Never Have I Ever
Never have I ever had incestuous sex with my mother.
Looking back over more than 30-years of regrets, Michael is full of regrets, sexual regrets, and especially incestuous, sexual regrets for things that he wished he had done but didn’t have the nerve to do.
Instead of being afraid, Michael wished he had done more things, especially sexually, incestuous things that he was sexually tempted and sexually teased to do but was unable to bring himself to do them with his MILF of a 48-year-old, mother, Irene. Sexually teasing him, whenever wearing her low-cut blouses, his mother always deliberately flashed him down blouse peeks of her bra clad breasts and her long line of sexy cleavage. Whenever wearing her sexy, low-cut nightgowns, she deliberately flashed him down-nightgown views of her double D cup, naked breasts and erect nipples.
Regretting that he didn’t return the sexual, exhibitionist favor and flashed his mother his naked prick, while kissing her and making out with her, he wished he had touched and felt her breasts through her blouse and bra. Looking back in hindsight, he wished he had stuck his horny hand down her nightgown top to feel her naked breasts and finger her erect nipples and put her soft, warm hand on his naked, erect prick. He wished he had touched and felt all that his mother deliberately flashed him of her bra clad and naked breasts.
When wearing her short skirts, she sat across from him while watching TV. With her always slowly and seductively crossing and uncrossing her long and shapely legs in the way that Sharon Stone did in Basic Instinct, she continually flashed him up-skirt peeks of her white, bikini panties. When wearing her short, sheer, and sexy nightgowns and, again, with her sitting across from him while watching TV, she always sat across from him while drinking her coffee. With her knees parted just enough for him to see her naked pussy, she flashed him up nightgown views of her naked cunt.
Always masturbating over all he had seen of his mother’s nearly naked and naked body; when wearing her short skirts, he lost count of how many times she flashed him her panty clad pussy. When wearing her low-cut blouses, he lost count of how many times she flashed him her bra clad breasts. When wearing her low-cut nightgowns, he lost count of how many times she flashed him her naked breasts. Again, when wearing her short nightgowns, he lost count of how many times she flashed him her naked pussy.
Whether her sexual flashes were deliberately done or unintentionally happened, in the way that she looked at him with horniness, incestuous desire, and sexual lust, his mother clearly wanted to have sex with him. While waiting for him to make his sexual move to seduce her and to have sex with her, his biggest regret, he regretted not having had sex with his MILF of a mother, Irene. Something that all sons imagine doing, always imagining her naked and her having sex with him, what son doesn’t imagine his mother without her clothes and having sex with her while masturbating himself?
What son doesn’t imagine making out with his mother while feeling her beautiful body through her clothes? What son doesn’t imagine French kissing his MILF of a mother while making slow, passionate love to her? What son doesn’t imagine bending his mother over a table, lifting the back of her nightgown, and fucking her fast enough and hard enough to give her a sexual orgasm with his erect cock? Too late now with her dead and buried and him praying over her grave, he looked back over his life of more than 30-years of sexual regrets.
‘Alas, if only I could go back thirty years, with her deliberately flashing me and sexually teasing me, I would have touched and felt my mother through her clothes while making out with her. I would have stuck my hand down the front of her nightgown to fondle her naked breasts and finger her erect nipples. I would have stuck my horny hand up the back of her nightgown to feel and squeeze her shapely, naked ass,’ he thought.
He regretted not having incestuous sex with his mother.
‘I should have stripped her naked, bent her over the sofa and fucked her. I should have fucked my mother,’ he thought. ‘I wish I had fucked my mother.’
Would have, could have, and should have, with him having so many sexual opportunities that turned to incestuous regrets, he didn’t sexually do anything with his mother. He wished he had taken his MILF of a mother up on her sexual invitations and had incestuous sex with her. He wondered what it would have been like to make out with her while touching and feeling her everywhere through her clothes. He wondered what it would have been like to have slowly stripped his mother naked while having incestuous sex with her beautiful body.
‘Fuck me, Michael. Fuck your mother. Fuck me faster. Fuck me harder. I’m going to cum. Mommy is going to cum,’ he imagined his mother saying while he was on top of her and humping her fast and hard enough to give her a sexual orgasm with his erect prick. ‘Don’t stop humping me. Don’t stop fucking me. I’m going to cum, Michael. I’m going to cum,’ he imagined his mother saying. “Mommy is going to cum.”
