Annie's POV, Part 5

Author's Note: I assume y'all are enjoying this, but if it's getting old and you'd prefer new content, feel free to let me know. Won't hurt my feelings.

Also FYI this chapter contains anal and large anal insertions. And to those of you who care about this sort of thing, in my stories, everyone is inexplicable clean down there when it comes time for sex, because who has time to get an enema beforehand, right?

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"So," Annie asks, still a little short of breath. "How does it feel to have my rich, fertile futa cum inside you? Do you feel like a good little cumdump?"

"It feels perfect, like this is how I meant to be. I can't wait for Sam to come in and make me pregnant."

The thought of poor, tiny-dicked, blue balled Sam waiting outside makes Annie both horny and guilty all at once.

"Well now hold on there, sister. We've got another eleven orgasms to pack into that cunt of yours first. And don't forget you wanted anal."

Lily blushes at the reminder, but Annie can see her pussy twitch with excitement.

"Should we go ahead and do that now? You said I'd need some preparation."

"Yeah, that part may take a while. But first, we've got a scoreboard to update. Now, how times did you cum?" Annie says with a grin.

Lily groans and her face turns redder. "T-twenty-two I think."

Annie can't help but whistle with surprise. Even for her, twenty-two orgasms in one session is a record. Then again, Annie's never had sex with a virgin before. Especially not one in her early twenties. In a world full of horny futa, most women lose their virginity as soon as they're eighteen. Lily must have been very, very repressed.

Of course, after today, she'll count as an experience woman, and Annie is all too thrilled to make that happen. Picking up the sharpie, she updates the score on Lily's back. It's now 27 to 2.

"Alright honey-buns, get on all fours, doggy style. We've got to work on that ass of yours for a while."

Lily complies while Annie digs the cabinet for some "tools" and grabs more lube.

"Alright slut," Annie says, trying to sound forceful and little mean. "Face down, ass up, and spread those pretty ass cheeks."

Lily complies silently, showing off her tight, puckered asshole. On a whim, Annie slaps her ass hard. Lily gasps with shock and pain.

Annie takes the lube and starts applying a large amount to Lily's ass. Much of it goes over her cheeks, giving them a wonderful shine in the hotel room lights, but more than enough get's rubbed into her virgin asshole. Everything's ready for the first penetration of Lily's butt.

"Beg me for it."

"what?" Lily asks, seeming confused.

"Beg me to ravish your virgin ass, you little whore."

"Please Annie, please fuck my slutty ass."

Annie slaps her butt again. "Not good enough."

Lily takes a deep breath, then says:

"Please Goddess Annie, take my asshole as you've taken the rest of me. Stretch me out and ruin my body. Make me your obedient, stupid cumdump!"

Annie notes that this line has really gotten the waterworks flowing between Lily's legs and smiles.

"As you wish."

Annie inserts her pointer finger into Lily's ass and starts to work it around, slowly pressing and twisting and loosening her friend's tightest hole. She can feel Lily tighten her sphincter with each twitch.

"Relax, slut. This will be easier if you relax."

Between her own ministrations and the relaxant in the lube, Lily loosens pretty easily, and soon Annie judges her ready for another finger. As her middle finger joins her pointer, she asks:

"Does this hurt?"

"A little...but I like it."

Annie grins. It figures a submissive little slut like Lily would get off on the pain. She's already made a sizeable wet mark on the bedsheets. Annie decides another finger is due.

"Eeeep." Lily squeaks as two becomes three. As Annie finger-fucks her friend's rectum, she notices Lily's breath start to pick up and her hips start to buck, pushing backward onto Annie's fingers. Annie starts to get a little more forceful, a little rougher, and then:

"Gappphhhh." Lily cries out, muffled by her face in the mattress, and has her twenty-eighth orgasm of the day, her anus tightening against Annie's fingers as the pleasure rocks through her. Once she's finished cumming, Annie takes that as a sign that Lily's ready to move up to the next step. Toys.