Cassy Gets Blackmailed

Author's Notes. This is the forth chapter in my Cassy and Bob Series, the previous chapter being Hotwife Cassy and the Costume party. Also please be forewarned there is race play in this story. If you've enjoyed my stories but don't want to read such language, message me and I can send you an edited copy.

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"Don't you want to make her happy?"

These words were spoken to him by his wife's friend, as his wife was getting gang-banged only a few feet away. It had been about a week since the party and these words still rang in Bob's ears. Even sitting on the bed having just fucked his wife, and then making her cum with their toys, those words still nagged at him.

He sat up in bed and rested against the headboard. "Cass, I think you should find a fuck buddy."

Cassy opened her eyes, and looked at her husband in confusion.

"You deserve to cum on a real dick more often. I know I've shared you a few times, and I know how much better your orgasms are with a real big dick, as opposed to the toys we use. I want to make you happy."

"Sweety, I am happy. Trust me, I love feeling your dick in me and I love how rough you are with our big toys, and I cum just as much as I want to. The times you've shared me with others are amazing, but I'd rather they be infrequent. I want those times to be special," Cassy replied; making sure to show Bob how much he meant to her, not wanting to humiliate him.

"I've seen how much you crave a good fucking and how much it turns you on to fuck other men. I've seen you relish in taking cum shots. You love getting fucked by other guys. I think this is the next progression and I think it would be hot that it's not a special event we've set up. It's hot that it could just be on a Tuesday." Bob tried to persuade her.

"Hot? You want me to be slutty for you? Let you come home from work to an empty house and a text message that I'm not coming home 'til late." Cassy teased and felt her husbands penis, which was getting hard from their conversation about her taking a more permanent lover. "Tell you what, horndog. I'll think about it; but no guarantees, and it won't be for a little while. I want you to really think about it. And I'll take the same time to find someone."

"I'll always love you, you know that, right. I just crave your happiness."

"I know," replied Cassy, as they kissed and cuddled off to sleep.

Three weeks later...

Cassy was eating lunch in the teachers' lounge, daydreaming about her husband encouraging her to take a lover. This was something she'd done every day since their bedroom conversations. Just last night, she'd teased Bob about fucking someone on a regular basis, and he had a huge orgasm to the thought.

PING!

Cassy opened her phone to look at a text from and unknown number and had to quickly hide it from any of the other teachers' eyes. On her screen was a picture of her. Cassy's hands were bound, and she was being held up in the air by the cocks that were stuffed in her pussy and asshole. Below the picture, it read:

I have proof you're a whore and can ruin your career. Meet me after school at the coffee shop down the road. I'll introduce myself

What the fuck. How did this guy have pictures from the live feed that was streaming to Bob while she was fucking Tyson. This was not good. Cassy had a good career as a teacher, and this guy was trying to fuck it up. She deleted the photo, and tried to calm her breathing. She would have to meet this person and see what they wanted.

Later at the coffee shop, Cassy stood looking around when she heard, "Hello Cassy," from behind her. Sitting at the table, was a fat, average height, sweaty looking, black guy with glasses. Someone Cassy would pass on the street and never think once about. He looked like that kind of guy you feel sad for because you know he was probably lonely.

Cassy sat down at the table and whispered, "How the fuck."

"Calm down there, Cassy. No need for such language, yet," the man replied, smiling knowing he had all the power.

"Fine," Cassy calmed. "What do you want with me?"

"Name's Sam, pleasure to finally meet you in the flesh. I like to tap into my neighbors' WiFi for fun and wouldn't you know that the day I tap into Tyson's, is the day he has a whore like yourself being broadcast back to her husband. At least, I didn't know it was your husband at the time. At the time, I was furiously jerking off to your asshole being opened up. I searched were the signal was going after the fact." Sam grinned with confidence.

"Well you got your rocks off, now delete the video and leave me be. Or keep it and keep jerking off to it, I don't care. Just leave me alone," Cassy frantically whispered.

"Except, I see this as on opportunity for me. I would never in a million years have a chance with you. People always overlook me. They just see a chubby computer guy. Well I'm taking what's mine this time. I'm sure you've had a bunch of regular lovers being a slut for your husband and all. I'm going to be your new lover. And if you make me happy, then I'll delete the video. But, you have to make me happy. Or else, I send it to all the parents and your school. Do you think the parents would appreciate a whore like yourself teaching their kids?"

