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Caught

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By *ssexNewSub OP   TV/TS
7 days ago

Coggeshall

At 38, I’m a man with a double life. Married to Claire for five years, I’m a stepdad to her two daughters, Lily and Emma, who are 16 and 19. I love them, but our small house offers no privacy for my deepest secret. Since I was a teenager, I’ve been drawn to women’s clothing—the way silk and lace feel against my skin. It started with sneaking a pair of my mom’s panties, the thrill of the forbidden setting my nerves on fire. Over time, it became my escape, my way to feel alive. But with a family at home, I can’t dress freely. My stash—lingerie, stockings, a suspender belt—is hidden in a locked box in the garage, where Claire and the girls never go. I dress in moments when they’re out, heart racing, always terrified of getting caught.

Tonight, I pushed further than ever before. Claire took the girls to visit her parents for the weekend, leaving me alone. The temptation was too strong. I didn’t dare go full drag—no wig, no makeup, no chance of passing as a woman with my chubby, plain frame—but I slipped into my favorite pieces: sheer black stockings, a suspender belt that dug into my hips, a pink lace thong that barely contained me, and a short black skirt that hugged my thighs. Over them, I threw on loose jeans and a plain T-shirt, the most ordinary outfit to hide the naughty secret underneath. The skirt and thong pinched with every step, a constant reminder of my rebellion. I told myself I’d just take a walk, feel the thrill of being out in public with my lingerie hidden beneath.

I ended up in a quiet park, its paths lit by dim streetlights. The city was alive, but this corner felt safe, secluded. I was wrong. As I bent to pick up my phone, which slipped from my sweaty hands, my jeans rode down, exposing the tops of my stockings and the hem of the short skirt. Before I could cover up, a rough voice cut through the night.

“Well, fuck me, what’s this? A sissy boy sneaking around in a skirt and panties?”

My heart stopped. I yanked my jeans up and turned to face him—a man in his forties, clean-cut but with a wicked glint in his eyes, wearing a leather jacket and jeans. His smirk screamed trouble, the kind that thrived on control. I’m not remotely convincing as a woman—just a chubby guy with a plain face—but he saw right through me.

“It’s not what you think,” I stammered, backing away. “Leave me alone.”

He laughed, a low, mocking sound. “Oh, it’s exactly what I think, you pathetic slut. Pink thong? Stockings? A little skirt? You’re begging to be caught. Call me Daddy, sissy. That’s what filthy perverts like you need.” He stepped closer, towering over me. “What’s your sissy name? Don’t fucking lie.”

I shook my head, trying to sidestep him. “No, this is a mistake. I’m going home.” My voice was firm, but my hands trembled.

His hand shot out, grabbing my arm hard enough to make me wince. “You’re not going anywhere, Samantha—I’m picking that name for you, pretty little whore. Married, aren’t you? I see the ring. Bet your wife doesn’t know what a disgusting sissy you are.” His words stung, hitting too close to home. “Come with me to my place, or I’ll shout it to the whole park. ‘Hey, check out this pervert in panties!’ Maybe I’ll post a pic online for good measure.”

I pulled against his grip, panic rising. “Let go! I’ll scream for help.” But the park was empty, and the thought of Claire and the girls finding out paralyzed me. He dragged me along the path, his hold like iron, toward a nearby apartment building. I resisted, dragging my feet, pleading under my breath. “Please, I have a family. This isn’t me.”

“Shut up,” he snapped. “This is exactly you, sneaking out in lingerie and a skirt like a naughty slut. Keep fighting, it just makes Daddy’s cock harder.”

His apartment was a sparse one-bedroom—couch, TV, a faint smell of cologne. He locked the door and shoved me inside, pulling a coil of rope from a drawer—like he’d planned for this. “Strip those jeans off, Samantha. Show Daddy your slutty little outfit.”

I crossed my arms, shaking my head. “No. I’m not doing this. Unlock the door.”

He smirked, advancing with the rope. “Oh, you will, bitch. Or I’ll tie you up and make you.” I lunged for the door, but he was faster, wrestling my arms behind my back. I kicked and twisted, but he was stronger. He bound my wrists with the rope, tight enough to bite, then stepped back. “Now, parade around for Daddy. Tease me like the sissy slut you are. Shake that ass.”

I shook my head, tears prickling. “No way. Untie me.”

