My Mother-in-law was a Stripper

My Mother-in-law was a Stripper

And a prostitute, too.

Brian finally has sex with his future, MILF of a mother-in-law, Aileen.

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Author's Note:

This is a true story that 30-year-old, Brian asked me to write about him having sex with his sexy future mother-in-law, Aileen.

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I'm not ashamed to admit that from the first day that I met them, I've always been sexually attracted to my 48-year-old, future mother-in-law, Aileen and her 45-year-old sister, Kathleen. With them both tall, beautiful, and shapely, Irish redheads, I'm sexually attracted to older women. Maybe it's their beautiful, lush, long, red hair but I can't help myself. I love redheaded women.

Perhaps, because I never knew my mother, she died in childbirth, is the reason why I sexually lust over older women. Unable to stop myself, with Aileen and her sister my favorite masturbation scenarios, I'm always masturbating over imagining seeing my future MILF of a mother-in-law and her MILF of a sister naked and having sex with them. Seeing them naked and having sex with them are my sexual fantasies come true. If ever you met them, you'd understand why I'm so sexually attracted to them.

"Who was that Brian was talking to? They are the most beautiful and sexy women I've ever seen," said Ryan, to Murphy, Sean, and Conner, Brian's best friends.

Murphy nodded his head.

"That's Aileen, Maureen's mother, Brian's future mother-in-law. The other woman is Aileen's sister, Kathleen, Maureen's aunt. They're beautiful. I'd love to bang them both," said Murphy.

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Unable to sexually control myself, I masturbate over Aileen and her sister while imagining them naked and having sex with me. I've always imagined fondling their huge, naked, milkmaid breasts and fingering their erect nipples. Taking my time with them, I enjoy their company whenever talking to them.

Yet, every time I talk to them, I imagine making out with them. I imagine touching and feeling them through their clothes. Then, I imagine slowly stripping them naked. I imagine feeling their naked breasts, squeezing their naked ass, and fingering their naked pussies before mounting them, fucking them, and having my imagined wicked, sexual way with their naked bodies.

Whenever I'm with my future mother-in-law and her sister, especially when my fiancée isn't around, with them deliberately, sexually teasing me, I imagined them not sitting like ladies. With their knees deliberately parted enough for me to see, I imagined them flashing me their white panties. I imagined them leaning in front of me longer and lower than necessary to show me their bra clad breasts and their long lines of sexy cleavage.

While I imagined being alone with them, I stroked himself faster and harder while imagining having consensual sex with my fiancée's mother and her sexy sister. I imagined them wanting to have sex with me as much as I want to have sex with them. I imagined reaching down Aileen's blouse to feel her big breasts through her bra. I imagined reaching beneath Kathleen's short skirt to cup her panty clad pussy.

I've always imagined then on their knees and taking me in her hands and staring up at me while stroking my cock to a harder erection. I've always imagined them taking me in her mouths and blowing me. Then, after cumming in her mouths, as soon as they stand, I imagined pushing them back on the bed, mounting them, and fucking them. I'd love nothing more than to fuck Maureen's mother and aunt.

Wishing that it was more than just a masturbation fantasy, it all seemed so real. This is one masturbation fantasy that I hope comes true. Yet, picking up on something, why am I so sexually attracted to my future mother-in-law and her sister? It doesn't make any sense to be sexually preoccupied with Maureen's mother and aunt when I have beautiful fiancée who'd have sex with me anytime and anywhere.

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'Oh, my God, I just fucked my fiancée's mother, Aileen,' I thought while imagining fucking my future mother-in-law and stroking myself faster. 'I just had forbidden sex with her sister, Kathleen,' I thought while imagining fucking her sister and stroking myself harder. 'I never thought that I'd have sex with either one of them, but imagining having a sexual threesome, I imagined having sex with my fiancée, and her mother both at the same time.'

I briefly stopped stroking my cock to allow my masturbation fantasy to continue to play out in my mind. I imagined kissing Maureen's mother, French kissing her while touching and feeling Aileen everywhere through her clothes. I imagined what my future mother-in-law would look like in her bra. I imagined feeling her huge breasts through her big, white brassiere before removing her bra. I imagined seeing my MILF of a future mother-in-law topless.

'Feel my tits. Suck my nipples. Fuck me, Brian,' I imagined Aileen saying.