Regretting not doing any of it, he wondered what it would have been like for his mother to blow him. He imagined staring down at his mother as she stared up at him with his erect cock in her in her hand before taking him in her mouth. He would have loved for her to have stroked his cock while sucking his prick. Even now, regretting not having had oral sex with her, he would have loved to have ejaculated a load of cum in his mother’s mouth and all over her pretty face and big, naked breasts.
“Oh, Michael. You gave mommy quite the cum bath,” he imagined her say with her face dripping with cum.
Imagining her dripping with cum, from her hair, her nose, her chin, and her breasts, he would have loved to have given his mother a cum bath. After cumming in her mouth, once she removed his cock from her lips, he would have love to ejaculate a second load of cum all over her face, in her dark brown hair, and across her big, naked breasts. Dominating her in every sexual way, he would have love to have made her his sexy bitch, his nasty whore, and his sexual slave.
‘Take off your nightgown. Get on your bed on your back and spread your legs,’ he imagined saying while mounting his naked mother. ‘Now, fuck me. Fuck your son as if I’m your husband, your boyfriend, or your lover,’ he imagined ordering his mother.
# # #
Author’s Note:
Inspired by the thought of the nonsensical line of never have I ever, this is a true story that Michael asked me to write about his laundry list of incestuously, sexual regrets. More than thirty-years later, he still masturbated himself over imagining having had sex with all of those women that he now regretted not having sex with. He wished he had acted upon their sexual desires to want to have sex with him.
Kicking himself for not giving into the sexual opportunities that passed him by, he wondered how different his life would have been had he given into the sexual temptations that they offered him. In hindsight, when them sexually teasing him and deliberately flashing him, he would have had incestuous sex with not only his MILF of a mother but with his sexy, whore of a sister. With her sexually teasing him and deliberately flashing him too, he would have had sex with his mother’s younger sister, his MILF of an aunt, Maureen.
# # #
Never have I ever had incestuous sex with my mother.
My biggest regret, never have I ever had incestuous sex with my mother, when clearly, I easily could have had incestuous sex with my MILF of a mother. Even though I wanted to and dared myself to have sex with her, never have I ever had incestuous sex with my mother. Even though she mercilessly, sexually teased me by wearing her low-cut, short, sheer, and sexy nightgowns with nothing underneath and without wearing a robe over them, I never reached out and touched her and felt her through her sexually revealing nightgowns.
‘Making my incestuous, sexual intentions known, I wish I had felt my mother’s big tits through her nightgown,’ he thought. ‘I wished I had lifted up the front of her nightgown to cup her bushy, black pussy. I wished I had lifted up the back of her nightgown to feel and squeeze her naked ass. In the way that she deliberately exposed her nearly naked and naked body to me, I wished I had exposed my erect, naked prick to my mother,’ thought Michael.
He remembered his mother continually sexually teasing him and deliberately exposing her nearly naked and naked body to him.
‘Regretting that I didn’t, I wished I had fondled her nearly naked body through her sheer and sexy, low-cut nightgowns while kissing her and making out with her. At the very least, when she wore her sexiest nightgowns around me, I wished I had hugged her. I wished I had rubbed my semi-erect cock against her nightgown clad tummy. I wished I had dropped my hand down the back of her to feel her shapely, nearly naked ass,’ he thought.
Afraid to ask if he could, he always wanted to sleep in his mother’s bed.
Curious as to what she would have said if he had made an incestuous, sexual move on his mother, I wished I had asked my mother if I could have slept with her. With my semi-erect prick pressed against her shapely ass, I would have loved to have held her, cuddled her, and spooned her. Then, as soon as she fell asleep, I imagined lifting the back of her short nightgown to expose her naked ass. Finally, reaching over her, I imagined feeling her big breasts through her nightgown before sticking my horny hand down her open, nightgown top,’ he thought.
Too late, now that he had the courage and the will to do all that he incestuously, sexually wanted to do with his mother, would have, should have, and could have, she was dead and buried.
# # #
‘In hindsight, realizing that she had encouraged me to do so by her sexual looks and incestuous actions, I wished I had reached up and felt her big breasts through her nightgown while fingering her erect nipples,’ he thought. ‘I wonder if she would had continued to allow me to feel her nearly naked breasts or if she would have slapped my hand away. If she didn’t slap my hand away, I would have love to have inserted my hand down the top of my mother’s low-cut nightgown and felt and fondled her naked breasts while pulling, turning, and twisting her erect nipples,’ he thought.
