Blackmailing the Babysitter

Everyone in this story is over the age of 18!

This story involves some offensive words and non-consent. This is all just fantasy.

Thank you to Dougslair for editing.

CHAPTER 1

"Mum! Dad! Can one of you drive me to work please?!" Anna shouted up the stairs to her parents.

Walking down, her mother called out.

"I'll take you honey."

Anna was working as a babysitter for Jenna and Kyle Hendry. She has worked for them for the last 2 years as Kyle was a friend of her dads. It was a good job, however having turned 18 a week ago, Anna was planning on getting a full time, permanent job as soon as possible.

She really liked the Hendry's and babysitting for their toddler, Tommy. However, she didn't like that it was always weekend nights where she would much rather be seeing her boyfriend, Patrick.

"Thanks Mum." Anna said as they walked out of the door.

On the drive over, her mum asked, "How are you getting back?"

"Mr Hendry is going to drive me." She replied whilst texting her boyfriend.

"What are they up to tonight?" Her mum asked.

"It's their date night." Anna replied bluntly.

"I hope he's not drinking if he is going to drive you!" Her mother said, always worrying about her daughter.

"Don't worry Mum, if he is drinking, I'll get a taxi." Anna said to reassure her.

"Good." Her mum said before finally dropping her off.

When Anna knocked on the door, she was greeted by Kyle Hendry.

"Hey Anna, thanks for this!" He said with a smile.

Kyle was over 6 foot and a very good looking man, although he was as old as her dad, Anna has had a crush on him since she was young.

While Anna stepped in, Kyle couldn't help but check out Anna's hot young body. Since turning 18 he has seen her in a different light, her long, straight black hair, her beautiful green eyes and how she wears tight clothes that hug her big tits and curvy arse perfectly.

"Thank you, Kyle." Anna said walking into the living room.

"Hey Anna," Jenna Hendry said walking into the room in a long black dress, "Thanks for this. We needed a date night!" She said giving the young girl a hug.

"It's my pleasure." Anna said with a smile.

"Tommy is fed and in bed already so you shouldn't have to do much!" Jenna said whilst looking for her keys.

"No problem." Anna said.

She watched as Jenna and Kyle were leaving, waving them goodbye.

Kyle shouted, "Have a good night!"

And then she watched them drive away. Once the door was shut, Anna settled in front of the TV and started watching a movie. She had been texting her boyfriend the whole time until he eventually rang her.

"Hey babe, are you alone?" He asked.

"Yeah I am." She replied.

"Can I come round?" Patrick asked.

"No, you know I can't have my boyfriend around!" Anna said with a laugh.

"But I'm horny and we could have some fun." Patrick said.

Since turning 18, Anna gave Patrick his first blowjob and he was keen for more!

"Well, you will have to save it for when I'm free." Anna said with a grin on her face, loving how horny her boyfriend gets for her.

"That's not fair!" Patrick argued.

"Too bad, just think how good it will be next time I am sucking your dick." Anna said purposefully trying to turn him on.

"Now you're just playing with me, just think if I was there, I could be between your legs licking your pussy right now!" Patrick said.

"Mmm I would love that!" Anna moaned quietly, having Patrick had go down on her once before and absolutely loving it!

"I'm rock hard for you right now." Patrick bluntly said.

Anna knew that Tommy was asleep, so she thought she could get away with having a little fun by herself. What she didn't know was that Kyle Hendry has set up cameras in the living room to spy on her for his own pleasure when alone.

Sliding her hand down her shorts, Anna slowly rubbed her clit from outside of her thong.

"Mmmm, what would we be doing if you were here now?" Anna whispered down the phone.

"Well," Patrick said, "First you would suck my cock for a long time, until I spread your legs and lick your pussy until I make you cum hard! Then I would bend you over and fuck you!"

"Oh Patrick! Is that how you would us to lose our virginity?" Anna said with a teasing laugh, knowing that Patrick was desperate to finally have sex, but Anna wanted to do it a little more romantically.

"True, I just want to see your legs wrapped around me as my cock is in you." Patrick moaned, clearly wanking his cock.

Anna's shorts were too tight for real fun, so she stood up and closed all of the doors. Once it was safe, she pulled her shorts and thong off and sat on the sofa on her bare arse, spreading her legs slightly and being able to rub her clit better now.

