The late August sun hung low over the marshy fields in Essex, painting the grasslands in a hazy glow. Samantha, a 38-year-old man with a chubby frame, stubble rough on his jaw, and short, dark hair, clutched the leash of his dog, Rusty, with trembling hands. To passersby, he was just another bloke in baggy jeans, a faded navy jacket, and muddy boots, out for a dog walk. But beneath, his heart pounded with crippling anxiety and a shameful thrill. A pink thong with frilly lace clung to his small cock, the fabric teasing his sensitive skin, already half-hard despite his nerves. Sheer black stockings hugged his legs, and a short, pleated skirt swished under his jeans, a secret he hid from his family. These moments as Samantha, the woman he longed to be, were fraught with terror of discovery, her stomach churning with every step.
The field was secluded, bordered by a crumbling brick wall and sparse willows, seemingly safe for her secret. Rusty bounded ahead, sniffing the damp grass, and Samantha’s breath hitched, her nerves making her hands shake on the leash. When the dog squatted to shit, she muttered, crouching to fumble for a poo bag. Her jeans slipped, exposing the pink thong’s lacy edge, its frills stark against her pale arse. A cold breeze grazed her skin, and her small cock twitched, leaking precum into the lace as shame burned through her.
“Oi, you filthy sissy, flashin’ your knickers like a proper slag?” a rough voice sneered behind her.
Samantha froze, her heart slamming against her ribs, mortification flooding her. Her small cock pulsed, soaking the thong, even as panic made her dizzy. She scrambled upright, nearly dropping the leash, and spun to face a stocky man in his mid-50s, his belly straining a stained polo shirt, greying hair thinning, and a cigarette dangling from his smirking lips. His eyes, sharp and sleazy, locked onto the pink lace peeking above her waistband.
“Thought you could prance about in them frilly knickers without gettin’ caught, eh?” he said, his accent thick with mockery. He flicked his cigarette to the grass, crushing it under his boot. “What’s a shameful slut like you doin’ out here?”
Samantha’s face blazed, her voice trembling. “P-please, I—I didn’t mean for anyone to see—” she stammered, yanking at her jeans, her hands shaking so badly she could barely grip them, desperate to hide her secret.
“What’s your name, you pathetic bitch?” he demanded, stepping closer, his presence overwhelming.
“D-David,” she mumbled, her eyes glued to the ground.
The man laughed, a cruel, filthy sound. “David? Bollocks. A sissy in knickers like that’s got a proper slut name. Tell me your real name, or I’ll shout it to the whole fuckin’ field.”
Samantha’s stomach twisted, her nerves fraying. “S-Samantha,” she whispered, the admission burning her throat, her face flaming with humiliation.
“Fuckin’ perfect,” he sneered. “Samantha, the sissy slag. I’m Ron, and you’re gonna do exactly what I say, you tremblin’ little whore. Pull them jeans down. Now.”
Samantha shook her head, her voice cracking. “N-no, please, I can’t—” Her embarrassment paralyzed her, her hands frozen at her sides.
Ron’s grin turned vicious. “Don’t fuckin’ test me, sissy.” He grabbed her arm, yanking her closer, his fingers digging into her soft flesh. “Strip ‘em, or I’ll rip ‘em off myself.” Trembling, her breath hitching with panic, Samantha fumbled with the zipper, her jeans sliding down to reveal the pleated skirt, its hem barely covering her stockings’ lacy tops. She felt utterly exposed, her face burning as Ron’s eyes devoured her.
“P-please, don’t make me,” she begged, her voice shaking, tears pricking her eyes from sheer humiliation.
“Bend over, slag,” Ron growled, shoving her toward the brick wall. “Show me that arse and that pathetic little cock you’re hidin’.” Samantha stumbled, her nerves making her clumsy, but his rough push forced her to comply. She bent forward, the skirt riding up to expose the thong, its lace stretched tight over her small, rock-hard cock and balls, the frills framing her cheeks. Her body shook with dread, her cock leaking profusely, soaking the lace.
Ron groaned, his voice thick with lust. “Fuck me, look at you. A quiverin’ sissy with a tiny prick, drippin’ like a proper whore. Bet you’ve wanked yourself stupid dreamin’ of this.” Samantha whimpered, the humiliation crushing her, her cock pulsing despite her shame. Ron grabbed her chin, forcing her to meet his cruel gaze. “On your knees, Samantha. Right here in the grass. You’re gonna get my cock hard, you shameful bitch.”