Even though I could clearly see everything through her sheer and sexy nightgowns, her naked ass, her naked bushy, black pussy, her huge double D cup, naked breasts, and her big, erect nipples, unable to act, I just stared. I stared at all that I was seeing and all that she was showing. I stared at all of that I’d be masturbating over later. Regretting not doing more than just staring, the most that I ever did was to masturbate myself over all that I could see of my mother’s nearly naked body while allowing her to catch me masturbating.
Deliberately allowing her to catch me masturbating over imagining her naked and having incestuous sex with her, I masturbated every morning and every evening behind my closed, bedroom door. Whenever my horny mood struck, I’d masturbate again over imagining my mother naked and having sex with her. Instead of doing what I had sexually wanted to do with my mother, I masturbated four and five times a day while imagining having incestuous sex with her. While masturbating myself, I laid back on my bed naked while waiting for her to barge in my bedroom without knocking to delivery my laundry.
Vicariously sharing my sexual thoughts with her, when I knew she was standing outside of my bedroom door ready to burst in without knocking, I started my sexual monologue. I talked loud enough for her to hear me through my closed bedroom door while giving a verbal masturbation monologue of all that I wanted to do to her shapely, naked body. I wanted her to hear me so that she’d open my bedroom door and catch me naked and stroking my erect prick. I wanted her to catch me masturbating myself. I wanted her to catch me cumming all over myself.
Hoping that she’d barge in my bedroom without knocking to deliver my laundry, which she had a habit of doing, I deliberately walked around my bedroom naked with a huge erection. Hoping my mother would catch me naked, I wanted her to see my erect, naked prick. Moreover, wanting her to know that I was masturbating over her, whenever I masturbated, I wore headphones and closed my eyes as I stroked myself and while wishing she’d open my bedroom door. When she did open my bedroom door, I pretended that I didn’t know that she was in my bedroom watching me masturbating myself.
Whenever I heard her walking down the hall towards my bedroom, and saw the shadow of her feet beneath my bedroom door, I started my verbal monologue show for her sexual benefit. Instead of opening my bedroom door and barging in without knocking, she stood outside of my bedroom door listening to all that I was sexually saying about her. Talking loud enough for her to hear, I wanted her to hear all that I had to say through my closed, bedroom door. Holding nothing back, I gave her an entire monologue of my sexual, incestuous thoughts while masturbating myself over my mother.
# # #
“Oh, Mom, the highlight of my horny days, I love walking by your bedroom when you’re dressing and undressing with your bedroom light on and your bedroom door wide open. With you making no move to close your bedroom door and/or to cover nakedness, I love seeing you in your sexy, bikini panties and in your low-cut bra. I love seeing you topless. I love seeing your big, naked tits and erect nipples. I love seeing you naked. I love seeing your naked, shapely ass and your bushy, black pussy,” I said loud enough for my mother to hear.
When I saw her shadow beneath my bedroom door and knew that she was still standing there listening, I continued my sexual, masturbation monologue.
“Whenever I see you naked, I love seeing your shapely ass and your bushy, black pussy. I love seeing you naked. I love seeing your big, shapely, double D cup breasts. You have such big tits and I wish I could touch them, feel them, and fondle them while sucking your erect nipples,” I said while stroking myself faster and harder. “I wish I could feel and squeeze your shapely, naked ass. I wish I could cup your bushy, black pussy in my horny hand. I wish I could rub your swollen clit and finger fuck your pussy. I wish I could masturbate you, mother.”
After she clearly heard me say that I loved seeing her in her bra and panties, topless, and naked, the very next day when I walked by her room, she was still in bed. Hoping to see something that I shouldn’t see, with her reading in bed, I stepped in her bedroom to talk to her. Surprising me and never expecting her to do what she did, she pushed back the covers and spread her bent knees to climb out of bed. With her nightgown already up to her waist, and her legs parted wide open, she flashed me her black, bushy, naked pussy while getting out of bed.
