Sissy Feminization: Exposing His Secret
: Chapter 6

Kathryn swirls the wine around in the glass inhaling the sweet aromatic scent of the red wine, gazing upon the dark skies eagerly awaiting her husband who is blissfully unaware of his pending true sissification.

‘Ok babes, the dishes are all washed’ Jennifer drags a chair closer to his wife and cosies up next to her.

‘I’m so proud of you honey’ Kathryn leans over and plants an unexpected wet kiss on her husband’s cheek ‘You’ve done a great job as a maid, our new neighbours have been fooled into believing you are a woman’

‘Uh-huh’ Jennifer nods

‘But I wonder how they failed to notice your massive erection poking out from under your skirt’ Kathryn slides her hand up her husband’s thigh, inching closer towards his panty clad cock.

Jennifer drops his head planting his eyes firmly upon his groin, the dull ache between his legs pounding and begging for release.

‘Do you know, I saw the way Tom looked at you when you bent over’ Kathryn giggles and she slowly pulls her hand away from between her husband’s legs ‘I think he saw your erection, and I think he was intrigued’

Jennifer involuntarily crosses his legs, sandwiching his throbbing cock between his thighs.

‘Damn, you look so ladylike today’ Kathryn’s eyes slowly roam Jennifer’s body, soaking in every ounce of his slow transformation. ‘Stand up and turn around’

Jennifer obliges pivoting on his heel, glad the darkness in the garden hid his predicament from the outside world. Kathryn grabs Jennifer’s ass and gently caresses her husband’s ass cheeks, massaging the mounds between her dominant fingers.

‘Bend over Princess’ Kathryn whispers into the darkness, her voice barely audible.

‘Wh…..wh…..wh……why’ Jennifer whimpers unaware of what Kathryn’s intentions are. Dressing him up indoors and teasing the neighbours in a controlled environment was one thing. But pushing his boundaries in the outside, for the whole world to see was entirely different.

‘Because I am about to turn you into a real sissy’ the coldness in Kathryn’s voice returns as she whispers her threat slowly in Jennifer ear, each word puncturing his soul with a searing hot pain.

Jennifer’s emotions are torn between the hunger between her legs, stirring in uncontrollable arousal begging for more humiliation and the fear of truly becoming emasculated by his wife. The crossdressing husband has been thrust into a reality he never imagined, a seed of thought inside of him contemplates what his limits are, humiliation and his masculinity appears to be a game to his beloved wife.

‘Hurry up’ Kathryn demands obedience.

Jennifer hesitantly bends over, resting her elbows on the wooden bench in front of her, her skirt rides up her thighs and Jennifer suddenly feels exposed and at the mercy of his cruel wife as an unexpected gust of wind wraps it cold and sharp talons around Jennifer’s thighs and inches itself towards the throbbing erection between his legs.

Kathryn reaches her arms around her husband’s pelvis and hunts around for his cock, she grabs his manhood with both hands, separating her husbands cock in one and his testicles in the other and starts to massage them between her palms. She grips one of his tender balls between her fingernails and pinches the centre, smiling as Jennifer’s body jolts in reaction to the sudden burst of pain emanating from his balls.

‘Any time you show any signs of masculinity from now on’ Kathryn tightens her grip on her husband’s trapped testicles ‘I will squeeze, torment and torture the very essence of what makes you a man, reminding you of your true place in our new relationship’ the dominant wife pinches her husband’s isolated testicle further to impose her point on his vulnerabilities.

Jennifer squeals into the darkness as the sudden pain between his legs shoots an unparalleled combination of fear and arousal coursing through his body. He struggles to comprehend his arousal at the mere thought of succumbing every ounce of his masculinity and control to his powerful and dominant wife.

Moments later, the neighbours bedroom lights are switched on and Jennifer’s predicament is suddenly thrust under the spotlight to the outside world, dressed in a maid’s outfit, bent over the bench and with his wife’s iron grip on his testicles squeezing him relentlessly, draining him of any remaining ounce of masculinity. Jennifer squints as he looks up at his neighbour’s top floor bedroom window, his body freezes as he notices two figures peering out of the window and staring down at him. Jennifer gulps as he recognizes Tom and Chloe from earlier glued to their windows, watching his emasculation unfold in front of their very own eyes. The crossdressing husband closes his eyes and wishes for the ground to open up and swallow him whole, removing any trace of his humiliation from the Earth.

‘Stay here, I’ll be back’ Kathryn shoves her husband’s head forward and tugs his testicles upwards, pulling his ass higher ‘and if you move from this spot’ Kathryn pinches her husband’s nut harder and smiles as he squeals once more, only this time in a higher tone and louder. She releases her iron grip and leaves Jennifer bent over the bench with his ass in the air, whimpering for her return under the watchful gaze of their new neighbours.

