Sissy's Landlady Catches Her in Silky Stockings

Sissy's Landlady Catches Her in Silky Stockings

I still remember the exact creak of the attic stairs that afternoon. I was supposed to be at a late lecture, but I’d skipped it the moment Mrs. Voss left for her weekly grocery run. The house was quiet except for the low hum of the old radiator, and my heart hammered so hard I could feel it in my throat. My name is Alex, twenty-two, painfully shy, and for the last six months I had been living a double life in this tiny rented room under the eaves.

Today I was Sissy.

The silk stockings were the color of expensive champagne, sheer enough to catch the weak autumn light spilling through the dormer window. I had rolled them slowly up my freshly shaved legs, clipping them to the delicate lace garter belt that hugged my narrow hips. The matching panties were a whisper of white lace, barely containing the insistent bulge of my smooth-shaven cock. A pair of black patent heels—four inches, bought online and hidden behind a loose floorboard—completed the outfit. No wig yet, no makeup; just me, trembling, standing in front of the full-length mirror I’d propped against the wardrobe door.

I turned slowly, admiring the way the stockings shimmered over my calves and thighs, the way the garter straps framed my ass like an invitation. My clitty twitched visibly against the lace, leaving a tiny wet spot. I looked… pretty. Vulnerable. Desperately fuckable. A soft, needy sound escaped my painted lips.

The bedroom door opened without a knock.

Mrs. Elena Voss filled the doorway like a storm front. At thirty-eight she was all lush curves and strict posture—wide hips, heavy breasts straining the buttons of her cream blouse, dark hair pinned up in a severe bun that only made her cheekbones sharper. Her emerald eyes widened, then narrowed. For three full seconds the only sound was the click of my heels as I instinctively tried to step back and nearly toppled.

Her gaze dropped to my legs, lingered on the taut stockings, traced the garter straps, and finally settled on the obscene little tent in my panties. I watched a slow flush creep up her neck.

“Oh… Sissy,” she said, voice low and velvet-rough. “I thought I might find something like this one day.”

I couldn’t speak. My mouth opened, closed. Heat flooded my face so fast I felt dizzy.

She didn’t yell. She didn’t order me out. Instead she stepped inside, closed the door behind her with a soft, deliberate click, and turned the key. The sound of the lock sliding home made my clitty throb so hard it strained visibly against the lace.

“I’ve suspected for weeks,” she continued, advancing slowly. The floorboards creaked under her weight. “The way you blush when I come upstairs. The extra laundry you try to hide. That rather obvious delivery from the lingerie site last month.” Her full lips curved. “You really should use a PO box, darling.”

She stopped an arm’s length away. I could smell her perfume—something warm and expensive with a hint of vanilla and spice. Her eyes were hungry.

“Turn around for me. Slowly.”

My legs obeyed before my brain caught up. I pivoted on the heels, letting her see the back of my thighs, the way the stockings stretched tight over my ass, the little satin bows at the tops of the garters. When I faced her again her breathing had changed.

“Fuck, you’re exquisite,” she murmured. One manicured hand reached out and traced a single finger up the back of my left stocking, from ankle to the sensitive skin just below the lace band. The touch left a trail of fire. “So smooth. So shy. Look at you… leaking already.”

A broken whimper slipped out of me. My knees wobbled.

“Please…” The word fell out like a confession.

Mrs. Voss’s smile sharpened. She cupped my chin, forcing my eyes up to hers. “Please what, pretty girl?”

My voice cracked. “Please… touch me more, Mrs. Voss.”

Her grip tightened just enough to sting. “That’s not my name anymore. Not when you’re dressed like this. Try again.”

The word rose up from somewhere deep and submissive I had never let anyone see. “Mistress.”

Her eyes flashed with triumph. “Good girl.”

Then she kissed me.

It wasn’t gentle. Her mouth claimed mine, tongue pushing past my lips with confident hunger while her hands roamed. She stroked up the front of my stockings, palms gliding over the silk until she reached the straining lace of my panties. She squeezed my clitty through the fabric and I moaned into her mouth like a whore.

When she pulled back, her voice was husky. “On the bed. Bend over.”

I scrambled to obey, knees sinking into the old quilt, ass presented, back arched. The heels made my calves flex beautifully. I heard the rustle of clothing, the soft metallic clink of a belt. Then her hands were on me again—spreading my cheeks, thumbs brushing over the lace that barely covered my smooth hole.

“Such a polite little sissy,” she purred. “Already shaved for me. Were you hoping I’d catch you?”

I nodded frantically into the pillow.