‘I can’t believe I saw my mother’s pussy,’ I thought. ‘I can’t believe she deliberately or unintentionally flashed me her naked cunt. Wishing that I had reached out and touched her and cupped her naked pussy in my hand, I regretted not fingering my mother’s pussy. I regretted not rubbing her naked clit and finger fucking her pussy. I regretted not moving between her shapely legs to finger her pussy while licking her cunt. Nonetheless, I’ll be masturbating over seeing my mother’s naked cunt for the rest of my life,’ I thought.
Then, with her not done sexually teasing me and flashing me, she shocked me with what she did next. Not wasting a second in her exhibitionism of her naked body, she stood, reached down for the hem of her nightgown and lifted her nightgown up and over her head. As if waiting for me to touch her and feel her naked body, she stood there staring at me while I stared at her.
‘My mother is naked,’ I thought. ‘I can’t believe my mother stripped herself naked in front of me.’
She continued staring at me as if to see my reaction to seeing her naked. Shocked, I couldn’t believe my eyes. Not two feet away from her, my mother was naked. Hard for me to wrap my brain around seeing my mother without her clothes, I couldn’t believe she was naked. Stunned, I couldn’t believe that I was seeing my MILF of a mother totally naked.
Continuing to stare at her beautiful, 48-year-old, naked body without leaving her bedroom, I couldn’t believe that I was seeing her big, naked tits and her fully, erect nipples. I couldn’t believe that I was seeing her bushy, black pussy, and her naked, shapely ass. I couldn’t believe that I was seeing my MILF of a mother without her clothes. Yet, more than that, I couldn’t believe that my mother made no move of modesty to cover her naked breasts with her forearm and/or her naked pussy with her hand. Instead, as if she was fully dressed, she stood before me naked.
Instead of covering her naked breasts with her forearm and covering her naked pussy with her hand, with her wanting me to see her naked, she stood there with her arms by her side. As if daring me to look, indeed, she wanted me to see her naked as much as I wanted to see her naked. Totally stunned, all that I could do was to stare at my mother’s big, naked breasts, her erect nipples, her black, bushy pussy, and when she turned and bent at the waist to get dresses, at her naked ass.
‘Wow! I can’t believe she removed her nightgown in front of me. I can’t believe my mother stripped herself naked. I never thought I’d be seeing my mother naked, totally naked,’ I thought. ‘I can’t wait to masturbate over my naked mother,’ I thought. ‘I can’t wait to masturbate over her big, naked tits, over her bushy, black pussy, and over her shapely, naked ass.’
# # #
Still sexually reeling over that day when my mother stripped herself naked in front of me, whenever I masturbated myself, I thought of that day when my mother removed her nightgown in front of me. With me continually masturbating over seeing my mother naked, I’ll never forget that day for as long as I live when my mother stripped herself naked. Kicking myself for not touching her and feeling her naked body everywhere that a son should never touch and feel his mother, she stood there as if waiting for me to touch her but I didn’t.
Now, regretting that I didn’t reach out to touch her, I wished that I had felt and fondled her naked body everywhere. Regretting that I didn’t touch her and feel her, I wondered if she would have allowed me to touch her and feel her. I wondered if she would have allowed me to feel and fondle her naked body. I wondered if she would have allowed me to have my wicked, sexual way with her big tits while pulling, turning, twisting, and sucking her erect nipples.
Something that I’ll never know, if I had dared to touch and feel her, I wondered if she would have slapped my hand away and/or slapped my face for sexually abusing her naked body or allowed me to continue. I paused stroking my cock to see if my mother was still standing in front of my bedroom door listening to all that I was saying. Still seeing her feet beneath my bedroom door, when I saw that she was still there, I was glad that she was still there listening to me masturbating myself.
Once I saw that she was still there listening, pleased that I had sexually aroused my mother enough for her to remain at my bedroom door, I continued my masturbation monologue. I wanted her to hear everything. I wanted her to know how much I sexually wanted her. I wanted her to know that not only was I masturbating over imagining her naked but also, I masturbated over imagining her having incestuous sex with me.
“I wish I could play with your pussy and masturbate you, mother. Wishing I could give you a sexual orgasm, I’d love to watch and hear you cum. I wish I could eat your beautiful, black pussy, mother. I’d love to lick your pussy while rubbing your swollen clit and finger fucking your pussy. I’d love to eat your pussy while reaching up to feel your big, naked tits and finger your erect nipples,” I said loud enough for her to hear.
