Blackmailing My Moms Pt. 05

Blackmailing my Moms: Part 5

By Charlie Flemming

Copyright 2021 Charlie Flemming

Day 22 Sunday, April 17

I was being shaken awake roughly. I knew I was going to have to punish Ivy but when I opened my eyes I saw that it was still dark and the person shaking me awake was my sister Juliet.

I felt my dick come to life as I saw that she was just wearing what she wore most nights to be but up close it was really sexy. It was one of those long t-shirts and it hugged her breasts and body because it was slightly too small. It also didn't go that far down her body so I could see her pair of pink panties visible just beneath her shirt's hem.

"Ugh, what time is it?" I glanced at my clock out was only a few hours since I went to sleep.

"I couldn't sleep," Juliet said, she glanced at the tent in my blanket that my erection was making then looked back at my face, "not after what I saw you and Ivy doing..."

Oh, fucking shit! I thought as I realized I was royally screwed, fucking Ivy, that dumb bitch! She didn't lock the door when she came in! Still, I didn't know everything Julie saw, maybe I could pass it off as something else, "whatever you think you saw, Julie, it wasn't what it looked like."

Julie laughed, amused, "oh and you didn't just cover Ivy in cum while she jerked you off?"

I was speechless at that and Julie laughed at me again, "so," I said as my face flushed with embarrassment, "what are you going to do about it?"

"I guess that depends," Julie sat on the bed and put a hand on my leg on top of the covers but very close to my dick, "why was our stepmother doing that to you? Are you two having an affair?"

I noticed her hand was very slowly sliding up my leg. I glanced at my sister's face, mostly she looked amused by this situation. I had no idea where her head was at, "that was the first hand job I've ever had." I said, telling the truth. "I don't know why she did it." I lied.

Juliet cocked an eyebrow, "wow, my twenty-year-old brother is a virgin. How embarrassing." She moved her hand from my leg and poked me in the stomach jovially. "You have such a big cock I'm surprised women aren't pounding down your door constantly. Then again, you came in second with Ivy so maybe that's why..." she was teasing me.

And it was working, I blushed and looked away from her, "Is that why you came in here? Just to make fun of me?"

Julie looked down at the tent my cock was making then looked back at me, "No. I thought I'd talk about something." My sister put her soft hand back on my leg and started rubbing it, "I've been with my boyfriend, Adam, for a while."

"Yeah I remember," I said sarcastically, "I live here remember."

"Right, yeah," she bit her lip and looked away, "he's terrible in bed..." she said after another moment.

"Why are you telling me this?" I asked my sexy sister.

"Well, because you and he both seem to have a hair-trigger when it comes to, well, cumming." She said with a snarky smirk on her face as she looked back at me.

"Oh...Kay?" I said still not sure what she was getting at.

"I mean," Juliet went on, "he's not nearly as big as you but I thought, well, maybe if I helped you get to the root of your problem you could help me figure out how to help my boyfriend be a better lover."

I was still very confused, "what?"

Julie looked at me like I was the dumbest person in the world, "I'm saying that I want to help you learn to keep from cumming so fast." I blinked, was she saying what I think she was? "And," Julie went on, "I won't tell Mom what you and Ivy were up to last night. Call it even?"

"Umm sure," I said. I wasn't sure what she meant by helping me but she then grabbed my dick through the blanket and squeezed it. That's all she did before she let go of it and stood up. My older sister was just full of surprises.

"Good, I'm going to go to bed now, but I'll talk to you more tomorrow. Okay?"

I fell asleep considering everything that just happened.

I woke up a few more hours later to Ivy waking me up. She was in one of her silk robes. It was semitransparent, and I could just make out her shaved pussy and hard nipples underneath.

"Will that be all?" She said annoyed as soon as she saw I was awake.

"Will that be all, sir." I corrected her.

Ivy's anger increased incrementally, "you know I am never going to call you that, you little shit!"

I got out of my bed all at once. I was standing in front of her. My morning wood was sticking out of my boxers but I didn't care. "Stop disobeying me you little slut! You know what I can do to you!" My voice was angry but level. I didn't want to wake anyone else up.

She was staring hungrily at my dick, "oh yeah," she said trying to sound intimidating but the only emotion that came through her voice was lust, "are you going to punish me?"