Jennifer holds his gaze on the spot on the wooden bench between his arms, too ashamed to look back up and see if the neighbours were still watching. Their back garden light was still lit and they no doubt were eager to watch the events unfold. Jennifer shook his head, struggling to comprehend what was about to happen. What the neighbours would think. But more importantly what the future was going to hold for him and Kathryn. It was mere hours ago that he was dancing in the house all alone eager to try on his wife’s panties, and now, now, if anyone would have told him he would be in this predicament hours later. He would have dismissed the idea as utterly ridiculous.

Kathryn returns moments later holding a large black strapon and a bottle of lube. She maneuvers herself in front of Jennifer and smiles as she watches his eyes almost pop out of his eye socket as she slowly slipped the harness to her waist.

‘Wh….wh….what is that’ the crossdressing husband whimpers

‘It’s the next stage of your emasculation’ Kathryn smiles ‘Don’t worry, we’ll make sure we use lube’

‘Lube?’

‘Yes darling’ Kathryn pops open the bottle of lube and spreads copious amounts of the liquid across the full length of the plastic shaft,coating it’s entirety from the base of the gigantic cock to the thick head ‘I mean, there is no way your ass is going to take nine full inches without a bit of gentle persuasion’

‘My ass?’ Jennifer’s jaw almost dropped at the thought of the huge device hovering menacingly above his head, threatening to slide into his asshole.

‘Yes sugar, your ass’ Kathryn wraps both of her hands around the monster cock and jerks the piece slowly in front of Jennifer’s eyes, smiling as observed a hint of a tear forming.

‘Bu….bu……but I’ve never taken anything inside my ass before’ Jennifer struggles to comprehend how a device marginally larger than his throbbing cock would fit inside his ass. He feels his anus clench involuntarily at the mere thought of succumbing to the veiny weapon his wife held between her hands.

‘I know which is why I’m going to go nice and slow’ Kathryn brushes the tip of her plastic cock against Jennifer’s trembling lips ‘tonight, I will strip you of your anal virginity and turn you into a true sissy’

Kathryn saunters behind her husband slowly, fully aware she was putting on a show for the neighbours she had met hours ago. She wonders if they had sussed out the new dynamic of her and her husband’s relationship. Whether they believed the maid was really a husband of whether they were going to replace out in minutes as she pummeled her huge plastic dildo into her husband’s virgin ass. The dominant wife lifts up Jennifer’s skirt and yanks down her husband’s panties smiling as his ass clenched involuntarily as the cold air attacked his bare cheeks.

‘Don’t worry, I’ll be gentle for your first time hubby’ Kathryn giggles raising her voice slightly for the neighbours benefit. She grips both of her husband’s ass cheeks with each hand and gently parted his ass opening up the gateway into his body.

‘A little nervous, are we’ Kathryn struggled to slide her finger into her husband’s tight anus and smiled as his anal walls twitched and violently snapped shut wrapping his anal walls tightly around her finger, gripping on for dear life.

‘Wh…..wh…….wh…..why am I so turned on by this’ Jennifer looked down between his legs and noticed his raging hardon was gagging for attention, hungry for release as it slowly dribbles precum across his shaft.

‘I think deep down inside, you were destined to be my little sissy bitch’ Kathryn slide her finger out and smirked as she saw her husband’s browneye wink for more. Kathryn squirted lube on her husband’s ass cheeks and gently massaged the liquid between his ass cheeks, moistening his crack in preparation for her welcomed violation.

‘Oooooohhhhhh’ the liquid slid down Jennifer’s crack and provided him with some much needed warmth as his ass cheeks were exposed and shivering under the cold and dark air around him.

Kathryn pressed the tip of her hungry plastic cock against her husband’s tight anus and pressed in gently, threatening to break through his resistance without a moment’s thought.

‘Ready babes?’ the horny wife slaps her dildo violently against her husband ass cheeks and teases his anus once more.

‘B…..b……b…….bu…….but the neighbours are watching’ Jennifer whimpered as he eagerly anticipated his anal deflowering..

‘All the better to have an audience as I tear your masculinity out from under your nose’ Kathryn raised her hand towards the neighbours both acknowledging their presence and signalling the green light for them to enjoy the show.

‘B….b…….b…….but I can never meet them as your husband’ the confused maid looks back at Kathryn.

‘You are no longer my once manly husband’ Kathryn presses her cock harder against and grips onto his hips.

‘What do you mean’

‘You are now my sissyslut’ the dominant wife thrusts her pelvis forward and tears through Jennifer’s anal resistance soaking in the audible pop of her husband’s anal cherry.

‘Uuuhhhhhhhhhhhh’ Jennifer groans as her anus welcomes the sudden intrusion, her anal walls quickly clamp around the offending strapon locking several inches of the thickness inside her ass.

