Blackmailing the Babysitter Ch. 02

Blackmailing the Babysitter 2

Everyone in this story is over the age of 18.

This involves some heavy non-consent, if that is a trigger for you I would recommend not reading on.

Thanks to Dougslair for editing!

CHAPTER 1

Anna sat on her sofa next to her boyfriend Patrick, holding his hand, her body filled with guilt. She could blame some of her cheating on being blackmailed, but she sucked four more men's cocks after her blackmailer left the glory hole and that was all her own doing.

She didn't know what came over her, having her dildo in her and being forced seemed to change who she was. It was like Anna wasn't there anymore, instead she was replaced with a slut.

"Everything okay?" Patrick asked.

"Yeah, I'm fine." Anna replied.

"Are you sure? You seem quiet." Patrick said.

Faking a smile, Anna replied.

"I'm okay, just tired."

They carried on watching the film, the whole time Anna was trying to think of how she could get out of being blackmailed.

At the same time, a few streets away, Kyle had just covered his stomach in cum from watching the video he has of Anna sucking off his friend and the delivery driver who dropped her dildo off.

I can't wait to be the first in your tight, virgin pussy. He thought to himself with a smile.

He had some guilt about what he was doing to her, but knowing he could use this hot 18 year old however he wanted outweighed the guilt.

That night, Anna lay wide awake after Patrick had gone home. Looking at her phone and reading the texts from her blackmailer, she was disgusted at what she had done, then she started to write a text out.

"Hi, can we come to an arrangement to end this blackmail please? I have a life and I can't be used like this."

Kyle jumped awake when he heard his phone vibrate.

"Who's that?" His wife Jenna groggily asked.

Kyle looked at his phone but it showed no messages, then he realised it must be his second phone that he used to stay anonymous from Anna. Opening his drawer, he pulled the second phone from its hiding spot and read the message from Anna, and deciding not to reply tonight, he put it back away and fell back to sleep.

Although Anna pretty much got no sleep, she was wide awake when her phone vibrated in the morning.

"Don't you ever ask to be freed again. You are my property now slut and you will do whatever I tell you!"

Reading it Anna could've cried, this monster clearly had no heart or intention of letting her go. As she tried to think of a reply, another text came through.

"I am fucking you soon slut."

"What the fuck?!" Anna almost shouted to herself, not believing what she just read. Quickly texting back she said, "I am not losing my virginity to someone who is blackmailing me! I have a boyfriend! Please just leave me alone! You are ruining my life!"

Kyle read the text and a little bit of his guilt returned, but he knew he had to be firm if he wanted to keep control of this young girl.

"Do not speak to me like that again! If you do not apologise in 1 minute then I am coming around to your place now and I will fuck you however I want!"

Anna almost burst in to tears reading that text, she was filled with fear knowing that this man knew where she lived and that he actually somehow had cameras in her house. Defeated, she texted back, "I am sorry, please don't do that! I will behave."

"Good girl." The blackmailer replied and then, "Get naked and send me a full photo of you, with your face in!"

Knowing that this man clearly had no problem with hurting her, Anna took a full length photo of her naked body, then, pulling her black hair back she sent the image to him.

"Good slut. You are not to wear underwear today as punishment, I want a photo of your legs spread with no underwear on every hour as proof." The blackmailer texted.

Anna thought of ways around it, Maybe I can just take off my underwear for the photos? She thought. But then she realised it would be just as easy to not wear underwear. So, she replied "Okay."

A quick reply came from her blackmailer. "You are to always address me as Daddy! If you don't again you will be punished further!"

Anna typed back in fear. "Yes daddy."

"Good slut." The blackmailer replied.

Putting her phone down, Anna looked out of the window at the rain falling to the ground. The water hitting the window matching the tears slowly pouring down her face.

At the same time, Kyle was getting dressed and getting ready to go to work, smiling to himself that he has kept Anna under control.

That day, Anna wasn't working so she stayed in the house most of the morning. Every hour on the dot she would lift up her skirt and send a photo of her bare pussy to her blackmailer. Then suddenly there was a knock on her door. Her family was out and she wasn't expecting anyone around and Anna feared it was her blackmailer.

Looking through the peep hole outside, her nerves calmed when she just saw it was Kyle Hendry. Opening the door, she faked a smile and said, "Hi Mr Hendry, sorry my dad is out."

