A Night To Remember

The bedroom door flies open, stepping through is Catherine with Riley held tight in her arms, hands firmly gripping their ass as they kiss passionately, approaching the bed.

The kiss means so much more then mere affection, in a way it solidifies the respective roles of their relationship, it represents Riley well and truly giving all they have to Catherine.

Riley is laid back onto the mattress, reluctantly releasing their mother’s waist as they open their legs, a pink hue having covered their face as they look up into their Mommies eyes.

“I just need to grab a few things baby girl~ I wanna make this night magical for you~” she says, warmth and love saturating her every word as she looks down upon her little blushing princess.

Riley can do little more then nod their head sheepishly before laying back and staring at the ceiling as they try to steady their nerves. Sure Riley had experience with oral and they always suspected something like this would happen if they got claimed by a futa but they had never really experimented with anal before.

There’s a sound of opening drawers from behind followed by the telltale sound of hands digging through clutter, Catherine giving a satisfied hum as she finds what she’s looking for.

Riley dare not look, a part of them slightly concerned by what they’d find and the last thing they want is to chicken out of what is meant to be the ultimate conclusion to their first ever date.

There’s more commotion, the sound of fabric sliding along long legs, the quiet rustling of straps tightening and finally the sound of clothes hitting the floor.

Catherine takes a few steps, returning to where she has stood only moments before between Riley’s legs that hang off the bed limply.

Slowly Riley’s gaze lowers from the ever fascinating texture of the ceiling to the face of their mother, her lips curled in an almost impish grin and her spiraling emeralds speaking only of love and desire.

Their gaze lowers further, scanning along Catherine’s heavy chest, each large enough to imprison their head in their warm loving embrace.

Her nipples stand firm as though an arctic gale had blown through, speaking even further to her enthusiasm for what comes next.

Riley can’t help but stiffen in their panties, heart skipping a beat as lustful images pass through their mind, the sight of Riley worshipping them as they rest on her lap being the most prominent of these fleeting day dreams.

Further south their sight traveled, roaming down along her cushioned, soft belly and landing at her hips where sits an odd device but one Riley recognizes all too well.

It was what they had feared, it was what they had hoped, the ideal tool for turning an eager pet into a hopeless, drooling sissy, one that Mommy had always wanted.

The only thing Catherine wears is a strap-on, one that’s been clearly designed to look as minimal as possible, as though to trick its recipient into thinking it were real, a thought that is only reinforced as Riley notes that the hue of the dildo is both hyper realistic and the exact same as Catherine’s skin tone.

Riley gives an involuntary gulp, shivering quietly where they lay why Catherine gently folds her arms behind her back, chewing her bottom lip as she takes in the look up her soon to be daughters face.

“I… I know that Mommy doesn’t have ALL the equipment a girl like you needs but.. well… we’ll make do for now…~” she says, a predatory look resting in her eye as she gently unfolds her arms to reveal the bottle of lube she holds.

“Now… normally I’d do this myself but wouldn’t you like to get to know her a little more….~?” She asks, setting the small bottle down on the bed within arms reach of Riley.

A wave of embarrassment rolls over Riley, not only would they be fucked by that thing, they’d also be expected to lube it up with their bare hands! Had anyone else asked such a thing it would almost be an insult but with her it felt… natural, like an invitation to explore her new appendage before being thrown into the deep end.

Riley’s hands rattle and shake as they squirt a perhaps overindulgent helping of lubricant to their hand before gently wrapping their fingers around the base of the member.

It feels almost identical to how Aubrey’s length felt, Riley could trace the heavy veins that protrude from the powerful shaft, they could feel how the material gives a little bit before becoming firm in their fist. However there are several noticeable differences from the real thing, there’s no heat to the material at all, something to remind Riley that at the end of the day this is silicone not flesh nor does their seem to be any life to the toy, Riley cannot feel the blood flowing within the length, they can’t feel it twitch or throb in their hands.

