 |
By (user no longer on site) OP
4 weeks ago
|
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, 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. |
x