He grabbed my chin, forcing my eyes to his. “Walk, Samantha, or I’ll drag you outside like this. Let’s see how your neighbors like their sissy.” Defeated, I shuffled forward, the short skirt swishing against my thighs, stockings tugging with each step. I swayed awkwardly, feeling ridiculous, my face burning as he laughed. “That’s it, you desperate whore. Wiggle that sissy ass. Bet you love showing off for Daddy.”

He made me circle the room, catcalling and degrading me. “Look at you, sneaking around in that tiny skirt behind your wife’s back. Bet your stepdaughters would die if they saw you.” Finally, he pushed me to my knees. “Enough teasing. Time to get to work, slut.”

He unzipped his pants, pulling out his thick cock. “Suck it, Samantha. Show Daddy what a cock-hungry slut you are.”

I turned my head away. “No, I can’t. This is wrong.”

His hand gripped my jaw, forcing my face forward. “Open up, or I’ll make it hurt. Tell me you’re my naughty slut.”

The threat in his eyes broke me. “I’m… I’m your naughty slut, Daddy,” I whispered, parting my lips. He thrust in, rough and deep, making me gag. “That’s it, gag on Daddy’s cock. You fought, but look at you now—tied up and sucking like the worthless whore you are.”

I moaned around him, the degradation mixing with unwanted pleasure. His words poured out, humiliating me: “Bet your family thinks you’re a real man, but here you are, in a skirt and panties, my personal sissy toy.” He face-fucked me until tears streamed down my face, then pulled out, hauling me over the arm of the couch.

“Bend over, bitch. Time to fuck that sissy hole.”

With my hands tied, I couldn’t resist much, but I squirmed. “Stop, please!”

He pulled the thong aside, spat on his fingers, and probed me roughly. “Beg for it, Samantha. Tell Daddy you want his cock, or I’ll leave you tied here all night.”

The ropes dug in, the humiliation overwhelming. “Please, Daddy… fuck me,” I gasped, hating myself for it.

He entered me with a hard thrust, making me cry out. “Take it, you disgusting pervert. This is what you get for dressing like a slut behind your family’s back.” He pounded into me, grunting obscenities, his hands gripping my hips. The pain faded into pleasure, building until I came with a shudder, spilling into the thong.

He laughed, pulling out. “Look at that mess, Samantha. Lick it up, you filthy slut.” He scooped my cum from the thong with his fingers, smearing it across my lips. I gagged but obeyed, licking it clean, the taste bitter and humiliating. Then he stroked himself, groaning as he came, shooting thick ropes across my face. “Swallow it all, sissy. Every fucking drop.”

I opened my mouth, letting him wipe his cock on my tongue, swallowing the salty load as he watched, smirking. “Good girl.”

He tossed my jeans at me but didn’t untie me yet. “Stay there, Samantha. Daddy’s got a friend who’d love to meet a sissy like you. He’s on his way.” My stomach dropped as he picked up his phone, grinning.

To be continued…

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By *urious one400Man
7 days ago

dublin

Mmmm please keep going

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By *illhouseMan
7 days ago

Cumbria

Hot

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By *ssexNewSub OP   TV/TS
6 days ago

Coggeshall

Daddy lounged across from me, leather jacket open, smirking as he sipped a beer. “You’re gonna love this, Samantha,” he said, his voice thick with filthy intent. “My mate’s got a thing for pathetic sissies like you. Keep that skirt on and behave, or those pics I took go straight to your wife.”

I pulled against the ropes, heart pounding. “Please, let me go,” I said, voice hoarse from resisting. “I did what you wanted. I have a family.”

He laughed, low and cruel. “Oh, you’re not done, you naughty slut. You teased Daddy with that sissy arse, strutting around in that tiny skirt. Now you’ll do it for my mate.” He leaned closer, eyes glinting. “Say it—tell Daddy you’re his filthy sissy whore.”

I shook my head, defiance flaring. “No. This is enough. Untie me.”

He grabbed my chin, forcing my gaze to his. “Wrong answer, Samantha. You’re tied up, in a skirt and knickers, and you’re gonna take whatever we give you.” The door buzzer sounded, and his smirk widened. “Showtime, slut.” He buzzed his mate in, leaving me trembling on the couch.

Mike strode in—stocky, early forties, shaved head, tattoos snaking up his neck, dressed in a tight black shirt and jeans. His eyes lit up as he took me in. “Bloody hell, you weren’t joking,” he said, voice rough. “This sissy’s all dolled up and ready.”