Thankfully it’s smaller than Aubrey’s length by a fair margin, standing at 8 inches in length and 2 and a half inches in diameter making it large enough to presumably satisfy but not much more.

Slowly Riley’s hands glide along the silicone of the toy, Catherine watching from on high, an intensity burning in her eye as she chews her bottom lip, almost as if to silence herself. The toy shines and glistens in the light as Riley throughly soaks it through with lubricant, their heart pounding in their chest as they jerk off the toy.

Catherine doesn’t say a word, she doesn’t move an inch, merely looking on like a watchful guardian as they observe Riley, taking special note of the bulge that twitches in Riley’s dress, confirming in her mind that she had made the right choice, that this was meant to be.

Eventually through her desires, her needs, get the better of her, as she watches Riley gently stroke her cock, each movement accompanied by a slow, drawn out SCHLLLLCK sound.

“Mmm… ok baby girl… I think that’s enough for me… how about we lube you up now…~? We don’t want you getting hurt do we..~?” She asks, her voice saturated in equal parts motherly compassion and sultry desire causing Riley to shiver as her words creep into their ears.

“Go ahead and get on your hands and knees for me, princess~ Mommy knows just the trick to get you ready~ I think you’ll like it too~” she says, Riley’s body complying to the command on its own, it seems even on a biological level Riley belongs to their mother.

Riley’s ass points towards their Mommy, raised ever so slightly creating a barely noticeable arch. They can’t help but give a small whimper as they feel the soft but powerful hands of Catherine gently rest on Riley’s thighs, traveling upwards beneath the hem of their dress before fingers curl around the waistband of their panties, all of this happening as slowly as Catherine’s hunger will allow.

The panties are pulled down in one continuous motion, not stopping until they rest at Riley’s bent kneels, the only thing covering Riley’s ass now being the back of their dress but it’s not much longer until this too is pushes away.

Catherine gives something between a moan and a giggle as she looks upon the cushioned cheeks of Riley’s ass, her eyes wild as it takes all the restraint and love she has not to **** the tip of her silicone cock inside that twitching virgin pussy.

Gently she grips the girlish backside, slowly prying it apart to expose Riley’s soon to be boy pussy to the open air prompting a small wink from the tight little ring, as though inviting Catherine for a closer inspection. An invitation she’s happy to accept.

“B… baby… your gonna feel something strange now b… but don’t worry… in time you’ll grow addicted to it….~” she says, the hunger heavy in Catherine’s voice as she speaks as if losing a mental battle against her own desires.

Riley braces themself and that strange sensation arrives, the feeling of a hot, wet, slippery appendage slowly circling the perimeter of their asshole as if testing its defenses.

Riley lets out a shuddering gasp, attempting to hold still as that odd, foreign sensation dances along their nerves, making toes curl and muscles tighten.

Catherine hums softly to herself as she tastes of her daughters aching cunt, tasting every bit as divine as she had expected, the ring tightens and loosens sporadically at the new experience coaxing Catherine to dive deeper, her tongue sinking into the ring of Riley’s ass, slowly drawing small circles with the tip of her tongue as she savors every shiver and squeal she receives and Riley DOES squeal.

That strange sensation deepens and blossoms into a strange pleasure Riley had never considered before, something so agonizing and wonderful that their mind could scarcely comprehend.

Further and further into Riley’s depths does Catherine descend, not content until she makes contact with perhaps the single most useful tool in feminization, the prostate.

Sure she could dress Riley up, she could call them a good girl but at the end of the day the doubts would always remain, those little niggling doubts would be waiting in the forgotten corners of their mind ever ready to spring out. No, if Catherine were to prove beyond a shadow of a doubt that this is Riley’s truest self, she must bring to bear the most powerful experience a girl like Riley could endure.

Slowly her tongue searches Riley’s depths, finally reaching a small, stiff bulb a couple inches into their pussy, she laps at it and is rewarded with a small shiver from Riley’s body, confirming her suspicions.