Not stopping there with her still standing in front of my closed, bedroom door listening, I continued my masturbation monologue.
“I wish I could make passionate love to you before fucking you fast enough and hard enough to give you a sexual orgasm with my cock. I wish I could cum in your pussy, mother. Too bad that you can no longer have children, I wish I could make you pregnant. I wish I could give you my baby. I wish I could give you multiple sexual orgasms with my fingers, my tongue, and my cock. I really want to fuck you mother. I really want to pound your pussy. I really want explode a load of warm cum in your cunt.”
I paused again to see if my mother was still there listening. I couldn’t believe my mother was still standing in front of my bedroom door listening to me masturbate myself. When I saw that she was still standing in front of my bedroom door, emboldened to brazenly say even more, I continued with my masturbation monologue.
“I wish you would wrap your long, manicured fingers around my stiff prick and have you stroke my cock,” I said. “I’d love for you to masturbate me, mother. I’d love to cum for you. I’d love to cum all over you. I’d love to give you a cum bath.”
Then, wondering if she sucked cock, I said what I wanted to hear and hoped she’d do.
“Not stopping with just masturbating me, I wish you would blow me. I wish you would suck my cock and allow me to cum in your beautiful mouth,” I said. “I’d love to cum in your mouth, mother.”
Suddenly, I imagined my big dick in my mother’s mouth while she stared up at me with her big, brown eyes. Determined to cum in her mouth, my mother’s mouth, I imagined her stroking me faster and harder while sucking me deeper. Indeed, glad that my mother sucked cock because I imagined her giving me the best blowjob of my life.
“I’d love for you to suck my cock, mother. I’d love to look down and see you with my stiff prick in my mouth while you stared up at me. I’d love to cum in your beautiful mouth, all over your pretty face, and across your big, naked breasts. I’d love to cover you with cum,” I said. “I’d love to see you dripping with cum. I’d love to give you a cum bath, mother.”
# # #
After hearing all that I said and all of what I sexually wanted to do to her naked body, I wondered what my mother was thinking. Wishing I had a hidden camera outside of my bedroom door, I wondered if she was touching herself while listening to me masturbating myself. I wondered if I had made her as sexually aroused as I was sexually excited. Something that I never saw or heard her doing, I wondered if she masturbated. With me masturbating every day, multiple times a day, I’d love to watch my mother masturbate herself to me masturbating myself.
Just as I thought that, pretending that she had just arrived and didn’t hear a word that I had said about all that I sexually wanted to do to her, she burst open my bedroom door without knocking to deliver my laundry. Sitting in my computer chair with my headphones on and my eyes closed, opening my eyes a crack, just enough to see her, I saw my mother staring at my erect prick. With her seemingly enamored with my naked cock, masturbating myself for my mother, I continued holding my erect prick in my hand while stroking myself.
I pretended that I didn’t know she was standing in my bedroom by my opened bedroom door and staring at my naked cock while watching me masturbate myself. Determined to cum for my mother, I stroked myself faster. I stroked myself harder. As if it wasn’t enough that I was showing her my naked, erect cock, I wanted her to watch me masturbating myself. I wanted her to see me cum. I wanted her to hear me cum.
‘My mother is staring at my naked prick in the way that I stared at her naked body. I can’t believe my mother is still staring at my naked cock,’ I thought. ‘Seemingly, my mother is as sexually aroused as I’m sexually excited. I can’t believe my mother is staring at my erect, naked prick as if she wanted to stroke it, suck it, and fuck it. I can’t wait to masturbate later over my mother staring at my naked dick.’
Instead of leaving, standing in front of and leaning against my closed, closet door, she remained there watching me stroking myself faster and harder. Determined to cum for my mother, I wanted to cum for her. I needed to cum for her. While imagining that I was cumming on her, I wanted her to see and hear me ejaculate a load of cum all over my naked body.
Hoping that she’d walk over to me, move to her knees, and take me in her hand before taking me in her mouth, I’d love for my mother to blow me. I’d love for my mother to stroke my cock while sucking my cock. I wished my mother would suck my cock and allow me to cum in her mouth. Only, she didn’t do that and I regretted that I didn’t ask her to do that. I wondered if I put a gentle hand to her shoulder and asked her to blow me if she would have given me oral sex.