Cassy sat back in frustration. She feared he was right, she didn't want to lose her job. But she also didn't want to fuck this guy. Which of the two options was worse, she thought.

"Fine. When and where," Cassy demanded.

"He's my address. You can follow me there from here." Sam texted over his information.

"But I have to get home to my husband and make dinner."

"Don't use that excuse with me. Looking at that video, I'm sure you've made hubby order dinner while you had fun with one of your partners," Sam replied confidently.

Cassy was getting a bit scared. This was not what she wanted. This was not something she'd done before. Bob was always involved, always watching, always keeping her safe. She'd hoped she could get away with doing something to this guy and not let Bob know, but she might have no choice in the matter. Maybe she could fake finding a lover like Bob wanted. But he'd want me to fuck a bigger, sexier guy. Fucking this guy instead of Bob is insulting, Cassy thought to herself.

"Okay fine, but I'm texting a friend for safety I'm giving her your address," Cassy replied, as she brought up Brandy on her phone; informing her to call the cops, if she didn't text her again in forty-five minutes.

"Thats fine. You won't be harmed, I promise," Sam grinned.

Cassy drove behind Sam, and followed him to his small, one bedroom apartment. They walked in and it was surprisingly clean for how dirty Sam looked. Sam sat down in his desk chair and commanded, "Now on your knees. You are going to take out my cock and I want you to show me how much you enjoy sucking cock. If I think you're phoning in your performance, well then I send the emails and ruin your career."

Cassy begrudgingly got on her knees in front of Sam and reached for his sweatpants. Getting close to him, she could smell that he didn't shower as often as he should. It was a weird mixture of weird musk and food from the stains on his clothes. She pulled down his pants a little, expecting his dick top pop out; but was instead, greeted with the base of his shaft. She continued to pull down his pants until they were at his knees, and the head of his dick was finally able to spring free. Cassy looked on in awe at the size of the big black dick in front of her.

"Girls never want to talk to me to get at the prize in my pants. Now show me how slutty you are," Sam demanded.

Cassy could feel her body betraying her, with this giant dick in her hands. She was getting wet from the sight, and if she was honest with herself, she was getting wet with how dominating Sam was being. She opened her mouth wide and took the head of his dick into her mouth, conflicted in wanting to get this over with, and wanting to have fun.

She worked her tongue around the head and almost had to pull away. His dick was salty and bitter, and gross to taste. When the fuck was the last time this fat ass showered? Cassy asked herself. But she continued on, sluts don't care about how the dick tastes. She continued to lick and tease the head, as she wrapped her hands around the base. Her fingers just barely met, he was so thick.

"I've seen whores like you go deeper. Force it in there. I want to feel the entrance to your throat. More spit. Mmmmmm, it's nice not having to pay a slut for one of these," Sam called out.

Cassy feeling hurt and competitive, started to force her mouth further and further down his cock. She made sure to do everything she could to generate as much spit as possible. She got a comfortable rhythm moving her mouth up and down the end of the giant black cock. She became determined to show she was better than some paid sex worker.

"Mmmm, that's better. I like seeing all that spit drip down on your blouse. What do you think your students would say if they saw you like this?"

Cassy didn't answer, her mouth was full of cock. She was forcing it in with such great force, she was worried her teeth were going to get Sam mad. She worked his shaft seriously, while using it for leverage to pull her head further down Sam's rod. God I hope he cums soon, Cassy thought to herself, not sure if she was excited to receive this man's seed, or if she wanted to get out of here as soon as possible.

Cassy instinctively removed a hand from his shaft and brought it under her skirt. She started to play with her clit as she sucked on Sam's cock, something that did not go unnoticed.

"Yes, slave, play with yourself while you suck me. You do such a good job, I may cum soon."

Hearing this, Cassy increased her pace. Moving quicker, generating more spit, playing with herself more deeply, wanting to here him moan, wanting his cum, wanting to show him how good of a slut she is. "Uhhhhhh," was all Sam said, as Cassy was flooded with a torrent of cum. Cassy tried to swallow as much as she could, but the surprise caused her to pull away, and she got the last third of cum on her chin and shirt.