Clearly, I imagined her being just as horny as I am. I imagined her wanting me to touch, feel, and suck her naked breasts as much as I wanted to touch, feel, and suck her naked breasts. I imagined she wanted me to fuck her as much as I wanted to fuck her.

'Make me cum. I need to cum,' said Aileen staring up at me with sexual arousal.

I imagined Maureen's mother standing before me topless. I imagined my fiancée's mother willingly and consensually allowing me to have my wicked, sexual way with her huge, naked breasts. Then, going from one to the other, I imagined slowly undressing Kathleen and stripping her naked, too.

'Finger my pussy. Rub my clit. Fingerfuck me, Brian. Masturbate me. Give me a sexual orgasm with your fingers. I need to cum, Brian. Make me cum,' I imagined my fiancée's aunt saying.

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With me sexually lusting over seeing Aileen's huge, naked tits that are always nearly falling out of her nightgown top, my favorite masturbation plot was this. With her never wearing a robe over her low-cut, short, sheer, and sexy nightgowns, showing lots of cleavage that stopped short of exposing her erect nipples, I imagined that I had stayed overnight and slept in my fiancée, Maureen's, bedroom. With her still asleep, and with me an early riser, when I heard and smelled coffee brewing, I thought I'd go downstairs for a cup of coffee, something to eat, and to see what my future mother-in-law was doing.

With us getting along well together, I enjoyed talking to Aileen when my fiancée wasn't around. Other than what I could see of her huge, nearly naked breasts, there was something about her that made me horny. She was so pretty. She was so sexy.

I enjoyed having coffee with her while staring at whatever I could see of her huge, nearly naked breasts. There's something about a big breasted, older woman that puts me sexually in the mood. Unable to help myself, I love beautiful, older women with big tits.

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That's where my sexual, masturbation fantasy began. Every morning and every night, I masturbate over imagining seeing my fiancée's mother topless. Touching them, feeling them, and sucking them, I imagine Aileen consensually allowing me to have my wicked, sexual way with her huge, naked breasts.

As soon as I see her with her back turned to me, I imagined coming up behind her when she's standing at the kitchen sink rinsing her breakfast dishes. As soon as I see her in her sheer and sexy nightgown, I imagine pressing my hard cock against her round, firm ass while reaching around her to grab two handfuls of her double D, cup breasts. I imagined touching her and feeling her everywhere through her sexy nightgown where I should never touch and feel my fiancée's mother.

I move her long, red hair back from the side of her face to kiss her neck and snuggle up against her as if I'm spooning her in bed. When she doesn't slap my horny hand away and/or turn to scold me for sexually, inappropriately touching her and feeling her, I imagine reaching around her to cup her nightgown clad breasts in my horny hands.

'Oh, my God. She has such big tits. They are as firm as they are soft. I love her tits,' I thought while continuing to grope my fiancée's mother.

Continuing to feel her huge breasts, I finger her erect nipples. Encouraged by her assumed, sexual complacency, I continue to masturbate myself over imagining having my wicked, sexual way with my future mother-in-law's huge tits. Wishing it was more than just a masturbation fantasy, I'd give anything to feel Aileen's nightgown clad breasts.

I continue stroking myself faster and harder while imagining lifting the back of her short nightgown to feel her exposed, naked ass. With her having an ass much like her daughter's ass and her sister's ass, they all have beautiful asses. Aside from her daughter's and her sister's asses, Aileen has the best ass I've ever imagined touching, feeling, fondling, and seeing. I love Aileen's round, firm ass as much as I love her huge breasts.

When she still doesn't stop me from lifting the back of her nightgown, I expose her naked ass to my horny eyes. I continue having my wicked, sexual way with my future mother-in-law's beautiful body. Not stopping with exposing her naked ass, I imagine reaching around her to lift the front of her nightgown to expose her naked pussy.

I imagine cupping her red, naked, bushy pussy in the palm of my horny hand. Then, when she still doesn't stop me, scold, or admonish me for cupping her naked pussy in my hand, I continue sexually violating my future mother-in-law. I trace her pussy slit with my finger.

With her still not stopping me, willingly and consensually allowing me to have my wicked sexual way with her naked pussy, I imagined parting her pussy lips and masturbating her. I imagine rubbing her clit and finger fucking her pussy. I imagine masturbating my fiancée's mother.