Kyle smiled to himself, loving that this girl had no idea that he was the one blackmailing her.

"That's a shame, do you know when he will be back?" Kyle asked, although he knew that her father and his friend were at work all day. Kyle came over on his lunch with a sick idea in his mind to humiliate the girl further.

"I don't think he will be back until this evening." Anna replied.

"Damn, do you mind if I use your bathroom really quick?" Kyle asked.

"Of course." Anna said opening the door to invite Kyle in.

While Kyle was in the bathroom, he pulled out his phone. Knowing it was a risky game, but guessing that Anna would never suspect him as the blackmailer he texted her off his second phone.

When Anna's phone vibrated and she saw it was her blackmailer she felt sick. Looking at it, it read, "Hi slut. It seems you have a guest in. That is the man you babysit for, isn't it?"

Anna remembered that somehow her blackmailer had cameras in her house, quickly texting back she said, "Yes it is."

Kyle smiled at the text and replied. "Get undressed. When he comes out you are to offer yourself to him."

Anna's heart almost stopped when she read that! Her hands were shaking as she replied.

"I can't do that! He is married and friends with my dad!!"

Kyle smiled and typed back. "You will do as you're fucking told! Or he will have all of the videos and photos I have of you!!"

Anna was panicking now! She knew that the blackmailer had videos of her masturbating on Kyle's sofa when she was supposed to be babysitting his son! She texted him back. "Please, I'll do anything else just not that!"

Flushing the toilet to make her panic more, Kyle sent one more text. "Do it now or everyone will know what a slut you are and your boyfriend will see you sucking a big cock that isn't his! Final warning."

Anna was fucked, if those videos or photos got out then her life would be ruined! But doing this with Kyle could also ruin her! She just hoped that she could try and do it without Kyle telling anyone. When she heard the bathroom door open upstairs, Anna knew she would do as she was told.

Quickly pulling off her skirt and her top, she could hear Kyle's footsteps down the stairs. Unhooking her bra, Anna stood completely naked in her living room.

Kyle was smiling the whole walk down, being able to hear Anna rummaging around she knew she was doing as told. When he got to the bottom of the stairs and he finally got to see the sexy 18 year old completely naked in person, he had to fight away his smile and replace it with a shocked look.

"Anna! What the hell are you doing?!" He almost shouted.

Anna was in complete panic mode, her body felt like it was shaking and she could feel her perky boobs and arse giggling.

"I...I...I..." Anna stuttered out not being able to find the words.

"Why are you naked?!" Kyle asked, not moving from the bottom of the stairs.

"I... I wanted to ask you..." Anna said, again stopping at the end.

"Ask me what?" Kyle said. Inside he was jumping with joy but he was doing well at pretending to be shocked.

"I want to ask, if you wanted me?" Anna finally whispered. Shame filling her body and she could feel her cheeks burning with embarrassment.

It took everything inch of Kyles being to stop from saying yes and fucking her right there, but he was in it for the long game. Instead, he replied back.

"Anna this is very inappropriate! I am married and best friends with your dad!"

Anna was relieved that Kyle said no, but also still filled with shame.

"I'm sorry." Anna whispered, not being able to look Kyle in the eye.

Kyle was happy she couldn't look at him because he had a rock hard cock looking at the young girls tight body.

"Anna, what did you think would happen?" Kyle asked, loving pushing the girl to further humiliation.

"I... I don't know." Anna whispered back, her eyes fixed to the ground.

"I will have to tell your father about this." Kyle suddenly said.

Anna's eyes shot wide open as she looked at Kyle and shouted out. "No! Please don't! I'm sorry it won't happen again!"

Then she bent down to pick back up her clothes. Kyle loved watching her tight body moving and was disappointed when she put back on her top and skirt.

"Anna, you shouldn't have done this." Kyle said still not moving.

"I know. I'm sorry." Anna said, "Just please don't tell anyone!"

"Don't you have a boyfriend?" Kyle asked.

"Yes." Anna said hanging her head in shame once more.

"You shouldn't be doing things like this Anna. I will have to think if we can keep you as our babysitter." Kyle said, something that Anna was expecting to hear.

"I understand. I'm so sorry." Anna said with a few tears falling down her face.

"Let's just not talk about this again." Kyle said and then started to walk to the front door.

"Thank you, I am so sorry again!" Anna shouted as Kyle left the house.