Gently she presses down in the strange sphere buried halfway into the walls of Riley’s maidenhood, coaxing girlish squeaks and causing the poor thing to squirm and writhe powerlessly beneath Catherine’s ministrations.

Finally after several minutes of teasing, Catherine takes pity on the poor dear, slowly retracting her tongue from Riley’s nethers leaving them slightly dissatisfied, almost feeling empty now.

It’s only when Riley feels their mothers tip press on the spit soaked rim of their hole that they are reminded of what this was all for, tonight they would be made a woman at the hands of their mothers cock.

There’s a moment of hesitation on Catherine’s part, before finally she speaks, her voice coming out as a serene, nurturing tone Riley had been so familiar with.

“Sweetie…? I.. it would mean the world to me if we did this next part with you… on your back…~” she says, a small part of her **** to see the look in their eye when they realize their true nature.

Riley gulps quietly, slowly turning over on their side before ending the movement on their back, legs open and raised up, Catherine’s hand quickly landing on the back of their thighs, holding Riley’s legs in this submissive, **** position.

The sensation returns, her tip gently prodding Riley’s ring, her eyes locked onto Riley’s face as she slowly presses her hips forward, going so slowly she almost doesn't move at all, the gentle prodding slowly becoming a pressure that ever so slowly builds and builds, Riley’s ass slowly losing the struggle to keep the intruder out as the rim opens ever so slightly.

Finally the pressure becomes too much, the defenses faltering as the virgin ring opens to accept Catherine’s tip. Riley lets out a cry, a mixture of dull, throbbing pain and that strange almost alien pleasure from before, each side fight tooth and claw within Riley to decide whether or not they like this.

This inner conflict must be visible upon Riley’s face as Catherine’s eyes widen ever so slightly, like a lion watching a gazelle break off from the pack, an intensity burning in her eyes but not one that suggests cruelty or malice.

The movement stops, only the tip remaining, gently stretching the rim as Riley acclimates to the new experience, the throbbing pain slowly fading into a mild discomfort, Riley’s pained whimpers dying along with it.

A smile slowly spreads across Catherine’s face, wide and warm as she takes in this moment as though it were a historical event, something to be remembered and cherished for all time.

Slowly the movement picks up, a slow push of Catherine’s hips, slowly feeding more and more of her cock into her precious baby, her hands gently stroking Riley’s thighs as her length slowly disappears into their ass.

Riley’s breath catches in their throat, eyes widening as they feel her tip lay a small kiss upon that special spot, that strange bulb that seems to be central to their pleasure going forward.

Riley stares up into their mothers eyes as they share a small communication, one that requires no words be spoke as Catherine begins to gyrate her hips up and down, forcing her tip to grind along the surface of that wonderful bump sending sparks of pleasure rippling through Riley’s core, coaxing small squeaks from them.

The feeling is powerful, causing Riley’s hands to shake and their cheeks to flush, heart skipping a beat as they look up into those eyes, so intense and powerful, Riley has **** but to look into them, they demand it.

This agonizing teasing goes on for far too long, Riley’s little body begins to squirm, unable to keep still as Catherine massages their prostate, their cock drooling and twitching expectantly, begging for attention that it will never get.

Catherine’s voice breaks through the lustful fog, calling Riley to attention as they stare up into those twin emeralds.

“I’m going to start now baby~ you be as loud as you want… I want the whole neighborhood to hear this~” she reassures, her words instilling a fearful excitement from Riley as she slowly retracts her hips, pulling back until her back makes a small arch.

The tension is thick as Riley waits in suspense, their poor ass gently tightening and aching around the tip, begging to be fed, to be filled. Just as the atmosphere reaches a boiling point she thrusts, a powerful stabbing motion deep into Riley’s ass, the tip ultimately colliding with their prostate, sending lightning throughout the entirety of their frame.