‘Relax and enjoy your public emasculation’ Kathryn retracts the dildo slightly and reenters her sissy husband, pushing deeper with each thrust. Her adventurous strapon explores her sissy maid’s anus further with each intrusive push violating the unexplored areas of Jennifer’s anal cavity. Kathryn slowly starts to pick up a sensual pace as she starts to plow into her husband’s once virgin anus with a steady rhythm, weakening the natural resistance of his anal entry.

Tom and Chloe watch as the events unfolding before their very eyes, the neighbours living next to the house they have just bought exhibiting unusual and strange behaviour.

”That maid looks a little strange’ Tom squints at Jennifer desperately gripping onto the bench in a feeble attempt to manage the force pulling into his ass.

‘I don’t think that’s really the maid’ Chloe smiles up at her partner

‘What do you mean’

‘You’re telling me you didn’t notice’ Chloe sides her hands between her husband’s legs and hunts for his thick cock ‘That was her husband dressed as a maid’

‘Dang, and there was me admiring the maid’s fine booty’ Tom mutters under his breath as he shakes his head in astonishment.

‘How does this feel’ Kathryn roared as she continued slamming into her husbands ass ‘Become my little sissyslut’

‘Ooohhhh’ Jennifer moaned in pleasure,

Kathryn continued barrelling her thick strapon into her husband’s anus, dominating every inch of her partner’s body with her brutal and intrusive device, claiming rights over every unexplored area. Kathryn pulled her husband’s ass forward and forced his head down on the bench opening up his anus further. She continued thrusting her curious strapon further into the darkness reveling in the dominance she exuded over her weak husband in front of the neighbours.

‘There is no going back from this’ Kathryn retracted her strapon, violently slapping his ass cheeks and then reentering with a desire to scar him permanently. She begins to fuck her partner with an unparalleled aggression, unable to control her body’s urges as she succumbs to her own desires, ignoring the maid in front of her as her husband and instead, treating him purely as a fuckhole. For her pleasure. Any only her pleasure.

The dominant wife lets her body take over and she continues to fuck her sissified husband with a burning passion to humiliate him in front of the peering neighbours. A drip of sweat rolls down her forehead as she clenches her thighs as she feels the pending orgasm pounding at the gates of her womanhood. She rides her husband harder and faster, ignoring the wobbling bench under the power of her thrusts.

Jennifer tightens her grips on the sides of the bench and holds on for dear life, conscious the neighbours are watching and the wooden bench is moments away from giving way. She repositioned her mind to stay in the moment and to enjoy the thorough ass pounding Kathryn was exerting on his feminized body.

Kathryn’s aggression reachs unparalleled heights as she barells her strapon with machine gun like speed and laser like precision, truly dominating her husband’s body. And without warning, her thighs tighten uncontrollably as she feels a ferocious orgasm smash through her floodgates, drenching her thighs and spilling across the entire bench. She roars a deafening scream into the night, asserting her dominance over her husband as her juices trickle onto her strapon, providing additional lube as she continues to pummel into Jennifer’s ass, Kathryn now a slave to her own aggression sinks her cock into her husband deeper and deeper. The wooden bench continues to strain under the sheer weight of the husband and wife until it can no longer maintain it’s form, the legs crumble sending the couple crashing into the ground. Kathryn chuckles as the full length of her plastic dildo lodges itself deep inside her husbands ass.

“How do you feel, my little sissy slut?” Kathryn unstraps the strapon from her waist and leaves the device lodged in her husband’s throbbing ass.

“Ahhhhhhhh” Jennifer groaned as he felt the remains of his wife’s juices trickle down his ass cheeks worming around the piece protruding out of his ass.

“Once you have quite finished relaxing” Kathryn walks around to Jennifer’s head and towers over him with her hands on her hips “clean this mess up and then you can join me in inside to continue”

“Continue?” Jennifer looked up at Kathryn

“Continue to please me and we can end the perfect night of firsts in style” Kathryn slipped her fingers between her legs scooping out a puddle of her juices and wiped her fingers across her husband’s forehead.

Jennifer groaned in response as he looked up and saw the neighbours continuing to watch his humiliation.

“And tomorrow, we can go shopping and we can start to stock up your new wardrobe in style” Kathryn clapped her hands and returned back into the house, leaving her husband lying flat on his face with his ass in the air, sore, batter and bruised.

Jennifers stares at his wife’s ass as she saunters back inside, closing the back porch door behind her. His thoughts suddenly become crystal clear as he contemplates the last few hours of his life. His wife’s words stay with him, circling his conscious threatening him with it’s vision of the future. He smiles knowing tonight was only the beginning and there is a lot more to come in their new sexual adventure.

Jennifer rolls onto his side careful not to lean on his ass and repositions his cock, he smirks as he watches it slowly stir awake hungry for more.