Blackmailing My Moms Pt. 06

Day 23 Monday, April 18

It was just me and Mom in the house when I woke up. Lana was in school. Julie and Ivy never came home last night.

I text Mom as the blackmailer and told her my plan for the day. It was time to start the next phase, I felt.

Mom called Aunt Yuki, who's a psychiatrist and technically has an M.D. She arrived at the house an hour later "Thank you for coming over, Yuki." Mom said to my stacked aunt, "My son needs a doctor," She explained to my Asian-American Aunt.

"Well, I am a psychiatrist but I suggest taking him to a regular doctor," Yuki told Mom.

Mom bit her lip, "It's something too sensitive to talk to someone unknown. I hope it's okay that we came to you."

Yuki smiled, "I'm happy to help. Anything for family," Even though she was only related through marriage, "What's the problem?"

Mom smiled sweetly, "It's his penis."

"His penis?" Yuki asked professionally.

"Yes, it seems that he gets frequent erections and they don't seem to go away no matter how many times he's orgasmed." It's what I told Mom to tell her as the blackmailer.

"I see, well if you want I can examine him." Yuki took me into Mom's office, she was surprised that Mom followed her in there, "Um, I can..."

"I want Mom to be here," I said, acting like I was nervous, "What if something's seriously wrong with me? I think she should be here for moral support." It was as good as an excuse as any.

Yuki looked to Mom, "Are you okay with that, Mary?"

Mom nodded. Not like she had a choice. Yuki had me sit on the couch and I removed my pants. She was surprised to see I was already hard, "I see it is a very serious condition." She said, "Um, I'll have to examine it with my hands, but I didn't bring gloves, is that okay?" She asked.

"Um, that's fine," I said.

I noticed Mom was fidgeting in her seat as Yuki gripped my cock with both hands. I knew she was getting horny watching this.

Yuki gripped me, "You are quite a bit larger than the normal man." She said, and then did something strange, she sniffed the tip of my cock, "A very masculine scent, this is a good sign." She said. "I"m going to have to, um, make you orgasm Dan, I hope that's okay? It's all part of the test."

I nodded, "It's okay Aunt Yuki." I said as if this was normal.

Yuki began to jerk me off, "You have a very big cock, Dan. Don't you think, Mary?"

"Hmm?" Mom hummed, she was obviously thinking of other things as she watched her sister-in-law jerk off her son right in front of her.

"Do you like your son's cock?" Yuki asked as she jerked me. She was being a lot naughtier than I gave her credit for, teasing my mom like that.

"Oh yes, it's delicious, I mean, delightful!" Mom corrected. But then moaned slightly as she watched as my piss-slit started to leak precum.

Yuki noticed it too, it was coming out in a steady stream and soaking her hands as she jerked me, "Cum for your aunt, Dan! Cum for me!" She moaned, obviously she was getting as turned on as MOm was.

I was on fire as I started to spew my cream all over my Asian Aunt's face. She moaned all the while looking at Mom, smiling devilishly. Mom stared back, she was beside herself with lust. She was holding back though, not touching herself or anything else but I could see a very wet spot forming in the crotch of her jeans.

"Jesus, he is still hard after that." Aunt Yuki noticed, "And with all this cum." She put a finger through the jizz on her cheek and stuck it into her mouth, "It tastes delicious though. Wow." She gripped my cock again and started jerking, "We're going to have to try to get your erection to go down though. Medically an erection shouldn't last this long after cumming."

She jerked me off again, this time she focused on Mom, "Don't you want to suck this cock, Mary? Isn't your son's dick absolutely delicious-looking? Don't you want me to suck it with my face dripping in your son's cum! Don't you-"

"Yes, you fucker!" Mom shouted as she pushed Aunt Yuki out of the way and grabbed my cock herself, "If someone's going to be giving my son orgasms around here it should be me!" She said with authority as she started jerking my dick with both hands.

Yuki smiled up at, cum leaking into her mouth as that happened, "I knew you'd see things my way." She then grabbed my mother by the back of the head and forced her mouth off my cock. Mom was sucking me off again. Aunt Yuki was a bit of a sex fiend. Who knew?

Mom was moaning like crazy around my dick as Yuki was helping her to bob on my cock like a porn star. Jesus this was hot. I could feel my balls boiling once again, "I'm going to cum again!" I announced.

"Good, fill up your mother's face!" Yumi moaned, she had her other hand in under her skirt and I knew she was finger fucking herself underneath.

