First time with Daddy's Friend

T

By Thelma's boy

9/3/2025

first timecuckoldingblowjobdaddy's friendclub sexbig cock
Prompt: Her first big cock

The bass throbbed through the club, drowning out everything but the pulse between her legs. Rachel shifted on the barstool, her short skirt riding up, as she watched him walk toward her—tall, broad, and with a confident smirk that said he already knew what she wanted. He leaned in, the heat of his body pressing into her space. "You look like you need something to hold onto." His voice was rough, low, and she didn’t miss the way his jeans strained against the thick outline of his cock. She exhaled sharply, fingers tightening around her drink. "Maybe I do." "Then let's find out if you can handle it." His hand slid up her thigh, pushing her legs apart right there at the bar. A gasp caught in her throat as his fingers teased the edge of her panties—soaked already. She knew he was big, but the reality hit harder when he pulled her off the stool, her back pressing against the wall outside the bathroom. One rough tug of his zipper, and there it was—thick, veined, and straining toward her. "Open wide," he ordered, and she did, because she'd been imagining this all night. The first slick press of his cock against her lips made her whimper, but he didn’t wait—just pushed in, filling her mouth until her jaw ached. This was going to be a long night.

Prompt: Make it more explicit

His grip tangled in her hair, forcing her head back against the wall as he thrust deeper, the blunt head of his cock hitting the back of her throat. Saliva spilled down her chin, her gag reflex flaring—but he didn’t let up, just groaned low and filthy as her lips stretched around him. She tried to breathe through her nose, desperate for air, but he pulled out just enough to let her gasp before slamming in again, his hips snapping forward with ruthless precision. The taste of him—musky, salt-slick—flooded her senses. Her fingers clawed at his thighs, torn between pushing him away and dragging him closer. One hand left her hair, sliding between her legs to roughly palm her through her panties. She moaned around his cock, the vibration making him curse. "Fuck, that mouth," he growled, grinding into her lips. She could feel her own wetness soaking the fabric, slick against his fingers. He hooked the lace aside without warning, two fingers plunging into her. The sudden stretch made her jerk, but his grip in her hair kept her still, mouth stuffed full as he fingered her with rough, uneven strokes. Not enough—she needed more. And from the way his cock pulsed against her tongue, he wasn’t planning on stopping.

Prompt: He forced his cock into her tight pussy, tearing the tight opening making her cry out.

His fingers vanished from her soaked cunt, replaced instantly by the thick head of his cock pressing against her entrance. She barely had time to gasp before he shoved in hard, splitting her open with one brutal thrust. The stretch burned—her cry muffled against his shoulder as her nails dug into his back. "Tighter than I fucking thought," he gritted out, hips snapping forward until he was buried to the hilt. Her walls clenched around him, pulsing with the shock of being filled so completely. He didn’t let her adjust. One hand fisted in her hair again, yanking her head back as he pulled out halfway and rammed back in, setting a punishing rhythm. Each thrust dragged against her sensitive walls, the slap of skin echoing in the cramped hallway. "Take it," he growled, his free hand squeezing her thigh to hold her open wider. Her body trembled, oversensitive and aching, but he didn't slow—just fucked her deeper, harder, his cock hitting that spot inside her that made her vision blur. She came with a broken scream, her cunt clamping down on him like a vise. He groaned, hips stuttering as he pounded her through it, his own release building. "Gonna fill you up," he warned, voice ragged. And when he came, she felt every pulse, hot and thick, flooding her until it dripped down her thighs. He didn’t pull out. Just kept her pinned there, panting, his cock still twitching inside her.

She had sex before, but never before with such girth, and length. Ten inches was too much. She could feel the tear in her fussy sting, as he began to tuck her again.

His cock was still buried deep inside her when he leaned down, teeth grazing her ear. "You feel that?" he murmured, grinding his hips in a slow circle. "That ache? That's me *stretching you*." She whimpered, oversensitive and raw, but her body still clenched around him—betraying her, craving more. He chuckled darkly, pulling out just enough to make her feel every inch dragging against her swollen walls before slamming back in. Her breath came in ragged gasps. Even with his come still dripping from her, the stretch burned—his cock was *too much*, thick enough to make her muscles spasm in protest. But he didn’t care. Just hooked one of her legs over his elbow, forcing her wider, and fucked into her with deep, relentless strokes. "Fuck, *look* at you," he growled, thumb tracing where they were joined, smearing her wetness. "Taking it all like a good girl." She arched as he hit that spot again, her nails scraping down his back. The pain blurred into pleasure, her cunt fluttering around him as another orgasm built—helpless, inevitable. Then he shifted, angling deeper, and her vision whited out.

Prompt: She never had an orgasm before, the shock of ecstasy consumed her body.

Her back arched off the wall as the first real orgasm of her life ripped through her like lightning. Every muscle locked—toes curling, thighs shaking, cunt clamping down so hard she nearly sobbed from the intensity. His cock barely moved inside her now, her body milking him in violent pulses as pleasure burned through every nerve. "*That’s* what you’ve been missing," he rasped, gripping her hip hard enough to bruise as he ground deeper, letting her ride it out. She couldn’t speak—just panted, wrecked, her clit throbbing, her walls still fluttering around him. But he wasn’t done. His hand slid between them, fingers rubbing rough circles over her swollen clit. "Bet you can come again," he taunted. "Bet this greedy little cunt *needs* it." She cried out, oversensitive but helpless against the assault. His cock, his fingers—everything was *too much*, but her hips jerked into his touch anyway, chasing the next peak already. He laughed, low and dark, and fucked her through it.