Blackmailing My Moms Pt. 01

Blackmailing My Moms Part 1

By Charlie Flemming

Copyright 2021 Charlie Flemming

Author's note: All characters depicted in this work of fiction are 18 years of age or older.

Dearest Mary Davidson,

You and your wife killed your husband. Then your sister helped you cover it up. We both know this to be true. With this information, I can bring your whole family down in one police report. You have until nightfall.

I then added an attachment with one piece of incriminating evidence.

I have much more than that.

I sat at my computer and stared at what I wrote for a very long time. I thought about adding a demand of some kind but decided it's better to let it stew for a bit. Then I went downstairs, sat at the kitchen table, and watched Mary as she read a book on the couch in the living room. I wanted to see the look on her face when she got my email.

My name is Daniel, by the way.

I should probably mention that Mary is my mom. She's married to Ivy, my stepmom. And I also want to mention that my dad, that guy mom poisoned years ago, totally deserved to get killed by his own wife. He was evil. I mean, I guess I am too, but I was 20 and still a virgin, so I might have been so frustrated I was willing to go to crazy lengths to get some, especially from my mom...

Let me explain that Mom was smoking hot and Ivy was on par with her. Both had large DD, angelic faces, perfect asses, and they were both pretty fit thanks to our gym in the basement, but because of this they're legs were very toned and sexy, not to mention the rest of their bodies. The biggest difference was Mom's hair was straight and black while Ivy's was red and wavy.

Anyway, I got some food and ate slowly while I watched Mom. Eventually, there was a chime on her phone. She glanced at it and her eyes got wide. She ran out of the room and I wondered what was going on upstairs.

I couldn't bring any suspicions on me at all if I wanted any of my plans to succeed so if she had responded to me I wouldn't know until later when I could safely check my computer or phone. But I knew that Mom had contacted Ivy because she came through the door less than ten minutes later from work. I don't think Mom told her though that someone was blackmailing her, they're relationship had been very strained for many years up to that point.

...

I knew I was taking a risk but I went on a walk around our block to check my email. "I'll do as you ask." Is all it said. That was enough. I put the phone away, I knew that I could still stop everything before it even started. I just didn't have to do anything else. But this kind of power over my extremely hot MILF Mom, even if she had given birth to me, was too good to pass up. Damn the consequences I thought as I pulled out my phone and ordered a package addressed to Mom. I knew she'd be more likely to do as I asked than Ivy, which is why I started blackmailing her first.

...

Let me explain a few things. Hi, I'm Daniel, and I live with my mother, stepmother, and an older and younger sister in the middle of suburbia. It's decent enough, our neighbors mostly keep to themselves and our walls seem to be soundproof, though only from the outside inward and vice versa, the walls were paper-thin inside the house though.

Anyway, other than when my dad was alive, I didn't have a horrible upbringing or anything. Ivy was always Mom's best friend so I've known her my whole life. I guess they were more than friends actually but I didn't know anything until after Dad died and Mom and Ivy got married within a year from that. I guess I should have been suspicious right away but I was always very forgiving with my mother, even when she didn't deserve it. Finding out what I did, finding Mom and Ivy's little locker of evidence they buried out in the woods, why they kept that stuff I didn't know, but it changed my world.

Mom poisoned Dad, and it was because he was a psychopath. He was highly abusive to all of us. But he kept everything hidden from the rest of the world so it was almost impossible to speak to anyone about it. It was planned and executed by Mom and Ivy, and then they got my Aunt April, who is a cop but not a detective or anything, but her influence helped kept my dad from being autopsied and keeping the actual detectives from finding the obvious poison in his bloodstream. April was super hot as well, with large tits, which ran in the family, blonde hair, and a fit body. After all, she kept in shape because she was a police officer. I wanted to blackmail her too, but because she was a cop I was more worried about what she could or would do to catch me.