After she allowed me to have my way with her huge breasts through her nightgown, albeit, even though it's just my imagined, masturbation fantasy, I can't believe that she allowed me to masturbate her. Going where no son-in-law should go with his future mother-in-law, I imagine rubbing her clit and finger fucking her pussy. I imagine giving Aileen a sexual orgasm with my fingers.

'Brian. Oh, my God Brian. What are you doing,' I imagined her saying while turning her head to look at me? 'I'm your fiancée's mother, you shouldn't be touching me in such a sexually forbidden way.'

Then, telling me that she wanted me to continue instead of wanting me to stop, I imagined her saying the magic words.

'If you continue masturbating me, you're going to make me cum,' she said turning her pretty head to look at me again.

Putting out her arms and placing her hands tightly on the edge of the sink, I felt her brace herself against the kitchen sink while parting her shapely thighs. Clearly, she wanted me to masturbate her. Obviously, she wanted me to make her cum.

Stunned, even though it was nothing more than a masturbation fantasy, I couldn't believe after feeling her huge breast through her nightgown, she allowed me to lift the back of her nightgown to feel her naked ass. Not making a move to stop me, I couldn't believe she allowed me to reach around her to lift the front of her nightgown. I couldn't believe she allowed me to have my wicked, sexual with her naked pussy. I couldn't believe that my fiancée's mother allowed me to masturbate her.

'Don't stop rubbing my clit. Don't stop finger fucking my pussy. I'm cumming, Brian. I'm cumming,' I imagined my fiancée's mother saying while having a sexual orgasm from me rubbing her clit, finger fucking her pussy, and masturbating her.

As soon as she was wet enough, I imagined pulling out my stiff prick. With a hand to the back of her red, pretty head, I imagined bending her forward and fucking her. I imagined fucking my wife's mother, my future mother-in-law. I imagined fucking Aileen hard enough and fast enough to give her another sexual orgasm, this time with my cock.

While her daughter slept upstairs, I imagined Aileen blowing me and me cumming in her mouth. I imagined her fucking me and me cumming in her pussy. Then, while continuing to stroke my cock faster and harder, I imagined having sex with her MILF of a sister, too.

Alas, with me cumming all over my hand and all over my stomach, instead of having forbidden sex with Maureen's mother and her aunt, that's where my masturbation fantasy ended. I never got further than that. A one-sided, sexual affair, I always wished my sexual fantasy continued. I'd love to know how my masturbation fantasy ended after I stripped Aileen naked and had my wicked way with her beautiful, naked body before having sex with her sexy sister, too.

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Unbeknownst to me, something I never could have imagined, back in her day, my future mother-in-law, Aileen, and her sister, Kathy, were strippers, prostitutes, and whores. Who knew? Something that I never would have imagined, I had no idea.

Unless I discovered photos of them naked at a strip club and having sex with a variety of men in the VIP room, there was no way to tell what they did in their past lives nearly, twenty-years ago. Only, taking photos weren't allowed in a strip club and especially not in the VIP room. Yet, it was sexually exciting to know that my MILF of a mother-in-law, Aileen, and her sexy sister, Kathleen, slowly stripped off her clothes while dancing around a pole to music. It was sexually exciting imagining my future mother-in-law and her sister having paid sex in the VIP room.

Now, that I think about it, who wouldn't want a mother-in-law who once was a stripper and a prostitute? With her no longer having a man in her life, after I married her daughter, I thought about all of the sexy fun that I could have with my whore of a mother-law and/or with her prostitute of a sister. I masturbated over touching them, feeling them, kissing them, making out with them, spying on them, exposing myself to them, masturbating in front of then, stripping them naked, and maybe even having forbidden, deep penetrating sex with them.

'It's okay. My wife gave me her blessing to have sex with her mother and her aunt. They are my mother-in-law and her sister,' I thought as my excuse to have forbidden sex with them. 'Moreover, they are ex-whores, strippers, and prostitutes. No doubt, they both want to have sex with me as much as I want to have sex with them.'