“Meet Samantha,” Daddy said, yanking me to my feet. “She’s a married pervert who loves sneaking around in lingerie. Show Mike what you showed me, Samantha. Parade that arse.”

I stumbled, wrists still bound, and shook my head. “No, I’m not doing this. Let me go, please!” My voice cracked, but the thought of Claire and my stepdaughters finding out kept me from fighting harder.

Mike laughed, stepping closer. “Got some fight, eh? I like that. Get moving, sissy. Strut for us.” He slapped my thigh, making the skirt swish.

Daddy shoved me forward. “Do it, or we’re calling your wife. Or better yet, we’ll drag you to the town toilets—skirt up, tied up, ready for every bloke in there to have a go.” The image of a grimy public toilet in the town centre, men lining up to use me, made my stomach lurch.

I shook my head frantically. “Don’t… I can’t…”

“Then walk,” Mike growled. “And tell us how much you love being a naughty sissy slag.” Defeated, I shuffled across the room, the short skirt swaying, stockings rubbing against my skin. I felt ridiculous, my plain face and chubby body far from feminine, but their hungry stares twisted my gut with unwanted arousal. “That’s it, Samantha,” Daddy taunted. “Wiggle that sissy arse. Say ‘I’m a dirty sissy who wants to be fucked by two big men.’”

Tears pricked my eyes, but the words spilled out. “I’m a dirty sissy who wants to be fucked by two big men.” The degradation burned, my thong tightening.

Mike groaned, adjusting himself. “Good girl. Now beg us to use your mouth and arse. Tell Mike how much you want to suck his cock while Daddy fucks you, you filthy tart.”

“Please,” I whispered, stopping before them, “use my mouth and arse… I want to suck your cock, Mike, while Daddy fucks me.” I hated the words, but the threat of the town toilets or a motorway lay-by—tied up, skirt lifted for strangers—forced them out.

They positioned me on all fours, still bound, the carpet rough against my stockinged knees. Mike unzipped, his thick cock springing free. “Work it proper, sissy. No half-arsed effort. Show me you’re a cock-hungry slag.”

I leaned forward, taking him in my mouth, working slowly—tongue swirling, lips tight, trying to please. “That’s it, Samantha,” Mike groaned. “Suck like you mean it. Tell Daddy you’re his dirty little cocksucker.”

“I’m your dirty little cocksucker, Daddy,” I gasped between licks, shame and arousal mixing. Daddy moved behind me, flipping up my skirt and pulling the thong aside. He squirted lube on my arse, the cold shock making me flinch. “Say ‘Fuck my sissy arse, Daddy, I’m your filthy whore,’” he ordered.

“Fuck my sissy arse, Daddy, I’m your filthy whore,” I mumbled, still working Mike’s cock. Daddy thrust in, the lube easing the burn, and began pounding, his hips slapping against me. “Take it, you sneaky slag,” he grunted. “Tell Mike you love being spit-roasted like a cum-hungry sissy.”

“I love being spit-roasted like a cum-hungry sissy,” I moaned, voice muffled as I sucked Mike harder. Their taunts were relentless. “Bet your wife has no idea you’re such a whore,” Daddy sneered. “We could take you to a lay-by on the motorway—tied to a bench, skirt up for truckers. Say ‘Thank you, Daddy, for sharing my sissy arse.’”

“Thank you, Daddy, for sharing my sissy arse,” I gasped, the fantasy terrifying and thrilling. Mike’s breathing quickened, and just as he tensed, he grabbed my head, thrusting deep, cumming hard in my mouth. “Swallow it all, sissy,” he growled. I gagged but obeyed, swallowing the salty load as his cock pulsed against my tongue.

Daddy sped up, grunting. “Open your mouth, Samantha. You’re swallowing Daddy’s cum too.” He pulled out, moving to my face, stroking fast. “Say ‘I’m a cum-slut for Daddy and Mike.’”

“I’m a cum-slut for Daddy and Mike,” I whispered, opening wide. He came, hot ropes filling my mouth, and I swallowed every drop under his piercing gaze.

They stepped back, grinning, and Mike pulled out his phone. “Look at this, Samantha.” He showed me a video—me, skirt up, sucking Mike while saying I was a “dirty sissy” and “cum-hungry slag,” clips edited together to make me sound eager, desperate. “This goes to your wife if you don’t play nice,” Daddy said. “Next time, maybe it’s the town toilets or a lay-by.”