FUUUUCKKKK!!!! Anna screamed in her head!!

Kyle on the other side of the door was smiling, so happy to have seen Anna completely naked.

CHAPTER 2

Anna hasn't heard anything from Kyle since she was forced to offer herself to him, thankfully it didn't seem like he told her parents. She also hadn't heard from her blackmailer for a few days which she was grateful for.

On the phone to Patrick, he suddenly asked. "So, I was looking at us booking a hotel room in a few weeks."

They have discussed this a lot, the plan to book a hotel room so that they can lose their virginity to each other. Although she has learned that her blackmailer plans to have sex with her, she was more afraid than ever.

"That's a good idea." Anna replied, trying to act like everything was okay.

"Great, should I book us somewhere for say three weeks time?" Patrick asked.

"Perfect, I can't wait." Anna replied, hoping that she will lose her virginity with Patrick before her blackmailer plans to use her again.

"Anna! Dinner is ready!" Her mother called from downstairs.

"Patrick, I have to go, I love you." She said and then put the phone down.

Sitting at the table, Anna looked around her family, all smiling and happy. Anna hasn't felt that happy since her blackmailing started.

Kyle was in his own house, having a meal with his wife thinking about Anna's naked body. He was starting to get a little more paranoid about his wife finding out after she heard his second phone vibrate the other night. He knew that if she found out then their marriage would be over, but Kyle thought it was a risk worth taking to have his fun with Anna.

The whole time Anna was sat at her table, she was looking around to see if there were any cameras in there and wondering if her blackmailer was watching her.

Both finished their meals at the same time, Anna headed to her bed and Kyle went into his home office and thought about how he can work at getting to fuck Anna.

The next day.

Anna was home alone again, flicking through her phone when she was startled to a knock on the door. Last time she was home alone and someone came in, her blackmailer forced to her get naked and she prayed that he wasn't watching again.

Heading to the door and looking through the peep hole, Anna's heart stopped. It was the delivery man that dropped off the dildo from her blackmailer.

He's not got me another toy has he?! She thought.

Hesitantly, Anna opened the door and saw that the man had nothing in his hands. Although he was dressed in a delivery man's uniform, a brown shirt and brown trousers.

"Hi there little girl." He said with a smile.

"Can I help you?" Anna asked.

The man stepped closer to the half open door and placed a hand on it, panicking Anna.

"After my last visit I have been thinking," He said with a grin, "And I want it again."

"What?" Anna replied, not believing that he thinks she will just give him a blowjob again. "No chance!" She shouted.

She tried to slam the door but his strong hand kept it open.

"Don't be like that, you seemed to enjoy yourself a lot last time." The man said.

Suddenly he pushed the door and it flew open, forcing Anna to take a few steps back as the man walked into her house.

"Please leave!" she argued.

He didn't listen, instead he closed the door and walked further into the house. Anna kept taking steps back to get away from him.

"I'm not going anywhere, you are going to do exactly what you did last time." He said.

"No!" Anna shouted, "I don't want to!" And then she tried to walk away to the living room. Standing behind the sofa, she watched as the man walked into the room.

"Listen here girl. Your blackmailer has shown me everything and he said that you have to do everything that I tell you!" He said walking closer to her.

"No! Please just leave me alone!" Anna shouted and attempted to run past the man, but he was too quick and he grabbed her and threw her onto the sofa.

Anna watched in fear as this man started to unbuckle his trousers, then he grunted. "Oh yeah, I can't wait to have those soft lips around my cock again."

"Please, please I don't want this!" Anna tried to plead.

When he pulled his trousers down, Anna saw the large cock that she once sucked. Hoping to get free while his pants were down, Anna attempted to jump up, but the large man managed to grip onto her. When Anna went so shout "No," The man took this as the opportunity to grab her head and force her open mouth onto his cock.

"Glllggg!" Anna gagged as the big cock was forced straight away deep down her throat.

Anna could taste and smell the cock that was lodged fully down her throat making her gag around it.

"Fuck yes!" The man moaned.

Without warning, he grabbed onto Anna's hair tightly and started to pull her head back and forth on his cock. Anna couldn't believe this man was forcing his cock in and out of her mouth, she could feel the tip of his dick hitting her throat as he roughly forced her deep down his cock.

"Glglg!! Gllgg!!" Anna tried to make any noise she could to get him off of her.

