Unfortunate Timing

I do my best impersonation of a college professor. "Since you've turned yourself into a gutter whore already, I figure it's past time for you to learn how to be a good, and thus slutty, gutter whore. Lesson one: cock riding. I'm sure this sissy boy won't mind volunteering his cock for your lesson." I have Penny climb up on the table and straddle Bryce's thighs, the front edge of her pubes over his balls.

Penny looks just a little bit more nervous as she climbs up. She's a petite woman. She has to rise up as high as she can, her thighs straight up and down, on her knees to get over Bryce's cock. Even then, as she inches forward to straddle the shaft, its tip brushes along her mound. I get her into place, the tip of the cock nudging into her gash and aimed perfectly for her tunnel.

The very tip of his cock, maybe ¼" of its bulbous wide head, vanishes into her slit. It isn't enough for the cock to reach her tunnel, but it is enough for an agonizing tease for Bryce. It's enough for him to feel Penny's burning wetness on just the very tip of his shaft. I see a smile on his face. I put a hand on his pubes to remind him he's going to lie there and let Penny do everything. And I see a very nervous look on Penny's face now that she can feel the hugeness of his cock against her a pussy as petite as she is.

"Do not resist, bitch." I tell Penny firmly as I take hold of her hips, "I will do everything." I move Penny slowly as I start her inching downward. Immediately the head of his cock starts to press its way between her lips, and then into the rim of her tunnel. Unlike his shaft, the head is as soft as it is wide, allowing the tightness of her pussy to squish it tightly. It takes a second or two until the steely hard shaft starts to enter Penny. Once it does, the meaty walls of her pussy can't squish it. Instead his cock stretches her muscles taut. He's thick enough that, as his shaft enters her, her mound puffs out to the sides, her plump little lips surrounding it.

Penny gasps out a deep, squealy, and girly moan that's half cry. As she sucks in another breath, her jaw hangs open. Penny shivers hard. She blurts out "OHMYGOD!" She sucks in another fast deep breath. So fast it's almost panicked. She cries out "it's too big!" Only her cry is more of a sensual moan than a plea for mercy. She sucks another breath, a little faster and deeper, then cries out "OHMYGOD!" Her voice turns to a shrieking squeal as she adds "it's going to tear me or something!" then Penny shudders hard. As the shudder racks her entire body, it starts her spongy pert breasts dancing. Their wiggling captivates Bryce's eyes.

I feel a light resistance from Penny. I push a little harder to keep her hips moving steadily. It keeps his cock steadily slipping into her pussy. Penny gives up crying out and breathes deep, and erotic, moans. Her pussy stretches wide, her spongy walls squeezing hard around his shaft as they're pulled tauter than ever. She might think it's too wide for her, but it's not. It's only half what her pussy would stretch for a baby. Those walls might be taut, and they might snuggle that shaft tightly, but they have more stretch in them.

Finally, I feel the resistance of his cock reaching the very depths of Penny's pussy. I stop her, there being no pussy left for the 2-plus inches of cock still waiting to slide into her. It leaves about six inches of dick inside her pussy. Her lips cradle around maybe another inch. The last inch is utterly neglected! I hold Penny there.

I wouldn't want Melanie to miss the slut show! After all, Penny got to enjoy watching her swallow his cock. It's only fair that Melanie gets to watch Penny ride it! I summon Melanie and have her sit in a chair across the table from me. It gives her an unhindered view of Bryce's hips and a shameless view of Penny's hips. Actually a good view of everything.

With my hands firmly gripping the bones of Penny's hips, I start moving her. I guide her to rise up all the way with a smooth, steady, and leisurely motion. As I move her, I can actually feel a little drag from her tight walls squeezing hard on his shaft. It doesn't hinder her motions. Her honey is so slippery that his shaft glides through the tight, pulpy channel.

Penny moans. Her moans are loud, deep, and breathy. They're also laced with an urgent, ultra-girly, squeal. And they're heavily laced with tension. But there isn't even a hint of pain in them. I have her hands braced on Bryce's chest, her thumbs at his manly-small nipples. I can see her hands gripping his chest and the hard muscles there. And I see the goosebumps erupt in an instant, covering her pubes, her lips, most of her bottom, and even the very tops of her thighs. Just as I can see the glimmering thick coat of her honey clinging to the veiny, whiteness of his cock skin.