To be continued…

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By *ssexNewSub OP   TV/TS
6 days ago

Coggeshall

I knelt on the carpet of Daddy’s sparse flat, the taste of their cum still bitter in my mouth from moments ago. They loomed over me, grinning wickedly, their earlier threats of exposing me burning in my mind.

Daddy crouched down, his leather jacket creaking, his voice thick with filthy intent. “You’ve been a good sissy, Samantha, but we’re not done. Time to dress you up proper for more kinky fun.” He untied my hands briefly, tossing me a new outfit from a bag in the corner. It was a slutty maid costume: a black-and-white micro-dress, so short it barely covered my arse, with a frilly white apron tied around the waist; a black satin garter belt with cheap, shiny clips; and ultra-feminine pink French knickers, adorned with delicate frills that screamed girly. The knickers were soft, sheer, and embarrassingly dainty, clinging to my chubby, unmistakably male frame—a ridiculous man playing dress-up. “Put it on, slag,” he ordered. “Say ‘Thank you, Daddy, for my slutty maid dress and knickers.’”

I shook my head, panic surging. “No, this is too much. Please, let me go.” My voice trembled, but their video—clips of me begging and calling myself a cum-hungry sissy—kept me from fighting harder.

Mike laughed, his tattooed neck gleaming under the dim light. “Oh, you’ll wear it, you filthy tart, or we’re dragging you to the town toilets right now, dressed like a slutty maid for every bloke to see.” I fumbled, pulling the maid dress over my head, the garter belt snapping onto new stockings—shiny black ones that screamed whore. The pink frilly knickers slid up, their softness mocking my masculinity. Daddy fastened a pink leather collar with a silver ring tightly around my neck, clipping on a matching lead. Then Mike slipped a black blindfold over my eyes, plunging me into darkness. “Let’s take our sissy for a walk.”

I tried to pull back, stumbling as Daddy tugged the lead. “Where are you taking me?” I pleaded.

“Shut up and move,” Daddy snapped. “Say ‘I’m a naughty sissy who loves being Daddy’s pet.’”

“I’m a naughty sissy who loves being Daddy’s pet,” I mumbled, the words bitter, made by the threat of exposure. They guided me forward, the frilly dress scratching my skin, the girly knickers making every step feel obscene. I heard a door open, cool night air hitting me, and my stomach dropped. “No, not outside!” I gasped.

“Keep walking,” Mike growled, “or it’s the lay-by on the motorway—tied up, maid dress ripped, ready for truckers.” I heard gravel crunch underfoot, then the low hum of car engines. The lead jerked, stopping me, and rough hands pushed me to my knees on damp grass.

The blindfold came off, and I blinked, eyes adjusting to the glow of car headlights. I was in a secluded lay-by off the motorway, surrounded by eight men—strangers, their faces shadowed but eyes ravenous, some in work jackets, others in hoodies, circling me. The maid dress barely covered my thighs, the garter belt and frilly pink knickers peeking out, leaving me utterly exposed, the collar and lead marking me as their toy. My plain face and chubby body screamed pathetic man, making their leers even crueler. I froze, horrified.

“Look at our sissy maid,” Daddy announced, tugging the lead. “Samantha’s here to serve you dirty bastards. Tell them what you are, slag.”

I shook my head, tears welling. “No, please, not this!”

Mike grabbed my hair, forcing my face up. “Say ‘I’m a filthy sissy maid who needs all your cocks,’ or we leave you here for the next lot to fuck.”

“I’m a filthy sissy maid who needs all your cocks”. The men roared with laughter, zippers undoing, their voices thick with lust.

A wiry man with a scarred face stepped forward, cock hard. “Suck it, you pathetic maid. Serve like the cock-starved whore you are.” I leaned forward, trembling, and took him in my mouth, sucking slowly, tongue swirling. “Fuck, look at this slag,” he sneered. “Say ‘I’m a dirty maid who loves sucking strange cocks, Daddy.’”

“I’m a dirty maid who loves sucking strange cocks, Daddy,” I mumbled, shame burning. Another man knelt behind me, pulling my frilly knickers aside, lubing my arse before thrusting in hard. “Take it, you worthless sissy,” he growled. “Tell us you’re a cock-hungry maid who needs her holes filled.”

