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My Mother Hired a Male Stripper #1

My Mother Hired a Male Stripper #1

by Motherandsontrueconfessions
20 min read
3.84 (20000 views)
sex with mothersex with sonsex with auntsex with nephewsex with grandmother
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My Mother Hired a Male Stripper, #1

Promising to be a big, blowout bash, my mother, Susan, hired a male stripper for her sister, Maureen's, 40th birthday party.

My name is Jimmy, and I'm 22-years-old. After graduating from college and even after getting a job working from home, still unable to afford my own apartment, I returned home to live with my mother. Making me feel good about my decision to return home, welcoming me home with open arms, hugging me and kissing me, she was ecstatic about having me continue to live with her. I loved my mother, and she loved me.

She divorced my father years ago. Always arguing over everything, especially over money, the last straw was when he cheated on her with his young, sexy secretary. I think my mother could have forgiven him for cheating on her had he cheated with a woman her age, but with the other woman so young, she couldn't compete with her.

I could have moved in with my dad, but he lived in California with his whore, a woman nearly half his age, not much older than me, she was closer to my age. Awkward moving in with them at best, I didn't want to live in Los Angeles. Besides, happy to help her, my mother needed my financial assistance.

We've always had a close and mother and son relationship. Allowing me to concentrate on my work, she did all of the household chores. She did the laundry, the cooking, and the cleaning. She did the food shopping and ran all of the errands.

Why would I continue not living with my mother when I had a maid, a laundress, a cook, a cleaner, and a woman who loved me? The best roommate that I could have, other than a wife, the only thing my mother didn't give me was sex. I'd never turn down my mother if she offered to give me sex.

Something that I routinely masturbated over doing, I'd love her to stroke my prick while she allowed me to feel her naked breasts and finger her erect nipples. I'd love to make love to her. I'd love to fuck her.

Able to work longer hours while living at home with my mother, why would I spend every dollar to afford an apartment and live on my own when I'd be more comfortable living with my mother? I'd be giving up too much when leaving home and financially struggling to rent my own place. With rents so high, I'd have to find at least one roommate. With me a person of habit and routine, I didn't want to live with anyone other than with my mother.

Embarrassing me and making me feel a bit uncomfortable, she told me that I could even invite a woman home. Whenever I wanted to do that, she'd go out shopping at the mall with her friend and go to her house for tea. Actually, if only my mother knew the women who revved my engine, the only women that I was interested in were older women, women twice my age, women my mother's age and older.

Taking it slow, I wasn't ready for big changes in my life. I preferred keeping things familiar, living in the same house, in the same neighborhood, and having same group of friends, that is, until and whenever I found my true love. I'm not ready to get serious with anyone, yet. I'm not even dating. If I was to date anyone, I'm more interested in dating a mature, single mother than a young and annoying daughter.

# # #

Something that every son is when having a mother who looks like her, since the age of 18-years-old, I've been sexually attracted to my mother. Unembarrassed and unashamed to admit, with me horny, I'm always trying to see something of her that I shouldn't see. Now that I'm older and have sexual needs, I love my mother but not in the way that a son should love his mother. I love her in the way that a man loves a woman.

Denying me a peek, never leaving her bedroom or her bath-room doors ajar, she dressed and undressed with her bedroom and bathroom doors tightly closed. Denying me a view, she always wore a long robe over her short, sheer, low-cut, and sexy nightgowns. Now that he's living on the other side of the country with his whore, my father bought her lots of revealing nightgowns that I wished she'd model for me. A church going and a God-fearing woman, a goody-two-shoes, she's modestly moral.

Sometimes, she reminded me of Mary Cooper, Sheldon Cooper's mother, played by Zoey Perry, in the recently ended television series, Young Sheldon, a spinoff from The Big Bang Theory. With her attitude about sex, morality, and religion, much like Sheldon's mother, even though she has the body of a stripper, my mom is more of a holy roller than she is a sexpot.

Too good to be true, she doesn't curse or smoke. As if she's a Buddhist, a Latter-Day Saint, a Seventh-Day Adventist, or a Holy Pentecostal, I've never seen her take a drink. Much like me, already set in her ways and in her routine, like mother like son, we're much alike.

'Yet, how could someone so beautiful, so sexy, and so shapely be so boring,' I wondered? 'No wonder why my father took up with a young whore.'