I came and Mom was like a human hoover as she sucked my cream down her throat. She fell back. My dick was still hard.

"Fuck me," Yuki said as she gave my cock another squeeze, "This is insane! I've never seen a cock cum twice in a row and still be hard. I mean, I'm married to a woman so I don't see a lot of cocks, but this is still crazy!" She stood up, "Have you had sex yet, Dan?"

I blushed, "No..." I admitted.

"Well, that's exactly what I'm prescribing. Find a girlfriend and fuck her until you can't anymore. If you can't do that, well, I'll make an appointment for a week from now. Okay?"

Yuki left and Mom hid in her room for a while. I thought maybe I should talk to her again, but things were moving kind of fast. I didn't want to freak her out anymore than she could stand.

Still, there were lots to do. I gave Ivy a call.

"What?" She said into the phone after the third ring. I could tell she was still mad at me.

"Where are you? Why didn't you come home last night?" I demanded.

"None of your fucking business." Ivy snapped.

"You're with Aunt Olivia aren't you?" I said figuring it out.

Ivy was silent for a moment. "You know what I can do whatever I want with my free time. Stop acting as you own me because you really don't."

I wasn't sure why Ivy had gone back to get naturally bitchy self but she was starting to piss me off, "come home now or I'll tell Mom where you are." I ordered. "Bring Olivia if you need to." I was already doing stuff with her wife why not my blood-related Aunt as well. I hung up before she could bitch again.

Ivy was back within half an hour. The redheaded bombshell was wearing a different business skirt than the one she had on yesterday. I was still sitting in the kitchen waiting for her when she came in. Olivia was not with her unsurprisingly.

"Now what you little fucker?" She said to me. Asking for it.

I reached under her skirt and her pussy was covered in cloth! She was wearing panties! "You dumb bitch..." I said to her.

"What did you call me!?" She was angry and I think she was trying to take the power back.

I stood up, grabbed her roughly by the hair, and dragged her to the couch in the living room.

"Ow," was all my sexy stepmother said as I forced her into the next room. Now that I was being rough with her Ivy had become as docile as a kitten.

I came to the couch and forced her over my lap. I pulled her skirt up and then pulled her panties down so they fell past her dangling feet to the floor. Ivy hadn't said anything else and neither had I as I did this. I raised my hand and then took it down against her left ass cheek with a loud "THWACK!"

"Ooh," Ivy moaned and her body tensed up but she didn't struggle.

"THWACK!" My hand came down again on the right cheek.

"Oohh," she moaned softly. Ivy was getting turned on by this.

"THWACK!" Left cheek.

"You mother fucker!" She moaned out in pleasure and pain.

"THWACK!" Right.

"Mmmmm, fuck!" She was getting loud so I stopped. While my stepmother was still over my lap, her red ass staring me right in the face, I moved my hand beneath her and rubbed her pussy, "oooh," she moaned softly at the sudden contact.

"Fuck me, Ivy, you are wet as fuck right now," I said as I slipped two fingers inside her hot hole. "Don't tell me you aren't enjoying this."

"I love it!" Ivy moaned in pleasure as I fingered her. Then she remembered, "I mean I hate it! You are, ugh, so bad at, ooh, fingering my, mmm, pussy."

"Uh-huh," I muttered sarcastically as I entered a third finger into my stepmother's soaking wet cunt.

This set off her orgasm as Ivy's whole body started to shake. She leaned her face into the couch cushions to dampen get moans. God, this was fucking hot.

When she had stopped shaking, I pushed my stepmother off of me. She fell right on the ground. I offered my hand and helped her up.

"You've been a very naughty girl."

Ivy looked me in the eyes complacently, "I'm sorry master, I won't do it again." I doubted that but at least she was playing along again.

"Good," I said, playing along myself, "now get your keys and your wallet. You're going to buy a few things."

I got in her car and Ivy got in the driver's seat. I thought about letting me drive so I could make her give me road head but I didn't know where how to get where I wanted to go.

"Take us to a sex shop," I ordered her.

"Just any sex shop?" She asked, "you're assuming I know where any are."

I just cocked an eyebrow at her and Ivy just rolled her eyes back at me. "fine..." she muttered as she put the car in gear.

As we drove I considered my stepmother. She was smoking hot and I just thought about how much I wanted to fuck her. I put a hand on her leg as she drove. She ignored it like it wasn't there and I inched my hand up Ivy's thigh until I pushed her skirt up once again. She was still ignoring me so I moved my hand to her pussy. Ivy continued to act like nothing was happened as I started playing with her labia. She moaned softly as she drove.