"I would love to have you sit down and watch me riding your big cock." Anna whispered as her clit started to throb in her fingers.

"I'd love to grab your big tits as you bounce on my cock!" Patrick moaned.

Anna was soaking wet and easily slid a finger deep inside of her pussy and moaned to her boyfriend.

"Mmmm I'm so wet for you right now."

"Fuck, I'm so horny!" Patrick moaned as he wanked faster and faster.

The couple kept talking dirty to each other as they both got themselves off. Anna moving from fingering herself to rubbing her swollen clit.

"Oh Patrick, I'm going to cum soon." Anna moaned out as her breathing got louder and her chest was heaving.

"Cum for me, I'm going to cum thinking of cumming inside you!" Patrick moaned.

"What about covering my face and tits in your cum?" Anna asked.

"Fuuuuckkk!" Patrick moaned and Anna knew the thought had made him cum.

A few seconds later and rubbing her clit faster, Anna was cumming herself on the Hendry's sofa.

"Mmm that was good babe." Anna said as her breathing calmed down.

"I just wish I was there." Patrick said.

"Soon babe, then we can finally have sex!" Anna said.

After that they wrapped up the call, Anna put her shorts back on and just kept watching TV.

CHAPTER 2

Kyle was having dinner at an expensive restaurant with his wife, having a lovely evening but having to try and hide his hard cock. Ever since seeing Anna in her tight clothes he was horny as fuck.

When Jenna went to the bathroom, Kyle checked his phone to see what Anna was up to on the cameras. His best hope were some good angles of her bent over or her cleavage at the cameras, but what he saw was better than he could ever have thought.

He watched as the HD camera had Anna half naked on his sofa and fingering herself! He had the sound turned off so he couldn't hear anything but watching this sexy 18 year old playing with herself had Kyle more turned on than ever!

He turned the screen off, not wanting to ruin the excitement of it and saving it for when he was alone.

When Jenna returned, she said to Kyle.

"You know, when Anna gets a full time job, we will have to get a new babysitter. Or we can't go on dates like this!"

"I know, hopefully we can find a new one because I love how beautiful you are when you dress up like this for me." Kyle said smiling at his wife, the whole time thinking of what he was going to do with the video of his babysitter, a sick and twisted idea coming to his mind.

When they finished the meal, Kyle was driving them home, not being able to stop thinking of Anna and desperate to watch the rest of the video.

When they got back, Anna was on the sofa, the sofa he watched her fingering herself on. Kyle couldn't stop smiling as she said, "Hi, how was your date?"

"It was perfect! Food was amazing!" Jenna said.

"Come on then Anna, I'll drive you home." Kyle said as he watched Anna bend over to get her bag, not being able to take his eyes off of her arse.

"Thank you, Kyle!" Anna said and they both walked to his car.

Kyle watched her getting in, staring at her smooth, toned legs.

Anna was smiling to herself, happy that she got away with playing with herself and looking forward to next seeing Patrick and having some actual fun.

On the drive back, Kyle asked her, "So Anna, how is it going with your boyfriend?"

"It's great thank you, he's really lovely." Anna replied smiling.

"Good. I hope he treats you right?" Kyle asked.

"He treats me really well, a true gentleman!" Anna replied.

Kyle thought in his head, I would treat you like a dirty slut if I were him!

"Here we are." Kyle said pulling up to Anna's drive.

"Thank you, Kyle. Just call me next time you need me to babysit!" Anna said jumping out of the car.

Once the door was shut, Kyle whispered to himself, "Oh I will."

The entire drive back, Kyle was rock hard, thinking of Anna and how he could use the video to get her to do whatever he wanted. How he dreamt of her big, soft lips around his cock!

When he got back, Jenna was in their room undressed and getting ready for bed when Kyle pushed her against the wall and kissed her hard.

"What's gotten into you?" She asked between kisses.

"I know what's about to go into you." Kyle said, horny as fuck as he felt his wife's tits and arse, picturing it was Anna.

Kyle threw his wife onto the bed, turned her around so that she was on her hands and knees and with ease pushed his 8 inch cock deep inside of her.

"Fuuuckkk." Jenna moaned as Kyle wasted no time fucking his wife hard.

Closing his eyes, he pictured Anna bent over and taking his cock in her tight 18 year old pussy.

He kept fucking his wife harder and harder, pulling her hair back as she loves rough sex until he finally filled her pussy with his cum while she herself was cumming around his cock.