I realized that's exactly what she wanted me to do. I was right about Ivy, she was a dominant woman, she wore the pants, so to speak, in her relationship with Mom and she was ahead manager at her office firm, she never had anyone treat her this way. I was definitely going to take full advantage of this fact.

"Take off your robe," I ordered her.

I saw a brief smile on Ivy's face before it went away and she switched to an expression that made it seem like I was forcing her to do it. Still, her robe dropped on the floor around her as she revealed her beautiful body to me.

"God you're sexy," I said to my naked stepmother without thinking before quickly adding, "too bad you're such a slut."

"Fuck you." She said but in the same tone, someone would say "thank you" which was a little weird to hear.

I dropped my boxer shorts. Now that I had my nude stepmother in front of me while I was equally nude as well, I wanted to think of a good punishment. But something in me just said "fuck it" and I closed the distance between us, grabbed her, and kissed her.

Ivy kissed me back, her tongue entering my mouth, and took hold of one of my hands and put it on one of her tits. My other hand she took to her pussy and I started playing with her clit and her tit at the same time. Ivy then grabbed my cock with one hand and my balls with the other and started jerking me off while I fingered her.

She broke the kiss but kept jerking me. "I want to taste it," she moaned lustfully as she pushed me back on the bed. She kneeled on the floor as she took my dick into her mouth. Ivy had obviously done this before as she practically inhaled half my cock until it hit the back of her throat. She started moaning as she did this and I looked and saw that while she was sucking me she was also finger fucking herself with one hand.

"I'm not going to last long," I said as I felt my balls boiling.

"I want it all," Ivy moaned as she spat my cock out for a moment, "please, feed me your cum! Feed Mommy your cum!" And then sucked my cock almost down her throat again.

That did it. I had to throw a pillow over my head as I moaned out. It was the greatest pleasure I'd ever felt up to that point. My cock exploded, stream after stream of my cock cream creamed into my stepmother's sucking mouth. And she swallowed all of it. It was like Ivy couldn't get enough of it.

As I stopped cumming, Ivy laid her head on my belly. I think she came too and she was taking a moment to catch her breath. "Jesus Christ, how can you still be hard after that?" She asked as she gripped my dick and gave it a quick jerk. It was still like steel.

"Why? Up for round two?" I said cocky as all hell.

She laughed and stood up. She grabbed her robe from the floor, "no I need to go to work... Unless that's an order?" Ivy licked her lips and looked like she wanted to be late for work after all.

"No it's alright," I said, cumming down your bitchy stepmother's throat really makes you feel compassionate for her, "but I will order that you wear something slutty to work and when you come home. No bra." I didn't have to mention no panties since she already threw them in the garbage.

She bit her lip, "yes sir. I know just the thing."

Ivy left to go get her outfit and take a shower. She didn't bother putting her robe back on when she left the room.

I was going to check her out before she left for work but I didn't get a chance to add that's when Juliet came in the room.

"Well, that was fucking hot!" She said excitedly as she came in.

"The fuck!?" I said as she surprised me, "you were peaking in the door again?"

Julie smiled cheekily, "on the windowsill..." she said. There was a small one outside our windows between our rooms but we haven't gone between them in a long time. She got a bit upset, "why are you and Ivy..." there was a noise in the hallway so she said more softly, "you know...?"

I didn't know what to say so I said nothing. It was then that Ivy tried to come into the room, "the doors locked." She said through the door. "Umm, sir." She added a moment later which made my cock twitch but also made me cringe with my sister right there.

"What the fuck," Julie mouthed the words but didn't say anything as her eyes got wide.

Well. She basically knows everything, "Julie, will open the door for you."

Julie looked shocked and betrayed but I felt she started it. Anyway, she opened the door. And Julie looked at our stepmother embarrassed but then shocked as Ivy stepped into the room.

Ivy obviously wanted to impress me. Something had changed in her demeanor completely since she gave me a blowjob... She was wearing a silk dress, it had a strap that went around her neck and over both her nipples, but it was so thin I could her areolas in their entirety, practically. The dress part covered her legs and feet completely but the top of it dipped in the back so that Ivy's entire, beautiful ass was on display.

Ivy looked very surprised at Juliet standing there and she eyed me suspiciously. "Oh, Julie, you're up early." She said as if she wasn't wearing this highly revealing dress.

"Um, yeah..." Juliet said as she glanced at me as if I could explain to her what the hell was even going on right now. I just shrugged at her with a smug look on my face.