I didn't get to play with my stepmother's pussy for long as we pulled into a parking lot for a large chain sex shop. I thought about telling her to wait so I could fingerblast get again but I decided we could probably have more fun inside the shop.

Inside, it was completely empty of people except for a sexy blonde woman with huge tits behind the counter. She had a name tag on one of her breasts reading "Donna."

The shop itself was split in half. One side had clothes that was mostly lingerie but also had done very revealing outfits. The other side was sex toys though it also inclided things like whips and handcuffs.

I put a hand on Ivy's ass and she glared at me for a moment but I only smiled like a fiend back at her. She didn't complain though and I walked it's both up to the counter.

"Hello Donna," I said to the woman who looked up from her solitaire game on the computer.

"Can I help you with anything?" She blinked when she noticed the obvious tent in my pants but she looked me in the eye after that. She probably saw a lot of dudes coming in there with erections.

I wanted to humiliate Ivy as much as possible, "My stepmother here," I said humbly as both Ivy's and Donna's eyes went wide, "keeps misbehaving and I was wondering if you had any advice to keep her in her place."

Ivy looked away from Donna but harshly whispered to me, "what the fuck is wrong with you!?"

"What the fuck is wrong with you sir." I whispered back just as harshly. She shut her mouth.

Donna sudden shock seemed to have worn off. "Umm, well, we have stuff like paddles, handcuffs, gags, blindfolds, various restraints, vibrators, anal plugs or beads, televibes..."

Donna went on listing all the things I could use to torture Ivy. I glanced at my stepmom and she was looking more and more worried but also turned on. I knew this type of physical play excited her but I wanted to do something else first.

"What about outfits?" I asked, "can you show us what you have?"

"Well I can show you where they are." Donna explained, "but I won't try any on for you. I've never worn any of this stuff."

"Why not? I'm sure it would look great on you." I said to her. This made Donna blush.

"Oh you're just going to flirt with her right in front of me?" Ivy said getting angry.

"Shut the fuck up, slut, and pick out a few outfits. Get some really sexy ones too or I'll be angry." I said to Ivy before smacking her ass as Donna smiled at this interaction. She wasn't that shocked by it which disappointed me as I wanted Ivy to be humiliated.

Instead, Ivy was obviously turned on by my mistreatment of her. She sauntered over grabbed something seemingly at random and entered one of the changing rooms.

While she was in there, Donna whispered to me, "is she really your stepmom?"

I smirked at her with a shit eating grin, "yes, does that upset you?"

Donna shrugged, "I've seen all types of couples in here so almost nothing surprises me. I guess nothing incestuous before..." she trailed off, daydreaming.

This young blonde was interesting... "what if I told you she was my real mother. I just told her she was my stepmother so you didn't freak out."

Donna looked a bit turned on, "that would be so fucking hot." She whispered, "is she?"

"No," I admitted, "but we should talk later." I said with a knowing smirk, "actually, I have a question for you. Why do you work in a sex shop and don't try on the outfits?"

Donna shrugged, "it's my job but it's because it's my mom's shop. She's the crazy sex fiend...not really but for me it's just a job, y'know?"

"So you don't use anything here?"

"Well, I have a dildo," she admitted and then a moment later, "...and a butt plug."

I cocked an eyebrow, "can I have your phone number?"

She giggled, it was very cute, "I guess but I'm not a submissive. At least, I don't think I am."

She told me get number and I programmed it into my phone, "that's okay." I told her, "hey can you keep my stepmom busy while I grab things. Tell her I want her to get at least ten outfits and if they displease me I'll spank her with one of those paddles you have with spikes. "

Donna agreed to watch my aunt as I went to get a whole bunch of items from the other side of the store. Donna put it on a tab that I made Ivy pay for without showing her anything I got. She didn't show me what she bought either but she told me it would ruin the surprise. I felt she was probably going to deserve punishment whatever it is.

Most of the rest of the day was uneventful. I didn't think I could play with Mom while Ivy was there without her catching us. And I didn't want to push Mom too much after what happened with her and Aunt Yuki earlier by making Ivy wear one of her new outfits around the house. Then Lana came home but she had to study so no fun there.

It wasn't until very late at night. Someone was shaking me awake. It was Julie and she was very drunk.