At the same time, Anna was in her bed, texting Patrick. In her mind she is planning on when they could lose their virginity. She wanted to be alone so there were no interruptions! Knowing she wouldn't be able to wait to much longer, ever since they started being sexual, Anna's horniness was in overdrive.

The next day, having just cleaned up one load of cum off his stomach, Kyle was lying down and already wanking his hard cock at the video he had of Anna. With the sound on loud, he listened to the young girl as she fingered her wet pussy, the sound of her pussy proving how wet she really was.

She only had one finger in her pussy so Kyle knew she would be tight as fuck. Her moans getting louder and louder as her legs were spread wide sent Kyle over the edge and watching the young girl cumming made him cum yet again.

Finally turning the video off, Kyle downloaded the saved video onto his phone and deleted it from his computer, not wanting his wife to stumble upon it. Then he set to get his plan in motion.

Driving to the shop, when he got home, Kyle unpacked the new phone he just bought for himself and sent the video of Anna to it.

The only contact he put into the phone was Anna's.

There was a small part of Kyle that felt bad for what he was going to do to Anna, but that was drowned out by his desire to fuck her like a slut. She would wear tight clothes around him and Kyle caught her staring at him often. He knew she would want it, she just needed to be pushed into it a little.

Jenna was out for the evening for work so Kyle knew this would be the best opportunity to start his game with the young girl.

He attached only a few seconds of the video to a message, enough of the video to show it was clearly her with her legs spread and moaning. Then he hit send.

CHAPTER 3

It was 7pm and Anna was lay on her bed watching TV and texting Patrick. With the money she earned from babysitting last Saturday, she was looking at hotel room's she could book for her and Patrick.

Just before hitting the button to book a room a text came through on her phone, it was from an unknown number and it said there was a video attached. She initially assumed it was some sort of scam, however she opened the message and saw a video was loading.

Once loaded, she hit the play button, what she saw made Anna sick to her stomach. Feeling herself going light as she watched herself on her phone, her legs spread wide and clear view of her fingering herself on the Hendry's sofa!

What the fuck?! Anna screamed in her bed! Her body was shaking in horror. How has someone got this video of me?! At the Hendry's, is this them?!

Anna assumed it was one of the Hendry's and she panicked that they would tell her parents what she has done! Quickly, trying to fix it she replied to the unknown number.

"I am so sorry! I had no idea you would see that! Please don't tell my parents, it won't happen again!"

There was no reply. Anna called the number 3 times but to no answer and then texted again. "Please, Kyle or Jenna of both! Please don't tell my mum and dad!"

Then finally there was a reply. "This isn't Kyle or Jenna."

What?! Who could it be? Anna was more than confused, who else could possibly have a video of her on their sofa.

"Who is this?!" She texted back.

"The Hendry's appear to have security in their house, I simply hacked it and saw what you get up to when alone." The unknown number replied.

"Please delete it!" Anna texted back, panicking more than ever now as it could be anyone!

"I will do what I want with it." The number texted back.

"Please don't do anything with it. I can pay you!" Anna replied, although she had no idea how she would pay this person.

"I don't want money." They replied. Anna hated their short texts and was now pacing through her room in a panic.

"What do you want?!" She texted back.

"There is one thing this video is missing, your tits." The unknown number said.

They want to see my tits? Anna was distraught, someone who she has no idea who wanted to see her boobs?!

"What do you mean?" Anna text back.

"Show me your tits. NOW!" The number replied.

Anna didn't know what to do, thinking this could end this nightmare, she pulled off her top and unhooked her bra and took a quick selfie of her tits, and going up to her neck and sent it to the number.

Kyle was sat at his desk, his big cock in his hand when the message came through. Gripping it harder when he finally saw the tits he has been imagining, they were better than he thought. Huge and perky! The sort of tits he would love to fuck. Then he texted her back. "Not good enough."

Anna still panicking replied. "What's not good enough?! Those are my tits!"

Kyle smiled to himself and replied. "They could be anyone's, send them again with your face in it."

What?! Anna thought to herself, I can't do that! Deciding that she needed to take a stand, Anna replied. "I can't do that, I'm sorry."

Kyle expected there to be some push back, but he was prepared. He quickly replied back. "I already have a video of you fingering yourself with your face in, what is the difference here? Or would you rather have everyone you know see this video?"

