Unfortunate Timing

I turn my attention back to Penny. I slip my finger out of her pussy and hold it up for everyone, especially Melanie, to see the thick layer of sticky honey clinging to every bit of it.

Penny's bottom is firm enough that simply spreading her feet was enough to gently pull her hard cheeks apart a little bit. Enough for me to see the egg-shaped dark swath of purple-brown skin just above her pussy as it disappears into the wide cleft between her globes. Its color blossoming from a faint tinge at the outer edges to a deep hue as it comes to the tight, and small, pink ring of her asshole. I touch the tip of my finger to Penny's asshole, my slender finger covering the tight ring of firm muscle. Even with Penny reflexively clenching her muscle tight, I can feel the gentle wrinkles of her flesh as they flow inward and disappear into the deep pinpoint opening.

Penny quivers nervously. And she stays very still, feeling the slight pressure of my finger against her last private place. The one part of her that's still unknown to anyone else. The one part she desperately wishes to keep to herself.

"If you were skanky enough to have allowed that loser to use your filthy butt, you'd never admit to being that much of a gutter whore, bitch. I will see for myself if you were that trashy and stupid. You may behave your slutty self by inviting me into your butt and it will not be uncomfortable for you. Or not. In which case I'll just shove right in any way. And I'll tell you now, I don't care if you want this to be easy or hard on you. Either way, I won't feel it. Now be a good butt slut. Take a deep breath, then push hard like you're trying to use the toilet. Push as hard as you can. That will force your reluctant little ring to relax. Keep pushing until you've swallowed all of my finger into your butt."

I wiggle the tip of my finger slightly. "now, bitch." I allow Penny about one second to follow the advice I've given her. I hear her suck in a very fearfully panicked breath. I feel her tense muscle loosen, but not fully. I allow her another second until her muscle has relaxed about half of what it could. Then I press firmly.

In a fraction of a second, I feel the dense ring of muscle begin to stretch wide as my finger pushes it inward. In another fraction of a second, I feel the muscle stop moving inward. It's hard rubberiness yields. In that instant the tip of my finger slide in. Immediately her muscle turns to a steely hardness and clamps down tight on my finger. Penny screeches a strained, "OOH!" that half sounds like she's crying.

I decide to show her a trace of mercy. I stop, holding my finger still in place. Her muscle locks around it. I scold her to relax. She trembles nervously. Then I feel her trying to relax. At first, her muscle pushes back. Then it loosens back to its former rubberiness. "Harder, bitch!" I snap firmly. I feel her ring loosen a bit more so that it feels more like a rubber band squeezing gently around me. And then, without my having to push any harder, my finger starts sliding deeper into her. Almost instantly I feel the pressure vanish from the tip of it as my finger slips past her muscular ring.

Penny chants "UH! UH!" over and over, her groans as panicked and nervous as they are fast. Her ring stays loose around me, though I can tell it's taking her a lot of effort to allow it.

As small as I am, I don't have too much finger to put into her. It only takes a few seconds for the web of finger to find Penny's ring. It stops moving. "In. Just breathe and relax, bitch."

Penny pants almost hyperventilates. She quivers slightly. I feel her asshole tense up around the base of my finger. For a split second, it squeezes me with all its might, then loosens to what I'd guess is its normal tightness for unwelcome situations. In another fraction of a second, I feel teeny little quivers start flowing through the muscle.

I pretend to ignore Penny. Beside her, Bryce obediently sits on the sofa. He doesn't dare turn his head. But he does keep shifting his eyes towards Penny just long enough to catch a fleeting glimpse of the naked girl. Judging by the angle of his eyes, I'm pretty sure they keep heading straight for her breasts. What a man! Okay, Penny's modest breasts hang loose and free from her chest. Okay, their pointy little tips have a sensual roundness to them with her nipples swollen so hard. Okay, her mounds are pert, and now they dance seductively as her body trembles. But still, I didn't give him permission to look at those breasts!

I pretend not to have noticed as I return my attention back to Melanie. "Do you think this skanky bottom is a virgin or a slut?" Melanie answers that she thinks it's a virgin although her voice, and the look on her face, tells me she's less sure and more hopeful that it is.

I do three things. First I smile. Second I answer, "You guessed correctly, slut." Third, I use the tip of my finger to press very gently downward. The paper-thin sausage-casing like membrane of Penny's bowel does nothing to block me from feeling the spongy softness of Penny's pussy walls. Immediately I feel the twitches sweeping along her walls just as sharply as I did with my finger in her pussy. And I definitely feel the heat.

