Blacmailing Stepmom and Stepsister

Blackmailing Stepmom and Stepsister

Promising not to tell their dirty, little secrets, Stepson blackmails his hot stepmother and his sexy stepsister for sex.

Author's Note:

Even though I'm not blood related to my stepmother and/or to my stepsister, because we lived beneath the same roof together, sex between us is considered incestuous.

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Valentino, a horny and sexually frustrated stepson, and a vengeful stepbrother, threatened to tell their dirty, little secrets to everyone. He blackmailed his MILF of a stepmother, Virginia, and his sexy stepsister, Victoria, in exchange for them giving him illicit sex. With him knowing all that they've done and all that they continued doing, threatening to ruin their reputations in the community, sex for silence was his game to play.

Unembarrassed to admit, ever since I turned eighteen-year-old, I've been sexually attracted to my forty-six-year-old stepmother, Virginia. Who wouldn't? As sexy as she's shapely, she's drop dead gorgeous.

Having raised me since I was a baby, after my mother died in childbirth, never knowing my real mother, I've always thought of her as my real mother instead of my stepmother. Unbeknownst to me at the time, another one of their deep and dark secrets, my dad was unfaithful to my mom. What else is new? As many men do, my father cheated on his wife, my birth mother all through her pregnancy with his lover, my future stepmother, Virginia.

After my mother died on the operating table, he married his lover, and she even named me. Twenty-four-years later, with her now fifty-two-years old, and looking ten-years younger, I'm now 24-years-old. As I was six-years ago when I was eighteen-years-old, nothing changed, I'm still sexually attracted to my stepmother. My masturbation fantasy woman, she's beautiful.

Even though I'm old enough to have a hot girlfriend of my own, because of not having any money, I don't. Instead, I masturbate every morning and every evening over imagining seeing my stepmother without her clothes and her having sex with me. With me a masturbation machine, and my lustful desires towards her nothing more than a forbidden fantasy, she'd never allow me to see her without her clothes, nor would she ever have sex with me. She may have been a whore in her younger days when she cheated on my mother with my dad, but she was my father's whore.

Doing a total turn around after my dad died, with her finding religion, my stepmom is morally modest when around me. She always wears a robe over her nightgowns. A church going and God fearing woman, maybe she did years ago but, I seriously doubted that my stepmother masturbates. With her not a whore but a now good, kind, and loving woman, a caring mother and my stepmother, the only time she's on her knees is to pray. Unable to imagine her with a prick in her mouth, with me having a high opinion of her, I seriously doubt if she sucks cock.

Frustratingly, even though I'm always looking and staring while undressing her with my horny eyes, I've never seen upskirt peeks of my stepmother's panties. Something that I'd love to see, I've never seen up nightgown views of her naked pussy. Again, something else that I'd love to see, I've never seen down blouse views of her cleavage and her bra. Even though I'd love to see more of her, I've never seen a down nightgown view of her naked breasts, her areolas, and her nipples. Frustratingly, I've never seen as much of her as her bra strap.

Nevertheless, while envisioning all that I wasn't seeing, have never seen, and will never see, I lost count how many times that I've masturbated over my stepmother. I played with myself while imagining seeing upskirt peeks of her panties. I stroked myself while envisioning seeing her pussy mound, her camel toe, her pussy slit, and her patch of red, bushy, pubic hair through her sheer panties.

I've masturbated myself while visualizing seeing my stepmother's low-cut bras and her long line of sexy cleavage in down blouse views. I continued stroking myself while picturing seeing her naked breasts, her areolas, and her nipples in down nightgown views of her enormous tits. I've played with myself while imagining her topless and/or naked and her having sex with me. Sadly, just as I'll never see her topless and/or naked, she'll never have sex with me.

Nothing more than a masturbation fantasy, my stepmother is the forbidden fruit of my desire and illicit lust. I'd give my right arm, literally, to see her without her clothes, and have sex with her. I'd do anything to sleep in her bed while holding her, hugging her, cuddling her, and spooning her. I need, I want, and I must have sex with her. Only, sadly, while wishing she was still a whore who wanted to have sex with me as much as I'd love to have sex with her, a born again Christian woman, she'll never have sex with me.