With them once strippers, prostitutes, and whores, I imagined that Aileen and her sister would allow me to willingly and consensually sexually do anything that I wanted to do to her nightgown clad and/or her naked body. Yet, even though what she once was in her past, once a whore always a whore. With a leopard unable to change her spots, no doubt, they are still whores. No doubt, as much as I'm sexually attracted to my future mother-in-law and her sister, with them unable to resist my good looks and muscular body, they're both as sexually attracted to me as I am to them.

'Yet, forget about her sister, my future mother-in-law is the one that I really want. I'd love to make out with her while touching and feeling her everywhere through her clothes before slowly stripping her naked. I'd love to have forbidden sex with her. Without my fiancée ever knowing that her mother is my whore, and that we're having forbidden sex, I'd love to make her my personal slut and my sexual slave.'

Now that she once willingly and consensually removed her clothes, and embraced the Devil in her life of paid sex, I imagined she'd willingly and consensually do it again for the right amount of money. Tempted once, no doubt, she could be tempted again. Harder to have paid sex the first time but what's stopping her from having paid sex again?

Without my finance needing to know, I'd willingly pay whatever my future stepmother wanted for me to have sex with her. My masturbation, sexual fantasy come true, I'd love to have sex with my wife's mother. Maybe with me soon to be in the family, giving me the family discount, she'd have sex with me at a discounted rate or even for free.

I can't stop thinking of having sex with my future mother-in-law, Aileen. For that matter, I can't stop thinking about having sex with her sister, Kathleen. I can't stop thinking about having sex with both of them at the same time. How hot would that be to have consensual sex with two, beautiful, older women?

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There is nothing more sexually exciting than discovering that my MILF of a future mother-in-law and her sexy sister were once strippers, prostitutes, and all-around whores. How hot is that to discover that information about their sordid, sexual pasts? If I had never imagined having sex with my fiancée's mother and her sister before, I definitely wanted to have sex with them now.

Always thinking better of them, thinking that they were modestly moral, church going women, I had no idea that my future mother-in-law and her sister were both cocksucking whores. With neither one of them having men in their lives, now I knew how they earned enough money to buy a house and always have a new car. Careful with the money they earned, investing it wisely instead of spending it foolishly, they sold sex for money and earned money for sex.

Now that I knew what they were, with their big tits and shapely asses, indeed, even now, while watching what they eat and exercising, they both have the shapely and sexy bodies of high-priced strippers. With me not as sexually savvy as I thought I was, what should have been obvious to me, wasn't. Now that I know what they used to do for a living to earn money, it made sense that they sold their hands, their mouths, their asses, their pussies, and their naked bodies for sex. With their pretty faces and tall stature, they could have been models.

Yet, with everything all about sex, I don't kid myself, sex sells. Freely having consensual sex to advance their modeling careers, most models are whores. I know because I once worked for a famous modeling agency in Boston. Whenever they had a cat call, there'd be more than 100 models talking about haircare and skincare products, and sex.

Come to think of it, many women, perhaps, even their sweet mothers and/or their beloved grandmothers, may have been whores once upon a time. With them only having their fading beauty and their shapely bodies to attract men before becoming fat from birthing babies, many women would willingly and consensually do anything for money, even have paid sex. Something easy for them to do, they'd even sell their bodies for money.

While acting modestly shy, allowing men to photograph them in all manner of undress, women who are desperate for money, at the very least, would pose naked for money. While acting like the virgins that they once were but are not now, allowing men to have sex with them, many women would fuck and suck any man for money. I'm no sucker, most men believe that men are better than women and more superior to them. Taking sexual advantage of men, wrapping men around their money grubbing fingers, many women are conniving whores willing to do anything for a buck.

Many women have gotten the better of men by tempting men with their sexy and shapely bodies and with the promise of sex. Yet, to get where they are, many famous women have had sexually, sordid pasts. It's common knowledge that Nancy Reagan, President Ronald Reagan's wife, was the Hollywood, blowjob queen. She willingly and consensually put on her knee pads, moved to her boney knees, and blew powerful men to get acting rolls.

"Blow me, Nancy, and I'll make you a star. I'll give you the lead, acting role in my next major, motion picture," said her director in his trailer on the MGM back lot.

Obediently obeying him, Nancy signed a contract to be the star in his next major, motion picture. Then, she gave him a sexy smile and a naughty look.

"Just let me put on my knee pads," said Nancy Davis, her maiden name before she married Ronald Reagan.