Sissy Son

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A Mom and Son learn about themselves and each other.
2.1k words
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Jane tried to stop, she knew it was wrong but she couldn't help herself. The sounds were quite obvious, from his bedroom her son Tom was masturbating. He clearly believed the house was empty but his mother had simply gone to the store. Now she stood at his bedroom door, the groceries at her feet as she began to allow long suppressed physical need to grow inside her.

Was it the thought of her 18 year old son or was it simply the idea of any man in her house able to show his verility that made her slowly press the heal of her hand into the crotch of her demin shorts? Now in this unguarded moment she admitted to herself that her sons developing maturity had not gone unnoticed but she also understood that a man in her life would have stopped things from going any further.

The intense sounds of a man in the throws of arousal drove Jane on without regard to decency, as her son moaned out his pleasure she unified his orgasmic euphoria with her own and swiftly unbuttoned her shorts to gain access to the more yielding soft cotton of her briefs. She was already wet as she had been in so many inappropriate moments before, she was only 40 years old and could not deny her own womanhood.

With her sons pleasure building she slid her fingers inside that damp cotton brief and felt the wetness of her yielding pussy. She could not believe how much her body ached for pleasure no matter where it came from even her own son but as her fingers slid inside her she knew that no matter what she needed the rampant cock that lay behind that door.

With an awareness but with reckless abandon Jane pulled her shorts from her legs and pushed through her sons bedroom door with an indescribable, choking, cocktail of certainty and terror. She could never have anticipated the sight that fell before her. On her sons bed lay Tom his fist pumping upon his hard, youthful cock but his body was regailed in her underwear, his mother's underwear, stockings, suspender belt, French knickers and bra.

Who was more astounded at that moment would be impossible to say. Tom saw his mother half undressed before him as he lay before her displaying his hardened masculinity framed within the femininity of his own mother's delicate silken intimate panties.

Neither spoke for what seemed like forever. Before Tom could complete the word "mom" his mother unleashed on him. "You filthy little sissy, I can't believe you". She swirled about where she stood unable to comprehend how a moment so daring, one she had instigated had gone so wrong. Jane ripped her shirt open, buttons flying, now she bared her bra and panties and the beautiful contours of her soft belly. "I was going to give myself to you, do you understand me, I wanted you to have your mother, to give you want you needed" Tom was stunned, what was she saying, what the hell had happened to his lovely mom.

"Mom, please, I'm sorry, can't we just talk" Tom pleaded.

"Oh no, no talking, if you're gonna be a sissy you're gonna get fucked like one.

If her very essence had ever been shaken like this then Jane could not remember. With a flurry of intense anger and arousal she scanned her sons room. Grabbing a scarf and a belt she wrenched Tom's wrists as he lay hopelessly disturbed on the bed and dragged him with a strength she never knew she had onto his stomach and hauled his hands up to the bed posts. Tom hardly resisted as he vainly pleaded for his mother's understanding. It was no use. Soon his wrists were tied to the bed, his face down in his pillows. He could no longer see what was happening but sensed his mother had left the room, he was right, but he could not have imagined what was in store for him on her return.

Tom was pulled by his hair, his head raised and now he saw his mother totally naked. She was everything he had wanted, curvy yet trim, wonderfully gentle, firm breasts, the broad hips of a real woman and a beautifully sculpted patch of dark public hair. But he could not see what lay at the apex of her tidy little snatch because instead of the arousing beauty of her womanhood all Tom could see was the bulbous projectile of a rubber penis that was strapped firmly about his mother's hips. Still with her hand gripped to her sons hair Jane pulled Tom's head up, "You like being a girl? Then suck cock you little bitch"

Without a moments hesitation Jane had drove her strap on into her sons gaping, disbelieving mouth. Tom gagged instantly, drooling and choking on his mom's rubber cock and has Jane looked down on her sons startled face taking her thick false cock in his throat she felt waves of euphoria and revulsion that drove her to the point of an emotional conflict she simply could not withstand.

As Tom gasped for breath he discovered that he had barely reached a point of mental and physical shock, for now his gorgeous mother who had revealed to him her willingness to give her lustful body to him, now had discovered his fetish for her underwear, who had force fed him her strap on dildo now began to pour lube down the crevice of his arse and started to press oily fingers against the puckered rim of her son anus.

Tom gasped, the opportunity was taken by his mother and she took the very pair of small cotton briefs that she had begun masturbating in to the sound of her sons pleasure and shoved them in his mouth. Tom choked, his stomach contracting, but his most powerful sensation was the smell of his mom's sex on the warm wet cotton. He tasted her and smelt her for the first time and despite fear and panic he began to feel his cock twitch in to life once more for the first time since shock had overcome him.

His young member stiffened rapidly as his senses began to learn the appreciation of his situation and as his mom's well oiled finger slid inside his once virgin arsehole.

Jane felt her own pleasure, every vision coalesced to bring her to the brink of climax, her sons pert bottom in her lace knickers, his legs wrapped in her black stockings, his thighs laced with her suspenders and her glistening index finger disappearing into his tight wet rear. But as she saw her helpless boy drooling into her dirty knickers and his almost involuntary return to erection she knew this twisted and conflicted scene was darkly working for them both. Just the slightest touch of her fingers to her wet slit brought her to an orgasm the like of which she could not remember.