Even though she loved music, I'd never seen her let her hair down and dance. Watching a woman dance is a big turn on for me, I'd love to see my mother dance. Just once, I'd love to see my mother drunk. I'd love to see her being naughty by flashing me something that I shouldn't see of her. I'd love to hear her talking dirty while swearing like a sailor.

# # #

Had she not married my dad and became pregnant with me, she could have been a nun, Sister Susan. Only, nuns must take a name other than their own name. I wondered if there are nuns who have taken sexy names, such as Veronica, Erika, Lexi, Tiffany, Vanessa, Crystal, Destiny, Lolita, or Lulu.

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Giving me something more to masturbate over whenever I imagine my mother naked and having sex with her, at the very least, something I've yearned to see, I'd love to see an upskirt peek of her panties. Something that I imagine seeing when stroking myself, I'd love to see her panty clad pussy mound, her camel toe, and her pussy slit. Not knowing if her pussy is bushy, trimmed, or shaved, I'd love to see her blonde, pubic hair through her sheer, bikini panties.

I'd love to see a down blouse view of the tops of her breasts, her long line of sexy cleavage, and her low-cut bra. Yet, whenever she leaned forward, careful not to flash me, and denying me a down blouse view, she placed her hand to the top of her blouse and closed it. Then, with her long and shapely legs crossed, or her knees tightly cemented together, denying me a peek of her underwear, she sits like a lady. Unfortunately, and sexually frustrating for me, my mother is not the incestuous whore that I wished her to be.

'With every man having wants, needs, and sexual desires, no wonder why my father left her for a young whore,' I thought again. 'In the way that I imagine my father's whore is a cocksucker, my mother probably doesn't suck cock.'

Just once, again, giving me something more to masturbate over while imagining her naked and her having sex with me, I'd love to see her in her short, sheer, sexy, and low-cut nightgowns without her wearing a robe. I'd love to see her in her revealing bra and bikini panties. Some-thing that will never happen, and something that I stroke my cock over fantasizing nearly every day, I'd love to see her topless and/or naked. Whatever I saw of her, I'd masturbate over that image for the rest of my horny life.

# # #

To be honest, my mother is not the only older woman that I'd love to see without her clothes. I'd not only love to have sex with my 43-year-old mother, Susan, but also, I'd love to have sex with her 40-year-old sister, my aunt, Maureen, too. Further, not turning her away for eating crackers in bed, I've even masturbated over imagining my 65-year-old grandmother, Joan, topless and naked while having sex with her, too. Looking ten-years younger than her age, she's still a good-looking woman.

A family of broken marriages, unkept promises, and unfulfilled dreams, many women in my family and in my extended family, friends of the family, my mother's friends and my aunt's friends are divorced. In the way that I don't have a woman in my life, many women in my family and my extended family don't have men in their lives. With my grandmother and her best friend widows, their husbands died younger than they should have from smoking, over-eating, and drinking.

With me not very experienced with women, I wondered if my mother, my aunt, and my grandmother are horny living without a man in their lives. Something that I can't imagine them doing, I wondered if they masturbate. I'm unable to envisage them playing with themselves with their vibrators and/or with their dildos, if they even have those sex toys. I can't visualize them touching themselves while imagining making love and/or fucking. I can't picture them fingering their pussies while fantasizing about stroking and sucking cocks.

They don't strike me as the type of women who'd finger their pussies while pinching, pulling, turning, and twisting their erect nipples. Unable to go there, other than imagining them having sex with me, I can't imagine them stroking, sucking, and fucking someone, anyone. I seriously doubt if any of these women are cocksuckers. Yet, my mother must have had sex with my father, at least once, for her to become pregnant with me.

Not every woman masturbates, or do they? I don't know. I have no idea. I can't imagine my mother, my aunt, and my grandmother playing with their pussies. I just can't go there. All good, Christian women, they're not the whores that I wished they were in the way that I'm a pervert. They don't desire me in the way that I lust over them. They'd never have sex with me in the way that I'd love to have sex with them.

It's enough that I masturbate every day, multiple times a day. Yet, I doubt that women play with themselves as much as men. Seemingly, they're satisfied with getting their emotional needs and dreamy desires from romance novels and Hallmark movies. Nevertheless, I'd love any of them or all of them to blow me. I'd love to cum in all of their mouths.