Instantly Penny squeals a very nervous "YE-EEEEEE!" drawing it out for several seconds. While Penny squeals, her bottom frozen hard, and still, I use my finger to tenderly caress the backside of her pussy wall with a slight, gentle pressure. Penny's asshole clenches to steely tightness around my finger, locking it in place and crushing it with all its strength.

It takes four or five seconds for Penny's mind to accept that this isn't hurting her. Once she does, her panicked squeal fades away, only to be replaced by soft purrs of "MM!" As Penny begins purring, I feel those icy hot sparks begin erupting along her meaty walls anew.

I pretend not to notice. I start asking Melanie more questions, even as my finger slowly massages inside Penny. I ask Melanie if she thinks a good mother should teach her "little girl" about sex. Yes. If she thinks a good mother should know the boys in her girl's life. Yes. If a good mother should help her girl to chose a proper boyfriend. Yes. I repeat the questions, this time asking if Melanie has done it. She answers a very embarrassed "no" to all of them.

Now I ask Melanie if she thinks Penny is "grown-up" enough to have sex. Very reluctantly, Melanie admits that the 18-year-old Penny is. I ask Melanie if she thinks Penny's pussy is "excited" and would enjoy some "manly attention" tonight. One glance at the glistening wet pussy lips, one whiff of Penny's perfumed muskiness, one hint of the sultry purrs coming from her lips, and it's undeniable. Melanie has no choice but to admit Penny is horny. "Well, this filthy tramp has already turned itself into a cheap little whore, hasn't it. It's not like we can re-virginate it back into an actual woman with some shame, is it?" I tell Melanie in a rather taunting voice. Melanie has no choice but to concede there's no returning Penny to maidenhood.

I ask Melanie if she thinks the almost-20-year-old Bryce is aa decent boy for Penny to be dating. Melanie says she doesn't know, she's never heard of him before tonight. "Well, that's because you've been a negligent mommy. Otherwise, you know where your little slut is slutting around." I ask again, forcing Melanie to answer with only yes or no. She very reluctantly says "yes." From what little I've heard about him, I wouldn't let him date my whore, Paige. Then again, I have high standards. Even though Bryce isn't a bad guy, and he has realistic goals for his future by which he might actually be able to support a family.

I ask Penny if Bryce has been kind to her. Penny answers with a very throaty, "Yes, Ma'am," breathed out over her deepening moans of "MM!" I ask her to tell me all about their date tonight, in detail. I want to know everything Bryce did and said to her so I can decide for myself if he's treated her like a girl, or like the cheap whore she is. Penny's answer takes a few minutes, her voice breaking so often as she cries out a sultry moan. As she describes Bryce being sweet to her I feel Penny's asshole start twitching lightly around my finger. And I see the heavy film of honey clinging to her lips finally make it to the crease of her thighs. She quivers, too.

After Penny's done, I turn back to Melanie and ask her if she thinks Penny is horny enough that it will take a good fucking to fully satisfy her. With Penny now moaning loudly and quivering, there's only one answer for Melanie: yes.

I ask Penny "Would you like to be fucked like the skanky gutter whore you are tonight, bitch?" Yes. "Would you like Bryce to give you some dick tonight, bitch?" Yes. "Does Bryce have enough dick to satisfy you, bitch?" I'm sure he does, Ma'am! I ask her how much dick she wants. All of it! I ask her how she can be so sure Bryce has enough dick to "stuff that skank pit full and actually make it cum?" I don't know, but I'm sure he does, Ma'am!

I shake my head. I ask Penny if Bryce wants her skanky body. I hope so, Ma'am! I ask her if she's offered it to him, adding that cheap whore tend to do skanky things like that. No... not in words, Ma'am! I ask her if Bryce has seen her skanky-self naked. No. I ask her if she wants to show her body off to him like a gutter whore would. Yes. I ask her if she wants him to see how sloppy wet her pussy is with her stinky skank. If he wants to, YES!

I wiggle my finger just a little more. It's enough to make Penny suddenly blurt out a squealing hot moan. I keep wiggling it to keep Penny shrieking those so-hungry-for-a-fuck moans.