‘Mom, suck my cock. Blow me, mother. Please blow me,’ I imagined saying to my mother. ‘I need to cum in your mouth while fondling your naked breasts and pulling, turning, and twisting your erect nipples.’
I regretted that I didn’t take her by her hand, pull her to me, and put her hand on my erect prick. I regretted that I didn’t wrap her long, manicured fingers around my dick and move her hand up and down with my hand for her to give me a forced hand job. I regretted that I didn’t put a gentle hand to her shoulder in the hope that she would have taken the not-so-subtle hint. Perhaps, then, she would have moved to her knees. Perhaps, then, she would have taken me in her mouth, sucked my prick, and allowed me to cum in her mouth.
Instead, of touching me, what she did was to touch herself. After she put her laundry basket down on my chair, while still standing in my room, she continued watching me masturbate myself. I watched her through my barely opened eye slits. Something that I never expected her to do, in the way that I wished I could do, she fondled her big breasts through her nightgown while fingering her erect nipples. Then, surprising me, she reached her hand in her low-cut nightgown and pulled out her naked breasts.
‘Fuck me. Oh, my God. I can’t believe my mother pulled her naked breasts out of the top of her nightgown,’ I thought. ‘I can’t believe she’s feeling and fondling her naked tits while fingering her erect nipples.’
She continued fondling her naked tits while watching me stroke myself faster and harder. I couldn’t believe I was seeing my mother’s naked breasts. I couldn’t believe my mother was fondling her naked tits while watching me masturbating myself. Surprisingly, with her nipples totally erect, my mother was as sexually aroused as I was sexually excited.
Finally, further surprising me, not believing my eyes, she lifted the hem of her nightgown to her tummy and exposed her black, bushy, naked pussy. While she continued staring at me masturbating myself and continued staring at my naked cock, she rubbed her clit while finger fucking her pussy. Shocking but true, my mother masturbated herself to me masturbating myself. Then, as soon as I shot a load of cum all over my chest and stomach, as if she was embarrassed or sexually aroused, and not wanting me to catch her in my room masturbating herself, she abruptly left my bedroom.
# # #
Greeting the day, something that I looked forward to seeing every morning, my mother would push open the drapes and allow the sun to light up her sheer and thin nightgown as if she was naked. As if she was walking through a TSA, X-ray machine at the airport, I could clearly see through her sexy nightgowns. I could clearly see my mother’s naked ass. Then, when she turned to face me, with the bright light beaming in behind her and lighting her up in silhouette, I could clearly see her bushy, black pussy and her huge, naked breasts.
Then, every morning, whether unintentionally or deliberately, she gave me a down-nightgown view of her big, naked breasts. She’d lean over me while serving me food or pouring me coffee. While drinking her coffee and watching TV, deliberately or unintentionally exposing herself to me, she’d sit across from me with her knees parted just enough to give me an up-nightgown view of her black, bushy pussy. Every morning I saw my mother’s naked breasts and her naked pussy. Every morning, for all intents and purposes, with her giving me an erection, I saw my mother as if she was naked.
Remembering back more than 30-years-ago when I was a horny, twenty-something-year-old, testosterone filled, young man, deliberately allowing me to see her in her bra and panties, topless, and/or naked my mother would dress and undress with her bedroom door open. I lost count how many times I saw my mother in her sexy, low-cut bra and white bikini panties. I lost count how many times I saw my mother topless. I lost count how many times I saw my mother’s naked ass, her naked pussy, and her naked tits. I lost count how many times I saw my mother naked.
Stunned and sexually aroused, all that I could do was to stare. Regretting not doing more than just staring at all that I was seeing of her beautiful, lingerie clad, topless, and/or naked body, I wished I had touched her and felt her. I wished I had asked if I could sleep with her in her bed while holding her, cuddling her, and spooning her. I wished I had touched and felt her while she was sleeping.
I wished I had asked her if I could wash her back while she took a bath. While washing her back, I would have love to have reached around her to feel her naked breasts. Then, dropping the soap numerous times, I imagined brushing my horny hand by her naked pussy. I imagined feeling her naked ass with the excuse of looking for the soap.
Something I regretted not doing, with her stripping herself naked in front of me, I wished I had asked her to masturbate me while I masturbated her. I wished I had asked her to blow me and allow me to cum in her mouth. Filled with and consumed by so many sexually, incestuous regrets, I wished I had fucked my mother. I wished I had ejaculated a load of cum not only in her beautiful mouth but also in her beautiful pussy, too.