"I'm just trying out a new look," Ivy said, looking as cool as ever as she struck a pose. She was obviously very comfortable in her body when she wanted to be.

"It's very...um..." Julie considered the outfit, "Hot!" She said, licking her lips as she considered every angle of our stepmother, "I mean it, Ivy, if I were Mom I'd make love with you every day!"

Ivy was pleased with this but then her expression soured, "Your mom and I haven't had much time for that lately." She said bitterly.

"That's too bad, well, have fun with Dan!" Julie said, giving me a devilish look as she skipped happily out of the room. Julie was confusing me. I hoped she wasn't going to tell Mom what was happening between Ivy and me.

I looked Ivy up and down, "And you're going to wear that all day?" I asked.

"Why? Does it displease you?" Ivy asked, looking like she really didn't want to displease me again.

My cock lurched, "No, it doesn't, but I don't know how everyone else is going to react. I mean, Julie is one thing. She's open-minded. But Mom and Lana are going to lose their minds when they see you in that."

Ivy took a step towards me and put her arms around my neck, "But I want to please my master." She said sexily.

"You're okay with calling me master now, too?" I asked, feeling more than a bit suspicious at Ivy's change of heart.

"Let's just say I realized something this morning," Ivy said, "if you can't beat em, join em." She then kissed me and our tongues wrestled for a bit, "You're a really good kisser too." She admitted after we finished.

"So you'll do whatever I want now?" I asked.

"I mean," Ivy scoffed as she got on her knees and moved my blanket off of me, revealing my hard cock as I never put clothes back on since she left before, "you have so much against me now, I don't have much of a choice now do I?" She looked at my dick hungrily, "Please, sir, may I suck your cock?"

I nodded and my eyes rolled into the back of my head as Ivy engulfed my dick once again. God, she was really good at sucking dick. She was like a human vacuum cleaner, gargling my precum as she bobbed obscenely on my shaft. Ivy's tongue seeming to lick and slide along every part from my cockhead to my balls. She was deepthroating me now and I could feel as my dick bent and went down her throat. God this was amazing.

I tried to hold back, draw out my pleasure, but this was too much for my virginal body. As I came I grabbed my stepmother by her hair and held my cock in her throat so that I unleashed my constant cum stream straight into he stomach.

When I finished and let her get some air, Ivy coughed and said, "Damn, I really like the taste of your cum, and I didn't get to savor it." She said a little disappointed.

"Shut up, cunt," I spat, knowing she loved the negative attention, "You'll take whatever I give you."

She stood, wiping her mouth, and asked, "Why was Julie in here? Are you trying to seduce your sister as well as your stepmom?"

I looked as angry as I could muster after such an amazing orgasm, "Don't ask questions."

Ivy bit her lip in thought but she also looked horny, "I just mean..." She said after a moment, "well, I could help you seduce her...if you want."

I cocked an eyebrow at my stepmother, surprised, "This pleases me." I told her.

She smiled cheekily as she walked out of the room. Today was going to be interesting...

I was downstairs eating breakfast and Ivy was doing work on her computer but I told her I wanted her to stand and move around so mom and Lana would get the full effect of her outfit so she started pacing about the kitchen nervously.

Mom saw her first, "What the heck are you wearing?!" She said shocked as she glanced at me, "Dan is sitting right there!"

Though nervous before Ivy was suddenly very confident in front of her wife, "so what? I'm feeling good and it's Sunday. Just thought I'd try a new look while we're staying indoors." It was as good an excuse as any I suppose.

"But it's so revealing..." Mom admitted as she looked from her wife's almost fully on display breasts to her revealed ass.

"Come on, Mary, learn to live a little!" Ivy exclaimed. Then she took a step towards her and said seductively, "besides maybe we could..."

I glared at Ivy, I did not want her fucking my mom and getting rid of her sexual frustration. Ivy needed to be kept on a leash, metaphorically but that did give me ideas for the future...

"Oh, you wouldn't understand," Ivy said dismissively as she walked away from mom to pretend she was considering things in the cupboards.

Mom glanced at me then back at Ivy. She walked out of the room.

Lana came in next, "wow, Ivy, you look..." she talked off and I noticed she was staring longingly at our stepmother's ass. I remembered she had been masturbating to Mom's maid outfit the other day so I guess it shouldn't have surprised me as much as it did.