I turn back to Melanie and ask her if Bryce "is man enough to take care of the little slut." Melanie cringes hard and reluctantly says "yes." I ask her how she knows. She admits she doesn't. I ask her if she thinks a good mother should "know" her little girl's sexual partners. She says "yes." So I ask her what kind of a lover Bryce is. She tells me she hasn't a clue. "So you don't know if he'll take good care of your baby slut, or trick her out on the corner, do you?" Melanie shamefully admits she doesn't. So I ask her if she thinks a good mother should know these things before whoring out her little girl to just any old cock that comes along." Melanie says "yes." Then again, what else could she say, especially when I phrased it like that?

I use the backs of the fingers on my free hand to tenderly stroke along Penny's outer lips. With the gash between them, my fingers brush along the edges of her pink folds as well. And occasionally over the rock-hard nub of her clit. I make it a point not to shy from any of it. "Bitch..." I coo with my voice so sweet, "Since you want to be such a little slut tonight, I guess we should start by showing that skanky body to this boy and seeing if he's willing to touch something so gross, don't you think?"

"Yes, Ma'am!" Penny cries out, her voice all-moan, and all thrilled by the prospect.

"And then... If he can stand to touch it, maybe mommy will be nice and decide if this boy is man enough for a cheap gutter tramp! Would you like mommy to decide if he's man enough for your skank pit?"

"Yes, Ma'am!" Penny blurts hopefully enthusiastic.

I slide my finger out of Penny's bottom. Penny stays still and relaxed for it without my having to tell her. As I slip from her snug ring, Penny pants fast breaths of frustration. She fidgets around even though she stays obediently bent over.

I have Penny stand up. Then I have her stand in front of Bryce, her hands at her side. As she faces him, I whisper to her. She promptly asks him, "would you please look at my naked body, Sir, and tell me if you'd like to have it for your pleasure tonight, or if I'm just too skanky for you, Sir?"

Penny smiles wide, her grin as hopeful as it is nervous. She turns slowly in a circle. Penny pauses with her bottom toward Bryce. She leans forward, bracing her hands on her knees as she pokes her butt out to him. With her legs slightly parted, it also displays her pussy to the boy. Penny gives him a slow, seductive, and fairly amateurish, wiggle of her bottom. Then she straightens up and finishes her turn.

Again facing Bryce, Penny improvises. She wiggles her chest slightly. It's enough to make her breasts dance as they stand out from her chest. "Sir, is this skanky body acceptable to you?" Penny asks very nervously.

I snap my fingers, turning to Bryce and quickly telling him "just nod or leave, sissy."

Bryce nods rather eagerly.

"Then please, Sir, will you please take this slutty body and use every last bit of for your pleasure, Sir?"

Bryce doesn't give me a chance to do anything. He's nodding vigorously long before Penny is done offering herself to him.

"Go kneel in front of your mommy, bitch." I firmly instruct Penny.

Chapter 3:

Help From Mom

Penny hasn't a clue what I mean for her to do when I tell her to kneel. She starts by simply getting down on her knees, her posture rather casual. I quickly scold her, my voice firm but also warm, to spread her knees and feet wide. She's already sitting back with her bottom over her heels. Opening her legs leaves nothing to hide her pussy. Then I have her straighten her back up until it's rigid and put her hands at the small of her back. It leaves her chest wantonly displayed. I have her look forward. Kneeling in front of her mom, who sits on the barstool, it has Penny staring at Melanie's knees.

"Clearly you are hideous at choosing a sex partner, bitch." I use my taunting mean-girl voice now. "Otherwise you'd still be pure. And a proper woman. But instead, you've managed to make yourself into a rather disgusting filthy little gutter whore. Too bad for you I don't need any more whores in my realm. There are plenty of vacant street corners you could work."

I sigh deeply and unhappily. "It's time for you to learn how to be an actual woman. You will very politely ask mommy to judge whether or not Bryce is an appropriate sex partner for you. And if not, you will definitely be diddling that skanky thing for the foreseeable future. Oh, and you will be extremely polite when you ask, bitch." I cross my arms over my chest, glare down upon Penny and tap my foot. It's my best impatient look.

Penny cringes. "Mom... will you please... let me be with Bryce?"

"Bad bitch!" I snap instantly. "Am I going to have to whip that fake humility out of you?" I sigh and then continue on, my voice now more that of a teacher than scolding. "I said ask her to determine if he's an appropriate sex partner for you. I did not say to just as if you could go on being a little slut. Haven't you ever asked humbly for anything in your short life?