Anna couldn't believe this was happening to her, scolding herself for being so stupid. But trying to stand up for herself she replied. "You have no way of showing it to anyone I know!"

In an instant, the unknown number replied with a list of phone numbers for Anna's Mum, Dad and for Mr and Mrs Hendry. Kyle knew it was risky to put his own number on there, but he assumed she would not think it was him.

He was right! Anna nearly jumped out of her skin at seeing everyone's phone number! She definitely didn't want Kyle or Jenna to know what she got up to whilst babysitting! Before she had a chance to reply, the unknown number text her again. "So, photo?"

Knowing she would have to do this and hoping that would be the end of it, Anna held the camera up and posed with her face in and showing her tits.

"Good girl, how about a smile on the next one." Kyle replied, knowing he was pushing her, but with every photo he got more of a hold onto the girl.

Anna was distraught, but she did what he asked, faking a smile and sending another photo of her tits and face in.

Kyle didn't want to push the girl too far, so he texted her back. "Good girl. I will be in touch."

Anna read the message as tears began to stream down her face, knowing this wouldn't be the end of it.

Anna was a mess for the rest of the day, every time her phone buzzed, she panicked that it was the unknown number again that was blackmailing her! But it was always someone different, she couldn't even bring herself to reply to Patrick for the rest of the day.

CHAPTER 4

Anna couldn't sleep last night, worrying about everyone she knows seeing the videos and photos of her. She nearly had a heart attack when her phone started ringing. Looking at it, she saw it was Kyle Hendry. Trying to calm herself down she answered the phone. "Hi Kyle."

"Hi Anna, sorry for being so short notice but could you babysit tonight?"

Anna wracked her brain for a reason not to go, worrying that whoever was texting her would be able to see her on wherever the camera is that caught her. But she couldn't think fast enough, quickly Kyle said again. "Anna? Can you hear me?"

Stuttering she replied. "Er yeah sure, what time?"

Kyle smiled to himself, he knew that Jenna was out for the night and he had no plans originally, but he had booked himself in a hotel down the road where he can control Anna from the videos and photos from the hidden camera.

"6pm?" Kyle asked.

"Yeah that's fine." Anna replied bluntly.

"Thank you Anna, you're an angel!" Kyle said and then hung up the phone.

Anna fell onto her bed, stressing over what this blackmailer will want from her.

After her mum dropped her off at the Hendry's, Jenna was already out and Kyle was just leaving.

"You seem quiet?" Kyle asked Anna, although he knew why.

"Sorry, I'm just distracted." Anna said walking through the house.

"Oh, anything I can help with?" Kyle asked.

"No, sorry." Anna said.

Shortly after, Kyle left and Anna was in the house. Tommy was asleep in bed and Anna was doing her best to not go into the living room. However, there wasn't much else to do, so she eventually sat in there and turned the TV on. The whole time she was looking around the room to see if there were any cameras.

By 8pm, Anna had managed to forget about the cameras and was distracted by the TV, until her phone buzzed. Picking it up she saw it was from the unknown number. It said. "Hi slut, you look hot."

Who the fuck is he calling a slut?! Anna screamed in her head, looking around the room she had no idea where the camera was. All the while, Kyle was in his hotel room on his laptop watching the young girl panicking.

Texting back, Anna said. "Please leave me alone!"

Kyle replied. "I don't think so slut. You are going to do everything I say unless you want your video to get out to the world."

Anna's hands were shaking when she saw the text, knowing she had no control in this situation.

"What do you want?" She eventually texted him back.

"Good slut, are you ready to do as you're told?" He replied.

"Please can you stop calling me a slut?" Anna text back.

"But you are a slut, my slut!" Kyle replied.

Anna hated being called a slut, she was a good girl. However, she replied. "Okay."

"Good slut. Now take your top off." The unknown person texted.

Anna felt sick to her stomach, knowing this random person was watching her. With her hands shaking, she pulled her black t-shirt over her head. Then her phone buzzed again.

"Now the bra."

Without arguing anymore, Anna undid her bra and let it fall to the ground. Her perky tits now free in the air.

"Good slut. Now play with your tits." The number text her.

Anna was furious, but not wanting to annoy her blackmailer, she started to grab her big tits and play around with them in her hands.

Kyle was watching through the camera and slowly wanking his big cock whilst watching his babysitter play with her tits.