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The Unexpected Date

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Matt Meets a girl named Kate at the gun club. They hit it off and decide to go on a date that evening. Little does Matt know that Kate is actually a transwoman who still has a penis. Kate goes home with Matt and seduces him.

Chapter 7: First Penetration

The steam still clung to their skin as Kate pushed Matt face-down onto the plush comforter. The clean scent of jasmine soap battled the lingering vanilla, a stark contrast to the raw intimacy simmering in the air. Her damp hair dripped cold droplets onto his back, making him shiver. She straddled his thighs, her weight a familiar, comfortable pressure. Her hand, warm and sure, smoothed down the curve of his spine, over the fading bruise on his ribs, then lower, fingers splaying possessively over the swell of his ass.

"Okay?" she murmured, her voice a low thrum against the quiet hum of the fan. Her touch was exploratory, kneading the muscle, tracing the cleft.

Matt turned his head, cheek pressed into the cool cotton. Her eyes, dark and serious in the soft lamplight, held a question that went deeper than the physical. He saw the flicker of hesitation there, the echo of a thousand unspoken rejections she braced herself for. The vulnerability beneath her usual confidence tightened his chest. "Yeah," he breathed, the word thick. "Yeah, Kate. Okay." He pushed his hips back slightly into her hand, an invitation.

Her exhale was audible, a release of tension. A smile, small and genuine, touched her lips. "Good." She leaned down, her lips brushing the shell of his ear. "Just relax, baby. Trust me." Her breath was hot, sending another shiver through him, different this time. Anticipation coiled low in his belly, a mix of nerves and sharp, undeniable want.

Her weight shifted. One hand remained firm on the small of his back, pinning him gently. The other, slicked with cool lube – coconut oil again, he recognized the faint tropical scent – found the curve of his ass cheek. Her fingers were deft, spreading him, exposing him. The air felt suddenly cooler there. He tensed instinctively, sucking in a sharp breath.

"Shhh," she soothed, her voice dropping to a husky whisper. Her slick thumb circled the tight furl of muscle, pressing gently but insistently. "Just breathe, Matt. Let go for me." The pressure increased, a persistent, intimate invasion. Her thumb pressed inside, just the tip, slick and stretching. He gasped, muscles clenching involuntarily around the intrusion. It burned, a sudden, shocking heat. "Easy," she murmured, her hand on his back rubbing slow circles now. "Just breathe through it. That's it. Good boy."

She worked him open slowly, meticulously. One finger joined the thumb, sliding deeper, the lube easing the way but not the intensity of the sensation. The stretch was profound, unfamiliar, demanding surrender. He focused on her voice, the rhythmic pressure of her hand on his back, the smell of coconut and her skin. Her finger crooked inside him, probing, finding a spot that sent a jolt of pure, electric pleasure through his nerves, chasing the burn. He cried out, muffled against the sheets, his hips jerking.

"Oh fuck," he groaned. "Jesus, Kate… right there…"

"I know," she purred, her voice thick with satisfaction. She pressed harder against that spot, circling it relentlessly. "Feel good? Tell me it feels good." She added a second finger, stretching him wider. The burn flared again, sharp, but the pleasure spiked harder, dizzying in its intensity. He was caught between the two sensations, panting.

"It… fuck… it does," he managed, pushing back against her hand, seeking more of that terrifying, incredible pressure inside him. "Don't stop."

A low chuckle vibrated against his skin. Her fingers withdrew slowly, leaving him feeling exposed, aching, and strangely empty. He heard the slick sound again, the unmistakable slide of lube on skin. He knew what it was coating now. Anticipation turned into a physical thrum in his veins. Her weight settled more firmly over him, her body pressing his down into the mattress. The thick, blunt head of her cock nudged against him, slick and incredibly hot, replacing the coolness of her fingers.

He tensed again, bracing. Her breath hit his ear, ragged and hot. "Relax, baby," she growled, the command laced with a desperate edge. "I'll make it good for you. Let me in." Her free hand gripped his hip hard, fingers digging in. The other guided her cockhead, pressing firmly against his resisting entrance.

The pressure was immense. Unyielding. He felt the tight ring of muscle strain, burn, threaten to tear. He gasped, a sound close to pain. "Kate…"

"Breathe," she commanded, her voice tight, strained with her own effort. "Push out. Like you're… fucking bearing down. Let me in, Matt. Now."

He obeyed, forcing his muscles to relax against every instinct screaming to clamp shut. He pushed out, exhaling hard. The pressure mounted, unbearable, then with a sudden, slick, burning pop, the thick head breached him. He cried out, a ragged shout, his body bowing under the invasion. The stretch was excruciating, filling him beyond comprehension. Tears pricked the corners of his eyes.

"Fuck," Kate gasped above him, her voice choked. "Oh fuck, you're tight… so fucking tight…" She held still, buried just by the head, both of them trembling, suspended in the shock of it. Her hand stroked his back frantically. "Okay? Breathe, just breathe. Does it… can you…?"

The burning stretch was still there, a deep, consuming ache, but beneath it… beneath it, the pressure was immense, filling, right. And that spot… it was right there, pressed against. He sucked in a shuddering breath, pushing back minutely against her. "More," he ground out, the word barely recognizable. "Slow… but more, Kate. Please."

A harsh groan tore from her throat. She pushed forward, a slow, deliberate slide, sinking deeper inch by agonizing, incredible inch. He felt every ridge, every vein of her cock as it stretched him open, the drag intense and overwhelming. She filled him completely, her hips finally pressing flush against his ass. She was buried to the hilt inside him. He felt impossibly full, stretched to the limit, pinned beneath her. The burn was still present, a low throb, but the pressure… the deep, anchoring pressure of her inside him… it was profound. He felt claimed, dominated, utterly hers.