"This is what you are going to do. First, apologize to mommy for being such a little slut. Then tell mommy that your pussy is very horny. Then tell mommy that Bryce is willing to fuck that skanky thing. And then, ask mommy very sweetly to ensure that Bryce is man enough to satisfy your sluttiness. Now, bitch."

Penny gasps as she cringes harder. Her voice mutes to where I can barely hear her. And it takes on a slight squeakiness. Shyly, Penny begins. "Mom... I'm sorry that I'm a total slut... but I am just so horny right now! I mean like it's all I can do not to run off and... fix it... alone. Bryce... wants to help me... take care of it... would you please... please... is Bryce... a good enough guy for me?"

"Bad bitch!" I snap more sternly, still not raising my voice. I spend two entire minutes scolding Penny for her fake modesty. "You weren't so shy when you were giving that skank pit to that snake, were you? No, you just got naked and offered it up like a cheap whore. No reason to be shy now, bitch! Now ask right."

Penny's voice drops and breaks as she asks Melanie to "Decide if Bryce is man enough to take care of her "slutty itch."

I decide that's shameless enough. I turn my attention to Melanie, who already looks more uncomfortable than ever. I ask her "did you get a very good look at Penny's little skank pit?"

Melanie knows well that I won't tolerate any answer except yes or no from her. I've already warned her of that. She stutters a few times, trying to decide which to answer. How much of a look is a good look? What should she have been looking for? Knowing that she tried hard not to really look at Penny's pussy at all, Melanie finally answers "no." Smart woman. She just saved herself a spanking!

"Penelope, get up and show mommy your pussy, bitch," I say.

Penny nervously rises up onto unsteady legs. I instruct her to turn her back to Melanie and then lean over until her back is flat, her feet spread as wide as she can comfortably spread them. Once in position, I have Penny reach around the outside of her thighs, take hold of her cream-covered pussy lips, and pull them wide apart to display every bit of her equally wet pinkness. And I have Penny standing so that her pussy is almost over Melanie's feet, as close to Melanie's eyes as she can possibly get. I have Penny stay like that. It also, and coincidentally, has Penny facing Bryce. I have her pick her head up to look at him. Not so that Bryce can see the embarrassment on her face, but to get her head and hair out of Bryce's line of sight. The position already has Penny's arms glued to her sides; now nothing blocks his view of her dangling breasts and those cute tips pointing down with their stiff nipples. Bryce notices. His eyes fix on those rounded mounds. Men!

I tell Melanie to get a very good look at Penny's pussy. And I don't allow Melanie to cheat and simply glance at it. To ensure that Melanie is getting that good look, I first have her describe what she sees. It takes me two scoldings before Melanie finally describes it fully instead of briefly. Then I have Melanie describe Penny's clit. Melanie deems it "very eagerly hard."

I have Melanie describe Penny's tunnel. And I don't let her get away with even a trace of privacy for Penny. It takes me several pointed questions to get Melanie to say enough for me to know that she's gotten a good look at the sticky-wet opening. I ask Melanie one final question: "Now that you've actually seen that cum dumpster, how much dick will it take to satisfy that slutty pussy?"

Melanie says she hasn't a clue. And I remember why I hate reserved women as much as I love them. I ask her how wide Penny's pussy is. She stutters, then says "maybe as wide as a finger, Ma'am?" I ask her how thick of a cock it would take to stuff that sloppy pit full enough for Penny to really feel it. Melanie says "I'd guess about average, Ma'am?" Her voice telling me she hasn't a clue and is just taking a guess. My finger, when I had it inside that pussy, told me that a little less than average would do for Penny. Penny felt a bit tight, but not only is she inexperienced, but she's also a small woman. I let Melanie get away with that answer. I ask her what she thinks "average" width for a dick is. She makes a circle with her fingers that's maybe just under an inch across. I ask her about length, and she holds her hands about five inches apart and tells me she thinks that would be enough for Penny.

"Does Bryce have that much dick?" I ask Melanie.

"I don't know, Ma'am." Of course, she doesn't. She's never even heard of Bryce before Penny tried to sneak him into her bedroom tonight. How could Melanie know anything about him?

"Well, then there's only one way to know if he's able to satisfy even that skanky pussy. You'll just have to find out if he has enough dick for her or not." I don't even take a breath. I go right on telling Penny to go sit on the sofa beside Bryce, and to remember to leave a good foot of space between them. I remind her that she's naked, Bryce isn't, and it would just be way so slutty to be too close to him like that!