# # #

My kind of women, I'm surrounded by hot, older, and busty women. I'd love to have sex with my mother's 42-year-old, best friend, Brianna. Tall, blonde, shapely, and sexy, she's beautiful. Yet, why would she have sex with a 22-year-old man when someone who looked like her could have sex with any man?

I'd love to have sex with my aunt's 40-something-year-old best friends, Carol, and Nikkie. They're sexy, shapely, and pretty. With me horny enough, I'd even have sex with my grand-mother's best friend, Mary. Again, like my grandmother, looking ten-years-younger than her age, she's pretty for an elderly woman. Lastly, Natalie, with her always hanging around the house, a longtime, family friend, with her having big tits, I'd love to have sex with her, too.

Not fussy about who I'd have sex with, as long as they're older, good-looking, and have big breasts, I'd have sex with any and all the women that I know. I've played with myself over all of them while imagining them naked and having sex with me. If only they knew how much I lusted over them, I'd be embarrassed. Yet, I wished that I could have sex with them. Ashamed of being the pervert that I am, I wouldn't want them to know how much I sexually wanted and masturbated over them.

Coming in contact with older women every day, unable to help who I'm sexually attracted to, I love older women. When my aunt, grandmother, and my mother's best friend aren't visiting my mother, her family friend is visiting. Again, with all of the big breasted women that I know, I love women with big tits, the bigger the better. Unable to help myself, I don't know why I've always been attracted to busty and mature women.

Where most men my age prefer women their age and younger, I'm the opposite. I see beauty in wisdom and in wrinkles. Sometimes, I'd rather have a thought-provoking conversation than sex. Instead of being with an empty-headed younger woman, I prefer a woman who has a brain in her head and experiences to share. With many men having the opinion that breasts more than a mouthful is too much, I don't share their opinion.

That's not how I feel about women's breasts. Perhaps because my mother didn't nurse me, I can't get enough of tits. I love tits, all shapes, and all sizes, especially big breasts. As far as I'm concerned, the bigger the breasts the better. There's just something about a tall, beautiful, older woman with big breasts.

Much better than short and fat, older women with small breasts, women who no longer take care of their personal appearances, I prefer older women who pay attention to their hair, their make-up, their body, and their clothes. Older and more mature women have a way about them. I love how they carry themselves. I love how they always look so tastefully professional. I love when they surprise me with all that they know and have experienced.

Yet, just once, instead of having to imagine them naked while having sex with me, I'd love to see something of somebody to give me more to masturbate over when I'm horny. Unlike many of the younger women who sit like sailors and/or who don't wear panties or bras, seemingly, older women love sexy lingerie and sit like ladies. Apparently, in the way that younger women always do, older women are too modestly moral to flash me upskirt peeks of their panties and down blouse views of their cleavages and bras.

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# # #

As if lost in a field of beautiful flowers, they fill my nose with their floral perfumes. They satisfy my senses by allowing me to look at them, watch them, and stare at them. While wishing I could hold them, smell them, touch them, feel them, fondle them, and have sex with them, I'm enthralled by beautiful, busty, older women.

My mother, Susan, is 5' 9" tall with blonde hair, blue eyes, and D cup breasts. Her sister, my aunt Maureen is 5' 9" tall with red hair, blue eyes, and double D cup breasts. Their mother, my grandmother, Joan, is 5' 7" tall with brown hair and brown eyes, and D cup breasts.

My mother's best friend, Brianna, no doubt a whore, works as a webcam model. She's 5' 10" tall with dyed, blonde hair and B cup breasts. My aunt's best friend, Carol, is 5' 7" tall with dyed, blonde hair and C cup breasts.

Another friend of my aunt's is Nikki. She's 5' 4" tall with brown hair, a beautiful smile, and has huge, double D cup, surgically implanted breasts. Like Brianna, no doubt, another whore, she works as a webcam model, too.

Beautiful and sexy women earn a lot of money exposing their topless and naked bodies on the internet to admiring men who willingly pay to watch them strip naked and masturbate them-selves. Not interested in any of that, I'd rather have a woman standing in front of me without her clothes. I need to touch, feel, fondle, and make out with a naked woman rather than just stare at one on my computer screen while playing with myself.