I have three other aunts, two of which were Mom's sisters, Nina and Olivia, and the other was Yuki, an Asian psychiatrist who was married to Olivia. Olivia was also a psychologist but doesn't have an M.D. like her wife. That's how they met though, studying psychology in college. I didn't see either Aunt Yuki or Aunt Olivia much as they lived on the other side of the city, while Aunt Nina was over there at least once a week. She and Mom were best friends as they were both very conservative. Olivia was super Christian too, and Mom wasn't really. They were both very sexually repressed actually. Even though Mom was married to another woman, I don't think they had sex that much. I'm not entirely sure why, two of the hottest women I knew, I mean, I would never take my hands off them, but I'm a 20-year-old virgin man, I'd fuck any woman at that point. But why settle when you can have the best?

Anyway, I also have an 18-year old sister who was still in high school, Lana, who had red hair like me and our stepmom, even though we weren't directly related it did confuse a lot of people but red hair was just common in my mom's family and I guess she also had a thing for redheads... She was mostly ditsy and innocent, at least that's how I saw her. My older sister, Juliet, was 21 and had black hair like mom. Aunt Olivia also had a daughter, Violet, who was now 18 like my younger sister, before she was divorced and was now single but didn't have any other kids.

Aunt April had three daughters, Sasha, who she had with a man before her current husband, and Sasha was of mixed race, half-African American and half-caucasian, and still completely my cousin. Her other daughters were Rita and Fiona. Rita has blonde hair like her mother and Fiona had red hair. Sasha was 20, like me, Rita was 19, and Fiona was 18. I didn't see them much either at that point. I think after April covered up my dad's murder, it put a damper on their relationship.

Anyway, a few days later my package came to a P.O. box I opened so that nothing suspicious came to the house. It was a webcam but I needed to make some modifications to it. When I was done with those, I sent it through the mail, addressed to Mom.

A couple of days later it came. My plan was about to begin.

Day 1 Sunday, March 27

I took out my burner phone and texted Mom. I was away from the house but I had seen the package on the porch when I left.

I had to think of a code name on the spot. I just picked the first name that popped into my head.

Bruce: I'm the one who emailed you. Call me Bruce. There's a package on your porch I want you to get.

Mom didn't answer for a bit. I wondered what was going through her head. Unfortunately, at that point, all I could do was wonder.

Finally, she answered.

Mary: it's a hidden camera?

I smiled. She didn't question me. She already knew I was the man blackmailing her.

Bruce: Don't think you can do anything to it. You can't trace its signal back to me and if you destroy it, I'll release the evidence I have to the police.

It was a few minutes before Mom answered again. She was probably going over what I was saying to her in her mind.

Mary: What do you want me to do with it?

Bruce: Place it somewhere in your house where it won't be found. And don't block the camera or face it toward a wall or anything like that. I want to see the full room wherever you place it. Somewhere you and your family go regularly. Once you set it up, turn it on.

I wanted to be very clear about what I wanted so Mom couldn't do something stupid like just put it in the garage where anyone rarely went outside to get in and out of the car.

A few minutes later, my phone buzzed and I saw the camera was on now. I scowled, she had set it up in my bedroom so I could see my bed in the corner, my desk and computer, my television and chair, all around my room. She had put it on top of my bookcase, which was hard to reach. Mom's face was in the shot at first but she got down from the stepladder she brought in and left. This pissed me off a lot. I mean, not like I'd get much from watching my own room...

Mom was going to have to be punished.

Bruce: What room is this? Doesn't look that interesting.

Not like I could get angry right away without inadvertently revealing something about myself. I couldn't have that.

Mary: It's my son's room. You didn't specify where I had to put it.

Bruce: I won't make that mistake again. You know this would displease me.

Mary: But I did what you asked...

Bruce: But you didn't behave. I was going to let you off easy after that but now...well. You brought this on yourself.

I had to think of something to make her do. Part of me started thinking really pervy thoughts, but I also didn't want to push Mom too hard too fast. True, I had a lot of power over her, but my mom was so sexually conservative that pushing her straight into something might literally drive her insane. I thought of something though.

