Chapter 5
by
remysloane
What's next?
Claire: My first anal
"Can you take it in the ass? You said I could fuck you, and I promise you won't get pregnant!"
I scoff, then laugh a little at that. "Are you serious?" I want to smack that smug look off his face, yet... I don't know. My head is a mess. I know I shouldn't feel this way, but I feel like I let him down because I couldn't take him vaginally. "I mean, I guess we can try. I've never done that before."
I reach next to my head and grab an extra pillow. "Get off me for a sec," I say, and he kneels between my legs as I lift up my butt to put the pillow under it. I spread my legs again, bending the knees back, really exposing my butthole to him.
Boss lady.
"Spread your cheeks for me, girl," he commands. I reach under my thighs and pull myself apart even more for him, distorting the flesh surrounding my anus and gaping my pussy slightly.
Then Mark leans down and licks all around my butthole. He even probes the tip of his tongue a little into the starfish, not quite opening me though, making me squirm a bit. Then he leans up again and spits and transfers it to the head of his cock that is still wet from my pussy and aligns the head against my puckered hole.
You can do this.
I've used various items from the produce aisle before and explored my nether regions while masturbating. I've actually had more self-administered girth in my butt than in my pussy. Nothing as big as the penis Mark is currently trying to shove in me, though. I know what I have to do.
Bear down. Push out to let him in.
"Oof," I groan as the head pops in, but again, he's thicker behind the head. Most men would quickly be balls-deep after the head is in, but not Mark. I have another mountain to climb. I take a deep breath, bear down again, and I triumph! The rubbery, tight grip of my anus slides over the hump and down around the thick shaft. "Arrrgh!" I moan, muscles in my legs and abs firing in protest. My anus flutters, spasms, and does nothing anymore to stop him. The remaining couple of inches of his thick cock easily slide home once the thickest part of him is in me. His pubic bone nudges my vulva to signal his conquest.
Holy shit.
"Fuck yeah, girl, that's the way."
It's a huge rush! My mouth hangs open in surprise. "Oh my God!" I scoff. It hurts, but not as bad as when he was trying to pop my cherry.
"That feels good, baby," he says as he pulls back and again drives it home.
"Uh.... Uh... Uh! Uh!" I groan with each pump. It doesn't take him long. The tightness, the warmth, the clenching muscles of a virgin ass that can't fully relax... all the things making it uncomfortable for me make it perfect for Mark. I don't know how many pumps I got. Less than ten for sure.
"Shit, coming!" he groans.
"Pull out. Mark, out!" I have little wiggle room from the bottom, but with him kneeling still and not on me, I am able to escape my hips to the side a fraction of an inch, just in time to look down and see his cock, pointing up, shoot his load onto my pubic area, splashing onto the labia. Then he grabs his cock and milks the rest of his load onto my belly.
I'm worried about the integrity of my bowels now. He gave me quite a stretch. Luckily, he wasn't in me long enough to fully relax my muscles and leave a gape. My butthole closes up, sealed safely tight within half a second of his cock's departure.
He's slapping the head of his softening cock against my clit like I'm a porn star. It's funny and harmless until I see one final glob of white goo ooze out the top just before he presses against my pussy and shoves in. There's enough hardness left to stretch and cause that burn again as he challenges my tightness with the head inserted. "Ow! Mark, no," I object, now also having to worry about the drop of semen he just put an inch into my pussy. And I am very fertile right now.
We lay together for a few minutes, then I wipe the semen onto my sheets, and he stands to get dressed. At least there's no awkward moment where I have to find a way to get him not to stay over. Although I'm also annoyed he doesn't at least ask.
"I'll show myself out," he says and leans down for a final kiss, but I can tell his heart isn't into it. I'm not going to hear from Mark again, and I'm okay with that. It might have just been my butthole, but Mark essentially did get laid, and it's off to the next girl for him. I could tell him my pussy is still virgin to coax him into coming back to finish the job, but I don't feel the desire anymore with him.
After he's gone and I'm alone, that's when I feel dirty and used. I'm so glad I didn't let him keep trying to fuck pussy without a condom. My butthole throbs from overuse while my pussy aches with denial, I'm a sticky mess, and the taste of his spunk has returned to my mouth, although that could be my imagination.
I feel better after I change the sheets, have an exorcism on the toilet, and take a long shower. Arousal returns as I think of what just happened, and I masturbate and get that orgasm that my partner failed to deliver. I slip a finger into the hole after. My pussy was never sore after he stopped trying to cram his cock into me. I never saw any blood either. And even though I wanted him to fuck me in the heat of the moment, I'm grateful he didn't. I guess I am still a virgin.
Well, not exactly still a virgin, I correct myself.
Half a virgin.
Sacrificing my bum to save my pussy:

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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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