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After my stepsister moved out to live on her own, now that I'm living alone with my stepmom, with me having plenty of opportunities to do so, I've been tempted to dick flash her. While making my exhibitionism appear accidental, I'd love to expose myself to her. Something perversely perverted for me to do, I'd love her to see my erect, naked prick.

Easy for me to expose myself to her, I thought of all of the deliberate ways that I could dick flash her while making my flashes appear accidental. With her always barging in my bedroom without knocking to deliver my laundry, while lying on my bed naked with my eyes closed and wearing headphones, I've been tempted to allow her to catch me masturbating and cumming. Giving me more to masturbate over, I wonder if she'd stay in my room while watching me play with myself, or if she'd leave and close the door behind her.

Then, after emerging from the shower and walking into the living room as if I had something important to tell her, I thought about deliberately dropping my towel in front of her to show her my naked prick. While slow to pick up my towel, and wrap it around me, with her tied towels never falling, I imagined asking her to show me how to tie a towel around my waist so that it wouldn't fall. Something she'd never do is something that I imagined her doing. I imagined her opening my towel wide to tie it tighter while she ogled my naked prick.

I racked my brain while trying to think of other ways to dick flash her while making my flashes appear unintentional. I've thought of stroking myself to a big and hard erection while hiding from her in the kitchen. Then, I thought about removing my erect, naked prick from my pajama pee hole, leaning over her, and exposing my prick to her while serving her coffee. I'm curious for her reaction to her seeing my big dick up close and mere inches away from her beautiful mouth.

Not knowing what she'd say or do, I'm curious for her reaction to seeing my naked, erect prick. I can only imagine what her response would be while I continue masturbating myself in my bedroom or in the bathroom over the thoughts of dick flashing her. Even though I'd love to show her my prick, something that I'd never do, I don't dare disrespect her in that despicable way.

Yet, I still wonder. If I did dick flash her, would she look? Would she stare? Would she look away in shame and in embarrassment? Would she tell me that I'm exposed? Would she scold me for deliberately dick flashing her my naked prick? I don't know. I had no idea until I exposed my naked cock to her.

Even though she'd never do it, while dick flashing my stepmother, I masturbate over her taking me in her hand. While staring down at it, I imagine her sliding a slow finger over the head of my engorged prick, and squeezing my cock before slowly stroking my dick while staring up at me and smiling. While she strokes my prick, I imagine her allowing me to touch and feel her through her clothes. I'd love her to give me a motherly hand job. I'd love to cum for her.

Then, again, something she'd never do, I visualized her moving to her knees not to pray but to take me in her mouth and suck me. I stroke myself over her blowing me. I stroked myself faster while I imagined cumming in her mouth. I stroked myself harder as I envisioned her swallowing my cum. Something she'd never do but something that I loved visualizing her doing when playing with myself, I'd love her to give me a blowjob. How hot would that be for her to blow me?

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Even though I'm perversely perverted to continually masturbate over imagining her naked and having sex with me, I can't dick flash her. That's just wrong. That's just nasty. She's my stepmother and, not knowing what I'd do without her in my life, I love her. What's wrong with me for even thinking about disrespecting her by dick flashing her?

She's my best friend and confidant. We have a close stepmother and stepson relationship. We get along well together. We laugh, we joke, we tease and, not keeping secrets from one another, we tell each other everything.

We play board games and card games. We do jigsaw and crossword puzzles together. We watch television and movies together while sitting and cuddling on the couch. She drinks her wine and I drink my beer. As if she's my live-in girlfriend instead of my stepmother, I love spending time with her.

No exaggeration, my stepmother is a MILF of a woman. Because my father was tall, 6' 2" tall, I'm 6' 3" tall. She's my perfect and preferred height. She's 5' 9" and 6' tall with her high heels. She has red hair with big, blue eyes, double D cup breasts, and freckles. My sexually frustrating burden to bear, as if she was made for me, I love older, redheaded, big breasted women with freckles.

Indeed, I love my stepmother. I truly love her. Only, I love her not in the way that an adoring stepson should love his stepmother. Oh, no. I love her in the way that a horny man filled with lustful desire loves a woman.

