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Chapter 9
by
remysloane
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Claire: Ramya deflowers me
“Bleed for me.”
Powerful words from my mentor. She trails the dildo down my navel, resting the tip just above my clit, teasing, promising.
I gasp. “I don't know..."
"Come on, Claire, you got this."
"Oh my God… I want it to be you.”
“Is that a yes?” she asks, enthusiasm catching.
“Uh huh,” I breathe, lost in her eyes. “Do it now. Please.”
She squeezes my hand as we head into the bedroom. "Do you have lube? This is going to be a really tight fit."
“Of course,” I say, voice trembling.
The Vixen Outlaw will break me open. 8½ inches long, 2 inches wide. Dual-density silicone that feels like the real thing. I splurged for the best:

I’m naked on my back, legs spread wide on my own bed, heart hammering so hard I swear Ramya can hear it.
The room is bright. Ramya insists on seeing every detail of me, and I want her looking. The big black dildo rests on the nightstand like a promise I’m not sure I’m ready to keep.
Ramya kneels between my thighs, still in her bra and panties. It keeps just enough mystery between us. She’s calm and controlled, but her eyes are darker than I’ve ever seen them, and there's no doubt who is in charge.
“Relax, Claire,” she murmurs, voice low. “We’re going slow. No rush.”
Her fingers are warm and slick with lube, tracing my big lips like she’s memorizing them. I shiver when she parts me gently, exposing everything. One finger slides in easy, just as mine has many times before. But the second makes me tense. There's a stretch, and it hurts a little. I don't complain, but Ramya senses it's my first time with two fingers.
“Okay?” she asks, watching my face, then beginning to slowly work them in. “In my culture, two fingers is the test. If they fit too easily, you’ve already been penetrated. And no blood on the wedding night, no honor.”
The fingers slow in and out, slowly. I whimper, then joke through the stretch, “That's barbaric. So… did I pass?”
She smiles, eyes flicking up from my pussy. “You’re very tight. And I checked. Your hymen is intact. You're a perfect bride.” Then her voice drops, teasing. “But not for long."
I feel a fresh gush at that, my pussy clenching around her fingers.
“Tonight we're making sure you're ready,” she whispers, “Not for them. For you.”
She curls the fingers deep in me. "Holy shit!" I gasp. She's through the tight ring, pressing up against my G-spot. The pressure builds. The fingers start to feel really good.
She adds more lube, slides her fingers in at different angles, works me open until I’m panting, thighs trembling, pussy clenching around her fingers like it’s trying to pull her deeper.
“Good girl,” she breathes. "I think you're ready."
She withdraws slowly, reaches for the dildo.
I watch her coat it thick with lube, the black silicone gleaming, thick and intimidating.
She lines it up. The blunt head kisses my entrance, nudging my lips apart. My hole spreads around most of the wide head until I start to stretch. I'm nervous. My pussy clenches up.
She looks up from the dildo and smiles softly at me. "You're going to be fine. I promise it will fit. Just relax as much as you can inside and let me in."
"Uh huh. I trust you," I say, and I mean it.
She pushes. Slow, steady, no rush.
The thick head spreads me wide. My pussy flutters in painful spasms as it forces the entrance open, swallowing the crown with a burning stretch.
I gasp, back arching, hands fisting the sheets.
It burns.
It hurts.
The head is fully inside now, stretching me wider than anything ever has. The thick crown presses forward against that tight ring right at my entrance that's stubborn, thinned to its limit, refusing to let more in without breaking. My walls grip the shaft behind it, but the barrier still holds.
“Fuck,” I whimper. “It’s too big.”
She doesn’t stop. She inches forward, progress, the pressure builds.
"Ow. It hurts too much, Ramya," I plead.
She leans over me, one hand steadying the dildo, the other stroking my thigh. “You’re stronger than this.”
She's right. And I want this so bad. I want to be opened, I want to be filled. And most importantly, I want to experience it with her.
I bear down. The muscles in my pussy relax to accept her while I push my body to her.
The elastic ring snaps.
Pain flares white-hot, sharp enough to steal my breath.
My thighs quiver. I cry out, tears pricking my eyes as the thick head forces past the barrier. More of the thick shaft slowly slides inside.
Ramya pauses, buried just a few inches, letting me adjust.
I can feel the tear, I know that I am bleeding around the phallus.
“You did it,” she whispers, voice thick. “You’re not a virgin anymore.”
"Good," I say, forcing a teary smile.
She holds my gaze, then pushes again: one long, steady slide, inch by inch. Pain spreads deeper as my walls open around it. But it mostly hurts at the opening where I tore, where I will never tear again for any man.
Deeper. The dildo feels like it goes on forever. Then suddenly the base kisses my upturned butt cheeks. I feel every vein, every ridge, buried deep. It's incredible.
"Oh my God," I groan. I scoff, then I laugh, then I giggle. I don't know what to do or feel. I only know stuffed fullness. Pain merges with a weird, tingly sensation everywhere down there. The fat dildo reaches every rich nerve ending. My muscles flutter around it, spasms confusing pain and pleasure as I grip the strange intruder.
I am thoroughly and completely deflowered, an honor that should be bestowed on my husband. The regret leaves as fast as it enters. All I can think about is the woman between my legs that cares about me so much, and how I am so glad she was the one to do this.
"You are such a badass," Ramya says. "Well done. It definitely won't hurt as much next time,” she says softly, still inside me. “Now you’re open.”
We stay like that for a while with the dildo resting fully inside, my pussy clenching around it, pain fading into a strange, throbbing warmth.
"I'm so full, I had no idea it would be like this." I wince as something deep inside me aches, my body still adjusting.
I breathe through it, tears drying on my cheeks, feeling the fullness like a secret I can’t unlearn.
“Okay,” I whisper finally, voice shaky. “That's enough. You can take it out now.”
She withdraws slowly, carefully, the slick slide making me gasp again.
She sets it aside, then tugs at my lips to spread me gently with her fingers, inspecting clinically. I feel the changes at my opening. Cool air seeps in. I'm bigger, looser, and I can tell.
“Your hymen tore, and you're bleeding,” she says, matter-of-fact. "The hole is much bigger now. It looks like you will heal okay, though. It’s done. Congratulations.”
I feel exposed, ruined, strangely proud.
Ramya climbs up between my legs, hovering over me, her bra-clad breasts brushing my skin.
She looks into my eyes, serious and soft.
“I love you,” she says. Then she rolls her eyes with a crooked smile. "I'm not turning lesbian, don't worry. I just mean I love you, and I want you to know I’ll always be there for you."
My heart swells.
“Me too,” I breathe.
She arches her eyes playfully at me, and says. "I popped your cherry, Claire. Don't ever forget, I had you first."
I groan as my laugh causes one final adjustment in my hollowed-out pussy. I grin and poke her in the chest playfully. "You're a horrible influence on me. I'm glad it was you."
She laughs, kisses my forehead, and rolls off to lie beside me.
"Stay with me tonight," I ask.
"I'm not going anywhere."
We stay like that, quiet, her hand in mine, until sleep pulls us under with blood on the sheets and the dildo on the pillow next to us.
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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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