# # #
Every summer, with her thinking that I wasn’t home, and with her outback in the backyard sunning herself topless, I’d sneak in the front door and up to my bedroom. My bedroom window overlooked the backyard and I could clearly see my mother topless and, sometimes, even naked. Unembarrassed and unashamed, she deliberately gave our neighbors, the lawn guys, and the pool men views of her topless and naked body.
‘My mother is such an exhibitionist whore,’ I thought. ‘As if pretending that we were at a nude beach, I dared myself to go out to the backyard naked. Regretting that I didn’t, I never went out to the backyard naked.’
Daring myself to do so but never having the nerve to ask her, I wanted to ask her to go with me to a nude beach. I’d love to spend the day naked with my naked mother. I’d love to hold her and sexually touch her while wading in the water. Regretting not asking her to go to a nude beach with me, with her always flashing me her naked and nearly naked body, I always wondered if she’d go to clothing optional beach with me.
‘How sexually exciting would that be to go to a nude beach with my mother,’ I thought?
I would have loved for a multitude of men to see my mother naked. I would have loved to have a small crowd of men gathered around us to watch us having sex on the beach. I would have loved for few men to masturbate and cum all over my mother’s face and her naked body. I would have loved to have watched my mother stroke, suck, and fuck a couple of their pricks.
Another thing that I regretted not doing. I always wanted to play strip poker with my mother. I imagined us drinking wine and the both naked while playing cards. Once we removed our clothes, I imagined all of the sexually, incestuous things that I asked her to do now that we were naked.
Finally, I always wanted to photograph my mother in her bra and panties, topless, and/or naked. I always wanted to show her underwear clad, topless, and/or naked photos to my friends. Moreover, something I knew she’d never allow me to do, wanting all of her relatives, friends, and co-workers to see her naked, I always wanted to post her naked photos and videos online.
Last but not least, something that most men did with their wives or girlfriends, I wanted to ask my mother if she’d have swinging sex with other couples. Only, not wanting her to think that I was a deranged pervert, I never found the nerve to ask my mother to have swinging sex with me and with other couples. How hot would that be to go to swingers’ parties with my mother?
I would have loved to have watched my mother having sex with another couple. I would have loved to have watched her having sex with another man while stroking him, sucking him, and fucking him. I would have loved to have watched her having sex with another woman.
I would have loved to watch my mother making out with a woman. I would have loved watching her masturbate and eat another woman’s pussy. I would have loved watching another woman masturbate and eat my mother.
# # #
Never have I ever had incestuous sex with my 26-year-old sister, Kathy.
After having taken her shower, my sister, Kathy, was always walking around me while wearing nothing more than a towel wrapped around her sexy and shapely body. Sometimes, when she reached over her head while drying her hair, her towel would slowly slide down to expose her naked breasts. I couldn’t believe that I was seeing my big sister’s big, shapely, naked breasts. In the way that I stared at my mother’s big, naked tits, I stared at my sister’s big, naked tits.
‘I saw my big sister’s naked breasts,’ I thought. ‘If it wasn’t enough that I saw my mother’s naked tits, I can’t believe I saw my sister’s naked tits, too.’
Sometimes, before she could grab it, her towel would slide all the way down to her feet and allow me to see her naked.
‘I saw my sister naked. If it wasn’t enough that I saw my MILF of a mother naked, I can’t believe that I saw my big, sister naked, too,’ I thought. ‘In the way that I’ll be masturbating over my naked mother for the rest of my life, I’ll be masturbating over my naked sister for the rest of my life, too.’
While standing in the open bathroom doorway and watching her drying her hair, seemingly, not deliberate on her part by completely accidental, I just happened to be at the right place in the right time.
“Oh, my God, Michael,” she said while seeing me staring at her naked breasts through the bathroom mirror. “Stop staring at my naked tits. Stop staring at my naked body. Matter of fact, get out of my bathroom. Get out! Go! God, I’m your sister and not some whore that you invited home from the bar. You’re such a nasty pervert,” she said. “I can’t believe that you sexually lust over your sister, you pig.”