Her breath came in panicked gasps as she sank to her knees, the grass prickling through her stockings. Rusty lay nearby, chewing a stick, oblivious. Ron unzipped his trousers, pulling out a soft, thick cock, dangling heavily before her face. “Go on, sissy,” he mocked. “Suck it hard, or I’ll make you sorry.”
Samantha froze, her nerves overwhelming her, her hands trembling at her sides. The sight of his soft cock, the musky smell, the fear of being seen—it was too much. “I—I can’t,” she whispered, her voice breaking, her face red with shame.
Ron’s eyes darkened. “Fuck your can’t,” he snarled, grabbing her short hair and yanking her face to his crotch, his soft cock smearing across her lips. “Open your fuckin’ mouth, sissy.” She whimpered, her lips parting as he shoved himself inside, the musky taste filling her mouth. She gagged, her nerves making her clumsy, but she sucked, her tongue working frantically to please him as his cock hardened against her lips, growing thick and veiny.
“That’s it, you pathetic slag,” Ron groaned, his hand tightening in her hair, thrusting shallowly. “Get it hard, you cock-hungry sissy.” Her spit coated him, dripping down her chin as she worked, her embarrassment peaking as his cock swelled. He pulled out with a wet pop, leaving her gasping. “Get up, slut. Bend over that wall. I’m gonna fuck that sissy arse.”
Samantha shook her head, tears of shame in her eyes. “P-please, no, I—I don’t want—” Her voice trembled, but Ron grabbed her arm, dragging her to the wall and forcing her to bend over, the skirt flipping up to expose her arse. “You don’t get a choice, sissy,” he growled, pulling a condom from his pocket and rolling it over his hard cock. He yanked the thong aside, exposing her tight hole, and spit on his fingers, smearing it roughly over her entrance. “This arse is mine.”
“Please, don’t,” she begged, her body shaking, but Ron ignored her, his dominance unrelenting. He thrust in hard, the condom-sheathed cock stretching her tight arse with a burning pain that made her cry out, her small cock bouncing and leaking onto the grass. Ron fucked her mercilessly, his hips slamming against her cheeks, each thrust driving her against the rough brick.
“Take it, you filthy sissy,” he panted, his hands gripping her hips, fingers bruising her flesh. “This is what you get for flauntin’ your knickers, you nervous little bitch.” Samantha’s body shuddered, her embarrassment and arousal colliding as his cock pounded into her, the lace thong rubbing her throbbing cock. With a moan, she came, her small cock spurting into the soaked lace, cum dripping through the thin fabric onto the grass below.
Ron groaned, his rhythm faltering as he neared his peak. “Not done with you yet, slag,” he snarled, pulling out and ripping off the condom. He grabbed her hair, dragging her to her knees. “Open your mouth, sissy. You’re gonna swallow every fuckin’ drop.” Samantha whimpered, her nerves screaming, but his grip forced her lips to his cock, still slick from the condom. He thrust into her mouth, rough and relentless, his cock pulsing as he groaned. “Take it, you pathetic whore,” he growled, and with a final thrust, he came, hot, thick cum flooding her mouth. She gagged, tears streaming from shame, but swallowed, the bitter taste coating her throat.
Ron smirked, noticing the puddle of her cum on the grass. “Look at that, you dirty sissy. Made a mess, didn’t ya? Get down there and lick it up.” Samantha’s face burned, her body shaking as she hesitated, but Ron shoved her face toward the grass. “Lick it, you shameful bitch, or I’ll make you regret it.” Sobbing with humiliation, she lowered her face, her tongue lapping at the warm, sticky cum on the grass, the earthy taste mixing with her degradation.
Ron laughed, zipping up. “Keep wearin’ them knickers, Samantha. I’ll find you again, you pathetic little whore.” As he sauntered off, Samantha collapsed against the wall, her body trembling with shame and ecstasy. Rusty trotted over, oblivious, as she adjusted her skirt and jeans, the soaked thong clinging to her skin, the taste of Ron’s cum and her own lingering on her tongue—a reminder of her exposure in the Essex fields. |
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