I bring Penny up until only the head of his cock is still inside her lips, which leaves about half of it inside her pussy. Then I smoothly reverse her stoke, bringing her back down. I brought her up enough that all of his steely hard shaft was out of her, and now he gets treated to the sweet sensations of it stretching her pussy taut as it slides back into her burning hot, sloppy wet tunnel all over again.

Penny's moans grow deeper, squeakier, and more urgent by the stroke. I hold her rhythm to the leisurely pace, keeping her casually stroking as much of his cock as she can with that snuggling tightness. By the second stroke, Penny's hips want to speed up. It's instinct. I hold her steady. As she goes on, her instincts try harder and harder to speed her hips up. I keep her steady, and her moans grow more desperate even faster than her urge to pick up the pace.

I doubt Penny will hear me. I can't imagine her hearing anything beyond her shrieking moans. "You like it slow, don't you sissy? This way you can take your time and really enjoy feeling that tight skank pit squeezing all around that cock, can't you?" I can see Penny trembling more and more. Her hands knead Bryce's chest more energetically.

"Yes!... Ma'am!" Bryce groans out in a honeyed, tense voice. His eyes are still fixed on Penny's now-wildly jiggling breasts.

I raise my voice and move my lips close to Penny's ear. I want her to hear this. "You may not cum, bitch. You made yourself a whore. You will be a whore. Whores make their trick cum. If somehow you manage to satisfy this cock, I will tell you to cum. You do not want to disappoint your trick by not satisfying his cock fully. Even more, you do not want to disappoint your Queen." I gently swat her glowing-red bottom with my hand. She doesn't even yelp. She's too busy moaning.

By now, maybe a whole dozen strokes into it, Penny sounds like a porn star. Only Penny isn't faking her moans. "Go on, sissy!" I tell Bryce, "a trick gets to use his whore! Go on, use all of this whore! Stop staring at those boobs and play with them if you want!" Bryce needs no more encouragement. His hands come up quickly, surrounding Penny's firm mounds and kneading them. It makes Penny moan a little louder, with a little more urgency, in her voice. If that's possible!

It goes on for a little over a minute. Then Penny's entire body tenses. She tightens up so much that I'd swear her muscles are harder than Bryce's cock. I see her teeth grit, clenching hard as she screams a long, drawn-out, "EE!" through them. Over the next several seconds, her body trembles sharper and sharper. Her hands grip Bryce's chest with all their strength, her entire fingers, not just her knuckles, turning white with the strain. Her head thrashes from side to side, tossing her silky long hair around wildly. Her eyes squish shut. A few dollops of her pasty honey fall from the back of her pussy, dripping down onto his furry balls. The squirm in her hips turns powerful, crisp, and unpredictable.

I watch Penny closely, knowing that she's already fighting hard to hold back her climax. It only takes a few seconds for me to see the tension in her body start rippling through the last her. It's enough to make the firm globes of her bottom dance as the rippling tenses and releases them. I peek at Penny's crack. I see her tiny little deep-pink asshole spasming. I would so love to ram a finger, or better yet a dildo, up that asshole right now. The only reason I don't is Penny is too inexperienced for that. Now. Maybe not later. I'm very good at training whores.

And then, less than ninety seconds into it. Penny suddenly let's go. In that instant, the tension is gone from her body. She screams a long, sultry, and so-sweet "AH!" An instant later her body shudders violently hard, the tension snapping back as fast as it left, only even harder now. Her head falls back, jaw open, as her scream continues. Her hips snap hard against my grip, trying to impale herself on that cock. I hold her pace steady. She shudders uncontrollably, and wildly, every part of her body thrashing every which way. And she keeps on screaming her lungs out, crying out a fast "UH!" followed by a very long "AH!" over and over again. I can see the lips of her pussy quivering as her honey drips steadily from them. Not just in the back, but all around that fat cock.

Another wave crashes over Penny. The tension pulls her head and shoulders down, curling her towards Bryce. As it flows over her, her shoulders snap back up, sending her head snapping back. She screams more moans. Her bottom fights me hard to slam down on his cock.

Her orgasm goes on for well over a minute, the waves coming fast and hard as they crash over her. I keep her pace steady as they flood through her. Finally, Penny stops screaming her moans. Her head falls limply forward. She pants deep, desperate, fast "OH-UH!s" for a few seconds as she tries to catch her breath. Penny suddenly screams out "UH-OW!" She draws the "ow" out for a second, before screaming "it hurts! I can't!" Then Penny falls limp. Really falls. As in her chest crashes down on Bryce's. With her muscles loose, the sudden motion of her falling pulls her knees back, kicking her feet out toward Bryce's. And that sends her hips down, lying her pubes against his. Her arms lie unmoving at their sides. Her head lands on Bryce's shoulder. She drifts in dreamland's bliss.