“I’m a cock-hungry maid who needs her holes filled,” I moaned, as another cock filled my mouth. They took turns, some fucking my arse, others my mouth, their dirty talk relentless. “You’re just a nasty sissy slut, aren’t you?” one spat, slamming into me. “Say ‘I’m a filthy maid who lives for cock.’”

“I’m a filthy maid who lives for cock,” I gasped between thrusts. Another jeered, “Bet your wife’d puke seeing you in that dress, begging for dick like a cheap tart.” The collar was tight on me as Daddy tugged the lead, urging them on. “Tell us you’re our cum-guzzling maid, Samantha.”

“I’m your cum-guzzling maid,” I whimpered, as one man groaned, pulling out to cum in my mouth. “Swallow it, whore,” he ordered. I did, the salty taste overwhelming, but another was already there, cumming across my face. “Lick it up, you disgusting slag,” Daddy commanded, and I obeyed, tongue catching every drop as they laughed. Three more used my arse, each cumming inside or on my maid dress, and I was made to scoop it off the frilly fabric, swallowing it all. “Say ‘I love swallowing cum for my masters,’” one demanded.

“I love swallowing cum for my masters,” I gasped, their taunts drowning me.

A broad man with a cruel smirk stepped up, unzipping and aiming a stream of piss at my chest, soaking the dress and apron. “Open your mouth, sissy maid,” he growled, then shoved his cock in mid-stream, piss hitting my tongue. “Drink it, you dirty fucking slag.” I gagged, as I swallowed the acrid flow, his cock pulsing in my mouth. Daddy yanked the lead. “Say ‘I’m a piss-drinking sissy maid who loves it.’”

“I’m a piss-drinking sissy maid who loves it,” I whispered, tears streaming as he kept pissing, forcing me to swallow. Two more followed, pissing on my face, my dress, my stockings, their voices vicious. “Look at this pathetic cunt, drinking piss like a proper whore,” one sneered. “Say ‘I’m a piss-slut maid for all you filthy men.’”

“I’m a piss-slut maid for all you filthy men,” I gasped, swallowing what I could as they cheered. Mike filmed it all. “Good sissy.”

When they were done, Daddy showed me the phone—clips of me sucking, swallowing cum and piss, begging in my maid dress, edited with my confessions. “This goes to your family if you step out of line, Samantha,” he said. “Now crawl back to the car.”

I crawled, dress dripping, collar tight, the lead dragging me forward. They drove me back, dumping me outside Daddy’s flat. “You’re our sissy maid now,” Mike said. “We’ll call.”

I stumbled away, the frilly knickers and maid dress clinging to me, mind shattered. I’d swallowed it all—cum, piss, shame. The video ensured they owned me, and the pathetic maid costume burned the truth deeper.

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By *seableMan
6 days ago

Halesowen

Wow. Excellent.

Love this.

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By *ita99TV/TS
6 days ago

bognor

Lucky Samantha

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By *imassagesharerMan
6 days ago

Northampton

Great, got me hard thanks

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By *ndstorm45Man
6 days ago

Wakefield

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By *ssexNewSub OP   TV/TS
6 days ago

Coggeshall

Thanks for the compliments on the story x

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By *suckMan
6 days ago

warminster

Love this story

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By *tillSissyMan
6 days ago

Bulwell

Jesus this is hot - the idea definitely gets me riled up, even if the reality would be terrifying...

Not going to stop going out in panties though.

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By *seekfunMan
5 days ago

stevenage

So hot

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By *rpcockMan
5 days ago

Orpington

Loving this

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By *ssexNewSub OP   TV/TS
4 days ago

Coggeshall

Thank you x

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By *akedTradesmanMan
4 days ago

watford

Please continue

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By *illmecreviceMan
4 days ago

Reading

Lovin it

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By *ature666Man
3 days ago

Wolverhampton

Oh fuck yes I've wanked twice reading this

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By *rixyessex2TV/TS
3 days ago

essex

Wooow fantastic story

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By *ohnny 51Man
3 days ago

Middlewich

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By *seekfunMan
3 days ago

stevenage

I want it to be me

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By *ym_ExplorerMan
3 days ago

Canvey Island

Where can I get humiliated and degraded like this? It’s got me so horny

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By *umslut7Man
3 days ago

dunfermline

Superb

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By *orth yorks guyMan
3 days ago

Castleford

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