Cassy sat back, panting. So much spit and cum covered her chest, you could start to see the pink bra under her blouse. Cassy finally noticed the pain in her knees after the long blowjob and got up and finished catching her breath on the nearby sofa.

Sam finally caught his breath, "Likes, what I like, slut. Slave. I like slave better. Now get the fuck out and go home to your husband. I'll call you again for more fun, but don't tell Bobby about the blackmail. He should only think I'm just another one of your lovers. If he ever thinks otherwise, your life is ruined. Do you hear me?"

"Yes," Cassy replied quietly, starting to be afraid of the anger in the fat man's voice.

"Louder, and yes what, slave," Sam scolded.

Cassy had to think what would a really slutty girl say. With more volume, Cassy begrudgingly said, "Yes, Daddy."

"Good, now get the fuck out."

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Cassy sat in her car talking to herself. She was parked in her driveway, next to her husband's empty car. He was obviously inside, and she was out here, obviously covered in spit and cum from blowing another man.

"Fuck, he's going to be mad at me. But why would he be mad, he's set me up to fuck so many guys, what's one more?"

"Because he didn't set this up. It's some ugly fat fuck using you as a whore, blackmailing you. That's not what Bobby wanted. Bobby wanted me to get a fuck buddy, but I'm sure he'd have wanted me to find a stud."

"Fuck it, I have to go inside. I'll just tell him I found someone. I did what he wanted and wanted to surprise him with my current state. Yeah, that should get him going. He doesn't have to know how fucked up the situation really is."

"Bob will be happy... I hope."

With a deep breath, Cassy got out of the car. Her chest felt cold, as the air hit her cum and spit drenched blouse. She started to turn the key to her home, but Bobby ripped the door away excited and worried. Cassy was never late getting home from work.

"Honey I was so--" Bob stopped mid-sentence, as he saw his wife's disheveled state, and her nervous smile. "Upstairs, now. I want to fuck my little slut."

With that, Cassy didn't have to explain much. Bob proceeded to fuck her furiously and dump a load into her within minutes of her walking through the door. They both laid panting on the bed, Cassy a little frustrated having not cum from any of the day's activities.

"I'm going to go make a little dinner. Fuck, you're sexy when you're a slut. And I love you for finding a buddy. You can tell me more after dinner, okay?" Bob said, as he got up to wash up and take care of their mutual hunger.

Cassy stayed in bed, feeling a bit guilty, but reassured in Bob's love. She opened her nightstand to grab her magic wand. Though Bob's love was nice, Cassy still wanted to feel an orgasm. She drifted off into erotic bliss thinking about being slutty, thinking about being dominated, and worst of all, thinking about Sam's cock as she came.

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A few days later, Cassy was sitting at a cafe with her friend, Brandy, sipping on coffee. The girls wonderfully juxtaposing each other. Cassy petite and pale, clear skin; Brandy, tall, tattooed, and busty. The two of them together made a distracting sight for passersby.

"Sooo, he's got a big dick? And your husband wanted you to find a fuck buddy. I don't really see what the problem is." Brandy giggled at her friend's situation, as she sipped her coffee.

"Maybe, that I have no choice. Maybe, that he's trying to ruin me. Maybe, that he is ugly, and dominating. What will he have me do next?" Cassy countered.

"I saw a little twinkle in your eye when you said dominating. And get over yourself. Ugly people can fuck pretty good, you know. There was this one seventy year old once, thought he was going to have a heart attack. But that's not the point. Why not just have fun with it for now, and I'll try and help you figure out the blackmail part? Plus, it's just sex, right. You can have your extramarital fun and you know you'll never fall for the guy, so its a safe fun."

"I hate the fact that you make good points. I just don't want to be used," Cassy sighed.

"I think you do. Like I said, just go with it for now and I'll help you get out from under his thumb."

PING!

"Is that him?" Brandy questioned.

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Cassy stood naked in front of Sam. She'd only been in his apartment for a minute before he demanded she strip. Sam was already naked and hard, his dick rising out from between his legs and belly, thick and veiny.

"Before I give you my cock, I want you to prove to me that you want my cock. I'm going to lube up my fingers and I want you to ride them. I want you to fuck yourself on my hand. If you do a good enough job, then I'll treat you to this big cock. Do you understand, slave?"

"Yes," Cassy said, stepping toward Sam.

"Yes what, bitch?" Sam replied, pulling his hand away.