I sigh deeply. "What a slut! Can't even wait long enough to satisfy her boy before cumming all over everything!"

I taunt Melanie for a moment, scolding her for not teaching "her little girl" enough about sex that she could at least manage to please a boy. Really I'm giving Penny some time to drift back to reality. It takes her about two minutes before I see the first stirrings in her.

As soon as I do I have Melanie stand up. I tell her that since Penny can't take care of herself, it's Melanie's job to see to her. After all, it was Melanie who failed to teach her how to fuck a boy, wasn't it? I remind Melanie of that yet again in my most condescending voice. I have Melanie pick Penny up, lifting her off Bryce. Melanie strains hard to lift the girl. Penny purrs mutely as Bryce's stiffness slides out of her pussy. I have Melanie sit Penny in the chair. She has to hold Penny up for a moment before Penny gets herself together enough to sit on her own.

I scold Penny in my mean-girl bully voice. "Are you done being a silly little bitch now and play at being a grown-up bitch? Clearly you just a naughty little bitch! A grown-up bitch would have satisfied a sissy like him! But no, you had to be such a skanky little whore and cum all over everything! And now you've left that poor cock unsatisfied! I'll bet that cock is aching and throbbing right now! Dicks hurt when they're fucked and not finished! What kind of a bitch would do that to a boy, worse, a boy she claims to like!"

"I'm sorry, Ma'am," Penny more breathes out in a very dreamy, very honeyed-sweet voice. "Soooo much dick..."

"No bitch of mine is wasting a cock, even if it is attached to a sissy like him!" I scold her firmly. "Luckily for you, your mommy is here. Maybe if you beg her she'll save your sloppy little skank pit from more and finish that cock off for you. Ask nicely, bitch."

Her voice is just as far off and dreamy as it takes on the little girl's tone again. "Mommy, I'm sorry for being such a slut. I'm really sorry for not pleasing my boy. Please, mommy, please! Will you please finish that cock off for me, mommy? Please? Please don't make him go home like this. He'll hate me! Please, mommy?"

It's not Melanie's decision, and Melanie knows it. I don't give her a chance to answer. "Come, slut." I summon Melanie. She comes over to me, her eyes locked on Bryce's cock, and I'm sure her mind imagining how sweet it's going to feel as she fucks it. It is a very nice cock! If Bryce wasn't a sissy, I just might use it myself. But clearly, he is, so I won't. AS Melanie comes to the side of the table, I have Bryce sit up. He grins wide as he does, I'm sure imagining getting a second crack at that mouth that can swallow more cock than even Penny's pussy.

I stop suddenly. Then I blurt out, "slave! I forgot! Melanie's favorite pussy toy is in her bedroom! Go fetch the skanky thing."

"Yes, Mistress." Sophie giggles. She hurries off, knowing what I mean. The "skanky thing" is "skanky whore," the name I made up for Paige. And Paige is a good pussy toy. She eats it well.

A second later Sophie is back, leading Paige on her leash. Paige is still fully naked. Bryce's eyes lock on the newcomer, taking in all of her youthfully pertness, and especially her pointy breasts with wide nipples a decent bit lighter shade of pink than Penny's. Paige is the same age as Penny, and also a petite girl. But Paige is leaner than Penny. And unlike Penny, Paige doesn't show a bit of hesitancy or modesty as she allows Sophie to lead her along by the leash.

I tell Paige to lie on the table. Penny glares at Paige, the dreaminess of her eyes hiding the hatred I know is there. I'm sure Penny is thinking that I'm not just going to allow Bryce to fuck Paige, but make her watch him do it. The leash tells her that Paige is far more experienced than she is, and thus Paige will satisfy him. Bryce watches eagerly, mostly just enjoying the naked woman. Melanie blushes deep and cringes as Paige's appearance reminds her of the girl-on-girl that Penny interrupted. I'm sure Melanie is thinking that sooner or later it will dawn on Penny that Melanie has been messing around with a woman. I'm sure that's the very last thing Melanie would want Penny to know. How shameful for a proper Christian woman to be doing!

Once Paige is lying on the table, I tell Melanie to straddle Paige's face, her butt facing Paige's head. Melanie moves slow and reluctantly. And she starts crying softly as she mounts the table and Paige's lips. I get Melanie into position, her knees spread wide, leaning forward and bracing her hands on the table just in front of her knees. It lowers her pussy fully against Paige's wide mouth.