She ripped the panties aside with one strong tug. The sound of tearing lace made me cry out. Cool air kissed my exposed hole, then warmth—her breath. Then her tongue.

The first long, wet lick across my tight pucker sent lightning up my spine. I keened, pushing back against her face. Mistress Elena licked me like she was starving, tongue swirling, probing, fucking into me while one hand reached underneath to stroke my dripping clitty through the shredded remains of the panties. The dual sensation—silk and spit and firm fingers—had me shaking within seconds.

“You taste like sin,” she growled against my hole. “And you’re going to come just like this if I keep going, aren’t you?”

“Yes, Mistress—please—”

She stopped. I sobbed at the loss.

“Not yet.” The sound of a drawer opening. The obscene snap of a harness. When I looked over my shoulder she was stepping into a thick, veined strap-on the color of deep rosewood. It jutted from between her strong thighs like it belonged there. She lubed it generously, eyes never leaving mine.

“On your back, legs up. I want to watch your face while I fuck you.”

I rolled over, stockings whispering against the quilt. She climbed between my spread thighs, hooked my knees over her shoulders, and pressed the fat head of the cock against my spit-slick hole. One smooth thrust and half of it sank inside me. The stretch was perfect—full, burning, delicious. I cried out, fingers clawing at the sheets.

“That’s it,” she groaned, sinking deeper until her hips met my ass. “Take every inch for Mistress. Look at those pretty stockings wrapped around me. Fuck, you were made for this.”

She started to move—long, powerful strokes that dragged over my prostate on every pass. My clitty bounced against my belly, smearing pre-cum across the garter belt. The wet slap of her hips against my ass filled the little attic room. I wrapped my stocking-clad legs around her waist, heels digging into the small of her back, urging her deeper.

“Yes—harder, Mistress—please fuck your sissy harder—”

Elena’s laugh was dark and delighted. She leaned down, biting my nipple through the thin camisole I’d forgotten I was wearing, and pounded me until the bedframe rattled. I was close already, embarrassingly close, when she suddenly pulled out.

“Up. Reverse cowgirl. I want to watch that pretty ass bounce.”

I straddled her on shaky legs, facing away, and sank back down onto the thick strap-on with a long, grateful moan. The new angle made it feel even bigger. I started riding her, rolling my hips, stockings stretched tight over my spread thighs. Her hands gripped my waist, then slid down to smack my ass—sharp, stinging slaps that made me clench around her cock.

“Look at you,” she panted, voice rough with lust. “Leaking all over your own garters like a desperate little slut. Touch yourself. I want to feel you come hands-free while you ride me.”

I braced my hands on her thighs and let gravity do the work, bouncing faster, the fat cock spearing me over and over. My clitty slapped wetly against my belly, then the garter straps, then my own stockings. The silk was already soaked. The pressure built, coiled, then snapped.

I came with a broken wail, hands-free, thick ropes of sissy cum splattering across my champagne stockings in messy white streaks. My hole fluttered and clenched around her strap-on so hard she groaned like she could feel it. She kept fucking up into me through every spasm, milking every drop until I was shaking and empty and whimpering her name like a prayer.

When the last aftershock faded she eased me off, the thick cock sliding out with a wet pop. I felt hollowed out and glowing.

“On your knees.”

I slid down immediately, thighs trembling. The strap-on glistened with lube and my own cum. Without being told I opened my mouth and took it, sucking obediently, tasting myself on her. Mistress Elena stroked my hair, gentle now, murmuring praise.

“Good girl. Such a perfect, obedient little tenant. From now on you’ll dress for me every weekend. Stockings, heels, pretty panties. No arguments. Understood?”

I nodded around the cock, eyes watering but shining with happiness.

She finally pulled me off, unbuckled the harness, and drew me up into a surprisingly tender kiss. Her tongue swept through my mouth like she was claiming territory. When she pulled back she was smiling—soft, satisfied, and just a little wicked.

I was still flushed and sticky, cum cooling on my ruined stockings, when she cupped my cheek and said, in the most matter-of-fact tone imaginable:

“Next weekend I expect you to shave that little clitty even smoother. And darling… try not to leave the lube on the nightstand. My bridge club meets down the hall, and Mrs. Abernathy has the nose of a bloodhound.”

I stared at her, cum-drunk and dazed. Then I started to laugh—helpless, giddy, mortified laughter that turned into a snort when she arched one perfect eyebrow and added, “Besides, if she finds out, she’ll want a turn. And I don’t share my sissy.”

I buried my burning face in her generous cleavage, still laughing, already wondering which pair of stockings I’d wear first for her next weekend.