Bruce: Since it's your son's room when he gets home, I want you to take him to where I can see both of you and make him get naked in front of you.

Almost immediately Mom replied.

Mary: How do you know my son isn't home?

Shit, I thought, now she'll be suspicious of me. I thought of something for now but knew I had to do something later so she wouldn't suspect me in the future.

Bruce: because you felt safe enough to hide a camera in his room. If I had to guess, I'd say you are completely alone in that house right now.

Ivy had a job in an office. Even though it was Sunday she was probably there. My sisters were probably out at the mall, but I wasn't sure what they did in their free time.

Mom took a long time before she responded. I think she had to take a minute before she decided that what I said made sense. I was back in control for the moment.

Mary: How am I supposed to convince my son to get naked for you?

Bruce: It's not for me. It's your punishment. And I don't care how you do it. You killed your husband and got away with it. I'm sure you can figure it out.

Then I told her to dispose of the phone in a way that no one would find it. I also told her that if she didn't give in to my demands when I told her to, I would be forced to release what I had to the police.

I threw the phone in a nearby trashcan and then drove my car to the movie theater. I couldn't be too suspicious now and had to waste enough time to make sure I wasn't the only one home when I got back.

...

When I got back, Ivy was sitting at the kitchen table, so I was right that watching a movie might help with that. I gulped when I saw her though, realizing this meant she could catch me in a compromising position with Mom. Though Mom was more than a bit naive, which is why I started with her: Mom was the practice before I turned my blackmailing on Ivy.

"Where the hell have you been?" Ivy asked with a cocked eyebrow. She was a beautiful woman and even in her business skirt, her body filled out every curve of her tight outfit, showing what a sexy woman she was underneath.

I didn't gawk long, "Out." I said simply as I hung up my coat and started walking to the next room.

"Well," Ivy spat back, "You've never just gone 'out' before." Her breasts heaved as I saw her start to get visibly angrier. "Were you with someone?"

"No, I just went out," I said simply and walked away from my stepmom without another word.

I knew that not going straight to my room was suspicious, so I just went there. I glanced at the camera just to make sure Mom put it somewhere that was actually out of sight. I was kinda proud of her for how well hidden it was.

I turned to leave. I didn't want to give Mom an easy way to get me there but she was already in my doorway. I gulped again. I was suddenly very nervous. It's one thing ordering your mother to do something over the phone, but to then have her actually do it in person was something else.

"What's up, Mom?" I said, friendly enough and swallowing all my nervousness. Mom and I had a much better relationship than me and Ivy and it would be suspicious if I was suddenly a nervous wreck.

"Um, well, um," Mom stammered as she stepped into the room. She was wearing one of her conservative outfits that covered up most of her skin, even more so than she did normally, probably because of what she was about to ask me to do.

Mom closed the door and locked it behind her. I feigned suspicion, "What are you doing, Mom?"

She took a deep breath before turning around to face me again, "I'm your mother, and as your mother, I wanted to make sure that you were growing up well like a big man." She cleared her throat, "I mean, like a big and strong man, I mean..." She trailed off.

"Well, I'm all grown up Mom, I'm nearly 21," I said cheerfully and ignorantly.

"Right," Mom said, then shook her head, "I mean, um, yeah, uh, you're right." She was blushing profusely, her angelic face turning a deep shade of crimson, "But, I mean, you're body, um..."

"What about my body?" I asked, totally oblivious.

Mom looked away from me, refusing to look at me, "I think, um, if you showed me your body I could see what a big man you've become." She didn't correct herself this time but she was practically shaking with nerves now.

Wow, I thought, maybe I pushed Mom too fast and too far already. But it was too late to go back on it now. "You want to see me naked?" I asked, dumbly.

Mom's nerves seemed to leave as she turned back to look at me. "Yes," she said nodding, "I just want to make sure you've grown up okay." Her demeanor had become much calmer. I guess me helping her along made it easier for her.