"That's it, moan around my cock slut!" He moaned out.

Anna knew that this man wasn't going to stop using her mouth, her only hope was that he would cum quickly and this would be over. Closing her mouth, she wrapped her soft lips around his cock as he kept forcing her head up and down of his thick shaft.

"Oh yeah! I knew you would love it!" He moaned.

Next thing, the man gripped her black hair tight and held her head still as he started to thrust in and out of her mouth. All Anna could think was that her mouth was being fucked like it was a pussy.

"Mmm such a good slut!" He moaned.

Again and again, he kept fucking her mouth, Anna had no control and she could feel her spit pouring down her chin as she gagged over and over.

Suddenly he pulled out and a load of spit fell out of Anna's mouth as she panted for air.

"Get up slut, time to fuck that tight pussy!" He ordered. This panicked Anna more than anything.

"No! Don't fuck me!" She shouted.

"You know how this is going to go! Bend over and show me that tight little pussy!" He ordered.

He pulled Anna to her feet and in a panic, she jumped back down and shouted, "Please! I'll suck your cock so good! Just don't fuck me!"

"Hmmmm." The delivery man thought, the silence was killing Anna, "Okay, if you suck my dick properly, I won't fuck your pussy today."

Anna was actually thankful that he wasn't going to fuck her. Sitting up, she looked at the man, she had tears down her face and spit down her chin as she grabbed onto his cock and said, "Okay."

Composing herself, Anna opened her mouth and once again wrapped her lips around the big cock in front of her.

She began to rub her tongue along the head of his cock as she slowly bobbed up and down on the big cock.

"There we go, that wasn't so hard, was it?" He asked.

"Mhmm." Anna moaned wanting to keep him happy and keep her pussy untouched.

Moving her head back and forth, she took more of the cock down her throat, forcing herself to gag on the cock but doing her best to please him.

"Yeesss, good slut." He moaned.

Anna could taste the man's precum on her tongue as she ran it all over his cock, bobbing up and down faster and faster hoping to make him cum. With one hand she started to wank some of the cock that she couldn't fit into her mouth.

His cock was completely covered in her spit as she bounced her mouth up and down on it.

"That's it little girl, I'm getting close!" He moaned out.

Anna was grateful that this was nearly done, thinking of what Patrick liked, Anna raised one spit filled hand and started to rub his big smooth balls as she tightly wrapped her lips around his cock and kept sucking as best she could.

"Fuuuuuckkkk!" He moaned gripping onto her head and Anna felt spurts of cum firing into her mouth and down her throat forcing her to gag.

Again, and again shots of cum would fill her mouth and Anna had no choice but to swallow it all down.

"That was fucking amazing!" The man said panting.

Anna didn't realise it, but she carried on sucking his cock until he was going soft in her mouth, getting every last drop of cum and swallowing it down.

Suddenly, the man grabbed her hair and threw her head back, "Spread your legs slut!" He ordered.

Anna panicked and shouted.

"No! You promised!!" But she was helpless against this strong man. With ease he held her back and lifted up her legs, once her skirt opened, he saw that she was wearing no underwear.

"Little whore, I bet you are happy I came!" He laughed.

"No! Please leave me alone!" Anna shouted wriggling her legs to get free.

"Shut up whore!!" He shouted and suddenly two of his thick fingers dived deep into Anna's pussy!

What she didn't realise and didn't expect, was that she was soaking wet!

His fingers easily went knuckle deep inside of her and Anna's pussy clenched around them that sent a shock of pleasure through her body.

"That's it slut!" He moaned and Anna was stunned when the man's head went lower and she felt his warm, wet tongue flick against her clit.

"Fuuuckk!" She almost screamed.

Patrick has licked her pussy once and she fucking loved it but this was something different, something better!

Although Anna tried to control herself and tell herself that she wasn't enjoying this, the man was no longer holding her down and she was allowing him to eat her pussy out.

"Mmmm such a tight, delicious pussy." He moaned between licks.

Anna was helpless to move, her legs were spread wide as he roughly fingered her wet pussy and licked her clit. When her breathing started to get heavier, she knew she couldn't fight the pleasure he was giving to her.

Rougher and rougher his fingering got inside of her, forcing his two fingers as deep as possible into her. When he forced a third finger into her Anna screamed out in pain and pleasure.