"Fuck," she breathed, her chest heaving against his back. "Jesus Christ, Matt… you feel…" She trailed off, unable to articulate it. Her hips shifted minutely, a tiny experimental rock. The movement sent sparks flying up his spine, igniting that sensitive spot deep inside. A guttural moan escaped him, long and low.

She did it again, a slow, grinding rotation of her hips, pressing her cock hard against his prostate. Pleasure detonated, bright and shocking, drowning out the lingering burn. "Oh god!" he choked out, his fingers clawing at the sheets. "Do that… fuck, do that again…"

Her restraint snapped. She withdrew slowly, almost completely, the drag exquisitely torturous, then slammed back in with one powerful thrust. The bedframe slammed against the wall. Matt shouted, the sound ripped from his chest – a mixture of intense pleasure and the shock of the deep penetration. She set a brutal pace, fucking into him with hard, driving strokes, each one jolting him forward on the mattress, each one hammering against that bundle of nerves inside him. The wet slap of flesh on flesh, her harsh grunts, his own broken cries – the room was filled with the raw, urgent sounds of their joining.

"Take it," she snarled, her voice guttural, primal. She leaned over him, her teeth finding the healing bite mark on his shoulder, sinking in hard enough to make him cry out again, a sharp counterpoint to the deep, rhythmic pleasure-pain of her thrusts. "Take all of it, Matt. Fucking take me." Her hand slipped around his hip, finding his neglected cock. It was rock hard, leaking profusely. She gripped him tightly, her fist moving in rough counterpoint to her thrusts.

The dual assault was overwhelming. The deep, stretching fullness of her inside him, the relentless pounding against his prostate, the tight friction of her hand on his cock – it was too much, too intense. Pleasure coiled tight in his gut, a spring wound to breaking point. He felt out of control, lost in the sensation, pinned and used and utterly consumed.

"Kate!" he gasped, his voice breaking. "I'm gonna… I can't…" He was teetering on the edge, his body tensing, coiling.

"Look at me," she commanded, her thrusts never faltering, her grip tightening on his cock. "Look at me when you come."

He forced his head to turn, straining against the pillow. Her face was flushed, sweat-slicked, eyes blazing with fierce possession and raw need. Her lips were parted, panting. She was magnificent. Unstoppable. Hers. The sight, combined with the relentless stimulation, sent him hurtling over the edge. He came with a hoarse shout, back arching as much as her weight allowed, his cock pulsing thick ropes of come onto the sheets beneath him. His inner muscles clenched violently around her buried cock in involuntary spasms.

The sensation of him tightening, pulsing around her, triggered her own release. She cried out, a wordless, primal roar, burying herself as deep as possible inside him. He felt the hot pulse of her come deep within him, a searing flood that sent fresh shivers through his overstimulated body. She ground against him, milking her own climax, her teeth still locked on his shoulder as she shuddered violently above him.

Slowly, the tremors subsided. Her bite softened, releasing his shoulder. Her body slumped heavily onto his back, her breath coming in ragged gasps against his neck. She was still buried inside him, both of them sticky with sweat and come, trembling in the aftermath. The air hung thick with the smell of sex, coconut oil, and exertion.

Her weight, the lingering fullness, the throbbing ache… it was a profound, grounding exhaustion. He felt hollowed out, claimed, utterly spent. Her hand, sticky with his release, slid off his hip and flopped onto the bed beside him. One of her arms snaked under his chest, holding him close, her cheek pressed to the damp skin of his back. They lay tangled, breathing hard, the silence punctuated only by the fan and the frantic hammering of their hearts slowing down.

After a long moment, she shifted, withdrawing slowly, carefully. The sensation made him gasp softly. She rolled off him, collapsing onto her back beside him with a heavy sigh. She reached out blindly, her fingers finding his, lacing them together. Her hand was trembling slightly.

He turned his head. She was staring at the ceiling, her chest still rising and falling rapidly. In the soft light, he saw the sheen of sweat on her skin, the smudged remains of her eyeliner, the raw vulnerability in her eyes again, mixed now with a dazed wonder. The framed photos on the wall – glimpses of mountains, beaches, her grinning fiercely – seemed like artifacts from another life.

"You okay?" she asked finally, her voice hoarse and wrecked. She squeezed his hand. "That was… intense."

He squeezed back. Every muscle ached, especially his ass, a deep, satisfying throb. The bite mark pulsed on his shoulder. He felt raw, used, and utterly connected. "Intense," he echoed, a slow, exhausted smile spreading across his face. He shifted carefully, wincing minutely, and turned fully towards her. "Good intense. Amazing intense." He traced the line of her jaw with his free hand. "You?"

A shaky breath escaped her. She turned her head to look at him. The vulnerability was stark now, laid bare. "Terrifying," she admitted softly. "And fucking incredible." She searched his face. "You sure you're… not freaked?"

He leaned in, pressing a slow, gentle kiss to her sweat-damp lips. It was tender, grounding. "Positive," he murmured against her mouth. He pulled back slightly, meeting her gaze. "But I think…" he winced again, shifting his hips. "I might need a minute before I can walk straight. That coconut oil really did its job." A soft chuckle escaped him.

Kate laughed too, a relieved, breathy sound that transformed her face. Her thumb brushed over his knuckles. "Yeah," she agreed, her eyes warm. "Might need a minute myself. And maybe…" she glanced at the mess on the sheets, then back at him, a spark of familiar mischief returning to her eyes. "...another shower. Operation De-Coconut, Part Two?"

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