I cocked an eyebrow and looked at her as if the idea was clearly ludicrous, "But, you're my mom..." I stuttered.

Mom smiled her beautiful smile, "And that's why I should be the one to inspect you. I've seen you naked before. It's no big deal."

I still pretended to be suspicious, "I mean," I said, "I guess I can do that. But it's a bit weird isn't it?"

"Just do it, honey." Mom said simply like she was trying to get me to eat my lima beans.

"Okay..." I said as I slowly started taking my clothes off.

Mom fell silent as she watched me remove my shirt. I wasn't super muscular but I wasn't scrawny either. We do have a gym in the basement but I didn't use it as much as my moms did. I thought for a second I heard Mom gasp some as my bare chest came into view, but I figure I must have been imagining it. I then dropped my pants and stood there in my underwear. My boner was incredibly obvious.

Mom bit her lip and started shifting like she was turned on as her eyes were glued to the outline of my 9" cock in my pants. She licked her lips as she anticipated me revealing my cock to her. I couldn't believe this! Mom was turned on right now! This is an interesting development... I thought, in all my planning I never thought Mom would actually enjoy this. Hmm...

But I couldn't just take my cock out, especially now that I knew Mom wanted to see it. "Well, that good enough Mom?" I said, ignoring the fact that I had a super obvious erecting as I put my hands on my hips and did a pose like I was Superman, "I'm obviously an adult now." I pointed out.

Mom wasn't listening, "Why do you have an erection?" She asked and then gasped at herself as she realized what she was saying. She shut her eyes and turned her back to me again. "Sorry, I should-" She started to say but stopped herself. I'm sure she was about to excuse herself but remembered that "Bruce" had told her that I had to be totally naked in front of her.

I looked down at my hard-on as if I'd never had one before. I thought of just dismissing it but was loving how much this was all making Mom squirm, "Well," I said, "With such a beautiful woman in front of me, how do you expect me not to get a boner?"

Mom gasped and took a step toward the door before taking a step back. "You think I'm beautiful? Even in this?" She looked down at her conservative outfit.

"Absolutely, Mom. You're gorgeous!" I said like I couldn't help myself and then blushed as I looked away from her. I knew I was pushing her limits a bit, but I was also kind of embarrassed about admitting what I really thought.

"But, I'm your Mom, we can't-" Mom started to say but then she was interrupted by a knock on my door.

"Hey, Dan!" Ivy said from the hallway, "Is your mother in there?"

I glanced at Mom. She closed her mouth and eyes and it looked like she might be about to implode.

"No, she's not in here!" I said, "I'll let her know you're looking for her if I see her!"

"Huh? I thought she came upstairs but now I can't find her." Ivy said before I heard her walk away and down the stairs.

I looked back at Mom, she was looking much calmer now. When our eyes met, she said, "Take off your underwear." She ordered me.

I was taken aback by her boldness, "What? You want to see my erection?"

"Yes," Mom said, then gasped and said, "No! I mean, I don't want anything but to make sure everything is, um, in order. Um, with your body. And that includes, um, your penis." As she said this she became all sorts of flustered, her skin turning all sorts of shades of red.

I shrugged, "Okay!" I said happily. I knew I could have drawn it out but I let Mom suffer enough, and I was worried, just like I'm sure she was, that Ivy could be back with the house key to unlock my door if she wanted to. I pulled my underwear down and then stood up boldly, "What do you think?" I said as my erection flew free.

Mom was wide-eyed and open-mouthed. Also completely speechless as she stared at my throbbing dick. She started breathing heavily and her breasts heaved. I glanced at her jeans and I thought I saw a wet patch forming in her crotch but I might have just been imagining things.

"Um," Mom said after about a minute of us staring at each other, "I have to go." And with that she ran out of the room, unlocking the door as she ran.

I put my clothes on. It was time to start the next stage.