How Steve became Estelle

by Steve

My name is Steve, I have enjoyed your stories for many many years. I thought I'd send this little short story across as I thought you may like to share it on your site. Like all other sissies I wish I had a wonderful caring auntie like you to nurture and guide my sissy side

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The grand Victorian mansion on Wellington Road loomed like a pastel nightmare, its limestone facade softened by creeping ivy and lace-curtained windows. Stephen Matthews, 25 and desperate, clutched his threadbare satchel as he read the advertisement again:

*"Room to Let in Distinguished Residence*

*Nurturing environment for refined young gentlemen*

*Regressive therapies encouraged*

*Contact Lady Henrietta Ashworth-Pierce"*

The wrought-iron gate creaked open on its own. Stephen stepped onto a gravel path flanked by topiary rabbits and porcelain cherubs, their chipped smiles following him toward the entrance. Before he could knock, the door swung open to reveal three women in crisp navy uniforms-nurses from another era, their starched caps casting shadows over calculating eyes.

"Right on time, little one," purred a voice dripping with honeyed authority. Lady Henrietta descended the staircase, her emerald tea gown rustling like a serpent's shed skin. At her hip swung a silver rattle engraved with initials *H.A.P.* "We've prepared your nursery."

Stephen blanched. "Nursery? There must be some-"

"Tut-tut!" A nurse gripped his elbow, her latex-gloved fingers digging into his flesh. "We don't raise voices here, do we girls?"

The others tittered, adjusting their stethoscopes and patting medical bags that clinked with ominous glass bottles.

Lady Henrietta cupped Stephen's chin, her thumb smearing peach balm across his lips. "You'll learn proper decorum, darling. Nurse Wickersham will start your assessment."

They marched him to a powder-blue parlor where a mahogany changing table dominated the space, its leather straps dangling like dead snakes. Above it hung a cross-stitched sampler: *Blessed Are the Meek*.

"Now, let's see our new charge undressed," Lady Henrietta crooned.

Stephen stumbled backward into a shelf of antique dolls, their porcelain faces cracked into eternal pouts. "I didn't agree to-"

"*Tsk*. Naughty boys earn timeouts." Lady Henrietta snapped her fingers. The nurses descended, their practiced hands stripping his thrift-store tweed to reveal threadbare briefs. Cold air prickled his skin as they lifted him onto the table.

"Excellent pelvic tilt," Nurse Wickersham mused, snapping on rubber gloves. "Prime for containment."

Stephen thrashed as they spread his legs. "Stop! I'll call the-"

A pacifier forced between his teeth silenced him, the silicone nub flooding his mouth with saccharine vanilla.

"Shhh, precious," Lady Henrietta whispered, securing leather cuffs around his wrists. "This is for your own good."

The nurses worked with clinical efficiency-slathering his nethers in zinc ointment, powdering him with talcum that reeked of infantilizing lavender, then fastening him into a thick disposable diaper printed with dancing lambs.

"Pink terrycloth onesies for first offenses," Lady Henrietta declared, holding up a frilly garment. "We'll graduate to satin sissy dresses once you've earned playtime privileges."

As they encased him in the humiliating outfit, the women cooed over his "adorable blush" and "sensitive skin." Nurse Wickersham attached a leather collar with a heart-shaped tag: *ESTELLE*.

"Your dolly name," Lady Henrietta explained, adjusting his lace-trimmed bonnet. "We can't have our little princess clinging to vulgar masculinity."

They led him to a hexagonal solarium where other "charges" played-grown men in pinafores and puffy diapers, building block towers under the watch of severe matrons. A redhead in a bonnet suckled desperately at a champagne bottle filled with murky liquid.

"Your sisters in regression," Lady Henrietta said, patting Stephen's padded bottom. "You'll join them for Bottle Time after we've housebroken you."

Over the following days, the women dismantled Stephen's adulthood:

- **Nurse Wickersham** enforced a strict diet of puréed foods, spiked with tinctures that left him pliant and soft-limbed

- **Matron Briggs** conducted nightly "bladder retraining" with catheters and enema bags

- **Miss Delphine**, the French governess, tutored him in curtsying and doll maintenance while he wore a locked chastity cage

At Friday's "Nursery Soirée," they debuted his new identity. Ladies of high society sipped elderflower cordial as Stephen-now Estelle-modeled a strawberry-pink pinafore with matching lace-trimmed plastic pants.

"Isn't she divine?" Lady Henrietta asked the crowd, pinching Estelle's flushed cheek. "We're curing her nasty academic pretensions through wholesome play."

The women applauded as Estelle was made to demonstrate "proper little girl posture"-knees together, hands folded over her crinkling diaper.

By month's end, Estelle could recite her rules between sucks on her jade pacifier:

1. Big girls don't use potties

2. Frills prevent sinful thoughts

3. Mother knows best

When thesis deadlines haunted his dreams, Nurse Wickersham administered midnight "relaxation suppositories." When he tearfully recalled his old name, Miss Delphine locked him in the Sensory Deprivation Crib with a looping music box lullaby.

One autumn morning, Estelle awoke craving her raspberry-flavored teether. She toddled to the vanity on padded feet, admiring how the bonnet ribbons framed her smooth, hairless face. Behind her, Lady Henrietta smiled like a satisfied spider.

"Who's Mother's perfect princess?"

Estelle babbled around her pacifier, fingers instinctively checking her diaper's fullness. Somewhere beyond the rose-tinted windows, a student named Stephen had withered to dust-replaced by a cooing creature of lace and plastic and helpless need.

The mansion's gates would never open for her again.

Hope you enjoyed it.

Steve

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