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Chapter 20
by
remysloane
What's next?
Claire: fucking Ramya through pain to pleasure
Every inch of the long "Outlaw" dildo is buried in my mentor's virgin pussy. I spread her cheeks with my hands and grind my hips to make sure I'm in all the way, the dildo's fake balls rubbing against her clit. Her dainty starfish is distorted, the thick dildo in her pussy stretching the skin at the anus too. Silky black hair lines her butthole and poofs out around the dildo in all directions from her stuffed pussy. Blood smudges have spread to her inner thighs and my pubic mound from the exciting deflowering I never would have guessed was necessary until Ramya confessed her innocence.
I stay buried deep inside Ramya for a long moment, savoring the way her freshly opened pussy flutters around the massive toy.
Then I pull out slowly, watching her small inner lips cling tightly to the shaft, pulling her inside out. The ridge of the head catches on her tightness before suddenly slipping free with a wet, hollow popping sound. I keep her muscular ass cheeks spread and add my thumbs near her crack, holding her obscenely open.
The sight makes my breath catch. Where there had once been a tiny, perfectly sealed hole ringed by a thick hymen, there’s now a big, puffy gape. I can see deep into the hole and the slick, ribbed pink flesh along her stretched canal. Her thick hymen is completely gone, torn apart and left in tiny tabs.
“Your pussy is huge now,” I taunt softly, voice thick with satisfaction. “That perfect little virgin pussy you guarded for so long is completely ruined. You’re gaping for me, Ramya. I did that to you.”
She whimpers, trembling under my hands. The dark possessive thrill mixes with a quick flicker of sympathy since she really had been saving herself. But it passes fast. I want her too badly. And if she had won, I'd be on my hands and knees with my pussy gaping for her.
I help her up. She walks toward my bedroom bow-legged and unsteady, red smudges of her virgin blood visible on the undersides of her ass cheeks. The sight keeps me wet in the harness.
“Stretch out on the bed,” I command gently but firmly. “On your back.”
Ramya obeys, crawling onto my clean white sheets and turning to her back, her tits jostling. I smile. She's already leaving faint red streaks on my sheets under her bum. She draws her knees back before I ask.
Even without me spreading her lips, she’s still gaping a little at the bottom of her tiny, hair-fringed slit. She might never fully close. The thought that I've caused permanent changes to my mentor's body sends another hot rush through me.
I move between her spread thighs and add fresh lube to the dildo. Streaks of Ramya’s virgin blood are still visible on the dark shaft. I penetrate her slowly and carefully, triggering an adorable pussy queef as the last two inches slide inside. I settle into a very slow, full tempo. Being able to look into her eyes in missionary changes everything. I become more tender, reading every moan and expression. It still hurts her, but she’s starting to enjoy it.
Her tightness is incredible. I have to push with real power just to sink the thick dildo deep, even though I've already been fucking her for a while after popping her cherry. It’s nothing like the much looser asshole of the guy I pegged last night for practice. Ramya’s pussy grips me like a hot vice, resistant and delicious. Since I’m not moving fast enough to make those large, sagging breasts bounce, I reach down, clasp them, and roll her nipples between my fingers while kneading the soft flesh.
Our eyes lock, hers still shiny and red from the trauma of her deflowering. The intense eye contact hits me hard. This isn’t just claiming my mentor anymore. Months of trust, late-night talks, and that strange bond we built… it all surges forward. I feel something deeper while I’m buried inside her. I love her. I’m certain of it. It might not be romantic love. I don’t know how to label it. I just know I care more for this woman than anyone right now, and I’ve never been this turned on in my life.
"Is that too deep?" I ask softly. "You're taking it all, but I can hold some of it back if it helps."
She shakes her head. "It's no problem."
I lean down, needing more. She turns her head at first, ****, lips pressed tight. I kiss the corner of her mouth, her cheek, then back to her closed lips, persistent but tender. I earned the right to fuck her, but she has to want to kiss me. I wait patiently, hips rolling in those slow, powerful, full strokes.
Finally she gives in and kisses me back. What begins hesitant turns passionate fast. Our tongues meet, wet and hungry, matching the slick rhythm of me stretching her ruined pussy. I settle my weight on her chest and feel her heart racing against mine, just like when we were grappling.
While kissing her deeply, I confess against her lips, “I’ve never had this much fun in my life.”
Ramya surprises me by pulling back just enough to giggle and whisper, “Surprisingly, me too.”
That admission makes me grin against her lips. “Good,” I whisper, voice husky.
At the end of every pump, I roll my hips forward and grind firmly, and a sharp, electric jolt shoots through me. The harness straps pull everything tight, keeping the dildo’s base nestled right against my large clit, giving me delicious indirect pressure with each movement. The pleasure builds steadily, and my own orgasm hovers just out of reach, fed by the sight of Ramya beneath me, the wet sounds of her ruined pussy taking my cock, and the intimate press of her racing heart against mine.
“Does it still hurt?” I ask softly.
She nods, then adds, “But it feels good too.”
Energy surges in me even though I was a sweaty, exhausted mess from the fight just minutes before. It's like that never happened. I pick up the pace a little, her incredible tightness yielding slowly to my relentless attack. I lift my chest just a little so I can feel her breasts start to move beneath me. After a minute I tell her, voice low and sincere, “I want you to come for me, Ramya. Tell me how to get you there. You can touch yourself while I fuck you. I'll even go down on you after if that's what it takes."
She looks up at me, eyes hazy with pleasure and lingering pain. “Just keep fucking me. I'm almost there,” she replies, surprising me again with her confidence.
Her words light a fire in me. I keep the eye contact, keep kissing her, and work her with those steady, full strokes. Her heavy breasts bounce gently beneath me. Her breathing gets ragged. Her thighs start trembling around my waist.
"Yes... Yes..." she moans. Her legs straighten and cradle my thighs, and she lifts her butt and angles her clit against the dildo. "Yes! Coming, Claire, fuck me!"
Her pussy clenches rhythmically around the massive dildo, fluttering and squeezing as she gasps into my mouth. Her whole body shakes with the **** of it. I ride her through every wave, whispering praises against her lips.
I'm so close, and I'm **** for my own sweet release. As Ramya's orgasm winds down, I reach to the side and loosen one of the harness straps, the dildo still buried in my lover's pussy. Space opens up at my crotch, and I slide my hand under the dildo and rub my clit.
"Grab my breast," I command. "Pinch a nipple. Yes, like that. It won't hurt."
With my fingers frantically rubbing my clit and Ramya pinching my nipple hard, my own orgasm crashes over me like a thunderclap. I moan into her mouth as powerful waves roll through my body, my hips jerking against her.
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A Tale of Two Virgins: Hallowed to Hollowed
Two untouched pussies: one Baptist guilt trip, one arranged-marriage obligation, and a single forbidden craving.
Two horny virgins arrive in the city with the same secret throbbing between their thighs. One a tall, shy Midwest girl whose untouched pussy aches at the thought of finally being split open by a thick black cock; the other an ambitious corporate executive, a golden-skinned Indian beauty who swallows and takes it up the ass but still guards her hymen, the final bargaining chip for an arranged marriage. They can become mentor and mentee, trading filthy advice and trembling fingers, learning exactly how far they can stretch without breaking the seal or letting a real man inside, until the night one of them finally spreads wide and begs to be ruined. Choose Claire’s blushing surrender, Ramya’s undisciplined fall from grace, or let them drag each other across the line together. Every path ends the same: legs spread and innocence shattered. Who will bleed first?
Updated on Jun 10, 2026
by remysloane
Created on Jan 14, 2026
by remysloane
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