"What are you doing sis!?" I said, "where have you been all day?" I asked a little calmer a moment later.

"With Violet," Julie said, slurring her words more than a bit. Violet was Aunt Nina's only daughter, she was 18 and in school with Lana but she and Juliet had always been best friends basically forever. Julie went on, "I tried to break up with my boyfriend but he wouldn't let me." Julie sighed and then sat on the bed with me.

"What? What do you mean he wouldn't break up-" I said.

But then Juliet practically pounced on me. It was a repeat of the other day though Julie was drunk and her movements a bit inaccurate here and there but she straddled me, moving my blanket off my body. I was naked and my dick was immediately hard and rubbing at the crotch of my sister's pants and then she started kissing me.

My hands went to her ass and were surprised that it was bare but Julie was so horny she has kicked her pants and panties off and now the shaft of my hard cock was rubbing against my older sister's sopping wet pussy.

"I haven't stopped thinking about you." Julie moaned as she ground her pussy on my hard dick, "after what happened in the car, I don't care that you're my brother at all. I'm just so tired of useless men. I need a real man. I need you, Dan. I need you to fuck your older sister."

She moved slowly. Juliet put her hands on my chest and pushed her body up as her pussy traced along my dick until my dickhead was right up against my sister's pussy entrance.

But I couldn't let her do this, I gripped her hips and looked her in the eyes to stop Julie, she was very intoxicated. "Are you sure about this, Juliet?" I asked her.

"I know I'm drunk, Dan, but I've never been more sure of anything in my life." And she let gravity, more than anything else, impale her pussy on my penis.

"Oh!" My sister cried out in intense pleasure as my cock became fully encased in her tight wet cunt. I didn't have time to enjoy it right then as Julie was loud and she might wake someone up if she didn't already. I pulled her into me so I could kiss her, taking a move from mom's book I blocked the sound with my mouth.

It helped as Julie moaned more through her nose than her mouth as I kept her tongue busy. And while we made out, Julie started grinding her hips against mine. I now got time to enjoy her tight cavity as I lost my virginity to my sister. She was tight, and I was kind of surprised her vaginal walls were the perfect shape to take my hard penis but I guess that's what cunts are for, to get fucked. Hey, pussy was slick and had gripped my dick better than any hand its mouth could. And fucking my sister was the best and most pleasurable I'd ever felt in my life till then.

Julie was drunk and her motions were kind of random as she fucked me. She stiffed up and her body shook as she began to cum. Her pussy seemed to tighten as her body did and sent shockwaves through my cock and balls that set off my orgasm. I filled my sexy older sister's pussy up with my cum as we furiously French kissed on my bed.

She fell to the side of me, "fuck, that was amazing. I've never cummed like that before..." and then my sister started snoring softly on the bed beside me.

I put an arm around her but then something kept me from falling asleep. My other sister, Lana, poked her head up from the bed beside me, scaring the shit out of me.

"Well, that was fucking hot!" She whispered excitedly before suddenly taking my still hard cock into her mouth. She only sucked for a second before stopping to say, "I love how my siblings' fuck juices taste mixed!" Before sucking me back into her mouth.

I glanced at Julie lying next to me on the bed as Lana gave me a blowjob but she was sleeping soundly. As Lana sucked me she moved onto the bed and I saw that she was naked. She straddled my face and lowered her pussy onto my mouth. I started licking and sucking her clit and labia. Wow, fucking my first pussy and then licking my first pussy right after, and from both my sisters! What are the odds!?

It was delicious too. I love the taste of pussy just as much as women seemed to love the taste of my cum. I licked at her clit and entered a finger into her so I could rub her g-spot at the same time.

Sounds of both of our moans filled the room. Less than a minute later I and my younger sister were both cumming into each other's mouths.

"Mmm, delicious," Lana said as she stood by the bed, "tomorrow, I think our lesson with Mom will be interesting."

"Why's that?" I asked.

She glanced at Juliet's nude form on the bed next to me, "because tomorrow she's going to teach us how to fuck!" And with that, she left the room.

Day 24 Tuesday, April 19

I woke up with Juliet in my arms. She had such soft skin I slowly started moving my hands down her back.

"Mmmmm," Julie moaned softly, "that feels really good, Adam." That's the name of her boyfriend.

"Guess again," I said as I moved my hand to her perfect ass.

Julie's eyes opened wide as she remembered what happened, "oh no! We didn't... we couldn't have.... oh fuck!" She moved away from me on the bed.