"Yes, Daddy," said Cassy, forcing herself to say it sultrily.

Sam held his hand on his armrest, his two fingers pointing up, waiting for Cassy. Cassy turned around, not wanting to face Sam. She placed her pussy at Sam's fingertips, and started to sink down on them; thankful for the lube, as his hands seemed rough and dry. She slowly rode his fingers, working herself up and down. They were fat and thick, and it felt good; they felt about the size of Bob's cock. The comparison made Cassy wet and horny, and she started to speed up.

"More." Cassy caught herself off guard, asking for another finger; but, the dominance of being made to prove her worth for Sam's cock, was turning her on.

Sam realizing what she wanted, moved two more fingers into play. He wanted her to really prove to him what a whore she was, and he wanted her to hurt herself a little, as well. To Sam's surprise, however, his four fingers easily pushed their way into Cassy's pussy. He could feel her pulse quickening on his fingers, hear her breathing excitedly pant.

"More, Daddy," Cassy asked, wanting to show Sam what a slut she was, and more importantly wanting to cum.

Is she serious? Sam asked himself. I've hit the fucking slut goldmine. Sam aimed his thumb with his fingers, as Cassy rode up and down on them. He could feel her putting her full body weight onto his hand trying to go deeper. Suddenly, Cassy grabbed his wrist off of the armrest and raised it in the air realigning everything. Cassy then came down with all her weight and pulled tightly on Sam's wrist. Sam was in a bit of shock, as he could feel Cassy's cunt lips start to slide past his knuckles, and then with a few more pushes, slide past the back of his hand. Before he knew it, his whole fist was inside this slut wife.

"Yes, that's it Daddy, I cumming on your hand." Cassy needing something big to get off on, kept forcing Sam's fist deeper and deeper into her pussy, as she rubbed her clit. She bounced energetically as she felt her orgasm rise, and then she felt her pussy clamp down on Sam's hand as she came. Her knees grew weak and she fell to the floor, the vice-like grip of her pussy pulling Sam out off his chair onto his knees.

Cassy lay ass up, her head on the floor, panting and recovering from her orgasm. Sam gently removed his hand. He admired how big a gape his fist created in Cassy. "That's a good slut, I think you've earned this." Sam lined up his cock head with Cassy's gaping pussy and started to push, not caring about Cassy's head against the hard floor. His large dick slid in easily without the need for lube, as Cassy was wet and slippery from her own horny desires.

Sam used her hole for his own pleasure. Grabbing onto her hips, he pushed her back and forth gliding himself in and out, surprised she could fit all of his dick inside her, even if she just had his fist in her. It was warm and luscious, and Sam hammered away. He didn't notice how Cassy was moaning, how Cassy was rubbing her clit; Sam didn't care if she was being slutty or not, he just cared about the feeling on his dick, and it was glorious.

He was proud of himself for lasting a good five minutes of hard pounding before he came, without any ceremony. He pulled out, just as he was about to cum, and shot his load across Cassy's ass, and all over her back and hair, and the side of her cheek. Sam marveled at the load he'd just produced, and got even more turned on, as the cum on Cassy's ass started to drip down, with a bunch of it landing in Cassy's gaping upturned pussy.

Sam tossed Cassy's shirt at her. "Clean yourself off, and clean the cum on the floor, then get out. I'll text you again when I want to give you more dick."

"Towels?" Cassy asked.

"I just tossed you a rag to clean up with," Sam replied, with a grin as he watch it dawn on Cassy she had to clean up all that cum with the shirt she would have to put on afterward. Cassy was his slut though, and she did exactly as asked.

"I'll text you again when I want that pussy. Make sure to respond quick; if you don't want your life ruined." With those words, Sam practically kicked her out the door.

Bob was excited when Cassy came home in cum-covered clothing. He was even more excited by Cassy's loose pussy. He could last longer fucking her, even if he could barely feel her walls, and he knew she could barely feel him. He was excited that she had a fun time with her fuck buddy. This is what he wanted after all. He liked his Cassy slutty.

The next evening, Cassy and Bob sat on the couch watching something, neither of them cared about. What they did care about was Cassy slowly using her hand to tease Bob's dick up and down.

PING!

Fuck that's Sam's ringtone, Cassy thought to herself. She knew she couldn't ignore it. She continued to stroke her husband as she checked her phone.