Something that will never happen, nothing more than a forbidden fantasy, I wish I could see her without her clothes. I wish I could see her in her bra and panties, topless, and/or naked. I wish I could have incestuous sex with her. I'd love nothing more than to make out with her while feeling her through her clothes. Then, while continuing to make out with her, I'd love to slowly undress her. I'd love to strip her naked. Finally, I'd love to touch and feel her naked body everywhere.

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Alas, far from a perfect world, then, there's my stepsister, Victoria. God help me. Unashamed to confess, I've always hated my twenty-eight-year-old, big stepsister. She's a bitch. She hits me, slaps me, pinches me, scratches me, punches me, kicks me, calls me names, and has even spitted on me throughout my living with her. With us never getting along, she hates me as much as I hate her.

Yet, her saving grace, she's a very pretty woman. She's as tall as her mother. She's 5' 9" and 6' tall with her high heel shoes. She's a natural, blonde with green eyes, and D cup breasts.

Indeed, if I didn't hate my bitch of a stepsister as much as I do, I'd be sexually attracted to her. She not only has a pretty face but also, she has one hell of a body. Even though my stepmother still looks really good now, my stepsister looks what my stepmother used to look like twenty-years ago.

Being the pervert that I am, I know their bra cup sizes because they hang their wet bras over the shower curtain rod. Unbeknownst to them, I've visualized seeing them both topless and naked while having sex with them. First, of course, I'd have sex with my stepmother, who I love, and then, I'd have sex with my nasty bitch of a stepsister, who I hate. Unable to control my corrupt lust for them both, as if touching and feeling them through their clothes, I've masturbated over touching and feeling their bras as well as sniffing their used panties.

With them having a drawerful of colorful underwear, I love their sexy lingerie. While imagining cumming in their pussies, I enjoy cumming in their used panties. I wipe the evidence of my lust away with toilet tissue, and return their dirty panties to the laundry bin. Then, when they wear their clean panties that I had sex with, I laugh with the thought that they're wearing the panties that I ejaculated my cum in the crotches of their used panties.

After my dad died of COVID, with him making all of the money as an accountant, everything changed for the worse. Unable to live on our own, pooling our meager resources to help make up for his lost income, we continued living together to financially help out our family make it through the month. Barely surviving, and barely affording to pay the mortgage, buy food, gas, and pay the rest of our monthly expenses, we lived from week to week. We had no money. Like most people who work two jobs to make ends meet, we were middle class poor.

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Then, suddenly, and seemingly out of the blue, as if my stepmother and stepsister had won the lottery, everything changed for the better for them but not for me. Not going anywhere and not doing anything but working, hunkered down in my bedroom writing computer code for a software company, I was depressed. With nothing changing for me, my life was still as miserable as it was before. I was nothing but a perversely perverted masturbation machine, a man who depravedly lusted over his stepmother and, hating to admit, his stepsister, too.

Sadly, truthfully, and unbelievably, my best time was masturbating over my MILF of a stepmother and my bitch of a stepsister. How fucked up is that? Continuing to self-abuse myself, my social, love life without having a woman of my own was confined to my right hand going up and down on my cock.

Then, suddenly, my stepmother and stepsister were always online shopping. They bought new clothes, shoes, and handbags, lots of clothes, shoes, and handbags. Totally stunned that she could afford it, Victoria bought a condo in a high-rise building downtown. She bought a brand new Mercedes, too. My stepmother bought a new vehicle, too, an expensive sports utility vehicle.

What the fuck? How they could afford all that they bought and continued buying even more stuff was beyond me? My only explanation is that they won the lottery and didn't tell me. Only, as stunned as I was sexually excited to learn, I was wrong in my suspicion as to how they suddenly got rich while I was still poor.

With them suddenly having a lot of money, and me still living at home with my stepmother, while driving around in my beat up, old Mustang GT, I was poor and, suddenly, they were rich. They both claimed that they earned their money working from home. Working from home? I work from home and I'm not rich. I'm poor. While wondering what they did and were continuing to do to be as financially successful, not answering me, they brushed off my questions and changed the subject.