Their jaw drops, their fingers dig deep into the sheets as they let loose a lustful scream, notably girlish as Riley’s whole frame shudders and quakes in the aftermath of such a powerful blow.

Riley barely has time to recover from the first strike when the second comes sailing in, another direct hit, sending their brain into a spin, thoughts being pushed to the side, pleasure overwhelms their nervous system.

The flurry of blows continues, each one terminating in a strike on Riley’s G spot, each thrust slowly turning Riley’s asshole into a pussy.

The room fills with the sounds of flesh striking flesh and girlish screams of uncontrollable pleasure; the sounds of a boi becoming a woman.

What few thoughts remain in Riley’s head as Catherine hammers away, speak to how right she was, if Riley wasn’t meant to be a little girl, WHY DOES THIS FEELS SO GOOD?!

If Riley was a man or even a boy, he would hate this, this would feel unnatural and wrong, Riley wouldn’t be a limp, spasming mess, tongue hanging out and toes curled as they gleefully receive their mothers cock.

It’s all so obvious now, Riley was such a fool, Catherine had known all along that this was meant to be, she was right, Riley isn’t a man and never will be, Riley is a girl! Mommies girl! And she’s so glad Mommy showed her the truth!

Riley pants and gasps for breath in between moans, her heart pounding in her ears like a drum as the pounding continues, soon Catherine leans in, her hands moving to the mattress as her shoulders hold Riley’s legs in position. Riley can feel her Mommies chest press down onto her own, her lips just a foot away from hers as Riley shows how grateful she is in her lustful moans of delight.

Catherine pants as well, the interior dildo pushing in and out of her with each thrust, encouraging her rough pounding of her little girl. Her smile widens, almost to a manic degree as she watches the shift in Riley’s mind, peering into the inner machinations of the poor things mind, watching with glee as she breeds whatever last vestiges of masculinity out of her perfect princess.

She can feel the orgasm build in Riley’s core, noticing how rapidly and sporadically she tightens around Mommies cock, their cute little clitty jumping and drooling, ready to squirt at any minute. Catherine can feel an orgasm growing within herself as well, the sight of Riley’s true leap into the world of womanhood doing more for her then any toy or lover could.

She speeds up, her hips aching from the sudden strain of breeding after so many years but she pushes on, not content until she can guide Riley to her first climax as a woman.

Riley can wait no more, her back arches and she cries out in unrestrained bliss as her first sissygasm claims her body, her legs shivering and quaking, every muscle rapidly tightens and loosens including that of her newly christened boi-pussy, her eyes roll back and the entire neighborhood is informed of the events of the room as Riley cries out for Mommy.

Catherine is quick to join her daughter in orgasmic bliss, quickly bottoming out inside Riley’s pussy as she buries her face into her neck, leaving a series of kisses and love bites that would prove impossible to hide assuming Riley had any interest in it.

Riley’s clitty finally gets its release, weakly drooling out a small watery load that sticks to both both Riley’s and Catherine’s bellies.

Riley’s mind spins, her eyes fluttering closed as she soaks in the afterglow of the single most powerful orgasm of her life, her body limp in Catherine’s arms as they share in the moment.

Evidence of Catherine’s climax slowly runs down her cushioned thighs, though not as physically powerful as Riley’s, it’s still every bit as fulfilling.

“I love you Mommy…~” Riley mutters, trying to fight off the slowly encroaching darkness of sleep but steadily losing the fight.

“Mmmm…~ and I love you baby girl…~ I’m so lucky to have you~” Catherine states, locked in an equally hopeless battle with the realm of dreams.

Before long, each of them drift off, Catherine still laying on Riley providing all the warmth the diminutive girl needs as sleep claims their minds.

(A/N: This is possibly my best sex scene to date, I really hope you all enjoyed! I’m not quite sure where I wanna take this storyline yet so I’ll focus my attention elsewhere for a little bit. Stay tuned!)