# # #

My grandmother's best friend is Mary. She's 5' 5" tall with red hair and C cup breasts. Like my grandmother, she's 65-years-old. Natalie, our family friend, is 5' 10" tall with black hair and D cup breasts. I don't know her age but, even though she looks ten-years younger, I'd guess that she's in her early fifties.

I'm tempted and distracted by beautiful, older women with big tits. Everywhere I look, unable to look away, I see blouse and bra clad breasts. I continually masturbate over making out with busty, mature women while feeling them through their clothes. Then, looking to see what each unbuttoned button revealed before unbuttoning the next button, I continually stroke myself over slowly unbuttoning my mother's, my aunt's, my grandmother's, and all of their friends' blouses.

Alas, something that will never happen, I'd love to see, touch, feel, and fondle their naked breasts while fingering and/or sucking their erect nipples. Curious for their reactions, again, something that will never happen, I'd love to expose my naked, erect prick to all of them. If I dared to dick flash them, I wonder if they'd look with curiosity, stare in sexual arousal, or look away in embarrassment, shame, and disdain.

Nothing but a fantasy when masturbating myself, I'd love for any of them or all of them to stroke my cock, suck my cock, and/or fuck my cock. Alas and again, nothing more than a sexual fantasy that I masturbate over, how hot would that be to have sex with a harem of older and busty, beautiful women? Whenever I masturbate, seemingly, all the time, I imagine all of the eight, older women that I know naked and having sex with me.

I stroke myself over making out with them while imagining feeling their breasts through their blouses and bras. I play with myself while I envision undressing them and stripping them all naked. I masturbate myself while I visualize making out with them, making love to them, and fucking them. I continue to stroke myself while picturing myself fingering their pussies and licking their pussies. I ejaculate while envisioning them stroking my cock, sucking my prick, and allowing me to cum in their mouths.

# # #

Then, finally, something that I never expected nor could have imagined, the perfect opportunity for me to, hopefully, have sex with some or with all eight women presented itself. My mother hired a stripper for my aunt's big bash, 40th birthday party. I couldn't believe my holy roller and holier than thou mother hired a stripper as a surprise for her sister. I couldn't believe that my mother, her sister, my grandmother, and their friends would see, touch, feel, suck, and perhaps, even fuck the cock of a stripper.

'I wish I could be a fly on the wall at that party,' I thought. 'I'd be masturbating over watching my mother, aunt, grandmother, and their five friends having sex with a stripper.'

Something that I'd do for free, this lucky son-of-a-bitch was going to expose his erect, naked prick to all of the women who I'd love to flash them my erect, naked prick. No doubt, as male strippers do, he'd be making out with the women. With them not slapping his hands away, stopping him, and/or admonishing him, he'd be feeling them through their clothes while continuing to expose his big dick to them.

Not stopping there, he'd be sticking his big dick in their hands. Instead of pushing him away, they'd be wrapping their manicured fingers around his stiff cock and taking his erect prick in their hands while stroking him. Undoubtedly, determined to make him cum all over their hands, all over their faces, or across their naked breasts, they'd be stroking him faster and harder while laughing and having a good time.

Again, with them not pushing him away, he'd be sticking his erect cock in their mouths. While putting a gentle hand to the back of their pretty heads, he'd be humping their mouths. He'd be fucking their faces. Determined for him to cum in their mouths, they'd continue to stroke him faster and harder while sucking him deeper.

Again, with them not stopping him, continuing to sexually assault them, something that I yearned to do, he'd be sticking his hand down inside of their blouses and bras. He'd be touching, feeling, and fondling their naked breasts while fingering their erect nipples. He'd be doing everything that I wished that I could do to them and with them.

Still not stopping there, he'd be feeling and squeezing their asses through their clothes. He'd be reaching beneath their skirts to cup their pussies through their panties. For those women who allowed him to have his way with them, he'd be removing their panties, bending them forward, and fucking them from behind, too.

# # #

I wouldn't have known that my mother had hired a stripper for her sister's birthday party until he called at the last minute and cancelled. He said something about double booking and being out of town on that day. He said that he already reversed the charge on her credit card and refunded her deposit. With our impromptu gathering just a small and intimate house party of eight women, no doubt, he received a better offer with more women and for more money.

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