"Skanky whore, eat that filthy pussy," I tell Paige. Unlike Melanie, Paige doesn't hesitate to obey whatever I command. In a fraction of a second, Melanie moans deeply. In a few more seconds, her moans are uninhibited and loud. Her hips squirm, grinding her pussy down against Paige's mouth.

I have Bryce beside them, and I make sure he gets a moment to enjoy a good view of the sexy-hot Paige eating Melanie's pussy shamelessly. And very skillfully. He can see that in Melanie's energetic squirming and moans. I let him watch for a couple of minutes.

Penny can see it well from her seat, too. But still basking in the afterglow of what must have been an orgasm more intense than she knew she was capable of, Penny doesn't show much. Still, she watches and doesn't avert her eyes. I can only guess what must be going through Penny's mind. Anything from now having material to torture Melanie with, to wondering how to ask me to teach her to eat a woman like that. She definitely sees how interested Bryce is, and how much watching it is arousing him. The twitches that make his cock dance around advertise his appreciation for the show.

I reach down. From behind Bryce, I slip my hand between his thighs. I gently cup his balls in my hand, not holding them, but more just letting them rest in the cup of my hand. I very tenderly stroke the backside of his sack with the pad of my thumb. "go on, sissy. You don't have to be shy! My slut has two holes and that skanky whore is only using one. That leaves one for you. Go ahead, fuck it and get your relief."

Bryce freezes, not believing what he's hearing. His eyes lock on the rounded, slightly loose, decently pink, globes of Melanie's bottom. They jiggle slightly for our entertainment as Melanie's hips squirm more and more eagerly on Paige's lips. He hesitates.

I stroke his sack. "What's a matter, sissy? Haven't you ever done it like that before?"

"No, Ma'am." Bryce stutters his answer, his voice mute, his words trembling and unsure.

"Don't you want to try that? I thought all boys liked it."

"Yes, Ma'am." a little firmness creeps into his voice. "but..."

"There's only one butt, sissy. Melanie's very slutty, very dirty butt! Go on. I won't ask again."

Before I have a chance to release his balls, he moves forward. It lifts his sack from my hand. As he climbs up on the table, I tell him (nicely) to straddle Paige's chest. He doesn't mind that at all.

"Since this is a first for you, sissy, I'll teach you how to do it properly." I take hold of the base of his cock. I tease the tip of his cock head along Melanie's gash, getting a nice coat of her slick, creamy honey on it. Hers is thinner than Penny's, and not quite as slippery. But definitely slippery enough. I move the bulbous head up, pressing it into the V-cleft of Melanie's crack. It pushes her cheeks aside and slides right up. I stop it with its tip centered on the small ring of Melanie's asshole. Even the rounded tip of his cock is wide enough to fully cover the ring. His shaft is so wide that it doesn't even fit in her crack without pushing her cheeks out enough that their edges take a gentle arc around it. I guide him to put a firm, steady pressure against the tightly clenched muscle, and hold it there. I take my hand from his cock. "Do not do anything, sissy. My slut will swallow your cock with her butt. You will let her do it for you, like only the skankiest of street-corner whores, and porn stars, would." Bryce stays where I put him.

"Slut, take that dick up your butt." I walk around and glare into Melanie's eyes as I give the order. Melanie's glassy eyes which have long ago forgotten that Melanie thinks she's a proper, prim, woman. The eyes of a slut lost in ecstasy. Melanie moans out "yes, Ma'am."

I've taught Melanie this trick, too. But this is the first time she's had to do it for a man instead of a dildo. Thankfully I use a rather generous dildo to train my sluts. That way, when an unexpectedly large cock happens into the games, it's not a horrific surprise for her. She knows she can handle it. Like now.

Melanie takes a deep breath, sucking all the air she can into her lungs. She pushes back hard, straining to force her ring against his cock. It's the same technique I taught Penny to ease my finger into her. Only Melanie has more practice at it. Her asshole pushes back firmly. He obediently stays where I put him, his cock unyielding as the pressure grows. In an instant, her asshole surrenders. As it presses back again him, his shaft begins to stretch it wide. Its flesh pulls taut, her muscle's rubberiness first loose, then tightening as it's stretched wider and wider. The pink skin pulls ever tauter, stretching almost fully to its limit. Her muscle doesn't have much more give to it, now hard as his cock stretches it even more. Finally, Melanie grunts out a throaty, sultry, "UH!" that's strained, but not pained. His cock begins slowly slipping into the ring.