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My name is Valentino. For some odd and inexplicable reason, my stepmother has a thing for four syllable names that begin with the letter V. Perhaps because she had a four syllable name beginning with V, Virginia, she gave her daughter a four syllable name beginning with V, Victoria, and gave me the four syllable name beginning with V of Valentino. Actually, I discovered later that Valentino was the name given to me by my stepmother because of her mother, my step grandmother, Grace. She loved Rudolph Valentino.

Whoever he was, I had no idea. I never heard of him. Long before my time, I discovered later that he was an Italian movie star from the days of silent films. As if depressing the mute button through the movie while turning on the closed caption, I can't imagine watching a movie without sound. It would be annoying to constantly look away from what was happening on the screen to read the closed captions.

Glad that they didn't name me Rudolph, everyone called me Val. I guess if my name was Rudolph, my friends and my family may have called me Rudy. That wouldn't be so bad. I'm a 24-year-old horny and sexually frustrated man without a girlfriend and living at home with my single stepmother while lusting over her. Now, that's bad. How sad is that?

Girlfriends cost money, and I don't have any extra money to spend on a woman. Besides with me still living at home with my stepmother, unless the woman of my desire invites me to her place, I have no place to take her for sex. After my stepsister moved out to live on her own, I'm relegated to continuing to masturbate while sniffing my stepmother's panties and feeling her bras. Again, how sad is that?

Then, one day, as if a bright light from heaven shined down upon me, a miracle transformed my life. Suddenly, as if I won the sexual lottery, everything changed for the better. As I always do when I'm not working, writing computer code, perusing porn sites online, while masturbating, always stroking my cock, I saw a familiar face.

As if I was looking at the FBI's ten most wanted poster, I recognized someone that I know. Not believing my horny eyes, I saw my stepsister, Victoria. Making no mistake, instantly recognizing her, it was her. I'd know my own stepsister.

Unbelievably and something that I never imagined her doing, she worked as a webcam model for a porn site online that I had never been on and happened to stumble over. She was topless. My bitch of a stepsister, Vicky, was topless. If it wasn't enough that I found her working as a webcam model, I saw my stepsister's naked breasts.

My first time seeing Victoria's naked breasts, I couldn't believe that she was topless. I couldn't believe that I was seeing her big, shapely tits. Unable to wrap my head around it, hard for me to believe my stepsister was topless. Difficult to wrap my horny head around, as shocked as I was excited, I couldn't believe that I was seeing my stepsister's D cup, naked tits, her areolas, and her big, erect nipples.

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She was only wearing bikini panties with a pink masturbation toy peeking out from the side of her underwear. Not surprised, with her having a bevy of boyfriends and always coming home late, and drunk with her blouse buttoned in the wrong holes, I always knew my stepsister was a whore. Now, not only is she a whore but also, I'm shocked to discover that she's a webcam model on an X-rated, adult online site.

Again, unable to wrap around seeing Victoria topless, I still couldn't believe that I was seeing my big stepsister's naked breasts. Never have I stroked my cock over imagining seeing my stepsister's tits as I did that day when seeing her naked breasts online. Before the pay for view site locked me out for not joining as a member, I spent as much time as they gave me to stare at my topless stepsister. I continued logging back into the adult video site without joining while masturbating over Vicky's big tits.

Unlike my stepmother, no doubt about it, my stepsister is definitely a whore. Something that I never noticed before, that she must have recently gotten, she had a tongue stud, too. Not having to wonder about it, she definitely sucked cock. One of her nipples was pierced, too.

Again, something that I never noticed before, not paying much attention to my stepsister, and having never seen her without her blouse and/or her bra, she had tattoos. She had tattoos everywhere. She had a dozen colorful tattoos on her arms, her shoulders, her chest, her legs, and on her back.

My first time seeing her topless, no longer bothering to go to any other adult entertainment sites, this was now my favorite pornographic site to visit. No matter that I still hated her, I continued viewing her webcam site every day while looking for my sexy stepsister's page. Giving herself a fake name, she had her own webcam page under the name of Vivianna.

Of course, returning to the site every day, better than masturbating over imagining Victoria topless, I played with myself over seeing my stepsister topless and touching herself. I watched her feeling and fondling her naked breasts, cupping her breasts, and pinching, pulling, turning, and twisting her erect nipples. Customers, men, and women, paid her in tokens for her to do sexy things to her beautiful, topless, and nearly naked body.