Jane could not help but jerk her finger harder into her sons moist hole, she had lost control of her physicality and delighted in the reaction of Tom's penis as it jerked with each thrust into his arse. She wanted more, so much more and by now no amount of social convention or fear of taboo would stop her. Nothing could stop her. Jane slowly removed her finger from Tom's anus and then spat into the slowly closing hole, roughly she grabbed at her sons short hair and yanked his head upwards. She pulled her by now soaked knickers from his mouth, "spit on it sissy, it'll make it easier for you". Her voice was unrecognisable to Tom, where was his loving, sweet mother? But he obeyed, drooling his saliva on her thick plastic dick before being gagged once again on her fragrant briefs. He didn't want to let pain interfere with his pleasure.

Feeling more cool lube hit his dimpled arsehole Tom then felt warmth, his mother's spit then more warmth as she eased her grotesque plastic cock into his willing shit hole. His cock jerked so hard he thought he would cum there and then but to his relief he didn't. For his mother the sense of entering her son which could not have been physical as it was only via an appendage felt so real that in that moment she knew how a man must feel when he fucked. The strap of her dildo slunk into her twat as she pressed slowly into Tom's rear but she didn't need the stimulation. In fact it was almost too much. Wave after wave of orgasm surged inside her as she watched her cock sink deeper into her sons widening, ever eager to yield backside.

Jane found rhythm now and her son with unacknowledged synchronsity assisted. Although Tom continued his stifled gagged moaning it now took on the unmistakable sound of pleasure. Jane too had abandoned berating her offspring she was unable to do more than gasp at the never before experienced levels of her climax. When she leaned over her son to grab on the breasts he had given himself with socks stuffed in Jane's pretty bra she thought the pulsating waves through her groin would cause her to feint. But she didn't, instead she held onto Tom's fake tits and used them to drag him onto her plastic cock like a brute fucking a whore.

Sweat began to form on Jane's brow, her dark loosely pinned hair started to stray on to her temples and on the nape of her neck it began to dampen. Tom felt his mother sink down onto him, using his body to rest her own. Her hot breath tingled his back and her gutteral grunts and gasps filled his ears. His mother was an animal. He had no idea he would get so much pleasure from anal rape but that was the gyst of it and from a woman, his own mother.

Pressing her tits into Tom's back Jane felt her rock hard nipples squeeze into his muscular frame and the overpowering electricity of climax surged through her again. Soaked in sweat and with her thighs slick in lube and her own juices she could simply take no more. Frantic, she slipped the strap on from her sons anus leaving it gaping and oozing like her own frustrated cunt and yanked at one of the binds on Tom's wrists. She hauled him over on to his back and saw for the first time the glistening, spasming magnitude of his over stimulated cock. He in turn saw in close up the beauty of her curvaceous breasts coated in sweat and the bulbous plastic penis that had given him so much joy. It was as if he wasn't there when Tom's mother with animal need tugged her strap on across her crotch and plunged her sopping, hot gash onto his jerking manhood.

Tom had been a virgin and to say he had never felt such a sensation would be obvious, perhaps more accurately it would be said he never would feel such a sensation again. His mom's wetness allowed his thick cock to thrust into her with no resistance. But Jane was a tight, toned woman, Tom was feeling the cushioned ease of a woman who had never known such stimulation and who's body had never produced so much juice as she came and came again.

Tom instinctively tried to raise his free hand to grab at his mother's inviting tit but Jane pinned his wrist to the bed and the thrust this delivered to her hips was enough to bring Tom's desperate, tortured penis to its first eruption inside a woman, his own mother. Jane felt his balls spasm against her sopping gash then the hot explosion of her boys pent up cum shoot deep up inside her. She screamed and clenched her long nails into Tom's chest as she bucked and twisted on his thrusting manhood.

Tom felt no pain from his mom's grip, his body was overdosed on physical and mental stimulation like he could never have imagined.

Jane sunk her body onto Tom's, her breasts coated in sweat slid against the lace of her bra that still contained her sons fake boobs. His mother's loosening hair tickled over Tom's skin as both mother and son heaved for air. For the first time since all this madness began Tom wondered if he felt intimacy with his mother. He was soon corrected. Exhausted and trembling Jane climbed from her son to reveal his penis thick with their juices as it slid grotesquely from her dripping pussy. Her juice escaped from between her legs and onto the floor as without a word she turned her back on her son and stumbled from the room ripping the false cock from around her waist.

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AnonymousAnonymous10 months ago

Next chapter please, this sissy needs more. 💕 4yourpleasureiam

AnonymousAnonymousabout 1 year ago

Excellent story, only criticism would be it could have used some build up in the beginning, cant wait to see more chapters!

AnonymousAnonymousabout 1 year ago

Did not care for this story a mother does not rape her son!!!!!!!!!!!

AnonymousAnonymousabout 1 year ago

When is the next chapter?

rdoolittlerdoolittleabout 1 year ago
Story of the day

Nailed it.

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