.

“AGGGGGGGGGGHHHHHHHHHH! FUCK STOP! SERIOUSLY IT'S TO MUCH PULL IT OUT!” her pee hole torment had made Sydney remember how to use her voice.

“Oh ya baby scream for me, i’m gonna make this tunnel squeaky clean.” Nate pulled the brush out and then pushed it back in fucking her pee hole with it. He continued to scrub her hole for another 15 minutes before pulling the brush out, it was covered in blood and piss.

Nate grabbed the soap and squeezed it, dropping a large amount into the speculum filling her brutalised pee hole. He then shoved his finger into her. Finger fucking the soap deep into her bloody pee hole. He finger fucked her for 2 minutes then pulled out with a loud schlop!

“Peeing’s definitely gonna hurt more now but your hole is clean.” 

“Ah…ah…ah…enough for today…i can’t…not anymore…i can’t.” Sydney was panting, her eyes were blood shot.

“We can’t end yet. We left the best for last butt pussy stretching.” Nate got up to go get something.

“NO! Fuck you I hate you!” she couldn’t even come up with creative insults she was so tired.

Nate returned with a pump in his hand, the bag of balloons and the electric pump. He pulled the butt plug out and placed it on to the table.

“I know how much you love your puffy butt pussy so let's pump that bright pink ring up nice and big and sensitive before we begin.” He placed the pump over her butt pussy and began to squeeze the pump.

“FUCK! Stop with the pump just stop…why won’t you stop…” she said defeated

He pumped her ring up until it was crushed in the cylinder. He then stopped pumping and just left her like that, letting the ring get puffy and swollen. He left her for 10 minutes then he removed the pump. Once he took it off he saw how swollen the ring was. The red donut looked like a blooming flower.

“stop.”

Nate now grabbed a balloon and placed it inside her puffy butt hole, he then connected the electric pump and turned it on. The pump filled the balloon with air and it began to inflate inside of Sydney’s butt hole. As the balloon increased inside it stretched her ring.

“TURN IT OFF! FUCK!”

Nate continued to let the balloon inflate until the pressure got too strong and the balloon popped inside her hole.

“OW FUCK!” she yelled in pain

Nate didn’t even acknowledge the reaction; he just grabbed another balloon and placed it inside her pumped butt pussy. And began to fill it using the electric pump, the balloon filled again stretching her and then popped. 

He repeated this process over and over filling her till the balloon burst, every last balloon in the bag was used until he had reached the last one. He placed the balloon into her and inflated it. It grew larger, she groaned and then it popped.

Nate wasn’t done with the pump he placed it in the puffy butt pussy and turned it on, immediately air began to flow through her and into her stomach. Her stomach began to inflate getting larger and larger.

“OW STOP! I'M GONNA BURST STOP!”

He normally wouldn’t listen to her but she was telling the truth if he kept going her stomach would explode. He turned it off and then replaced her butt plug. Blocking the air from leaving keeping her inflated.

“Take the plug out please!” she begged

“Not yet.”

He left to go get the bag from party city. He placed the candles on the table and pulled out a lighter.

“I wrote you a card you can read later, but first we need to celebrate you turning 17.”

He opened the pack of small candles and pulled three out, he then inserted them through the speculum in her pee hole. Next he used the lighter to light the candles.

At first only the heat was a little uncomfortable over Sydney’s sensitive clitoris but then the wax of the candles started to melt. 

“AGHHHHH! They're hot take them out!”

Nate watched them burning while the wax dripped down Sydney's piss pipe. She was grunting and crying as more wax dripped down into her pee hole.

“I wish to torture your holes for many more months to come.” Nate blew out the candles and pulled them out of the speculum. 

Her pee hole had melted wax covering it, he walked over to the tub, grabbed the hose and aimed it at her pee hole spraying inside, cleaning out the wax.

“AHHHHHHHHHHHHH!!!”

He dropped the hose and grabbed the large wedding candle. He used the lighter to light it and then he stood up and lifted it over her boobs.

“Not there…” she gave up trying to beg and screwed her eyes closed.

Nate let the hot wax drop all over her nipples and breasts he covered both tits in wax and then started to drop the wax on her pussy he dropped it on her girl dick which got a loud scream out of Sydney and then he dropped more over her pussy he ended it by pouring wax all over her butt cheeks. 

He placed the candle down on the table and blew out the flame, Sydney was in more pain then she had ever been in her life. He reached for the butt plug and pulled it out of her butt pussy. As soon as it was out of her Sydney let out a loud fart the fart continued until her belly returned to its regular size once all the air had left her.

“Excuse me I didn’t know a teenage girl could fart like that. Actually a teenage girl can’t fart like that but a slut can.” he laughed as he closed the speculum in her pee hole and then reinserted her butt plug and pee hole plug.

He untied her from the chair and brought her back over to the mattress while he was dragging her, she threw up again. He had done his best to ignore her nausea but she had thrown up throughout their whole session that wasn’t normal unless…

He ran over to the hose after tying her to the pole behind the mattress, he turned it on and quickly sprayed her clean of the wax,vomit,squirt and blood. He then turned off the hose and ran out of the basement making sure to lock the door before speeding to his car.

Once he got to the pharmacy he hurried through the aisles until he found the right area, he grabbed a pregnancy test and quickly purchased it with cash.

“Someone hoping to be a father?” The clerk asked excitedly

Nate ignored him and exited the store.

He drove back to the house and rushed back down to the basement.

“Why are you already back?” she asked worried

Nate said nothing, he pulled the box open revealing the pregnancy test.

“No…I'm only 17. I can't you’re wrong!”

“Let's see.” Nate opened the pregnancy test and placed it under Sydney’s pee hole he pulled the plug out letting the pee flow from the throbbing stretched hole. It landed on the test filling it.

Nate waited the 3 minutes then looked at the test.

POSITIVE

“Guess who’s having a baby slut.” he pointed the test at Sydney who was barely managing to sit up on the mattress.

“NOOOOOOOOOOOOOO!”

Sydney started to cry uncontrollably, her tears streaming down her face. She looked so cute when she was crying, her baby face all puffy with red eyes.

Nate leaned down next to her and licked her face enjoying the taste of her salty tears. Sydney pulled back revolted by the sudden unwanted touch. He continued to lick her cheeks, his tongue covering her face in saliva.

 Sydney wailed even louder, then she began to swallow hard and next thing he saw she was vomiting on the ground.

Imagine all the ways to torture a pregnant slut.