"Oh hey Lana," Ivy smiled at her, "good morning!"

"Umm, I have to go!" Lana said almost immediately and practically sprinted out of the room. When I checked the footage later she had gone into the bathroom downstairs and furiously fingered herself. I decided Lana could be pushed harder than I thought she would.

I got a text message.

Mom: meet me in the laundry room.

I wondered what this was about as I got up, adjusted my erection so it was less noticeable. And went down to our basement. To get to the laundry room you had to go through our gym so it was a bit out of the way. What I didn't expect when I got there was Mom to be standing there folding laundry completely naked.

My mouth fell open as I once again took in Mom's beauty. She dropped the laundry and came up and hugged me. My hands naturally went to her ass which I rubbed horny as hell.

Mom ignored my hands and whispered in my ear, "that horrible blackmailer is making me do this. He said I needed to approach you naked and then get you to touch my vagina!"

I blinked. Mom was just making things up now! I wondered if this had anything to do with how Ivy teased her that morning, "Don't worry Mom," I whispered back, "I'll do whatever you need me to do in order to get you out of this." I gave her ass a comforting squeeze.

Mom looked me in the eyes, she likes ravishing, "I'm going to kiss you but only so I hold back on my moans. We can't get caught in here."

We were in the basement and through the gym where only mom and Ivy went so I knew she could yell up a storm and no one would hear, "okay." That was what I said. I mean duh right?

She kissed me as I moved one of my hands to Mom's already sopping wet pussy. As I started rubbing her clit and labia mom started moaning anyway and my tongue entered her mouth. We were kissing like maniacs as I played with her pussy and then she surprised me and fished my dick out of my pants and started jerking it with both hands.

This emboldened me to stick a finger inside my mother's slick love canal. She was so turned on as soon as I did she stopped kissing me to moan, "ooh fuck, Dan! Right there! Finger me! You're fingering me! My son is fingering me and he's making his mother cuuummmm! Ooohhh mmmmyyyyy ggooooodddd!" So much for keeping quiet.

I fingered her through her orgasm but as she settled down she moved away, "I get a bit sensitive sometimes," mom explained but she stared at my hard cock, "you haven't cum yet..."

"It's okay-" I started to say.

"No it's not okay," Mom interrupted, "you made your mother feel so good and it's only fair I do the same to my son." She seemed to get more turned on referring to us by our relationship to each other. She got on her knees in front of me and I thought maybe she was about to blow me but instead she gripped get tits and wrapped them around my cock. She smiled sexily up at me, "make love to my breasts." Mom moaned, "fuck mommy's tits." She added getting lewder than she's ever gotten around me before.

I didn't need to be told twice though. I started thrusting, mom watching and so was I as the top of my dick would disappear and reappear between her soft globes. After several minutes of this Mom started moaning, "cum for me! Cum for mommy! Give mommy a huge cum facial! Cover me! Bathe me in it! Please! I need it!" She begged.

It was too hot and with a guttural moan, my cock lurched as I sprayed Mom down with my cum. She opened her mouth and I shot a mouthful into her and just kept spewing.

"Fucking hell," Mom moaned no longer seeming to care about naughty language as she examined her cum covered tits and ran her hands through the cum on her face, "I'll never get used to how much you cum! I obviously have a very virile son!"

"You look so sexy covered in my jizz, mom," I said, my cock jumped still hard.

Mom noticed it too, "I hate to leave you this erect but I should probably use the gym shower before anyone gets suspicious. I'll let you know if I need your help again." She left the room and crossed the gym naked, leaving a small trail of my cum as she walked away. I couldn't help but stare at Mom's perfect ass as she walked away from me.

I went back upstairs unbelieving of my luck when Julie came up to me, "Hey bro," she said friendly, "want to take a trip with me?"

I said sure and we got in her car. As soon as we were on the road Julie turned to me and said, "so, tell me about you and Ivy."

I shrugged, "what's there to tell?" I said like everything was completely normal.

"Oh, what?" She said as she kept her beautiful brown eyes on me instead of the road, "and I didn't see our own stepmom sucking your dick this morning?"

"What of it?" I said looking back at her, "and watch the road, please."

She looked back to the road though we were now on the road out of town.

"What of it?!" It's not every day you see your own brother getting a blowjob from his mother!"