# # #
Then, there were all of those times when she came home drunk. Immediately stripping off her clothes, she’d lay on her bed naked with her bedroom door wide open. I lost count how many times I saw my sister drunk and naked. I lost count how many times I masturbated over my sister’s naked breasts, her naked, blonde trimmed pussy, and her naked ass. In the way that I did with my MILF of a mother, I lost count of how many times that I masturbated over my sexy sister.
With her soundly sleeping, regretting that I didn’t, I was tempted to walk in her bedroom and stand beside her while touching and feeling her naked body everywhere. I was tempted to wrap her long, manicured fingers around my erect prick. I was tempted to move my hips back and forth while holding her hand in place to give me a forced hand job. I so wanted to cum all over my sleeping sister. I so wanted to give her a cum bath. Only, regretting that I didn’t, I never had her give me a forced hand job nor did I ever cum in my sleeping, drunken sister.
Nonetheless whether I had drunken, sleeping sex with my sister, not stopping with just a hand job, I was tempted to slowly slide my erect, naked prick across my sister’s partially opened lips. I wondered if she’d take me in her mouth and blow me but I never did. Regretting that I didn’t stick my erect prick in my sister’s drunken and sleeping mouth, whether sleeping or awake, I would have loved for my sister to blow me. I would have loved to cum in my sister’s sleeping, drunken mouth.
Not stopping with a mere hand job or a blowjob, I was tempted to mount my sister and fuck her in her drunken sleep. Yet, it was enough that I was seeing her without her clothes. Still, I so wanted to touch and feel her big breasts while fingering her erect nipples. Only, afraid of awakening her, I so wanted my drunken and sleeping sister to stroke me, suck me, and fuck me.
Then, thinking what worked for my mother may work for my sister. Whenever I was home alone with her, I’d go to my room and masturbate myself. Knowing my sister had the same habit as my mother, instead of knocking on my bedroom door, she’d barge in as if my bedroom was her bedroom.
When hearing my sister climbing the stairs and walking down the hall towards my room, I’d quickly strip myself naked. Then, as I did with my mother, I donned my headphones and closed my eyes while stroking my erect prick. As soon as I heard her standing outside of my bedroom door and saw her feet beneath my door, I’d start my verbal, masturbation monologue.
“Oh, Kathy, I’d love to play with your pussy while sucking your big tits. I’d love to give you a sexual orgasm with my fingers and masturbate you. I’d love to stick my erect cock in your mouth,” I said plenty loud enough for her to hear through my closed, bedroom door. “I’d love to cum in your mouth while feeling and fondling your naked breasts.”
Then, when she opened my bedroom door, I slit opened my eyes just enough for to see her standing in the doorway while staring at my erect, naked prick. In the way that my mother touched her breasts through her thin nightgown, my sister fondled her breasts and fingered her nipples through her sexy nightgowns, too. Clearly, in the way that I was sexually excited and had sexually aroused my MILF of a mother, I had sexually aroused my sexy sister, too.
I always regretted not standing and walking to my sister naked. I always regretted not sticking my erect prick in her soft hand while fondling her breasts through her nightgown. I always regretted not bending my sister over my bed and fucking her. As much as I would have loved to cum in her mouth, I would have loved to cum all over her naked ass. In the way that I wished I had given my mother a cum bath, I regretted not giving my sister a cum bath, too.
# # #
Never have I ever had incestuous sex with my mother’s sister, my aunt Maureen.
Whenever my 42-year-old aunt came for a visit, especially when my mother wasn’t there in the room with us, she’d sexually tease me by flashing me some part of her naked body. Whether flashing me her naked breasts, her naked ass, and/or her naked pussy, she continually flashed herself to me while making her flashing look accidental.
When dressing and undressing, she had the same habit as my mother. She’d dress and undress with the guest bedroom door wide open. Daring myself to touch her and feel her but regretting that I hadn’t, I’d stand in her bedroom doorway talking to her while watching her dress or undress. Unembarrassed and unashamed, not covering her naked breasts with her forearm or her naked pussy with her hand, instead, she’d turn to face me while she was naked.
“You have beautiful body, auntie,” I said. “I love your shapely ass and your big breasts.”
She laughed while looking down at herself before looking at me.
“You may touch me and feel me if you’d like,” she said.
Only, turning red with embarrassment and shame, I never took my aunt up on her incestuously, sexual offer to touch and feel her naked body. In the way that I regretted not sexually touching and feeling my naked mother and naked sister, I’ve always regretted not touching and feeling my naked aunt.
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